luxury houses for sale Summerland Key, United States

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.

Rare Private Sandy Beach - Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once-in-a-lifetime opportunity to own over 5 acres of sprawling oceanfrontage on exclusive Sugarloaf Beach, with over 500 feet of pristine sandy shoreline. Zoned Sub Urban Residential, this rare estate offers unmatched potential--create a private luxury compound, a boutique resort rental, or VIP luxury retreat. One of the few properties in the Lower Keys where lucrative nightly rentals are allowed with Special Vacation Rental Permits, this remarkable estate provides exceptional flexibility with ample room to expand. This estate has two existing Single Family Residences - the main house has 4 bedrooms 4 bathrooms and the second house has 2 bedrooms, 2 bathrooms and 1 half bath. Currently set up as two luxury nightly vacation rental homes! New 430-foot dock with stainless steel pilings, stainless steel support beams and composite decking. The 5-foot draft welcomes larger boats! Arrange private charter pick ups at the dock for your guests. Enjoy world-class boating, fishing and diving on your doorstep. American Shoal Lighthouseis only 5 miles directly in front of this spectacular property. Located on highly desirable Lower Sugarloaf Key in the Lower Keys, only 30 minutes to Key West, this hidden sanctuary is an unmatched offering for a discerning buyer seeking privacy, scale, and fantastic re-development potential. Nothing comparable exists in the area! Sugarloaf Beach remains one of the most coveted and rare stretches of beachfront in the Florida Keys. Whether you envision a secluded tropical retreat, a boutique luxury rental, or a visionary new oceanfront compound, this property is incredible with amazing potential to redefine with your personal touch. Opportunities like this come once in a lifetime. Take your private tour today and unlock the full potential of this iconic oceanfront estate!

This luxe, oceanfront estate will be sold at Luxury AUCTION Without Reserve on December 4, 2025! List price for REFERENCE ONLY. Offered in co-op. with Platinum Luxury Auctions. Inquire for details.Trophy Oceanfront Estate in THE PRIME location on Ocean Dr Summerland Key - surrounded by multi million dollar estates favored by celebrities and business leaders. Fly in and boat out! Located in one of the most exclusive areas of the Florida Keys, this one-of-a-kind estate offers the ultimate blend of luxury, privacy, and unmatched boating access. Set on a beautifully landscaped 37,400 sq ft lot with 120 feet of direct oceanfront, this residence is a rare opportunity to own a property designed for discerning buyers who demand the best. Boaters will be captivated by the 120,000 lb yacht lift, capable of hosting up to a 75 ft vessel--an extraordinary find in the Keys. The estate also features a private mooring buoy, two additional boat lifts, and a private boat basin. With exclusive bay bottom rights, this is a true boater's paradise. Inside, the home boasts 5 bedrooms, 4 full baths, and 2 half baths. The spacious guest suite features a separate sitting area currently set up as a gym with a half bathroom, and a large bedroom with ensuite bathroom. The open-concept living area showcases vaulted ceilings, a chef's kitchen with high-end appliances, and seamless indoor-outdoor flow to a sprawling tiled patio. Enjoy breathtaking views of the Atlantic and Little Palm Island from the raised pool, spa, and covered bar area, perfect for entertaining in style. The estate also includes a private beach, desalination plant, and backup generator, ensuring complete self-sufficiency. Additional highlights: one-car garage, large storage space, circular drive, and lush tropical grounds that evoke a luxury resort. Fly into paradise at Summerland Key Community Airport for residents only - helicopter and small aircraft. This exceptional property offers the pinnacle of Florida Keys living.

MOTIVATED SELLER! Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living space ideal for coastal living. Built for both comfort and peace of mind, the home features a metal roof installed in 2018 along with impact-rated windows and doors throughout. Enjoy added privacy and nightly sunset views over the protected salt marsh directly across the street—an unspoiled natural backdrop that will never be developed. Boaters will appreciate the free-flowing, clear-water canal with excellent access to both the ocean and the bay. The private dock with a 7,000-lb side-lift boat elevator makes heading out for fishing, diving, or sunset cruises effortless. The spacious lot offers a large driveway, double covered parking, and ample room for boat trailers and additional vehicles. Downstairs, a full concrete pad and enclosed angler's room provide the perfect space for storing fishing gear, dive equipment, and all your island toys. Located near mile marker 28.5, Jolly Roger Estates is a peaceful, palm-lined waterfront community on the Atlantic side of Little Torch Key, offering direct access to Pine Channel and world-class boating, fishing, and diving at nearby Looe Key Reef. Just 24 miles from Key West, this exceptional property delivers the perfect blend of island tranquility and convenient access to dining, entertainment, and amenities—an ideal full-time residence, second home, or investment in the Florida Keys lifestyle.

Welcome to Morning Glory - The Dolphin House, a rare direct oceanfront retreat in the Florida Keys. Situated on an oversized oceanfront lot, this 4BR/3.5BA home offers 2,478 SqFt of coastal elegance, breathtaking Atlantic views, and the peaceful lifestyle buyers dream about. Wake up to stunning sunrises, relax by the pool beneath swaying palms, enjoy waterfront dining with guests and friends, or unwind by the fire pit under the stars. Every space was designed to feel warm, inviting, and effortlessly luxurious. More than a home, this is a private sanctuary where memories are made and life slows down.

Introducing Blue Water Lagoon Estate! Experience unmatched privacy and exceptional waterfront living at this gated 2.33-acre oceanfront estate in exclusive Sugarloaf Beach -- a location famously featured in the film ''True Lies''. Designed for the avid boater and those seeking a resort-style lifestyle, this 5,208 sq. ft. residence offers rare amenities and direct access to world-class fishing and diving.A protected 6-boat basin with room for extra boats is the centerpiece of the waterfront, complete with 25K and 16K lifts, a boat ramp, sandy beach, lookout point, and composite observation deck. After a day on the water, unwind in the lagoon-style saltwater pool with heater, chiller, and custom water features. The expansive tiki bar includes TVs, True refrigerator/freezer drawers, and an ice machine--perfect for effortless outdoor entertaining. Additional features include a firepit, private sandy beach, and a full outdoor kitchen equipped with built-in BBQ, Viking appliances, and True refrigeration.The upper level offers a bright and open Great Room with sweeping ocean views, a spacious dining area, and a chef's kitchen with stainless appliances. Two covered verandas provide ideal spaces for taking in the breezes and panoramic vistas. The primary suite features an office, en suite bath, walk-in closet with laundry, sunroom, and loft. Two additional upstairs guest rooms comfortably accommodate visitors, while the separate downstairs living area offers three more guest bedrooms for privacy and flexibility.Designed for hosting and convenience, the home is equipped with a Sonos sound system, property-wide Wi-Fi, abundant storage, a two-car garage with fishing lockers, and generous parking along a winding paver driveway. Lush, mature landscaping surrounds the property, creating a serene and secluded Sugarloaf Key retreat.Call for more information today!

Introducing Blue Sky Pointe - the crown jewel of Sugarloaf Key. Perched on a gated 33,750 sq. ft. peninsula with approximately 730 feet of waterfront, this spectacular 4 Bed, 3.5 Bath modern coastal showpiece is surrounded by glistening water and enjoys Keys famous sunset views over Sugarloaf Sound. Fully renovated with premium craftsmanship, the home features a standing seam metal roof, PGT impact windows/doors, and Hardi board siding. Inside, enjoy a sunlit open-concept floor plan with soaring ceilings, a gourmet kitchen with quartz counters, premium stainless appliances, gas stove, a hidden butler's pantry, and a waterfront Bedroom wing, all oriented to frame the water from every room. Step outside and immerse yourself in resort-style living with a heated and chilled waterfront pool, soothing spa, hot tub, invigorating cold plunge, and a fire pit encircled by flickering tiki torches to gather with friends and family while sipping cocktails as the sun melts into the horizon. Lounge on the expansive covered porch while enjoying views of the peaceful nature preserve for incredible bird watching, and a setting that offers total privacy and serenity. Boaters will love the protected canal access with 2 boat lifts (8K & 12K lbs), just minutes from open water. Additional features include a 4-car garage with EV charger, covered RV Tiki with 50 amp service, whole-house 35kW generator (750-gal tank), whole house water softening system and Sonos throughout, including garage and outdoor zones. Whether you're seeking a private sanctuary, a trophy lot, or the ultimate Florida Keys lifestyle, Blue Sky Pointe delivers. This is the most premiere lot on Sugarloaf Key a once-in-a-lifetime opportunity.

Nestled within this 280 ft of concrete walled and gated property lies a tropical oasis that epitomizes Keys living. Situated on a huge,12,000 sq ft corner lot that provides an exclusive island vibe with lots of privacy that comes complete with 200' of canal frontage, a 133' concrete dock, a new 10k lb boat lift, fish cleaning station, and travertine steps into the sparkling water for an enjoyable saltwater swim. Outdoor lighting perfects this entire property along and under the dock and seawall as well. A new higher end fiberglass pool and spa made by Latham which are built with double thick fiberglass complete with heater and chiller is just waiting for you to enjoy after a day on the water or an evening of entertaining. The adjoining new tiki hut, complete with a NewAge summer kitchen, a dining area and ready for happy hours and fish tales. The bar and lounging area located across from the tiki hut provides a comfortable lounging area complete with a nice storage area. Pavers adorn all the open spaces surrounded by new exquisite, lush landscaping maintained by a 5-zone irrigation system. A new standing seam metal roof was installed in 2024. Oh and did I mention a real fire pit. This gorgeous home is all about being outdoors and enjoying the Florida Keys tropical ambiance. The main living area has an open kitchen concept with a center island (buyers choice), gas stove, new appliances, and dining table. Guest bedroom is on the main floor with a full bath and walk in shower. Upstairs has two master suites, one with a stand-alone tub and walk in shower and the other with a walk-in shower only. All the bedrooms have balconies overlooking this peaceful, delightful, property. All the furniture is brand new and comes included with the purchase. With the proximity to Key West, and all the excitement and nightlife and the world class fishing and diving out your back door, the world is your oyster in this Fabulous Florida Keys slice of paradise. Don't let this one get awa

Coastal Haven in Summerland Key Cove Isles! Calling all boaters--this move-in-ready waterfront oasis sits on a premier deep-draft canal with quick access to both the Atlantic and Gulf! Extensively updated in 2025 with a new metal roof, spray foam insulation, interior and exterior paint, new LVP flooring, gutters, soffits, fascias, new pool deck, and Trex decking, this home radiates fresh coastal style. The lush tropical yard is a true paradise with all new low-maintenance landscaping, irrigation, evening lighting, and artificial turf.The 75-foot concrete dock offers deep-water access for large vessels (current owner has a 42' boat), complete with a new covered fish-cleaning station. Entertain with ease under the spacious covered patio or on the large upper deck overlooking the sparkling canal. The enclosed garage provides secure storage, while the newly paved driveway offers ample parking for vehicles, trailers, and even an RV--complete with hookup. Lower level storage and bonus space.Just minutes from the Summerland Key airstrip, this property offers the ultimate convenience--fly in and boat out! Experience the best of Keys living in one of the most desirable neighborhoods in the Lower Keys. Don't miss out on this one--your coastal haven awaits!

Discover the Ultimate in Luxury Waterfront Living at This Prime Oceanfront Tropical Gem in Summerland Key.Located in the prestigious community of Summerland Cove--just 30 minutes from Key West--this exceptional deep-water oceanfront estate offers the perfect blend of privacy, beauty, and unparalleled boating access.Completely rebuilt in 2006, this elevated 4BR/3.5BA residence spans 2,766 sq. ft. and is designed to showcase sweeping, unobstructed views of the Atlantic. The grand open living and entertaining space features soaring ceilings and walls of glass that frame endless turquoise water vistas, creating an airy coastal ambiance throughout.Step outside to your own private resort with a sparkling oceanfront pool and spa, surrounded by expansive decks ideal for sunset cocktails or gatherings with family and friends. A rare concrete dock with a cut-in boat slip provides quick, direct access to world-class fishing, diving, and boating--an extraordinary feature highly coveted in the Florida Keys.Outdoor living is elevated with a poolside summer kitchen, multiple lounging decks, and panoramic views in every direction. Upstairs, the spacious primary suite offers breathtaking ocean views, a private balcony, and the ultimate retreat for rest and relaxation.Additional features include impact windows and doors, a metal roof, and a chef's kitchen with granite countertops and stainless steel appliances.This is Luxury Coastal Living at its Finest--a premier oceanfront home offering rare amenities, deepwater access, and unforgettable views in one of the Florida Keys' most sought-after communities.

Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of your gear. Inside, the spacious 3 Bedroom, 3 Bath 3,056 sq. ft. home comfort and style blend with ease. The kitchen stands out with 6-burner Viking Range, Viking dishwasher, cabinet-front refrigerator, stainless appliances, pantry and generous space for entertaining, flowing seamlessly into the main living areas. Soaring ceilings fills the home, creating a bright and inviting atmosphere throughout. Upstairs a loft-style office and a dedicated theatre room offering a bar with beverage center provides the perfect setting for movie nights or game-day gatherings. The primary suite serves as a private retreat, complete with a lavish bath with bidet, separate shower and a relaxing jet tub, ideal for unwinding at the end of the day. Porches on both sides of the home overlook the canals and lead to a unique sandy point at the corner, offering a peaceful setting to take in water views and stunning sunset skies. After a day on the water relax by your waterfront heated salt pool or enjoy sipping cocktails on the screened lanai. Additional amenities include impact windows and doors, whole house generator and ice machine. Cudjoe Gardens is an upscale waterfront community known for its ground-level concrete homes thoughtfully built above the floodplain. The neighborhood is home to Cudjoe Gardens Marina, a convenient full-service stop for fuel, bait, and refreshments on your way to world-class fishing and diving. Residents also enjoy The Bent Prop, a beloved waterfront restaurant offering a true taste of the Keys lifestyle.

Contemporary coastal living meets premier boating access in this elevated 2BD/2BA waterfront home on a 12,500 sq ft canal-front lot with 100 ft of waterfront and coveted SW exposure. Ideally positioned on one of the only flow-through, crystal-clear canals in desirable Sugarloaf Shores, offering exceptional access to both the ocean and backcountry.Light-filled interiors showcase impact windows and doors, wood-look porcelain flooring, and an open-concept chef's kitchen with porcelain countertops, custom cabinetry, stainless steel appliances, and an entertainer's bar. The spacious great room and dining area flow seamlessly to a covered, screened porch--perfect for alfresco dining, sunset views, and watching dolphins pass through to Sugarloaf Sound.A full wraparound composite deck with marine-grade stainless steel railings enhances outdoor living. The expansive, landscaped yard offers ample room for a pool and includes two RV hookups. A rare opportunity for boaters seeking clear water, prime location, and effortless Keys living.

RARE Solar-Powered Waterfront Tropical Gem with TESLA Solar Storage Banks on Prestigious Sugarloaf Key! A rare opportunity to own a fully solar-powered waterfront residence featuring 26 solar panels and two Tesla Solar Powerwall storage banks, offering exceptionally low energy costs, backup power, and the potential to earn credits by supplying excess energy back to the grid. This elevated 3 BD, 2 BA, 1,764 SF home sits on exclusive Southpoint--only three homes from open water and just 20 minutes to Key West.Step inside to a breathtaking cathedral Cupola, soaring above the open living, dining, and great room. Impact-glass windows fill the space with natural light, highlighting the home's tropical architecture and warm coastal finishes. The kitchen is designed for effortless entertaining with a double island, stainless steel appliances, and new quartz countertops. The split floor plan creates exceptional privacy. The primary suite features a large walk-in shower, jacuzzi tub, double vanity, and a spacious walk-in closet that connects to a versatile laundry/fitness/office room--also home to the Tesla storage banks. The opposite wing offers two guest bedrooms and a dual-access bathroom with two private vanities. Enhance your waterfront lifestyle with an impressive concrete boat ramp for jet skis, boats, kayaks, and paddleboards, plus a newly installed 10,000 lb boat lift on a deep, wide, crystal-clear canal providing fast access to both the Gullf and Atlantic. The oversized 15,000 SF lot bursts with vibrant tropical landscaping and includes a newly completed tropical pool with natural rock feature. Enjoy sunset views and star-filled nights from the rooftop observation deck. Additional features include Andersen impact windows and sliding glass doors, low insurance costs, covered parking, and excellent storage below the home.A rare Keys offering combining sustainable energy, modern resilience, and luxurious waterfront living--an exceptional opportunity in today's market

Welcome to Pink Sands, a Glenn Gray-designed waterfront retreat where the vibrant colors and laid-back elegance of the Bahamas meet the timeless beauty of the Florida Keys. Recognizable by its signature pink façade and blue metal roof, this exceptional Summerland Key residence captures the spirit of island living while offering the quality, comfort, and peace of mind of modern CBS construction. Set along a protected canal with 125 feet of concrete dockage, two boat lifts, and direct deep-water access to both the Atlantic Ocean and Gulf of Mexico, this waterfront home is perfectly positioned for effortless days on the water, from world-class fishing and diving to sunset cruises and sandbar adventures. Impact windows and doors and thoughtfully designed indoor-outdoor living spaces create a home that is as durable as it is inviting. Sweeping open ocean views from the main living level and third-story observation deck provide the perfect backdrop for sunrise mornings and starlit evenings. A charming detached guest cottage connected by a covered breezeway creates a private compound ideal for hosting family and friends. The oversized homesite offers exceptional flexibility with ample room to add a custom pool, expand outdoor entertaining areas, or further enhance the property to suit your vision. Just 35 minutes from Key West, Pink Sands feels as though it belongs on Harbour Island while remaining firmly rooted in the authentic charm of Summerland Key. Blending Bahamian-inspired architecture with the confidence of newer CBS construction, exceptional boat dockage, direct ocean and Gulf access, and endless opportunities for future customization, this is a rare opportunity to own a distinctive Florida Keys waterfront home. Minutes from Looe Key Reef, Content Keys, and the backcountry flats, this exceptional location offers unparalleled access to some of the Florida Keys' most sought-after boating, fishing, diving, and paddleboarding destinations right from your private dock.