Refine Search
Map
Sort by
$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
$799,000
2 Beds ⋅ 1 Baths ⋅ 618592 MLS
Nestled in an X flood zone in Old Town , this lovely conch cottage has been well cared for, meticulously maintained and lightly used as a seasonal getaway. The two-bedroom, one-bath residence is fully furnished and move-in ready, offering a perfect blend of charm, comfort, and thoughtful design. Behind the private gate, the home immediately feels welcoming and serene, creating a true island escape. Interior features include bamboo flooring throughout, soaring cathedral ceilings, recessed lighting in every room, and efficient ductless air conditioning. The kitchen and bath are finished with custom wood cabinetry and striking black granite countertops, reflecting quality craftsmanship and timeless style. French doors open from the living area and both bedrooms to outdoor living spaces, seamlessly connecting indoor and outdoor living. Both the front porch and rear patio provide peaceful settings for morning coffee, evening gatherings, or simply enjoying the tropical surroundings. While quietly situated, the property is just a short distance from the vibrant heart of Key West, offering easy access to restaurants, nightlife, shopping, and cultural attractions. This turnkey pied-à-terre delivers the best of island living—privacy, convenience, and undeniable charm—all in one a special place to call home!

1218 Packer St Unit REAR, Key West
$415,000
1 Beds ⋅ 1 Baths ⋅ 614786 MLS
Boutique commercial, ground floor office condo for sale in Old Town at Seafoam Condominiums. Only one of two Commercial units in the building. This 665 sf. office is turnkey and perfect for Professionals looking for a small office to own vs. paying rent every month. Great location and close to everything in Old town either by walking or biking. Exterior has several large pane windows for natural light inside. To enter off the sidewalk there are a set of gorgeous, hand made mahogany french doors. Also, there is an interior side door for private access. Interior has 12' ceilings and the layout includes front seating area with a receptionist window, administrators office and private office in rear. Half bath is ADA compliant. This unit has been totally renovated and ready to move in. Renovations include new Brazilian cherry wood floors & keystone flooring in the bathroom. upgraded electric and lighting, freshly painted, Central AC and wireless Security system. Seafoam building has coded entrance, atrium hallways and large in-ground concrete pool exclusively for Condo owners and guests. HOA fee of $1,286/mos. includes insurances and reserves. Includes Liability, Wind and Flood insurance. Building has never flooded and in X flood zone. Building is up to date with SIRS and milestone inspections. Additional $587/mos. special assessment for windstorm insurance. Same owner since 2008. Owner will consider lease with Option to Purchase. Asking rent is $4,000/mos.

812 Fleming St Unit 2, 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
$749,000
1 Baths ⋅ 618665 MLS
Welcome to Flagler Center III, a brand-new mixed‑use development currently under construction, with groundbreaking already completed and anticipated completion by the end of 2026. This 1,491 ± sq. ft. commercial space, comprised of two combined units, presents an outstanding opportunity for businesses looking to establish or expand in one of Key West's most sought‑after commercial corridors. The project will feature 14 residential and 14 commercial units (with select units combined), creating built‑in foot traffic and long‑term value. The subject unit includes two separate parcel IDs, allowing it to be split into two individual units, offering exceptional flexibility and strong investment potential. The property offers ample parking and ADA‑compliant access. Delivered as a white box, the space allows buyers to design and build out the interior to suit their specific business needs. Ideal for professional services, medical offices, or retail use, this property benefits from strong rental demand driven by Key West's limited commercial inventory. The prime location provides excellent visibility, consistent foot traffic, and outstanding exposure, making it an excellent opportunity for both owner‑users and investors.

3201 Flagler Ave Unit STE 507, Key West
$945,000
2 Beds ⋅ 2 Baths ⋅ 617688 MLS
Spectacular sunrise ocean views from this beautifully renovated Key West By The Sea condo on Smathers Beach. This 2-bedroom, 1.5-bath residence feels like new construction, featuring a fully remodeled kitchen with new appliances, updated bathrooms, new flooring throughout, dimmable lighting, new fans, and more. The Mitsubishi mini-split AC and heating system, upgraded electrical panel, water heater, and hurricane-impact soundproof doors and windows are all in pristine condition. Enjoy unobstructed views from the balcony overlooking Smathers Beach and the Atlantic Ocean, with paddleboard, kayak, sailboat, parasail, chair, and umbrella rentals just steps away. Key West By The Sea is a gated community offering two swimming pools, two tennis courts, a clubhouse, four laundry rooms, a car-wash station, bike racks, a pet-walking path, and lush fruit trees. This pet-friendly community includes building insurance, cable TV, Wi-Fi, and building/grounds maintenance in the condo fee.

2601 S Roosevelt Blvd Unit 406A, Key West
$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
$849,000
1 Beds ⋅ 1 Baths ⋅ 618771 MLS
Charming Home in the Meadows, Old Town, Key West. This beautiful completely renovated one bedroom cottage on Pearl Street is move in ready, and is being sold furnished. Stepping into the home through the custom built Dutch-door, the interior is bright, the walls are shadow-gap wood, there is new flooring, and recessed LED lighting throughout. The Bedroom has a murphy bed, and built in bedroom drawers, with additional storage. The Kitchen has custom cabinets, granite countertops, and is steps away from the back deck with a Tiki and wet bar - and outside seating area. Mitsubishi mini split AC, Custom shades, All new impact windows and doors, and the front Dutch Door has hurricane panels. During the renovation, the whole house was insulated between the studs, 3/4 inch pressure treated plywood added, then 1' fire rock, and then lap siding- PT-kiln dried-dipped on both sides with primer. This property is completely fenced, has a sprinkler system, Outdoor shower, and the best part- is a wonderful front porch to relax and watch the world go by!

817 Pearl St, Key West
$343,500
1 Beds ⋅ 1 Baths ⋅ 616493 MLS
A new price makes this 1 bedroom 1 bath condo the least expensive property for sale in Key West. Excellent as an investment, primary residence, second home, or rental property. This condo is conveniently located in a shopping area with easy access to Duval and US 1. It is one of the few gated communities in Key West with secure entry. You have ample parking, storage, pool, tennis court, laundry, on site management, etc. The unit has newer flooring, newer AC unit, updated electrical panel, updated kitchen, newer appliances, even impact rated hurricane windows & doors. Don't miss this opportunity.

3312 Northside Dr Unit 405, Key West
$799,000
1 Beds ⋅ 2 Baths ⋅ 618838 MLS
Welcome to 3841 North Roosevelt Blvd, Unit 121, the epitome of BEACHFRONT living at the Key West Beachside Resort and Residences. This stunning Gulf View, Waterfront corner suite invites you to live like you are on vacation every day. This is a rare to come on the market opportunity, as there are only three one-bedroom units on the entire property, and this beachfront location remains the most desired. Inside, designer-grade finishes and furnishings create an atmosphere of refined elegance. Travertine flooring flows throughout the spacious living areas, complemented by an open gourmet kitchen featuring granite countertops, stainless steel appliances, and custom cabinetry. The well-appointed bedroom and two bathrooms provide ample space and privacy, while a sleeper sofa offers additional sleeping accommodations for guests. An oversized balcony provides a private retreat to enjoy the tropical breeze and breathtaking Gulf sunsets. Beyond your door, the resort's world-class amenities await, including a restaurant, bar, pool, spa, and fitness center. The on-site parking garage includes one deeded parking space, and there is a property shuttle for added convenience. This superb property offers incredible flexibility: use it as your private getaway, generate income through the onsite professionally managed rental program with no maximum stay restriction for owners, or both. The property boasts a proven track record of strong rental performance throughout 2025, demonstrating its appeal as a high-performing investment. Don't miss this prime opportunity to own a piece of paradise with lock and leave potential that is perfect for part-time residency and robust passive income. Reach out to learn more about how to make this your 2026 lifestyle.

3841 N Roosevelt Blvd Unit 121, Key West
$949,000
3 Beds ⋅ 3 Baths ⋅ 618708 MLS
Unique opportunity to renovate this historic Old Town eyebrow home on a quiet, one-way, block of Elizabeth Street. Situated on a 3038 Sq.ft. lot there is ample space for off-street parking, a pool and 5 bedrooms with a renovation. Please note that advanced notice is required to arrange showings.

818 Elizabeth St Unit Front, 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
$995,000
2 Beds ⋅ 2 Baths ⋅ 616479 MLS
This is the one! Perfectly laid out two (2) bedroom and two (2) bathroom condo, with a den/office that could be an extra bedroom, in The Heart of Old Town Key West, with off-street parking. This amazing location comes with a a covered lanai, that will greet you each and every time you come home. Several sets of French Doors will lead you from your outdoor Oasis, that is a perfect Key West garden, into your open floor plan living space. Both bedrooms are on the ground floor, but the second level has a den/loft, that could be used as a guest bedroom as well. There is also tons of storage in this home. Invite your friends and family over for a great meal prepared in your new beautiful kitchen, with plenty of room for a large dinning room table. Move to your living room for a quiet night or a fun night enjoying the view to your gardens. This is the one, located in the X-Flood zone, walking distance to all that Key West has to offer, and easy access to and from New Town. Call today for your private showing.

1209 Truman Ave Unit 5, Key West
$629,900
618774 MLS
SELLER FINANCING AVAILABLE! Seller willing to negotiate terms for owner financing while you develop this parcel. Options are open as Seller wants to move this property. Development opportunity now even more affordable! This property includes the rights to build duplex or attached townhomes in prime midtown location. Live in one unit and collect rental income from the other. Great proximity to beaches, schools and shopping.

1610-1612 Dennis 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