166 houses for sale in Key West city

Heart of Old Town Key West. Very rare FULLY RENTED income producing mixed-use property. 2u002F2 residential, office plus a detached restaurant. Seller financing is available to immediately start your investment opportunity! Call now for your private showing

Charming remodeled 1929 Old Town Key West home on iconic Margaret Street, offering privacy, new impact windows & doors, flooring and timeless island feel. Set back from the street, this three-bedroom, two bath residence feels like a peaceful retreat while remaining close to Duval Street and the historic seaport. The outdoor living space features a beautiful pool and spa area surrounded by a spacious deck, perfect for relaxing and entertaining. A small separate pool house with a half bath adds convenience and flexibility (not included in square footage). A rare opportunity to enjoy classic Key West charm with exceptional outdoor living in a prime location

Experience effortless island living in this stunning, recently renovated estate, situated on a rare double lot in the high-and-dry X flood zone. Framed by lush tropical landscaping, the home welcomes you with a classic wrap-around porch-a quintessential setting for morning coffee or golden-hour cocktails. This sophisticated residence comprises four bedrooms and three bathrooms across a main house and a detached guest cottage, offering a seamless blend of historic island charm and high-end contemporary refinement. The main home boasts soaring ceilings and sun-drenched volumes that flow seamlessly toward the outdoors. A chef's dream, the kitchen is a masterclass in design, featuring custom cabinetry, a striking quartz waterfall island, and a suite of stainless steel Thermador appliances-including an oversized professional 6-door, French-door refrigerator. The entire second floor is a dedicated primary retreat designed for ultimate sanctuary. This sprawling level features a private balcon

Some homes are built; others are authored. This is one of the latter-an architectural landmark shaped by David Wolkowsky, whose vision helped define Key West itself, with architecture by award-winning architect Rob Delaune that thoughtfully carries that legacy forward. This three-bedroom, three-and-a-half-bath estate, built in 1999 and comprehensively updated from the ground up, has been meticulously restored to museum-level standards with all-new systems, impact-rated windows and doors, and 10-foot doors and sliders throughout. The dramatic main living space is defined by soaring 22-foot ceilings, refinished custom teak columns and doors, expansive walls of glass, and a striking floor-to-ceiling built-in bookcase spanning the full height and length of the living room wall, complete with a concealed automatic disappearing television, while a thoughtfully designed chef's kitchen anchors the home with both beauty and functionality for everyday living and entertaining. Set on a rare, full

Charming Old Town Retreat in X Flood Zone! Step into island living with this beautifully renovated 1-bedroom, 1.5-bath home, plus sleeping loft and cabana, in the heart of Old Town Key West. Thoughtfully updated with quartz countertops, custom wood cabinetry, and top-of-the-line stainless steel appliances, this home seamlessly blends modern comfort with historic charm. A cozy sleeping loft offers extra space for guests or lounging, while a separate structure on the property can serve as a studio, guest room, or private cabana. Nestled on a generously sized lot in the desirable X flood zone, this home also conveys with a 1u002F10 interest in a private parking lot behind the residence-a rare Key West perk! Don't miss your chance to own a versatile and stylish island escape in one of Key West's most sought-after neighborhoods

Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment. This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. Ft. of living space on an 8,227 sq. Ft.oversized lot, providing rare space and privacy in one of the island's most desirable neighborhoods. Enter through the white picket fence and tropical courtyard to your grand Key West estate, where every detail has been thoughtfully designed. The first floor is set for entertaining, featuring a spacious living area and a chef's kitchen with stone countertops, an oversized island, custom cabinetry, and premium Sub-Zero, Viking, and Wolf appliances. A generous walk-in pantry adds extra storage convenience. The primary suite, also on the ground level, overlooks the pool and boasts a spa-inspired bath with dual showers, a freestanding soaking tub (with air bubble massage) and a large wa

Experience the epitome of luxury in this exquisite 3BDu002F3BA residence nestled on a quiet Lane in the heart of Old Town Key West, just a stone's throw from the world famous Southernmost Point and 1 block from the iconic Duval Street. Indulge in the unparalleled convenience of having Key West's renowned restaurants, museums, and art galleries at your doorstep, with the beach a leisurely bike ride away. Step into the modern charm of this meticulously maintained home, which was thoughtfully constructed in 2002. Enjoy the convenience of an open floor plan that seamlessly combines the living, dining, and kitchen areas. Revel in the sleek and stylish stainless steel appliances, complemented by the elegance of granite countertops and custom cabinetry. High vaulted ceilings create an inviting sense of space, while a harmonious blend of tile and wood floors adds a touch of sophistication. Into the backyard oasis, where a delightful heated and chilled pool awaits, ensconced in the lush embrace

Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic

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 o

Prime Multi Unit property in Old Town. Six legal apartments with 6 off street parking spaces is rarely available. There is a total of 10 bedrooms and 6 baths, divided into Three 1bdu002F1ba units, Two 2 bdu002F1ba units and one 3bdu002F1ba unit. Two story CBS & Frame building has total of 3,876 sf. Building sits on good size 3,598 sf. Lot that runs from Pohalski St. To Havana Lane giving each tenant easy access to their apartment and off street parking spot. Each apartment has it's own separate Electric and Water meter. Lot sits in a BFE flood zone, former X flood zone, and is high and dry. Gross rents total $14,500 per month with limited expenses. Property has been in the family for generations and ready to pass on to a new owner. Perfect for a long term investor, 1031 Exchange Replacement Property or Employee Housing!

Situated in the prestigious heart of Old Town, 906 Southard Street is an impeccably restored Historic Key West eyebrow house filled with timeless architectural character. This Home has off street parking, pool and all that Key West Charm you are looking for. A large ipe wood front porch adorned with classic gingerbread trim and iconic gas lanterns welcomes you to the refined residence. This home offers three (3) spacious bedrooms, each with its own private ensuite bathroom, ensuring comfort and privacy for residents and guests alike. The gourmet kitchen is a chef's masterpiece, featuring Carrera marble countertops, cherrywood cabinets, a gas Viking Professional range, two Liebherr refrigerators, and a dedicated ice maker and wine fridge. Adjacent, the skylight-lit dining area provides an inviting, sophisticated setting perfect for both intimate dinners and entertaining. Designed for indoor-outdoor living, the property features an outdoor dining area, with an ipe wood covered porch, a h

Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! That's less than $272K per unit! Renovations in progress. Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors. Ask your tax expert. Prime location, just 1u002F2 block from cemetery and 1u002F2 block off Truman Ave. Currently configured as 6 units (but City recognizes 7). Presently being used as: one 2-bedroom unit, three 1-bedroom units and 2 studio units. All with separate exterior entrances. Convenient location is close to many Old Town hot spots including world famous Duval St. Perfect for employee housing or income producing multi-unit property. Advanced notice required before showings and don't expect to see all six of the units at once. Please do NOT disturb tenants. This is a duplicate entry

An architecturally stunning renovation & upgrade of this classic Old Town Key West property is sure to meet all your needs. A welcoming front porch awaits as you depart from your rare 2 off-street parking spaces in Old Town, or alternatively, you may choose to arrive by bicycle & take advantage of the separate entrance with dedicated bike storage. A complete irrigation system with landscape lighting transforms the outside into a tropical paradise. One of the most productive mango trees in Key West produces many tasty mangoes each season. Enter the privately fenced & gated yard & take a dip in the heated pool. You can unwind in the backyard after a quick outdoor shower, enjoying the lighted grilling station & multiple spots to relax or dine under the stars. Beyond the impact glass folding doors is a spacious kitchen with an indoor dining area. All cabinets throughout the kitchen & the rest of the home are Hanson and Bringle cabinets. If you enjoy working in the kitchen, there is an indu

Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, and exceptional investment potential in a prime Old Town location. Located in an X flood zone, this property offers added peace of mind and potential savings on insurance-an increasingly valuable feature in today's market. This unique property is configured as two separate units, featuring a main two-story residence and a detached guest quarters, with a combined total of 2,573 square feet of living space. The detached unit is separately licensed and equipped with its own electric and water meters, providing true independence and strong income-producing potential. The main home offers a spacious and functional layout designed for island living. The first floor includes multiple living areas, with a generous living room, separate dining space, family room, and a well-appointed kitchen that opens to outdoor patio and deck areas-perfect for entertaining. Upstairs, you'll find three bedrooms, including a

Tucked into the heart of Old Town, this beautifully restored residence pairs Key West's historic character with thoughtful modern updates-all just one block off Duval Street and three blocks from the iconic Southernmost Point. Taken down to the studs and fully renovated in 2018, the three-bedroom, two-bath home delivers high-end finishes throughout, plus the rare bonuses of a private gated courtyard and off-street parking. The layout is built for easy island living, blurring the line between indoors and out. Refined touches run throughout: impact-rated doors and windows, rich oak floors, custom tilework, and original Dade County Pine that's been carefully preserved. At the center of it all, the kitchen is made for entertaining, with stainless appliances, brushed marble counters, and eye-catching copper and bronze fixtures. The generously sized primary suite is a true retreat-vaulted cypress ceilings, a spa-inspired en suite, a showpiece copper soaking tub, and custom closets with room

X Flood Zone 13ft above sea-level! Gorgeous CONCH home in the ultimate Old Town location. Only one block from Duval, in a neighborhood lined with historic homes! Live in the heart of Old Town where charming architecture, iconic streetscapes, and Key West's finest restaurants and shops are right outside your door. This beautifully restored 1889 Conch home has been completely renovated in 2022 to the studs, blending historic character with sophisticated modern upgrades. Currently configured as a single family home, open-concept living area, 10 ft ceilings and restored Dade County Pine throughout. The great room flows into the chef's kitchen featuring high-end Cafe appliances, gas range, and custom cast-in-place concrete countertops. A bespoke bar framed with antique doors creates the perfect spot to prepare a cocktail before stepping onto your private porch. Two inviting first-floor guest rooms share a luxurious bath with a deep 17' soaking tub. The custom staircase leads to a serene pri

Discover a seamless blend of historic character and modern refinement at 1209 Packer Street, a distinctive Old Town residence that quietly impresses from the moment you step inside. Drawing inspiration from the rich architectural tapestry of Key West, this home thoughtfully weaves together Old Key West charm, Cuban mosaic tile accents, and contemporary finishes to create an atmosphere that feels both timeless and current. LOCATED IN XBehind its unassuming facade lies a surprisingly expansive interior offering four bedrooms and four baths, including three bedrooms with three baths on the main level and a private upstairs bedroom with its own bath, ideal as a guest suite, apartment-style retreat, or income-producing space. An additional office or flex space off one of the bedroom suites allows work and relaxation to coexist effortlessly. The single-level main floor is designed with intention each bedroom enjoys privacy while remaining easily accessible. Interior details include travertin

This exceptional 6-dwelling unit redevelopment opportunity perched atop Solares Hill, the 18' highest point in Key West, is practically shovel-ready and includes top-level planning & design that resulted in an issued building permit in 2024. Substantial renovation is already complete on four of the 1-bedroom units; only the single family house renovation and condo conversion remain. The current owner, an experienced developer, invested significant time and capital securing previous approvals with the assistance of seasoned local professionals to renovate and then convert the rentals to condos, including detailed architectural plans, local-attorney-prepared condominium documents, a proposed survey for the 5-6 unit condo development, detailed labor and materials cost projection by a local licensed contractor for the construction of the house, and full submittal documents and a building permit issued in early 2024. The only thing missing is a new buyer ready to complete the process. The p

Real possibility for 2nd bath, call listing agent. *. Secret Garden Cigar Maker's Cottage in Old Town Tucked behind a private gate on a quiet section of Old Town in Key West, this enchanting 2-bedroom historic cottage invites you into a hidden world of tropical beauty, offering a rare blend of privacy, charm, and walkable island living-set in an X flood zone for added peace of mind. Follow a palm-lined path into a lush, private garden oasis filled with orchids, vibrant blooms, and softly glowing evening light. The outdoor pavilion and private deck create an effortless indoor-outdoor lifestyle-complemented by a spa-inspired retreat space designed for open-air relaxation, cooling rinses, and tranquil moments under the palms. Perfect for relaxing, entertaining, or simply enjoying the Key West breeze. Inside, vaulted ceilings, natural light, and original Cuban tile details reflect the home's 1890 cigar-maker heritage, while the updated kitchen features quartz countertops, stainless steel a

Discover the charm of what was once a carriage house and now a single-level home nestled in the highly desirable Meadows neighborhood of Old Town Key West. This inviting 3-bedroom, 2-bath residence blends historic character with modern updates, offering the quintessential island lifestyle. Effortless indoor-outdoor living defines this home, which features an open, airy feel that flows seamlessly to a private backyard oasis. The renovated kitchen features quartz countertops, modern finishes perfect for entertaining or everyday living. A versatile bonus loft provides the ideal space for a home office. Step outside to your own tropical retreat, complete with a sparkling pool surrounded by a spacious brick patio, cabana bar, fabulous outdoor shower and mature landscaping that creates privacy and a lush island ambiance. Topped off with off-street parking, whole house generator, x flood zone and close proximity to everything that makes Key West living so special, while still providing a peac

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 i

Charming Multifamily Compound in Historic Key West, Florida. Discover the allure of old historic Key West with this exceptional multifamily compound, perfectly situated in a vibrant neighborhood. This property offers a unique blend of charm and modern comfort, making it an ideal investment or family retreat. The compound consists of 4 units, each exuding the distinctive character of Key West architecture, featuring high ceilings, large windows that invite natural light. The main house has its own private heated pool, hot tub and outdoor shower perfect for relaxation and entertainment. The main house also has 2 guest cottages off the pool. The next building has an upstairs unit with 2 bedrooms and a bath with it's own private deck. Below is a one bedroom one bath unit and up front is the 3rd unit with one bedroom and one bath. Benefit from plenty of parking spaces, accommodating residents and guests with ease a rare find in this bustling area. Nestled in one of Key West's most historic

Luxurious, Modern, Historic, & Impeccably Remodeled. Welcome to 411 Louisa Street, located in the heart of Old Town Key West, less than a block from Duval Street's top dining and entertainment. This stunning five-bedroom, four-and-a-half-bath residence offers 3,663 sq. Ft. of living space on an 8,227 sq. Ft.oversized lot, providing rare space and privacy in one of the island's most desirable neighborhoods. Enter through the white picket fence and tropical courtyard to your grand Key West estate, where every detail has been thoughtfully designed. The first floor is set for entertaining, featuring a spacious living area and a chef's kitchen with stone countertops, an oversized island, custom cabinetry, and premium Sub-Zero, Viking, and Wolf appliances. A generous walk-in pantry adds extra storage convenience. The primary suite, also on the ground level, overlooks the pool and boasts a spa-inspired bath with dual showers, a freestanding soaking tub (with air bubble massage) and a large wa

Unmatched Old Town Opportunity! Location, Location, Location! This is your chance to own one of the most coveted properties in Old Town Key West-a truly unique home and lot that must be seen to be fully appreciated. Tucked away and completely hidden from view, this remarkably private property is the only single-family home currently on the market with direct pedestrian access to Duval Street via a charming walking lane. Step behind the gate and be transported into your own secluded tropical oasis. With a generous 4,200 sq ft lot, there's ample room to add a pool or expand, creating your ideal island retreat. Zoned as a non-contributing structure with HARC (buyer to verify), the home offers incredible potential as a restoration or redevelopment project. Permitted for Transient License Receivership HRCC1 (buyer to verify), this is a rare find in a premier location. First time ever offered for sale-don't miss this exceptional opportunity!

These properties rarely come on the market. Great opportunity to own an income producing Townhouse in the heart of Old Town Key West. This one bedroom Townhouse has a Transient License and is able to be rented on a nightly basis. Strong Rental History with many repeat clients. Just steps from Famous Duval Street. Located in a private gated community. Beautifully landscaped grounds with a fabulous Spa Pool complete this Tropical Oasis. There is a shared coin laundry facility for the complex