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 26
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24943  Park Drive  For Sale, MLS 585694
$475,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,128 SqFt Days Listed: 94
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

Lot 1  Overseas Highway  For Sale, MLS 582561
$589,000
Summerland Key
Summerland Key Cove   - MM: 25.00
1 Bed, 1 Baths, 768 SqFt Days Listed: 290
-1.67% ($10,000) 1 Price Change : Last Change 139 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Beautiful ocean views from this cozy fishing cottage located in the heart of Summerland Key! Step inside the 1 bedroom 1 bathroom Cottage and enjoy soaring wood beam ceilings, a spacious great room, and gorgeous wide open Ocean views from every angle. A fishermans paradise with great deep draft dockage, concrete dock, boat lift, and an additional 768 sq ft storage room below the home. World-class fishing and diving are just minutes away as well as the magic of Key West

24743  Park Drive  For Sale, MLS 584096
$639,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,223 SqFt Days Listed: 195
-5.33% ($36,000) 3 Price Changes : Last Change 33 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Summerland Key Cove airport section of Summerland Key is where this concrete fortress is located. CBS construction with poured decks and roof, impact windows and doors, make this home a storm bunker. Open floor plan on a deep flow thru canal is a boaters paradise. Tile floors and granite tops, new central A/C, new 16000lbs boat lift.

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: 129
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.

877  Bay Drive  For Sale, MLS 582866
$720,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
3 Bed, 3 Baths, 1,300 SqFt Days Listed: 272
+3.15% ($22,000) 1 Price Change : Last Change 17 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davit Pads,DavitsCon

Soothing setting in prestigious Summerland Isles, located on a wide, deep draft canal with quick access to both the Atlantic and Gulf of Mexico. Concrete/CBS construction with gorgeous renovations including a new metal roof, new hurricane rated windows and sliding doors, newly renovated bathrooms, new kitchen appliances, new tile floors, vaulted ceilings with recessed lighting, soothing interior tropical colored paint, large baseboards, waterside screened porch, step down concrete seawall, Tiki hut, davits, new pea rock, new railings, and large downstairs storage area.

473  Caribbean Drive  For Sale, MLS 585263
$749,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,320 SqFt Days Listed: 122
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

Affinity modular home coming soon! This is your chance to customize your dream home. 60 foot concrete seawall and boat lift! Stainless steel appliances, wood cabinets, granite counter tops, crown molding, 9 foot ceilings, granite vanity tops in both master and guest bathroom, metal roof, impact resistant doors and windows, downstairs enclosure and many more upgrades!Pictures are of model home. Ask today about touring our model home!

845  Gulf Drive  For Sale, MLS 586478
$795,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 35
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.Concre

All that you could want! Neat as a pin and move-in-ready concrete block 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.

656 W Shore Drive  For Sale, MLS 585859
$799,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,748 SqFt Days Listed: 83
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Make this your Vacation Home or Investment property on Summerland Key! True custom built home by Tom Ryan. Enjoy the main home which has 2 bedrooms and 2 baths and also a wonderful Guest house with 1 bedroom, 1 bath. Impeccably maintained. 100 of canal frontage - flow through canals and big boats are welcome. Open floor plan with Quartz kitchen countertops, all new stainless kitchen appliances, 3 AC units to cool the house in zones. This home is concrete block with a metal roof for easy maintenance. Minutes by boat to the Atlantic or Gulf. 10,000 square foot lot with a garage and plenty of room to park an RV or boat trailers. Soak in the great outdoors beneath the mature shady trees. Plenty of room for a pool and tiki.

24394  W  Caribbean  Drive   For Sale, MLS 585382
$889,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 114
-1.11% ($10,000) 1 Price Change : Last Change 28 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat RampConcrete

Magnificent Oceanfront Location. Pre-Firm Concrete Home With A Large Storage Area Below. Sunsets & Excellent Boating with full seawall and boat ramp. House features a spacious screened porch, Terrazzo flooring throughout....open floor plan with bedrooms & baths on each end....Wake up to Ocean Views... All hooked up to sewer. Buildable Canal Lot across the street has a 60 foot seawall with protected dockage and easy ocean access. Available for sale at additional $249,000.

1055  Flagship Drive  For Sale, MLS 583893
$999,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
3 Bed, 3 Baths, 1,836 SqFt Days Listed: 206
-9.10% ($100,000) 3 Price Changes : Last Change 40 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Immediate Ocean Access from this 2-Story Concrete fortress located on a 10,000 sq. ft. lot in Summerland Cove Isles. Built by local builder Tom Ryan, this 3 BR home boasts an open floor plan highlighted by a retracting wall of glass that opens to the full length porch overlooking the water. The 2nd Story Master BR is complete w/large Bath and views of the ocean. A 3rd-Story Loft is ideal for taking in world-famous Keys sunsets over the ocean. The 100 concrete dock offers deep draft dockage and is just minutes away from world-class fishing and diving off of Looe Key. After a day on the water enjoy al-fresco dining under you waterfront pavilion. The 2-car garage allows for plenty of storage for all of your toys. A full house generator & easy maintenance yard complete this wonderful home!

24245 W Caribbean Drive  For Sale, MLS 586998
$1,120,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 2,422 SqFt Days Listed: 2
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

After a day of world class fishing and diving, dock your boat on one of the two boat lifts and relax in your resort style pool/spa and tiki hut! Custom built 3bd/3ba waterfront gated home offers exceptional craftsmanship throughout. Chefs kitchen, wood flooring, plantation shutters, 9ft. ceilings with crown moulding and private master suite with picturesque ocean views are just some of the interior features. Over sized garage offers extended entertaining space with an abundance of storage. Concrete pool surrounded by flagstone decking and mature landscaping make this prestigious Summerland Key Cove home perfect for yearly living or a spectacular vacation retreat!

24318 W Caribbean Drive  For Sale, MLS 586526
$1,127,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,713 SqFt Days Listed: 32
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat RampConcrete

True Oceanfront Gem!! This home is located on one of the most beautiful islands in the Florida Keys...world famous Summerland Key!! The home boasts 3 nice sized bedrooms and 4 full baths with an elevated porch off the living room and a second porch off the third story bedroom with amazing views of the Atlantic Ocean. This home is nicely equipped with a heated pool, tiki hut, boat ramp, a concrete seawall, storage area and bonus storage room for all your toys. This is a rare true open water property located in a AE flood zone for a very low F.I.P. This home is easy and a pleasure to show... It has everything youve dreamed about!

296  Caribbean Drive  For Sale, MLS 583618
$1,140,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,288 SqFt Days Listed: 220
-4.60% ($55,000) 1 Price Change : Last Change 85 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

1121  Ocean Drive  For Sale, MLS 582802
$1,159,000
Summerland Key
Summerland Beach   - MM: 25.00
2 Bed, 2 Baths, 2,304 SqFt Days Listed: 277
-9.10% ($116,000) 1 Price Change : Last Change 204 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp

Enjoy the tropical breeze and the magnificent view of the Atlantic Ocean as you relax on the front porch of this ocean front home. This 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.

1090  Gulf Drive  For Sale, MLS 586962
$1,249,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
2 Bed, 2 Baths, 1,502 SqFt Days Listed: 6
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 120ft.

Gated double lot estate, with stilted concrete home, 120 feet of seawall, 2 boat lifts 10k and 17k, , approx 300 feet of waterfront, Point lot in Summerland Cove Isles, Boat ramp on property, 295 sf lower level enclosed space for all your fishing gear located right next to the dock, 1552 sf of porches and patios, Dock House located next to Boat ramp for additional storage/workshop, plenty of parking for all your toys, trailers, boats, etc, room for pool, Plans for a pool, drawings can be passed on to new owner, call agent for details

1200  Ocean Drive  For Sale, MLS 583477
$1,250,000
Summerland Key
Summerland Estates   - MM: 25.00
3 Bed, 3 Baths, 1,820 SqFt Days Listed: 228
-34.18% ($649,000) 4 Price Changes : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 300ft.

20 acre estate direct on ocean in beautiful Summerland Key New marble floors throughout entire home. New travertine marble on all outside decks and stairs Panoramic views from every area of house. New blue granite counter tops and stainless steel appliances. All new impact windows and doors. Two brand new A/C units. Vaulted ceiling with large coral fire place for those rare chilly nights. Long winding drive way with total privacy and security.

1330  Ocean Drive  For Sale, MLS 586000
$1,298,000
Summerland Key
Snug Harbor Subdivision   - MM: 25.00
2 Bed, 2 Baths, 1,144 SqFt Days Listed: 72
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Davits

Summerland Key!! This island style CBS waterfront home has open beamed ceilings throughout, and large covered porches overlooking the pool and canal. Enjoy the in-ground pool, concrete dock, 22,000 LB boat lift and davit. Quick ocean & Gulf access from this location. Below is a garage, storage room, open carport with full concrete slab and fenced yard. Adjacent waterfront (tier III) lot and 35 Wellcraft Scarab Boat with triple 300 Evinrudes included in the list price.Sewer connection has been completed.

240 S Airport Drive  For Sale, MLS 582525
$1,449,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 2,319 SqFt Days Listed: 291
-3.34% ($50,000) 1 Price Change : Last Change 33 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.

Calling all Pilots and Captains! Fly into and boat out of this well appointed hangar home perched on the Summerland Key Airport. Fly in and hangar your plane in the 1,531 sq ft hangar or arrive by boat and dock your vessel at the 60 ft concrete dock. This airport is one of the few in the country that offers the best of both worlds! Step inside where you will enjoy soaring tongue and groove wood ceilings, Chefs Kitchen with stainless appliances, gas range and granite countertops, spacious Bedrooms,Den, and top floor Master Suite with private veranda and ocean views. Step outside and lounge in your waterfront pool, watch the planes from one of the terraces, or take a quick trip to the ocean from your concrete dock equipped with additional floating platform for easy canal access.

1183  Caribbean Drive  For Sale, MLS 584834
$1,695,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 3,119 SqFt Days Listed: 151
-4.78% ($85,000) 2 Price Changes : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Davit Pads

Located on one of the prettiest islands in the Florida Keys in the best location! This unique gated point estate conch style home in Summerland Key has been completely remodeled with hardy board siding, and over 300 feet of concrete seawall/dockage to include water on three sides. Direct Ocean access with the most incredible views from this home. The huge property is gated & surrounded by lush tropical vegetation for privacy. The grounds include an outdoor shower, 2 heavy duty boat lifts, boat davits, floating dock for PWCs, 2 car garage, ocean view decks, 2 fish cleaning stations and 4 Monster green underwater lights. There are camera security systems that are viewable via the internet.

414 E Caribbean Drive  For Sale, MLS 578894
$1,700,000
Summerland Key
Summerland Key Cove   - MM: 25.00
4 Bed, 4 Baths, 2,766 SqFt Days Listed: 542
-5.56% ($100,000) 2 Price Changes : Last Change 135 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip60ft.Concre

Ocean & Boating Enthusiast Dream Home! Panoramic views as far as the eye can see and deep water boating access completely fortified in this concrete palace. Instant ocean access to world class fishing and just 5 miles from Looe Key a national underwater attraction! Incredible open floor plan thoughtfully designed by Glen Gray is perfect for entertaining with Ocean views from almost every room! Easy to maintain with impact doors, concrete construction, and metal roof. If considering use as a vacation rental this home includes amenities above and beyond any vacationers needs. A true must see for those who appreciate a well built home and enjoy their time on the beautiful Florida Keys water ways!

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 08-17-2019.

Shoreline Properties
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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