luxury houses for sale Big Pine Key, United States

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.

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available--each starting at $4 million--this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West.Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5 elegantly designed bathrooms, open balconies, and your own private rooftop terrace with sweeping water views. Built with impact glass throughout and outfitted with top-of-the-line appliances and finishes, these homes offer modern sophistication at every turn. Step outside to your own sparkling infinity-edge pool positioned right on the water, Turn Oceanside onto E Shore Dr (SR-942) at Mile Marker 25. The destination is ahead on the left.

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available--each starting at $4 million--this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West.Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5 elegantly designed bathrooms, open balconies, and your own private rooftop terrace with sweeping water views. Built with impact glass throughout and outfitted with top-of-the-line appliances and finishes, these homes offer modern sophistication at every turn. Step outside to your own sparkling infinity-edge pool positioned right on the water, Turn Oceanside onto E Shore Dr (SR-942) at Mile Marker 25. The destination is ahead on the left.

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available--each starting at $4 million--this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West.Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5 elegantly designed bathrooms, open balconies, and your own private rooftop terrace with sweeping water views. Built with impact glass throughout and outfitted with top-of-the-line appliances and finishes, these homes offer modern sophistication at every turn. Step outside to your own sparkling infinity-edge pool positioned right on the water, Turn Oceanside onto E Shore Dr (SR-942) at Mile Marker 25. The destination is ahead on the left.

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences availableeach starting at $4 millionthis private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West. Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5 elegantly designed bathrooms, open balconies, and your own private rooftop terrace with sweeping water views. Built with impact glass throughout and outfitted with top-of-the-line appliances and finishes, these homes offer modern sophistication at every turn. Step outside to your own sparkling infinity-edge pool positioned right on the water, and enjoy direct access to the sea from your assigned dock space in a private boat basinperfect for boating enthusiasts.nnThis gated, oceanfront community is ideally located just a block from a private airport that accommodates small aircraft, adding a level of convenience few properties can match. You'll also enjoy resort-style amenities, including on-site pickleball courts and a serene waterfront atmosphereall while being just a short drive to the shops, restaurants, and attractions of Key West.nnFor investors, Seven Palms Cove is an absolute dream. There are no rental restrictions, and similar properties just across the street are bringing in over $300,000 in annual income. Whether you're looking for a luxury vacation home or a high-performing investment property with incredible short-term rental potential, this community offers unmatched flexibility and return potential.nnWhether you're searching for a forever home, a tropical getaway, or a high-yield asset in the Keys, Seven Palms Cove delivers the perfect blend of comfort, exclusivity, and opportunity.nnCall us today for pricing details and to schedule your private tour of this exceptional waterfront retreat. Turn Oceanside onto E Shore Dr (SR-942) at Mile Marker 25. The destination is ahead on the left.

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available--each starting at $4 million--this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West.Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5 elegantly designed bathrooms, open balconies, and your own private rooftop terrace with sweeping water views. Built with impact glass throughout and outfitted with top-of-the-line appliances and finishes, these homes offer modern sophistication at every turn. Step outside to your own sparkling infinity-edge pool positioned right on the water, Turn Oceanside onto E Shore Dr (SR-942) at Mile Marker 25. The destination is ahead on the left.

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available--each starting at $4 million--this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West.Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5 elegantly designed bathrooms, open balconies, and your own private rooftop terrace with sweeping water views. Built with impact glass throughout and outfitted with top-of-the-line appliances and finishes, these homes offer modern sophistication at every turn. Step outside to your own sparkling infinity-edge pool positioned right on the water, Turn Oceanside onto E Shore Dr (SR-942) at Mile Marker 25. The destination is ahead on the left.

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available--each starting at $4 million--this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West.Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5 elegantly designed bathrooms, open balconies, and your own private rooftop terrace with sweeping water views. Built with impact glass throughout and outfitted with top-of-the-line appliances and finishes, these homes offer modern sophistication at every turn. Step outside to your own sparkling infinity-edge pool positioned right on the water, Turn Oceanside onto E Shore Dr (SR-942) at Mile Marker 25. The destination is ahead on the left.

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences available--each starting at $4 million--this private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West.Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5 elegantly designed bathrooms, open balconies, and your own private rooftop terrace with sweeping water views. Built with impact glass throughout and outfitted with top-of-the-line appliances and finishes, these homes offer modern sophistication at every turn. Step outside to your own sparkling infinity-edge pool positioned right on the water, Turn Oceanside onto E Shore Dr (SR-942) at Mile Marker 25. The destination is ahead on the left.

Introducing Seven Palms Cove, a one-of-a-kind new construction community that redefines luxury island living. With only seven exclusive residences availableeach starting at $4 millionthis private enclave offers a rare opportunity to own a slice of paradise just minutes from the heart of Key West. Each state-of-the-art home spans over 4,000 square feet and features 5 spacious bedrooms, 5.5 elegantly designed bathrooms, open balconies, and your own private rooftop terrace with sweeping water views. Built with impact glass throughout and outfitted with top-of-the-line appliances and finishes, these homes offer modern sophistication at every turn. Step outside to your own sparkling infinity-edge pool positioned right on the water, and enjoy direct access to the sea from your assigned dock space in a private boat basinperfect for boating enthusiasts.nnThis gated, oceanfront community is ideally located just a block from a private airport that accommodates small aircraft, adding a level of convenience few properties can match. You'll also enjoy resort-style amenities, including on-site pickleball courts and a serene waterfront atmosphereall while being just a short drive to the shops, restaurants, and attractions of Key West.nnFor investors, Seven Palms Cove is an absolute dream. There are no rental restrictions, and similar properties just across the street are bringing in over $300,000 in annual income. Whether you're looking for a luxury vacation home or a high-performing investment property with incredible short-term rental potential, this community offers unmatched flexibility and return potential.nnWhether you're searching for a forever home, a tropical getaway, or a high-yield asset in the Keys, Seven Palms Cove delivers the perfect blend of comfort, exclusivity, and opportunity.nnCall us today for pricing details and to schedule your private tour of this exceptional waterfront retreat. Turn Oceanside onto E Shore Dr (SR-942) at Mile Marker 25. The destination is ahead on the left.

Experience the perfect blend of character, durability, and Keys style at this quintessential cottage on the oceanside of Summerland Key. This thoughtfully crafted home welcomes you with the warmth of original Miami-Dade cypress floors and soaring ceilings that fill the interior with a sense of openness and timeless charm. Designed for peace of mind, the property boasts a metal roof, Hardie board siding, and upgraded impact windows and doors, ensuring both storm protection and long-lasting quality. Inside, the recently renovated retro-inspired kitchen takes center stage with teal blue appliances that add a playful splash of vintage appeal. Spacious living areas flow seamlessly to the screened waterside porch, where sweeping ocean views provide the ultimate backdrop for relaxing afternoons and entertaining guests. The bathrooms have been tastefully updated with custom tile and finishes, blending coastal elegance with modern function. Outdoors, a brand-new 100-foot-long pier dock with 10K lift stretches across turquoise waters, creating the perfect launch point for your boat, paddleboards, or evening sunset strolls. A separate outbuilding offers incredible flexibility—ideal as a workshop, anglers' room, or bonus storage for all your fishing and diving gear, plus an additional storage shed. Tropical landscaping enhances the property, while the serene oceanside setting offers quick access to deep water for world-class fishing, diving, and island-hopping adventures. Whether you're seeking a primary residence, an island escape, or a vacation investment, this Summerland Key retreat delivers it all—original craftsmanship, modern upgrades, and the unmatched beauty of living directly on the ocean. It's a rare opportunity to own a home that truly embodies the Keys lifestyle!

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!

OCEANFRONT , POOL & RARE BOAT BASIN DOCKAGE! Experience luxury open water living at this exceptional oceanfront retreat in the exclusive community of Summerland Cove, just 30 minutes from Key West. Designed for serious boaters and lovers of open water, this premier deep-water home offers breathtaking Atlantic views, immediate boating access, and the ultimate Florida Keys lifestyle. Beautiful newly painted exterior, this elevated 4 bed 3.5 bath home offers 2,766 sq. ft. of beautifully designed living space where soaring ceilings and walls of glass frame endless turquoise water views. Rare 3 bedroom suites with ensuite bathrooms, and a 4th bedroom with ensuite half bath. The expansive open-concept living and entertaining areas create a seamless indoor-outdoor flow perfect for relaxing or hosting guests after a day on the water. Separate laundry room is a bonus. A rare concrete dock with a protected cut-in boat slip provides quick deep-water access to the Atlantic with no long canal commute--placing you minutes from world-class offshore fishing, reef diving, sandbars, and endless boating adventures. Step outside to your private oceanfront oasis featuring a sparkling pool and spa, expansive lounging decks, and a poolside kitchen designed for sunset entertaining and waterfront gatherings. Panoramic open-water views and ocean breezes create the perfect Keys atmosphere. Upstairs, the spacious primary suite offers stunning ocean views, a private balcony, and a peaceful retreat overlooking the Atlantic. Additional features include impact windows and doors, a metal roof, a chef's kitchen with granite countertops and stainless steel appliances, plus convenient access to the nearby Summerland Key Cove Airport for easy fly-in/fly-out travel in light aircraft.This rare offering combines luxury living, protected deep-water dockage, immediate ocean access, and unforgettable open-water views in one of the Florida Keys' most sought-after waterfront communities.

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.

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.

Are you dreaming of your own personal paradise? Look no further than this stunning property in the highly sought after Cutthroat Harbor Estates. With features that check off every box on your list, this home is truly a gem. Enjoy the luxury of CBS construction and a spacious 9000 sq. ft. lot. The 65' dock has been newly resurfaced with composite decking and comes equipped with a 10k lb boat lift and Jet ski dock. Take a dip in the heated pool with a saltwater filtration system and relax under the 10 x 16' thatched tiki hut overlooking the canal. Enjoy evenings by the firepit on the beach area or rinse off in the outdoor shower with hot/cold water. Take in the stunning sunset views from the 35' high observation deck while sipping on a drink during happy hour. You'll love the beautiful landscape, including a Zen garden, and the convenience of a circular drive with pavers and plenty of parking space under the house. Other features include a new metal roof (2017), glass outside elevator, and a large storage room. With easy access to world-class fishing and diving, this property won't last long!

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.