Summerland Key Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Waterfront homes for sale in Summerland Key are spectacular pieces of Florida Keys real estate.  With a location just a quick 20 minute drive from exciting Key West, residents of Summerland Key houses have easy access to some of the best locales in the Florida Keys.  With this leisure and convenience destination so close, Summerland Key itself is a secluded and tranquil enclave of spectacular real estate.  Waterfront properties in Summerland Key make up the majority of the market, and include Summerland Key oceanfront homes and bayfront properties.  Browse the Florida Keys MLS for all waterfront homes in Summerland Key.

Total Listings 31
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24943  Park Drive  For Sale, MLS 585694
$465,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,128 SqFt Days Listed: 329
-2.11% ($10,000) 2 Price Changes : Last Change 61 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

Charming waterfront conch cottage on one of the best canal systems in the Lower Keys. 60 of water frontage and a concrete seawall on a deep draft flow through canal system just minutes to the open water. Fenced and gated with a boat lift! CBS/combo construction and metal roof with large glass doors for natural light and a gorgeous outdoor shower you will use every day! The interior, pure Key West charm. Soft romantic gray tones, with bead board and chair rail accents. Tile floors enhance the entire home. The new kitchen is a chefs dream with stainless steel appliances, granite counters, subway tile back splash, new kitchen cabinets and dramatic focal point tile accent pattern. Close to shopping and restaurants

128 W Shore Drive  For Sale, MLS 589150
$499,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,008 SqFt Days Listed: 86
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.

Captains and Pilots wanted at this waterfront home just yards from the Summerland Key airstrip on Summerland Key. Park your plane in front of your home and dock your boat at your 60 concrete dock with boat lift and deep draft access to the ocean on a 57 wide canal with no bridges to go under. The 3 Bedroom concrete homes offers newly polished Terrazzo floors, Hurricane impact doors and windows and metal roof. The colossal back back yard is the perfect place to entertain friends and family complete with a covered pavilion looking out to picturesque water views. World class fishing and diving are just minutes away and just 30 minutes to the magic of Key West.

868 E Caribbean Drive  For Sale, MLS 589593
$550,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 884 SqFt Days Listed: 65
-4.35% ($25,000) 1 Price Change : Last Change 14 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.

Looking for a canal front home with superior boating in Summerland Key Cove? This is it Youll love the flow through canals with 60 of concrete seawall and a boat lift.Fenced yard and nicely landscaped. CBS home with metal roof, granite kitchen counter tops, tiled floors - easy to maintain. Storage shed. One of the least expensive canal fronts in Summerland Key Cove.

960  Caribbean Drive  For Sale, MLS 589115
$595,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,280 SqFt Days Listed: 88
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat RampConcrete

Summerland Key opportunity! Enjoy world-class fishing and diving while living on a beautiful flow-through canal with your own boat ramp, concrete seawall and swimming pool. Situated on an extra deep, 60 x 125 ft. lot, the 2BD/2BA home features a split-bedroom floor plan, new metal roof in 2018, and is hooked up to the sewer. Current owners have enjoyed it for years, now its time for new owners to add personal touches and updates. Not ready to make the permanent move yet? This property has terrific potential as a vacation rental or long term rental. Make it yours! Owner-occupied, 24 hours notice to show.

867  Caribbean Drive  For Sale, MLS 590124
$647,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,032 SqFt Days Listed: 35
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

This home is the essence of Keys living. Home shows beautifully with open floor plan and large porch that overlooks the flow through, wide canal system filled with tropical fish. Lobster and a variety of marine life. Excellent boating, just minutes to the Atlantic and Gulf. Low maintenance pea rock yard and concrete seawall with boat lift make your water adventures easy-going. Spacious waterfront porch is the perfect spot for relaxing after a long successful day on the water. Large side yard accommodates an RV with 50 amp. service. Encounter the amazing sea life in your tropical aquarium right in your backyard. A short walk or bike right leads to shops and some of the best restaurants in the lower Keys. This home is move-in ready and the perfect place to begin your Keys adventure!

549 E Caribbean Drive  For Sale, MLS 587442
$675,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,280 SqFt Days Listed: 199
-3.43% ($24,000) 3 Price Changes : Last Change 49 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 30ft.Concrete

Beautiful, Brand new 3 bedroom 2 bath Canal home with covered rear porch on a deep, wide canal with incredible boating access. Summerland Cove is known for exceptional boating. The deep flow through canal is a beautiful aqua color. Located on the ocean side of Summerland Key at mile marker 24. The lot is 60 x 100 with 60 canalfront, 30 concrete dock For your boat with steps down to the water for easy access to kayaking and paddle boarding. Built to the high standards for Monore County, this is rated for 180 mph, has impact windows and doors, and hardi plank siding and metal roof. Modern interior features 9 ceilings, laminate floors, quartz countertops and stainless appliance package. Includes lower enclosure storage.

969 E Caribbean Drive  For Sale, MLS 590362
$689,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,250 SqFt Days Listed: 19
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.

New metal roof + new seamless gutters, canal front 2 bedroom 2 bath home Ready to start enjoying Life in the Florida Keys? This turn key opportunity will make that easy for you, its in great condition and is offered almost fully furnished! This 2 bedrooms and 2 bath home has island character with an open, great room living/dining/ kitchen and high, wood lined ceilings. Beautiful porch overlooks the aqua canal and on site 60 seawall. Premier boating access from this oceanside, deep water community know for its clean, deep water canal. This is the best priced single family in this high demand community! Legal storage room downstairs

637 E Caribbean Drive  For Sale, MLS 589981
$699,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,040 SqFt Days Listed: 44
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift30ft.

If you are looking for a beach home that is in move-in condition, then look no further! Meticulously remodeled and maintained - stainless appliances, a Viking oven, glass backsplash, covered porch, downstairs storage, and a new metal roof. Situated on one of the premium canals in the Lower Keys. 10,000 lb boat lift - flow through canal, and quick boating access to the Atlantic or Gulf. Launch your kayaks from your dock or swing on the hammock. Just pack your fishing rod and tooth brush.

24449  Caribbean Drive  For Sale, MLS 585169
$700,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,296 SqFt Days Listed: 364
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

Charming custom built, waterfront home in a multi-million dollar neighborhood! One of the lowest priced home, surrounded by million dollar estate properties. This coastal cottage home has rich wood cathedral ceilings, enhanced by wood floors and opens to a water side deck directly off the living room. The captivating Atlantic Ocean and gorgeous sunsets can be seen from the upstairs master suite. The home features a metal roof, new exterior paint and new siding, 12,000 lb. boat lift, concrete seawall, privacy fencing, tropical landscaping & high clearance covered parking. The deep draft boating water allows larger boats quick access to both the Atlantic and Gulf of Mexico. Just minutes to world class fishing & diving.

845  Gulf Drive  For Sale, MLS 588935
$725,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 97
-5.84% ($45,000) 2 Price Changes : Last Change 53 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.Concrete

Great location for this perfect move-in-ready poured concrete custom waterfront home with impact windows and doors, metal roof and excellent deep water boating. This sailboat friendly home features tile throughout, updated kitchen with granite and stainless appliances. Awesome screened-in deck overlooking the beautiful clear waters of the Isles Subdivision. Numerous outside entertaining areas for relaxing and socializing. Plenty of privacy with no one directly across the canal or to the left. And for your boating needs, 60 feet of concrete dockage with a boat lift, metal entry ladder, and fish cleaning station. Everything is ready for you to move in and start enjoying the fabulous Florida Keys lifestyle.

544 W Shore Drive  For Sale, MLS 590341
$735,000
Summerland Key
Summerland Key Cove   - MM: 25.00
4 Bed, 4 Baths, 1,646 SqFt Days Listed: 21
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 120ft.Concrete

This property offers the buyer a beautifully landscaped mini sanctuary for privacy on a double lot with easy ocean access for a large sport fishing boat or a large shallow draft sailboat. You have plenty of room for your water toys and boats with 120 of dockage with 30 amp dockside service, and a 7500 lb. boat lift on a flow through canal. This clean canal is your summer time swimming pool. All kinds of sea life can be seen from the dock including, Snapper, Sargents Major, French Angels, Parrotfish, Spiny lobsters, and Manatees. The surrounding Keys offer snorkeling, scuba diving, deep sea fishing, flats fishing, kayaking, bird watching and more. For pilots, there is an airstrip down the street and the street has 50 easement setbacks so planes can be moved down the street

442 W Shore Drive  For Sale, MLS 590335
$897,500
Summerland Key
Summerland Key Cove   - MM: 25.00
4 Bed, 4 Baths, 1,345 SqFt Days Listed: 21
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift120ft.Concr

Spacious concrete home on double lot in Summerland Key with excellent deep water boating. 120 concrete seawall with 12,000 lb boatlift. No bridges to restrict access to open water. Inside, attention to detail was not spared in the beautiful renovation of this home. Tile floors throughout, granite countertops and stainless steel appliances. 6 privacy fence corner to corner. Metal roof and garage.

1167  Flagship Drive  For Sale, MLS 590299
$900,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
3 Bed, 3 Baths, 1,200 SqFt Days Listed: 23
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Fantastic location on a corner canal lot one property in from the ocean in Summerland Cove Isles. Excellent deep draft dockage with concrete dock and approximately 185 of waterfront with immediate ocean access. The 3 Bedroom 2 Bath home offers beautiful wood flooring throughout and is highlighted by picture perfect views of the mangrove islands in the salt water lagoons. The 9,000 sq. ft. lot offers plenty of room for pool, RV, and boat trailers plus in the large 1 car garage.

1121  Ocean Drive  For Sale, MLS 582802
$939,000
Summerland Key
Summerland Beach   - MM: 25.00
2 Bed, 2 Baths, 2,304 SqFt Days Listed: 512
-26.35% ($336,000) 3 Price Changes : Last Change 61 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp

Enjoy tranquil breezes and panoramic views of the Atlantic Ocean from this ocean front home. Some of the best boating the Keys have to offer is right out your back door with quick access to Looe Key reef and deep water fishing making it a boaters delight. The concrete boat ramp makes launching your jet skis, canoes or paddle boards a cinch.The home is situated on more than a quarter acre of property offering plenty of room to add your outdoor amenities. Custom finishes throughout this one owner home makes it a unique piece of paradise.

950  Bay Drive  For Sale, MLS 585204
$1,049,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
3 Bed, 3 Baths, 2,467 SqFt Days Listed: 361
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

This completely custom 3 Bedroom 3.5 Bath home, designed by the owners, sits on elevated land in Summerland Cove Isles, an upscale coastal community of waterfront homes on crystal clear 50 wide flow-through canals. Enter into the 2-story Great Room boasting soaring tongue-in-groove ceilings, exquisite rock and black pecky cypress accent walls, a loft study, adjoining Entertainment area, and lots of glass looking out to the water. The large Chefs Kitchen features a center tumbled marble dining island, custom wood cabinetry and stainless gas stove and appliances. You will want to retire in the colossal Master Suite, also enhanced with beautiful tongue-in-groove ceilings, where you can relax in the large soaking spa tub. Guests will enjoy their privacy in the entire 1st floor Guest

296  Caribbean Drive  For Sale, MLS 583618
$1,100,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,288 SqFt Days Listed: 455
-7.95% ($95,000) 2 Price Changes : Last Change 91 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davit Pads,DavitsCon

Meticulously maintained Oceanfront CBS home boasts flawless & unobstructed ocean views from nearly every room of this immaculate home. Enjoy world class fishing at your back door with quick access to a deep marked channel to the Atlantic Ocean and Gulf of Mexico. Youll appreciate the beautiful concrete seawall, outdoor shower, downstairs storage, paver driveway, fenced yard and spacious outdoor living area, which has been lovingly maintained. Magnificent sunsets can be viewed in the privacy of the oceanfront screened porch. Includes an easy living open floor plan with a gourmet kitchen, all new stainless appliances (3 year warranty), tile floors, new roof. Offered furnished

16 S Airport Drive  For Sale, MLS 590343
$1,150,000
Summerland Key
Summerland Key Cove   - MM: 25.00
4 Bed, 4 Baths, 1,824 SqFt Days Listed: 21
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

CBS structure, situated on a 17.5K sq.ft. point lot in an exclusive fly-in community in Summerland, This solidly built home, built in 1958 by the Toppinos, has served only a handful of owners, whove maintained it in excellent condition. The home boasts four bedrooms, with 2 1/2 baths, tile flooring throughout, varnished, stained pine planked, vaulted ceilings, with ceiling fans. Hurricane shutters for the entire home.Home constructed of both solid, poured concrete walls, and block walls throughout interior and exterior.

280 E Caribbean Drive  For Sale, MLS 587066
$1,200,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 231
-14.29% ($200,000) 1 Price Change : Last Change 80 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Ramp83ft.

Location, location, location. This is a double, open water lot that is a true piece of paradise offering deep water boating, great dockage and expansive open water views in prestigious Summerland Key Cove. The property has a pull-thru boat house and boat ramp, seawall dockage and a cut-in boat slip to accommodate all of your boats and watercraft. With the double lots you have plenty of space for a pool, entertaining or home expansion where you will enjoy the sunsets and endless ocean views that mainlanders only dream of.

25361  1St Street  For Sale, MLS 588349
$1,298,000
Summerland Key
Summerland Beach   - MM: 25.00
3 Bed, 3 Baths, 2,535 SqFt Days Listed: 139
-5.81% ($80,000) 1 Price Change : Last Change 86 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Summerland Key Beach ocean front jewel.Deep water boating access!! A concrete fortress built to last the test of time.3 bed/3 bath 3 level home. Custom master suite and bath on top floor with over a 1000 s.q. ft. of space. 650 s.f. of double covered decks overlooking Niles Channel tropical sun & moonrises.Sandy beach for easy access for all of your water sport activities. 2 car garage for plenty of storage. Owner will consider purchase money mortgage with 50% down. Owner is licensed Florida REALTOR

586 E Caribbean Drive  For Sale, MLS 588063
$1,349,500
Summerland Key
Summerland Key Cove   - MM: 25.00
5 Bed, 5 Baths, 3,651 SqFt Days Listed: 156
-3.57% ($50,000) 1 Price Change : Last Change 77 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Davits118f

VIEWS! 118 ft. of canal front with good boating access. Concrete seawall & concrete dock with step down. boat davit and boat lift. Unique architecture. Custom built. 3 Bed/2.5 Bath Upstairs, built in 1994 is 2412 sq. ft. plus 470 sq. ft. screen porch with Open Water views. Open floor plan with vaulted ceiling and tile floors Downstairs, is a separate (1239 sq. ft.), 2bd./ 1bth with 2nd kitchen is the original house 1977 is plus 752 sq. ft. covered porch. Split bedroom floor plan up & down. Lower level sits at 8.1ft above sea level. AE flood Zone. House is a single family home, not a duplex. Vacant lot next door. Carport and Garage. Room for a pool. Airport access and parking available for a membership/fee. Desirable Summerland Key, Fl Google map https://goo.gl/maps/3GWjX25v

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 04-08-2020.

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