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Browse All Key West FL Above $1M Properties for Sale

$1,750,000
3 Beds ⋅ 2 Baths ⋅ 619504 MLS
Discreetly tucked within the storybook streets of the coveted Meadows, this enchanting Key West residence is a rare expression of timeless elegance and island sophistication. Rich in history yet effortlessly refined, the home invites you into a world where classic Conch architecture meets curated, modern luxury. From the moment you enter, the ambiance is unmistakable--soaring ceilings, warm Dade County Pine, and bespoke craftsmanship create an atmosphere that is both grand and inviting. Every space has been thoughtfully composed, balancing texture, light, and artistry to deliver a home that feels as beautiful as it is livable. Beyond the interiors, a private tropical sanctuary unfolds. Surrounded by lush greenery and designed for complete seclusion, the poolside setting evokes a boutique resort experience. Whether basking in the sun, enjoying the gentle sound of water, or hosting intimate evenings under the glow of ambient lighting, this outdoor retreat is nothing short of extraordinary. The upper-level primary suite offers a serene escape, complete with its own sitting area and a covered balcony that captures the essence of relaxed island mornings and golden-hour evenings. Guest accommodations are equally inviting, offering comfort, privacy, and flexibility for hosting family or discerning visitors. Offered turnkey, the home presents a seamless opportunity for immediate enjoyment--whether as a private coastal retreat or a high-performing luxury rental. Every detail has been considered to ensure effortless living without compromising character or authenticity. Just moments from the vibrancy of Old Town, yet worlds away in feel, this is a residence that embodies the true spirit of Key West--elegant, intimate, and undeniably captivating.

1319 Newton St, Key West
$3,398,000
3 Beds ⋅ 4 Baths ⋅ 619475 MLS
Your Dream Waterfront Oasis Awaits! Immerse yourself in refined elegance in this 3-bedroom, 4-bathroom sanctuary. The crown jewel of this residence is the unparalleled canal frontage, complete with a new 24k lb boat lift and ~58' of new seawall, offering seamless ocean access. Step inside to experience the spacious living areas, illuminated by tons of natural light, with tile flooring throughout. Marvel at the attention to detail in the updated kitchen featuring a waterfall island and all new stainless steel appliances. Outside, a heated salt pool, equipped with automation and a water feature, invites you to unwind amidst the lush turf and enchanting landscape lighting. Relish in unparalleled privacy with a comprehensive privacy wall and fencing, enhanced by a Mosquito Nix system for a pleasant outdoor experience. Enjoy the added conveniences of a whole-house automatic generator and on-demand gas water heater. Nestled in an environment that offers the best waterfront living, your lifestyle is enhanced by limitless opportunities for boating and fishing--right from your backyard: automatic front gates, circular driveway, and awning-covered parking round out this unparalleled offering. Elevate your life with this matchless blend of luxury and oceanic freedom!

3034 Riviera Dr, Key West
$2,999,999
4 Beds ⋅ 3 Baths ⋅ 619469 MLS
Key West Oasis - A Tropical Compound Steps from the Sea. House, Pool & Guest Retreat located near by Casa Marina and steps from Old Town. Welcome to your own private tropical compound just blocks from the beach, tennis and pickleball courts, and the iconic White Street Pier where you're perfectly positioned for sunrise strolls, sunset views, and everything in between. Nestled on a lush corner lot surrounded by swaying palms and vibrant tropical foliage, this property offers both privacy and proximity to the best of island living. The main house blends timeless Key West charm with modern comfort, featuring sunlit living spaces and breezy indoor-outdoor flow. Step outside to your resort-style backyard, where a sparkling pool is the centerpiece for relaxation and entertaining. The separate pool house offers flexible space for guests, a studio, or home office. Whether you're hosting sunset gatherings, enjoying a dip after a morning beach walk, or strolling to local shops and cafes, this is island living at its finest. Experience the perfect blend of tranquility, convenience, and tropical beauty—right in the heart of Key West. Here, mornings begin with the sound of the ocean in the distance, afternoons are spent floating in the pool, and evenings bring gatherings under starlit skies. This is more than a home—it's a slice of paradise in the heart of Key West. All you need is to move in and start living your Key West dream. Built with storm readiness in mind, the residence features hurricane-impact windows and doors, offering enhanced safety, sound reduction, and energy efficiency. Complementing these upgrades is a whole-house generator, delivering seamless power during outages and elevating everyday comfort with true peace of mind.

1501 White 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
$2,299,500
3 Beds ⋅ 4 Baths ⋅ 619404 MLS
On a quiet lane in Old Town, this classic Conch home offers a setting where life feels just a little slower and a lot more enjoyable. From the moment you step inside, the home draws you outward, where indoor living blends naturally with the surrounding outdoor spaces. The heart of the home is built around entertaining. The living area, kitchen, and dining space come together in a way that encourages gathering, while the outdoor covered patio is perfect for dining or lounging creating a natural extension for everything from slow mornings to late evenings. Step outside and the pace shifts. Sitting on a large L shaped lot, the pool becomes the centerpiece, surrounded by deck space, greenery, and just enough privacy to make it feel like your own little corner of the island. The inviting primary suite is a peaceful retreat, featuring vaulted ceilings and French doors that open directly to the pool. Upstairs, two additional bedrooms and a shared bath provide comfortable separation, while the detached poolside cottage, with its own bath and outdoor shower offers flexible space for guests, a workspace, or added privacy. A convenient powder room is also located just off the kitchen. Dade County pine walls, wood floors, and tall ceilings bring warmth and authenticity, giving the home a sense of history without ever feeling heavy. It is comfortable, inviting, and easy to live in, the kind of home that makes everyday moments feel just a little more special. Quiet, central, and layered with history, 1109 Stump Lane stands as one of Old Town's most compelling hidden opportunities, a rare chance to own a truly private retreat in the heart of Key West.

1109 Stump Ln, Key West
$3,100,000
3 Beds ⋅ 2 Baths ⋅ 619319 MLS
A rare opportunity to own a stunning waterfront penthouse in the exclusive, gated Sunset Marina community--where luxury meets the effortless charm of Key West living. This exceptional 3-bedroom residence has been thoughtfully positioned to capture breathtaking panoramic views of the Gulf and marina, offering both sunrise and sunset vistas from multiple private balconies. On the Fourth of July, enjoy a spectacular fireworks display right from your own outdoor space--an experience few properties can offer. Inside, the home blends timeless elegance with modern upgrades. Rich white oak flooring runs throughout, complemented by fully finished doors and recessed lighting that create a warm, sophisticated ambiance. Expansive new impact-resistant windows invite natural light to pour in, enhancing the bright, open layout. The chef's kitchen is a true showpiece, designed by Hansen & Bringle of Key West, featuring sleek quartz countertops, premium Viking appliances, and refined custom finishes--perfect for both entertaining and everyday living. A wet bar with refrigerator adds an extra touch of convenience and style. The spacious primary suite offers a serene retreat, complete with luxurious details including onyx sinks, custom built-ins, and direct access to a private balcony. Every bedroom enjoys its own balcony, providing seamless indoor-outdoor living throughout. Additional high-end features include a whole-house water purification system with a double filtration system for drinking water, power shades on the porch, and thoughtfully curated furnishings for a move-in-ready experience. Residents of Sunset Marina enjoy resort-style amenities including a heated waterfront pool, clubhouse, elevator access, deeded parking, garage and guest parking, and private storage. Boat slips are available, offering quick access to world-class fishing and the pristine sandbars of both the Gulf and Atlantic.This residence offers the ultimate in island lifestyle.

5605 College Rd Unit # E305, Key West
$1,499,000
3 Beds ⋅ 3 Baths ⋅ 619306 MLS
Tucked away in the Historic Seaport District, this unique three-bedroom, two-and-a-half-bath condo offers privacy, charm, and flexibility in an exceptional location. Set behind a gated rear entry, the property features a private pool, deck, and lush mature tropical landscaping. The main cottage includes a spacious primary suite with en suite bath, inviting living and dining spaces, a large kitchen, and laundry. A separate guest cottage offers two additional bedrooms and a full bath. Just moments from dining, shopping, and more, this is a wonderful opportunity for an island home, guest retreat, or rental investment.

912 James St Unit 2, Key West
$2,165,000
3 Beds ⋅ 3 Baths ⋅ 619190 MLS
A hidden gem nestled in our popular Sunrise Shores New Town district, this distinguished single family home is a testament to estates providing rare space, privacy and refined living. Not into ''downsizing'' - 3513 Sunrise Drive encompasses 3 bedrooms, 3 full baths, and this 2-story CBS home spans 2,569sf on an expansive 9,487sf landscaped completely fenced-in super-private corner lot. The first floor is set to entertaining with Mexican tile floors throughout, a gourmet kitchen (with new appliances), dining room, open living room, bedroom and bath and a mother-in-law / guest bedroom/bath with private entrance. Both the large covered porch and separate outdoor kitchen / BBQ area state, ''relax and invite your friends over!'' A dramatic flowing staircase leads to the second floor primary master ensuite bedroom with private balcony over-looking the large heated salt water swimming pool, private lush indigenous tropical exotic orchid gardens and gazebo. With private gated entrance, off-street parking, plenty of outside storage areas, and many on-site updates (automatic yard lights, timed irrigation system, Ring cameras throughout, Aquilink pool and fountain control, new roof and gutters, new A/C system, new water heater, new Kohler generator) to name a few. Enjoy our local bars, restaurants, museums, art galleries and shops, beaches, and seaport activities (all within 10 minutes), then come home to a bit of peace and quiet. Comes furnished, this charming home available to purchase and close on at your earliest convenience

3513 Sunrise Dr, Key West
$1,100,000
2 Beds ⋅ 3 Baths ⋅ 619283 MLS
Charming 2BD/2.5BA Key West cottage nestled in the sought-after Meadows neighborhood. Recently refreshed inside and out, this home features newer stainless steel appliances, granite countertops in the kitchen and baths, and beautifully updated tile bathrooms, along with numerous additional upgrades. The light-filled great room opens through French doors to a private outdoor oasis complete with a pool and gazebo, perfect for relaxing or entertaining. Offering flexible living, the home features a primary bedroom option on either the first or second floor. Ideally situated just minutes from both Old Town and New Town, this property combines classic Key West charm with modern improvements.

1317 Newton St, Key West
$7,495,000
5 Beds ⋅ 7 Baths ⋅ 619282 MLS
Located in the heart of Old Town, 616 Eaton Street tells a story that spans more than a century. Built in 1911 and thoughtfully brought into the present day, with additions & renovations, this property reflects the enduring character of Key West while offering the comforts and conveniences of modern living. This 5BD, 5 full BA, and 2 half BA estate spans over 4,000sf and sits on an expansive 12,478sf lot. Set back from the street, it offers a level of privacy that is rare for such a central location. The main residence is designed for both everyday living & entertaining and has been furnished with new furniture & finishings adding a refined & move in ready touch. The fabulous kitchen, outfitted with top of the line finishes, opens through huge sliding glass windows to an outdoor bar & entertaining pavilion creating a seamless indoor & outdoor experience. Upstairs, the primary suite offers a quiet escape with its own office, laundry, and a generous covered porch. Throughout the home, reclaimed hardwood floors from the Biltmore, tall ceilings, and natural light highlight the balance between historic charm & modern upgrades. The outdoor space serves as the heart of the property, anchored by a heated & chilled saltwater pool with a tranquil water feature. Two detached guest houses provide a total of 3BD & 3BA, complemented by an additional cottage that can function as a 4th bedroom & bath or a private entertaining retreat. The versatility of this home is truly exceptional, ideal for hosting guests, extended stays, or creating secluded personal spaces. Additional features include a 1,500sf climate controlled attic for storage, off-street parking for up to 7 vehicles, a carport, and a golf cart garage. Positioned in the desirable X flood zone and just 2 blocks from Duval St. and the Historic Seaport, this property represents a rare opportunity to own a significant piece of Key West history, thoughtfully updated for modern living.

616 Eaton St, Key West
$1,100,000
2 Beds ⋅ 2 Baths ⋅ 619263 MLS
HARBOUR PLACE | TRUMAN ANNEX. This waterfront gated community boasts amazing ocean views from the pool and patio areas. Unit 102 has an open floor plan that seamlessly connects the dining and living areas, leading out to a private balcony. This residence features two bedrooms, including a spacious primary suite with a large walk-in closet and a full bathroom. The second bedroom is also generous in size and offers plenty of closet space. As a first-floor unit, it provides easy accessibility without the need for elevators or stairs. Additionally, this unit comes equipped with a washer and dryer, along with a covered parking space. Features include central air conditioning, impact windows and doors, and it comes furnished. Harbour Place provides secure entry and a heated pool amidst beautifully landscaped grounds, all just steps away from Duval Street, shopping, theaters, Fort Zachary Beach, and the Amphitheater.

115 Front St Unit APT 102, Key West
$1,239,999
3 Beds ⋅ 2 Baths ⋅ 619251 MLS
DO NOT MISS YOUR CHANCE TO OWN YOUR OWN PIECE OF KEY WEST HISTORY!!!! Located in the heart of the Historic District, just steps to world famous Duval Street, 5 minutes to Higgs Beach, and the world Famous Island House and Garrison Bight Marina being literally around the corner, this location is UNBEATABLE. Featuring almost 1700 Square Feet of indoor living space, this Gem mixes Old Town Conch Charm with contemporary living and comfortably sleeps 6 adults. On the first floor you'll find a spacious living room, dining room, the recently remodeled kitchen with a wine cooler and a bar area. Off to the side, you'll find an expansive bedroom and a beautiful bathroom. Upstairs features two bedrooms and an additional bathroom with a shower tub. Exterior features include offstreet parking, a perfectly sized heated pool and deck area for entertaining, and a low maintenance yard. Utilizing the side door you can avoid walking up any stairs at all. Hurricane shutters and a metal roof provide peace of mind. If you're looking for an amazing primary home, an investment property, or a mix of both... This one checks all the boxes!!!! SOLD FULLY FURNISHED SO JUST BRING YOUR BAGS!!! CALL DIRECTLY for your private showing today. MOTIVATED SELLERS SAY BRING ALL OFFERS!!!!

524 White St, Key West
$7,000,000
3 Beds ⋅ 3 Baths ⋅ 619242 MLS
Escape to Sunset Key, a private island sanctuary where refined elegance meets effortless tranquility. Just a four-minute ferry ride--operating 24 hours a day--from the vibrant charm in the heart of downtown Key West, this serene enclave offers the rare balance of seclusion and accessibility, keeping the energy of Old Town within effortless reach at any hour. This exquisite three-bedroom, three-bath beachfront home is thoughtfully designed to capture the essence of elevated island living. Wake to sweeping water views from the primary suite, and enjoy the same serene vistas from the main living area, where natural light and coastal beauty take center stage. Step outside to your private pool and spa, where you can unwind to the rhythm of waves lapping along the shoreline, all while enjoying gentle sea breezes and breathtaking sunsets over the Gulf of Mexico. The expansive main-level primary suite provides a tranquil retreat, while two beautifully appointed guest suites upstairs ensure comfort and privacy for all. Rich hardwood floors and natural stone finishes flow seamlessly throughout, complemented by a warm, sophisticated island aesthetic. Set within a private island enclave, Sunset Key offers access to exceptional amenities, including a gourmet waterfront restaurant, full-service spa, state-of-the-art fitness center, private beaches, tennis courts, and convenient ferry service. Perfectly positioned within minutes of Old Town Key West yet blissfully removed from the crowds, this secluded setting delivers a truly elevated lifestyle--where every detail is designed for quiet luxury and effortless escape.

5 Sunset, Key West
$1,990,000
3 Beds ⋅ 2 Baths ⋅ 619235 MLS
Tucked within the charm of Old Town Key West, this fully renovated historic Eyebrow home invites a lifestyle shaped by tropical surroundings, outdoor living, and close proximity to the island's most recognized destinations. Set on a deep 4200+ square foot lot stretching from Eaton Street to Thompson Lane, the property offers 3 bedrooms and 2 baths in a setting designed for both everyday living and relaxed entertaining. Recognized as a 2016 Preservation Award Winner, this lovely home reflects thoughtful preservation of its architectural style while incorporating modern updates including a metal roof and a comprehensive renovation. Inside, hardwood flooring, a light-filled living area, and a main-level primary bedroom create a comfortable and functional layout. The open design flows naturally to the outdoor spaces, while the updated kitchen features white cabinetry, quartz countertops, stainless steel appliances, tile backsplash, and dedicated prep space, along with additional storage and an interior laundry area. French doors extend the living space outward to a covered deck and courtyard. The outdoor setting is a defining element of the home, centered around a private heated pool, covered lounge area and outdoor bath. Gorgeous palms and lush plantings frame the backyard, creating a private garden atmosphere with brick walkways and a spacious courtyard for dining and gathering, while string lighting enhances the space for evening ambiance. The deep lot includes off-street parking with a brick-paved driveway accessed from Thompson Lane, a valuable feature in Old Town. Just moments from the Historic Seaport, Duval Street, and some of Key West's most loved local spots, this location provides convenient access to dining, shopping, and live entertainment. With its combination of location, updates, outdoor living spaces, and off-street parking, this property presents a compelling opportunity for use as a primary residence or vacation home in Old Town Key West..

1019 Eaton St, Key West
$1,399,000
619200 MLS
425 Bahama Street presents an exceptional opportunity to own a revenue-generating parking lot in iconic Key West, Florida. This income-producing property offers existing cash flow and represents a rare investment in a high-demand location where parking remains a valuable and limited commodity. Whether held as a steady income asset or positioned for future upside, this property offers investors a unique combination of immediate revenue and long-term potential in one of the most sought-after markets in the Florida Keys. Buyer to verify all details, including income, zoning, and allowable uses.

425 Bahama St, Key West
$1,350,000
2 Beds ⋅ 3 Baths ⋅ 619140 MLS
President's Walk townhome in the Truman Annex. This is a two-bedroom, 2.5-bathroom unit that also includes a deeded carport. It is a great location close to the community pool and all the downtown attractions that Key West has to offer. It features an open floor plan with kitchen, half bath, dining and living areas that open to the rear and side yard! Upstairs are two-bedroom ensuites with vaulted ceilings and each with their own private bath and porches. The windows and doors are combination of wood and impact. It has a non-transient rental license that allows monthly or longer rentals.

564 Porter Ln, Key West
$1,995,000
4 Beds ⋅ 3 Baths ⋅ 619096 MLS
NEW PRICE!! Key West WATERFRONT Home with a POOL! This expansive two-story residence has everything you need, featuring a first-floor primary suite, ample off-street parking, and a canal for boating enthusiasts, along with a fantastic pool area complete with a tiki hut for shaded relaxation. With 4 bedrooms and 3 bathrooms, this home spans 2,080 sq. ft. and is just minutes away from Old Town Key West. Nestled on a cul-de-sac, Jamaica Drive is the perfect island oasis--simply drop your paddleboard in from your backyard! The kitchen is chef-ready, offering plenty of cabinet space and a large island. The open floor plan is designed for entertaining, seamlessly flowing to the backyard area with tiki hut, canal views, and a beautiful swimming pool. The first floor includes a primary suite with a luxurious bath, walk-in closet, and pool access. There are three spacious bedrooms located on the second floor. Additional features include central AC, ductless units, a workshop, soundproof windows, impact-rated doors, and hurricane panels. Saltwater pool with chiller and heater. Perfect canal home with seawall without leaving KW!

1620 Jamaica Dr, Key West
$1,480,000
2 Beds ⋅ 4 Baths ⋅ 619087 MLS
Legal duplex in the heart of Old Town Key West offering flexibility for investors or owner-occupants alike. Each residence features a private entrance, in-unit laundry, electric meter, and thoughtful renovations that make the property truly turn-key. Classic Key West character shines throughout with vaulted ceilings, exposed beams, skylights, and beautiful wood floors creating a bright and airy feel. Updated kitchens, bathrooms, and high-end appliances add modern comfort while maintaining the home's historic charm. Perfect for living in one unit while renting the other, or as a full investment property. The home is fully fenced and includes an off-street parking space, just blocks from Duval Street

709 Olivia St, Key West
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619022 MLS
This two-bedroom, two-bathroom condominium residence at Santa Maria Suites Resort offers both personal use and strong rental income potential. One of the resort's limited single-level units, the property produces nearly $200,000 in annual gross rental income and allows for transient nightly rentals. The floor plan features a generous living and dining area, full kitchen, and two private bedroom suites. Located just steps from iconic Duval Street, the property provides convenient access to Old Town restaurants, shops, and nightlife while maintaining a quiet resort setting. Resort amenities include swimming pool, fitness center, and off-street parking. Planned improvements to the residences, pool, and fitness areas are scheduled for completion in 2027. The current owner has paid the majority of the special assessment associated with these upgrades. Owners may choose their own rental management company or participate in the on-site program. Suitable for buyers seeking an income-producing investment, second home, or a combination of both.

1401 Simonton St Unit # 11, Key West
$2,999,500
2 Beds ⋅ 2 Baths ⋅ 618955 MLS
Beautifully updated and styled with plush new interior designed furnishings, 401 Emma Street Unit H is a vacation rental townhome that has BOTH Ocean and Harbor views in the heart of Truman Annex. Enjoy gorgeous sunset vistas of the Atlantic and the Gulf while also overlooking the the tropical and lush grounds of Truman Waterfront Park and Truman Harbor. This residence features a large covered balcony right off the main living area with living room, dining room and kitchen all in easy access. The second story's primary bedroom and bath opens out to its own private balcony. This gem is in the highly desirable Old Town location Mill's Place condominiums in Truman Annex.

401 Emma St Unit APT H, Key West
$1,410,000
3 Beds ⋅ 3 Baths ⋅ 618947 MLS
Beautifully maintained 3-bedroom, 2.5 bath pool home located in the highly desirable Newtown neighborhood of Key West. This property offers the perfect balance of indoor comfort and outdoor island living. A flagstone pathway leads to your private, quaint, floating dock on Sunrise Canal, providing convenient access to launch kayaks, paddleboards, and personal watercraft. From here, you can explore the Atlantic Ocean, Gulf waters, and the stunning backcountry of Key West. The home features a bright, open floor plan filled with natural light, a wet bar for entertaining, and spacious living areas that flow seamlessly to the outdoor pool space. The primary suite offers an ensuite bath and direct access to the pool area, creating the perfect indoor-outdoor lifestyle. Enjoy private poolside gatherings surrounded by tropical landscaping, or relax in the peaceful courtyard complete with a charming fountain. Additional features include a large covered carport with space for multiple vehicles, ample outdoor storage, and a separate laundry room. A wonderful opportunity to own a water-access pool home in one of Key West's most sought-after residential neighborhoods.

1507 19th St, Key West
$4,495,000
4 Beds ⋅ 5 Baths ⋅ 618937 MLS
There is a certain rhythm to life in Key West. Mornings begin outside, friends have a way of staying longer than planned, and some of the best evenings never make it past the backyard. 1614 Washington Street was designed for exactly that kind of life. Natural light, high ceilings, and an easy connection to the outdoors give the home an immediate sense of openness. The main living spaces flow naturally toward the pool and tropical garden, creating a setting that works just as well for a quiet morning at home as it does for dinner with friends that stretches late into the evening. The heated and chilled pool features two distinct levels--a shallow splash deck and a deeper swimming area--connected by cascading water features and surrounded by mature tropical landscaping that feels remarkably private. The floor plan understands that guests are part of island life, but privacy still matters. The first-floor primary suite creates a comfortable retreat for the owners, while upstairs, three en-suite bedrooms surround their own den and lounge. Family and friends can settle in, unpack, and have a space of their own rather than simply occupying yours. Behind that relaxed lifestyle is a house designed to make living here easier. Award-winning local architect Matthew Stratton brought together solid masonry construction, impact-rated windows and doors, solar power with Tesla battery storage, an EV charger, custom cabinetry, quartz surfaces, and thoughtful systems chosen for the realities of coastal living. The technology is there when you need it and nearly invisible when you don't. Morning walks, bike rides, the beach, neighborhood restaurants, galleries, and everything that makes Key West unlike anywhere else are simply part of the day. 1614 Washington invites you to open the doors, gather the people you love, jump in the pool, stay for dinner, and make yourself at home. Because ultimately, the best luxury isn't about having more. It's having a home that lets you live well.

1614 Washington St, Key West
$1,969,000
3 Beds ⋅ 3 Baths ⋅ 618929 MLS
Welcome to your ideal island escape at 1607 Sunshine Drive in vibrant Key West, FL! This newer-construction 2014 single-family home offers the modern coastal lifestyle you want - built to the latest building codes for improved insurance options- featuring impact glass windows and doors, metal roof, concrete siding, and an elevated structure above base flood for added peace of mind. Step inside to a bright, breezy layout with a full bedroom and bath on the first floor with a convenient Murphy bed for ultimate flexibility, plus two spacious en-suite bedrooms upstairs -- each opening to private decks where you can catch the island breeze and have a morning con leche or an evening Cuba Libre. You'll love the coastal finishes throughout, including plantation shutters, granite countertops, and stainless steel appliances, plus a beverage pantry that adds a fun, functional touch. Outside is where this home truly shines: the fully fenced lot includes privacy fencing around the backyard, composite decking on all deck surfaces, and tropical landscaping complete with lighting and irrigation--creating a polished, resort-like setting for relaxing or entertaining. A heated pool and two off-street parking spots round out the experience. The home may be offered furnished for a true turn-key opportunity, 1607 Sunshine Drive is ready for you to start living the Key West lifestyle from day one.

1607 Sunshine Dr, Key West
$1,299,999
3 Beds ⋅ 2 Baths ⋅ 618878 MLS
LEGAL DUPLEX with INVESTMENT OPPORTUNITY. Located in the Old Town Key West neighborhood in the X Flood zone, this historic property presents many opportunities. Increase the square footage and/or covert to a single family home. Bring your creativity to this historic charmer. Currently set up as a Legal Duplex with 2 bedrooms/1 bath downstairs, and 1 bedroom/ 1 bath upstairs with separate electric and water meters. The attic can easily be converted to additional living space the same size as the upstairs unit. Adding approximately 700 sq ft. Park your car in your own private driveway. Add a pool to your backyard. The property is fenced in and very private. An aquifer exists on the property allowing you a water source for your irrigation and landscape. The amenities of this location offer a neighborhood grocery store, bakery, restaurants, art galleries and Bayview Park all with in walking distance. Now is your chance to bring your vision to reality in Old Town Key West. Schedule your private tour today!

1306 Virginia St, Key West
$1,346,000
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
$2,160,000
4 Beds ⋅ 4 Baths ⋅ 618235 MLS
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 X Behind 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 travertine and Ipe Brazilian hardwood floors, wood-clad ceilings, and a gourmet kitchen outfitted with stainless steel appliances and a wrap-around peninsula that naturally becomes the heart of the home. Whether hosting friends or enjoying everyday living, the flow is intuitive and inviting. French doors throughout the home create a strong connection to the outdoors. One bedroom opens directly to the pool, while another enjoys a peaceful, tucked-away deck perfect for morning coffee or quiet reflection. The primary suite is a true sanctuary, featuring vaulted ceilings, a spacious marble bath with multi-jet shower, walk-in closet, and direct access to an expansive Ipe sundeck. Outside, a large heated pool anchors a lush, private oasis surrounded by tropical landscaping and a privacy fence ideal for entertaining or unwinding in complete tranquility. A shaded loggia adds yet another layer of livable outdoor space. Off-street parking, LOCATED IN X FLOOD ZONE provides rare Old Town convenience!

1209 Packer St, Key West
$1,300,000
7 Beds ⋅ 5 Baths ⋅ 618731 MLS
Builder/Contractors Dream ! Rare 4 unit new development opportunity, 7,000 square ft lot available in Midtown Key West.

2016 Roosevelt Dr, Key West
$2,595,000
4 Beds ⋅ 3 Baths ⋅ 614088 MLS
Price Reduction. Excellent opportunity to purchase a luxurious, modern, and refined single-family home in one of the best neighborhoods in Key West. This 4bed/3bath completely renovated and modern home is being offered completely furnished with all new furniture and ready for new owners. Just over 1930 S.F. of beautiful living space and situated on a 5,896 S. F. corner lot. This CBS home has all hurricane impact rated windows & doors, flood panels for all doors, and 25 KW Generac stand by whole house generator. There is an abundance of windows & doors allowing for plenty of natural light throughout the home. True chefs kitchen features gorgeous cabinets & counter tops with all stainless steel appliances. Dual ovens, gas stove top range, and wine cooler make your kitchen complete. The kitchen opens up to your amazing living & dining room areas. From there you will find this opens up to a super nice covered outdoor patio area, in ground, salt water, and heated 27L X 9W Jacuzzi & pool with water fall. Ready to kick back and relax. Outdoor areas have travertine tiles throughout and have lush native tropical landscaping with lighting & irrigation systems. Property has a 1 car covered carport and CBS privacy fencing around entire property. This home is located within walking distance to Higgs Beach, White St. Pier, and a short distance to Key West Best restaurants, beaches, museums, and art galleries. This is truly a home where modern luxury meets Key West paradise. Listing agents are related to the sellers.

1501 Florida St, Key West
$2,695,000
3 Beds ⋅ 3 Baths ⋅ 618608 MLS
A fantastic renovation of a classic Old Town Key West property, blending timeless charm with modern upgrades. First Impressions are made with a wonderful front porch greeting you as you step from your two off street parking spots--or arrive by bicycle & use the separate entrance with dedicated bike storage. Outdoor Living -A complete irrigation system with landscape lighting transforms the grounds into a tropical paradise, with quite the productive mango tree. Enter the privately fenced & gated yard and take a dip in the heated pool, kept sparkling clean & boasting new pool equipment. Rinse off in the outdoor shower, then unwind at the lighted grilling station or one of several spots to relax & dine under the stars. The Kitchen---It is fun, functional & done with the highest quality materials from Hanson & Bringle. A 15 foot impact glass wall opens to the beautifully landscaped yard & a pantry area with a bar sink adds extra prep space alongside the indoor dining area. Storage was thoughtfully designed for maximum efficiency, and an induction cooktop completes the space for those who love to cook. Bedrooms & Living Spaces----The first floor primary bedroom is classic Key West, featuring a Dade County Pine wall & a custom bedroom door. The Hanson & Bringle built-in dresser offers generous drawer space, & there's a walk-in closet. The primary bathroom includes a special shower built for two, with dual shower heads. The living room & hallway have the the original Dade County Pine walls. Upstairs there are two bedrooms, a bathroom & two additional storage closets. A Sonos sound system runs throughout the home. Move-In Ready-----This home is truly move-in ready: a new water heater was installed in late 2025 & a brand new HVAC system went in this past spring 2026. Both interior & exterior were both freshly painted. A storage shed & outdoor fridge round out the practical upgrades. Location-- This home is just a 1/2 block from some of the best shops & restaurants

525 Louisa St, 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
$1,689,000
4 Beds ⋅ 3 Baths ⋅ 618064 MLS
Set on the highly desirable upper end of Eagle Avenue, this four bedroom, three bath home blends timeless charm with a breezy indoor outdoor lifestyle. Arched doorways, plantation shutters, and warm wood floors set the tone, while natural light fills the expansive living spaces. The main living area is centered around a working gas fireplace, creating a welcoming focal point for both everyday living and entertaining. On the main level, you will find three bedrooms, two bathrooms, a formal dining room, and a separate cooks kitchen featuring custom cabinetry, quartz countertops, premium appliances, and a center island. Glass fold back doors open to a covered outdoor living area, pool, and spa, extending the living space outdoors and creating a relaxed courtyard style setting ideal for entertaining or unwinding. Upstairs, the fourth bedroom with ensuite bath offers a private retreat, along with an additional living space and a large finished attic providing exceptional storage. This home provides the perfect opportunity to personalize every space and make it your own. Additional highlights include gated, covered off street parking, tiled walkways, and a fully fenced property for added privacy. Some photos have been virtually enhanced to illustrate potential.

3700 Eagle Ave, Key West
$1,850,000
4 Beds ⋅ 3 Baths ⋅ 616978 MLS
Pool. Space. Privacy. -- Rare Double Lot Living in Key West 1719 Laird Street offers the space and upgrades buyers search for but rarely find in Key West. Set on an oversized double lot, this renovated 4-bedroom, 3-full- bathroom CBS home features generous living spaces, wide hallways, and abundant storage, creating a comfortable layout that feels open, functional, and easy to live in. The bright open-concept living area welcomes natural light and connects seamlessly to the outdoor spaces. Improvements include impact windows and doors, new roof, new A/C system, updated appliances, and a whole-house generator, providing efficiency, security, and storm-ready peace of mind. Step outside to a private tropical backyard oasis featuring a large heated swimming pool, lush landscaping, and a fully fenced yard--ideal for entertaining, relaxing, or enjoying the Key West lifestyle year-round. Located in a desirable residential neighborhood just minutes from Old Town Key West, beaches, boating, dining, and shopping, this move-in-ready property delivers the rare combination of space, privacy, and modern upgrades in one of the island's most sought-after locations. A rare opportunity to own a renovated Key West pool home on an oversized double lot in a great neighborhood.

1719 Laird St, Key West
$1,100,000
4 Beds ⋅ 2 Baths ⋅ 617746 MLS
Nestled within lush tropical landscaping, this unique Key West home offers serene privacy and island charm just minutes from everything. A winding brick pathway leads you through mature palms and gardens to an inviting covered entryway. Inside, the home features spacious open living areas with exposed beam ceilings, a functional kitchen, and two classic tiled bathrooms, including a glass-block walk-in shower, large windows, and natural light throughout. This two-story property also includes a generous outdoor living deck, perfect for relaxing or entertaining, and a tranquil garden setting that feels like your own private retreat. With its solid structure, character-filled details, and endless potential to personalize, this home is an exceptional opportunity for buyers seeking charm, space, and the true island-living experience. A unique opportunity to own a character-filled home with endless potential in a desirable location.

2914 Fogarty Ave, Key West
$19,550,000
611315 MLS
Located on the northside of Old Town only two blocks from the historic Key West Port, NYAH is walking distance from the main strip of bars and restaurants on Duval and proximate to historical landmarks such as the Southernmost Point, Ernest Hemingway Home, Key West Butterfly Conservatory, and Mallory Square. The Property is designed for hosting group travelers offering both private and shared guestrooms. Private Rooms can accommodate groups of up to six people and each guest is provided their own bed, locker, and set of towels. Guestroom amenities include en-suite bathrooms, private lockers, and personal charging docks. Home to three outdoor pools, NYAH is in possession of a bar license and serves drinks from the front desk. NYAH also features an office space which can be converted into a 3-bedroom transient unit. As the Property holds 36 transient licenses, no additional ROGO is needed.

823 Fleming St, Key West
$1,899,000
7 Beds ⋅ 6 Baths ⋅ 615914 MLS
Rare opportunity to acquire SEVEN units in the X-Flood Zone in Old Town Key West. That's correct, seven market rate units! Renovations in progress! Priced at less than $272K per unit! Recent changes to IRS tax code (such as accelerated depreciation) can benefit RE Investors - ask your tax expert. Prime Old Town location, just 1/2 block from cemetery and 1/2 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 attractions 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.

909 Grinnell St, Key West
$1,949,000
2 Beds ⋅ 3 Baths ⋅ 616792 MLS
Experience ultimate elegance at Key West's Beachside Resort & Residences! This first-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income. The Signature King Room (283 sq. ft.) is an intimate, elegantly furnished retreat ideal for up to two guests. The Resort View Suite (1,074 sq. ft.) features an open floor plan with a designer kitchen equipped with Sub-Zero, KitchenAid, GE, and Bosch appliances, dual stainless-steel sinks, and custom cabinetry. The primary suite offers a spa-inspired bath with a sunken jetted tub, tiled shower, and dual vanities. Throughout the unit, you'll find 16-inch marble tile flooring, crown molding, and high-end finishes that elevate every detail. Fully furnished and beautifully decorated, this residence is designed for year-round living or part-time ownership—with the convenience of optional on-site rental management when you're away. All doors and windows are engineered to exceed building codes, rated for up to 175 mph winds, ensuring both safety and peace of mind. Resort-style amenities include a private beach, heated waterfront pool and spa, poolside bar & grill, gourmet restaurant, fitness center, valet parking, concierge services, on-site management, and the island's largest conference center. Positioned on open Gulf waters, this condo presents an extraordinary opportunity to enjoy the best of Key West luxury living—a perfect combination of personal enjoyment and investment performance.

3841 N Roosevelt Blvd Unit 315, Key West
$1,055,000
3 Beds ⋅ 3 Baths ⋅ 618748 MLS
Welcome to 1421 12th St, a stunning oasis nestled in the heart of Key West. This charming property perfectly combines island living with modern convenience, offering an exceptional opportunity for both homeowners and investors alike. As you step inside, you are greeted by an open-concept layout that maximizes space and natural light. The living area boasts high ceilings and beautiful finishes, creating a warm and inviting atmosphere. The kitchen is a chef's dream, featuring stainless steel appliances, granite countertops, and ample storage space, making it perfect for entertaining friends and family. This home includes multiple spacious bedrooms, each designed for comfort and relaxation. The master suite is a true retreat, complete with an en-suite bathroom that offers a spa-like experience. Step outside to your private backyard oasis, where you can unwind in the tropical surroundings or host barbecues under the stars. Located just minutes from Key West's vibrant downtown, you'll enjoy easy access to the area's best dining, shopping, and entertainment options. The beautiful beaches and iconic sunsets are just a short bike ride away, allowing you to fully embrace the island lifestyle. One bedroom is set to the side of the house and is designed for your guest's privacy with it's own outside shower, exterior door, locking interior door, full bath and wetbar. There are two off street parking spots under the carport and two on the side of the house. Don't miss your chance to own this exceptional property in one of Florida's most sought-after locations. Schedule your private showing today and discover the endless possibilities that await at 1421 12th St! Professional Vacation Rental Management is available for this property.

1421 12th St, Key West
$1,298,000
3 Beds ⋅ 2 Baths ⋅ 617759 MLS
Welcome to 2828 Harris Avenue, a private retreat nestled in the heart of Key West's highly desirable New Town neighborhood. Beautifully updated and thoughtfully designed, this single-family home blends modern comfort with timeless island charm, surrounded by lush, mature landscaping and a backyard that feels like your own personal resort. Designed for indoor-outdoor living, the property features a heated and chilled 10' x 20' saltwater concrete pool for year-round enjoyment, along with a fully fenced yard offering exceptional privacy. A screened lanai provides the perfect setting for morning coffee, outdoor dining, or relaxed entertaining. Ample off-street parking, including a covered carport, adds everyday convenience. Inside, the home opens to an expansive great room where the oversized kitchen flows seamlessly into the Florida room—ideal for gatherings, entertaining, or simply enjoying the connection to the outdoors. The renovated kitchen showcases high-end finishes, sleek countertops, and stainless steel appliances, while large sliders frame lush pool and garden views, blurring the lines between indoor and outdoor living. The flexible floor plan also offers potential to add a third bathroom, allowing for future customization. Recent upgrades include a new electrical panel and a 2024 AC heat-pump system, providing comfort and peace of mind year-round. This home truly checks all the boxes—privacy, thoughtful upgrades, resort-style outdoor living, and a prime location—offering relaxed island living at its finest in one of Key West's most sought-after neighborhoods.

2828 Harris Ave, Key West
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 618862 MLS
Don't miss this rare opportunity to own a legal duplex on a spacious 10,000 SqFt corner lot! The main residence, solid CBS construction, offers 2 bedrooms, 2 bathrooms, and a generous 2,004 SqFt of living space. The open-concept layout features a large living room, a well-appointed kitchen with an adjoining dining area, and plenty of natural light. There's also a garage, laundry room, and potential to easily add a third bedroom. The separate 2-bedroom, 1-bath cottage spans 660 SqFt—perfect for rental income, extended family, or a private guest house. Outside, the expansive yard offers endless possibilities. With plenty of space for a custom patio, outdoor kitchen, or fire pit, it's the ideal setup for entertaining, weekend gatherings, or simply enjoying the outdoors. Plenty of parking for multiple vehicles, a boat, or a trailer—perfect for those who need both space and versatility. Whether you're an investor or looking for a multi-generational living solution, this property is packed with potential and ready to make your vision a reality!

1409 4th St, Key West
$2,790,000
3 Beds ⋅ 3 Baths ⋅ 616089 MLS
Unique and extraordinary triple (3) lot property located in Old Town, Key West! Currently featuring a two-story home with 2 bedrooms and 2 bathrooms, and an in-ground pool. In addition, there is a detached studio/cottage, with each separately fenced from one another. On the third lot is a garage. Come and explore these three (3) contiguous, separate lots that all have the City of Key West's, Building Permit Allocation System (BPAS). Total lot SQ FT is 11,968. If you're seeking an opportunity to either build/renovate your future home, or a lucrative development opportunity, or simply to own one of Key West's most unique properties, look no further! It's time to make the move! Come to 1405/1409 United and see that it has the best of all the locations that Key West has to offer. Walking to all the amenities that Key West has, but far enough away from all the noise of the downtown. Plenty of room to make your own mark here. Location, Location, Location is this property. Call today for your private showing!

1405-1409 United St, Key West
$1,700,000
2 Beds ⋅ 2 Baths ⋅ 616994 MLS
Licensed for nightly Rentals! On average 120k/yr. Introducing an exquisite offering at one of Key West's sought-after waterfront resorts, 1800 Atlantic Blvd. A completely remodeled, stylish 2-bedroom, 2-bathroom condo encompassing approximately 1,311 sq ft of luxurious living space. Transient license and established management make this a rare turnkey investment opportunity offering both a seamless path to rental income and a refined retreat for personal enjoyment. Remodel completed in 2022, this turnkey residence underwent a full interior renovation. The open-plan kitchen showcases brand-new appliances, sleek cabinetry, and generous counter space, perfect for entertaining or everyday island living. The spacious living area flows seamlessly onto a large private balcony, where ocean breezes and tropical surroundings create an effortless connection to the outdoors. Both bedrooms provide balcony access and serene comfort, complemented by two beautifully finished bathrooms and an in-unit washer and dryer. Perfectly positioned on the coveted sunrise side of 1800 Atlantic, this residence delivers the quintessential resort lifestyle featuring an Olympic-size heated pool, jacuzzi spa, three lighted tennis courts (hard and clay), lush tropical gardens, private beach access, BBQ/picnic areas, and covered garage parking. Located just minutes from Old Town Key West and the airport, the property balances tranquil oceanfront living with exceptional convenience. Whether you're seeking an income-producing asset or a luxurious island getaway, Unit 327C at 1800 Atlantic Blvd stands as an exceptional choice for those desiring effortless ownership and elevated coastal living in Key West.

1800 Atlantic Blvd Unit 327C, Key West
$6,850,000
3 Beds ⋅ 3 Baths ⋅ 617136 MLS
103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. This home is perfect for entertaining on a large scale or enjoying a quiet evening. A dramatic staircase leads to a second floor walkway which is open to the main level. The floor plan provides privacy for each bedroom with the primary suite at one end of the hallway and a guest bedroom suite at the other end. Another guest bedroom and bath are on the first floor creating an option for a first floor primary bedroom. Custom features throughout are evidence of the artistic ingenuity used in the design of this impressive home. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Tall windows and french doors flood the home with sunlight. This home is perfect for indoor/outdoor entertaining. A wet bar features custom built ins plus an icemaker and refrigerator. Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property comprises two lots with a large swimming pool and spa plus an outdoor shower between the covered and open air loggia and parking. There's plenty of space for entertaining outdoors under the palm trees. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure.

103 Front St, Key West
$1,899,000
6 Beds ⋅ 3 Baths ⋅ 611164 MLS
Discover the essence of island living in this expansive 3,197sf, 6-bedroom, 3-bathroom home, perfectly positioned on a generous 9,500sf corner lot in the heart of Key West. This spacious 2 story CBS home features a gourmet kitchen, tile floors, 2 laundry areas, sundeck & a new roof. The sprawling yard, enclosed by a privacy wall, offers plenty of room for boat and trailer storage, RV parking, and a safe play area for kids and pets. An in-ground concrete pool with water feature adds to the outdoor appeal, while a storage shed provides extra convenience. Offering a rare combination of convenience and space, this residence is ideally located minutes from schools & grocery stores, while also being near the new Happy Landings Marina and the Key West Yacht Club, making boating a breeze! With a flexible layout and ample space, this property is brimming with possibilities, ready to be tailored to your vision of the perfect island retreat.

1229 5th St, Key West
$1,295,000
2 Beds ⋅ 3 Baths ⋅ 617823 MLS
Discover relaxed coastal living in this three-level townhome located within the gated Seaside Residence community—an incredible opportunity to own in a sought-after resort-style setting. Designed for ease and functionality, the home features a private elevator serving all floors, a spacious garage, and an inviting layout well suited for full-time living or a seasonal retreat. The ground level includes the garage with a conveniently located laundry area and additional space ideal for storage or flexible use. From this level, step outside to a private outdoor area—perfect for enjoying ocean breezes and quiet moments. The second floor is dedicated to the bedrooms, featuring a primary suite with an ensuite bath and private balcony. A second bedroom also includes its own bath and balcony, providing comfortable accommodations for guests or family. The top floor opens to the main living and dining space, filled with natural light and extending to a balcony with Atlantic Ocean views. The kitchen offers ample cabinetry and counter space and flows naturally into the dining area, creating a welcoming setting for gatherings and everyday living. Residents enjoy the privacy of a gated community, access to a community pool and gym, and a convenient location close to the airport—offering the ideal balance of coastal tranquility and accessibility. Enjoy front-row views of the island's most beautiful sunrises and moonrises—nature's show, right from your new home. Don't miss this incredible opportunity - ocean view residences like this rarely come on the market. This home may also be offered fully furnished, including artwork throughout, with many original pieces created by our beloved local artists. A Very Special Thank You to Key West Art Center and Gallery for featuring their art.

77 Seaside North Ct, Key West
$2,240,000
3 Beds ⋅ 3 Baths ⋅ 618823 MLS
Extraordinary home in the historic district! Enjoy Key West living in the prized Old Town neighborhood with the perfect combination of all the top sought after attributes requested by buyers: walkable location, swimming pool, & private parking without compromise. Offered entirely furnished, the 3 bedroom and 3 bath home is absolutely move-in ready, prepared for your immediate occupancy. With over 1500 sq. ft. of interior living on 2 floors, a bedroom/office and a full bath are on the ground level, with a full master suite and an additional bedroom and bath on the second. Generous off street parking is superb for the historic district location, with room for all full size vehicles and perhaps even 2 cars. From the charming covered front porch, through the open main living area, and on to the pool and deck, the delightful home offers a seamless, integrated living space that is welcoming and ideal to gather and entertain. Expertly crafted renovations with modern design features are highlighted by historic details to remind you of living in Old Town. If lucrative vacation rental income potential is of interest, the home has been rented for over $19,000 mo. A complete package containing a survey, elevation certificate, insurance declaration pages, and other helpful documents available on request.

413 Frances St, Key West
$3,750,000
8 Beds ⋅ 8 Baths ⋅ 618438 MLS
Rare Multi-Family Investment Opportunity in Old Town Key West. This unique property is comprised of eight updated one-bedroom, one-bathroom units. 2 buildings situated on a 5,575 SqFt lot. It offers an exceptional opportunity for employers seeking staff housing, investors interested in a 1031 Exchange, or those considering a condo conversion. Please note that advanced notice is required to arrange showings, and not all units may be available for viewing as they are currently rented.

818 Elizabeth St, Key West
$1,799,000
3 Beds ⋅ 3 Baths ⋅ 610882 MLS
Excellent opportunity whether looking for a private residence or an investment. This home will not disappoint. Artfully renovated very spacious three story . Plenty of outside area including private courtyard with a heated pool. Walk out the front door and just steps away from Duval st. and everything Key West has to offer. This is maintenance free living while it gives the feeling of a private residence. Assigned off street parking right in front of the unit. This property is being offered turnkey. Vacation Rental history available .This home has all hurricane impact windows and doors. making the unit noiseless. This condo is a freestanding building just like a single family home without the maintenance.

1011 Simonton St Unit R1, Key West
$3,100,000
3 Beds ⋅ 3 Baths ⋅ 617354 MLS
Welcome to 524 Southard Street, an extraordinary luxury offering in the heart of Old Town Key West that blends upscale finishes, commercial versatility, & superior sustainable construction just steps from Duval Street. This fully renovated mixed-use property features 2,262 sq. ft. of refined interior space designed with modern industrial style & historic Key West character. Inside, soaring 14' ceilings, expansive porcelain tile & luxury vinyl flooring, & thoughtfully curated lighting create an atmosphere of understated sophistication. The custom chef's kitchen is beautifully appointed with quartz countertops, premium appliances, a generous walk-in pantry, & sleek modern cabinetry. The flexible layout includes 3 bedrooms (1 used as a media room), 3 spa-inspired bathrooms, & a well-equipped laundry room. A separate office with its own off-street entry provides a true live/work advantage, delivering privacy & ease of access without entering the main residence. Outside, a private tropical oasis awaits with a heated and chilled pool, tranquil water feature, & lush landscaping, creating the perfect sanctuary for relaxation or entertaining. Zoned HCT (Historic Commercial Tourist), the property provides exceptional opportunities for luxury live/work use, rental investment, or commercial operation. It qualifies as a transient license receivership site & boasts a successful commercial history, adding value for those seeking income-producing potential in a prime location. Built with durability & efficiency in mind, the home includes impact-rated windows, doors, & skylights, a full fire sprinkler system, dual-zone cooling/heating, off-street parking for two, & a 25kW generator. Located in the desirable X-Flood zone and just moments from Key West's finest dining, galleries, and attractions, this property delivers an unmatched combination of luxury, quality, & opportunity in one of the island's most desirable neighborhoods.

524 Southard St, Key West
$1,475,000
3 Beds ⋅ 3 Baths ⋅ 618863 MLS
Timeless Old Town Charm! Discover the timeless appeal of this beautifully remodeled historic home located in the heart of Old Town, Key West. Offered fully furnished, this stunning 3-bedroom, 2.5-bath residence showcases lovingly restored Dade County Pine and blends classic craftsmanship with today's most desirable upgrades. 1211 Knowles Lane features a versatile 300 sq. ft. loft currently utilized as a third bedroom, office, and additional storage, perfect for flexible island living. Inviting front and side porches set the tone for relaxed Key West living, offering peaceful spaces to unwind and enjoy the tranquil neighborhood. Inside, you're welcomed by bright, spacious living areas highlighted by soaring ceilings and gorgeous flooring throughout the living and dining rooms. The thoughtfully updated kitchen boasts stainless steel appliances, custom cabinetry, and a generous pantry designed for both everyday living and entertaining.The bedrooms are comfortably sized, offering charm and privacy. Bathrooms have been tastefully renovated with contemporary fixtures while preserving the home's historic character. Step outside onto beautiful teak decking into your own private tropical oasis. The backyard retreat features an outdoor shower, hot tub, rooftop deck, and brick-paved driveways creating the ultimate indoor-outdoor island lifestyle. Located in a prime Old Town setting, you're just a leisurely walk or bike ride to Key West's beautiful beaches, renowned restaurants, and vibrant nightlife. *Bonus features: off street parking and located in the x-flood zone.

1211 Knowles Ln, Key West
$1,949,000
2 Beds ⋅ 3 Baths ⋅ 616791 MLS
Experience ultimate elegance at Key West's Beachside Resort & Residences! This third-floor Condominium offers the perfect blend of luxury, flexibility, and investment potential. Featuring two transient licenses and a lockout configuration, this property includes both a Signature King Room and a Resort View Suite, which can be used together or separately for optimal rental income. The Signature King Room (283 sq. ft.) is an intimate, elegantly furnished retreat ideal for up to two guests. The Resort View Suite (1,074 sq. ft.) features an open floor plan with a designer kitchen equipped with Sub-Zero, KitchenAid, GE, and Bosch appliances, dual stainless-steel sinks, and custom cabinetry. The primary suite offers a spa-inspired bath with a sunken jetted tub, tiled shower, and dual vanities. Positioned on open Gulf waters, the Suites private rooftop sundeck provides a front-row seat to Key West's spectacular sunsets. Throughout both units, you'll find 16-inch marble tile flooring, crown molding, and high-end finishes that elevate every detail. Fully furnished and beautifully decorated, this residence is designed for year-round living or part-time ownership—with the convenience of optional on-site rental management when you're away. All doors and windows are engineered to exceed building codes, rated for up to 175 mph winds, ensuring both safety and peace of mind. Resort-style amenities include a private beach, heated waterfront pool and spa, poolside bar & grill, gourmet restaurant, fitness center, valet parking, concierge services, on-site management, and the island's largest conference center. This property presents an extraordinary opportunity to enjoy the best of Key West luxury living—a perfect combination of personal enjoyment and investment performance.

3841 N Roosevelt Blvd Unit 332, Key West
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