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$1,025,000
2 Beds ⋅ 2 Baths ⋅ 620885 MLS
Completely remodeled to the studs in 2024, this exceptional Key West condo is truly turn-key and move in ready. The home has been meticulously maintained and shows beautifully in every detail. Everything in the unit is new, from the finishes and fixtures to the systems. Central air conditioning and a security alarm are already in place for immediate comfort and peace of mind. This 953 sq. ft.unit features an oversized primary bedroom with a true walk-in closet, a spa inspired -large shower with a waterfall showerhead, and high-end details throughout. An additional 195 sq ft covered front porch expands the living space and is protected by premium motorized electronic screens that raise and lower at the touch of a remote-a significant high end upgrade. Located in a desirable three-unit condo association, the HOA fee covers exterior insurance and water, keeping ownership simple and predictable.. Enjoy classic Key West living with lush tropical landscaping including bamboo and a private heated pool. Super clean, super nice, and ready for immediate occupancy.

1116 Truman Ave Unit A, Key West
$1,800,000
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
$875,000
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
$800,000
2 Beds ⋅ 2 Baths ⋅ 620829 MLS
Old Town First floor 2 Bedroom, 2 Bath condo, pool side!. Low HOA- $600 a month/ $1800 a quarter. Great Old Town location, close to Restaurants, '' Walk on White' , Grocery store, and a short walk or bicycle ride to Duval street. This wonderful 2 bedroom, 2 bath condo is one of 4 units and is located steps from the shared pool. Unique to this condo is an outside covered area with a Grill, wet-bar, and seating, exclusively for use with this condo only. Additionally, this condo also has its own washer and dryer. This condo is in a Rental Program, please call listing agent for details. Being sold furnished. This Building has a new roof, and hurricane panels.

906 Truman Ave Unit 2, Key West
$1,400,000
4 Beds ⋅ 2 Baths ⋅ 620808 MLS
This one is a must see! Spacious 4 bedroom, single family in the 'Pearlman Heights' neighborhood of New Town KW that has undergone recent renovations-upgrades. New roof, kitchen, windows (impact rated), on demand water heater, pool pump, Central AC condenser / air handler, light fixtures, ceiling fans, crown molding, interior doors & more. Nice set up for enjoying the KW weather or entertaining because the den, kitchen & dining areas flow out to the pool deck with 32 fl long in ground pool. No interior step downs or tripping hazards. Located on a one-way street with green dividing median on 17th St. Carport covers the off-street parking space plus additional on street parking. Has an exterior 15 X 7 storage / laundry room. Convenient location close to schools, medical offices, grocery stores & shopping, dining, etc..

1105 17th St, Key West
$1,100,000
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
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
$599,000
1 Beds ⋅ 1 Baths ⋅ 620722 MLS
Life feels a little slower in the Casa Marina neighborhood. Mornings begin with a walk to Higgs Beach, afternoons are spent by the pool, and evenings often end just down the street at Salute! on the Beach or Louie's Backyard. Tucked within the peaceful Southpark Condominium community, 816 South Street, Unit 4 places you in the heart of one of Key West's most desirable locations while offering the privacy and simplicity of low maintenance island living. Inside, this 1 bedroom, 1 bathroom condominium feels bright, comfortable, and welcoming. The open living spaces flow naturally to two private outdoor decks, one at the front of the home that is perfect for enjoying the neighborhood atmosphere and another tucked just off the bedroom, surrounded by mature tropical landscaping for a more private escape. The community itself offers the amenities that make everyday living feel like a vacation, including a beautifully maintained heated swimming pool set among lush tropical grounds. An assigned off street parking space and a spacious locked storage area provide conveniences that are increasingly valuable in Key West. Located just 4 blocks from Duval Street, you can easily walk or bike to beaches, restaurants, galleries, shopping, and everything that makes island life so special, while still returning home to one of the quieter residential pockets of Old Town. Whether you are searching for a full time residence, a seasonal retreat, or simply a place where life naturally slows down, 816 South Street, Unit 4 offers an opportunity to experience the very best of Casa Marina living.

816 S St Unit 4, Key West
$1,299,000
7 Beds ⋅ 4 Baths ⋅ 620718 MLS
Investment Opportunity - Income-Producing Triplex! Don't miss this excellent income-producing triplex located in a convenient, high-demand area close to schools, shopping, dining, parks, and just minutes from downtown Key West. Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the others, this property offers outstanding potential. A rare feature of this property is the ample off-street parking, with room for up to 7 vehicles--a highly desirable amenity for both tenants and owners. The flexible layout provides multiple rental opportunities and consistent income potential in a strong rental market. Unit A = 2/1 Unit B = 2/1 Unit C (upstairs) = 3/2 With its desirable location, generous parking, and proven income-producing capabilities, 1614 Dennis Street is an exceptional opportunity for investors or owner-occupants alike. Schedule your private showing today!

1614 Dennis St, Key West
$2,089,000
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
$3,675,000
2 Baths ⋅ 620701 MLS
Rare chance to own a piece of the most iconic street in the Florida Keys. This turn-key commercial building at 1215 Duval Street is offered at a 7.0% cap rate with a solid, established long-time successful restaurant as the tenant and a lease already in place. (Note: the business is not for sale; the real estate and the income-producing lease are.) Positioned in the heart of Old Town's high-traffic corridor, the property benefits from year-round foot traffic, world-famous Duval Street exposure, and the enduring demand that makes Key West commercial real estate so limited and so coveted. With a dependable tenant and stabilized income from day one, this is a true passive, hands-off investment in one of the strongest small-market commercial locations in the country. Opportunities to acquire well-located Duval Street commercial real estate with an in-place lease and a proven tenant are exceedingly rare. Whether you're a 1031 exchange buyer seeking reliable cash flow or an investor looking to plant roots in paradise, 1215 Duval Street delivers location, income, and long-term upside. Schedule your private showing today.

1215 Duval St, Key West
$550,000
1 Beds ⋅ 1 Baths ⋅ 620692 MLS
Great opportunity to own your own home or have an excellent source of rental income. Currently the least expensive detached residence in Key West. Freshly painted interior and new AC. This renovated one bedroom condo cottage overlooking the large communal pool is just one block to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with only 3 other condos. There are lovely landscaped communal areas with fruit trees, sun decks, lounge chairs and outdoor dining areas.....Recent improvements to the home include a new metal roof, impact windows plus additional storm shutters. The condo has one bedroom, a full bath with shower above, full kitchen and double doors leading to the pool and patio area.

1318 Duncan St Unit 3, Key West
$1,695,000
2 Beds ⋅ 2 Baths ⋅ 620684 MLS
Renovated 2b/2b beauty is close to the heart of Old Town Key West, yet far enough from the maddening crowd. Late-1800s Conch house with detached guest cottage were gutted and restored in 2021. New roof, infrastructure and new state-of-the-art chef's kitchen. Casement windows open to the back garden that has 8 varieties of bananas. And what a fine garden it is: Orchids & herbs & fruit, oh my. Salvaged Dade County pine walls light up with windows galore. A side yard connects the primary residence to the en-suite detached cottage. On-demand hot water heater. Outdoor shower. Hot tub. Off-street parking. Rear garden entrance to property from Havana Lane offers front and back access. Detailed quality throughout makes this A MUST SEE.

907 Frances St, Key West
$1,800,000
4 Beds ⋅ 3 Baths ⋅ 620682 MLS
Wonderful Old Town Meadows home with 4 Bedrooms, 3 Baths, on a nearly 5000 sq ft lot, this property has a separate Guest Cottage, wrap around front porch, lap- pool, and more! Wood flooring throughout, with 2 living areas leading to the kitchen with Italian designed built in cabinetry . The Primary Bedroom is spacious, and has built-in Custom cabinetry. Steps from the kitchen is a lap pool , extensive decking, and lots of room for outside dining and relaxation. The Guest Cottage has a full bathroom, and exposed beam ceilings. The property is completely fenced and feels very private.There is a curb cut already- for potential off street parking. Buyer to verify!

1407 Petronia St, Key West
$4,750,000
6 Beds ⋅ 5 Baths ⋅ 620662 MLS
A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West
$4,750,000
7 Beds ⋅ 5 Baths ⋅ 620661 MLS
A rare opportunity to own one of Key West's most captivating waterfront properties, where history, character, and endless potential come together. Nestled along the historic Trumbo Point waterfront, this remarkable estate has remained in the same family for generations and reflects a rich connection to one of the island's most significant maritime neighborhoods. Thought to have origins dating back to the early 20th century, the property showcases timeless Old Key West charm while offering the space and flexibility rarely found today. The main residence is complemented by a separate guest cottage on an oversized waterfront parcel, creating endless possibilities for multigenerational living, a private family compound, or an exceptional investment opportunity. Located in an area once shaped by the island's cigar industry, railroad expansion, and later the development of the Naval Air Station and Coast Guard facilities, this home sits within a neighborhood that tells the story of Key West's evolution through more than a century of history. From the moment you arrive, you'll appreciate the mature tropical landscape, water access, and the feeling of stepping into a piece of Old Key West. Whether you choose to preserve its historic character, thoughtfully enhance the existing structures, or create your own legacy estate, opportunities like this are exceptionally rare. Waterfront properties with this combination of history, location, size, and family ownership seldom become available. 901 Eisenhower Drive is more than a home--it's an opportunity to own a meaningful piece of Key West's past while creating its next chapter.

901 Eisenhower Dr, Key West
$1,149,000
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
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
$1,350,000
4 Beds ⋅ 5 Baths ⋅ 620612 MLS
THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, and multi-unit flexibility. Atlantic Boulevard has only a handful of true residential opportunities, and this one brings the rare combination of land, pool, and multi-unit upside. Set on an approximately 8,050 square foot lot, this Atlantic-side property offers roughly 2,750 square feet of living area with a flexible multi-unit configuration and a concrete pool anchoring the outdoor space. The existing home would benefit from a major renovation and thoughtful updating for today's standards, creating a compelling opportunity for an investor, owner-user, or buyer with vision. In a market where land is the luxury, the lot itself is a major part of the story. The scale, pool, and layout create the foundation for a refreshed tropical compound, income-producing retreat, or reimagined Key West residence. Located along Atlantic Boulevard, the property is close to beaches, Old Town, Casa Marina, schools, dining, and the everyday ease that makes island living so desirable. Whether held as a long-term income property or transformed into something more polished, 1503 Atlantic Boulevard offers the kind of upside that is increasingly hard to find in Key West.

1503 Atlantic Blvd, Key West
$1,575,000
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
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
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
$725,000
1 Beds ⋅ 1 Baths ⋅ 620493 MLS
''Seaport Sanctuary'' Located within the Land's End compound steps away from the Historic Key West Seaport and Harbor Walk. This 1 bedroom 1 bath conch cottage features an open floor plan with a storage loft, cathedral ceilings and hardwood floors. Nestled down a brick pathway across from the residents only heated pool. Professionally maintained landscaping surrounds this 6 freestanding conch home complex. Call today!

308 Margaret St Unit 3, Key West
$1,050,000
4 Beds ⋅ 2 Baths ⋅ 620461 MLS
Duplex with adjoining commercial lot for sale. Duplex has 1,342 square feet of living space on a 2,841 sq ft lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. The adjoining 2,244 square foot commercial zoned lot would be ideal for one or more food vendor trucks, with excellent visibility and heavy traffic. Make an offer today!

1421-1425 2nd St, Key West
$979,000
4 Beds ⋅ 2 Baths ⋅ 620453 MLS
When value matters, this solid concrete New Town home stands apart with one of the most compelling price-per-square-foot opportunities on the market. Substantial 4-bedroom, 2-bath home featuring a dedicated office, offering an exceptional combination of comfort and functionality. Situated on an expansive 8,448-square-foot corner lot, the property provides 2,111 square feet of living space, two driveways, off-street parking with an attached carport, a Tesla charging station, and ample room to add a pool. Designed for easy living and entertaining, the open-concept kitchen and living area is enhanced by soaring cathedral ceilings with exposed beams and an abundance of large, light-filtering windows that create a bright and inviting atmosphere throughout. A welcoming front porch, set back amongst mature trees, provides the perfect place to relax and unwind. The elevated home features double-pane windows, noise-dampening door improvements, a V-crimp metal roof, and beautiful terrazzo floors that add timeless Key West character. The solid concrete construction offers lasting durability and an excellent foundation to fine-tune and personalize the home to suit your vision. The fully walled property provides privacy and generous outdoor space. With its larger-than-average footprint, oversized corner lot, two driveways, and endless potential for a backyard pool oasis, this home presents an outstanding opportunity to enjoy the very best of Key West living. Whether you're searching for a comfortably sized family home just or a property with the perfect canvas to create your dream home, this opportunity offers exceptional value.

1500 5th St, Key West
$789,000
2 Beds ⋅ 2 Baths ⋅ 620436 MLS
Welcome to Your Own Slice of Paradise! Pack your flip flops and leave your worries at the door! This enchanting Key West gem is ready to make your island dreams a reality! Nestled in the heart of the Conch Republic, 2005 Fogarty Avenue is the kind of home that makes you exhale the moment you arrive.This beautifully updated 2 bedroom, 2 full bath cottage is bursting with Key West charm and curb appeal. From the moment you step inside, you'll fall in love with the character and that unmistakable colorful warmth that only Key West living can deliver. Best of all? It's fully furnished and completely move-in ready. Just bring your toothbrush and your sunscreen, because everything else is already waiting for you.The versatile bonus space offers endless possibilities! Want a home office, guest overflow, art studio, workshop, or your very own private retreat? Step outside and discover the real showstopper: a spacious, lushly landscaped backyard that's practically begging for a sparkling pool 🏊. Whether you envision weekend soirées under the stars, a private tropical oasis, or the ultimate vacation rental income producer, this backyard delivers the canvas. Practical perks? You've got those too. Off-street parking is a rare and treasured luxury in Key West and this property has it. No more circling the block after a long day at the beach. Located just moments from world-famous Duval Street, celebrated dining, vibrant nightlife, the Historic Seaport, and those legendary Key West sunsets 🌅, this property places you at the very center of the island lifestyle while offering a peaceful, private retreat to come home to.✨ Highlights at a Glance: 2 Bedrooms | 2 Full BathsBonus/Flex SpaceFully Furnished & Move-In ReadyUpdated ThroughoutExpansive Backyard with Pool Potential, Off-Street Parking, central Key West Location. If you're searching for a full-time residence, a vacation escape, or a high-demand rental investment, 2005 Fogarty Ave checks all the boxes

2005 Fogarty Ave, Key West
$915,000
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
$3,500,000
5 Beds ⋅ 5 Baths ⋅ 620434 MLS
First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

416 Fleming St, Key West
$799,000
2 Beds ⋅ 2 Baths ⋅ 620402 MLS
Welcome to this charming 2-bedroom, 2-bath Conch house offering 1,216 sq. ft. of comfortable living space in one of Key West's most convenient locations. The home is filled with warmth and character, highlighted by vaulted wood ceilings with exposed beams that create an inviting coastal atmosphere. Natural light pours through the impact windows and full wall of sliding glass doors, while the thoughtful floor plan provides comfortable areas for both everyday living and entertaining. The well-appointed kitchen offers ample cabinetry, generous counter space and bar seating that creates a natural gathering place for family and guests. A dedicated laundry area adds every day convenience, while the home's open and functional layout enhances its comfortable coastal appeal. An inviting Florida Room extends the living area and serves as the perfect connection to the private backyard retreat. Step outside to discover your own massive fenced-in backyard designed for relaxation, featuring lush landscaping, a hot tub and plenty of entertaining space. Centrally located in New Town, you'll enjoy easy access to beaches, shopping, restaurants, schools, and all the attractions that make island living so desirable. Whether you're looking for a full-time residence, seasonal escape, or island investment, this Key West home offers comfort, character and an exceptional location.

3715 Flagler Ave, Key West
$985,000
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