luxury houses with pool for sale Summerland Key, United States

Welcome to one of Cudjoe Gardens' most desirable waterfront addresses Built in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3 bathrooms, and more than 2,400 square feet of thoughtfully designed living space. Perfectly positioned on an oversized waterfront lot, this home combines outstanding boating amenities, resort-style outdoor living, and remarkably affordable insurance costs. One of the property's most impressive features is its combined flood, wind, and homeowners insurance, totaling less than $5,500 per year--an extraordinary value for a waterfront home of this caliber in the Florida Keys. Designed with boaters in mind, the property offers approximately 100 feet of concrete dockage along a wide flow-through canal with deep-water access and quick routes to both the Gulf of Mexico and Atlantic Ocean. Two boat lifts, including a 10,000-pound and 14,000-pound lift, provide ample capacity for multiple vessels, making it easy to keep your boats protected and ready for your next fishing, diving, or boating adventure.The backyard is a private tropical retreat centered around a stunning 50-foot resort-style swimming pool heated/chilled Whether you're swimming laps, entertaining guests, or simply relaxing in the Florida sunshine, this outdoor space was designed to impress. A custom tiki bar, outdoor kitchen, waterfront pergola, and expansive entertaining decks create the perfect setting for hosting family and friends while enjoying beautiful waterfront views. Inside, the open-concept floor plan is filled with natural light and designed to capture water views throughout the home. High ceilings, spacious living areas, and modern coastal finishes create an atmosphere that is both elegant and comfortable. The seamless transition between indoor and outdoor living makes this home ideal for embracing the laid-back Florida Keys lifestyle.Located within the sought-after Cudjoe Gardens community, and nearby marina

This is set to become one of the most striking homes on Shark Key and it's already underway. A rare opportunity to own a completely brand new waterfront home in one of the Florida Keys' most exclusive gated communities. Positioned on Sea Lore Lane, this 18,750 sq ft waterfront lot offers more than 90 feet of pristine shoreline and uninterrupted open water views. Designed by Artibus Design, the residence is currently under construction and envisioned as a nearly 6,000 sq ft modern coastal showpiece with 6 bedrooms and 6.5 bathrooms. Every inch of this home is being thoughtfully built for modern waterfront living, combining bold architecture, expansive walls of glass, elevated finishes, and seamless indoor outdoor flow throughout. This is the appeal of brand new construction in the Keys. Fresh design. Modern materials. Current building standards. A home created for the way buyers want to live today. Inside, expansive open living spaces, gallery style proportions, striking focal points, an indoor gym, and a large entertainment room create a setting that feels both sophisticated and inviting. Outside, a resort style waterfront environment takes center stage with a pool, expansive covered outdoor living spaces, and a large three car garage beneath the home, all designed to maximize the incredible setting and open water views. For a limited time, a buyer has the rare opportunity to step in and customize finishes and details, helping shape the final vision while avoiding the years of planning, approvals, and uncertainty that can come with building in the Florida Keys. With construction already in progress, this is an opportunity to secure one of the most exciting new builds coming to Shark Key before completion. This is more than new construction. It's the opportunity to own one of the island's most exciting new waterfront homes and create something truly exceptional in the Florida Keys.

Where the essence of the Florida Keys meets refined coastal luxury, 94 Driftwood Drive stands as a rare bayfront sanctuary in coveted Key Haven. Just minutes from the energy and culture of Key West, this residence offers a lifestyle defined by serenity, sophistication, and seamless access to world-class cuisine and adventure. Framed by spectacular water views from every room, the home's architecture embraces its setting with an effortless elegance. A mesmerizing infinity-edge pool and spa appear to merge with the open sea, creating a private resort experience at the water's edge. Inside, the striking chef's kitchen commands attention with state-of-the-art appliances and a dramatic solid-walnut entertainment island--an exquisite centerpiece for gatherings both intimate and grand. Offering 5 bedrooms and 5.5 baths, including primary suites on both levels, the residence is designed for comfort, privacy, and elevated living. Hardwood floors, impact-glass windows, and an oversized 2-car garage with direct dock access and room for a boat trailer reflect thoughtful craftsmanship throughout. Flexible spaces accommodate a gym, studio, or entertainment room, while a meticulously organized storage area supports both home and pool systems with precision. For the boating and water-sport enthusiast, a dedicated equipment room provides direct access to the oceanfront dock and boat lift, placing the Keys' endless waterways at your doorstep. A custom iron staircase rising from the first to the third floor serves as a sculptural showpiece, its ocean-inspired artistry echoing the home's coastal surroundings. 94 Driftwood Drive is more than a residence--it is a statement of lifestyle, where tranquility and sophistication meet the unmistakable allure of the Florida Keys.

Escape to ''The Castle'', a luxurious gated Gulf-front estate rarely spanning 1.14 acres on Big Pine Key. This extraordinary retreat is a graceful blend of architectural grandeur and coastal charm, thoughtfully designed for both relaxation and recreation. Boaters will delight in an unparalleled offering of 235 feet of dockage total: 140 feet of protected canal-front dockage featuring a 15,000 lb lift, cut-in slip, boat ramp, plus a 95-foot open water pier-style dock with additional 15,000 lb lift and cut-in slip, set against a 130-foot concrete seawall for secure, convenient access. Crafted in 2014 with solid poured concrete, impact-rated windows and doors, whole home generator and elevator, the home is built for enduring elegance. With over 4,600 square feet of refined interior space, this 3-bedroom, 3-bathroom estate is an architect's masterpiece with its stately presence, curved openings, and striking double staircase. Step inside to a breathtaking panorama of endless open Gulf waters and nightly sunset performances. The chef's kitchen is a dream for entertaining, featuring 10.5-foot island with seating for 8, dual sinks, refrigerators, and ovens, plus Jenn-Air 6-burner gas cooktop with pot filler, and rich wood cabinetry. Enjoy the grand family room with Gulf views, host movie nights in the private theater, or dine al-fresco under the stars. Nearby, find the full-size laundry room and storage. The top-floor primary suite is a sanctuary, offering sweeping water views, home office, private lounge with kitchenette, spa-like bath with clawfoot tub, tiled shower and generous walk-in closet with additional laundry. Outside, the resort-style pool beckons with a spa, water features, LED lighting, plus heater and chiller. Rooftop deck with 180-degree views, and unrivaled sunsets await. Offered fully furnished, this is ultimate Keys living without compromise!

Step inside your perfect Key West condo! This 2 bedroom and 2 full bathroom condo offers the best of Key West living! A split bedroom floor plan makes this ideal for guests or multi family living. The balcony offers peaceful views of the Salt Ponds and a great space to relax. The wonderfully maintained grounds offer a newly renovated swimming pool, a tennis court and BBQ area. Smathers Beach is just a short bike ride / walk away and the path offers a great spot for morning walks by the ocean. Your own private covered parking bay affords quick access to the elevator. Call for your private showing and make this your Key West home today!

Open water pool home with breathtaking views of Bogie Channel and direct deep water access to both the Atlantic Ocean and the Gulf. Located on a spacious 13,275 sq ft lot, this solid concrete ground-level residence is a true boater's paradise featuring a 75-foot concrete dock and a protected boat basin. Inside, the 1,980 sq ft home offers a large great room, a Florida Room perfect for sunrise coffee, and a spacious kitchen with quartz countertops and a center island ideal for entertaining. Enjoy the seamless indoor-outdoor lifestyle with a waterfront pool surrounded by tropical landscaping, swaying palms, and a peaceful outdoor patio. The primary suite offers views of the pool and water, blending luxury and tranquility. Built to last with impact-resistant doors and windows and a durable metal roof. Additional features include a one-car garage, beautifully manicured grounds, and regular visits from native birds and Key Deer. Ride your bike across the bridge to No Name Key or walk to the world-famous No Name Pub. Just minutes to shopping, dining, and all the Lower Keys have to offer.

Brand-New Waterfront Home - Completed and Move-In Ready. This elevated CBS single-level residence offers 4 bedrooms, 3 bathrooms, 10-foot ceilings, impact-rated windows and doors, metal roof, stainless steel appliances, quartz countertops, open-concept living, screened porch, private pool, and covered parking below. Built for coastal living, the CBS structure, impact openings, elevated design, and metal roof provide durability, strength, and insurance-friendly features. Allocated dockage includes an approx. 45' access walk to a 91' platform, creating a great setup for boating, kayaking, paddleboarding, and waterfront views. Set on a 14,680-square-foot lot with approx. 75' of waterfront frontage, the property captures panoramic Bay/Gulf-front water views and sunrise exposure. Enjoy access via Bogie Channel, with backcountry access and fast open-water routes to the Atlantic Ocean and the Gulf. Nearby Looe Key Reef is a favorite for snorkeling and scuba diving. Located on the Big Pine Key side of the Bogie Channel Bridge to No Name Key, this setting offers water views and island privacy. The property can be used as an investment property for vacation rental use, adding flexibility and income appeal. Near the iconic No Name Pub and surrounded by the natural beauty of Big Pine Key, where Key Deer are part of everyday island life. Big Pine Key offers conveniences nearby, while still delivering a quiet waterfront lifestyle. Construction is complete and ready for immediate occupancy.

Sweeping Gulf views. Private deeded boat dockage. Effortless Key West elegance. Situated in the coveted enclave of Flagler's Landing, this elevated waterfront residence captures breathtaking open-water views from virtually every room--offering a front-row seat to world-famous Key West sunsets. Spanning ~1,387 sq. ft. of light-filled living space, the home is thoughtfully designed for effortless entertaining. The main level features an open-concept layout anchored by a gourmet kitchen, complete with a custom coral stone island (seating for six), custom cabinetry, under-cabinet lighting, premium GE appliances, a six-burner range, and a brand-new refrigerator. Warm bamboo flooring, recessed lighting, and a wide waterfront balcony create seamless indoor-outdoor flow for evening breezes and sunset entertaining. A half bath completes the main level. A spiral staircase leads to the upper level, where a built-in bookshelf hall opens to a front-facing balcony. Both serene bedrooms feature walk-in closets and expansive water views. The primary and guest suites share a spacious full bath equipped with a glass walk-in shower, large vanity, and a jacuzzi-style tub. Outside and below, additional amenities include ground-level covered parking, dedicated storage, a laundry area, and a private ground-floor brick patio. For boating enthusiasts, the home includes a deeded shallow-draft slip suitable for a ~24 ft. boat, along with access to a community heated concrete pool. Situated moments from beaches, dining, shopping, and marinas, this home presents a rare opportunity to own a luxury retreat in an exclusive Key West community.

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. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors, exceptional craftsmanship, and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office seamlessly integrated into the custom kitchen, the residence is designed for everyday comfort and grand-scale entertaining. The chef's kitchen centers around an oversized island with custom European-style cabinetry, premium quartz countertops, a BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar with refrigerator drawers, dishwasher, and built-in cabinetry. Travertine flooring, custom built-ins, 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, and HVAC. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, while a whole-house generator provides peace of mind. The luxurious primary suite offers a custom walk-in closet, and every bedroom has private balcony access. A guest suite includes a zero-entry shower for added comfort and accessibility. Tiled courtyards, expanded entertaining terraces, covered parking for four vehicles, an outdoor shower, and multiple laundry areas enhance daily living. Residents also enjoy an oceanfront pool overlooking the Atlantic, completing one of Key West's most distinctive waterfront residences.

Designed for relaxed island living, this modern home blends privacy, comfort, and convenience in Midtown, just minutes from dining, beaches, and nightlife. Clean lines, tall ceilings, and an abundance of natural light define the open-concept living spaces, while retractable impact glass doors invite seamless indoor-outdoor living. The updated kitchen pairs style with function, featuring quartz countertops, a tile backsplash, premium stainless-steel appliances, and open sightlines to the dining and living areasperfect for entertaining. The living space extends outdoors to a backyard retreat with a pool, generous lounge areas, and room for both sun-soaked afternoons and relaxed evening gatherings. The covered pool bar and adjacent half bath add thoughtful convenience for hosting. The primary suite is elevated and positioned in its own wing, offering a calm retreat with en suite bath, walk-in closet, and access to a private deck overlooking the pool. Two additional bedrooms are equally well-appointed, providing comfortable accommodations for family or guests. Built with durability and ease of maintenance in mind, the concrete construction includes a metal roof, impact doors and windows, security system, and a private gated driveway with two keypad entry gatesideal for full-time residents or seasonal use. For buyers seeking investment potential, the property already offers a strong rental history, with January through March secured at $41,500 and returning tenants eager to continue year after year. Bright, airy, and thoughtfully designed, this home captures the essence of relaxed modern living in one of Key West's premier neighborhoods.

Welcome to Casa Lanka in Key West! This unique property consists of a 4 bedroom 3.5 bath CBS home on a double lot with an abundance of mature tropical plants creating a private oasis. Tucked away from the main home, a separate cottage makes an ideal space for guests, extended family, or a private office. A sparkling pool anchors the outdoor living space, surrounded by mature tropical landscaping and a peaceful walking path that winds through the property. Additional features include a spacious carport accommodating up to four vehicles, a large airconditioned utility room and a large shed. This unique offering blends indoor and outdoor living, creating a peaceful island hideaway close to everything Key West has to offer. Seller is open to reviewing all offers!

Nestled on No Name Key, a small coastal island of just 43 homes, this exceptionally private pool home offers a serene island retreat with unparalleled Gulf views, modern design, & luxurious features. Situated at the end of the road abutting government land this lushly landscaped gated lot with full sprinkler system boasts water access on two sides. Its location in a designated wildlife refuge ensures complete tranquility, free from highway noise. Designed with an open-concept layout that integrates indoor & outdoor spaces, this home is perfect for entertaining. Expansive windows & screened-in porches on all three levels allow for beautiful open water views & natural sea breezes, keeping the home cool & connected to its surroundings. The open-concept kitchen, living, & dining area is designed for both relaxation & entertaining. The kitchen boasts stainless steel appliances, quartz countertops, double ovens plus a large peninsula for seating. The living room, complete with coral rock fireplace, opens to a screened-in porch via two sets of pocket sliding glass doors, offering panoramic water views. A den on the main floor includes a kitchenette, built-in cabinetry, and a private entrance with its own deck, making it ideal for use as an office, 3rd bedroom, or mother-in-law suite. Pocket sliding doors lead to a screened veranda and sun deck overlooking the pool. Upstairs, two ensuite bedrooms feature high ceilings and stunning sunset views over the Gulf. Both bedrooms open to private screened-in decks. The primary bedroom includes a fireplace, walk-in closet, and a luxurious bathroom. The second bedroom offers open water views and a private bath. A 3rd-story viewing area provides 360-degree panoramic water views. Catch tarpon in the basin from one of your two docks with full seawall & davits or relax by the heated salt pool surrounded by lush tropical landscaping. Two storage rooms for tools and gardening equipment complete this beautiful home!

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.

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.

Built in 2008, this stunning 3-bedroom, 3.5-bath pool home perfectly blends the timeless character of classic Key West architecture with the comfort and convenience of modern construction. Ideally located just a short stroll from shops, restaurants, bars, and the world-famous Duval Street, this home offers the best of island living. Step inside to a bright, open-concept main living space with a wall of stackable impact glass doors that seamlessly connect the indoors with the private outdoor oasis. Just beyond the doors, you'll find a custom heated pool with tranquil water fountains, surrounded by lush tropical landscaping that offers both beauty and privacy, all complemented by a brand-new travertine pool deck that enhances the space with both elegance and durability. Each bedroom features its own en suite bath and walk-in closet, offering comfort and convenience for you and your guests. Storage is abundant throughout the home--a rare find in Key West. For added peace of mind, the property is outfitted with full impact-rated windows and doors. The modern kitchen is equipped with sleek stainless steel appliances, perfect for entertaining or everyday living. The home features two-zone central AC (one unit per floor), and the third-floor primary suite offers a loft-like retreat with both central air and a mini-split system for personalized comfort. Currently operating as a successful vacation rental, this property offers excellent income potential. The home can be sold turnkey with furnishings included, giving buyers the option to move right in or start generating rental income immediately.

Experience the charm and ideal location that make Old Town Key West so special. Located in the desirable X Flood Zone, this two-bedroom, two-bath home offers an inviting layout filled with classic island character. A wine refrigerator provides a convenient touch for entertaining or enjoying a chilled bottle at the end of the day. The outdoor space is a true highlight, featuring a spacious 31-by-11-foot saltwater pool equipped with both a heater and chiller for year-round enjoyment. Ideally situated just minutes from Duval Street, restaurants, galleries, and shops, this home provides easy access to everything that makes Key West such a unique place to live and enjoy.

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

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.

Welcome to an extraordinary oceanfront residence in exclusive Casa Caselles, where two townhomes have been beautifully combined into one remarkable 4,224 sq. ft. luxury retreat. Completely reimagined, this one-of-a-kind home features a private interior elevator with automatic doors accessing all floors and effortless oceanfront and poolside living. Offering 4 en-suite bedrooms, 4.5 baths, 2 expansive living rooms divided by a wall insulated with commercial soundproofing, an exercise room, and a hidden office integrated into the custom kitchen. The chef's kitchen features an oversized island, European-style cabinetry, quartz countertops, BlueStar gas range, paneled Sub-Zero refrigerator, Cove dishwasher, U-Line ice maker, wine refrigerator, and Perlick refrigerator/freezer drawers. The family room includes an electric fireplace and custom wet bar. Twelve balconies and hurricane-rated sliding glass doors provide beautiful light in every room, with every bedroom offering private balcony access. Additional features include remote-controlled window coverings, a guest suite with zero-entry shower, multiple laundry areas, covered parking for four vehicles, an outdoor shower, and a whole-house generator that provides peace of mind. Residents also enjoy an oceanfront pool overlooking the Atlantic.

Nestled in the heart of Old Town Key West, this historic gem boasts an impeccable blend of classic architecture and modern amenities. With a rich history dating back to the late1800's, this captivating residence offers the perfect opportunity to own a piece of Key West's storied past. Listed on the National Register of Historic Places and awarded the Gold Star for Historic Preservations, 516 Elizabeth St. is the perfect example of a Classical Revival Eyebrow House - a style unique to Key West. The roof overhangs over the second floor windows onto classic porch columns giving the suggested appearance of 'eyebrows' providing protection from rain and sun allowing the inside to have fresh air even during the hot summer months. Upon entering the home, original Dade County pine walls, high 10ft ceilings, original double hung wooden windows exude the timeless elegance of a bygone era. While preserving its historic character, this home has been thoughtfully updated with modern amenities. The kitchen features custom wooden cabinets and stainless steel appliances and all bathrooms are beautifully renovated. Enjoy the convenience of contemporary living without compromising on the historic appeal. The primary bedroom and bathroom upstairs provide a tranquil retreat, and the guest bedroom downstairs with it's own bathroom is convenient and comfortable. French doors lead from the formal dining room and kitchen to a large sundeck with a covered dining area and extra lounging space to entertain. A Pool and new decking was just added to the property. This home has a rich history, with tales of past occupants, the Pinder family, and the unique stories of its heritage adding an extra layer of prestige and historical significance to its charm. This historic home is a rare find in a prime location, offering the best of both worlds. Sold furnished (art work excluded)!