Refine Search
Map
Sort by
1230 5th St, Key West
$1,385,000
3 Beds ⋅ 4 Baths ⋅ 619730 MLS
Centrally located to everything Key West has to offer, and tucked behind a concrete privacy wall on a lush, tropical corner lot, this Midtown Key West property makes a statement the moment you step through the gate. A private courtyard filled with vibrant flowers and mature landscaping immediately sets the tone, leading you to a spacious home full of character and personality! Built with a metal roof, hurricane impact windows and doors, and thoughtfully updated throughout. The functional layout prides itself on easy indoor-outdoor living, effortlessly flowing from the living areas and out to the pool, patios, and guest cottage. The kitchen and dining area are truly made for entertaining, mimicking a chef's kitchen offering generous counter space, ample storage, a bar setup, and abundant natural light pouring in. Step outside to a sunny patio and resort-style pool, perfect for lounging or hosting. Alongside, you'll find a separate guest cottage offering a perfect multi-purpose space. Each bedroom features its own en suite bath, including a spacious primary suite with a walk-in closet, custom built-ins, and your very own private treetop balcony. Additional guest suites are thoughtfully positioned on both levels, including one with its own private entrance. Rich details set this home apart, including Dade County Pine accent walls, stone flooring and bathrooms, multiple balconies, patios, and an outdoor shower. Can be offered turnkey and fully furnished. Additional upgrades include new central AC, high-quality custom awnings, shade sails, a heavy duty storage shed, irrigation system, gutters, and new kitchen appliances.

1230 5th St, Key West
1215 Margaret St, Key West
$1,380,000
3 Beds ⋅ 3 Baths ⋅ 619721 MLS
Enjoy the perfect Key West location - Old Town bordering the Casa Marina neighborhood - in this 3 bedroom, 2.5 bath pool home. You'll have peace of mind knowing that the home was completely renovated from the ground up in 2019 while keeping with the historic style of the home's origins - tongue in groove ceilings, wood floors, pecky Cypress wall accent - but adding modern amenities such as impact windows, stainless steel appliances, granite countertops, tankless water heater, in-home laundry. The Main Home has an en suite Primary Bedroom; Guest Bath accessible from the hallway and Guest Bedroom; open concept Kitchen and Family Room with vaulted ceiling and a wall of sliding glass panels overlooking the pool courtyard. Opposite the pool is the Guest Cabana with Half Bath and Outdoor Shower. The property has been offered as a vacation rental and also kept part time for the owner's use. Close to everything you could want in Key West - around the corner from world famous El Siboney Cuban Restaurant, 2 blocks from Truman, 4 blocks from Duval St., a quick walk to Higgs Beach and the White Street Pier. Home is being offered turnkey furnished. Located in Flood Zone X so no flood insurance required.

1215 Margaret St, Key West
1501 Government Road, Key West
$1,350,000
618614 MLS
Discover an exceptional opportunity at the Key West Urgent Care location, situated at 1501 Government Rd, Key West. This strategically positioned building is not just a healthcare facility; it represents a cornerstone of community health services in a vibrant, bustling area. **Property Highlights:** - **Prime Location**: Nestled in a high-traffic area, this property benefits from excellent visibility and accessibility, attracting both local residents and tourists alike. - **Versatile Building**: The structure is designed to accommodate urgent care services, featuring multiple examination rooms, administrative offices, and patient waiting areas. Its layout allows for easy modification to suit various medical or commercial uses. - **Expansive Land**: The property sits on a generous plot which may provide space for expansion or additional facilities. This flexibility opens the door for a range of future developments, whether for healthcare or other commercial ventures. - **Community Focus**: As a well-established urgent care center, it has built a strong reputation within the Key West community, offering essential healthcare services and fostering loyalty among patients. - **Growth Potential**: The increasing demand for healthcare services in the area presents significant growth opportunities. Investing in this property means tapping into a vital market with a promising outlook. - **Scenic Surroundings**: Key West is renowned for its stunning landscapes and rich culture, making this location not only functional but also appealing to those who appreciate the unique charm of island life. This is more than just real estate; it's an investment in the health and well-being of the community. Whether you're looking to continue the legacy of urgent care or explore new ventures, 1501 Government Rd is a prime choice of a building for your next project.

1501 Government Road, Key West
830 Fleming St, Key West
$1,350,000
3 Beds ⋅ 4 Baths ⋅ 615754 MLS
NEW PRICE!!! First time on the market since the mid 70s! Prime Old Town Location mixed-use property. Endless possibilities with this corner location in the heart of the historic district and just two blocks from the Seaport. Commercial space with full bath and occupied by successful gallery tenant. Three Residential apartments with 1BED/1BATH each. Corner of Fleming and Margaret St near shopping, dining, and galleries. City has two Non-transient residential rental licenses for this property and one commercial license. (Water meter: 1 Electric Meters: 3) Low assumable flood insurance $1053/year! Appt. Only-Please do not disturb businesses/tenants.

830 Fleming St, Key West
101 Front St Unit 8, Key West
$1,345,000
2 Beds ⋅ 3 Baths ⋅ 615636 MLS
This beautifully updated Foundry townhome in the exclusive gated Truman Annex community is a dream come true! The floor to ceiling windows and doors at the entry allow sunshine to filter into the main floor living space creating a bright and airy space. The main floor has 11 foot ceilings and double French doors that open to the private front courtyard and porch. The open floor plan allows for an easy flow from living space to dining room to kitchen. The stainless steel appliances include a microwave and dishwasher that were installed new in 2024 and barely used. The half bath is located on the first floor for convenience. Make your way up the stairs to the primary suite, located on the second floor, with an en suite bath and walk in shower. Enjoy morning coffee on your private balcony. The washer and dryer are located on this floor and were installed new in 2024. The floor to ceiling French doors and windows allows light to encompass the space. The guest suite is located on the third floor with an en suite bath and shower tub combo. The wall to wall windows allow natural light to flood the room. This home has a designated off street parking spot for 1 vehicle located just out front of the private courtyard. The Foundry swimming pool is a short walk away. This townhome is just down the block from Truman's Little White House, and is an easy walk or bicycle ride to Ft. Zachary Taylor Park, The Coffee Butler Amphitheater and the Truman Waterfront, as well as the world famous Mallory Square and Duval St. Home has been mostly owner occupied but is turnkey for a luxury vacation rental.

101 Front St Unit 8, Key West
213 Golf Club Dr, Key West
$1,340,000
3 Beds ⋅ 3 Baths ⋅ 620936 MLS
For Statistical Purposes: Life is GRAND in The Sanctuary @ Key West Golf Club! Beyond the 2nd set of gates, this exclusive private enclave is home to all-single-family residences. Beautifully maintained, surrounded by lush tropical foliage, this pristine home enjoys an enviable setting along #18 fairway, complete w/private pool, 4 verandas, off-street parking, carport & adjacent storage shed. Inside, a stunning fully renovated kitchen is truly a Chef's Dream, featuring all upgraded stainless appliances, expansive quartz countertops, floor-to-ceiling Kraft Maid custom cabinetry, Subway tile backsplash, upgraded lighting. The open living spaces flow beautifully to the outdoors. A versatile 10' x 12' den off the living room offers an ideal home office/potential 4th sleeping space w/addition of a closet/armoire. A convenient powder room completes the main level. The outdoor setting is equally impressive. Gorgeous Azek/Trex decking enhances the front veranda/steps, while the poolside retreat features the same beautiful low-maintenance, beautiful composite decking/steps/expansive pool deck. Lush gardens accented by river rock surround the front/side/rear yards, creating exceptional tropical privacy. Western exposure from the rear veranda and poolside setting provides the perfect backdrop for catching Key West's spectacular sunset colors. Upstairs, the spacious primary suite features vaulted ceilings, a beautifully renovated bath and French doors opening to a large private veranda nestled among the treetops. Two lovely guest bedrooms each enjoy French doors leading to the open veranda overlooking the peaceful promenade, and the guest bath has also been tastefully renovated. Additional attributes include a freshly painted exterior/fencing with so much more. Sanctuary owners enjoy all the amenities of Key West Golf Club, including 24-hour Resident Services, onsite Community Management, Clubhouse/Fitness Room, two gorgeous community pools. Welcome home to your own Sanctuary!

213 Golf Club Dr, Key West
1515 Patricia St, Key West
$1,330,000
4 Beds ⋅ 2 Baths ⋅ 615869 MLS
Located in the heart of Midtown Key West, this beautifully renovated 4-bedroom, 2-bathroom home offers over 1,900 sq. ft. of stylish living space on a spacious 6,400+ sq. ft. lot. Recently updated within the past two years, the home features a stunning chef's kitchen, hurricane-rated impact windows and doors, a new roof, a heated pool, and covered off-street parking. The open-concept layout is perfect for entertaining, flowing seamlessly from the kitchen to the living areas and out to the backyard oasis. The primary suite boasts an ensuite bath and private access to the lush, tropical yard—your own serene retreat. Enjoy the best of island living just moments from beaches, fine dining, galleries, and all the charm of Old Town Key West. Mature tropical landscaping creates a private and inviting atmosphere, ideal for relaxing or hosting guests. Home is being sold turn key and furnished with the exclusion of artwork and personal effects.

1515 Patricia St, Key West
1616 Atlantic Blvd Unit 13, Key West
$1,325,000
2 Beds ⋅ 3 Baths ⋅ 619340 MLS
Wake up to the rhythm of the Atlantic Ocean and sweeping sunrise views in the gated oceanfront community of Casa Caselles. This renovated Key West townhome offers four covered balconies facing the ocean and effortless lock-and-leave coastal living in one of Mid-Town Key West's most desirable waterfront locations. 1616 Atlantic Blvd. #13 spans 2,016 sq. ft. across three levels, featuring high ceilings, abundant natural light, and open-concept living designed to capture ocean views and island breezes. The main living level showcases Atlantic Ocean views, a spacious living and dining area, and an updated kitchen with stone countertops, stainless steel appliances, and custom Hansen & Bringle cabinetry. An architectural staircase anchors the home while large sliding doors open to covered balconies ideal for outdoor dining, morning coffee, or evening cocktails overlooking the water. The top floor features two spacious en-suite bedrooms, each designed for comfort and privacy, along with laundry on the bedroom level, dual-zone A/C, and generous storage throughout. A private landscaped courtyard with irrigation creates a quiet retreat and houses the propane whole-house generator, while the carport-level workshop and storage area provides space for bikes, kayaks, paddleboards, and beach gear. Impact windows and doors provide storm protection and peace of mind. Residents of Casa Caselles enjoy resort-style oceanfront amenities, including a large heated saltwater pool overlooking the Atlantic, expansive sun deck with loungers and umbrellas, gated privacy, pet friendly spaces, and a relaxed waterfront atmosphere. Located in Mid-Town Key West, this home is steps from the beach, dog park, tennis and pickleball courts, restaurants, and the weekly farmers market--an ideal primary residence, vacation home, or low-maintenance island retreat. * Seller may offer owner financing with competitive terms for qualified buyers*

1616 Atlantic Blvd Unit 13, Key West
1019 Simonton St Unit 102, Key West
$1,325,000
2 Beds ⋅ 3 Baths ⋅ 616972 MLS
This Southernmost Cabana Townhome is a meticulous 2 bedroom, 3 bath furnished unit in the sweet hidden enclave of only 21 homes. This property is tucked away very near Duval which allows for the peace and quiet desired when not being involved in all of the local fun that only Key West offers. Included is its own designated covered parking space as well as a location very near the peaceful pool and water feature. Open floor plan with fresh and light interior selections. Offering a King in the primary bedroom and a queen with a reading area in the guest bedroom. Both offer ensuite full baths. Front and rear porches for your relaxation and pet(s) if so needed. Located in the X Flood zone, impact glass all around. Perfect for a vacation home or a rental property. You can walk out your door and across the street to enjoy Key Wests fine dining, Art exhibits and local color! This is a very sweet choice for all you need in Key West.

1019 Simonton St Unit 102, Key West
419 Simonton St Unit A, Key West
$1,325,000
2 Beds ⋅ 3 Baths ⋅ 618250 MLS
The rare kind of antiquity that comes with all the comforts of today. Built before 1889 and reimagined for modern living, 419 Simonton Street A captures the true spirit of Old Town Key West—authentic, refined, and timeless. Once a mixed-use landmark with a flower shop below and a residence above, the home has been meticulously restored and reimagined from the ground up, with construction completed in January 2026 and every system, surface, and finish entirely new. Offered fully furnished with a bespoke interiors program by Ben Teague Design, the residence is layered with thoughtful selections, timeless materials, and a quiet sophistication that feels both intentional and effortlessly livable. The home offers two bedrooms and two-and-a-half baths, including an upstairs primary bedroom that opens to a classic Key West porch, while a second porch downstairs extends the living space and reinforces the home's effortless indoor-outdoor rhythm. Architect-led design and professionally curated landscaping elevate the curb appeal to a truly top-tier example of Old Town style—timeless proportions, thoughtful detailing, and a presence that feels historic without feeling precious. The property is part of a thoughtfully structured HOA, which also includes one attached residential unit positioned to the rear of the main home, as well as a separate detached unit located at the back of the property—allowing for shared stewardship while preserving privacy and architectural integrity. Set on one of the highest elevation blocks in Old Town and located in the coveted X-500 flood zone, this is a rare opportunity to own a home where heritage, design integrity, and modern peace of mind converge on one of Key West's most iconic streets.

419 Simonton St Unit A, Key West
320 Margaret St, Key West
$1,325,000
3 Beds ⋅ 2 Baths ⋅ 618237 MLS
This classic Conch home, dating back to the 1920s, is ready for your personal touch. Located in the heart of Old Town, it is close to the Historic Seaport and only a few blocks from Duval Street. The property includes a POOL and PARKING. It is a two-story residence that has been cherished by the same owners for decades. The spacious living and dining areas are complemented by a kitchen featuring walk-in pantry space. A sizable laundry room adds convenience, and the main floor provides easy access to the pool deck and backyard. There is a full bath on the first floor. The second level boasts three generously sized bedrooms and a half bath that can be easily transformed into a full bath. This home is conveniently close to dining, shopping, coffee shops, and much more!

320 Margaret St, Key West
1719 Atlantic Blvd, Key West
$1,320,000
3 Beds ⋅ 2 Baths ⋅ 616693 MLS
Location, Location, Location. Just a stones throw away from the Atlantic Ocean. Gorgeous 3BR/2B with bonus room/home office. Updated open floor plan with stunning kitchen and baths. NEW landscaping & turf, HVAC (2025) flooring, paint, Tesla charger & fans. Parking for 2 private driveway and tons of street parking. Property sits behind a privacy wall and encompasses an entire block with a heated saltwater pool and turf yard that make it a private oasis! Just a few minute walk to Smathers & Higgs beaches, White St. pier, pickleball courts and the dog park! A true Key West GEM!

1719 Atlantic Blvd, Key West
1107 Olivia St, Key West
$1,300,000
2 Beds ⋅ 2 Baths ⋅ 618079 MLS
Located on the desirable 1100 block of Olivia Street near the cemetery, this updated two bedroom, two bathroom, two story Conch home offers a balanced blend of Old Town character, privacy and walkability. This property is in the X flood zone and includes a pool and off street golf cart parking. This 1,125 square foot layout includes one bedroom and full bath on the first floor. The upstairs primary suite offers a full bath and direct access to a large private sun deck. The kitchen is generously sized for the home and opens to the main living area, with bar seating for four. Two sets of French doors in the living room open to the private backyard, allowing for indoor and outdoor use. The outdoor space is fully landscaped with mature trees and plants and includes a heated cocktail pool, outdoor dining area and additional side yard storage. A covered front porch faces Olivia Street and provides usable outdoor seating for morning coffee. Off street parking accommodates a six seater golf cart. The home is within easy walking distance to the harbor, dining and downtown Key West. Owner occupied full time for the past ten and a half years. Well suited for a primary residence, seasonal home or vacation rental in one of Old Town's most recognizable areas.

1107 Olivia St, Key West
1113 Watson St, Key West
$1,300,000
5 Beds ⋅ 3 Baths ⋅ 618191 MLS
Historic Old Town Key West Duplex | Income-Producing Island Opportunity Discover the timeless charm of Old Town Key West in this truly unique and character-rich historic duplex, offering both lifestyle flexibility and excellent income potential. Filled with authentic island personality, this property is ideal for an owner-occupant, investor, or anyone seeking the classic Key West way of life. The downstairs residence features a spacious three-bedroom, two-bath layout highlighted by a large screened-in porch, perfect for morning coffee, cooling island breezes, and relaxed evenings. An outdoor yard provides a rare Old Town bonus, offering space for entertaining, pets, or simply enjoying the tropical surroundings. Upstairs, a separate two-bedroom, one-bath apartment offers privacy and charm, making it well suited for long-term rental, guest accommodations, or supplemental income. The flexible configuration allows you to live in one unit while renting the other, creating an ideal live-work-rent opportunity in a highly desirable location. Off-street parking for up to three vehicles is a true Old Town luxury, and a shared laundry area adds everyday convenience. Distinctive architectural details throughout reflect the historic character and quirky charm that define Old Town Key West. Whether you are seeking a smart income-producing investment, a multi-generational living arrangement, or a home that captures the spirit and history of the island, this duplex offers endless possibilities in one of Key West's most sought-after neighborhoods. Use as a single family home for a large family! Classic, unique, and income-ready, this is a rare opportunity to own a genuine piece of Old Town Key West.

1113 Watson St, Key West
1018 Truman Ave, Key West
$1,300,000
5 Beds ⋅ 7 Baths ⋅ 618332 MLS
Prime mixed-use investment opportunity in the heart of Key West. This well-maintained historic building features two commercial units on the ground floor with excellent visibility and foot traffic, plus five 1-bed, 1-bath residential units upstairs, creating high, diversified income. The property offers classic Old Town character with functional updates, multiple electric meters, and solid rental performance. A rare side yard and covered upper porch add additional tenant appeal. Fully leased to established tenants, this turnkey asset is ideal for investors seeking stable cash flow in a highly desirable location, just minutes from Duval Street, beaches, and Key West's top dining and entertainment.

1018 Truman Ave, Key West
247 Golf Club Dr, Key West
$1,300,000
3 Beds ⋅ 3 Baths ⋅ 616002 MLS
Tucked inside the private gates of The Sanctuary at the Key West Golf Club, 247 Golf Club Drive is a true standout. This freestanding residence sits on a large lot with sweeping views of the lush fairways and tranquil lake, offering privacy, serenity, and unmatched outdoor living. Thoughtfully upgraded and well maintained, this tropical retreat boasts brand-new hurricane rated Bahama panels, a heated pool, and an elegant bricked patio surrounded by lush, tropical landscaping. Whether you're rinsing off in the outdoor shower after a swim or sipping cocktails under the palms, every inch of this yard was made to enjoy. Step inside to warm hardwood floors and an airy, open layout that invites you in. The heart of the home is a stylish kitchen featuring granite countertops, stainless steel appliances, and updated cabinetry. It opens effortlessly into the bright living area, where French doors lead to a screened-in porch—perfect for relaxing and overlooking your private backyard retreat. Downstairs, a flexible bonus room—currently used as a den—can easily be converted into a 4th bedroom, home office, or dining area. Upstairs, the primary suite is your private escape, featuring a spacious veranda perfect for sipping your morning coffee or soaking in the island breeze. Two additional bedrooms—each sharing a front balcony and a beautifully updated bathroom. A covered carport and extra off-street parking, a front porch, and a fully fenced backyard complete this luxurious offering. Residents of The Sanctuary enjoy exclusive access to two resort-style pools, a fitness center, 24-hour security, and beautifully maintained tropical grounds—all just minutes from Old Town Key West. Your tropical retreat is ready. All that's missing is you.

247 Golf Club Dr, Key West
1011 Truman Ave, Key West
$1,300,000
2 Beds ⋅ 3 Baths ⋅ 617055 MLS
1011 Truman Avenue is a versatile Old Town opportunity that can easily live like a spacious single-family residence while offering great flexibility for guests or multi-generational living. Currently configured as three legal units with one covered off-street parking space and located in the desirable X-Flood Zone, the property features a 795 sq. ft. ground-floor space with an industrial feel and half bath that could be reimagined as additional living, entertaining, or hobby space, plus a 416 sq. ft. one-bedroom with full bath and kitchenette hookups—ideal for an efficiency or guest suite. Upstairs, a stunning 720 sq. ft. one-bedroom, one-bath loft feels like a private primary retreat with open living and dining areas, a partitioned bedroom, beautiful master bath, full kitchen, and a private covered patio. Together, the spaces create a unique opportunity to design a large Old Town Key West residence with flexible layouts for guests, extended family, or live/work use.

1011 Truman Ave, Key West
1202 Whitehead St, Key West
$1,300,000
3 Beds ⋅ 2 Baths ⋅ 617908 MLS
This beautifully restored old Key West home offers the perfect tropical escape. Located just a block from Duval Street, Garden of Roses combines historic charm with modern upgrades, making it an ideal vacation home. Currently being rented as a monthly vacation rental! Enjoy a spacious layout with 3 bedrooms, a high-end kitchen, and bright, open living areas. Relax outdoors with a private hot tub, lush gardens, and multiple seating areas. The home also features off-street parking, hot tub, lusciously landscaped patio for entertaining or outdoor dining. Located right in the heart of Old Town Key West, just steps from the Southernmost Point and Duval Street, this home offers the perfect blend of comfort and convenience. Schedule your showing today to experience this slice of paradise!

1202 Whitehead St, Key West
1224 Flagler Ave, Key West
$1,295,000
5 Beds ⋅ 4 Baths ⋅ 617518 MLS
Step onto the grounds of 1224 Flagler Avenue and discover a versatile property brimming with possibility. This legal duplex with an additional private mother in-law suite offers flexible living arrangements and exceptional rental income potential. It's an ideal opportunity for investors, multi-generational households or anyone seeking both comfort and return. Unit B, on the right, is a stylishly updated 2 bed/1bath home featuring new flooring, a renovated kitchen with stainless steel appliances, and its own washer and dryer. Offered fully furnished and turnkey, it opens to a charming shared backyard perfect for outdoor dining, lounging, or enjoying the Key West breeze. Tucked into the back corner is the separate 1 bed/1bath mother-in-law suite, complete with its own entrance. Whether used for guests, extended family, or additional rental income, this private space adds valuable versatility. On the left, Unit A offers a comfortable 2 bed/2 bath layout with tile floors throughout, a functional kitchen with island seating, glass doors leading to a private fenced backyard, and its own washer and dryer. With a light refresh, it can easily transform into a delightful long-term residence or sought-after rental. Fully fenced along the back and side yard, the property feels tucked away yet remains moments from beaches, shops, schools, and all the charm of Old Town. Blending flexibility, strong income potential, and space to customize, 1224 Flagler Avenue is a rare Key West find perfectly suited to meet your needs while generating multiple revenue streams.

1224 Flagler Ave, Key West
4 Aronovitz Ln, Key West
$1,275,000
3 Beds ⋅ 3 Baths ⋅ 618423 MLS
Experience an authentic island lifestyle at this classic conch cottage nestled in the heart of Old Town. Located on a quiet lane, just steps to Duval Street and The Green Parrot, this updated home provides a unbeatable location for walking to all of the best spots in Key West. Designed in the iconic ''conch cottage'' style, the interior features Dade County Pine walls, vaulted ceilings, and modern appliances. Enjoy the ease of main-floor living with two bedrooms--each paired with a dedicated bathroom--complemented by a versatile loft space featuring the third bedroom and bathroom. The private, fully fenced outdoor space is surrounded by lush tropical greenery and offers the perfect outdoor dining setting. The front porch provides a discrete vantage point to enjoy morning coffee or evening cocktails while watching the world go by on Aronovitz Lane. Newly installed impact rated doors and windows, a newer roof (replaced in 2021), and X flood zone location keep insurances very reasonable. Offered fully furnished and with years of monthly vacation rental history, this home is ready for it's next owner, weather as a Winter home, full-time residence, or investment property.

4 Aronovitz Ln, Key West
720-726 Emma St, Key West
$1,275,000
8 Beds ⋅ 10 Baths ⋅ 615510 MLS
Unique opportunity for a creative buyer to own this 3 residential unit property. Would be a great for business owner looking for employee housing. Update all 3 homes for a family compound. Currently setup as roommate style living with a gross income of $15,000. a month. Don't miss this great location in Bahama Village steps from the Truman Waterfront, Ft. Zach beach, restaurants, galleries, shops and more!

720-726 Emma St, Key West
2211 Staples Ave, Key West
$1,270,000
4 Beds ⋅ 4 Baths ⋅ 618756 MLS
Renovated Midtown retreat offering exceptional flexibility, thoughtful updates, and the ideal layout for modern island living. Elevated and designed for comfortable one-level living, this 4 bedroom, 3.5 bathroom home features a versatile floor plan. At the heart of the home, the newly renovated kitchen blends style and functionality with a large center island, custom cabinetry, granite countertops, and a high-end appliance package. Privately situated at the rear of the property, the fully equipped guest cottage includes a kitchenette, living area, and full bath, offering excellent flexibility for guests, extended family, or potential rental use. An additional studio space adjacent to the pool is ideal for a home office, art studio, fitness room, or wellness retreat. The sun-filled patio and pool provide the perfect setting for relaxing afternoons or hosting weekend gatherings, while the spacious lot offers ample off-street parking for vehicles and a golf cart. Ideally located just minutes from shopping, dining, and schools, this property offers a peaceful residential setting with convenient access to everything Midtown has to offer. With its combination of updated interiors, multiple living spaces, and resort-style outdoor amenities, 2211 Staples Avenue presents a rare opportunity to enjoy space, comfort, and versatility in the heart of Key West.

2211 Staples Ave, Key West
800 Fleming St Unit B-3, Key West
$1,270,000
2 Beds ⋅ 2 Baths ⋅ 617634 MLS
Perfectly situated just three blocks from Duval Street and two from the grocery store, this one-of-a-kind, fully furnished penthouse has been meticulously renovated to deliver unmatched luxury living in the heart of Old Town Key West. Offering rare off-street parking, this light-filled residence is perched among the treetops and features a private balcony with serene pool and garden views. Inside, you'll find soaring ceilings, warm hardwood floors, Dade County pine accent walls, and impact-resistant doors that blend historic charm with modern comfort. The chef's kitchen is thoughtfully designed with Corian countertops, Miele appliances, an induction cooktop and convection oven, a breakfast bar ideal for dining or entertaining, and generous pantry space. The same Corian surfaces extend into the bath for a cohesive, upscale finish. A Miele washer and dryer add convenience to everyday living. The open floor plan flows seamlessly from the kitchen to the dining and living areas, creating an inviting space for relaxing or hosting guests. Original stained-glass transom windows add a touch of timeless character, reflecting the home's historic roots while complementing its modern updates. This lovingly restored condominium includes an assigned parking space, secure building access, and beautifully maintained common grounds featuring lush landscaping, a sparkling pool, sundeck, and patio area.

800 Fleming St Unit B-3, Key West
907 United St, Key West
$1,254,750
3 Beds ⋅ 3 Baths ⋅ 620423 MLS
A welcoming covered front porch sets the tone for this exceptional townhome, offering the perfect place to enjoy your morning coffee or unwind with an evening cocktail while embracing the island breeze. Timeless craftsmanship meets modern comfort in this beautifully designed 3-bedroom, 3-bathroom townhome, thoughtfully created for effortless living, exceptional functionality, and relaxed tropical elegance. Step inside to a generous entry foyer that offers endless possibilities--ideal as a home office, sitting room, or welcoming reception space. The open-concept floor plan seamlessly connects the chef's kitchen, dining area, and living room, creating an inviting space for everyday living and entertaining. The custom kitchen is appointed with quality cabinetry and high-end appliances sure to impress. The spacious primary suite is conveniently located on the main level, offering privacy and the ease of single-level living. Upstairs are two additional guest bedrooms and a full bath, complemented by hardwood flooring, while the first floor showcases classic Mexican tile that adds warmth and island character. Step outside to your secluded backyard oasis. Surrounded by lush tropical landscaping, the heated pool and spa with a tranquil water feature create the perfect setting for relaxation. Multiple outdoor living and entertaining areas provide ample space for dining al fresco, hosting family and friends, or simply enjoying the peaceful surroundings. Built with durable Indian block construction, this exceptional home offers lasting quality and timeless appeal in the X500 zone. Whether you're searching for a full-time residence, vacation getaway, or investment property, this townhome delivers the perfect blend of luxury, privacy, and tropical living.

907 United St, Key West
249 Golf Club Dr, Key West
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 618107 MLS
Great House in the Key West Golf Club. Enjoy your own private pool, or join in the fun at one of the communities pools. This home features an open floor plan with kitchen, dining area, living area, half bath and a den. New impact sliding doors open to the private rear porch deck and pool. Upstairs is the primary bedroom ensuite, two guest bedrooms with another full bath in the hall. New impact windows and doors throughout.

249 Golf Club Dr, Key West
415 Julia St, Key West
$1,250,000
3 Beds ⋅ 4 Baths ⋅ 612090 MLS
At the best location in the heart of old town you will find this great duplex on Julia street in between Duval street and Whitehead street, 86 FOOTSTEPS TO DUVAL STREET. The back is a two bedroom two bathroom with a nice back yard. And in the front is a recently renovated one bedroom with two bathrooms with high ceilings and a great loft. It has an outdoor shower. A new A/C was installed 01/24. When you are sitting on your front porch it's hard to believe that you are in between the two busiest streets as Julia street is a really quiet and cute street! Don't miss out on this great opportunity!

415 Julia St, Key West
1616 Atlantic Blvd Unit 5, Key West
$1,250,000
2 Beds ⋅ 3 Baths ⋅ 617125 MLS
Rare Luxurious Atlantic Oceanfront Concrete 3 story home. 2 Bedrooms 2 1/2 bathrooms located in a private gated community. Ocean views from your balconies. This exquisite home has stainless steel appliances, custom cabinetry, vaulted ceilings, tiled carport, oversized well-manicured, private back yard. Huge storage room with built in shelving. This rare unit has the largest backyard in the community and an extra private parking space. These are just a few of the amenities this lavish fortress offers. Casa Caselles is located directly on the Atlantic Ocean between 2 nature preserves with a quaint Mediterranean feel and offers a front row seat to breathtaking sunrises and wildlife. The pool is beachside and allows its owners VIP seating for star gazing, fireworks and watersports. This 20 home complex is owner occupied only. No rentals are allowed. Schedule your private showing now. No rentals allowed. Owner financing is available.

1616 Atlantic Blvd Unit 5, Key West
528 Porter Ln, Key West
$1,245,000
2 Beds ⋅ 3 Baths ⋅ 617883 MLS
Turnkey, furnished luxury townhome on quiet Porter Lane in the desirable Truman Annex, offering an effortless lock and leave lifestyle in the heart of historic Key West. Completely gutted and redesigned in 2022, this impeccably renovated residence blends refined finishes with modern systems throughout. Updates include a new HVAC system, on-demand hot water heater, all new kitchen appliances. Wide-plank luxury vinyl flooring runs throughout the home and staircase, complemented by white wood trim and a natural wood -accented stairway wall. Ensuite bathrooms feature new ceramic tile, custom cabinetry, modern fixtures, glass-enclosed showers and updated plumbing fixtures. Sparkling designer kitchen showcases waterfall quartz countertops, Italian Carrara marble tile backsplash, new cabinetry and high-end appliances, along with three leather barstools with gold accents. This home is professional furnished with curated, high-end decor, including a living room with sleeper sofa and high performance-fabric seating. First floor powder room features tropical-inspired wallpaper and new fixtures. Dining area offers seating for six with stunning round table and leather chairs. Both bedrooms located on second floor, with primary suite featuring a king bed, ensuite bath and private outdoor seating. The guest suite also offers an ensuite bath, queen bed, owners closet and private outdoor seating. Washer and dryer are conveniently located on second floor between both bedrooms. Outdoor living is enhanced by four seating area, including a front porch, private bedroom balconies and a rear porch with dining table overlooking a new stone paver patio and lush tropical landscaping. New awnings provide added comfort and sun protection. One off street parking space included and conveniently located adjacent to patio entrance. 528 Porter Lane offers the perfect balance of privacy, convenience and luxury and only a short stroll to all the action Key West has to offer.

528 Porter Ln, Key West
833 Eisenhower Dr Unit 303, Key West
$1,225,000
2 Beds ⋅ 2 Baths ⋅ 603597 MLS
Closest living to OLD TOWN with a boat slip!! Peace and quiet and a boaters delight! This small condo complex located in the beautiful Meadows neighborhood has an ordinance against vacation rentals which ensures consistent tranquility with a virtually private pool. One of the only properties close to Old Town where you can keep your boat in the water with an assigned boat slip. With the rising cost of boat slips and marina rates, the slip can save you upwards of a $1000 per month. This third floor 2BR/2BA unit allows for panoramic views of the marina and Key West. The property has had many upgrades during this ownership including new decorative floors with a coastal feel, an upgraded bathroom, new AC, washer and dryer, and some appliances. Enjoy entering a cool car with the covered parking, a rare find in The Meadows. Large private exterior storage space is included. The views are a must see!

833 Eisenhower Dr Unit 303, Key West
1718 United St, Key West
$1,215,000
3 Beds ⋅ 3 Baths ⋅ 616195 MLS
Welcome to 1718 United Street, a beautifully renovated home in the heart of Key West offering modern comfort with timeless island charm. This spacious residence features 3 bedrooms and 2.5 bathrooms, including a stunning spa-style master bath with double sinks and dual shower heads for the ultimate retreat. The bright and open layout showcases elegant marble countertops, thoughtfully designed finishes, and inviting living spaces perfect for both relaxing and entertaining. Step outside to enjoy the side porch facing the driveway, an ideal spot for morning coffee or evening gatherings. A standing seam metal roof adds both style and durability, giving peace of mind for years to come. To enhance the island lifestyle even further, the seller has drawings available to the buyer for a pool and tiki hut, offering the opportunity to create your own backyard oasis. Ideally located just a short bike ride to the vibrant energy of downtown Key West and world-famous Duval Street, this property combines convenience, comfort, and style—move-in ready and waiting to be enjoyed as your new island home.

1718 United St, Key West