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$4,375,000
5 Beds ⋅ 6 Baths ⋅ 616703 MLS
Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West. Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10' ceilings, impact glass, and abundant natural light. The chef's kitchen includes premium appliances, quartz countertops, pantry, and large island ideal for entertaining. Multiple verandas, balconies, and a rooftop observation deck deliver 360-degree sunrise and sunset views. Outdoors, enjoy your own sparkling infinity pool, expansive pool deck, and seamless flow to the water. Every residence conveys with an assigned dock space in a private boat basin featuring new composite docks with electric, water, and a fillet station—perfect for boating enthusiasts. Homes are equipped with Tesla Solar, an elevator, and generous storage. Resort-style amenities include a sport court for tennis, pickleball, and basketball, along with oceanfront lounge areas, hammocks, and opportunities for paddleboarding and kayaking. Just one block from a private airport, accessibility is unmatched. For investors, Seven Palms Cove is an exceptional opportunity: there are no rental restrictions, and nearby comparable properties generate over $300,000 annually. Whether as a forever home, luxury vacation retreat, or high-performing investment, Seven Palms Cove offers the perfect blend of exclusivity, comfort, and opportunity in the Florida Keys.

231 E Shore Dr Unit 4, Summerland
$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
$4,250,000
4 Beds ⋅ 4 Baths ⋅ 617294 MLS
An Oceanfront Masterpiece with Infinite Horizons Commanding a premier position above the crystal-clear waters of the Atlantic, this exceptional open-water estate represents the pinnacle of refined island living. With its highly sought-after southern exposure, 258 W Seaview Circle is immersed in golden sunlight throughout the day, offering uninterrupted panoramic ocean views and the gentle cadence of waves just steps from the residence. Beyond the protective breakwater, a pristine sandy shoreline and natural sandbar unfold—an idyllic extension of your private coastal sanctuary. Designed to seamlessly balance sophisticated entertaining with effortless relaxation, the estate features an impressive 112-foot bi-level dock and seawall, perfectly suited for the discerning boating enthusiast. The oceanfront terrace is anchored by a striking 50-foot lap pool, elevated eight feet above sea level to maximize views and serenity. Framed by a charming Tiki hut, lush tropical landscaping, and curated ambient lighting, the outdoor living spaces transform into an enchanting seaside retreat as evening falls. Inside, classic craftsmanship is paired with modern elegance. This four-bedroom, three-and-a-half-bath residence offers a coral rock fireplace, private elevator, and a generously proportioned gourmet chef's kitchen designed for both everyday indulgence and elevated culinary experiences. Every detail—from the architectural finishes to the meticulously maintained grounds—reflects exceptional care, quality, and pride of ownership. Whether hosting intimate gatherings beneath the stars, savoring tranquil mornings overlooking endless blue horizons, or setting out for a day on the water, 258 W Seaview Circle delivers an unrivaled lifestyle in Duck Key, widely regarded as the Middle Keys' most prestigious enclave. Residents enjoy access to two marinas, watersports, and local dining within this charming, golf cart-friendly island community.

258 W Seaview Cir, Duck Key
$4,195,000
5 Beds ⋅ 7 Baths ⋅ 620098 MLS
New Construction & Furnished in Key West. Experience timeless Key West charm blended with modern luxury in this stunning property, re-built completely to the historic standard of the original home. Located in the highly sought-after Casa Marina neighborhood just five blocks from Higgs Beach and six blocks from Duval Street, this residence offers the ideal balance of privacy and proximity to all that Key West has to offer. Step inside to discover over 900 square feet of wraparound Brazilian hardwood porches and a beautifully designed interior featuring custom-stained Heart Pine floors, Shiplap walls, and an abundance of natural light. The wide entrance hallway leads to a soaring great room with 20-foot ceilings and skylights, seamlessly connecting the living, dining, and kitchen spaces. The chef's kitchen is a true showpiece, boasting a large center island with seating for six, a wet bar, dual pantries, and a full Viking Professional appliance package. The main level includes a spacious master suite and two guest bedrooms, each with private baths and individual porch access. A convenient half bath is located off the hallway, while the laundry room--complete with an additional half bath--opens directly to the back deck and pool area. Enjoy Key West's outdoor lifestyle with a 15' x 8' pool with water feature, custom mahogany impact doors with transoms, impact windows, and lush professional landscaping. Upstairs, the charm continues with two additional ensuite bedrooms, walk-in closets, an interior balcony overlooking the great room, and a massive air-conditioned storage space spanning half of the second floor. Additional features include: Buried 250-gallon propane tank (servicing gas stove, on-demand water heater, generator-ready) and off-street parking with gate. This exceptional Casa Marina residence offers the best of Key West living--historic elegance, impeccable craftsmanship, and modern comforts.

1311 Grinnell St, Key West
$4,095,000
616391 MLS
MAIN KEY is a 145.5-acre private island with over a mile of pristine white sandy beaches on its east shoreline in Barnes Sound, Monroe County, FL. Its western and southern shoreline of over 4 miles of Mangroves reaching 30 to 50 feet tall provides a rookery that teams with gamefish, shellfish, sea mammals, and tropical birds. All owned by a TIIF Deed. With 12 upland acres, a substantial structure could be built with no ROGO requirements. In the 1930's and 40's, there were 3 large structures on the SE Government Lot area. A new dock permit with lift, platform, and mooring slip exists for the SE beach off the old homesite. An additional second permit is being applied for the south side of Main Key that will be 135 ft with a 40 ft platform and seven heavy pilings to moor a large vessel of up to 100 ft in length. A tide station was established by the USGS, later NOAA in the 1930's. 'The Tides at Main Key' was well known in Marine Weather forecasts on South Florida TV and NOAA Weather Radio for the Upper Keys and Florida Bay. Please contact the listing agents for more detailed information and documentation.

Main Ky, Key Largo
$4,000,000
4 Beds ⋅ 5 Baths ⋅ 619186 MLS
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 8, Islamorada
$4,000,000
4 Beds ⋅ 5 Baths ⋅ 619185 MLS
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for either full time residency or effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 7, Islamorada
$3,999,999
5 Beds ⋅ 4 Baths ⋅ 620964 MLS
Spectacular luxury modern home built in 2020, located on a corner lot with over 200 feet of waterfront. This home has four stories, featuring elegant finishes and a gourmet chef's kitchen with a quartz waterfall island. Enjoy the rooftop with new turf and spiral staircase to infinite bay views. The expansive outdoors includes a full kitchen, 80-foot dock with a 20k LB Neptune boat lift and 125 feet of seawall. Approved pool plans are available. This boater's paradise provides direct bay and ocean access via Jewfish Creek or Adams Cut. Additional features include a mosquito misting system and elevator. Available fully furnished and move in ready.

475 Bahia Honda Rd, Key Largo
$3,999,999
2 Beds ⋅ 2 Baths ⋅ 619064 MLS
Estate Opportunity Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. An existing legal nonconforming home with a waterfront swimming pool currently sits on the property and may be used as a residence or rental while architectural plans and permits are finalized, offering flexibility during the planning process. For buyers who understand the value of land in the Florida Keys, this offering represents something increasingly difficult to find: the opportunity to create a custom waterfront estate tailored entirely to your vision, rather than inheriting someone else's. A remarkable parcel for a remarkable build.

77340 Overseas Hwy, Islamorada
$3,999,000
4 Beds ⋅ 4 Baths ⋅ 620828 MLS
Welcome to your own private slice of Atlantic Ocean Paradise!. an Oversized Oceanfront Lot! Over 1/2 acre (23,500 sqf) Estate boasting 100 feet of absolute astonishing direct shoreline with ever changing crystal clear turquoise Atlantic Ocean waters plus an additional 100'x200' (20,000 sqf) of submerged Ocean Land. Arrive to expansive grounds, your own Private dock and what many consider exceptional,rare and extraordinary among Oceanfront homes/estates in all Islamorada is your own Private concrete boat ramp! Ideal for launching your pontoon, bay boat or jet skis with ease plus a generous parking for RVs, boats, trailers, and guests. Inside the main residence, discover three beautiful bedrooms and three full baths, with Spectacular Ocean view from most every room, complemented by a charming separate cottage with its own bedroom, bathroom, and full kitchen ideal for guest!Step outside to a sparkling chill/heated swimming pool where you can sip your morning coffee or evening cocktail while overlooking endless ocean views and the natural coastal wildlife. It's exclusive , it's unique and it's a true gem!. It's The Kind Of Oceanfront setting with a True Resort-Like Feel Everyday!.

75433 Overseas Hwy, Islamorada
$3,999,000
3 Beds ⋅ 4 Baths ⋅ 616917 MLS
Introducing The Twins on Olivia - a storied Key West treasure reborn. Once known locally as ''Olivia's Twins'' and documented on the 1892 Sanborn maps, this historic Old Town property has been meticulously reimagined and rebuilt to perfection after once being condemned by the City of Key West. Today, it stands proudly renewed - a testament to timeless design, craftsmanship and the enduring charm of Key West architecture. Perfectly located on coveted Olivia St. in the Heart of Old Town, this residence enjoys a 10 out of 10 walkability score, offering effortless access to Key West's most beloved restaurants, galleries and historic attractions. Crafted by Kanga Construction, this architectural masterpiece blends historic inspiration with the finest modern finishes. The home features impact-rated windows and doors, including a striking custom mahogany front door, complemented by a mahogany entrance way & lattice detailing that echo the island's craftsmanship heritage. Inside, French oak flooring flows throughout open sun -filled living spaces. The designer kitchen features Viking appliances, gas stove, ice maker, Hansel & Bringle custom cabinetry & luxurious quartz countertops. Two distinct staircases pay homage to the original twin structures, offering privacy & architectural intrigue. Each bedroom suite boasts an ensuite bath & build in closets, with dual-zone air conditioning and dual whole house dehumidifiers ensuring year round comfort. Thoughtful details abound - plantation shutters, a curated furniture package by local designer David Smith & masterful finishes throughout. Outdoors, a heated pool with tranquil waterfall is framed by tropical landscaping that provides privacy while off street parking adds convenience. Meticulously executed in both form and function, The Twins on Olivia represents one of the most exceptional new builds to grace the Old Town Market in Years - a home honoring it's history while defining modern Key West luxury.

1010 Olivia St, Key West
$3,995,900
5 Beds ⋅ 6 Baths ⋅ 616700 MLS
Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West. Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10' ceilings, impact glass, and abundant natural light. The chef's kitchen includes premium appliances, quartz countertops, pantry, and large island ideal for entertaining. Multiple verandas, balconies, and a rooftop observation deck deliver 360-degree sunrise and sunset views. Outdoors, enjoy your own sparkling infinity pool, expansive pool deck, and seamless flow to the water. Every residence conveys with an assigned dock space in a private boat basin featuring new composite docks with electric, water, and a fillet station--perfect for boating enthusiasts. Homes are equipped with Tesla Solar, an elevator, and generous storage. Resort-style amenities include a sport court for tennis, pickleball, and basketball, along with oceanfront lounge areas, hammocks, and opportunities for paddleboarding and kayaking. Just one block from a private airport, accessibility is unmatched. For investors, Seven Palms Cove is an exceptional opportunity: there are no rental restrictions, and nearby comparable properties generate over $300,000 annually. Whether as a forever home, luxury vacation retreat, or high-performing investment, Seven Palms Cove offers the perfect blend of exclusivity, comfort, and opportunity in the Florida Keys.

231 E Shore Dr Unit 1, Summerland
$3,995,000
5 Beds ⋅ 4 Baths ⋅ 620430 MLS
Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vacation rental history. Situated on 1.82 private acres with approximately 225 feet of ocean frontage, this Residential Estate-zoned property is currently licensed for legal 7-day vacation rentals, making it one of the limited number of properties within the Village of Islamorada offering this highly sought-after privilege. With a documented history as a successful income-producing vacation rental, this property offers the opportunity to enjoy an extraordinary Florida Keys lifestyle while rental income may help offset the costs of ownership. A gated entrance welcomes you through a majestic Royal Palm-lined circular driveway to an impressive, covered portico. Inside, a dramatic foyer and elegant wrought-iron staircase set the tone for a home featuring five spacious bedrooms, four beautifully appointed bathrooms, and breathtaking ocean views throughout. Enjoy spectacular sunrises from the observation pier or relax year-round in the heated and chilled saltwater pool. The home is beautifully appointed with quartz countertops, premium appliances, impact-resistant windows, and exceptional craftsmanship throughout. Whether you're seeking a luxurious private residence or a proven income-producing property to help offset costs, this ideal combination of both is a remarkable Islamorada estate that offers an exceptional blend of privacy, oceanfront beauty, and one of the most desirable licensed weekly vacation rental opportunities in the Florida Keys.

87445 Old Hwy, Islamorada
$3,995,000
5 Beds ⋅ 3 Baths ⋅ 618653 MLS
Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence designed for relaxed coastal living and effortless entertaining. The home offers 5 bedrooms and 3 bathrooms, with approximately 2,640 square feet of living space, including 3 bedrooms and 2 bathrooms upstairs totaling approximately 1,500 square feet, and 2 bedrooms and 1 bathroom downstairs totaling approximately 1,140 square feet. The private resort-style backyard features a heated pool with sun shelf, hot tub, expansive patio, hammock lounge, and mature palms creating a true tropical setting. Enjoy deep-water canal frontage with 70 feet of dockage and two boat lifts rated at approximately 15,000 pounds and 20,000 pounds, providing exceptional boating capacity. Located on one of Venetian Shores' desirable 100-foot-wide canals, the property offers generous maneuvering space and convenient access to both the Atlantic Ocean and Florida Bay through nearby Snake Creek, making offshore fishing and backcountry boating easily accessible within minutes. The custom tiki pavilion includes a full outdoor kitchen with built-in grill, refrigeration, sink, bar seating, mounted TV, and generous space for hosting gatherings year-round. Inside, the bright open-concept living area showcases vaulted ceilings with exposed beams, abundant natural light, and French doors that create seamless indoor-outdoor flow to the balcony overlooking the canal. The primary suite offers balcony access, dual vanities, soaking tub, glass-enclosed shower, and walk-in closet. A gated brick driveway provides generous parking, and the home is offered furnished for immediate enjoyment or continued use as a full-time residence, seasonal escape, or investment opportunity. This Venetian Shores waterfront property delivers the location, spacious layout, wide canal setting, and boating infrastructure buyers are searching for in the Florida Keys.

105 Palo De Oro Dr, Islamorada
$3,995,000
4 Beds ⋅ 4 Baths ⋅ 615642 MLS
This resort-style oceanfront home is the perfect vacation home or primary residence, offering unparalleled views of the Atlantic Ocean along with a heated pool and hot tub, beach area with wood fire pit, propane tiki torches, pavilion, and deep water dockage with a boat lift. The spacious interior features 4 bedrooms and 4 bathrooms across three levels. The main living area on the second floor includes high wood ceilings, panoramic ocean views, an oceanfront balcony, and a bedroom with an adjacent bathroom. The third floor is dedicated to the primary suite, complete with a private balcony for a bird's-eye view. The ground level includes two additional bedrooms with en-suites and a large laundry room. Additional highlights include a garage for boating and dive gear, gated entry, paver driveway, and parking for multiple vehicles. Located at mile marker 95 in Key Largo, enjoy world-class fishing and diving right from your backyard.

802 Bonito Ln, Key Largo
$3,995,000
5 Beds ⋅ 5 Baths ⋅ 618011 MLS
Stunning New Three-Story Bay View Residence. This Light-Filled 5-Bdrm, 4.5-Ba enjoys nightly sunset views. State-Of-The-Art Kitchen & Luxurious Finishes Throughout. 3 Generously sized ensuites, walk-In closets, and lavish bathrooms. Expansive Roof Top Terrace with wet bar and kitchen. Step into an open living area that effortlessly flows to the entertainment area and chef's kitchen. Enjoy indoor-outdoor living with multiple balconies, a waterfront roof top terrace complete with a built-in bar and summer kitchen, and direct access to a half bath. The home is designed for entertaining while capturing spectacular sunsets year-round. For those who cherish the outdoor allure of the Keys, the concrete dockage with deep water direct access beckons. Your personal gateway to the crystal-clear waters, embark on boating adventures, fishing expeditions, or diving explorations right from your doorstep. This home caters to the water enthusiast, offering a privileged lifestyle. A pool and elevator to all floors. In every aspect, this modern haven is a celebration. A harmonious fusion of luxury, nature, and waterfront living. This is more than a home; it's an invitation to savor life's most indulgent moments against the backdrop of stunning sunsets and the allure of the open water. Your waterfront paradise awaits - where every day feels like a vacation, and every sunset is a masterpiece. Welcome home to the epitome of coastal living in Key Largo. Gated property with covered parking. This home is a boater's dream and delivers both beauty and peace of mind. Offered turn-key and Available for Your Immediate Enjoyment! Seller Financing Available.

141 Grassy Rd, Key Largo
$3,988,999
5 Beds ⋅ 3 Baths ⋅ 619474 MLS
Experience unparalleled luxury and waterfront living in this stunning modern home, built in 2020 and situated on a corner lot with over 200 feet of waterfront property. *Contemporary Masterpiece* This all-CBS home boasts sleek, contemporary finishes throughout its four stories, including a gourmet chef's kitchen with a breathtaking quartz waterfall island. The interior design seamlessly blends style and functionality, perfect for entertaining and everyday living. *Rooftop Oasis* Take in the stunning views from the newly turfed rooftop, accessible via a dramatic spiral staircase. The perfect spot to relax and enjoy the surroundings. *Outdoor Paradise* The expansive outdoor space features a full outdoor kitchen downstairs, ideal for alfresco dining and entertaining. The property also includes an 80-foot composite dock with a 20,000 LB Neptune boat lift and an additional 125 feet of seawall on the main canal. Approved pool plans are available for those looking to add an extra layer of luxury. *Direct Bay and Ocean Access* Enjoy direct access to the bay and ocean through Jewfish Creek or Adams Cut, making this property a boater's paradise. *Additional Features* - Mosquito misting system for ultimate comfort - Residential elevator for effortless navigation between floors - Sold fully furnished (except master bedroom furniture) *A Rare Opportunity* Don't miss the chance to own this extraordinary waterfront estate in Key Largo. With its stunning design, expansive outdoor spaces, and unparalleled water access, this property is a true gem. Schedule a private viewing today!

475 Bahia Honda Rd, Key Largo
$3,950,000
5 Beds ⋅ 5 Baths ⋅ 619766 MLS
Stunning brand-new custom modern home with just the right amount of Keys flair, where no detail was overlooked from design to layout to finishes. Enter through a private electric gate onto this beautifully positioned corner lot, featuring covered parking, a lavish pool and hot tub, and a fully equipped outdoor kitchen, all surrounded by pristine, thoughtfully designed landscaping. A grand foyer welcomes you in, complete with a private elevator providing seamless access to every level. Designed with entertaining in mind, the home offers expansive living and dining spaces anchored by a gourmet kitchen, all flowing effortlessly into the outdoor areas to create the ultimate indoor-outdoor lifestyle. Boat lift included in the sale! The primary suite is a true retreat, featuring a spacious private balcony, a luxurious spa-style bathroom with soaking tub and separate shower, and a large walk-in closet. Four additional bedrooms, each with their own ensuite bathrooms, carry the same high level of craftsmanship and attention to detail throughout. Crowning the home is a rooftop deck with amazing ocean views, perfect for entertaining guests or enjoying a quiet, romantic evening. Come experience the quality, design, and thoughtfulness of this exceptional home for yourself.

301 Buttonwood Cir Unit B, Key Largo
$3,950,000
4 Beds ⋅ 4 Baths ⋅ 618942 MLS
New 2025 waterfront construction on the final canal in Key Haven--an architectural entertainer designed for seamless indoor-outdoor living just 5 minutes from Key West. Unlike typical Keys homes, this residence was designed around outdoor living, offering over 2,400 Sq.Ft. of covered entertaining space seamlessly connected to the interior. Completed in 2025, this striking modern waterfront residence offers 4 bedrooms + office, 4 bathrooms, and 2,458 Sq.Ft. of interior living space. Positioned on the coveted final canal in the exclusive Key Haven community, the home is designed for privacy, entertaining, and exceptional boating access. The layout offers rare flexibility. The entire top level functions as a private guest quarters, ideal as an elevated primary suite, luxury guest retreat, or in-law residence with some of the best water views in the home. This level also features a large covered porch spanning the entire floor, creating an additional private entertaining space. Inside, the architecture emphasizes volume, light, and clean modern lines. Tall ceilings, expansive glass, and large polished porcelain tile flooring create a refined coastal aesthetic. The open living area centers around a gourmet kitchen with Thermador appliances designed for entertaining. Stackable glass doors open the entire main living space onto a wide covered waterfront porch, for seamless indoor-outdoor living. A private elevator with access from ground level.Outdoor spaces include four decks, a rooftop deck with sweeping water views, a pool with swim-up bar, and a private putting green. The rooftop deck is ideal for spectacular sunsets and stargazing. For boating enthusiasts, the property features a 15,000 lb boat lift and davit with quick access to both the Gulf and Atlantic. Additional highlights include solid concrete construction, standing seam metal roof, elevator access, high-end finishes, and a large air-conditioned storage room. Photos include virtually staged furniture.

3 Evergreen Ave, Key Haven
$3,950,000
4 Beds ⋅ 5 Baths ⋅ 618400 MLS
The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 14, Islamorada
$3,900,000
620460 MLS
A truly once in a generation opportunity to build your dream estate in the heart of Islamorada's coveted Lower Matecumbe. This exceptional vacant homesite is one of the few remaining parcels of its size available in all of Islamorada, offering an incredibly rare combination of breathtaking ocean views and expansive wide canal views. Encompassing over 32,000 square feet, this extraordinary property provides the perfect canvas for a custom waterfront residence designed to capture spectacular sunrises, refreshing ocean breezes, and the unmatched beauty of the Florida Keys. Its unique setting offers the best of both worlds--open water vistas in the front and a wide canal in the rear, creating an unparalleled lifestyle for boating enthusiasts and those seeking privacy, space, and unforgettable scenery. Opportunities to acquire a property of this caliber have become increasingly scarce in Islamorada, where large vacant parcels are exceptionally limited. Whether you're envisioning a private family compound or a legacy waterfront estate, this one-of-a-kind offering represents a chance to create something truly extraordinary in one of the Florida Keys' most desirable destinations.

74900 Overseas Hwy, Islamorada
$3,900,000
4 Beds ⋅ 5 Baths ⋅ 620305 MLS
Rare Florida Keys mixed-use development opportunity with approx. 124,300 sq. ft. of uplands plus additional bay bottom ownership. Property includes 4 verified building rights with Letter of Site Condition on file. Existing improvements include a duplex and single-family home. Mixed Use (MU) zoning allows for a wide range of future possibilities, including commercial, residential, storage facility, marina-related use, workforce housing, market-rate housing, or potential subdivision into multiple parcels. Current zoning allows up to 6 market-rate units per acre or up to 15 affordable units per acre, buyer to verify per City of Marathon. The property offers approximately 216 feet of highway frontage, plus additional east-side access through an access easement, creating multiple entry points and flexibility for future site planning. A neighboring gas station adds convenience and commercial synergy for future development concepts. A unique feature is the sleeper asset of this property which is ownership/control of bay bottom extending behind approximately 12 lots along Cocoplum Drive, creating potential value tied to dockage, marina concepts, water access, assemblage opportunities, or long-term redevelopment. Deep-water access, good depth, multiple boating configurations, and proximity to the marked channel entrance add to the site's appeal. Large mixed-use tracts with water access and verified building rights are increasingly rare in the Florida Keys, making this a strong opportunity for an investor, developer, marina operator, or long-term land holder. Seller states property will be delivered vacant and free of personal belongings before closing. Buyer to verify zoning, density, building rights, permitted uses, dockage, water depth, access easements, permitting, and development potential.

13759 Overseas Hwy, Marathon
$3,900,000
3 Beds ⋅ 3 Baths ⋅ 619454 MLS
Welcome to Casa Tranquila in the highly desirable Venetian Shores neighborhood of Islamorada, where boating convenience meets tropical serenity. With 105 feet of dockage just one home from Snake Creek, this property offers immediate access to both the bay and the ocean--perfect for effortless days on the water. A brick-pavered driveway leads to a welcoming foyer and interior staircase, guiding you to the light-filled main living level. Here, an open floor plan creates an inviting space for gathering. The well-appointed kitchen features stainless steel appliances and flows effortlessly into the dining and living areas, making entertaining both easy and enjoyable. Just off the dining space, a convenient dry bar provides the perfect spot for preparing cocktails and serving guests. Two sets of sliding glass doors extend the living area onto a spacious screened terrace--ideal for enjoying breezes and waterfront views. This level also offers two comfortable bedrooms, two full baths, and a dedicated laundry room for added convenience. The private third-floor primary suite is a true retreat, complete with an ensuite bath and an expansive open terrace overlooking the water--your own peaceful escape for sunrise coffee or evening relaxation. Surrounded by lush, mature landscaping--including ponytail palms, queen palms, ginger, and fishtail palms--the property feels like a secluded tropical oasis. The backyard is designed for both relaxation and entertaining, featuring a heated saltwater pool with spa and waterfall, a charming tiki hut with lighting and fan, and fruit-bearing key lime and mango trees that enhance the island ambiance. With its prime location, thoughtful layout, and beautifully curated indoor and outdoor spaces, this home captures the essence of the Islamorada lifestyle--elegant, inviting, and effortlessly connected to the water.

131 Bayview Isle Dr, Islamorada
$3,900,000
4 Beds ⋅ 5 Baths ⋅ 618319 MLS
Welcome to ''The Lookout', a premiere four-bedroom oceanfront residence within Playa Largo Ocean Residences, a purpose-built luxury waterfront enclave in the heart of Key Largo. Centrally located to all that Key Largo has to offer, yet discreetly set within a private, gated community, this residence offers a rare balance of accessibility and seclusion. Built to the highest structural standards to withstand coastal conditions, the home reflects a commitment to longevity, performance, and refined design. The residence is offered fully furnished with a designer-grade interior package, delivering a cohesive, turnkey experience. Clean architectural lines, premium materials, and thoughtfully curated interiors define the living spaces, while expansive ocean-facing terraces extend the home's livability outdoors. Open-concept living and dining areas are designed for both everyday use and entertaining, with each bedroom suite offering privacy and comfort. Owners enjoy exclusive access to a private clubhouse, resort-style pool, and landscaped grounds. Directly across the street, Playa Largo Resort & Spa, Autograph Collection provides full access to world-class dining, spa services, beach amenities, and water-based activities, enhancing both lifestyle and rental appeal. The community is intentionally limited in scale, preserving a residential atmosphere while benefiting from resort infrastructure just moments away. A defining attribute of this offering is the flexibility of ownership and rental strategy. New owners may elect to participate in the Playa rental management program with full resort privileges or self-manage and rent independently, providing uncommon control over use and income. With nightly rentals permitted, this premier oceanfront residence is equally suited as a refined weekend retreat, a rental income opportunity, or a long-term hold in one of the Florida Keys' most established resort communities. Quiet, secure, and impeccably positioned.

48 E Playa Largo Blvd, Key Largo
$3,899,000
4 Beds ⋅ 2 Baths ⋅ 620235 MLS
Rarely does a Florida Keys property offer the combination of proven vacation rental income, transient rental zoning, private beachfront, and future development flexibility found at the historic Long Key Fish Camp. Situated at the southern tip of Long Key, this income-producing oceanfront property boasts 221 feet of private white sand beach, unobstructed Atlantic Ocean views, and both sunrise and sunset. Currently operating as a successful nightly vacation rental, the property offers a rare opportunity for investors seeking immediate income with the flexibility to further enhance or redevelop the site. The existing legal duplex features four bedrooms and two bathrooms, capturing the character and charm of Old Florida Keys living. Continue operating the property as a vacation rental, renovate the existing improvements, or explore the property's long-term redevelopment potential. The offering includes two development rights associated with the legal duplex, plus a third development right for an accessory structure, an increasingly rare asset in the Florida Keys. This unique combination creates opportunities to maximize rental income, establish a private waterfront compound, or pursue future redevelopment, subject to applicable approvals. Ideally positioned between Islamorada and Marathon, the property offers convenient access to marinas, restaurants, shopping, and airports while maintaining a level of privacy rarely found in the Keys. The shallow turquoise waters offshore are ideal for kayaking, paddleboarding, snorkeling, and fishing, while nearby Long Key State Park and the Long Key Viaduct provide access to some of the world's most renowned tarpon fishing. Adding to its significance, the property occupies the former site of Henry Flagler's original Long Key Fishing Camp. In the early 1900s, famed author Zane Grey helped establish Long Key as one of sportfishing's most celebrated destinations, hosting notable guests including Herbert Hoover and Franklin Rooseve

65620 Overseas Hwy, Long Key
$3,899,000
4 Beds ⋅ 2 Baths ⋅ 616369 MLS
Rarely does a Florida Keys property offer the combination of proven vacation rental income, transient rental zoning, private beachfront, and future development flexibility found at the historic Long Key Fish Camp. Situated at the southern tip of Long Key, this income-producing oceanfront property boasts 221 feet of private white sand beach, unobstructed Atlantic Ocean views, and both sunrise and sunset. Currently operating as a successful nightly vacation rental, the property offers a rare opportunity for investors seeking immediate income with the flexibility to further enhance or redevelop the site. The existing legal duplex features four bedrooms and two bathrooms, capturing the character and charm of Old Florida Keys living. Continue operating the property as a vacation rental, renovate the existing improvements, or explore the property's long-term redevelopment potential. The offering includes two development rights associated with the legal duplex, plus a third development right for an accessory structure, an increasingly rare asset in the Florida Keys. This unique combination creates opportunities to maximize rental income, establish a private waterfront compound, or pursue future redevelopment, subject to applicable approvals. Ideally positioned between Islamorada and Marathon, the property offers convenient access to marinas, restaurants, shopping, and airports while maintaining a level of privacy rarely found in the Keys. The shallow turquoise waters offshore are ideal for kayaking, paddleboarding, snorkeling, and fishing, while nearby Long Key State Park and the Long Key Viaduct provide access to some of the world's most renowned tarpon fishing. Adding to its significance, the property occupies the former site of Henry Flagler's original Long Key Fishing Camp. In the early 1900s, famed author Zane Grey helped establish Long Key as one of sportfishing's most celebrated destinations, hosting notable guests including Herbert Hoover and Franklin Rooseve

65620 Overseas Hwy, Long Key
$3,899,000
3 Beds ⋅ 3 Baths ⋅ 618713 MLS
Positioned on a rare west facing point lot with 270 ft of sparkling open water frontage on Sugarloaf Sound, this fully reimagined 3 Bedroom 3 Bathroom estate captures breathtaking sunset views across endless turquoise waters. Privately set on a gated 17,000 SF lot, the property lives like a private island compound framed by swaying palms, lush tropical landscaping, and the endless blue waters of the sound. The CBS constructed residence is complemented by a new aluminum standing seam metal roof and a complete set of impact windows/doors, offering exceptional structural integrity paired with refined island sophistication. Walls of glass flood the expansive open concept living area with natural light and showcase panoramic water views from nearly every vantage point, immersing the home in its spectacular waterfront setting. The coastal modern interior features tile plank flooring throughout, clean architectural lines, and a serene coastal palette that reflects its tropical surroundings. The chef's kitchen is anchored by an oversized waterfall edge island, custom cabinetry, high end stainless appliances, wine refrigeration, and designer lighting, all positioned to embrace the open water backdrop. The spacious primary suite overlooks the sound and serves as a private retreat, featuring a spa inspired bath with dual vanities, custom tile work, and a frameless glass walk in shower. Two additional ensuite guest bedrooms are beautifully appointed, offering privacy and comfort for family and visitors. Outdoors, the brand new concrete pool and inviting tiki hut create a true resort style setting, complemented by expansive lawn space rarely found in the Keys. After a day of world class fishing and diving in the Lower Keys, dock your vessel on the 14,000 lb boat lift, an exceptional enhancement to the waterfront lifestyle. Completely renovated and move in ready, this extraordinary estate defines sophisticated island living at its finest.

17015 W Wahoo Ln, Sugarloaf
$3,875,000
4 Beds ⋅ 3 Baths ⋅ 620412 MLS
Coastal elegance meets the ultimate boating lifestyle in this beautifully updated Venetian Shores home. Designed for effortless Keys living, the open floor plan is filled with natural light, highlighted by a dramatic floor-to-ceiling wall of windows in the living area that brings the outdoors in. An inviting entrance foyer welcomes you inside, with interior stairs to the main living level. The spacious kitchen is the heart of the home, featuring stainless steel appliances, a large island for gathering, and a separate laundry room and pantry for added convenience. The main living level offers two guest bedrooms and two full baths, including one bedroom with a private en-suite bath. Direct access from the second-floor living area to the pool deck creates a seamless connection between indoor and outdoor living. The open floor plan offers plenty of room for dining, watching TV, conversation and even some ping pong. Upstairs, the expansive primary suite provides a peaceful retreat with a walk-in closet and luxurious en-suite bath. A fourth bedroom on the third floor offers flexibility for guests, family, or a home office. Separate air-conditioning systems for each floor ensure year-round comfort. Outside, 70 feet of dockage and a 27,000-pound boat lift make this property a dream for boating enthusiasts, with quick access to both the Atlantic Ocean and Florida Bay. The resort-style backyard is ready for endless summer fun, featuring a sparkling pool, expansive sun deck, shady lounging area, and abundant storage for all your fishing, diving, and water sports gear. Whether you're entertaining friends, heading out for a day on the water, or simply relaxing poolside, this exceptional Venetian Shores home offers the perfect blend of coastal sophistication and waterfront adventure.

109 Giardino Dr, Islamorada
$3,850,000
4 Beds ⋅ 4 Baths ⋅ 620893 MLS
Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing property is being sold fully furnished, allowing the new owner to seamlessly continue operating it as a successful vacation rental from day one or immediately begin enjoying it as a private island retreat. Designed with flexibility in mind, this two-story home features a total of 4 bedrooms, 4 bathrooms, and two full kitchens. The upper level offers 3 bedrooms, 2 bathrooms, a full kitchen, and a private balcony, while the lower level includes 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen, making it ideal for guests, multi-generational living, or maximizing short term rental income.Step outside to your private pool, then take just a few steps to your own private beach, creating the ultimate island experience. A new A/C system and metal roof also adds comfort and peace of mind. Conveniently located just minutes from Robbie's Marina and Theater of the Sea, you'll enjoy world class fishing, boating, snorkeling, waterfront dining, and everything that makes Islamorada one of the premier destinations in the Florida Keys.

74049 Overseas Hwy, Islamorada
$3,800,000
3 Beds ⋅ 3 Baths ⋅ 620343 MLS
First time offered in more than 25 years, this beloved Old Town address presents a rare opportunity to own a complete compound on one of Key West's most private and premier streets. Located in the desirable X flood zone, the property features three bedrooms, three baths, and off-street parking for two vehicles. Rich in character and timeless Key West architecture, the home showcases beautifully white-painted, Dade County pine floors and walls, crown molding, and an open-concept living space. Dramatic cathedral ceilings in the living and dining areas create an airy, expansive atmosphere filled with natural light. The main residence offers excellent storage with multiple closets, two spacious bedrooms each with a private en-suite bath, a dedicated library/office, and a separate utility room. True to classic indoor-outdoor island living, French doors open from nearly every room, leading to a private oasis designed for entertaining. The backyard features a private 26' x 11' heated pool accented by dual waterfalls, a gas fire pit, an outdoor shower, and an expansive patio surrounded by lush landscaping. Enjoy the large, comfortable covered porch, perfect for enjoying coffee and the morning paper or an afternoon nap. Guests will be delighted to stay in the detached cottage with ample closet space and a beautifully appointed bath finished with floor-to-ceiling glass tile. Thoughtfully designed, the bath offers dual access--one entrance from the bedroom and another directly from the patio--making it an ideal pool bath. Adding to the property's charm is a lighted turf area with an added surprise, perfect for large parties and room for the kids or pets to play. Relax on the front porch, currently separated from the back porch by a privacy wall. With a small extension, the home's original wraparound design can be fully restored. This extraordinary opportunity to own a classic period home in the heart of Old Town is not to be missed. Call today to schedule your private showing.

619 Ashe St, Key West