luxury seaside houses for sale Summerland Key, United States

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.

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.

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.

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.

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!

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

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 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.