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 25
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89 N Lake Drive  For Sale, MLS 587007
$448,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,024 SqFt Days Listed: 63
-0.22% ($1,000) 1 Price Change : Last Change 13 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

OWNER FINANCING AVAILABLE. Deep Oceanside Boating Canal. New Roof 2018, Large Downstairs Enclosure Below, Hooked Up To Sewer. Lot With Ample Parking For All Your Toys.... Access to Fly In - Fly Out Community. Home Features An Open Floor Plan, Room for Second Bath, Porches, Full Length Seawall. Good Access to the Best Diving & Fishing Places - Oceanfront & Gulf. Quick Commute to Key West. Located on a road with little traffic ......

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: 156
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

549 E Caribbean Drive  For Sale, MLS 587442
$699,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,280 SqFt Days Listed: 26
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 30ft.Concrete

Coming Soon! Brand New home is under construction now, 3 bedroom 2 bath 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- just 30 minutes to Key West. This home should be completed by Nov 2019- secure your contract now! The lot is 60 x 100 with 60 canalfront, 30 concrete dock with steps down for kayaking. 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, laundry room. Active Construction site, do not access without an agent.

867  Caribbean Drive  For Sale, MLS 587017
$699,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,032 SqFt Days Listed: 61
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

Keys Vacation Living. Live the good life. Home shows beautifully with open floor plan and large porch that overlooks the flow through, wide canal system filled with tropical fish. Excellent boating, just minutes to the Atlantic and Gulf. A short walk or bike ride to some of the best restaurants in the Lower Keys. Plenty of parking and low maintenance pea rock yard and 60 of concrete seawall with a boat lift. Storage enclosure and shed. Sewer connection in progress.

869  Lagoon Drive  For Sale, MLS 587748
$699,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
2 Bed, 2 Baths, 1,548 SqFt Days Listed: 4
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

This CBS home is located on a double lot in desirable Summerland Cove Isles. Property can be divided after meeting Monroe County guidelines.. Vaulted ceilings offer a wonderful sense of both space and light. Features include tile floors, emergency generator, breezeway, two car climate controlled garage, and a 17000lb boat lift. No stairs make getting groceries in as easy as possible. The concrete seawall runs the entire length of the property and boarders the open deep-water canal which gives you easy access to both Gulf and Ocean where the fish are waiting for you! If you like to dive or snorkel you are twenty minutes from Looe Key Reef, one of the lower Keys popular dive sights.

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: 191
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 586478
$795,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 97
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: 145
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Ready for an Investment / vacation home 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
$845,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 176
-6.01% ($54,000) 4 Price Changes : Last Change 11 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat RampConcrete

Magnificent Oceanfront Location! Southern Exposure. Deep Draft For Big Boats. 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, Beautiful 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: 268
-9.10% ($100,000) 3 Price Changes : Last Change 102 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 & room for Pool, RV and more!

24318  Caribbean Drive  For Sale, MLS 587651
$1,127,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,713 SqFt Days Listed: 11
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!

24856  calle real   For Sale, MLS 587578
$1,140,000
Summerland Key
Summerland Beach   - MM: 25.00
3 Bed, 3 Baths, 2,283 SqFt Days Listed: 16
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits238ft.

Beautiful location with endless views of the Atlantic Ocean. Enjoy your new home on the open water while having the protection of a boat basin. This 3 bedroom open water home needs some TLC, but has lots of amazing features.The property currently has multiple offers H&B with a current due date of10/15/2019 11:59:00 PM Mountain Time.Employees or directors of JPMorgan Chase & Co. and its direct and indirect subsidiaries are strictly prohibited from directly or indirectly purchasing any property owned or serviced by or on behalf of JPMorgan Chase & Co. or its direct and indirect subsidiaries.

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: 282
-4.60% ($55,000) 1 Price Change : Last Change 147 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: 339
-9.10% ($116,000) 1 Price Change : Last Change 266 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: 68
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

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: 134
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
$1,399,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 2,319 SqFt Days Listed: 353
-6.67% ($100,000) 2 Price Changes : Last Change 36 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.

280 E Caribbean Drive  For Sale, MLS 587066
$1,400,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 58
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.

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: 213
-4.78% ($85,000) 2 Price Changes : Last Change 66 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 587599
$1,729,000
Summerland Key
Summerland Key Cove   - MM: 25.00
4 Bed, 4 Baths, 2,766 SqFt Days Listed: 14
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip60ft.Concre

This impressive custom built Glenn Gray designed 4 BR 3.5 BA Oceanfront home boasts picture perfect views of the endless ocean where world-class fishing & diving are just minutes away. After a great day on the water dock your boat in the slip & refresh in your oceanfront pool while cooking the days catch at the poolside summer kitchen or sip champagne from one of the many decks overlooking the ocean. Guests will loved to be entertained in your well-appointed Great Room featuring a chefs Kitchen w/granite counters, stainless appliances & amazing ocean views or on the waterfront lanai to catch the sunset. Retire in the 2nd floor Master Suite where you will awake to gorgeous views of the open ocean from your private veranda. Impact doors & windows, metal roof & much more.

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 10-18-2019.

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

1(800) 692-3605
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