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$3,600,000
4 Beds ⋅ 4 Baths ⋅ 620913 MLS
Discover modern island luxury at 119 Simonton Street, a premier end-unit townhouse nestled within the exclusive gated community of Old Town Villas. Built in 2018 and spanning a generous 2,691 square feet, this residence seamlessly blends sophisticated contemporary design with the timeless allure of Key West. The interior features new white oak flooring that leads you through an open-concept living space. The kitchen is a true standout, boasting elegant granite countertops and a custom kitchen island--a unique feature in the community. For the ultimate convenience, a private elevator services all four floors of the home, transporting you from the air-conditioned two-car garage to the spectacular rooftop terrace where you can view daily sunrises over the Historic Key West Marina and sunsets over Mallory Square, both a very short walk away. The top floor features a rare full bathroom and a flexible bonus room ideal for a home office or guest suite. Whether you're mixing drinks at the custom wet bar or lounging on the terrace, this level serves as the ultimate private retreat for taking in breathtaking panoramic views. Peace of mind is built into the architecture with full impact-rated windows and doors and a durable metal roof, ensuring the home is as secure as it is beautiful. The third floor has two primary bedrooms featuring large walk-in closets and balconies. The lifestyle offered here is unparalleled, situated just one block off the vibrant energy of Duval Street. You are steps away from the island's best dining and boutiques, yet you can retreat instantly to the quiet security of a gated community. Spend your afternoons lounging by the large tropical community pool and cabana area, enjoying a level of comfort and convenience unsurpassed in the heart of Old Town. With a rare two-car garage and an unbeatable location, this residence captures the very best of the Florida Keys lifestyle.

119 Simonton St, Key West
$1,400,000
4 Beds ⋅ 2 Baths ⋅ 620808 MLS
This one is a must see! Spacious 4 bedroom, single family in the 'Pearlman Heights' neighborhood of New Town KW that has undergone recent renovations-upgrades. New roof, kitchen, windows (impact rated), on demand water heater, pool pump, Central AC condenser / air handler, light fixtures, ceiling fans, crown molding, interior doors & more. Nice set up for enjoying the KW weather or entertaining because the den, kitchen & dining areas flow out to the pool deck with 32 fl long in ground pool. No interior step downs or tripping hazards. Located on a one-way street with green dividing median on 17th St. Carport covers the off-street parking space plus additional on street parking. Has an exterior 15 X 7 storage / laundry room. Convenient location close to schools, medical offices, grocery stores & shopping, dining, etc..

1105 17th St, Key West
$1,800,000
4 Beds ⋅ 3 Baths ⋅ 620682 MLS
Wonderful Old Town Meadows home with 4 Bedrooms, 3 Baths, on a nearly 5000 sq ft lot, this property has a separate Guest Cottage, wrap around front porch, lap- pool, and more! Wood flooring throughout, with 2 living areas leading to the kitchen with Italian designed built in cabinetry . The Primary Bedroom is spacious, and has built-in Custom cabinetry. Steps from the kitchen is a lap pool , extensive decking, and lots of room for outside dining and relaxation. The Guest Cottage has a full bathroom, and exposed beam ceilings. The property is completely fenced and feels very private.There is a curb cut already- for potential off street parking. Buyer to verify!

1407 Petronia St, Key West
$4,995,000
4 Beds ⋅ 5 Baths ⋅ 620618 MLS
Welcome to an extraordinary oceanfront residence in the exclusive Casa Caselles community, where two townhomes have been masterfully combined into one spectacular 4,224 sq. ft. luxury retreat with private interior elevator accessing all floors . Completely reimagined, this one-of-a-kind residence showcases exceptional craftsmanship, sophisticated design, and effortless waterfront living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living areas, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the home is designed for both everyday living and grand-scale entertaining. An oversized island anchors the chef's kitchen, complemented by custom European-style cabinetry, premium quartz countertops, and an impressive suite of appliances including a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker and wine refrigerator, and Perlick refrigerator/freezer drawers. The inviting family room features an electric fireplace and a custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry, creating an ideal space for entertaining. Throughout the home, travertine flooring, custom built-ins, abundant hidden storage, recessed lighting, remote-controlled window coverings, and in-wall TV wiring reflect meticulous attention to detail. Every major system has been replaced, including electrical, plumbing, insulation, HVAC systems, 12 hurricane-rated sliding glass doors, and a whole-house generator. The luxurious primary suite features a custom walk-in closet, while every bedroom enjoys private balcony access. A guest suite features a zero-entry shower, offering added comfort and accessibility. Beautifully tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance everyday living. Residents enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

1616 Atlantic Blvd Unit 11, Key West
$1,350,000
4 Beds ⋅ 5 Baths ⋅ 620612 MLS
THIS IS THE PLAY. Big lot. Big upside. Atlantic Boulevard address. 1503 Atlantic Boulevard brings together the pieces that matter most in Key West: land, location, pool, and multi-unit flexibility. Atlantic Boulevard has only a handful of true residential opportunities, and this one brings the rare combination of land, pool, and multi-unit upside. Set on an approximately 8,050 square foot lot, this Atlantic-side property offers roughly 2,750 square feet of living area with a flexible multi-unit configuration and a concrete pool anchoring the outdoor space. The existing home would benefit from a major renovation and thoughtful updating for today's standards, creating a compelling opportunity for an investor, owner-user, or buyer with vision. In a market where land is the luxury, the lot itself is a major part of the story. The scale, pool, and layout create the foundation for a refreshed tropical compound, income-producing retreat, or reimagined Key West residence. Located along Atlantic Boulevard, the property is close to beaches, Old Town, Casa Marina, schools, dining, and the everyday ease that makes island living so desirable. Whether held as a long-term income property or transformed into something more polished, 1503 Atlantic Boulevard offers the kind of upside that is increasingly hard to find in Key West.

1503 Atlantic Blvd, Key West
$1,050,000
4 Beds ⋅ 2 Baths ⋅ 620461 MLS
Duplex with adjoining commercial lot for sale. Duplex has 1,342 square feet of living space on a 2,841 sq ft lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. The adjoining 2,244 square foot commercial zoned lot would be ideal for one or more food vendor trucks, with excellent visibility and heavy traffic. Make an offer today!

1421-1425 2nd St, Key West
$1,050,000
4 Beds ⋅ 2 Baths ⋅ 620459 MLS
Duplex with adjoining commercial lot for sale. Duplex has 1,342 square feet of living space on a 2,841 sq ft lot with 2 two bedroom one units generating $74,400.00 annually. Units have been recently renovated and ready for new tenants. The adjoining 2,244 square foot commercial zoned lot would be ideal for one or more food vendor trucks, with excellent visibility and heavy traffic. Make an offer today!

2001 Flagler Ave, Key West
$979,000
4 Beds ⋅ 2 Baths ⋅ 620453 MLS
When value matters, this solid concrete New Town home stands apart with one of the most compelling price-per-square-foot opportunities on the market. Substantial 4-bedroom, 2-bath home featuring a dedicated office, offering an exceptional combination of comfort and functionality. Situated on an expansive 8,448-square-foot corner lot, the property provides 2,111 square feet of living space, two driveways, off-street parking with an attached carport, a Tesla charging station, and ample room to add a pool. Designed for easy living and entertaining, the open-concept kitchen and living area is enhanced by soaring cathedral ceilings with exposed beams and an abundance of large, light-filtering windows that create a bright and inviting atmosphere throughout. A welcoming front porch, set back amongst mature trees, provides the perfect place to relax and unwind. The elevated home features double-pane windows, noise-dampening door improvements, a V-crimp metal roof, and beautiful terrazzo floors that add timeless Key West character. The solid concrete construction offers lasting durability and an excellent foundation to fine-tune and personalize the home to suit your vision. The fully walled property provides privacy and generous outdoor space. With its larger-than-average footprint, oversized corner lot, two driveways, and endless potential for a backyard pool oasis, this home presents an outstanding opportunity to enjoy the very best of Key West living. Whether you're searching for a comfortably sized family home just or a property with the perfect canvas to create your dream home, this opportunity offers exceptional value.

1500 5th St, Key West
$2,685,000
4 Beds ⋅ 5 Baths ⋅ 620332 MLS
Brand-new construction in one of Key West's most desirable residential neighborhoods, the Casa Marina area of Old Town, just blocks from upper Duval Street and four blocks from the beach. This 4 bedroom, 4.5 bath single-family home blends modern durability with relaxed island living, offering the ease of low-maintenance ownership in the highly sought-after X flood zone. Built in 2026 to Florida's toughest standards, the home features concrete board siding, impact doors and windows, and an elevated first floor. The construction is designed to withstand winds up to 180 MPH. Inside, spacious living areas with high ceilings flow comfortably to a private outdoor retreat with an inground pool and water features. All bedrooms are en-suite, with one located on the first floor. A $15,000 builder appliance credit allows you to choose the finishes and appliance brands, at cost, that best suit your lifestyle. Off-street parking adds everyday convenience, while reclaimed wood accents from the historic schooner Western Union bring a meaningful connection to Key West history into the architecture. Quiet, private, and close to everything, this home offers luxury, walkability, and the best of Key West living.

1316 Royal St Unit 6, 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
$3,495,000
4 Beds ⋅ 5 Baths ⋅ 620222 MLS
Caroline Street, steps from the Historic Seaport. This is the Key West people picture before they ever get here. Built in the late 1800s as a cigar factory, when Key West was the cigar capital of the country. That origin is why it lives so much larger than the cottages around it: the volume, the ceiling height, the proportions of a working building rather than a bungalow. The Dade County pine is original, refinished rather than replaced, and irreplaceable. What 2023 changed was everything behind it -- raised to modern flood elevation, impact-rated windows and doors, and finishes chosen by a designer who wasn't in a hurry. Native coral walls, Jerusalem limestone, terrazzo, and marble under high ceilings. Out front, double balconies span the facade -- the real living room here. Coffee on the upper, cocktails on the lower, and Caroline Street putting on its show below: the walk to the Seaport, the whole slow parade of Old Town. Out back, collapsing glass doors open to the garden: a heated and chilled plunge pool with waterfall, walled and private -- the kind of courtyard that makes 4pm the best hour of the day. Four bedrooms, four en-suite baths, plus a guest half bath. The oversized upstairs primary has walk-in closets and a spa-caliber bath with double shower, artist-made cabinetry, and coral detail you won't see twice. A second primary on the main floor adds flexibility, plus a loft/office upstairs. The kitchen was built for how people actually entertain here: a six-seat island, full JennAir package, open flow to the living and dining rooms. And it earns from day one. High six-figures in booked rental revenue transfers with the sale, repeat guests already on the calendar. Residence, winter escape, or income property -- it does all three. Sold furnished. No HOA. Seller financing possible. Three minutes to Duval. One minute to the shrimp boats. Homes on this block rarely trade, and almost never finished like this.

710 Caroline St, Key West
$3,650,000
4 Beds ⋅ 3 Baths ⋅ 620188 MLS
Stunning possibilities abound for this home on a double lot on the best street in the much sought after Casa Marina neighborhood in Key West. 1017 Washington Street is a renovation away from being your trophy property. The existing house has lots of room with 2,604 square feet of finished space with 4 bedrooms and 2.5 bathrooms. The oversized lot has even more room with 10, 724 square feet, a large swimming pool and an outdoor shed perfect for outdoor kitchen and living space. The property has never flooded and sits above flood. The possibilities are endless. Come see it today.

1017 Washington St, Key West
$1,699,000
4 Beds ⋅ 3 Baths ⋅ 620042 MLS
Tucked behind the gates of the exclusive Marquesa Court, an intimate enclave of just nine private residences, this exceptional home offers privacy, security, and a central Key West location that places you moments from everything the island has to offer. Built in 2006 above flood elevation and thoughtfully constructed with impact-rated doors and windows, this well-designed residence combines peace of mind with timeless comfort. The spacious floor plan features 4 bedrooms and 3 full bathrooms, offering flexibility for full-time living, a second home, or hosting family and guests. The oversized primary suite is a true retreat, complete with a generous spa-inspired bath featuring a jacuzzi tub, separate shower, private water closet, and direct access to the upstairs balcony overlooking the pool and the tranquil backdrop of the adjacent nature preserve. The first-floor fourth bedroom offers excellent versatility--ideal as a guest suite, home office, or den. What truly sets this property apart is the rare combination of privacy, gated exclusivity, and natural serenity, creating a peaceful residential feel while remaining centrally located in Key West. A wonderful opportunity for the next owner to enjoy island living in one of Key West's most desirable hidden neighborhoods.

1030 Sandys Way, Key West
$1,678,000
4 Beds ⋅ 4 Baths ⋅ 619991 MLS
Welcome to 2519 Staples Avenue, a fully reimagined residence in the heart of Midtown Key West, set on a rare 10,000 sq ft corner lot along one of the area's most bicyclable and desirable streets in Midtown. Recently completed renovations offer the opportunity to be the first to live in this thoughtfully rethought home, where modern upgrades meet relaxed island living. Spanning approximately 2,100 sq ft, the property features 4 bedrooms and 3.5 bathrooms, with a layout designed for both comfort and functionality. The primary suite serves as a private retreat, complete with direct access to the backyard, a spacious walk-in closet, and a beautifully appointed ensuite bathroom. Outdoor living is where this home truly stands out. A newly installed pool with elegant deck jets creates a serene, resort-style setting, fully enclosed for privacy. The new addition of a bright and airy pool room offers a seamless indoor-outdoor flow- perfect for entertaining or unwinding. There is a separate sitting and dining area for eating and lounging el fresco. Beautiful mature fruit trees provide shade and produce fruit annually. Additional upgrades include all impact windows and doors, providing peace of mind and energy efficiency throughout. New sewer and plumbing pipes to the road. New electrical and a new water heater. There is plenty of parking for a boat, a truck, a golf cart and a car. Properties offering this combination of lot size, location, and new construction-level renovations are exceptionally rare in Key West. Whether you're seeking a full-time residence, a family home, or a vacation retreat, this property delivers. House is being offered fully furnished minus personal items, art, and rugs. A true standout opportunity in Midtown--don't miss it.

2519 Staples Ave, Key West
$1,299,000
4 Beds ⋅ 2 Baths ⋅ 619738 MLS
FLIP FLOPS INLCUDED! Some homes are just addresses. This one is a lifestyle. Tucked into the heart of Old Town Key West, this beautiful historic Conch home is wrapped in the warmth of original Dade County pine and rich hardwood floors -- the kind of craftsmanship that simply isn't built anymore. The main house offers three bedrooms and a fully renovated bath, anchored by a large kitchen with generous cabinet space.. A fully enclosed porch is your place for morning coffee, chatting around the table or dining while overlooking the pool. Central air conditioning keeps things cool. Every window and door has been upgraded to impact, giving you peace of mind alongside the charm. Step outside and the magic continues. A sparkling pool with a waterfall feature and Trex decking invites you to linger. An outdoor shower makes coming in from the water effortless. The fully fenced front and back yards create a private tropical sanctuary, and off-street parking -- a true luxury in Old Town -- takes the stress out of coming home. The guest cottage is its own retreat, offering one bedroom, one bath, and a Murphy bed that makes the space as flexible as your plans. Whether it becomes a private getaway for family and friends, a creative studio or a detached office, it gives this property a versatility that is genuinely rare. The location is the final piece that makes everything click. A ten-minute walk from Duval Street -live music, art galleries, open-air restaurants, theaters and the electric pulse that makes Key West unlike anywhere else on earth. 7 minutes the other way brings you to the White Street District know for Fausto's Food Palace, where locals have shopped for generations, and the legendary Sandy's Café. This property comes fully turn-key, bedding, housewares, pool toys, bicycles, and yes, flip flops are included. Whether you wanting a second home, a monthly vacation rental or simply ready to walk through the door and start living living in paradise.

928 United St, 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
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 619703 MLS
Strong value-add multifamily fourplex investment opportunity with major capital improvements already completed. The property offers four two-bedroom residences totaling approximately 3,000 square feet, with each unit comprising approximately 750 square feet. The lower level includes two residences, while the upper level features two additional residences with approximately 960 square feet of combined balcony space. Major improvements include a new standing-seam metal roof, new impact-resistant windows and doors throughout, and completed concrete, stucco, and exterior work. The property is ready for the next owner to complete the remaining work and execute their preferred investment strategy. Once completed and delivered furnished, the property is projected to have the potential to generate more than $200,000 in annual gross rental income across all four units. Additional potential may include condominium conversion, subject to all applicable approvals and requirements. A compelling opportunity to complete, stabilize, and maximize a well-positioned Key West income-producing asset.

1224 2nd St, 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
$2,895,000
4 Beds ⋅ 5 Baths ⋅ 619665 MLS
Built in 2008, this expansive 3,220 sq ft residence sits on a nearly 5,000 sq ft lot and offers the perfect blend of comfort, style, and location. Centrally situated, you're just moments from beautiful beaches, top-tier dining, vibrant bars, museums, and all the attractions the area has to offer.Upstairs features three generously sized bedrooms, each with its own en suite bathroom and walk-in closet, providing privacy and convenience for family and guests alike. The main level is designed for living and entertaining, large open floor plan. An additional bedroom and bath on main floor with a door to the pool/deck area. The chef's kitchen is a standout, equipped with high-end stainless steel appliances including a 48-inch Viking gas range, refrigerator, ice maker, dishwasher, built-in steamer, wine cooler, and rich cherry cabinetry. Additional highlights include: Efficient 2-zone HVAC system, Impact windows and sliding glass doors, Beautiful Tigerwood flooring throughout. The exterior is equally impressive, featuring durable Hardi plank siding for low maintenance, Ipe wood decking, and a private pool surrounded by lush tropical landscaping. The fully fenced yard creates a serene and secluded outdoor retreat. The house also offers two off-street parking spaces, plus ample street parking for guests. A rare opportunity to own a spacious, well-appointed home in a prime location--this one truly has it all.

1320 South Street, Key West
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 619646 MLS
1421 Reynolds is a beautifully renovated mid century modern home located 3 blocks from Higgs Beach, one of Key West's best beaches and the perfect spot to watch the sunset. You will see the ocean from your driveway. You can walk or bike to Duval street, but live just far enough away to enjoy peace and tranquility. The spacious floor plan offers 4 bedrooms and 3 bathrooms. Vaulted ceilings throughout give it a sense of open space and the sliding glass doors in the great room open all the way for indoor outdoor living. All impact doors and windows allow lots of natural light to flood into the modern renovation in every room. Off street parking and room for a pool make this a rare opportunity in one of Key West's most coveted neighborhoods, the Casa Marina. In the front you will find a private zen garden adding outdoor space to the master bedroom. The kitchen has all stainless appliances with Viking, Samsung smart fridge and JennAir. This home was designed to enjoy the best Key West has to offer, from the interior to the outdoor space to the neighborhood itself. You will find yourself swimming in the ocean for sunset, walking to the Casa Marina Hotel for drinks overlooking the ocean, and having dinner on the beach at Salute's or Louie's Backyard. Owner/listing agent is a licensed FL Real Estate Broker.

1421 Reynolds St, Key West
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 619619 MLS
Some homes invite you in, and others make you want to stay. 1220 Georgia Street does both. Tucked into a quiet pocket of Old Town on a corner lot, the home feels peaceful and removed, yet everything you need is just moments away. A short walk takes you to neighborhood cafes, the beach, or a quick bike ride into the heart of town, while at home, the pace feels slower and more relaxed. The approach sets the tone. A marble and Coralina pathway leads through lush landscaping to a welcoming front porch and a striking antique front door that hints at the character inside. Step through and the space opens up with high ceilings and large windows that fill the home with natural light. The living areas flow easily together and draw you toward the outdoors, where a private backyard retreat awaits. Surrounded by mature tropical foliage, the cocktail pool and IPE deck create a setting that feels both secluded and inviting, perfect for entertaining or unwinding. The main house offers 3 bedrooms and 2 bathrooms, complemented by a separate 1 bedroom and 1 bathroom guest cottage that provides flexibility for visitors or a quiet escape. This is a home that feels well cared for, loved, and ready for its next chapter. A place where the details matter, but the feeling matters even more.

1220 Georgia St, Key West
$3,300,000
4 Beds ⋅ 4 Baths ⋅ 619548 MLS
Welcome to 214 Eanes Lane, a classic Key West property offering flexibility, character, and exceptional investment potential in a prime Old Town location. Located in an X flood zone, this property offers added peace of mind and potential savings on insurance--an increasingly valuable feature in today's market. This unique property is configured as two separate units, featuring a main two-story residence and a detached guest quarters, with a combined total of 2,573 square feet of living space. The detached unit is separately licensed and equipped with its own electric and water meters, providing true independence and strong income-producing potential. The main home offers a spacious and functional layout designed for island living. The first floor includes multiple living areas, with a generous living room, separate dining space, family room, and a well-appointed kitchen that opens to outdoor patio and deck areas--perfect for entertaining. Upstairs, you'll find three bedrooms, including a primary suite, along with multiple bathrooms and private balconies that capture the charm of Key West. The detached unit provides a private retreat complete with a bedroom, bathroom, kitchenette, and living space--ideal for guests, extended family, or rental income. Additional highlights include off-street parking for two vehicles, a rare and valuable feature in Old Town, as well as inviting outdoor spaces designed for relaxing and entertaining. Whether you're looking for a primary residence with additional income, a second home with flexibility, or a pure investment opportunity, 214 Eanes Lane delivers versatility and value in one of Key West's most sought-after neighborhoods.

214 Eanes Ln, 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
$939,000
4 Beds ⋅ 3 Baths ⋅ 619376 MLS
Welcome to your dream home in Midtown Key West! This 4-bedroom, 3-bathroom currently being used as a 3/2 with a mother-in-law suite. This property has endless possibilities property boasts a fenced yard, perfect for privacy and outdoor enjoyment. With a durable metal roof and tile floors throughout, this home combines comfort and style. Don't miss the opportunity to own a piece of paradise.!

1524 5th St, 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
$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
$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
$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
$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