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$1,800,000

Steeped in Key West history and unlike anything else available in Old Town, 511 Tabby Lane presents an opportunity to own one of the island's most extraordinary properties. Hidden away at the end of a charming pedestrian lane with direct access to iconic Duval Street, this remarkably private home offers a level of seclusion and potential that is virtually impossible to replicate. Rich in character and history, the property sits on an exceptionally deep 4,200-square-foot lot, a rarity in Old Town. There is simply no other property currently available that offers this combination of privacy, location, and land. The expansive lot provides endless possibilities, with ample space for a pool, pool house, guest quarters, lush gardens, outdoor entertaining areas, and more while still preserving the home's unique Old Town charm. Completely hidden from view behind a gated entrance, the property feels like a private tropical sanctuary in the heart of Key West. Whether you envision thoughtfully restoring the existing residence or creating a one-of-a-kind island compound, the possibilities are exceptional. The structure is believed to be a non-contributing building with HARC (buyer to verify), offering additional flexibility for future improvements. Adding to its rarity, the property is zoned for Transient License Receivership (buyer to verify), making it an incredibly attractive opportunity for investors, developers, or anyone seeking a truly unique Old Town residence. Properties of this caliber and significance rarely become available. 511 Tabby Lane represents a chance to own a piece of Key West history while creating something that future generations will treasure. This is Old Town at its most authentic--and an opportunity that simply cannot be duplicated.

3 Beds ⋅ 1 Baths ⋅ 620880 MLS

Steeped in Key West history and unlike anything else available in Old Town, 511 Tabby Lane presents an opportunity to own one of the island's most extraordinary properties. Hidden away at the end of a charming pedestrian lane with direct access to iconic Duval Street, this remarkably private home offers a level of seclusion and potential that is virtually impossible to replicate. Rich in character and history, the property sits on an exceptionally deep 4,200-square-foot lot, a rarity in Old Town. There is simply no other property currently available that offers this combination of privacy, location, and land. The expansive lot provides endless possibilities, with ample space for a pool, pool house, guest quarters, lush gardens, outdoor entertaining areas, and more while still preserving the home's unique Old Town charm. Completely hidden from view behind a gated entrance, the property feels like a private tropical sanctuary in the heart of Key West. Whether you envision thoughtfully restoring the existing residence or creating a one-of-a-kind island compound, the possibilities are exceptional. The structure is believed to be a non-contributing building with HARC (buyer to verify), offering additional flexibility for future improvements. Adding to its rarity, the property is zoned for Transient License Receivership (buyer to verify), making it an incredibly attractive opportunity for investors, developers, or anyone seeking a truly unique Old Town residence. Properties of this caliber and significance rarely become available. 511 Tabby Lane represents a chance to own a piece of Key West history while creating something that future generations will treasure. This is Old Town at its most authentic--and an opportunity that simply cannot be duplicated.

511 Tabby Ln, Key West

$2,475,000

Experience the best of waterfront living at 3206 Riviera Drive, a beautifully updated canal-front home offering 60 feet of waterfront, exceptional privacy, and direct access to the Key West boating lifestyle. With no homes across the canal, the property enjoys peaceful water views and a uniquely private setting. Designed for both everyday living and entertaining, the open-concept interior is filled with natural light and seamlessly connects to the outdoors through a wall of impact-rated sliding glass doors. The chef's kitchen features premium cabinetry, a large center island, and a waterfront dining area overlooking the pool and canal. The home offers three spacious bedrooms, including two en-suite bedrooms, three full bathrooms, a dedicated laundry room, two-zone air conditioning, and a whole-home generator. Outside, the tropical backyard is built for enjoying the Keys. Relax by the newly renovated heated pool, entertain from the outdoor kitchen, unwind on the screened patio, or enjoy the convenience of an outdoor bathroom. Shell stone limestone walkways, lush landscaping, covered parking, and a fully gated lot complete this private waterfront retreat. Offering the perfect combination of luxury, comfort, and functionality, 3206 Riviera Drive is move-in ready and seller financing may be available.

3 Beds ⋅ 3 Baths ⋅ 620879 MLS

Experience the best of waterfront living at 3206 Riviera Drive, a beautifully updated canal-front home offering 60 feet of waterfront, exceptional privacy, and direct access to the Key West boating lifestyle. With no homes across the canal, the property enjoys peaceful water views and a uniquely private setting. Designed for both everyday living and entertaining, the open-concept interior is filled with natural light and seamlessly connects to the outdoors through a wall of impact-rated sliding glass doors. The chef's kitchen features premium cabinetry, a large center island, and a waterfront dining area overlooking the pool and canal. The home offers three spacious bedrooms, including two en-suite bedrooms, three full bathrooms, a dedicated laundry room, two-zone air conditioning, and a whole-home generator. Outside, the tropical backyard is built for enjoying the Keys. Relax by the newly renovated heated pool, entertain from the outdoor kitchen, unwind on the screened patio, or enjoy the convenience of an outdoor bathroom. Shell stone limestone walkways, lush landscaping, covered parking, and a fully gated lot complete this private waterfront retreat. Offering the perfect combination of luxury, comfort, and functionality, 3206 Riviera Drive is move-in ready and seller financing may be available.

3206 Riviera Dr, Key West

$875,000

Nestled in the serene Bay Manor neighborhood, this beautiful single-family home seamlessly blends comfort with tropical charm. The home boasts a master suite, complemented by 2 additional well-sized bedrooms and 2 full baths. Enjoy a kitchen featuring sleek granite counter tops. A large pantry/laundry room enhances functionality, while the expansive backyard offers ample space for entertaining and a pool. The rear yard is highlighted by a carport and a large cabana-style building, perfect for gatherings or relaxation. Mature trees, lush greenery, a fruit bearing mango tree and a privacy fence surround the property, providing a private and tranquil setting. Conveniently located in New Town near schools and shopping with off street parking. Just a short drive to Key West's vibrant downtown, offering dining, shopping, and cultural attractions. Nearby parks and waterfront areas provide opportunities for boating, fishing, and enjoying the island's natural beauty. Whether you're seeking a vacation retreat, investment property, or full-time residence, this property presents an ideal opportunity to experience the laid-back Key West. One of the listing realtors is related to the sellers.

3 Beds ⋅ 2 Baths ⋅ 620866 MLS

Nestled in the serene Bay Manor neighborhood, this beautiful single-family home seamlessly blends comfort with tropical charm. The home boasts a master suite, complemented by 2 additional well-sized bedrooms and 2 full baths. Enjoy a kitchen featuring sleek granite counter tops. A large pantry/laundry room enhances functionality, while the expansive backyard offers ample space for entertaining and a pool. The rear yard is highlighted by a carport and a large cabana-style building, perfect for gatherings or relaxation. Mature trees, lush greenery, a fruit bearing mango tree and a privacy fence surround the property, providing a private and tranquil setting. Conveniently located in New Town near schools and shopping with off street parking. Just a short drive to Key West's vibrant downtown, offering dining, shopping, and cultural attractions. Nearby parks and waterfront areas provide opportunities for boating, fishing, and enjoying the island's natural beauty. Whether you're seeking a vacation retreat, investment property, or full-time residence, this property presents an ideal opportunity to experience the laid-back Key West. One of the listing realtors is related to the sellers.

2928 Fogarty Ave, Key West

$615,000

In New Town, where island convenience meets everyday ease, this beautifully renovated home delivers the kind of low-maintenance, family-ready living that's increasingly hard to find in Key West. Offered at $615,000, three-bedroom homes at this level are a rarity on the island, making this an exceptional entry point into Keys ownership. Set on a 2,055 sq. ft. lot with a fully fenced front yard, the home welcomes children and pets alike into a private, secure outdoor retreat -- a rare offering so close to town. Inside, 1,264 sq. ft. of thoughtfully renovated living space unfolds across two levels, beginning with a ground-floor primary suite positioned just off the open kitchen and living area, ideal for single-level living or a private guest retreat. The kitchen has been tastefully updated with new cabinetry and granite countertops, anchoring a bright, tiled main level built for effortless entertaining. Recently installed impact windows and doors on the first floor bring both peace of mind and energy efficiency, a significant upgrade in the islands. Upstairs, two additional bedrooms share a well-appointed bath beneath cozy carpeted flooring, while a versatile exterior porch off the second floor offers flexibility to enclose as a home office, additional storage, or a walk-in closet -- or simply enjoyed as-is for morning coffee in the island breeze. With no HOA or condo fees, ownership here comes with true freedom -- no added costs, no added rules. Sold unfurnished and ready for immediate occupancy, this home offers a seamless path to island living without delay. Located within easy reach of top schools and Key West's favorite shopping destinations, this is a rare opportunity to plant roots in the Keys without compromise. Welcome home to island living, made simple.

3 Beds ⋅ 2 Baths ⋅ 620811 MLS

In New Town, where island convenience meets everyday ease, this beautifully renovated home delivers the kind of low-maintenance, family-ready living that's increasingly hard to find in Key West. Offered at $615,000, three-bedroom homes at this level are a rarity on the island, making this an exceptional entry point into Keys ownership. Set on a 2,055 sq. ft. lot with a fully fenced front yard, the home welcomes children and pets alike into a private, secure outdoor retreat -- a rare offering so close to town. Inside, 1,264 sq. ft. of thoughtfully renovated living space unfolds across two levels, beginning with a ground-floor primary suite positioned just off the open kitchen and living area, ideal for single-level living or a private guest retreat. The kitchen has been tastefully updated with new cabinetry and granite countertops, anchoring a bright, tiled main level built for effortless entertaining. Recently installed impact windows and doors on the first floor bring both peace of mind and energy efficiency, a significant upgrade in the islands. Upstairs, two additional bedrooms share a well-appointed bath beneath cozy carpeted flooring, while a versatile exterior porch off the second floor offers flexibility to enclose as a home office, additional storage, or a walk-in closet -- or simply enjoyed as-is for morning coffee in the island breeze. With no HOA or condo fees, ownership here comes with true freedom -- no added costs, no added rules. Sold unfurnished and ready for immediate occupancy, this home offers a seamless path to island living without delay. Located within easy reach of top schools and Key West's favorite shopping destinations, this is a rare opportunity to plant roots in the Keys without compromise. Welcome home to island living, made simple.

3206 Harriet Ave, Key West

$1,100,000

Welcome to your ultimate Old Town retreat. Nestled just four blocks from the iconic Blue Heaven and the legendary Hemingway House, this century-old historic Conch house invites you to step past its classic white picket fence and onto a quintessential front porch made for lazy afternoons. Open the front door and you are greeted by the seamless flow of a bright, airy layout. The open-concept living space and kitchen serve as a canvas framed by durable vinyl plank flooring and impact windows, entirely ready for your personal style updates. Moving through the home, the versatile floor plan maximizes privacy with three distinct suites, each uniquely paired with its own dedicated bathroom. The front suite offers a private retreat featuring its own closet and an en-suite bath equipped with a convenient built-in laundry area. Further inside, the middle suite provides a more spacious getaway boasting double closets and an attached full bath. At the rear of the home, an adaptable third suite with an attached bath functions beautifully as a bedroom, private home office, or a cozy den. Step out the back door to a small private patio area wrapped in a barrier of mature palms. Best of all, this historic gem comes with the ultimate Old Town luxury of coveted off-street parking for one vehicle. Rich in character and offered at a great price tag, this three-bedroom gem won't last long - Schedule a private showing today!

3 Beds ⋅ 3 Baths ⋅ 620779 MLS

Welcome to your ultimate Old Town retreat. Nestled just four blocks from the iconic Blue Heaven and the legendary Hemingway House, this century-old historic Conch house invites you to step past its classic white picket fence and onto a quintessential front porch made for lazy afternoons. Open the front door and you are greeted by the seamless flow of a bright, airy layout. The open-concept living space and kitchen serve as a canvas framed by durable vinyl plank flooring and impact windows, entirely ready for your personal style updates. Moving through the home, the versatile floor plan maximizes privacy with three distinct suites, each uniquely paired with its own dedicated bathroom. The front suite offers a private retreat featuring its own closet and an en-suite bath equipped with a convenient built-in laundry area. Further inside, the middle suite provides a more spacious getaway boasting double closets and an attached full bath. At the rear of the home, an adaptable third suite with an attached bath functions beautifully as a bedroom, private home office, or a cozy den. Step out the back door to a small private patio area wrapped in a barrier of mature palms. Best of all, this historic gem comes with the ultimate Old Town luxury of coveted off-street parking for one vehicle. Rich in character and offered at a great price tag, this three-bedroom gem won't last long - Schedule a private showing today!

1017 Thomas St, Key West

$3,180,000

Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure. A worry free and easily maintained 3 bedroom, 2 and & ½ bath home, master bath ensuite, on one of the most prestigious streets in Key West, this home is constantly photographed, whether it's the location, the style, or the carefully chosen color pallet by the current owners, we're not sure, but regardless, many are drawn to this home and its beautifully tailored look. Whether you want to people watch on the front porch and sip your coffee or cocktail, or withdraw to the secluded private back yard and lounge around the pool reading a Hemingway novel, who's legendary home is a mere stroll moments away out the gate one direction, or go the opposite direction to the Atlantic Ocean and the Southernmost Point Buoy, everything Key West is only minutes away from this front door, your front door. Your new home. And by new, that's what we mean-this home was carefully and completely renovated in the last couple years, essentially creating a classic Key West house, with all the comfort and benefits of a new home. A completely custom Bosch appliance filled kitchen, with virtually every modern convenience a new home would hold. Modern upscale interior, zoned central A/C system with whole-house ventilating dehumidifier, advanced internet modem and router system, maintenance free composite decking, complete security and camera system, are just a few of the extra steps the owners took when creating a time-honored but luxurious, self contained and above the norm renovation of this truly one of a kind Key West home. Lets set up your private showing today.

3 Beds ⋅ 3 Baths ⋅ 620747 MLS

Classic Key West charm and sophistication abound, with traditional grace yet modern conveniences, this wasn't just a simple remodel. This was a carefully thought out, complete and careful renovation of this Old Town treasure. A worry free and easily maintained 3 bedroom, 2 and & ½ bath home, master bath ensuite, on one of the most prestigious streets in Key West, this home is constantly photographed, whether it's the location, the style, or the carefully chosen color pallet by the current owners, we're not sure, but regardless, many are drawn to this home and its beautifully tailored look. Whether you want to people watch on the front porch and sip your coffee or cocktail, or withdraw to the secluded private back yard and lounge around the pool reading a Hemingway novel, who's legendary home is a mere stroll moments away out the gate one direction, or go the opposite direction to the Atlantic Ocean and the Southernmost Point Buoy, everything Key West is only minutes away from this front door, your front door. Your new home. And by new, that's what we mean-this home was carefully and completely renovated in the last couple years, essentially creating a classic Key West house, with all the comfort and benefits of a new home. A completely custom Bosch appliance filled kitchen, with virtually every modern convenience a new home would hold. Modern upscale interior, zoned central A/C system with whole-house ventilating dehumidifier, advanced internet modem and router system, maintenance free composite decking, complete security and camera system, are just a few of the extra steps the owners took when creating a time-honored but luxurious, self contained and above the norm renovation of this truly one of a kind Key West home. Lets set up your private showing today.

1019 Whitehead St, Key West

$4,499,999

Located in the Beach Club, this reimagined residence offers a rare combination of luxury, privacy, and oceanfront living within one of Key West's premier & financially secure condo communities. This 3 bed, 3 bath residence encompasses 2,309 sq ft of thoughtfully designed living space with views of the Atlantic Ocean. Offered fully furnished, every detail has been curated to blend contemporary elegance with the relaxed refinement of island living. A robust high-speed WiFi system with multiple access points & 800 Mbps of service enhances the home's modern convenience. Walls of pocket glass doors frame endless ocean vistas while filling the living spaces with natural light. Designer lighting, Hunter Douglas Luminette sheer window treatments, and exceptional craftsmanship are showcased throughout. The kitchen features Miele appliances, integrated cabinet lighting, custom-organized drawers, and an innovative smart-glass circular window connecting the kitchen and dining area. With the touch of a button, the glass transitions from opaque to transparent. Designed for both entertaining and everyday living, the open-concept living and dining areas flow seamlessly. The dining space is highlighted by striking brass architectural lighting, while a custom-built bar with a wine cooler and ice maker creates an inviting entertaining alcove. The terrace extends the living space outdoors, offering a comfortable setting to enjoy the surrounding views. The primary suite features a distinctive white oak accent wall, built-in workspace and vanity with concealed power outlets, a spa-inspired bath, generous closet space, dual shoe closets, and a private waterfront terrace. One guest bedroom doubles as a media room with designer floral wall covering and club chairs that convert into twin beds. The third guest bedroom is a spacious ensuite retreat offering comfort and privacy. Residents enjoy gated access, exceptional amenities, covered deeded parking space, & private storage.

3 Beds ⋅ 3 Baths ⋅ 620745 MLS

Located in the Beach Club, this reimagined residence offers a rare combination of luxury, privacy, and oceanfront living within one of Key West's premier & financially secure condo communities. This 3 bed, 3 bath residence encompasses 2,309 sq ft of thoughtfully designed living space with views of the Atlantic Ocean. Offered fully furnished, every detail has been curated to blend contemporary elegance with the relaxed refinement of island living. A robust high-speed WiFi system with multiple access points & 800 Mbps of service enhances the home's modern convenience. Walls of pocket glass doors frame endless ocean vistas while filling the living spaces with natural light. Designer lighting, Hunter Douglas Luminette sheer window treatments, and exceptional craftsmanship are showcased throughout. The kitchen features Miele appliances, integrated cabinet lighting, custom-organized drawers, and an innovative smart-glass circular window connecting the kitchen and dining area. With the touch of a button, the glass transitions from opaque to transparent. Designed for both entertaining and everyday living, the open-concept living and dining areas flow seamlessly. The dining space is highlighted by striking brass architectural lighting, while a custom-built bar with a wine cooler and ice maker creates an inviting entertaining alcove. The terrace extends the living space outdoors, offering a comfortable setting to enjoy the surrounding views. The primary suite features a distinctive white oak accent wall, built-in workspace and vanity with concealed power outlets, a spa-inspired bath, generous closet space, dual shoe closets, and a private waterfront terrace. One guest bedroom doubles as a media room with designer floral wall covering and club chairs that convert into twin beds. The third guest bedroom is a spacious ensuite retreat offering comfort and privacy. Residents enjoy gated access, exceptional amenities, covered deeded parking space, & private storage.

1500 Atlantic Blvd Unit 308, Key West

$599,000

Spacious & Private 3-Bedroom Townhouse with Exceptional Outdoor Living. Enjoy the privacy and space of this beautifully maintained townhouse that's larger than most! This 3-bedroom, 2-bath home features numerous recent improvements, making it move-in ready while leaving plenty of opportunity to add your personal style. Recent improvements include new flooring in the second and third bedrooms as well as the upstairs landing, a brand-new front door and laundry room door, new gutters, and new soffits with specialty color-changing lighting that creates the perfect ambiance for outdoor entertaining. Step outside to a spacious outdoor retreat featuring tropical foliage a deck that's only two years old and a paved patio/driveway completed just three years ago. The fully fenced yard offers outstanding privacy, off-street parking, or enough space to park your boat trailer or even add a pool. A storage shed provides extra room for tools, toys, and outdoor equipment. Whether you prefer relaxing indoors or entertaining outside, this home is perfectly designed for both. It's a wonderful place to call home.

3 Beds ⋅ 2 Baths ⋅ 620741 MLS

Spacious & Private 3-Bedroom Townhouse with Exceptional Outdoor Living. Enjoy the privacy and space of this beautifully maintained townhouse that's larger than most! This 3-bedroom, 2-bath home features numerous recent improvements, making it move-in ready while leaving plenty of opportunity to add your personal style. Recent improvements include new flooring in the second and third bedrooms as well as the upstairs landing, a brand-new front door and laundry room door, new gutters, and new soffits with specialty color-changing lighting that creates the perfect ambiance for outdoor entertaining. Step outside to a spacious outdoor retreat featuring tropical foliage a deck that's only two years old and a paved patio/driveway completed just three years ago. The fully fenced yard offers outstanding privacy, off-street parking, or enough space to park your boat trailer or even add a pool. A storage shed provides extra room for tools, toys, and outdoor equipment. Whether you prefer relaxing indoors or entertaining outside, this home is perfectly designed for both. It's a wonderful place to call home.

3326 Eagle Ave, Key West

$2,089,000

1706 Seminary Street delivers the space, flexibility, and outdoor lifestyle that can be surprisingly difficult to find in Key West. Set behind a new privacy fence on an expansive 7,480SF lot, the home is near an impressive collection of beautifully maintained and upscale residences, adding to the appeal of this desirable neighborhood. This completely renovated 3 bed, 3 bath home offers nearly 2,000SF of beautifully updated living space, including a versatile third bedroom with its own private entrance, ideal for visiting friends and family, a private home office, or potential rental use. At the heart of the home is a striking new kitchen featuring quartz waterfall countertops, custom cabinetry, new KitchenAid stainless steel appliances, and an open design that connects naturally to the surrounding living spaces. One of the home's most inviting spaces is the glass windows surrounding the family room, where abundant natural light and views of the tropical backyard create a connection to the outdoors. Outside is where this property truly comes into its own. Meandering pathways weave through lush tropical landscaping and connect multiple areas designed for enjoying the Key West lifestyle. A resort style L shaped lap pool anchors the backyard, complemented by 2 covered lounging areas, a Bahama inspired outdoor dining space, an outdoor shower, and a secure storage shed. Along the side of the property, another unique opportunity awaits. With a modification to the existing fence, there is potential for approximately 20ft of covered boat storage, an increasingly valuable feature for anyone looking to keep their boat protected from the Key West sun and weather. Private, beautifully renovated, and designed to make the most of its generous lot, the property offers a rare combination of indoor comfort, outdoor living, and everyday functionality. Whether enjoyed as a primary residence or an island retreat, everything is already in place to start living the Key West lifestyle.

3 Beds ⋅ 3 Baths ⋅ 620712 MLS

1706 Seminary Street delivers the space, flexibility, and outdoor lifestyle that can be surprisingly difficult to find in Key West. Set behind a new privacy fence on an expansive 7,480SF lot, the home is near an impressive collection of beautifully maintained and upscale residences, adding to the appeal of this desirable neighborhood. This completely renovated 3 bed, 3 bath home offers nearly 2,000SF of beautifully updated living space, including a versatile third bedroom with its own private entrance, ideal for visiting friends and family, a private home office, or potential rental use. At the heart of the home is a striking new kitchen featuring quartz waterfall countertops, custom cabinetry, new KitchenAid stainless steel appliances, and an open design that connects naturally to the surrounding living spaces. One of the home's most inviting spaces is the glass windows surrounding the family room, where abundant natural light and views of the tropical backyard create a connection to the outdoors. Outside is where this property truly comes into its own. Meandering pathways weave through lush tropical landscaping and connect multiple areas designed for enjoying the Key West lifestyle. A resort style L shaped lap pool anchors the backyard, complemented by 2 covered lounging areas, a Bahama inspired outdoor dining space, an outdoor shower, and a secure storage shed. Along the side of the property, another unique opportunity awaits. With a modification to the existing fence, there is potential for approximately 20ft of covered boat storage, an increasingly valuable feature for anyone looking to keep their boat protected from the Key West sun and weather. Private, beautifully renovated, and designed to make the most of its generous lot, the property offers a rare combination of indoor comfort, outdoor living, and everyday functionality. Whether enjoyed as a primary residence or an island retreat, everything is already in place to start living the Key West lifestyle.

1706 Seminary St, Key West

$1,149,000

Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly rare in Key West: a property with nothing to do but move in and enjoy. With its classic stone facade, this 1952 residence captures the distinctive architectural style that defined post-war Key West, delivering 1,445 sq. ft. of low-maintenance living, ideal for the second-home buyer who wants the Key West lifestyle without the upkeep of a larger historic home. Tile floors run throughout, complementing a solid wood kitchen that retains its excellent-condition granite countertops. A versatile Florida room to the rear opens through French doors to the back garden, equally suited as a formal dining room, a home office, or a playroom. Beyond, the backyard is a blank canvas, ready to become a stunning tropical Key West oasis complete with an outdoor entertaining area. The detached guest cottage, with its own private entrance, adds a third bedroom to the property and is currently leased to a long-term tenant (Lease expires Sept 30th 2026) at a meaningful monthly rent, offering established income with true separation of space, a compelling proposition for the second-homeowner who wants their property earning for them even when they're not there to enjoy it. A covered carport for two vehicles and abundant storage round out the property's everyday practicality. Offered at a clear value against comparable Midtown properties, this is an entry point into island living that is as flexible as it is rare. Welcome to Key West Living at its finest.

3 Beds ⋅ 2 Baths ⋅ 620641 MLS

Tucked into the leafy heart of Midtown, just a quick bike ride from Smathers Beach, Higgs Beach and the energy of downtown, 1708 South St. offers something increasingly rare in Key West: a property with nothing to do but move in and enjoy. With its classic stone facade, this 1952 residence captures the distinctive architectural style that defined post-war Key West, delivering 1,445 sq. ft. of low-maintenance living, ideal for the second-home buyer who wants the Key West lifestyle without the upkeep of a larger historic home. Tile floors run throughout, complementing a solid wood kitchen that retains its excellent-condition granite countertops. A versatile Florida room to the rear opens through French doors to the back garden, equally suited as a formal dining room, a home office, or a playroom. Beyond, the backyard is a blank canvas, ready to become a stunning tropical Key West oasis complete with an outdoor entertaining area. The detached guest cottage, with its own private entrance, adds a third bedroom to the property and is currently leased to a long-term tenant (Lease expires Sept 30th 2026) at a meaningful monthly rent, offering established income with true separation of space, a compelling proposition for the second-homeowner who wants their property earning for them even when they're not there to enjoy it. A covered carport for two vehicles and abundant storage round out the property's everyday practicality. Offered at a clear value against comparable Midtown properties, this is an entry point into island living that is as flexible as it is rare. Welcome to Key West Living at its finest.

1708 South Street, Key West

$4,400,000

An exceptional opportunity to own one of Old Town Key West's most recognizable mixed-use investment properties. Perfectly positioned at the prominent corner of Whitehead Street and Front Street, Little Shops Off Duval enjoys unmatched pedestrian exposure in the heart of the Historic Seaport and Cruise Ship District. Located adjacent to the Mel Fisher Maritime Museum and directly across from the Audubon House, this iconic property sits along one of the busiest tourist corridors in Key West. The property encompasses approximately 7,755 square feet and features six established commercial storefronts together with a spacious three-bedroom, two-bath residential apartment, creating a diversified income-producing asset with both commercial and residential revenue streams. Long-standing tenants, and separate utility meters. Opportunities to acquire a premier corner property in this location are exceptionally rare. Whether you're seeking a legacy investment, a trophy commercial asset, or a high-profile addition to your portfolio, Little Shops Off Duval represents one of the most unique commercial ownership opportunities in the Florida Keys.

3 Beds ⋅ 5 Baths ⋅ 620614 MLS

An exceptional opportunity to own one of Old Town Key West's most recognizable mixed-use investment properties. Perfectly positioned at the prominent corner of Whitehead Street and Front Street, Little Shops Off Duval enjoys unmatched pedestrian exposure in the heart of the Historic Seaport and Cruise Ship District. Located adjacent to the Mel Fisher Maritime Museum and directly across from the Audubon House, this iconic property sits along one of the busiest tourist corridors in Key West. The property encompasses approximately 7,755 square feet and features six established commercial storefronts together with a spacious three-bedroom, two-bath residential apartment, creating a diversified income-producing asset with both commercial and residential revenue streams. Long-standing tenants, and separate utility meters. Opportunities to acquire a premier corner property in this location are exceptionally rare. Whether you're seeking a legacy investment, a trophy commercial asset, or a high-profile addition to your portfolio, Little Shops Off Duval represents one of the most unique commercial ownership opportunities in the Florida Keys.

218 Whitehead St, Key West

$1,575,000

Experience the best of Old Town Key West in this beautifully updated 3-bedroom, 2-bath home offering the ease of single-level living. Inside, you'll find hardwood floors, tall ceilings, French doors, stainless steel appliances, and an inviting open layout filled with natural light. Designed for the Key West lifestyle, the private backyard features a saltwater pool with heater and chiller, outdoor shower, lush tropical landscaping, spacious patio, and two dedicated off-street parking spaces. This property is turnkey, fully furnished and ready to enjoy from day one. Well maintained and tastefully updated, recent improvements include a new HVAC system, saltwater pool system, updated furnishings and termite tenting. Currently operating as a monthly vacation rental with an established rental history. Located in the center of Old Town just moments from Higgs Beach, Duval Street, the Historic Seaport, neighborhood cafés, restaurants and shopping. This property offers the privacy and feel of a single family home, it is part of an intimate two-unit condominium association with no shared common elements. Whether you're looking for a successful investment property, a full-time residence, or your own island getaway, this home checks every box. Schedule your private showing today to explore this Key West opportunity.

3 Beds ⋅ 2 Baths ⋅ 620577 MLS

Experience the best of Old Town Key West in this beautifully updated 3-bedroom, 2-bath home offering the ease of single-level living. Inside, you'll find hardwood floors, tall ceilings, French doors, stainless steel appliances, and an inviting open layout filled with natural light. Designed for the Key West lifestyle, the private backyard features a saltwater pool with heater and chiller, outdoor shower, lush tropical landscaping, spacious patio, and two dedicated off-street parking spaces. This property is turnkey, fully furnished and ready to enjoy from day one. Well maintained and tastefully updated, recent improvements include a new HVAC system, saltwater pool system, updated furnishings and termite tenting. Currently operating as a monthly vacation rental with an established rental history. Located in the center of Old Town just moments from Higgs Beach, Duval Street, the Historic Seaport, neighborhood cafés, restaurants and shopping. This property offers the privacy and feel of a single family home, it is part of an intimate two-unit condominium association with no shared common elements. Whether you're looking for a successful investment property, a full-time residence, or your own island getaway, this home checks every box. Schedule your private showing today to explore this Key West opportunity.

1005 Watson St Unit 1, Key West

$992,000

Old Town 'Diamond in the Rough' near Bay View Park with the highly coveted Off-Street parking. Unique opportunity to acquire a corner lot of over 4,500 sq ft in quiet Old Town neighborhood. Good amount of yard space. No active or expired building permits or code cases. Being sold As-Is with no repair & no clean up. Does have an existing fiberglass pool surrounded by a wooden deck. There is an existing concrete pad behind a double fence that could provide secured off street parking. Side yard is 37 Ft from side of house to fence and 49 Ft wide. Back yard with pool and deck is 27 X 27. Lots of potential. Major renovation project. Probably needs cash buyer. Contract requires court approval due to guardianship. Proof of funds must accompany offer. Create your island oasis at 1119 Florida St.

3 Beds ⋅ 2 Baths ⋅ 620547 MLS

Old Town 'Diamond in the Rough' near Bay View Park with the highly coveted Off-Street parking. Unique opportunity to acquire a corner lot of over 4,500 sq ft in quiet Old Town neighborhood. Good amount of yard space. No active or expired building permits or code cases. Being sold As-Is with no repair & no clean up. Does have an existing fiberglass pool surrounded by a wooden deck. There is an existing concrete pad behind a double fence that could provide secured off street parking. Side yard is 37 Ft from side of house to fence and 49 Ft wide. Back yard with pool and deck is 27 X 27. Lots of potential. Major renovation project. Probably needs cash buyer. Contract requires court approval due to guardianship. Proof of funds must accompany offer. Create your island oasis at 1119 Florida St.

1119 Florida St, Key West

$849,000

Adorable 2 bed ,1.5 bath single family home in Pearlman neighborhood with separate 1-1 cottage anchored by a picturesque Royal Poinciana tree out front! Features a large (16 X 15) screen room between the main house & the cottage. You can pass from the main house thru the screened room into the cottage & still be under roof. Cottage does have its own separate entrance. Use the cottage as an extension of the main house or as separate living space, she-shed, man-cave, studio, work out room or home office. Roof replaced in 2016. Exposed beam ceilings in kitchen and dining areas. For those familiar with the 'Sunshine Homes' in KW, you know they were built with crawl spaces between the ground & the floor, taller attics w/ pull-down stairs, beautiful hard wood floors & asbestos siding. Most of main house still has original hard wood floors & the cottage has bamboo flooring. Sellers say interior of house did not flood during Wilma. 3712 Duck affords you yard space, room for pool, carport with additional off-street parking & one of KW's most desirable New Town neighborhoods. Convenient location is close to schools, shopping, theaters, medical offices, ball fields, beach, airport, golf course & hospital. Just a short ride into Old Town & world-famous Duval St.. Make your next home at 3712 Duck Ave!

3 Beds ⋅ 3 Baths ⋅ 620501 MLS

Adorable 2 bed ,1.5 bath single family home in Pearlman neighborhood with separate 1-1 cottage anchored by a picturesque Royal Poinciana tree out front! Features a large (16 X 15) screen room between the main house & the cottage. You can pass from the main house thru the screened room into the cottage & still be under roof. Cottage does have its own separate entrance. Use the cottage as an extension of the main house or as separate living space, she-shed, man-cave, studio, work out room or home office. Roof replaced in 2016. Exposed beam ceilings in kitchen and dining areas. For those familiar with the 'Sunshine Homes' in KW, you know they were built with crawl spaces between the ground & the floor, taller attics w/ pull-down stairs, beautiful hard wood floors & asbestos siding. Most of main house still has original hard wood floors & the cottage has bamboo flooring. Sellers say interior of house did not flood during Wilma. 3712 Duck affords you yard space, room for pool, carport with additional off-street parking & one of KW's most desirable New Town neighborhoods. Convenient location is close to schools, shopping, theaters, medical offices, ball fields, beach, airport, golf course & hospital. Just a short ride into Old Town & world-famous Duval St.. Make your next home at 3712 Duck Ave!

3712 Duck Ave, Key West

$1,699,000

Experience the best of Key West living at 809 Washington Street #102, located in the exclusive Casa Marina neighborhood. This exquisite 3-story townhome offers a 3-bedroom, 3.5-bath residence (sleeps 8-10) showcasing nearly 1,800 sq ft of sophisticated island style, featuring high-end finishes, bright open living spaces, a gourmet kitchen with stainless steel Viking appliances, seamless indoor-outdoor living, and one deeded parking space. Relax in your own private tropical oasis, complete with a heated pool and lush landscaping, perfect for entertaining and unwinding in paradise. With only a short walk to the beach, restaurants, famous Duval Street and entertainment, 809 Washington offers the perfect blend of island luxury and walkable Key West living and adventures.

3 Beds ⋅ 4 Baths ⋅ 620477 MLS

Experience the best of Key West living at 809 Washington Street #102, located in the exclusive Casa Marina neighborhood. This exquisite 3-story townhome offers a 3-bedroom, 3.5-bath residence (sleeps 8-10) showcasing nearly 1,800 sq ft of sophisticated island style, featuring high-end finishes, bright open living spaces, a gourmet kitchen with stainless steel Viking appliances, seamless indoor-outdoor living, and one deeded parking space. Relax in your own private tropical oasis, complete with a heated pool and lush landscaping, perfect for entertaining and unwinding in paradise. With only a short walk to the beach, restaurants, famous Duval Street and entertainment, 809 Washington offers the perfect blend of island luxury and walkable Key West living and adventures.

809 Washington St Unit # 102, Key West

$1,450,000

There is almost nothing like this in Key West: a 2007-built home, raised from the ground up to modern standards. Rare, move-in ready, and free of the surprises that come with much older homes in town. Elevated above the floodplain, with impact windows and doors rated for 175 mph winds and a 16kW standby generator, this is a home built for real peace of mind, whether you are here year-round or away for the summer. Inside, vaulted ceilings soar over travertine floors, granite counters, and stainless steel appliances, including a gas range, set off by warm custom cabinetry. The primary bedroom has a roomy walk-in closet and a spa-style stone shower. Then there is the outside, private, and tropical. Picture morning coffee by the saltwater pool and easy evenings under the covered gazebo, eight around the table with plenty of room for the grilling enthusiast. A wide composite deck and an outdoor shower to rinse off after a swim round out the space. Three bedrooms, two baths, and storage you will actually use: a floored, air-conditioned attic plus generous space under the house. A covered double driveway adds to the everyday convenience. This is the Key West home you have been waiting for.

3 Beds ⋅ 2 Baths ⋅ 620448 MLS

There is almost nothing like this in Key West: a 2007-built home, raised from the ground up to modern standards. Rare, move-in ready, and free of the surprises that come with much older homes in town. Elevated above the floodplain, with impact windows and doors rated for 175 mph winds and a 16kW standby generator, this is a home built for real peace of mind, whether you are here year-round or away for the summer. Inside, vaulted ceilings soar over travertine floors, granite counters, and stainless steel appliances, including a gas range, set off by warm custom cabinetry. The primary bedroom has a roomy walk-in closet and a spa-style stone shower. Then there is the outside, private, and tropical. Picture morning coffee by the saltwater pool and easy evenings under the covered gazebo, eight around the table with plenty of room for the grilling enthusiast. A wide composite deck and an outdoor shower to rinse off after a swim round out the space. Three bedrooms, two baths, and storage you will actually use: a floored, air-conditioned attic plus generous space under the house. A covered double driveway adds to the everyday convenience. This is the Key West home you have been waiting for.

2313 Fogarty Ave, Key West

$2,385,000

Limited time buyer incentive - as an added bonus, the sale now includes a low-mile 2021 Jeep Wrangler Sahara Convertible--giving you the complete Key West lifestyle with the perfect island ride from day one. Welcome to your quintessential Old Town retreat, where classic Key West character has been thoughtfully restored into a warm, inviting home designed for easy island living. This entire property has undergone substantial renovations & a comprehensive transformation. Beautifully reimagined & built for entertaining, the now 3-bedroom, 3.5-bath residence boasts nearly 1,900 sq ft of effortless indoor-outdoor living with every bedroom featuring its own en suite bath including an optional first-floor primary suite. Beneath a magnificent Royal Poinciana tree, the inviting front porch opens to bright, airy living spaces accented by white pine floors and a seamless flow designed for entertaining. The chef's kitchen showcases natural oak shaker cabinetry, Calacatta Miraggio Gold quartz countertops, Bertazzoni appliances, a Dade County Pine accent wall, and timeless finishes that blend warmth with sophistication. French doors lead to a private tropical oasis featuring Ipe hardwood decking, a newly rebuilt saltwater pool and spa, and lush, low-maintenance native landscaping. Upstairs, an expansive wraparound balcony overlooks a mature fruit-bearing mango tree--an unmistakable touch of Old Town charm. Additional highlights include off-street parking, the coveted X Flood Zone, and designer furnishings throughout, allowing for an effortless, move-in-ready experience. Ideally located just one block from vibrant White Street and a short walk or bike ride to the beach, Duval Street, restaurants, galleries, and waterfront attractions, this exceptional property is equally suited as a private island retreat, luxury vacation rental, or full-time residence.

3 Beds ⋅ 4 Baths ⋅ 620437 MLS

Limited time buyer incentive - as an added bonus, the sale now includes a low-mile 2021 Jeep Wrangler Sahara Convertible--giving you the complete Key West lifestyle with the perfect island ride from day one. Welcome to your quintessential Old Town retreat, where classic Key West character has been thoughtfully restored into a warm, inviting home designed for easy island living. This entire property has undergone substantial renovations & a comprehensive transformation. Beautifully reimagined & built for entertaining, the now 3-bedroom, 3.5-bath residence boasts nearly 1,900 sq ft of effortless indoor-outdoor living with every bedroom featuring its own en suite bath including an optional first-floor primary suite. Beneath a magnificent Royal Poinciana tree, the inviting front porch opens to bright, airy living spaces accented by white pine floors and a seamless flow designed for entertaining. The chef's kitchen showcases natural oak shaker cabinetry, Calacatta Miraggio Gold quartz countertops, Bertazzoni appliances, a Dade County Pine accent wall, and timeless finishes that blend warmth with sophistication. French doors lead to a private tropical oasis featuring Ipe hardwood decking, a newly rebuilt saltwater pool and spa, and lush, low-maintenance native landscaping. Upstairs, an expansive wraparound balcony overlooks a mature fruit-bearing mango tree--an unmistakable touch of Old Town charm. Additional highlights include off-street parking, the coveted X Flood Zone, and designer furnishings throughout, allowing for an effortless, move-in-ready experience. Ideally located just one block from vibrant White Street and a short walk or bike ride to the beach, Duval Street, restaurants, galleries, and waterfront attractions, this exceptional property is equally suited as a private island retreat, luxury vacation rental, or full-time residence.

1033 Catherine St, Key West

$915,000

Welcome to 2317 Fogarty Avenue, a beautifully updated 3-bedroom, 2-bathroom home ideally located in the heart of Key West. Combining modern upgrades with island charm, this centrally located residence offers comfortable living just minutes from beaches, shopping, dining, schools, and all that Key West has to offer. The updated kitchen features elegant porcelain countertops, Café appliances, and a newly installed range hood. Recent improvements include a new metal roof (2025) and A/C coils replaced in 2026, providing added peace of mind. An added bonus is the spacious attic, offering valuable storage space--a rare and highly desirable feature in Key West. Step outside to a spacious backyard with mature banana trees, plenty of room to add a pool, and space to create your own private island oasis. A double driveway provides ample off-street parking. Whether you're searching for a full-time residence, a second home, or an investment opportunity, this move-in-ready property offers the perfect blend of comfort, convenience, and island living. Owner is a licensed Florida real estate agent.

3 Beds ⋅ 2 Baths ⋅ 620435 MLS

Welcome to 2317 Fogarty Avenue, a beautifully updated 3-bedroom, 2-bathroom home ideally located in the heart of Key West. Combining modern upgrades with island charm, this centrally located residence offers comfortable living just minutes from beaches, shopping, dining, schools, and all that Key West has to offer. The updated kitchen features elegant porcelain countertops, Café appliances, and a newly installed range hood. Recent improvements include a new metal roof (2025) and A/C coils replaced in 2026, providing added peace of mind. An added bonus is the spacious attic, offering valuable storage space--a rare and highly desirable feature in Key West. Step outside to a spacious backyard with mature banana trees, plenty of room to add a pool, and space to create your own private island oasis. A double driveway provides ample off-street parking. Whether you're searching for a full-time residence, a second home, or an investment opportunity, this move-in-ready property offers the perfect blend of comfort, convenience, and island living. Owner is a licensed Florida real estate agent.

2317 Fogarty Ave, Key West

$985,000

Discover the timeless charm of Key West living at 1222 Florida Street, ideally positioned in the highly sought-after White Street Gallery District. Just a short stroll from Higgs Beach, the White Street Pier, neighborhood parks, tennis and pickleball courts, and less than a mile from the restaurants, boutiques, galleries, and nightlife of iconic Duval Street, this location offers the perfect balance of tranquility and convenience. Offering approximately 1,580 square feet of living space, the residence features an inviting floor plan filled with natural light and comfortable gathering spaces designed for everyday living and effortless entertaining. Spacious bedrooms and flexible living areas provide versatility for a primary residence, seasonal escape, or investment property. With 2 bedrooms and 1 bathroom on the first floor and a huge loft room upstairs. Outdoor living is an essential part of the island lifestyle, and this property offers the opportunity to create your own private tropical oasis with room to add a pool or simply bring your furniture and enjoy the privacy with a fully fenced yard and off street parking. The surrounding neighborhood is celebrated for its tree-lined streets, historic charm, vibrant arts community, and exceptional walkability. Spend your mornings biking to the beach, afternoons exploring local galleries and evenings enjoying world-class dining! Located in a 28-day rental zoning.

3 Beds ⋅ 1 Baths ⋅ 620399 MLS

Discover the timeless charm of Key West living at 1222 Florida Street, ideally positioned in the highly sought-after White Street Gallery District. Just a short stroll from Higgs Beach, the White Street Pier, neighborhood parks, tennis and pickleball courts, and less than a mile from the restaurants, boutiques, galleries, and nightlife of iconic Duval Street, this location offers the perfect balance of tranquility and convenience. Offering approximately 1,580 square feet of living space, the residence features an inviting floor plan filled with natural light and comfortable gathering spaces designed for everyday living and effortless entertaining. Spacious bedrooms and flexible living areas provide versatility for a primary residence, seasonal escape, or investment property. With 2 bedrooms and 1 bathroom on the first floor and a huge loft room upstairs. Outdoor living is an essential part of the island lifestyle, and this property offers the opportunity to create your own private tropical oasis with room to add a pool or simply bring your furniture and enjoy the privacy with a fully fenced yard and off street parking. The surrounding neighborhood is celebrated for its tree-lined streets, historic charm, vibrant arts community, and exceptional walkability. Spend your mornings biking to the beach, afternoons exploring local galleries and evenings enjoying world-class dining! Located in a 28-day rental zoning.

1222 Florida St, Key West

$3,800,000

First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premier streets. Located in the desirable X flood zone, the property features three bedrooms, three baths, and off-street parking for two vehicles. Rich in character and timeless Key West architecture, the home showcases beautifully white-painted, Dade County pine floors and walls, crown molding, and an open-concept living space. Dramatic cathedral ceilings in the living and dining areas create an airy, expansive atmosphere filled with natural light. The main residence offers excellent storage with multiple closets, two spacious bedrooms each with a private en-suite bath, a dedicated library/office, and a separate utility room. True to classic indoor-outdoor island living, French doors open from nearly every room, leading to a private oasis designed for entertaining. The backyard features a private 26' x 11' heated pool accented by dual waterfalls, a gas fire pit, an outdoor shower, and an expansive patio surrounded by lush landscaping. Enjoy the large, comfortable covered porch, perfect for enjoying coffee and the morning paper or an afternoon nap. Guests will be delighted to stay in the detached cottage with ample closet space and a beautifully appointed bath finished with floor-to-ceiling glass tile. Thoughtfully designed, the bath offers dual access--one entrance from the bedroom and another directly from the patio--making it an ideal pool bath. Adding to the property's charm is a lighted turf area with an added surprise, perfect for large parties and room for the kids or pets to play. Relax on the front porch, currently separated from the back porch by a privacy wall. With a small extension, the home's original wraparound design can be fully restored. This extraordinary opportunity to own a classic period home in the heart of Old Town is not to be missed. Call today to schedule your private showing.

3 Beds ⋅ 3 Baths ⋅ 620343 MLS

First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premier streets. Located in the desirable X flood zone, the property features three bedrooms, three baths, and off-street parking for two vehicles. Rich in character and timeless Key West architecture, the home showcases beautifully white-painted, Dade County pine floors and walls, crown molding, and an open-concept living space. Dramatic cathedral ceilings in the living and dining areas create an airy, expansive atmosphere filled with natural light. The main residence offers excellent storage with multiple closets, two spacious bedrooms each with a private en-suite bath, a dedicated library/office, and a separate utility room. True to classic indoor-outdoor island living, French doors open from nearly every room, leading to a private oasis designed for entertaining. The backyard features a private 26' x 11' heated pool accented by dual waterfalls, a gas fire pit, an outdoor shower, and an expansive patio surrounded by lush landscaping. Enjoy the large, comfortable covered porch, perfect for enjoying coffee and the morning paper or an afternoon nap. Guests will be delighted to stay in the detached cottage with ample closet space and a beautifully appointed bath finished with floor-to-ceiling glass tile. Thoughtfully designed, the bath offers dual access--one entrance from the bedroom and another directly from the patio--making it an ideal pool bath. Adding to the property's charm is a lighted turf area with an added surprise, perfect for large parties and room for the kids or pets to play. Relax on the front porch, currently separated from the back porch by a privacy wall. With a small extension, the home's original wraparound design can be fully restored. This extraordinary opportunity to own a classic period home in the heart of Old Town is not to be missed. Call today to schedule your private showing.

619 Ashe St, Key West

$2,999,000

1627 Johnson St. -- A Legacy of Design, A Life Fully Lived. Some homes reveal themselves slowly -- and this is one of them. Designed by the late Michael Ingram, one of Key West's most celebrated architects, this was his final project and, for three years, his own home. He built it the way he lived -- with intention, precision, and an uncompromising commitment to quality that no passing glance from the street could convey. Step through the gate and the story becomes immediately clear. Completed in 2019 on an oversized 7,200-square-foot corner lot, the residence is enclosed by solid concrete walls that create a world entirely apart -- private, lush, and serene. Soaring vaulted ceilings, white oak floors, and six skylights flood the open living spaces with natural light. Impact-rated windows and doors, automatic electric blinds throughout, and a built-in generator ensure effortless comfort in every season. The kitchen features a gas stove, custom cabinetry, and a butler's pantry. The primary suite is finished in deep charcoal tones with an oversized shower. The current owner layered Ingram's architecture with a fearless, joyful personality entirely their own -- designer wallpaper in sweeping hues of hot pink crowns the guest room ceiling, setting the tone for interiors that are bold, tropical, and entirely alive. Offered fully furnished and move-in ready. Outside, the resort-style experience unfolds across an elevated pool with an infinity-edge waterfall, in-pool lounge chairs, and a bespoke weatherproof TV enclosure -- custom-designed to open automatically so you never have to leave the water. The surrounding IPE hardwood deck, prized for its density and natural resistance to the elements, frames it all beautifully. Mature palms, lush tropical plantings, a covered two-car carport, and a detached one-bedroom guest house -- ideal for visitors, rental income, or a private office -- complete a property that simply cannot be appreciated from the street.

3 Beds ⋅ 4 Baths ⋅ 620286 MLS

1627 Johnson St. -- A Legacy of Design, A Life Fully Lived. Some homes reveal themselves slowly -- and this is one of them. Designed by the late Michael Ingram, one of Key West's most celebrated architects, this was his final project and, for three years, his own home. He built it the way he lived -- with intention, precision, and an uncompromising commitment to quality that no passing glance from the street could convey. Step through the gate and the story becomes immediately clear. Completed in 2019 on an oversized 7,200-square-foot corner lot, the residence is enclosed by solid concrete walls that create a world entirely apart -- private, lush, and serene. Soaring vaulted ceilings, white oak floors, and six skylights flood the open living spaces with natural light. Impact-rated windows and doors, automatic electric blinds throughout, and a built-in generator ensure effortless comfort in every season. The kitchen features a gas stove, custom cabinetry, and a butler's pantry. The primary suite is finished in deep charcoal tones with an oversized shower. The current owner layered Ingram's architecture with a fearless, joyful personality entirely their own -- designer wallpaper in sweeping hues of hot pink crowns the guest room ceiling, setting the tone for interiors that are bold, tropical, and entirely alive. Offered fully furnished and move-in ready. Outside, the resort-style experience unfolds across an elevated pool with an infinity-edge waterfall, in-pool lounge chairs, and a bespoke weatherproof TV enclosure -- custom-designed to open automatically so you never have to leave the water. The surrounding IPE hardwood deck, prized for its density and natural resistance to the elements, frames it all beautifully. Mature palms, lush tropical plantings, a covered two-car carport, and a detached one-bedroom guest house -- ideal for visitors, rental income, or a private office -- complete a property that simply cannot be appreciated from the street.

1627 Johnson St, Key West

$1,799,765

Discover the perfect blend of island charm, comfort, and versality in this exceptional Key West property featuring a main residence and a spacious guest house. The main home offers 2 bed, and 2 baths thoughtfully designed with bright, open living space and classic Key West character. Added value is the separate guest house featuring an open concept floor plan, a beautiful bathroom, with open first floor bedroom, and an additional sleeping area on the second floor overlook that accommodates up to six guests. Perfect for the extended family/friends, or income producing opportunities, this flexible space offers endless possibilities. End your day with a relaxing swim in your inground 15x15 pool while looking at the stars.

3 Beds ⋅ 3 Baths ⋅ 620197 MLS

Discover the perfect blend of island charm, comfort, and versality in this exceptional Key West property featuring a main residence and a spacious guest house. The main home offers 2 bed, and 2 baths thoughtfully designed with bright, open living space and classic Key West character. Added value is the separate guest house featuring an open concept floor plan, a beautiful bathroom, with open first floor bedroom, and an additional sleeping area on the second floor overlook that accommodates up to six guests. Perfect for the extended family/friends, or income producing opportunities, this flexible space offers endless possibilities. End your day with a relaxing swim in your inground 15x15 pool while looking at the stars.

1523 Seminary St, Key West

$1,799,000

There is something special about a home where everything has already been done for you, and at 2101 Harris Avenue, all that is left is to move in and start enjoying it! Completely reimagined from top to bottom in 2025, this beautifully renovated Midtown East home feels fresh, welcoming, and ready for its next chapter. Set on a fully fenced corner lot with all new landscaping, the property offers both privacy and convenience, just minutes from schools, restaurants, shopping, and everything that makes Key West so special. Inside, sunlight fills the home through impact windows and doors, filling the home with a bright and airy feel. At the center of it all is a beautifully designed kitchen, where a large island with waterfall quartz counters comfortably seats 4 and naturally becomes the place where family and friends gather. From there, everything flows effortlessly outdoors. Large entertaining spaces connect beautifully to the covered rear porch and pool area, making the home feel bigger, brighter, and built for gathering. Whether it is dinner with friends, a lazy afternoon by the water, or simply enjoying the view from inside, the connection between indoor and outdoor living feels natural and easy. The heated pool, complete with a shallow sun shelf, becomes the centerpiece of the backyard, surrounded by generous space for lounging and outdoor dining. The 3 bedroom, 2.5 bathroom layout is equally inviting, highlighted by a spacious primary suite featuring a large walk in closet and private balcony. Beautifully renovated and thoughtfully designed, this is a home ready to be enjoyed from day one.

3 Beds ⋅ 3 Baths ⋅ 620176 MLS

There is something special about a home where everything has already been done for you, and at 2101 Harris Avenue, all that is left is to move in and start enjoying it! Completely reimagined from top to bottom in 2025, this beautifully renovated Midtown East home feels fresh, welcoming, and ready for its next chapter. Set on a fully fenced corner lot with all new landscaping, the property offers both privacy and convenience, just minutes from schools, restaurants, shopping, and everything that makes Key West so special. Inside, sunlight fills the home through impact windows and doors, filling the home with a bright and airy feel. At the center of it all is a beautifully designed kitchen, where a large island with waterfall quartz counters comfortably seats 4 and naturally becomes the place where family and friends gather. From there, everything flows effortlessly outdoors. Large entertaining spaces connect beautifully to the covered rear porch and pool area, making the home feel bigger, brighter, and built for gathering. Whether it is dinner with friends, a lazy afternoon by the water, or simply enjoying the view from inside, the connection between indoor and outdoor living feels natural and easy. The heated pool, complete with a shallow sun shelf, becomes the centerpiece of the backyard, surrounded by generous space for lounging and outdoor dining. The 3 bedroom, 2.5 bathroom layout is equally inviting, highlighted by a spacious primary suite featuring a large walk in closet and private balcony. Beautifully renovated and thoughtfully designed, this is a home ready to be enjoyed from day one.

2101 Harris Ave, Key West

$1,300,000

Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ultimate relaxation. This timeless Conch Cottage is nestled in a secure gated compound of six Key West Style Cottages. Low HOA Fee $288 Monthly includes Pool and Landscaping maintenance. This home is in an X500 Flood Zone, Banks do not require Flood Insurance. Situated in the highly coveted Old Town North neighborhood, this home is in the heart of everything quintessentially Key West. Revel in the exquisite architecture, savor the diverse culinary delights, explore unique boutiques, and immerse yourself in the vibrant nightlife and rich cultural scene just a leisurely stroll from your doorstep. Just four blocks to the Historic Seaport and across from the iconic Five Brothers Coffee Shop. The renovated Living Room, Dining Room, and Kitchen features classic Vaulted Wood Ceilings, and Hard Wood Flooring. The renovated Modern Bathroom also features a Vaulted Wood Ceiling, and a spacious Glass and Tile Walk-In Shower, Custom Lighting, Custom Sink-Vanity, and Custom Mirrors. The lovely, renovated Kitchen features Stainless Steel Appliances, Custom Wood Cabinets, and a Custom Ceiling Fan-Light fixture. A spacious Covered and Screened Wood Accented Patio area connects the Main 2 Bedroom - 1 Bathroom Cottage to the adjoining Studio 1 Bedroom - 1 Bathroom separate living area. The Studio has a New AC Unit, Refrigerator, Microwave Oven, and an Air Fryer Oven. The Studio Bathroom has also been renovated with a Modern Glass and Tile Walk-In Shower, Custom Sink, Custom Lighted Mirror, and Custom Lighting. Both living areas have their own separate and private door entrances. Excellent Rental Income opportunity. This ideal 3BR-2BA floor plan can accommodate the owner living in one side, while renting the other side. Paradise Awaits in Old Town North Key West.

3 Beds ⋅ 2 Baths ⋅ 620150 MLS

Embrace the enchantment of Old Key West Charm in this Beautifully Updated Historic Conch 3 Bedroom-2 Bath Home, featuring a Tropical Landscaped community Pool creating ultimate relaxation. This timeless Conch Cottage is nestled in a secure gated compound of six Key West Style Cottages. Low HOA Fee $288 Monthly includes Pool and Landscaping maintenance. This home is in an X500 Flood Zone, Banks do not require Flood Insurance. Situated in the highly coveted Old Town North neighborhood, this home is in the heart of everything quintessentially Key West. Revel in the exquisite architecture, savor the diverse culinary delights, explore unique boutiques, and immerse yourself in the vibrant nightlife and rich cultural scene just a leisurely stroll from your doorstep. Just four blocks to the Historic Seaport and across from the iconic Five Brothers Coffee Shop. The renovated Living Room, Dining Room, and Kitchen features classic Vaulted Wood Ceilings, and Hard Wood Flooring. The renovated Modern Bathroom also features a Vaulted Wood Ceiling, and a spacious Glass and Tile Walk-In Shower, Custom Lighting, Custom Sink-Vanity, and Custom Mirrors. The lovely, renovated Kitchen features Stainless Steel Appliances, Custom Wood Cabinets, and a Custom Ceiling Fan-Light fixture. A spacious Covered and Screened Wood Accented Patio area connects the Main 2 Bedroom - 1 Bathroom Cottage to the adjoining Studio 1 Bedroom - 1 Bathroom separate living area. The Studio has a New AC Unit, Refrigerator, Microwave Oven, and an Air Fryer Oven. The Studio Bathroom has also been renovated with a Modern Glass and Tile Walk-In Shower, Custom Sink, Custom Lighted Mirror, and Custom Lighting. Both living areas have their own separate and private door entrances. Excellent Rental Income opportunity. This ideal 3BR-2BA floor plan can accommodate the owner living in one side, while renting the other side. Paradise Awaits in Old Town North Key West.

611 Grinnell St Unit 4, Key West

$1,999,999

Tucked into the heart of Old Town, this beautifully restored residence pairs Key West's historic character with thoughtful modern updates--all just one block off Duval Street and three blocks from the iconic Southernmost Point. Taken down to the studs and fully renovated in 2018, the three-bedroom, two-bath home delivers high-end finishes throughout, plus the rare bonuses of a private gated courtyard and off-street parking. The layout is built for easy island living, blurring the line between indoors and out. Refined touches run throughout: impact-rated doors and windows, rich oak floors, custom tilework, and original Dade County Pine that's been carefully preserved. At the center of it all, the kitchen is made for entertaining, with stainless appliances, brushed marble counters, and eye-catching copper and bronze fixtures. The generously sized primary suite is a true retreat--vaulted cypress ceilings, a spa-inspired en suite, a showpiece copper soaking tub, and custom closets with room to spare. Add in abundant storage and easy-care landscaping, and the practical details are covered too. For buyers chasing style, comfort, and true walkability in one of Key West's most sought-after neighborhoods, this one belongs at the top of the list.

3 Beds ⋅ 2 Baths ⋅ 620106 MLS

Tucked into the heart of Old Town, this beautifully restored residence pairs Key West's historic character with thoughtful modern updates--all just one block off Duval Street and three blocks from the iconic Southernmost Point. Taken down to the studs and fully renovated in 2018, the three-bedroom, two-bath home delivers high-end finishes throughout, plus the rare bonuses of a private gated courtyard and off-street parking. The layout is built for easy island living, blurring the line between indoors and out. Refined touches run throughout: impact-rated doors and windows, rich oak floors, custom tilework, and original Dade County Pine that's been carefully preserved. At the center of it all, the kitchen is made for entertaining, with stainless appliances, brushed marble counters, and eye-catching copper and bronze fixtures. The generously sized primary suite is a true retreat--vaulted cypress ceilings, a spa-inspired en suite, a showpiece copper soaking tub, and custom closets with room to spare. Add in abundant storage and easy-care landscaping, and the practical details are covered too. For buyers chasing style, comfort, and true walkability in one of Key West's most sought-after neighborhoods, this one belongs at the top of the list.

1119 Whitehead St, Key West

$930,000

*Seller Motivated, told us to bring all reasonable Offers. 3/1 with a guest cottage/office space at rear of property with private full bath and kitchenette. 4/2 with cottage. All just awaiting a Buyers personal taste!. Huge lot with incredible area for big a beautiful pool! This is a perfect family 3/1 home in one of the best New Town neighborhoods. This fully gated home sits on a massive 7000 sf oversized lot and is completely move-in ready. The home boasts three bedrooms and one bath. The floor plan in the kitchen and living area flows perfectly for open living. Glass French doors open to the back patio (that could be enclosed for Florida room) and look out at the massive green lawn and native trees. The large back yard is perfect for expansion or creating your very own tropical oasis. Set back in complete privacy is a beautiful guest suite/office space with bath. The side yard with an additional privacy fence is perfect boat parking. This property is a must see! Occupied so must allow 24 hour notice.

3 Beds ⋅ 2 Baths ⋅ 620104 MLS

*Seller Motivated, told us to bring all reasonable Offers. 3/1 with a guest cottage/office space at rear of property with private full bath and kitchenette. 4/2 with cottage. All just awaiting a Buyers personal taste!. Huge lot with incredible area for big a beautiful pool! This is a perfect family 3/1 home in one of the best New Town neighborhoods. This fully gated home sits on a massive 7000 sf oversized lot and is completely move-in ready. The home boasts three bedrooms and one bath. The floor plan in the kitchen and living area flows perfectly for open living. Glass French doors open to the back patio (that could be enclosed for Florida room) and look out at the massive green lawn and native trees. The large back yard is perfect for expansion or creating your very own tropical oasis. Set back in complete privacy is a beautiful guest suite/office space with bath. The side yard with an additional privacy fence is perfect boat parking. This property is a must see! Occupied so must allow 24 hour notice.

1227 20th, Key West

$2,499,000

Stunning modern home in New Town offering 2,525 sq. ft. of beautifully designed living space on an 8,250 sq. ft. lot. This 3-bedroom, 2 full + 2 half bath home features a desirable split floor plan with a private primary suite, complete with a walk-through closet and spa-like ensuite bath, plus two guest bedrooms and a full bath. The open-concept living, dining, and kitchen area is ideal for entertaining, highlighted by a 15-ft island and high-end Viking stainless steel appliances. The chef's kitchen also includes a wine cooler, ice maker, warming drawer, dual beverage drawers, and a dedicated coffee/wine station. Additional features include a walk-in pantry with drop-down desk, separate laundry room, and convenient half bath. Outdoor living is just as impressive, with French doors opening to a private backyard oasis featuring an Ipe wood deck, outdoor kitchen, outdoor shower, and an air-conditioned half bath. Enjoy the large heated pool and spa surrounded by lush landscaping. The property also offers a covered dual carport with built-in storage and additional brick parking for guests. Located just down the road from a public boat ramp and perfect for sunrise and sunset walks.

3 Beds ⋅ 4 Baths ⋅ 620092 MLS

Stunning modern home in New Town offering 2,525 sq. ft. of beautifully designed living space on an 8,250 sq. ft. lot. This 3-bedroom, 2 full + 2 half bath home features a desirable split floor plan with a private primary suite, complete with a walk-through closet and spa-like ensuite bath, plus two guest bedrooms and a full bath. The open-concept living, dining, and kitchen area is ideal for entertaining, highlighted by a 15-ft island and high-end Viking stainless steel appliances. The chef's kitchen also includes a wine cooler, ice maker, warming drawer, dual beverage drawers, and a dedicated coffee/wine station. Additional features include a walk-in pantry with drop-down desk, separate laundry room, and convenient half bath. Outdoor living is just as impressive, with French doors opening to a private backyard oasis featuring an Ipe wood deck, outdoor kitchen, outdoor shower, and an air-conditioned half bath. Enjoy the large heated pool and spa surrounded by lush landscaping. The property also offers a covered dual carport with built-in storage and additional brick parking for guests. Located just down the road from a public boat ramp and perfect for sunrise and sunset walks.

1511 17th Ter, Key West

$1,245,000

Beautifully maintained Golf Club home overlooking the 17th hole in the Sanctuary. This home is located on one of the largest lots in the development. New flooring upstairs, a new cooktop stove, a new kitchen sink, new light fixtures, and freshly painted exterior within the past 3 years. The home features a private carport for two vehicles and a detached storage unit. The Key West Golf Club community features two gorgeous pools surrounded by lush tropical landscaping, a gym at the clubhouse, on-site security and managers. Property is currently being leased.

3 Beds ⋅ 3 Baths ⋅ 620031 MLS

Beautifully maintained Golf Club home overlooking the 17th hole in the Sanctuary. This home is located on one of the largest lots in the development. New flooring upstairs, a new cooktop stove, a new kitchen sink, new light fixtures, and freshly painted exterior within the past 3 years. The home features a private carport for two vehicles and a detached storage unit. The Key West Golf Club community features two gorgeous pools surrounded by lush tropical landscaping, a gym at the clubhouse, on-site security and managers. Property is currently being leased.

243 Golf Club Dr, Key West

$1,249,000

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'll love the charming curb appeal, spacious covered front porch, and bright, airy interior filled with natural light. The heart of the home is the stunning chef's kitchen featuring an oversized quartz island, custom white shaker cabinetry, stainless steel appliances, abundant storage, and sleek designer finishes throughout. The open-concept layout flows seamlessly into the living and dining areas, making it ideal for entertaining and everyday living. The bedrooms offer comfort and flexibility, and both bathrooms have been thoughtfully updated with clean, modern touches. Located in a desirable neighborhood close to schools, shopping, dining, and local amenities, this move-in-ready home offers the perfect combination of style, comfort, and functionality.

3 Beds ⋅ 2 Baths ⋅ 620013 MLS

Welcome to this beautifully renovated 3-bedroom, 2-bathroom home that perfectly blends modern finishes with warm, inviting living spaces. From the moment you arrive, you'll love the charming curb appeal, spacious covered front porch, and bright, airy interior filled with natural light. The heart of the home is the stunning chef's kitchen featuring an oversized quartz island, custom white shaker cabinetry, stainless steel appliances, abundant storage, and sleek designer finishes throughout. The open-concept layout flows seamlessly into the living and dining areas, making it ideal for entertaining and everyday living. The bedrooms offer comfort and flexibility, and both bathrooms have been thoughtfully updated with clean, modern touches. Located in a desirable neighborhood close to schools, shopping, dining, and local amenities, this move-in-ready home offers the perfect combination of style, comfort, and functionality.

2116 Fogarty Ave, Key West

$3,500,000

Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

3 Beds ⋅ 3 Baths ⋅ 619959 MLS

Located within the quiet, gated security of Old Town Villas, this 3-bedroom, 3-bathroom townhome offers a sophisticated, low-maintenance island retreat just one block off of Duval St. Built in 2017, with solid concrete construction, this exceptional residence blends contemporary elegance with a thoughtfully designed layout that maximizes privacy, comfort, and functionality. Stepping inside, the interior is highlighted by beautiful tile flooring that runs seamlessly throughout. The main level features an open-concept layout with a spacious living room and chef's kitchen complete with stainless steel appliances and granite peninsula offering abundant prep space and casual seating. Just off the kitchen, a flexible-use room can serve as a dining area or private bedroom suite, complete with its own ensuite bathroom. A hallmark of this property is the extensive amount of premium, custom-built cabinetry and shelving installed throughout by the California Closets, offering unparalleled storage and organization. For effortless luxury, a private elevator services all four levels, transporting you from the two-car garage all the way to the rooftop terrace. The third floor hosts two spacious ensuite bedrooms, each featuring private balconies and large walk-in closets complete with custom organizational systems. The top floor is dedicated to an open living room and office area--a flexible bonus space filled with natural light. Step out from this upper lounge onto the spectacular rooftop terrace, equipped with custom awnings for comfortable shade, designed to capture both sunrise serenity and vibrant sunset views. For total peace of mind, the home features impact-rated windows and doors throughout. Beyond your front door, enjoy the exclusive community amenities, including a large pool and cabana. Conveniently situated near the very best dining and boutiques Key West has to offer, this home delivers the ultimate blend of privacy, location and the coveted Key West lifestyle.

141 Simonton St, Key West

Angela Palma

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