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$899,000
2 Beds ⋅ 1 Baths ⋅ 621091 MLS
Tropical Waterfront Living in the Florida Keys! Welcome to 24923 Park Drive in beautiful Summerland Key, where laid back Florida Keys living meets ultimate waterfront lifestyle. This charming canal-front property offers an opportunity to create your own paradise in one of the Keys' most desirable boating communities. Positioned along a wide protected canal, the property features direct waterfront access to both Ocean & Gulf, 60 ft. concrete seawall, two boat lifts, private dockage. Making it ideal for boating, fishing, kayaking, and enjoying everything the Florida Keys has to offer. The spacious large open grassy yard offers room to personalize the outside space with a pool or outdoor kitchen, tiki, fire-pit or resort style entertaining oasis. This existing home offers a wonderful opportunity for a buyer looking to renovate, expand, or create a custom island retreat. With its metal roof, single level layout, tropical surroundings and exceptional waterfront setting this property provides the perfect foundation for a Florida Keys getaway, full-time residence, or investment opportunity. Bring your vision and transform this waterfront gem into your own private Keys paradise. Florida Keys Heritage trail for biking & walking close by. Summerland Key Private Air strip walking distance away.

24923 Park Dr, Summerland
$1,300,000
2 Beds ⋅ 2 Baths ⋅ 620934 MLS
Summerland Key Cove -- Come by Sea or by Plane A unique opportunity in Summerland Key Cove offering both canal-front living and access to the community's private airport. Whether your Florida Keys lifestyle revolves around boating, flying, fishing, diving, or simply enjoying the water, this property offers a combination that is increasingly hard to find. Built in 1982, this 1,240 sq. ft. concrete block home features 2 bedrooms plus a versatile bonus room that can serve as a guest room, home office, gym, TV room, or additional living space. An approximately 400 sq. ft. screened room overlooking the canal adds substantial outdoor living space. Some major improvements have already been completed, including a 2022 metal roof, 2023 impact windows and doors on the upper level, and updated central A/C in 2020. Connected to central sewer. One of the property's standout features is the approximately 1,240 sq. ft. airplane hangar height of 9ft. Hard-to-find amenity in the Florida Keys--plus approximately 400 sq. ft. of additional storage and a concrete driveway. On the water, the property offers approximately 60 feet of concrete seawall on a 60-foot-wide canal, along with a davit. Two canal exits provide access to Kemp Channel, opening the way to both Atlantic Ocean and Gulf-side boating for fishing, diving, exploring, and enjoying the surrounding Keys waters. Located in an improved subdivision on a Tier III lot in AE-10 flood zone. Fencing is permitted. Access to the Summerland Key Cove airport and marina is available through membership. The home is currently tenant occupied with pets; advance notice is required for showings. NO tresspassing. Rented

486 S Airport Dr, Summerland
$799,000
3 Beds ⋅ 1 Baths ⋅ 620897 MLS
Welcome to the Mango Cottage on Summerland Key! Tucked away on a quiet dead-end street, this 3 bedroom, 1 bath canal front CBS home combines the laid back Florida Keys lifestyle with excellent boating access and a few features you simply don't find everywhere. Surrounded by multiple mature fruit trees, including several mango trees! This property has a distinctly tropical feel from the moment you arrive. Inside, the home offers an open floor plan, a bright kitchen with a skylight, and a spacious Florida room featuring a cool Hemingway style bar, the perfect spot to mix a drink, entertain friends, or unwind after a day on the water. An good sized laundry and utility room provides plenty of additional storage and functionality. CBS construction and a post-Irma metal roof add to the home's appeal. Out back, the pavered yard creates a low maintenance outdoor living space with plenty of room to add a pool. A 60-foot concrete dock puts your boat right outside your door, with excellent access from Summerland Key and marine fuel and ice conveniently located just down the canal. The location also puts you close to Ace Hardware, fantastic local restaurants, and everyday conveniences while still enjoying the peace of a tucked away residential dead end street. Aviation enthusiasts will appreciate the neighborhood's unique private airstrip setting, offering the potential for a true fly in/fly out Keys lifestyle. With tropical fruit trees, great boating, a concrete dock, generous outdoor space, and plenty of classic Keys character, Mango Cottage is ready for its next chapter.

27 N Lake Dr, Summerland
$2,999,000
5 Beds ⋅ 4 Baths ⋅ 620578 MLS
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

23950 Overseas Hwy, Summerland
$16,900,000
5 Beds ⋅ 4 Baths ⋅ 620413 MLS
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 with two building rights, allowing for one additional residence, surrounded by breathtaking open water views from sunrise to sunset. Designed for those who value privacy, adventure, and refined coastal living, the island features 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. The layout comfortably accommodates family and guests with an attached primary suite featuring a generous walk-in closet. A separate guest wing, accessed via a breezeway, includes its own living room, breakfast bar, and two private bedrooms. Wander the groomed trails, relax by the saltwater pool, launch kayaks from the sandy beach, enjoy pickleball, 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 sustainability and peace of mind. The purchase includes a barge, golf cart, tractor, and a private mainland lot for car storage. Howell Key offers a private island lifestyle few will ever have the opportunity to experience.

Howell Ky, Summerland
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 620321 MLS
DOUBLE the Lot. DOUBLE the Waterfront. Endless Possibilities. Positioned on a rare spacious double lot near the Summerland Key airport, this waterfront property is tailor-made for boating enthusiasts and aviation lovers alike. Featuring 120 feet of concrete seawall on a desirable flow-through canal, you'll enjoy quick access to open water and some of the Lower Keys' best fishing, diving, and cruising grounds. Afterwards, sit under the tiki and watch the world go by. The ground-level home exhibits a Keys charm with polished terrazzo floors and a relaxed, welcoming feel. Outside, ample parking provides room for boats, trailers, RVs, and guests. Inside, a unique electric train display serves as a nod to the historic Overseas Railroad that once connected the Keys. A rare opportunity to enjoy the classic Florida Keys lifestyle with room to spread out, easy boating access, and the convenience of nearby aviation amenities. Bring your big boats to this deep water canal - no bridges to the Atlantic Ocean. Plane tie downs are located in the driveway. For additional airport info - see summerlandkeyairport.com

466 W Shore Dr, Summerland
$1,185,000
3 Beds ⋅ 2 Baths ⋅ 620281 MLS
OVERSIZED GARAGE. WATERFRONT LIVING. Bring the boat, tackle, dive gear, kayaks, and all the Keys toys-there's room for everything at 706 Caribbean Drive East. With canal frontage, a 10,000-pound boat lift, and quick ocean access, this property is built for life on the water. The massive 1,188-square-foot garage below is a dream setup for serious boaters, offering space for storage, a workshop, multiple vehicles, and gear. Inside you'll love the kitchen layt up for cooking and entertaining. Hardi-board siding, new metal roof (installed in 2018), and a fenced yard complete the exterior. If you've been searching for waterfront living without sacrificing storage, this Summerland Key Cove home delivers.

706 E Caribbean Dr, Summerland
$2,246,000
3 Beds ⋅ 2 Baths ⋅ 620177 MLS
Built for the offshore lifestyle, this exceptional Summerland Key waterfront home blends luxury coastal living with the kind of boating access serious anglers dream about. Completely renovated from top to bottom, the property sits on a deep water canal with 60 feet of brand new concrete dockage and quick direct access to open water, making it ideal for larger center consoles, sportfish boats, and offshore cruising. Inside, the home was designed for relaxed Keys living with vaulted ceilings, impact windows and doors, quartz countertops, custom wood cabinetry, stainless steel appliances, and an open layout filled with natural light and canal views. The spacious primary suite is privately situated on the second floor, offering a peaceful retreat with elevated views and added separation from the guest accommodations below. The outdoor living experience is what truly sets this property apart. The waterfront pool features all brand-new equipment, including a heater and chiller, allowing for year-round enjoyment in every season. A portion of the pool area is partially covered, creating the perfect shaded outdoor lounge space after a day on the water. Covered balconies, spacious patios, and tropical landscaping give the property a true private resort feel. The custom putting green and mini golf area adds a unique touch rarely found in the Keys, creating an incredible space for entertaining guests while enjoying the waterfront setting. Whether you're heading offshore for tuna and swordfish, running to the reef, or enjoying sunset cruises through the Lower Keys, this location puts you minutes from some of the best boating and fishing in the Florida Keys. Built with durable Hardie board construction, a metal roof, impact windows and doors, covered parking, and more than 1,000 square feet of enclosed storage space underneath the home, this turnkey waterfront retreat offers the perfect balance of luxury, functionality, and the authentic Florida Keys boating lifestyle.

848 E Caribbean Dr, Summerland
$3,495,000
4 Beds ⋅ 4 Baths ⋅ 620024 MLS
OCEANFRONT, CBS, 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 or office 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

414 E Caribbean Dr, Summerland
$2,220,000
3 Beds ⋅ 2 Baths ⋅ 619294 MLS
High quality concrete 3/2 in Summerland Cove. One of the best boating communities in the lower Keys for deep water, aqua blue canal water, and oceanside access with no bridges! Brand new 60' concrete dock has just been installed. Step inside to find the fresh, modern renovation done in 2024. Featuring 3 bedrooms 2 baths with the private 3rd floor primary suite. 24'' modern white tile throughout, impact windows and doors with custom window blinds with a filtered light or privacy mode. Expansive great room with vaulted ceiling, all new recessed lighting, coastal kitchen with quartz countertops and waterfall edge. The large covered back porch overlooks the canal. Rear stairs to the custom concrete pool and 60' concrete dock. Lower storage room and covered parking. Enjoy access to world class fishing and diving sites in just minutes. Situated on a 60x100 ft lot in one of the most desirable neighborhoods in the Lower Keys.

937 Gulf Dr, Summerland
$3,995,900
5 Beds ⋅ 6 Baths ⋅ 616700 MLS
Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West. Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10' ceilings, impact glass, and abundant natural light. The chef's kitchen includes premium appliances, quartz countertops, pantry, and large island ideal for entertaining. Multiple verandas, balconies, and a rooftop observation deck deliver 360-degree sunrise and sunset views. Outdoors, enjoy your own sparkling infinity pool, expansive pool deck, and seamless flow to the water. Every residence conveys with an assigned dock space in a private boat basin featuring new composite docks with electric, water, and a fillet station--perfect for boating enthusiasts. Homes are equipped with Tesla Solar, an elevator, and generous storage. Resort-style amenities include a sport court for tennis, pickleball, and basketball, along with oceanfront lounge areas, hammocks, and opportunities for paddleboarding and kayaking. Just one block from a private airport, accessibility is unmatched. For investors, Seven Palms Cove is an exceptional opportunity: there are no rental restrictions, and nearby comparable properties generate over $300,000 annually. Whether as a forever home, luxury vacation retreat, or high-performing investment, Seven Palms Cove offers the perfect blend of exclusivity, comfort, and opportunity in the Florida Keys.

231 E Shore Dr Unit 1, Summerland
$4,375,000
5 Beds ⋅ 6 Baths ⋅ 616703 MLS
Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West. Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10' ceilings, impact glass, and abundant natural light. The chef's kitchen includes premium appliances, quartz countertops, pantry, and large island ideal for entertaining. Multiple verandas, balconies, and a rooftop observation deck deliver 360-degree sunrise and sunset views. Outdoors, enjoy your own sparkling infinity pool, expansive pool deck, and seamless flow to the water. Every residence conveys with an assigned dock space in a private boat basin featuring new composite docks with electric, water, and a fillet station—perfect for boating enthusiasts. Homes are equipped with Tesla Solar, an elevator, and generous storage. Resort-style amenities include a sport court for tennis, pickleball, and basketball, along with oceanfront lounge areas, hammocks, and opportunities for paddleboarding and kayaking. Just one block from a private airport, accessibility is unmatched. For investors, Seven Palms Cove is an exceptional opportunity: there are no rental restrictions, and nearby comparable properties generate over $300,000 annually. Whether as a forever home, luxury vacation retreat, or high-performing investment, Seven Palms Cove offers the perfect blend of exclusivity, comfort, and opportunity in the Florida Keys.

231 E Shore Dr Unit 4, Summerland
$4,400,000
5 Beds ⋅ 6 Baths ⋅ 616705 MLS
Introducing Seven Palms Cove, a one-of-a-kind new construction community redefining luxury island living in the Florida Keys. With only seven exclusive oceanfront residences starting at $4M, this private, gated enclave offers an extraordinary opportunity to own a slice of paradise just minutes from Key West. Each home spans over 4,000 sq. ft. with 5 bedrooms, 5.5 bathrooms, and open-concept layouts with 10' ceilings, impact glass, and abundant natural light. The chef's kitchen includes premium appliances, quartz countertops, pantry, and large island ideal for entertaining. Multiple verandas, balconies, and a rooftop observation deck deliver 360-degree sunrise and sunset views. Outdoors, enjoy your own sparkling infinity pool, expansive pool deck, and seamless flow to the water. Every residence conveys with an assigned dock space in a private boat basin featuring new composite docks with electric, water, and a fillet station—perfect for boating enthusiasts. Homes are equipped with Tesla Solar, an elevator, and generous storage. Resort-style amenities include a sport court for tennis, pickleball, and basketball, along with oceanfront lounge areas, hammocks, and opportunities for paddleboarding and kayaking. Just one block from a private airport, accessibility is unmatched. For investors, Seven Palms Cove is an exceptional opportunity: there are no rental restrictions, and nearby comparable properties generate over $300,000 annually. Whether as a forever home, luxury vacation retreat, or high-performing investment, Seven Palms Cove offers the perfect blend of exclusivity, comfort, and opportunity in the Florida Keys.

231 E Shore Dr Unit 6, Summerland
$950,000
3 Beds ⋅ 2 Baths ⋅ 617590 MLS
Hard to find a home in a Park like setting with a boat ramp right out the back door! 3 bedrooms 2 full baths and open living space. Summerland key cove is just 25 miles from Key West. Great place to raise a family or to retire. Be it you're a boater, pilot, fisherman or just want the open space to walk and enjoy privacy of the park. This quit Island neighborhood offers rare access to the laid-back Florida Keys. There is a possibility of being able to convert the lower level into an in-law apartment. This home has deeded reserved exclusive rights to the Park, Boat ramp and Pond PLEASE NOTE! OWNER FINANCING POSSIBLE!

24840 Park Dr, Summerland