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$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
$2,475,000
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
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
$2,350,000
6 Beds ⋅ 6 Baths ⋅ 620852 MLS
Set within the exclusive enclave of The Sanctuary at Key West Golf Club, this rare offering presents two distinct residences united as one extraordinary parcel -- a configuration unlike anything currently available on the Key West market. Verandas and porches wrap the property, framing sweeping views of the lake and the emerald fairways of the 17th hole, while tiled floors flow throughout both residences, blurring the line between the two homes and the tropical air outside. At the heart of it all, a resort-caliber pool measuring an impressive 12 x 30 feet anchors a 1,500 square foot outdoor terrace, where long tables are set for twelve or more, indoors and out, beneath the Key West sky. With 6 bedrooms and 5.5 bathrooms spread across 2,840 square feet, this dual-residence estate is purpose-built for the multigenerational family, offering the rare gift of togetherness paired with independence -- separate structures for separate households, united by a single spectacular pool deck built for gathering. For the discerning second-home buyer or investor, the dual-dwelling design opens the door to flexible living arrangements or income-generating potential, a configuration increasingly coveted in today's Key West market. This is more than a home -- it is a once-in-a-lifetime opportunity to establish a family legacy on one of Key West's most coveted golf course settings. Here, generations will gather beneath the verandas, celebrate over long tables set for twelve, and watch the sun set over the 17th green. This is Key West living, reimagined for the modern family -- and passed down for generations to come.

287 & 289 Golf Club Dr, 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
$12,500,000
6 Beds ⋅ 7 Baths ⋅ 620770 MLS
A distinguished offering on one of Key West's most coveted private island enclaves, 32 Sunset Key Drive embodies the ease, elegance, and exclusivity of waterfront living. One of the largest custom residences on Sunset Key, this 3,635-square-foot oceanfront estate was conceived by its original owners with an unwavering commitment to craftsmanship, comfort, and detail. Set beside its own private beach, the home features six ensuite bedrooms and seven full baths, creating a refined retreat designed for gracious hosting and effortless relaxation. Inside, coffered wood-paneled ceilings, tumbled marble, and solid oak floors lend depth, texture, and timeless coastal sophistication. Expansive living, dining, and kitchen spaces open naturally to the outdoors, blurring the line between interior comfort and the island's spectacular waterfront setting. Beyond, a custom rock pool with a hot tub and two-story slide evokes the atmosphere of a private resort, while a fully equipped outdoor kitchen, full bath, shower, and laundry facility elevate every gathering with ease and intention. Hop on the five minute ferry ride to your island paradise, enjoy the fabulous spa and dine at the acclaimed restaurant Latitudes. Truly, this is a one of a kind opportunity for the discerning buyer.

32 Sunset, 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
$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
$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
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
$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
$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
$1,699,000
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
$1,850,000
2 Beds ⋅ 2 Baths ⋅ 620470 MLS
Life feels a little different in Casa Marina. The streets are quieter, the homes are beautifully maintained, and everything from the beach to Old Town is just a short walk or bike ride away. Tucked within one of Key West's most desirable neighborhoods, 1115 South Street captures everything people love about living here. Step inside and the home immediately feels open and inviting. Ten foot ceilings, warm Brazilian cherry floors, and an abundance of natural light create spaces that feel both elegant and comfortable. The entire first floor is designed for gathering, anchored by an impressive kitchen with abundant cabinetry, expansive countertops, and high end appliances that make cooking and entertaining equally enjoyable. As beautiful as the interior is, your attention naturally shifts outdoors. French doors open to a private tropical backyard where a large swimming pool, separate hot tub, and coral stone patios with IPE decking create a peaceful setting for relaxing or entertaining. Surrounded by mature landscaping, the backyard feels like your own private retreat. With both bedrooms located upstairs, the home offers a thoughtful separation between everyday living and personal space. The primary suite even enjoys its own balcony overlooking the backyard, providing a quiet place to begin or end the day. Beautifully maintained and thoughtfully designed, this is a home where every detail encourages you to slow down, entertain often, and enjoy the best of Key West living.

1115 South Street, 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
$1,450,000
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
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
$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
$819,000
1 Beds ⋅ 1 Baths ⋅ 620379 MLS
This elegant historic Old Town cottage is a rare offering paired with a highly competitive price. In addition, it is being sold completely turnkey! Sparkling, gallery-like, and filled with natural light, this beautifully renovated Old Town Key West cottage offers the perfect blend of charm, privacy, and modern comfort. Tucked away on a quiet one-way street, this tropical retreat is just a short stroll to Cafe Sole, Little Pearl, Fausto's Food Palace, local bakeries, and charming boutiques. Renovated down to the studs, the home features vaulted ceilings and an open-concept layout where the gourmet kitchen, entertainment bar, and living area come together to create a bright, welcoming gathering space. True to the Key West lifestyle, an expansive sliding glass door opens to a serene tropical oasis framed by lush fig vines, Spanish lime trees, swaying palms, and a majestic Royal Poinciana tree, where morning coffee, afternoon cocktails, and evenings under the stars become part of everyday life. The property also offers dedicated off-street golf cart parking, potential for a small pool, and no HOA fees, further enhancing its appeal as a private sanctuary. Thoughtfully selected upscale finishes include solid teak flooring, granite countertops, and a beautifully appointed Calacatta marble shower tub. The renovation includes all-new electrical and plumbing systems, an efficient tankless hot water heater, a metal roof, impact-rated windows and opening protections, and stylish finishes throughout. Situated in the desirable X Flood Zone, the property offers an added layer of peace of mind with reduced flood risk concerns. Steeped in Key West history, this charming cottage was once home to a local cigar maker, offering a connection to the island's rich cultural heritage while embracing the pleasures of contemporary living.

1105 Olivia St, Key West
$2,800,000
2 Beds ⋅ 2 Baths ⋅ 620355 MLS
High Income-Producing Transient Licensed Gem in the Heart of Old Town Key West! Rare opportunity to own a highly sought-after transient licensed vacation rental in one of Key West's most desirable Old Town locations. This charming 2-bedroom, 2-bath home also features a versatile bonus room, offering additional space for guests, a home office, or a creative retreat. Thoughtfully updated from top to bottom, the property boasts a new roof, A/C system, appliances, water heater, furniture, decking, pool and much more--providing a truly turnkey investment. A proven performer, this popular vacation rental enjoys strong occupancy, excellent reviews, and consistent income potential. ''Potter's Cottage'' a true Key West conch house, showcases artistic character and unique touches of the former owner who was a well known Key West potter, creating an authentic Key West experience that guests love. Outside, enjoy a beautifully refreshed salt water pool area, a covered lanai, an outdoor shower, new Trex decking, and inviting outdoor living spaces designed for relaxation and entertaining. The quaint front porch offers the perfect spot to unwind and soak in the vibrant neighborhood atmosphere. Ideally situated in the heart of Old Town, you're just steps from Duval Street, world-class dining, shopping, galleries, entertainment, and historic attractions. Leave the car behind--everything Key West has to offer is within easy walking or biking distance. Whether you're seeking a profitable investment, a personal island getaway, or the best of both worlds, this exceptional property delivers. A buyer can step into existing bookings and reputation on day one, proven 5.0 rating, 100 plus reviews and strong repeat bookings. Schedule your private showing today and discover this outstanding Key West opportunity.

1009 Whitehead St, Key West
$3,800,000
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