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Summerland Key Homes for Sale, Single Family Houses, MLS Home Listings

Total Listings 26
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$2,599,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
3 Bed, 3 Baths, 1,792 SqFt Days Listed: 120
-3.71% ($100,000) 1 Price Change : Last Change 7 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Boat Ramp

Spectacular Open Ocean Views Across from Open Water! Rare opportunity to own this coastal jewel located on the most prestigious and sought-after Flagship Drive in the exclusive Summerland Cove Isle neighborhood on Summerland Key. This beautifully designed CBS 3-bedroom, 2-bathroom canal-front pool home offers breathtaking, unobstructed open ocean views that will captivate you from sunrise to sunset. Situated on an oversized 10,080 sq. ft. lot, larger than most in the area, this waterfront retreat is perfectly positioned across from open water, allowing you to enjoy mesmerizing sunset cocktails from the open deck with panoramic sunset views in one direction and exquisite moonrises in the other--all in one evening. The property boasts a concrete dock, a boat ramp for launching jet skis, small boats, paddleboards, and kayaks, as well as two boat lifts each 14k lb on a, deep, flow-through canal with quick and easy deep-water access to the Atlantic Ocean--a true boaters dream. Inside, the home features a modern coastal feel, inviting open-plan living, dining, and kitchen area with soaring vaulted ceilings, creating an airy and light-filled atmosphere. The split floor plan offers privacy, with the primary suite situated in a separate wing. This serene retreat also includes a flexible bonus space that can be closed off and used as a sitting area, office, gym, or nursery, with access to a covered deck. The exterior is equally impressive, featuring a sparkling concrete pool with canal-front views, a garage within a 1088 sqft storage area, and a carport offering ample space for boat storage or the option to transform it into a spacious covered entertaining area. Located near a local airstrip for small planes, this rare property is a haven for those seeking both luxury and convenience in a prime Keys location.Dont miss this rare opportunity to own a coastal jewel with ocean views and deep-water boating access. Insurances $12k Video https://tinyurl.com/4ff3aan8

$2,895,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
4 Bed, 4 Baths, 2,416 SqFt Days Listed: 142
-3.02% ($90,000) 1 Price Change : Last Change 37 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.

EXQUISITE WATERFRONT property in Summerland Cove Isles, an upscale 4 bedroom 3 1/2 bath home with an elevator and roof top terrace! This stunning concrete block home offers the perfect blend of modern design and coastal flair, situated on a desirable flow-through canal. Direct access to both the Atlantic Ocean and Gulf make this ideal for boating and water enthusiasts.As you step inside, youre greeted by high-end finishes that elevate the space. The open-concept living area is flooded in natural light with access to balconies on every level. The gourmet kitchen is a chefs dream, with top-of-the-line appliances, custom cabinetry, and a large center island--perfect for entertaining. Step outside to your tropical oasis, where youll find a sparkling pool and heated jacuzzi--perfect for enjoying Floridas year-round sunshine and balmy evenings. The expansive patio offers plenty of space for lounging or alfresco dining, all while overlooking the canal. For the boating enthusiast, the property features a private 60 dock with a 20,000 pound boatlift affording easy access to the open water, whether youre heading out for a day of fishing on the Gulf or a sunset cruise on the Atlantic. A commercial ice-machine completes the package in the downstairs storage room. The homes thoughtful design also includes a rooftop terrace that offers panoramic views of the surrounding waters and natural beauty--ideal for enjoying the sunset, stargazing, or simply relaxing with a glass of wine. Take the elevator to the top floor and catch exceptional views of Niles Channel Bridge and the ocean.This home is the epitome of luxury coastal living, offering elegance, and unparalleled access to the best of the Keys. Escape to your personal oasis and take this opportunity to create lasting memories.

$3,500,000
Summerland Key
Summerland Beach   - MM: 25.00
7 Bed, 7 Baths, 4,531 SqFt Days Listed: 132
-29.29% ($1,450,000) 3 Price Changes : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Basin,Boat Li

SELLER FINANCING AVAILABLE! Paradise awaits at this breathtaking 7-bedroom, 6-bathroom waterfront estate in Summerland Key! Designed for those who crave Florida Keys luxury, privacy, and endless outdoor adventure, this resort-style retreat offers breathtaking open-water views, a private boat basin, and an array of high-end amenities--all just moments from exclusive Little Palm Island.Spanning 4,531 sq ft, (12,603 sq ft gross) the main house showcases soaring cathedral cedar ceilings, expansive ocean views, and an open-concept design that seamlessly blends indoor and outdoor living. The primary suite on the top floor offers a spa-like shower with ocean views, while the lower level features two guest bedrooms, a full bath, a kitchenette, and a cozy living space overlooking the pool.For guests or multi-generational living, two attached cottages each feature two bedrooms, one bath, and private balconies. A widows peak lounge above one cottage provides panoramic ocean views, perfect for sunrise coffee or sunset cocktails.Immerse yourself in Florida Keys paradise:** 3-tier heated & cooled pool, screened for year-round enjoyment.**Private covered boat basin & lift, ideal for boating enthusiasts.** Expansive waterfront decks, a tiki hut, and shuffleboard court for endless entertainment.** Home gym with ocean views, gated entry, covered carports, garage, and ample parking.Upgraded with new impact windows & doors and new mini-splits throughout, this home offers modern comforts with unparalleled luxury and privacy.This is a rare opportunity --to own a resort style property and experience the ultimate Florida Keys lifestyle.Per seller: Draft is at 4 right at entrance at low tide, then gets deeper (8-9) closer to the house. High tide is approx 6 at entrance, and 10 in the middle. Boats can be docked on the dock in front of basin. Please note: Property is a monthly rental and heavily rented. Please do not attempt to walk the property.

$5,500,000
Summerland Key
Summerland Estates   - MM: 25.00
3 Bed, 3 Baths, 2,088 SqFt Days Listed: 183
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 180ft.

Exceptional Investment Opportunity in the Lower Florida Keys!Owner and private financing are available. This is one of the very few vacation rental properties licensed for daily, weekly, or monthly rentals. Boasting an impressive occupancy rate and generating up to $400,000 annually, this property offers stress-free, passive income in Summerland Key, a premier location.Discover a rare gem in the heart of the Lower Keys! Recently remodeled to perfection, this luxurious three-bedroom beach house includes a sunroom with a palatial ocean view, currently used as a fourth bedroom. Just 20 miles from vibrant Key West, this coastal retreat features a private natural beach, breathtaking ocean views, and access to a private airport for island residents less than two blocks from the property.Dont miss this unparalleled investment opportunity!Please note that I have a personal interest in this property.

$5,600,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
4 Bed, 4 Baths, 5,608 SqFt Days Listed: 1152
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,BasinConcr

Spectacular Open Water location, with fabulous views from this well-built Oceanfront concrete home. Direct Ocean access from the step down concrete seawall/dock that wraps around the waterside of the property, including the boat basin with two boat lifts and a fish cleaning station. Relax in large pool with over-spill hot tub & a big pool patio area and a covered patio for entertaining, which drinks in the Ocean view. Interior features abound: wood cabinetry, granite, marble, and more. Double bronze doors adorn the entrance and foyer. There is a formal dining room off the kitchen. The master bedroom opens onto a porch, facing the Ocean. Soaring ceilings in the living room, with Casablanca style rotating fans. The upstairs level has a lovely deck that faces the Ocean, perfect to relax, enjoy the sunsets, and where you can see for miles and miles. Gated and fenced.

$8,955,000
Summerland Key
Summerland Beach   - MM: 25.00
5 Bed, 5 Baths, 3,952 SqFt Days Listed: 266
+12.01% ($960,000) 1 Price Change : Last Change 44 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Basin

TROPHY OCEANFRONT ESTATE! This one-of-a-kind luxury estate offers an unparalleled coastal lifestyle on 120 feet of prime oceanfront. Designed for the discerning buyer, this breathtaking property combines elegance with the ultimate boating experience.The centerpiece of this estate is the 120,000 lb boat lift, capable of accommodating a 70 ft yacht--a rare find in the Keys. The property also features a private mooring buoy, 2 additional boat lifts, and a private boat basin equipped with a compressor-operated bubbler system to keep seaweed at bay. With exclusive bay bottom rights, its a true boaters paradise, offering the perfect space to keep your vessels safe. Inside, the estate is a showcase of luxury. It features 5 spacious bedrooms, an exercise room, 4 full baths, and 2 half baths, all thoughtfully designed for comfort and style. The main living area boasts vaulted ceilings and opens onto a massive tiled patio surrounding a raised pool and spa. This elevated design allows for a seamless flow between indoor and outdoor living, complete with a covered bar area for entertaining and breathtaking panoramic views of the Atlantic Ocean and Little Palm Island.The chefs kitchen is equipped with high-end appliances and an open layout, perfect for grand gatherings. A separate dining area is adjacent to the kitchen and living area. There is a laundry room and the 5th bedroom is currently set up as an office for added flexibility. The single-car garage provides peace of mind for your vehicle, large storage area under the house.Set on an expansive 37,400 sq. ft. lot, this estate is beautifully landscaped, resembling a resort with lush tropical gardens. A desalination plant and backup generator ensure complete self-sufficiency, while the private beach offers your own slice of paradise. This is a trophy property with unmatched boating capabilities and luxurious living. Dont miss your chance! Schedule your private tour today! Video tour https://tinyurl.com/1151Ocean

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 06-15-2025.
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