Tropical Keys Oasis -- Waterfront Luxury Living Come experience this one-of-a-kind tropical oasis that feels like living at a Keys resort. Surrounded by lush landscaping, vibrant grass is the backdrop for nine coconut palms, five banana trees, two mango trees, and an avocado tree, this property bursts with natural beauty. Vibrant bougainvillea archways create a stunning entry to one of the most exquisitely landscaped homes on the island. Enjoy 60 feet of waterfront with an expansive maintenance free deck, a 15,000-lb boat lift, and a drop dock perfect for swimming in the lagoon or launching kayaks. Outdoor living is elevated to the next level- Inside, discover a newly renovated beautiful 4-bedroom, 2.5-bath home featuring a chef's kitchen "Pool permit application currently in progress."
Discover your personal island sanctuary in the heart of Cudjoe Key, where every day feels like Margaritaville. This stunning 2-bedroom, 2-bathroom single-family home has been thoughtfully updated to offer the ultimate waterfront lifestyle, featuring a sleek kitchen with a central island, 2025 updated appliances and two beautifully remodeled bathrooms. The interior glows with natural light, highlighted by impact-resistant windows and elegant French doors that lead to an open balcony. The floor plan is designed for effortless living, including a versatile bonus room and a separate dining area that provides a front-row seat to the tranquil canal. For added convenience, the spacious walk-in closet features an integrated 2025 washer and dryer, while a temperature-controlled thermostat and security system ensure year-round comfort and peace of mind. The exterior of the home is just as impressive, boasting brand-new Hardie Board siding updated within the last year and a full privacy fence that creates a secluded tropical retreat. Step outside to find a backyard oasis complete with swaying palm trees and an inground concrete pool featuring decorative tiling and a stylish paver deck. Boaters will fall in love with the concrete dock slip, which comes equipped with a 10,000 lbs elevator boat lift, offering ocean access in just minutes. Beneath the home, you'll find ample garage parking and massive storage space for your kayaks, grill, and water toys, along with a refreshing outdoor shower. Perfectly capturing that sought-after "Keys feel," this home is the ideal blend of relaxation and adventure.
Welcome to your slice of paradise! Down in Big Torch Key, you'll feel a sense of solitude, satisfaction and serenity. Minimal, if any, noise or light pollution on this Key; look up at night and you will see stars you've never seen before! Quick and easy access to the Atlantic and Gulf of America, plenty of fishing spots and places to relax on the water without those big upper Key crowds. The adjacent vacant lot for sale is owned by the same person - a perfect opportunity to purchase two lots and transform into one! With this dock size already at 65', imagine how many more boats you could dock with both lots! Vacant land MLS#A12018646 **Water photos at the end are for reference to show what the water looks like at the end of the canal. This home does not directly have this view**
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.
Great chance to own waterfront paradise with this elevated double-wide home situated on a rare double lot. Corner lot allows you to enjoy water on two sides of the property (plugged canals) —perfect for swimming, kayaking, paddle boarding, and relaxing by the water. Tucked away on a quiet cul-de-sac with lovely views, this property offers both privacy and charm, enhanced by mature landscaping. Inside, the home has been completely remodeled from top to bottom, providing a fresh, move-in-ready space. There's ample parking for all your needs, including room for an RV or boat trailer. Plus, a community boat ramp is located less than a mile away, making it easy to get out on the water anytime. Don't miss this unique waterfront property with endless potential!
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.
Opportunity to purchase for land value in Little Torch Key. Large lot with existing mobile home on site that is not habitable. Property is being marketed as land only. Lot is zoned IS (Improved Subdivision District), which typically allows for single-family residential construction subject to Monroe County Land Development Code and applicable ROGO requirements. Conveniently located less than 5 minutes from a public boat ramp. Buyer to verify zoning, building rights, and development potential with Monroe County. Do not enter structure. Sold AS-IS.
Following a monumental $200,000 price drop, this rare waterfront opportunity is available at an unbeatable price point. Launch your boat from your backyard for world-class access to the Atlantic Ocean and Gulf of Mexico. Unlock instant equity with virtual additions in the photos and below-market pricing; there is significant room to secure this property way below market value after completing updates similar to those shown. An update list with estimated pricing is provided upon request. This diamond in the rough is priced for a quick sale, allowing you to build custom equity from day one. With a solid foundation & breathtaking panoramic views, it's the ultimate project for a savvy investor to turn this house into the crown jewel of the shoreline! At this reduced price, it won't last.
Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light throughout. With kitchen and bathrooms ready for renovation, this is the perfect canvas to create a custom waterfront residence or maximize value through a strategic upgrade. Enjoy ample outdoor space with room for expansion, a pool, additional storage or enhanced landscaping - making this property uniquely versatile for both end-users and investors. Ideally located within close proximity to Key West, offering convenient access to world class dining, entertainment and boating, while still enjoying the privacy and tranquility of canal front living.
Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or income-producing rental. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white kitchen pops with marble countertops and a stunning blue tile backsplash, bringing those breezy ocean vibes right into your home. It's light, cheerful, and perfect for entertaining friends and family after a day on the water. And here's the best part — even though this property sits on a dry lot, you still enjoy beautiful open water views. Venture Out is one of the most sought-after gated communities in the Lower Keys, known for its active lifestyle and incredible amenities: Heated community pool, Marina & boat ramp with direct ocean and Gulf access, Tennis & pickleball courts, Basketball courts, Private convenience store, Children's playground & pool, Recreation hall, 24-hour gated security. Bring your boat, your golf cart, and your flip-flops — this neighborhood was made for enjoying the water. Located just 20 miles from Key West, you're close enough for dining, nightlife, and the airport — but far enough away to enjoy peaceful island living. If you've been dreaming of a cozy, beach-inspired Keys escape with income potential and resort-style amenities... this is the one.
Experience the ultimate Florida Keys lifestyle at 715 Caribbean Drive East in Summerland Key. Located in a desirable boating and aviation community, this property offers rare access to a private neighborhood airstrip, ideal for pilots and aviation enthusiasts. Designed for boaters, the home features a 60-foot dock and a 15,000-lb boat lift, providing easy access to open water, nearby sandbars, and world-class fishing. Enjoy a relaxed yet elevated island lifestyle where arriving by plane or boat is simply part of everyday living. A unique opportunity in one of the Keys’ most distinctive communities. The property also offers an assumable VA loan for qualified buyers and is available as a lease with an option to buy, presenting flexible opportunities for ownership. MOTIVATED SELLER
Courtesy: William Raveis Real Estate
561-576-7085
Tropical Keys Oasis -- Waterfront Luxury Living -- Come experience this one-of-a-kind tropical oasis that feels like living at a Keys resort. Surrounded by lush landscaping, vibrant grass is the backdrop for nine coconut palms, five banana trees, two mango trees, and an avocado tree, this property bursts with natural beauty. Vibrant bougainvillea archways create a stunning entry to one of the most exquisitely landscaped homes on the island. Enjoy 60 feet of waterfront with an expansive maintenance free deck, a 15,000-lb boat lift for up to a 33-foot boat and a drop dock perfect for swimming in the lagoon or launching kayaks. Outdoor living is elevated to the next level--exactly what you'd expect in the Florida Keys. Inside, discover a newly renovated beautiful 4-bedroom
Charming 2BR/2BA Keys home on Upper Sugarloaf. FULL HOUSE GENERATOR WITH TRANSFER SWITCH, Built on sturdy concrete pilings with Hardie board siding and a metal roof, Large workshop, storage space on first level with Laundry room, this three-story retreat of island living. Inside, you’ll find bright, cozy interiors with bamboo and ceramic tile floors and open living spaces for the relaxed Keys lifestyle. What truly sets this property apart is its rare private boat ramp on a deep-water canal with a boat lift—a feature difficult to replicate under today’s strict permitting process. Enjoy quick access to the open waters. Lot also provides plenty of room oasis to add a pool overlooking the canal. Whether as a full-time residence or vacation escape.
Welcome to your dream coastal retreat! This newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies, ideal for soaking in the sunrise or entertaining guests in true Keys style. Canal with direct access to the open ocean. No bridges, no hassle, just minutes to the Atlantic or Gulf. Inside, enjoy high-end finishes, plenty of natural light, and a layout designed for both relaxing and hosting. Whether you're seeking a full-time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box. The boat lift permit application has been submitted and is anticipated to be approved by closing.
Courtesy: TCE Realty
954-818-0856
This peaceful and quiet 2-bedroom, 1-bath unit is located in a serene residential neighborhood, offering a perfect escape. With no HOA to worry about, you'll enjoy a sense of privacy and freedom. The property features a beautiful swimming canal right outside, ideal for watching fish swim by or for relaxing activities like kayaking or paddle boarding. Please note, the canal is plugged and does not provide boating access, but there's a nearby boat ramp for convenient ocean access. Whether you're looking for a tranquil retreat or outdoor adventures, this location has it all.
Courtesy: The Keyes Company (Tequesta)
561-746-2436
Exceptional waterfront pool home in Summerland Key! This beautifully updated 2156sqft concrete home is located in the desirable neighborhood of Summerland Cove, known for its incredible boating access, deep-water flow through canals and close location to Key West (just 24 miles). Enjoy the ocean and lagoon views from the kitchen, living room, dining room, loft and screened patio, or from the 64' long concrete dock! Dock comes equipped with boat davits, fish cleaning station with water and swim ladder. With no rear neighbors there is plenty of privacy to lounge by the pool (has a pool heater/chiller), throw in a paddle board or kayak and cruise the lagoon or take advantage of the incredible boating/ fishing that Summerland has to offer with quick access to the Atlantic Ocean and the Gulf!
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All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.
Summerland Key is located in Florida. Summerland Key, Florida 33042has a population of 6,609. Summerland Key 33042 is less family-centric than the surrounding county with 17.31% of the households containing married families with children. The county average for households married with children is 20.65%.
The median household income in Summerland Key, Florida 33042 is $95,365. The median household income for the surrounding county is $73,153 compared to the national median of $69,021. The median age of people living in Summerland Key 33042 is 50.4 years.
The average high temperature in July is 89.4 degrees, with an average low temperature in January of 63.4 degrees. The average rainfall is approximately 44.4 inches per year, with 0 inches of snow per year.
