Key West Real Estate Search

Newest Key West Homes and Condos for Sale

$1,678,000
4 Beds ⋅ 4 Baths ⋅ 619991 MLS
Welcome to 2519 Staples Avenue, a fully reimagined residence in the heart of Midtown Key West, set on a rare 10,000 sq ft corner lot along one of the area's most bicyclable and desirable streets in Midtown. Recently completed renovations offer the opportunity to be the first to live in this thoughtfully rethought home, where modern upgrades meet relaxed island living. Spanning approximately 2,100 sq ft, the property features 4 bedrooms and 3.5 bathrooms, with a layout designed for both comfort and functionality. The primary suite serves as a private retreat, complete with direct access to the backyard, a spacious walk-in closet, and a beautifully appointed ensuite bathroom. Outdoor living is where this home truly stands out. A newly installed pool with elegant deck jets creates a serene, resort-style setting, fully enclosed for privacy. The new addition of a bright and airy pool room offers a seamless indoor-outdoor flow- perfect for entertaining or unwinding. There is a separate sitting and dining area for eating and lounging el fresco. Beautiful mature fruit trees provide shade and produce fruit annually. Additional upgrades include all impact windows and doors, providing peace of mind and energy efficiency throughout. New sewer and plumbing pipes to the road. New electrical and a new water heater. There is plenty of parking for a boat, a truck, a golf cart and a car. Properties offering this combination of lot size, location, and new construction-level renovations are exceptionally rare in Key West. Whether you're seeking a full-time residence, a family home, or a vacation retreat, this property delivers. House is being offered fully furnished minus personal items, art, and rugs. A true standout opportunity in Midtown--don't miss it.

2519 Staples Ave, Key West
$2,500,000
8 Beds ⋅ 4 Baths ⋅ 619978 MLS
Discover an exceptional investment opportunity in the heart of the Florida Keys! Situated on a spacious lot just 3 minutes from the beach and world-famous Duval Street, this unique multi-unit property offers versatility, comfort, and island-style living at its finest. The main residence features 5 bedrooms and 3 bathrooms across 2,432 total s/f, designed for both relaxation and entertaining. Enjoy a private pool with pool heater, along with the convenience of two elevated A/C units, both less than 4 years old. The second unit offers 3 bedrooms and 1 bathroom with 1,504 total s/f of living space, plus a 2-car garage and its own elevated A/C unit, also less than 4 years old. Built for peace of mind and modern living, the property includes a durable metal roof, impact windows throughout, camera security system, preparation for an electric vehicle charger, and separate electric and water meters for each unit. Whether you're seeking a primary residence, vacation retreat, or income-producing property, this rare Florida Keys gem combines location, flexibility, and outstanding features in one incredible package.

1409 Whalton St, Key West
$1,170,000
3 Beds ⋅ 3 Baths ⋅ 619952 MLS
Hidden away on one of Old Town's most storied streets, 1016 Varela St. Rear is the kind of Key West address that feels like a private discovery. Originally constructed in the 1920s, this piece of living Key West history has been thoughtfully renovated while honoring the character that only a century of island life can impart. Tucked discreetly behind the street, the fully restored 3-bedroom, 3-bathroom residence offers a rare sense of seclusion in the heart of historic Old Town -- without sacrificing a single step of the legendary walkability that defines this neighborhood. Duval Street, world-class dining, the harbor, and the full tapestry of Key West life are all moments away on foot. Arrive home to a covered front porch -- the quintessential Key West perch for morning coffee or evening cocktails. Inside, soaring cathedral ceilings flood the living spaces with light and volume, while refinished hardwood floors, an updated kitchen, and impact windows throughout speak to a renovation done with care and intention. The private rear yard offers room for a pool, a rare opportunity to create your own tropical retreat in the heart of Old Town. A separate upstairs apartment with its own private entrance offers exceptional flexibility: a sanctuary for a young adult, an elegant in-law suite, or an income-producing rental that helps carry the property. For the discerning buyer, two details stand above the rest: 1016 Varela Rear sits in an X flood zone -- the premier flood designation in the Keys, carrying no flood insurance requirement -- and the property carries an assumable VA loan, a remarkable financial advantage for qualified buyers in today's market. In Old Town Key West, a century-old home with this much flexibility and this little compromise is extraordinarily rare. Welcome to your hidden corner of paradise.

1016 Varela St Unit Rear, Key West
$1,675,000
5 Beds ⋅ 3 Baths ⋅ 619947 MLS
Welcome to 606 Grinnell Street located in the heart of Old Town Key West, this charming duplex offers the perfect blend of classic Key West character and flexible living opportunities. The first-floor unit features 2 nice sized bedrooms and 1.5 baths, while the spacious second-floor unit offers 3 bedrooms and 1 bath, complete with a private rear balcony overlooking the backyard oasis. Both units feature full sized kitchens with great dining spaces, as well as living rooms too. A welcoming front porch adds to the home's island charm, creating the perfect spot to relax and enjoy the neighborhood atmosphere. Step outside to your private backyard retreat featuring a sparkling pool for your relaxation, ideal for entertaining, time off, or enjoying the Key West lifestyle year-round. Whether you're looking for an investment property, multi-generational living, or the option to live in one unit while renting the other, this versatile Old Town property offers endless potential. There's a convenient side door entrance for the 2nd unit upstairs, while having a lockout door in the first unit if you wanted access to upstairs. Nice thought for Indoor or Outdoor Access to upstairs. Just moments from world-famous Duval Street with lots of dining options, historical seaport, shopping, and nightlife experiences.

606 Grinnell St, Key West
$2,345,000
5 Beds ⋅ 4 Baths ⋅ 619927 MLS
FOUR UNIT Property in a Prime Old Town Key West Location with LOTS of OPTIONS! 1104 Truman Avenue is a legal four-unit property with multiple use possibilities. Generous off-street parking; a rare and valuable feature in Old Town, enhances desirability for business and/or residential occupants. Classic Conch-style construction with covered porches adds to the property's island appeal and long-term value. The property currently consists of one 2BR/1BA unit and three 1BR/1BA units, all licensed rentals.. Flexible layout supports a variety of uses including long-term rentals, monthly vacation rentals, employee housing, or mixed-use potential with possible commercial use on the ground level and residential above. The property also offers the potential to be reimagined as a spacious single-family residence. (Buyer to verify) This is an extremely well-located property with multiple use possibilities in a high-demand rental market.

1104 Truman Ave, Key West
$1,799,999
7 Beds ⋅ 5 Baths ⋅ 619911 MLS
Endless possiblities! Three units to rent for the investor or live in one and produce income from the other units. Downstairs you have a 3/1.5 with an open floor plan and covered porch with a patio. Upstairs you have two units with a 2/1 floor plan and a fire wall between units. All units have W/D hook ups and central air. Both units upstairs have balconies and seperate staircases for entry. Low maintence yardcare. Covered and dedicated parking with street parking as well. Great location close to downtown and the beaches. Owner is a general contractor and has lived in the home since 1972 and added the second story in 1994.

1504 Flagler Ave, Key West
$1,799,000
7 Beds ⋅ 5 Baths ⋅ 619904 MLS
Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind down in the evenings on the upstairs balcony overlooking the quiet, tree lined street. Just steps away, 624 Petronia Street offers a well designed duplex with two separate 1-bedroom, 1-bath units: each complete with a full kitchen and private washer and dryer, making them ideal for guests, tenants, or extended family. Between the two homes, a welcoming shared patio creates the perfect setting for outdoor dining, grilling, and relaxed island living under the palms. Situated in a desirable X flood zone (one of the highest elevations in Key West) this property combines peace of mind with an unbeatable Old Town location close to everything, yet tucked away from the hustle. Whether you're seeking an income producing investment, a family compound, or a private island retreat with room for everyone, this rare offering captures the true spirit of Key West living.

800 Elizabeth St, Key West
$7,500,000
5 Beds ⋅ 5 Baths ⋅ 619886 MLS
At the end of prestigious Sunrise Lane, where land meets open water on 3 sides, 3750 Sunrise Lane stands as one of the most extraordinary waterfront offerings in Key West. Properties of this scale and setting rarely exist, and almost never come to market. Originally built in the 1950s and extensively rebuilt in 1999, this legacy estate sits on a 28,500sf peninsula, offering a rare scale, privacy, and waterfront presence that is nearly impossible to replicate. The 5,378sf residence blends timeless architecture with expansive indoor and outdoor living. The main level features gracious living spaces with heart pine floors, French doors, and light-filled rooms opening to wide terraces and tranquil water views. The home offers 5 bedrooms and 4.5 baths, including 3 first-floor bedrooms and a spacious primary suite designed for comfort and privacy. Upstairs, 2 guest bedrooms open to a covered balcony and rare widow's walk with panoramic views of the Atlantic, Gulf, and surrounding protected lands. At the heart of the home is an expansive family-style kitchen with a large breakfast room, bar seating, desk area, and rich wood cabinetry. A handsome den with a built-in wet bar creates a warm gathering space, while a studio/flex room offers versatility as an office, art studio, fitness room, or guest overflow. The grounds are equally remarkable, featuring mature tropical landscaping, a large swimming pool, and over 3,200sf of brick patios. Nearly 500 linear feet of seawall provide exceptional dockage with a concrete dock and 2 boat lifts offering immediate deep-water access to both the Atlantic and Gulf. An oversized finished 828sf garage with 4 garage doors adds rare flexibility and functionality. This legacy estate awaits restoration and the vision of its next owner. Its setting, structure, and scale create a once-in-a-generation opportunity to reimagine one of Key West's most significant waterfront properties.

3750 Sunrise Ln, Key West
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619758 MLS
With only two owners in its history, this well-maintained two-story property presents a rare investment opportunity in Key West. Configured as a legal duplex with two separately metered 1-bedroom, 1-bath units, it offers exceptional flexibility--ideal for investors seeking strong rental potential, business owners looking for employee housing, or owner-occupants wanting to offset costs by renting one unit while living in the other. Set on a 5,000 sq ft lot, the property is surrounded by lush, mature tropical landscaping with a wide variety of plants and palms, creating a private, shaded, treehouse-like setting filled with natural light. Two large screened porches and additional open-air spaces provide ideal indoor-outdoor living, while an outdoor shower enhances the island lifestyle. The home has been thoughtfully updated and well cared for, featuring Mitsubishi mini-split A/C systems in both units, a new hot water heater, new ceiling fans, impact windows upstairs, new gutters, updated appliances, and soft-close cabinetry. Interior finishes include a mix of pine, vinyl, and concrete flooring, along with stainless, Formica, and butcher block countertops. Both units offer full bathrooms with tubs. Additional highlights include two off-street parking spaces, low-maintenance grounds, and multiple windows throughout for abundant natural light and airflow. Located in desirable Midtown East, just minutes from everything Key West has to offer, this is a versatile, income-producing property with strong upside potential.

1911 Seidenberg Ave, Key West
$1,299,000
4 Beds ⋅ 2 Baths ⋅ 619738 MLS
FLIP FLOPS INLCUDED! Some homes are just addresses. This one is a lifestyle. Tucked into the heart of Old Town Key West, this beautiful historic Conch home is wrapped in the warmth of original Dade County pine and rich hardwood floors -- the kind of craftsmanship that simply isn't built anymore. The main house offers three bedrooms and a fully renovated bath, anchored by a large kitchen with generous cabinet space.. A fully enclosed porch is your place for morning coffee, chatting around the table or dining while overlooking the pool. Central air conditioning keeps things cool. Every window and door has been upgraded to impact, giving you peace of mind alongside the charm. Step outside and the magic continues. A sparkling pool with a waterfall feature and Trex decking invites you to linger. An outdoor shower makes coming in from the water effortless. The fully fenced front and back yards create a private tropical sanctuary, and off-street parking -- a true luxury in Old Town -- takes the stress out of coming home. The guest cottage is its own retreat, offering one bedroom, one bath, and a Murphy bed that makes the space as flexible as your plans. Whether it becomes a private getaway for family and friends, a creative studio or a detached office, it gives this property a versatility that is genuinely rare. The location is the final piece that makes everything click. A ten-minute walk from Duval Street -live music, art galleries, open-air restaurants, theaters and the electric pulse that makes Key West unlike anywhere else on earth. 7 minutes the other way brings you to the White Street District know for Fausto's Food Palace, where locals have shopped for generations, and the legendary Sandy's Café. This property comes fully turn-key, bedding, housewares, pool toys, bicycles, and yes, flip flops are included. Whether you wanting a second home, a monthly vacation rental or simply ready to walk through the door and start living living in paradise.

928 United St, Key West
$9,888,000
3 Beds ⋅ 2 Baths ⋅ 619724 MLS
Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai--it's an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Motels, transient lodging, and more. This two-story home comes equipped with two separate electric meters. This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now-- an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown. Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial venture boutique hotel, or restaurant, -- this and more are supported by HCT zoning. This property is all about the excitement of shaping a new vision for a future in paradise. Let your imagination run wild and transform this blank canvas into something extraordinary. Don't miss out on this once-in-lifetime opportunity--call today for your private tour and start envisioning your future in Key West!

1430 Vernon Ave, Key West
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 619723 MLS
DUPLEX! Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath. There is also a laundry room with additional storage space. The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.

1516 17th Ter, Key West
$2,900,000
2 Beds ⋅ 2 Baths ⋅ 619715 MLS
Seclusion meets striking contemporary design in this elevated sanctuary, positioned just moments from Higgs Beach and White Street Pier. Behind a signature pivoting red gate and architectural peekaboo wall, the residence unfolds as a curated experience of light and geometry. The entry foyer--anchored by a sun-drenched desk nook and an open-tread staircase--leads to a living space defined by floor-to-ceiling glass and transom detailing that frames the outdoor oasis like a living gallery. The culinary space is anchored by a sleek, minimalist aesthetic, featuring custom cabinetry, crisp white surfaces, and Bosch appliances. A glass-door pantry provides a sophisticated home for provisions, blending functional utility with the kitchen's clean geometry For guests, a private main-level suite is tucked away behind a discreet pocket door, offering an ensuite bathroom and ample closet space for a completely independent wing. The second floor is dedicated entirely to the primary retreat. This suite features a large walk-in closet and a refined ensuite bathroom. Just beyond the sleeping quarters is a private balcony where an open-air soaking tub offers a quiet moment of luxury under the stars. The exterior of the home is a masterwork of tropical landscaping, where beautifully mature and lush greenery wraps the property in total privacy. At the heart of the grounds is an expansive heated pool bordered by a large deck, perfect for sun-drenched afternoons. For the host, the covered outdoor dining pavilion is fully equipped with an integrated grill and ample countertop space for seamless entertaining. Nearby, a serene Zen garden with a tranquil fountain feature provides a quiet corner for meditation and reflection. This is more than a home; it is a sophisticated, high-design haven just steps from the ocean.

1701 Laird St, Key West
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 619703 MLS
Strong value-add multifamily fourplex investment opportunity with major capital improvements already completed. The property offers four two-bedroom residences totaling approximately 3,000 square feet, with each unit comprising approximately 750 square feet. The lower level includes two residences, while the upper level features two additional residences with approximately 960 square feet of combined balcony space. Major improvements include a new standing-seam metal roof, new impact-resistant windows and doors throughout, and completed concrete, stucco, and exterior work. The property is ready for the next owner to complete the remaining work and execute their preferred investment strategy. Once completed and delivered furnished, the property is projected to have the potential to generate more than $200,000 in annual gross rental income across all four units. Additional potential may include condominium conversion, subject to all applicable approvals and requirements. A compelling opportunity to complete, stabilize, and maximize a well-positioned Key West income-producing asset.

1224 2nd St, Key West
$1,799,000
7 Beds ⋅ 5 Baths ⋅ 619700 MLS
Tucked into one of Old Town's most peaceful and charming pockets, this unique multi-unit property offers the perfect blend of classic Key West character and flexible living. At 800 Elizabeth Street, you'll find a quintessential two-story Conch home featuring 5 bedrooms and 3 bathrooms, soaring ceilings, and timeless architectural details. Start your mornings on the inviting front porch and wind down in the evenings on the upstairs balcony overlooking the quiet, tree lined street. Just steps away, 624 Petronia Street offers a well designed duplex with two separate 1-bedroom, 1-bath units: each complete with a full kitchen and private washer and dryer, making them ideal for guests, tenants, or extended family. Between the two homes, a welcoming shared patio creates the perfect setting for outdoor dining, grilling, and relaxed island living under the palms. Situated in a desirable X flood zone (one of the highest elevations in Key West) this property combines peace of mind with an unbeatable Old Town location close to everything, yet tucked away from the hustle. Whether you're seeking an income producing investment, a family compound, or a private island retreat with room for everyone, this rare offering captures the true spirit of Key West living.

800 Elizabeth St, 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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