Divider
Content Divider

Summerland Key Waterfront Homes For Sale on the Ocean Side of the Island. Oceanfront Homes

Total Listings 26
Order By:

$3,899,000
Summerland Key
Summerland Estates   - MM: 25.00
5 Bed, 5 Baths, 3,119 SqFt Days Listed: 283
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Basin

Oceanfront, New Construction home in the exclusive Residences at Summerland Key community, where weekly rentals are allowed! This new, gated development boasts a private boat basin which will feature a new composite dock with electric, water and fillet station for easy and frequent boating, with an assigned dock space to convey with home purchase! The home is a two-story, Oceanfront paradise, intuitively designed with entertaining in mind. A bright and spacious open-concept floor plan features 10 high ceilings, impact windows and loads of natural light. Equipped for culinary pursuits, the stunning Chefs Kitchen features a premium appliance package, quartz countertops, pantry, and large island with seating. Plenty of room for family and guests with 5 spacious bedrooms and 5.5 Bathrooms. An expansive back veranda is accessed through the Great Room, an ideal spot for enjoying morning coffee while taking in the prevailing sea breezes. Steps from the veranda is a large pool deck and sparkling infinity pool; cool off after a day on the water in this backyard oasis! Enjoy year-round sunshine from any of 3 decks totaling over 325 Sq. Ft. each, including a rooftop observation deck offering 360-degree views of Open Water, Sunrises and Sunsets! As an added bonus, the home comes equipped with Tesla Solar, elevator, and 296 Sq. Ft. of downstairs storage. This turn-key, home is designed for elevated seaside living. Enjoy resort-style amenities, this well-appointed community will come equipped with a shared Sport Court for tennis, pickleball, and basketball. Lounge in a hammock by the Oceanside, or enjoy year-round sunshine via kayaks, canoes and paddleboards, this well-equipped development offers move-in ready Keys living. Just minutes from shops and restaurants in town, but nestled within a quiet, gated community, this enviable location offers peace, relaxation, and convenient proximity to town! ACT NOW, home prices likely to increase as units are sold!

$4,445,000
Summerland Key
Summerland Beach   - MM: 25.00
7 Bed, 7 Baths, 4,531 SqFt Days Listed: 24
-10.20% ($505,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Basin,Boat Li

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, 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.Step outside and 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. Schedule your private tour.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: 75
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: 1044
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.

$6,249,000
Summerland Key
Summerland Key Cove   - MM: 25.00
6 Bed, 6 Baths, 4,981 SqFt Days Listed: 84
-3.71% ($241,000) 1 Price Change : Last Change 10 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Experience unparalleled luxury in this Brand New 2025 Custom Built Smart Home. 6,128 SQ FT concrete-constructed oceanfront home, situated in prestigious Summerland Key. With 90 feet of ocean frontage and breathtaking southwest views of the Atlantic Ocean, this home is the ultimate retreat for those seeking elegance, comfort, and adventure.The third floor is the heart of this home, featuring an infinity-edge pool and spa that frame magnificent sunsets and ocean vistas. Seamlessly blending indoor and outdoor living, the expansive entertainment areas promise unforgettable gatherings. This magnificent custom home offers six spacious bedrooms with ensuite bathrooms, including a dual primary suite that can serve as two bedrooms or a private suite with an office. Additional features include: A state-of-the-art sound proof home theater room with Marantz 11.2 surround sound, 16 screen, and 8K JVC projector.Custom Canadian birch cabinetry and Thermador WiFi-enabled appliances throughout. A boaters Paradise
 designed for water enthusiasts, the property features: Two boat lifts (25,000 LB and 10,000 LB), A 6 x 90 concrete dock with two tiers for jet skis and kayaks. Deepwater access with a 90 wide, 28 deep channel leading directly to the Atlantic and Gulf.Proximity to world-class snorkeling and diving at Looe Key Coral Reef.Unmatched durability and sustanibility, built to exceed 180 MPH wind loads, solid concrete floors, walls & roof.This home includes: All high-impact Marvin & Euro-Wall windows and doors.70 solar panels (34.5 KW of power) and 4 Tesla Power Walls 57.6KW powers home.Three on-demand hot water systems and a 10,000-gallon rainwater cistern.Exceptional features include; Private elevator servicing all three levels. RV/Boat garage (15 W x 50 D x 14 H) with 50 AMP/220V service. Tesla charging station. WiFi-enabled smart home systems, including AC, pool pumps, and appliances. See Documents Tab / Possible Seller Financing.

$8,955,000
Summerland Key
Summerland Beach   - MM: 25.00
5 Bed, 5 Baths, 3,952 SqFt Days Listed: 158
+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 02-27-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA