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1421-1425 2nd St, Key West
$799,000
4 Beds ⋅ 2 Baths ⋅ 620461 MLS
Duplex has 1,342 square feet of living space on a 2,841 square foot lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. Now offered separate from the vacant lot. Can also be purchased with lot at discounted price for both.

1421-1425 2nd St, Key West
1800 Atlantic Blvd Unit 218B, Key West
$950,000
2 Beds ⋅ 2 Baths ⋅ 620451 MLS
Coastal Living at 1800 Atlantic - where everyday life is framed by ocean breezes and turquoise water. This highly sought-after oceanfront condominium community offers the rare privilege of walking distance to Smather's Beach on the Atlantic, minutes from the airport, and the effortless ease that makes Key West living so desirable. Stroll along the shoreline in the morning, watch boats drift along the horizon, and spend your afternoons relaxing beside the resort-style Olympic-size heated pool and spa, all set within lush tropical landscaping. Residents enjoy tennis and pickleball courts, an equipped fitness center, assigned covered parking, and professionally maintained grounds--delivering true comfort, simplicity, and peace of mind in a coastal setting. Recent upgrades include impact-rated doors and windows, enhancing storm protection, energy efficiency, and long-term ownership confidence while maintaining a clean, modern coastal aesthetic. Pet owners will appreciate the flexibility of 2 pets allowed (up to 50 lbs total). Monthly association fees include building insurance, exterior maintenance, professional management, water, high-speed internet - offering a truly turnkey lifestyle. Ideally located just minutes from Old Town Key West, you're close to world-class dining, galleries, marinas, and cultural events, yet tucked away in a quiet, oceanfront enclave that feels removed from it all. Whether by bike or a short drive, everything the island offers is within easy reach. Come experience why so many call this their Key West home away from home 🌴.

1800 Atlantic Blvd Unit 218B, Key West
2313 Fogarty Ave, Key West
$1,385,000
3 Beds ⋅ 2 Baths ⋅ 620448 MLS
There is almost nothing like this in Key West: a 2007-built home, raised from the ground up to modern standards. Rare, move-in ready, and free of the surprises that come with much older homes in town. Elevated above the floodplain, with impact windows and doors rated for 175 mph winds and a 16kW standby generator, this is a home built for real peace of mind, whether you are here year-round or away for the summer. Inside, vaulted ceilings soar over travertine floors, granite counters, and stainless steel appliances, including a gas range, set off by warm custom cabinetry. The primary bedroom has a roomy walk-in closet and a spa-style stone shower. Then there is the outside, private, and tropical. Picture morning coffee by the saltwater pool and easy evenings under the covered gazebo, eight around the table with plenty of room for the grilling enthusiast. A wide composite deck and an outdoor shower to rinse off after a swim round out the space. Three bedrooms, two baths, and storage you will actually use: a floored, air-conditioned attic plus generous space under the house. A covered double driveway adds to the everyday convenience. This is the Key West home you have been waiting for.

2313 Fogarty Ave, Key West
2005 Fogarty Ave, Key West
$749,000
3 Beds ⋅ 2 Baths ⋅ 620436 MLS
Charming Key West Cottage with large back yard and ROOM FOR A BIG POOL! Pack your flip flops and leave your worries at the door! This enchanting Key West gem is ready to make your island dreams a reality! Nestled in the heart of the Conch Republic, 2005 Fogarty Avenue is the kind of home that makes you exhale the moment you arrive. This beautifully updated 2 bedroom home has a bonus room for 3rd bedroom with own private full bath. The home is bursting with Key West charm and curb appeal! From the moment you step inside, you'll fall in love with the character and that unmistakable colorful warmth that only Key West living can deliver. Best of all? It's fully furnished and completely move-in ready. Just bring your toothbrush and your sunscreen, because everything else is already waiting for you.The versatile bonus space offers endless possibilities! Want a home office, guest overflow, art studio, workshop, or your very own private retreat? Step outside and discover the real showstopper: a spacious, lushly landscaped backyard that's practically begging for a sparkling pool 🏊. Whether you envision weekend soirées under the stars, a private tropical oasis, or the ultimate vacation rental income producer, this backyard delivers the canvas. Practical perks? You've got those too. Off-street parking is a rare and treasured luxury in Key West and this property has it. No more circling the block after a long day at the beach. Located just moments from world-famous Duval Street, celebrated dining, vibrant nightlife, the Historic Seaport, and those legendary Key West sunsets 🌅, this property places you at the very center of the island lifestyle while offering a peaceful, private retreat to come home to.✨ Furnished & Move-In Ready, updated, Expansive Backyard with Pool Potential, Off-Street Parking, central Key West Location. If you are searching for a full-time residence, a vacation escape, or a high-demand rental investment, 2005 Fogarty Ave checks

2005 Fogarty Ave, Key West
416 Fleming St, Key West
$3,500,000
5 Beds ⋅ 5 Baths ⋅ 620434 MLS
First Time on the Market in 26 Years! Just 79 steps from Duval Street, this extraordinary Historic Victorian estate presents a rare opportunity to own one of Key West's most iconic and meticulously maintained properties. Featuring 6+ Off-Street Parking Spaces, 5 bedrooms and 5 bathrooms, this stunning residence embodies the Key West lifestyle with expansive wraparound porches,timeless architectural details, and an unbeatable Old Town location.Originally renovated in 2001 and thoughtfully updated through 2025, the property blends historic character with modern functionality.. Situated on a generous 6,700-square-foot lot, the property offers parking for up to nine vehicles--an exceptional amenity in Old Town Key West--with ample space remaining for the addition of a private pool. Enjoy picturesque views of the surrounding historic district from the expansive porches while embracing the relaxed island atmosphere that defines Key West living. A unique and valuable feature of the property is its 15,000-gallon underground rainwater harvesting cistern, measuring approximately 11' x 13' x 19'. Designed and constructed by a retired Boeing piping engineer, the system incorporates a dual-chamber design, allowing one chamber to remain in service while the other is isolated for inspection, cleaning, and maintenance. The home's roof drainage system has been professionally plumbed to collect and direct rainwater into the cistern, with a diverter valve that allows water to be routed either into storage or discharged into the yard. With the addition of a pump, this impressive system can be reactivated for irrigation and other sustainable water-management uses.Offering historic significance, income potential, abundant parking, modern updates, and a truly rare engineering feature, this exceptional property is a one-of-a-kind opportunity in the heart of Old Town.Corner Lane Lot: dimensions 50' x 134 Bike Rack Stays!

416 Fleming St, Key West
3746 Paula Ave, Key West
$895,000
4 Beds ⋅ 2 Baths ⋅ 620315 MLS
This large home on an extra large 6300 sf corner lot is an excellent opportunity for a renovation project. The main home is just under 1600 sf and consists of 4 bedrooms and 2 bathrooms and there is also a good sized detached structure of almost 200 sf that could be turned in to, among other ideas, an extra bedroom, artist's studio or pool cabana. The home had the roof replaced in 2014 and has storm shutters. There are terrazzo floors. The extra large lot has sour orange, Spanish lime and banana trees, off street parking and plenty of room for a pool.

3746 Paula Ave, Key West
1227 20th, Key West
$900,000
3 Beds ⋅ 2 Baths ⋅ 620104 MLS
*Seller Motivated, told us to bring all reasonable Offers. 3/1 with a guest cottage/office space at rear of property with private full bath and kitchenette. 4/2 with cottage. All just awaiting a Buyers personal taste!. Huge lot with incredible area for big a beautiful pool! This is a perfect family 3/1 home in one of the best New Town neighborhoods. This fully gated home sits on a massive 7000 sf oversized lot and is completely move-in ready. The home boasts three bedrooms and one bath. The floor plan in the kitchen and living area flows perfectly for open living. Glass French doors open to the back patio (that could be enclosed for Florida room) and look out at the massive green lawn and native trees. The large back yard is perfect for expansion or creating your very own tropical oasis. Set back in complete privacy is a beautiful guest suite/office space with bath. The side yard with an additional privacy fence is perfect boat parking. This property is a must see! Occupied so must allow 24 hour notice.

1227 20th, Key West
1511 17th Ter, Key West
$2,499,000
3 Beds ⋅ 4 Baths ⋅ 620092 MLS
Stunning modern home in New Town offering 2,525 sq. ft. of beautifully designed living space on an 8,250 sq. ft. lot. This 3-bedroom, 2 full + 2 half bath home features a desirable split floor plan with a private primary suite, complete with a walk-through closet and spa-like ensuite bath, plus two guest bedrooms and a full bath. The open-concept living, dining, and kitchen area is ideal for entertaining, highlighted by a 15-ft island and high-end Viking stainless steel appliances. The chef's kitchen also includes a wine cooler, ice maker, warming drawer, dual beverage drawers, and a dedicated coffee/wine station. Additional features include a walk-in pantry with drop-down desk, separate laundry room, and convenient half bath. Outdoor living is just as impressive, with French doors opening to a private backyard oasis featuring an Ipe wood deck, outdoor kitchen, outdoor shower, and an air-conditioned half bath. Enjoy the large heated pool and spa surrounded by lush landscaping. The property also offers a covered dual carport with built-in storage and additional brick parking for guests. Located just down the road from a public boat ramp and perfect for sunrise and sunset walks.

1511 17th Ter, Key West
1800 Atlantic Blvd Unit 427C, Key West
$1,025,000
2 Beds ⋅ 2 Baths ⋅ 619778 MLS
This spacious two-bedroom, two-bath penthouse condo boasts a stunning balcony with ocean views, making it the perfect place to relax and enjoy the breathtaking scenery. The beautifully designed kitchen features a breakfast bar, granite countertops, and stainless steel appliances, making it a chef's dream come true. The stunning living room and dining room are flooded with natural light, creating a bright, inviting space perfect for entertaining guests. The floor-to-ceiling windows allow the natural light to pour in and are complemented by the soaring cathedral ceilings, which add an extra layer of grandeur and elegance to the space. Ample storage throughout ensures you'll have plenty of space to store all your belongings and keep your new home tidy and organized. The best feature of this penthouse is the breathtaking sunrises you'll enjoy over the Atlantic Ocean. Whether you're sipping your morning coffee or simply taking in the view, this condo will provide the perfect setting for relaxation and rejuvenation. The complex: One of the best parts of 1800 Atlantic is its private beach. You can soak up the sun, enjoy the stunning ocean views, or dip in the Olympic-sized heated pool while relaxing within this gated and secured oceanside community. For those who love staying active, three lighted tennis courts are perfect for a friendly game with friends or a competitive match, and the fitness center is fully equipped with everything you need to stay in shape and achieve your health goals. With storage and covered garage parking, you'll have plenty of space to keep all your belongings safe and secure. With its tropical resort-style setting and luxurious amenities, 1800 Atlantic is the perfect place to call home.

1800 Atlantic Blvd Unit 427C, Key West
1430 Vernon Ave, Key West
$9,888,000
3 Beds ⋅ 2 Baths ⋅ 619724 MLS
Fabulous Find on the Atlantic Side of Key West! Welcome to a truly unique opportunity in the heart of Key West. As the last and only remaining undeveloped property in the Historic Commercial Tourist District (HCT zone), this listing presents a rare and final chance to create something extraordinary. Imagine waking up to breathtaking, unobstructed ocean and beach views every day. Seabirds passing overhead, gentle breezes arriving at your lanai--it's an experience like nowhere else. This is island living at its finest! Permitted HCT uses include: Single-family and two-family residential dwellings, Multiple-family residential dwellings, Restaurant, Business and professional offices, Hotels, Motels, transient lodging, and more. This two-story home comes equipped with two separate electric meters. This exceptional property is truly one of a kind, with no identical or closely similar listings anywhere in Key West. The ideal circumstances are here and now-- an unparalleled combination of an oversized ocean-view lot, located just three blocks from Duval Street, the gateway to downtown. Spanning 8,700 square feet, this property offers ample space for your creative vision, whether you dream of building a luxurious residence, alongside a commercial venture boutique hotel, or restaurant, -- this and more are supported by HCT zoning. This property is all about the excitement of shaping a new vision for a future in paradise. Let your imagination run wild and transform this blank canvas into something extraordinary. Don't miss out on this once-in-lifetime opportunity--call today for your private tour and start envisioning your future in Key West!

1430 Vernon Ave, Key West
1516 17th Ter, Key West
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 619723 MLS
DUPLEX! Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath. There is also a laundry room with additional storage space. The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.

1516 17th Ter, Key West
1516 17th Ter, Key West
$1,875,000
4 Beds ⋅ 3 Baths ⋅ 619698 MLS
Discover the breathtaking corner property at Sunrise Shores, set on an expansive lot exceeding 13,000 square feet. POOL! The main residence offers over 1,750 square feet of living space, complemented by a detached guest cottage of 640 square feet. This meticulously maintained property has been cherished by its owners. The main home features three bedrooms and two bathrooms. It boasts a thoughtfully designed layout that includes a spacious family room and a large living room with a fireplace that opens up to the lanai. The primary bedroom provides direct access to the pool area and features an updated bathroom and a generous walk-in closet. The second bedroom also opens to the pool area, while the third bedroom is conveniently located next to the updated hall bath. There is also a laundry room with additional storage space. The detached guest cottage includes one bedroom and one bathroom. This property is perfect for owner-occupiers, investors, multi-generational living, and more.

1516 17th Ter, Key West
1017 Angela St, Key West
$2,550,000
3 Beds ⋅ 4 Baths ⋅ 619579 MLS
Step into a residence that has captured the national spotlight. Recently honored as a Wall Street Journal ''House of the Week,'' 1017 Angela Street is a 118-year-old Old Town cottage masterfully reimagined for the modern connoisseur. Tucked away on a tranquil lane, yet moments from the Historic Seaport and Duval Street, this three bedroom, three and a half bath home is the ultimate blend of calm island style and sophisticated Key West living. From the quintessential front porch to the vibrant, playful interiors, every inch of this home radiates personality. The heart of the residence features rare, historic Dade County Pine walls and floors bathed in natural light, creating a warm, textured backdrop for the home's contemporary finishes. The thoughtfully designed L-shaped layout effortlessly connects the chef's kitchen-complete with granite countertops and stainless appliances-to the bar and living areas. This social heart of the home seamlessly merges with an expansive dining area, where impact-rated French doors invite the island breeze, creating a natural environment for entertaining. The floor plan includes a coveted first-floor primary suite for ultimate convenience. The home's artistic soul is further defined by a series of custom murals by artist Haley Leeper, most notably the hand-painted staircase, which creates an artistic transition to the second floor. Upstairs features a second primary bedroom with a spa-inspired bath and an intimate reading nook and an additional guest suite. The backyard is a secluded oasis, boasting a heated pool and spa with an upgraded system, outdoor shower, and Trex decking. Framed by lush tropical foliage and a magnificent, mature mango tree, this space offers a level of privacy and shade. Complete with off-street parking and a distinguished track record as a top-performing monthly rental, 1017 Angela Street is a ''turnkey'' treasure that perfectly balances historic architectural significance with lucrative investment potenti

1017 Angela St, Key West
2805 Flagler Ave, Key West
$874,999
3 Beds ⋅ 2 Baths ⋅ 619565 MLS
This sophisticated residence features off-street parking for two vehicles or a boat and is just a block away from the community boat ramp. Recent upgrades include hardie board siding, acoustic, and hurricane-rated doors and windows. An independent storage shed that offers additional storage space. The backyard provides a serene outdoor area perfect for enjoying the island lifestyle. The focus on high-quality finishes, expansive outdoor living, and an inviting design radiates luxury and comfort, making it ideal for entertaining friends and family. The location provides convenient access to exceptional dining, coffee shops, shopping, as well as recreational amenities such as sports venues and schools. Its proximity to the beach and downtown, coupled with low-maintenance landscaping, enhances its appeal and renders it a perfect choice for embracing the island lifestyle with luxury and comfort.

2805 Flagler Ave, Key West
1618 Flagler Ave, Key West
$749,000
2 Beds ⋅ 2 Baths ⋅ 619553 MLS
First time ever on the market! This is an excellent opportunity to own a charming single-family home in Key West. Lovingly maintained and custom-built for the current owners, this property has remained in the same family for over 60 years. This tranquil residence features 2 bedrooms and 2 bathrooms and sits on a spacious 5,016 sq. ft. lot. The home includes off-street, covered parking for one vehicle. Recent updates include central A/C and a new water heater. A detached metal storage shed provides additional storage space. The backyard offers a relaxing outdoor area--perfect for enjoying the island lifestyle. Inside, tile flooring runs throughout the home for easy maintenance. The yard features mature tropical landscaping with local fruit bearing trees. Centrally located, this property is just minutes from shopping, schools, dining, and beaches. This mid-century modern home offers great potential for upgrades, renovations, or possible additions to suit your needs. The property is being sold as-is and is currently tenant-occupied, offering flexibility for investors or future homeowners ready to create their own vision. Listing agents are related to the sellers.

1618 Flagler Ave, Key West
2922 Flagler Ave, Key West
$1,100,000
5 Beds ⋅ 3 Baths ⋅ 619531 MLS
With five bedrooms and three bathrooms, it seems perfect for families or hosting guests. The location ensures easy access to fantastic dining, coffee shops, and shopping, along with recreational options like sports venues and schools. The emphasis on beautiful finishes and an inviting floor plan suggests a luxurious yet comfortable living space, ideal for entertaining. Plus, the proximity to the beach and downtown, complemented by lush landscaping and tropical breezes, adds to its charm.

2922 Flagler Ave, Key West
3034 Riviera Dr, 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
1620 Jamaica Dr, Key West
$1,975,000
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
3930 S Roosevelt Blvd Unit S205, Key West
$559,000
3 Beds ⋅ 2 Baths ⋅ 618678 MLS
New lower price and now ready to occupy, you can enjoy the best priced 3 BR Property on Key West! Stop throwing away money on rent and step into Key West homeownership with this 3 BR and 2 BA value. Properties like this are rare in the Key West market when considering the value pricing and the affordable costs of ownership with low condo fees, insurance and taxes. Offering granite tile floors, an upgraded kitchen, and crown molding and trim details, the condo is ideally located in the South Wing with a southeasterly view not affected by the laser hot afternoon sun. Along with an inviting sun drenched swimming pool, perhaps the best community fitness center in all Key West is located at Las Salinas. It features private access to cardio and strength rooms, has high quality equipment, and is spotless. For your convenience, nearby is a small grocery store and bus stop for easy transportation on Key West. The popular 2 mile long Smathers Beach promenade is just outside the entrance and perfect for morning walks, biking, or just to enjoy sunrises and sunsets. Now competitively priced for only $559,000. Call for your private tour.

3930 S Roosevelt Blvd Unit S205, Key West
2914 Fogarty Ave, 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
103 Front St, 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
1229 5th 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
906 Johnson St, Key West
$5,500,000
6 Beds ⋅ 6 Baths ⋅ 618573 MLS
Experience the grandeur of this exceptional six bedroom, five and a half bath estate located on one of the most exclusive streets in Key West. A stunning wall of bougainvillea and the stately front porch welcome you to this 3,751 square foot property on an expansive 10,750 square foot lot that embodies historic Key West architecture. The main residence features four bedrooms, three and half baths of elegant living spaces, including a first-floor mother-in-law suite. Timeless design is found throughout with abundance of natural light and views of the lush, exotic landscape out every window. The great room features 12' ceilings, a curved wall of windows and French doors that lead to the serene, covered porch and outdoor dining space. The kitchen is a chef's dream equipped with new Viking appliances, ample counter space, and a view that overlooks the gorgeous, azure pool. The second level includes a spacious primary suite and two additional guest rooms, one of which has a balcony with treetop views and the island's best spot to view the spectacular 4th of July firework show. Two charming detached guest cottages tucked amongst the gardens offer secluded retreats each with full baths and one offering a living room and kitchenette. The outdoor oasis is defined by the oversized L-shaped pool and outdoor kitchen with built-in Viking grill; the perfect space for entertaining. This property is an exceptional, private sanctuary at an unbeatable location just one block from the crystal-clear Atlantic, tennis and pickleball courts, the esteemed Casa Marina Hotel and iconic White Street Pier. Don't miss the opportunity to call this remarkable estate your home! Seller is a licensed real estate broker and related to the listing agent. Seller is a licensed real estate broker and related to the listing agent.

906 Johnson St, Key West
1521 Rose St, Key West
$798,000
2 Beds ⋅ 1 Baths ⋅ 608965 MLS
Tare Down You can build your dream house to your specifications just 4 houses to the beach. Close to the White Street pier. Walk to pickle ball and tennis courts. Higgs beach is just 3 minutes away. Ride your bikes to Duval Street only 1.3 mile away. This large corner lot is perfectly located. Even the birds know when to fly South.

1521 Rose St, Key West
3675 Seaside Dr Unit 342, Key West
$599,000
2 Beds ⋅ 2 Baths ⋅ 618834 MLS
Welcome to your private slice of paradise at 3675 Seaside Drive, Unit 342. This highly sought-after end unit offers exceptional privacy, abundant natural light, and a tranquil coastal setting. The bright, open-concept floor plan is designed for effortless island living, with a spacious living and dining area that flows seamlessly from the well-appointed kitchen. The split-bedroom layout provides comfortable retreats, while generous storage enhances everyday convenience. Step onto your private balcony to enjoy refreshing ocean breezes and peek-a-boo ocean views overlooking the peaceful Salt Ponds Preserve - a protected area ensuring your natural backdrop will remain unobstructed for years to come. Beautifully maintained grounds, a recently renovated resort-style pool and heated spa, fitness center, tennis courts, and gated entry create an exceptional lifestyle in one of Key West's most desirable communities. With conventional financing now available, buyers have increased lending flexibility. Furnishings are negotiable, making this move-in-ready residence an outstanding opportunity to own your piece of paradise.

3675 Seaside Dr Unit 342, Key West
600 Elizabeth St, Key West
$4,300,000
4 Beds ⋅ 6 Baths ⋅ 617513 MLS
**31 photos have been virtually staged and enhanced to assist buyers in visualizing design and decor options for this home.** Casa Sapodilla introduces itself with the kind of presence that feels both storied and serene. Built in 1996 and set at 13' elevation on Solares Hill, the residence pays homage to the architectural romance of Old Town's most celebrated homes.. broad verandas, intricate trim work, and Brazilian Cherry hardwood floors that recall a bygone era of island craftsmanship. Inside, the home unfolds in layers of refinement. Sunlit rooms connect gracefully to the outdoors through French doors and deep porches. The main house's split-level design elevates the primary suite with its own private staircase, while two additional bedrooms ascend another, creating a sense of calm seclusion. A separate pool suite, complete with private entrance, extends the home's versatility. The kitchen is anchored by a suite of premier appliances.. including a new SubZero refrigerator and a refurbished Viking gas range, and framed by custom cabinetry and built-ins. Recent upgrades such as the 2025 metal roof, updated HVAC systems, and a 24 kW Generac whole-house generator reflect meticulous stewardship. Outside, the grounds rise to the level of a private resort. Tropical gardens wind around stone pathways, illuminated at night by soft landscape lighting. A heated saltwater lagoon-style pool, resurfaced in 2025, curves around natural rock formations, a spa, and three cascading waterfalls. Every vista offers a moment of stillness.. from the shaded verandas to the courtyard designed for open-air dining. A one-car air-conditioned garage, currently serving as an art studio, and a two-car driveway complete the thoughtful layout. Just blocks from Duval Street and the Key West Historic Seaport, Casa Sapodilla is both connected and deeply private.. a luxury retreat rooted in island elegance.. Inquire within for details on the low insurance costs available for this home

600 Elizabeth St, Key West
1901 S Roosevelt Blvd Unit 401E, Key West
$1,425,000
3 Beds ⋅ 2 Baths ⋅ 618248 MLS
Discover the rare opportunity to own a premier developer's unit in one of Key West's most desirable waterfront communities. Perfectly positioned just across the street from world-famous Smathers Beach, this spacious 3-bedroom, 2-bath condo blends coastal luxury with unbeatable island convenience. Inside, expansive living spaces open to large windows and glass doors showcasing ocean views and endless natural light. The open-concept kitchen flows seamlessly into the dining and living areas—ideal for entertaining or relaxing after a day on the sand. Retreat to the ocean-view primary suite, complete with generous closet space and private bath. Two additional bedrooms offer the flexibility for guests, family, a home office, or rental income. Step outside and enjoy resort-style amenities—lush tropical grounds, shoreline paths, sparkling pool, and easy access to water sports, biking, and Key West's sunset scene. Whether you're seeking a primary residence, island getaway, or investment opportunity, this condo delivers everything that makes Key West living unforgettable. Highlights: *Rare developer's unit with expanded layout/premium features *Just steps to Smathers Beach, bike paths & sunrise walks *3 Bedrooms / 2 Bathrooms *Assigned covered parking bay and storage unit *Resort amenities & gated community *Minutes to Old Town, dining, airport & nightlife Your Key West waterfront life starts here—schedule your private showing today!

1901 S Roosevelt Blvd Unit 401E, Key West
508 Grinnell St, Key West
$2,595,000
3 Beds ⋅ 3 Baths ⋅ 613986 MLS
Traditional key West home impeccably maintained, boasts three bedrooms, three full baths with plenty of closets throughout the home. Large private lot with a heated pool featuring a waterfall. Nice size cabana room that has a/c and heat with ample closet space can be a fourth bedroom. This home has large rooms for entertaining, quaint front porch and off street parking. A true treasure.

508 Grinnell St, Key West