Refine Search
Sort by
$999,000
3 Beds 2 Baths 620987 MLS
Charming Historic Old Town Key West Home, Ready for Its Next Chapter! Here's an opportunity for the buyer who sees possibility where others see a project. This 3-bedroom, 1.5-bath historic Key West home is tucked into the heart of Old Town, just minutes from the Historic Seaport, downtown, restaurants, shopping, and everything that makes island living so special. With classic Key West architecture, a welcoming front porch, hardwood floors, vintage windows, and plenty of original character, the home offers a wonderful starting point for a thoughtful renovation. The interior has been freshly painted, but this is a property that will require renovation and is best suited for a buyer ready to take on a true restoration project. Currently tenant occupied, the property also offers the advantage of existing rental income while a new owner makes plans, lines up contractors, or prepares for a future renovation or move-in. The existing floor plan includes generous living space, three bedrooms, a full bath downstairs, a half bath upstairs, and a private backyard with the potential to become a lush tropical retreat. For the right buyer, the appeal is undeniable: an authentic Old Town home, a highly desirable location, existing income, and the opportunity to restore, reimagine, and create something truly special. Bring your contractor, your creativity, and your vision. This one isn't pretending to be turnkey, but it just might be worth the work. *some photos digitally enhanced only to remove personal belongings

506 Grinnell St, 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

$1,695,000
2 Beds 2 Baths 620684 MLS
Fully furnished, 2b/2b designer-complete home 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, reconfigured 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 1b/1b 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. Meticulous detail throughout makes this A MUST SEE. Low fee insurance costs available upon request.

907 Frances St, 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

$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

$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

$1,250,000
2 Beds 2 Baths 620075 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

$1,150,000
2 Beds 2 Baths 620012 MLS
Tucked away on a quiet lane in Old Town Key West, this historic island home offers a rare combination of architectural character, elevated location, and walkable convenience. Positioned in the desirable X-flood zone near the highest natural elevation on the island, the property sits just steps from the energy of Duval Street while maintaining a peaceful residential feel. Originally constructed during the Henry Flagler railroad era, the home has been thoughtfully updated while preserving the warmth and authenticity that make Key West architecture so iconic. Inside, rich Dade County pine walls, hardwood flooring, and tall ceilings create an inviting atmosphere filled with natural texture and timeless charm. Impact windows and curated high-end finishes blend seamlessly with the home's historic roots. The kitchen was designed with both style and function in mind, featuring dade county pine countertops and a collection of premium appliances including a Sub-Zero refrigerator and Big Chill gas range. Flexible living areas allow the home to function as either a spacious two-bedroom retreat or a three-bedroom layout depending on your needs. Outdoor living is equally special. A lush backyard filled with mature tropical landscaping and fruit trees creates a private island setting that feels worlds away from the bustle of town, with space to potentially add a pool in the future. The welcoming front porch serves as a timeless gathering space, perfectly suited for morning coffee, evening cocktails, and enjoying the laid-back rhythm of Old Town living. Just a short stroll from Truman Waterfront Park, Fort Zachary Taylor Beach, galleries, restaurants, and marinas, this property captures the essence of classic Old Town living -- historic, relaxed, and unmistakably Key West.

709 Chapman 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

$2,550,000
3 Beds 4 Baths 619579 MLS
Step into a residence that has captured the national spotlight. Recently honored as a Wall Street Journal ''House of the Week,'' 1017 Angela Street is a 118-year-old Old Town cottage masterfully reimagined for the modern connoisseur. Tucked away on a tranquil lane, yet moments from the Historic Seaport and Duval Street, this three bedroom, three and a half bath home is the ultimate blend of calm island style and sophisticated Key West living. From the quintessential front porch to the vibrant, playful interiors, every inch of this home radiates personality. The heart of the residence features rare, historic Dade County Pine walls and floors bathed in natural light, creating a warm, textured backdrop for the home's contemporary finishes. The thoughtfully designed L-shaped layout effortlessly connects the chef's kitchen-complete with granite countertops and stainless appliances-to the bar and living areas. This social heart of the home seamlessly merges with an expansive dining area, where impact-rated French doors invite the island breeze, creating a natural environment for entertaining. The floor plan includes a coveted first-floor primary suite for ultimate convenience. The home's artistic soul is further defined by a series of custom murals by artist Haley Leeper, most notably the hand-painted staircase, which creates an artistic transition to the second floor. Upstairs features a second primary bedroom with a spa-inspired bath and an intimate reading nook and an additional guest suite. The backyard is a secluded oasis, boasting a heated pool and spa with an upgraded system, outdoor shower, and Trex decking. Framed by lush tropical foliage and a magnificent, mature mango tree, this space offers a level of privacy and shade. Complete with off-street parking and a distinguished track record as a top-performing monthly rental, 1017 Angela Street is a ''turnkey'' treasure that perfectly balances historic architectural significance with lucrative investment potenti

1017 Angela St, Key West

$1,249,000
3 Beds 3 Baths 619554 MLS
Historic Old Town Key West home offering character, a prime location, and strong potential for a buyer looking to add value. Originally built in 1908 and positioned on a desirable corner lot, this 3-bedroom, 3-bath property is just moments from galleries, dining, the waterfront, and Key West's well-known sunsets. The interior features high ceilings, Dade County pine floors, and an open living and dining layout with good natural light. The kitchen includes gas cooking, ample storage, and a functional footprint that can be updated or reconfigured to fit your needs. Upstairs, the primary suite offers vaulted ceilings with exposed beams and an en-suite bath with mosaic tilework. Additional bedrooms provide flexibility for guests, roommates, or rental use. Exterior features include multiple porch areas, mature tropical landscaping, and a private yard. Off-street parking, a spacious pantry, and distinctive details such as a hand-carved Brazilian mahogany front door contribute to the home's overall value. Located in the heart of Old Town, this property presents an opportunity for a full-time residence, second home, or investment in one of Key West's most desirable neighborhoods.

846 Olivia St, Key West

$2,200,000
5 Beds 4 Baths 619406 MLS
Two Parcels Included!!! Welcome to 1320 6th Street, a fantastic investment opportunity in a prime midtown Key West location. This property features three private units, each offering great rental income potential. Your chance to make money and have a home in paradise. Newly remodeled kitchen in the rental home. Enjoy the large inviting pool and well-maintained grounds, all just minutes from downtown Key West. Whether you're looking for a lucrative rental property or a versatile family compound, this unique property is a perfect choice. Don't miss your chance to own this gem in the heart of Key West! Prime Corner Lot enjoy the benefits of a corner lot with enhanced privacy and curb appeal. The property has ample parking and features a three-vehicle covered carport, along with additional off-street parking that can accommodate your boat or RV. The layout and landscaping provide a sense of seclusion, ensuring a comfortable living experience for tenants. This multi-family property is a rare find, combining practicality, privacy, and profitability. Don't miss out on this outstanding investment opportunity!

1320 6th St, Key West

$899,000
3 Beds 2 Baths 619102 MLS
Welcome to 3011 Riviera Drive, nestled in the sought-after Riviera Shores neighborhood of Key West! This delightful 3-bedroom, 2-bathroom home boasts versatility and space, featuring a spacious bonus room--ideal for guests or an in-law suite. The property sits on a generous 6,000 sq ft lot with a large fenced backyard, perfect for adding a pool. Relish in the tranquility of mature banana and mango trees, complemented by tall Christmas palms enhancing the front yard's allure. Enjoy off-street parking, a concrete driveway, and the nearby public boat ramp for aquatic adventures. The home includes nice comforts such as a durable metal roof, sound proof windows and doors, storm shutters, and a privacy fence. Relax on the covered back patio, and appreciate the proximity to Key West's Old Town, beaches, schools, shopping, and businesses--truly an inviting retreat!

3011 Riviera Dr, Key West

$2,549,000
3 Beds 4 Baths 618952 MLS
**Seller Financing Considered** 2924 Riviera Dr is a Must See! Meticulously renovated house on the Riviera Canal. Features 3 bedrooms, 2 full baths & 2 half baths, plus separate pool / canal side cottage. Open & airy living room & kitchen gives you spectacular views of backyard, pool and canal. You can even see the pool and canal from the front door. Owner / Seller is a carpenter. House was stripped to the concrete block walls and rebuilt (with permits) with all new materials. New impact windows & doors, roof (with straps), ductless AC ( 2 compressors, 6 heads), electrical - 200 Amp service, water supply lines, manifold style on demand water heater, Turkish Marble floors throughout (no ceramic tile), drywall on walls & ceiling, kitchen cabinets & counter tops, appliances, bathroom fixtures, and much, much more. Even has interior laundry & utility room. Expansive primary bedroom with walk thru closet and spacious ensuite bath, plus pool & canal views. Enjoy the convenience of living in Key West and having your boat in your back yard. Concrete seawall (59Ft) with newer 12,000 Ibs boat lift and inground pool (with newer pump / filter) compliment the canal-front back yard. Lot is 7,670 sq ft. Located close to schools, professional offices, shopping, airport & beaches. Just a short ride to Duval St and the all the Old Town KW attractions. House is turn-key. Simply unpack your swimsuit and start enjoying the Keys lifestyle. **Seller is open to financing the Buyer**

2924 Riviera Dr, Key West

$1,079,000
4 Beds 2 Baths 616878 MLS
Welcome to 2926 Flagler Avenue! This single-family home has four bedrooms and two baths, a swimming pool and is nestled on a 6,360 square foot lot located in a wonderful New Town central location. The spacious interior affords you the opportunity to entertain family, friends, and truly relax in comfort. Having been well maintained throughout the years, this CBS home has a v-crimp metal roof, impact rated windows and doors throughout plus accordion shutters providing an additional layer of peace of mind protection. The open layout features a flexible living atmosphere that leads to the possibility of one bedroom being a lockout with its own exterior entrance or an ideal multigenerational living arrangement. The low maintenance backyard is perfect for entertaining, and the swimming pool is sure to bring joy to those who yearn for living the Key West lifestyle. A fully fenced yard offers privacy and security. Located within minutes of shopping, the beaches, and many wonderful dining venues that Key West has to offer. This property is the one that checks off many of the boxes and is competitively price to sell. Please call me today to view your future home!

2926 Flagler Ave, Key West

$940,000
2 Beds 2 Baths 617688 MLS
Spectacular sunrise ocean views from this beautifully renovated Key West By The Sea condo on Smathers Beach. This 2-bedroom, 1.5-bath residence feels like new construction, featuring a fully remodeled kitchen with new appliances, updated bathrooms, new flooring throughout, dimmable lighting, new fans, and more. The Mitsubishi mini-split AC and heating system, upgraded electrical panel, water heater, and hurricane-impact soundproof doors and windows are all in pristine condition. Enjoy unobstructed views from the balcony overlooking Smathers Beach and the Atlantic Ocean, with paddleboard, kayak, sailboat, parasail, chair, and umbrella rentals just steps away. Key West By The Sea is a gated community offering two swimming pools, two tennis courts, a clubhouse, four laundry rooms, a car-wash station, bike racks, a pet-walking path, and lush fruit trees. This pet-friendly community includes building insurance, cable TV, Wi-Fi, and building/grounds maintenance in the condo fee.

2601 S Roosevelt Blvd Unit 406A, Key West

$615,000
1 Beds 1 Baths 618286 MLS
Wake up to breathtaking direct ocean views from this second-floor, 1-bedroom, 1-bath residence located in the desirable 'A' building at Key West by the Sea. This bright and airy condo designed to capture natural light and showcase the stunning beach and ocean scenery. The unit was upgraded through the 2018 Airport Noise Improvement Project and includes hurricane-impact, sound-insulated windows and doors, providing exceptional tranquility throughout the home. Energy-efficient ductless mini-split A/C systems in both the living area and bedroom offer customized comfort year-round. Situated directly across the street from iconic Smathers Beach, this location is ideal for beach lovers and outdoor enthusiasts alike. Enjoy swimming, sunbathing, and watersports, or take advantage of the wide, paved beachfront promenadeâ€'perfect for biking, jogging, skating, or leisurely sunset strolls. The gated Key West by the Sea community offers resort-style amenities including two swimming pools, two tennis courts, a clubhouse, four conveniently located laundry rooms, bike racks, a car-wash station, and a pet walking area. The community is pet-friendly and well maintained, with condo fees covering building insurance, cable TV, security, pest control, and full grounds and building maintenance. After the first year of ownership, the unit may be rented with a minimum two-month term, adding flexibility and investment potential. Whether you're searching for a serene island retreat, a full-time residence, or a smart coastal investment, this oceanview condo delivers the best of Key West livingâ€'location, views, and lifestyleâ€'all in one exceptional package.

2601 S Roosevelt Blvd Unit 204A, Key West

$4,300,000
4 Beds 6 Baths 617513 MLS
**31 photos have been virtually staged and enhanced to assist buyers in visualizing design and decor options for this home.** Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996 and set at 13' elevation on Solares Hill, the residence pays homage to the architectural romance of Old Town's most celebrated homes.. broad verandas, intricate trim work, and Brazilian Cherry hardwood floors that recall a bygone era of island craftsmanship. Inside, the home unfolds in layers of refinement. Sunlit rooms connect gracefully to the outdoors through French doors and deep porches. The main house's split-level design elevates the primary suite with its own private staircase, while two additional bedrooms ascend another, creating a sense of calm seclusion. A separate pool suite, complete with private entrance, extends the home's versatility. The kitchen is anchored by a suite of premier appliances.. including a new SubZero refrigerator and a refurbished Viking gas range, and framed by custom cabinetry and built-ins. Recent upgrades such as the 2025 metal roof, updated HVAC systems, and a 24 kW Generac whole-house generator reflect meticulous stewardship. Outside, the grounds rise to the level of a private resort. Tropical gardens wind around stone pathways, illuminated at night by soft landscape lighting. A heated saltwater lagoon-style pool, resurfaced in 2025, curves around natural rock formations, a spa, and three cascading waterfalls. Every vista offers a moment of stillness.. from the shaded verandas to the courtyard designed for open-air dining. A one-car air-conditioned garage, currently serving as an art studio, and a two-car driveway complete the thoughtful layout. Just blocks from Duval Street and the Key West Historic Seaport, Casa Sapodilla is both connected and deeply private.. a luxury retreat rooted in island elegance.. Inquire within for details on the low insurance costs available for this home

600 Elizabeth St, Key West

$2,033,000
2 Beds 1 Baths 618183 MLS
Rare opportunity on desirable Aronovitz Lane in the heart of Key West! This unique offering includes two properties being sold together, creating exceptional flexibility for investors, builders, or lifestyle buyers. The package includes a vacant lot with the ability to rebuild its original two-unit footprint, a true rarity in Key West, presenting an exceptional chance to develop new construction in a prime setting. Paired with this is an existing 2-bedroom, 1-bath home, ideal for island living, income production, or incorporation into a larger architectural vision. Whether you're a builder seeking scarce development rights, an investor looking to maximize returns, or a buyer with a long-term Key West strategy, this is a once-in-a-market opportunity with limitless potential. Quietly tucked away yet steps from Key West's most celebrated dining, galleries, and waterfront experiences. This is Old Town Key West at its absolute best.

1 & 2 Aronovitz Ln, Key West