Experience the PINNACLE of luxury waterfront living at this exceptional oceanfront residence on prestigious Flagship Drive. Completely reimagined with uncompromising attention to detail, this exquisite 4-bedroom, 3.5-bath home blends sophisticated design with the relaxed elegance of the Florida Keys. From the moment you enter, you'll be captivated by the expansive open-concept floor plan, breathtaking ocean views, and refined finishes throughout. Oversized 41-inch porcelain tile flooring, designer lighting, premium fixtures, and custom craftsmanship create a timeless, contemporary aesthetic that complements the stunning waterfront setting. The chef-inspired kitchen flows seamlessly into the spacious living area, making it ideal for both everyday living and entertaining. Walls of glass invite natural light while framing spectacular turquoise water views. The luxurious primary suite serves as a private retreat with serene ocean vistas and a beautifully appointed spa-inspired bath. Three additional bedrooms and office provide comfortable accommodations for family and guests. Outdoor living is equally impressive. Multiple covered terraces offer the perfect place to relax while enjoying ocean breezes and unforgettable sunsets. The resort-style pool is complemented by a charming tiki hut, creating an inviting setting for entertaining or unwinding after a day on the water. Boaters will appreciate the exceptional dockage featuring two boat lifts, providing convenient access to the Atlantic Ocean for world-class fishing, diving, and boating. A spacious two-car garage offers ample room for vehicles, storage, and recreational gear. Perfectly positioned in one of the Lower Keys most desirable waterfront communities, this remarkable residence delivers an extraordinary combination of luxury, location, and the ultimate Florida Keys lifestyle. Every detail has been thoughtfully curated, creating a move-in-ready waterfront masterpiece that is as elegant as it is in
Located at the end of a quiet street in Sugarloaf Key, this 2 bedroom, 2 bath canal-front home is only two lots in from open water and offers open water views from the living room and large deck. Start the morning with coffee overlooking the ocean, then hop in the boat and be minutes from Bow Channel with easy access to both the ocean and Gulf side. Inside, the home feels open, warm, and comfortable with vaulted wood-beamed ceilings, a spacious great room, impact windows and doors, and a well-designed kitchen with granite counters, and a large island with extra seating and storage. The primary suite has its own upgraded ensuite bath, walk-in closet, canal views, and private screened balcony with additional stairs to the backyard. The guest bedroom is equipped with a Murphy bed to take your home office to guest ready in minutes. This home also has an additional large walk in, interior storage closet. The large lot offers the convenience of an RV hook-up, plenty of covered parking, shaded outdoor living space, a propane whole-house generator and a 68 ft. concrete dock. For those looking for peace, privacy, nature, and true Keys boating access, this Sugarloaf Key home checks all the boxes.
Imagine having the freedom to create your own secluded retreat in the heart of the Lower Florida Keys. This remarkable offering includes two adjacent 2.5-acre parcels, combining for approximately 5 acres--an exceptionally rare amount of land in the Florida Keys. Existing improvements include two separate residences, each offering one bedroom and one bathroom. One parcel is improved with a single-family home, while the other features a manufactured home. Both properties have established electric service and are connected to the sewer system, making them immediately usable while you plan for the future. The parcel at 2231 Middle Torch Road includes a ROGO allocation, creating an outstanding opportunity to construct a new home. Conceptual renderings have already been prepared to showcase one possible vision, but the possibilities are yours to define. Whether your goal is a peaceful island getaway, a private homestead surrounded by nature, or a property designed for generations to enjoy together, the setting provides the space and flexibility to bring those ideas to life. Spend your days boating the turquoise waters of the Lower Keys from a nearby private boat launch, then return home to the quiet beauty of native vegetation, abundant wildlife, and the iconic Key deer that call this area home. Opportunities to own five contiguous acres in the Florida Keys are exceptionally scarce. Combining privacy, natural beauty, and future development potential, this one-of-a-kind property offers the chance to create something truly special in one of the Keys' most unique settings.
ROGO EXEMPT CANALFRONT WITH GREAT SUNSETS AND OPEN WATER VIEWS READY FOR YOU TO BRING YOUR BOAT WITH STEP DOWN DOCK. DOCK NEEDS SOME TLC. ACTIVE WATER METER ON SITE, SEWER STUBBED IN AND READY FOR CONNECTION AS A PRIOR HOME WAS DEMOLISHED. BUYER TO VERIFY ALL INFORMATION. POWER IN FRONT. SURVEY AVIALABLE. TWO STORY HOME WOULD PROVIDE SPECTACULAR VIEWS AND A TREMENDOUS OPPORTUNITY FOR YOUR VISION, NOW OR LATER. OWNER/AGENT SOLD AS IS.
Beach House Paradise in Summerland Key. Nestled in one of the Lower Keys' most desirable oceanside communities, this exceptional oceanfront retreat offers the perfect blend of luxury, privacy, and island living. A charming thatched-covered lanai and custom bamboo-etched glass doors welcome you into an open-concept floor plan where floor to ceiling windows frame breathtaking Atlantic Ocean views. The spacious living area flows effortlessly to an expansive waterfront terrace overlooking the pool, creating the ultimate indoor-outdoor lifestyle. Designed for entertaining, the lower level features a custom tiki-style bar, outdoor cooking area, hot tub, and multiple gathering spaces. Relax by the resort-style pool, unwind on your private sandy beach beneath the swaying palms, and enjoy the unparalleled beauty of oceanfront living. Located just minutes is Summerland Key's private airstrip, world class boating, fishing, diving and the renowned Looe Key reef, this exceptional property offers the very best of the Florida Keys lifestyle. 361 Avenue D is a rare opportunity to own your own slice of paradise.
Bring your water toys & experience island living in this newly built waterfront home in Summerland Key. The residence offers 3 bedrooms 2 bathrooms spacious modern design & trim. A durable metal roof, Hardie-board siding, impact windows and doors. Enjoy relaxing or entertaining on the covered porch, step out on the composite dock and be on the open ocean or Gulf in minutes, perfect for boating, fishing and sunset cruses. Keys biking trail steps away. Great local restaurants, convenient local island grocery store. Private Summerland Key Airstrip. Centrally located between Marathon and Key West, this property combines modern construction, waterfront convenience, low maintenance and easy access to both Keys' amenities. Ideal for a vacation retreat or full time home. Schedule your private showing today.
*SWIMMING POOL BEING BUILT NOW! Construction process underway. * Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West! Tucked away in a quiet, peaceful neighborhood. Inside, the home features generous living space, providing ample room to stretch out and make it your own. Indoor-outdoor living is at its best here, with a private swimming pool just steps from the back door--perfect for unwinding after a day on the water or enjoying sunny Florida afternoons. For boaters, the canal location offers easy water access, along with the convenience of a 10,000-pound boat lift to safely store your boat out of the water. After a day of fishing, cruising, or exploring, dock your vessel with ease and relax as you take in the beautiful waterfront views. Or stay on the screened in covered porch and enjoy the Keys breeze! The roughly 1100 sqft garage/lower enclosure offers abundant storage space for all your tools, pool toys, and outdoor gear, keeping everything organized and clutter-free. Plus, with a newly built home designed to the latest building codes, you'll benefit from low insurance rates, ensuring peace of mind and minimized risk from tropical weather. This home offers the ideal combination of comfort, convenience, and the laid-back Florida Keys lifestyle. Don't miss the opportunity to make it yours--schedule your private showing today! Seller is licensed FL real estate agent.
Welcome to your oceanfront retreat on Cudjoe Key, where panoramic wide open ocean views, exceptional outdoor living, and easy boating access come together to create the quintessential Florida Keys lifestyle. Built on a lot and a half with durable CBS construction, this inviting 2-bedroom, 2-bath, 1,587 sq. ft. home is perfectly positioned to take advantage of its spectacular waterfront setting. The light-filled interior flows effortlessly into the spacious screened porch where you'll enjoy ocean breezes, morning coffee, waterfront dining and unforgettable sunrises and moonlit evenings. Just beyond, an expansive deck provides even more space for entertaining or simply relaxing while overlooking the endless blue waters. Inside, the primary suite serves as a peaceful waterfront sanctuary, featuring a private en-suite bath, walk-in closet, and sliding glass doors that open directly to the deck, allowing you to wake up to breathtaking ocean views each morning. A comfortable guest bedroom offers welcoming accommodations for family and friends. Boaters will appreciate the dock and davits, providing convenient access to the Atlantic for world-class fishing, diving, sandbar adventures and sunset cruises. The lower-level enclosure offers abundant storage for kayaks, paddleboards, fishing gear, and all of your island essentials. Whether you're entertaining guests on the spacious outdoor living areas, heading out for a day on the water, or simply soaking in the tranquil open water views, this Cudjoe Key waterfront home is your opportunity to embrace the relaxed, waterfront lifestyle the Florida Keys are known for.
Wake up to breathtaking Florida Keys sunrises from this exceptional oceanside waterfront home in Cudjoe Key. Offering 1,596 square feet of living space on an 8,920-square-foot lot, this CBS-built residence features 3 bedrooms and 3 bathrooms, + Office/beddroom,combining durability, comfort, and the relaxed island lifestyle you've been dreaming of. Designed for both everyday living and entertaining, the home offers spacious living areas filled with natural light and beautiful canal views. Step outside to your private tropical retreat where a heated saltwater pebble coated pool overlooks the water, creating the perfect setting for morning coffee, afternoon relaxation, or entertaining family and friends. Built to withstand the Keys environment, the home features solid CBS construction and a metal roof for added peace of mind. The oceanside location provides easy access to world-class fishing, diving, snorkeling, and boating adventures. A marina and waterfront restaurant are conveniently located within walking distance, allowing you to enjoy dining, cocktails, and boating amenities just moments from your front door. Whether you're searching for a full-time residence, vacation getaway, or investment opportunity, this waterfront property offers the ideal blend of boating access, outdoor living, and the laid-back charm of the Florida Keys.
A Classic Keys Boating Cottage! Exceptional value for a 3 bedroom 2 bath waterfront home in the Lower Keys! With 60' of seawall, enjoy easy boating access to nearby hot spots in the gulf and ocean side. The State Road 4a boat ramp is just a few doors away which is so convenient to launch your boat. Plenty of parking out front and room for a pool. Featuring laminate floors, a dedicated laundry space, on demand hot water heater and a large pantry storage closet.
Discover one of the Florida Keys' most extraordinary private island retreats. Encompassing 9.69 acres of pristine tropical landscape, Howell Key offers an unparalleled opportunity to own an off-grid luxury island surrounded by breathtaking open water views from sunrise to sunset. Designed for those who value privacy, adventure, and refined coastal living, the island features miles of groomed trails, resort-style pool, sandy beach, pickleball court, chicken coop, pasture, and expansive barn. At the heart of the island sits a beautifully crafted 5-bedroom, 4-bath residence encompassing 3,352 sq. ft. Cathedral ceilings, elegant coastal interiors, and expansive gathering spaces create a warm yet sophisticated atmosphere, while walls of impact-rated glass invite natural light and panoramic water views throughout the home. The layout is designed to comfortably accommodate family and guests with an attached primary suite serving as a private sanctuary, complete with a generous walk-in closet. A separate guest wing is accessed via a breezeway and features its own living room, breakfast bar, and 2 private bedrooms creating a welcoming retreat while maintaining privacy from the main residence. Beyond the main residence, the island unfolds as a private playground. Wander along groomed walking trails, relax by your saltwater pool, launch your kayaks from your own sandy beach, enjoy pickleball with friends, or watch the sunset from your dock. Built for resilience and efficiency, the home features SIP construction, Hardie Board siding, a standing seam metal roof, impact windows and doors, whole-house reverse osmosis water filtration, and an off-grid solar power system. Elevated approximately 10 feet above base flood elevation, the property offers both sustainability and peace of mind. Island purchase comes with barge, golf cart, tractor, and a private mainland lot for car storage. Howell Key is a private island lifestyle few will every have the opportunity to experienc
Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new and low maintenance. And the best part? The permit is already secured, so your home gets built now instead of years from now.
53 Treasure Chest Drive in Cudjoe Key is more than a home--it's your chance to own a piece of paradise. From the moment you arrive, you'll feel the laid-back island vibe paired with the comfort and security today's buyers demand, including impact windows and doors for year-round peace of mind. Bright, airy, and designed for easy living, this property invites you to slow down, entertain more, and enjoy everything the Florida Keys has to offer. Whether it's morning coffee in the tropical breeze or evenings under the stars, this home delivers the lifestyle people dream about--but rarely find. And the best part? You're just a short drive to Key West, giving you access to world-class dining, nightlife, and boating--while still enjoying your own private escape.
3 bed 2 bath stilt home built in 2018 in sought after Sugarloaf Key. Open concept floor plan, large kitchen with an abundance of large white cabinets, kitchen island overlooking living area, stainless steel appliances, light and stylish colors throughout. Wood-look tile plank flooring, crown molding, 9-ft ceilings, recessed lighting and ceiling fans in all bedrooms and living room. Full size laundry room and on-demand hot water heater. Large master bedroom with en-suite bathroom, dual sink vanity and large walk-in closet. 2 guest bedrooms and full guest bathroom. Large covered porch off the main living/kitchen area, fenced on 3 sides. Newer downstairs storage room, room for boat/trailer; boat ramp is one street over and you are less than a mile from Sugarloaf Elementary and Middle school. Quick access to Key West and bases.
Oceanside canal-front home in the desirable Breezeswept Beach Estates neighborhood of Ramrod Key. This 3-bedroom, 2-bath residence features a private pool and is ideally positioned for enjoying the Florida Keys lifestyle, with quick access to world-class boating, fishing, diving, and snorkeling at nearby Looe Key Reef. The adjacent buildable lot is also included, offering buyers the opportunity to expand their investment, construct a guest house or second residence, or simply enjoy additional privacy and space. T Located just minutes from Picnic Island and within walking distance of the local favorite, The Tiki, this property combines waterfront living, convenience, and investment potential. Whether you're seeking a primary residence, vacation retreat, or income-producing property, this canal-front home offers an exceptional opportunity in one of the Lower Keys' most sought-after oceanside communities.
Welcome to 629 Powell Drive in Little Torch Key, the lowest-priced fully stilted CBS home currently available in the Lower Florida Keys. This elevated 2-bedroom, 1-bath canal-front home offers the ideal combination of affordability, boating access, and island living. Built for peace of mind, the home features a 2018 metal roof, accordion shutters on the doors, and panel shutters for the windows. Relax on the spacious east-facing porch, perfectly positioned to capture the prevailing trade winds while enjoying peekaboo open water views and cooler afternoon temperatures. Situated on a generous 7,400-square-foot lot, the property offers a huge paver driveway with ample room for multiple boats, trailers, RVs, and guests. The backyard provides plenty of space for a resort-style pool, creating the ultimate Keys retreat. Boaters will appreciate the deep, clean canal, concrete dock, and quick ocean access through Pine Channel, offering outstanding fishing, diving, and snorkeling opportunities. Downstairs, a massive enclosed storage area provides plenty of room for all your gear and water toys. Located in a desirable waterfront neighborhood with a community boat ramp and within walking distance of one of the Lower Keys' most popular waterfront tiki bars, this property delivers everything buyers love about the Florida Keys lifestyle at an exceptional value.
Canal-front Paradise Awaits! Incredible view from your back deck! Unit 424 in Venture Out. Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community. This beautiful canal front home boasts: * Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall. * Community Boat Ramp and boat washdown station. * Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area and more! * Well-Maintained: This home has been very well cared for and updated and is ready for you to move in and enjoy. * Gated Community: Cruise around the property in your golf cart to the community store or to join in on the numerous community activities. Live with peace of mind in a secure and exclusive gated community. Don't miss this rare opportunity to own a piece of paradise! * Exclusivity: The gated community adds a sense of security and prestige. * Nightly Rentals Allowed! * Excellent rental income potential!!
Beautiful .55 acre lot in Summerland Key, FL. Summerland Key is a unique fly-in community with a private airstrip and marina close by. SUMMERLAND ESTATES SUMMERLAND KEY PB2-167 PT LT 25 (LOT A 90 FT X 264.75 FT). Buyer is responsible for conducting due diligence on the property prior to purchase.
Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor. 5 (2 bedroom one bath cottages) and one (3 bedroom 2 bath house), 6 water meters, 6 electric meters. Heated salt water pool. The property is also listed with 9 additional units MLS #612522.
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."
Pilots, this is a great opportunity to build your dream home with access to Summerland Key's private airport, and enjoy access to the Blanche Bergin Marina Park, complete with boat ramp and available dockage for a fee. This property is a fixer-upper (ROGO letter in hand), located on Summerland Key, at the base of the airport runway. 2/1 on one side, and an additional 12 x32 en suite with a separate entrance on the other side. The home sits on a rare double lot totaling 11,000 SF. If you like privacy, this is it, with only one neighbor next to you. There is an expired permit, and one open permit the buyer will have to assume responsibility for. There are no open code cases on the property. The seller doesn't have insurances. A home inspection is recommended, however, the seller will not make any repairs, or offer to pay for any repairs. No less than 24 HOUR NOTICE TO SHOW REQUIRED.
Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile floor throughout. Enjoy the tropical landscaped backyard while grilling dinner or relaxing on your private deck. Indulged in the community's amenities, including an oceanfront heated saltwater pool and jacuzzi for ultimate relaxation. A marina with a fuel dock, convenient store and boat launch for the boater enthusiasts. Stay active and engaged with pickleball and tennis courts! And for Kids' there's a playground where the little ones can have fun. Venture Out is an individual owned residential condominium community with 24 hour gated security, located only 19 miles from the vibrant city of Key West! Parking for one vehicle, no age restrictions, two pets allowed, and transient (1 day) rentals are permitted. Possible Seller Finance
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.
Waterfront living meets comfort and functionality in this move-in ready canal front home. Offering 120 feet of concrete dockage in a deep water canal. Quick boating access to Niles Channel. Designed for the ultimate Florida Keys lifestyle, this property combines spacious indoor living with exceptional outdoor entertaining areas. The main home features 2 bedrooms and 2 bathrooms with an open-concept floor plan ideal for entertaining. The modern kitchen is equipped with quartz countertops, stainless steel appliances, and plenty of space for gathering with family and friends. An additional guest wing offers 3 separate bedrooms, each with its own ensuite bathroom, providing privacy and flexibility for guests or extended family. Enjoy seamless indoor-outdoor living from the large screened-in porch breezeway -- the perfect place for morning coffee, evening dinners, or relaxation. Outside, the concrete swimming pool creates a true tropical retreat, while the spacious outdoor areas offer plenty of room for entertaining. The ground level includes an expansive enclosed garage with room for multiple vehicles, storage, and all your boating and fishing gear. The fully fenced property offers abundant parking for cars, boats, RVs, and trailers, making it ideal for full-time living or a Keys getaway. Located in a quiet neighborhood, this property delivers the best of waterfront living with easy boating access, generous space, and move-in ready convenience.
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**

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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.