Key West Real Estate Search

Newest Key West Homes and Condos for Sale

$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
$449,000
620856 MLS
Rare opportunity to acquire a transferable Key West transient license. This license to be transferred to another property located within a City of Key West-approved short-term rental zoning district. Seller has a written determination from the Key West Planning Department confirming that this transient license is eligible for transfer. Documentation is available upon request. Don't miss this opportunity to secure a transferable transient license in one of the most desirable vacation rental markets in the country.

1 Transient, Not Provided
$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
$1,599,000
620732 MLS
Owner Financing Available - Flexible Terms! Rare opportunity in Midtown Key West! This cleared and vacant 75x100 lot--a true rarity on the island--is ready for your dream home. This property comes with a ROGO Exempt / Right-to-Build letter, saving you time and expense in the building process. Permit in process. The generous lot size allows room for a spacious home, pool, and lush landscaping, surrounded by mature trees that offer shade and privacy. Located in highly desirable Midtown Key West, you're close to everything--beaches, shopping, dining, and downtown Duval Street--while still enjoying a quiet residential neighborhood vibe. Whether you're a builder, investor, or someone ready to create their ideal Key West retreat, this property offers endless potential. Don't miss this rare opportunity--build your Key West dream home today! Seller is licensed FL Real Estate Agent

1513 Seminary 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
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Key West Homes for Sale

The United States of America’s southernmost point is Key West, Florida. With a fabulous location only one hundred and six miles from Havana, Cuba, the city is steeped in Spanish history. To reach Key West, you’ll need to fly into Key West International airport; otherwise, it requires driving one hundred and twenty-six miles from the mainland and crossing over forty-two bridges. Though one of the state’s most relaxing and exciting places to live, the island is only one mile wide and four miles long. It is a popular option for newlyweds, vacationers, musicians, authors, roosters, and a handful of kitties.

Seemingly disconnected from the rest of the world, Key West has a carefree vibe and residents that tend toward dark suntans, hippy attitudes, and permanent smiles. There are just as many second-home owners as full-time residents in the community, which has a population of roughly twenty-five thousand people. During significant week-long events like Fantasy Fest, Key West Power Boat Races, Conch Republic Independence Celebration, and Hemingway Days, the population doubles. Moreover, according to Trip Advisor, the city is the nation’s number one wedding destination.

Specific points of interest in Key West include the two-hundred-acre Key West Golf Club, Key West Bight Marina, Key West City Marina, Naval Air Station Key West, and Mallory Square. Likewise, there are several fabulous neighborhoods in Key West, such as Sunset Key, The Meadows, Key West Historic District, and Old Town. Each of these communities offers a different flavor of Key West real estate. Real estate in Key West is extraordinarily diverse and includes lower-maintenance housing, houseboats, and older homes, as well as sprawling Key West luxury estates and everything in between. Please contact us today, and we will share details about the specific properties currently available in Key West, Florida, to assist you with your Key West home search.

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