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 28
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89 N Lake Drive  For Sale, MLS 587007
$443,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,024 SqFt Days Listed: 117
-1.34% ($6,000) 3 Price Changes : Last Change 6 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

OWNER FINANCING AVAILABLE with larger amount down. 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, Bonus Room/Sm Bedroom, 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: 210
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
$694,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,280 SqFt Days Listed: 80
-0.72% ($5,000) 1 Price Change : Last Change 22 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.

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: 58
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.

1032 E Caribbean Drive  For Sale, MLS 588607
$699,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,380 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp

Beautiful Summerland Key! Solid concrete block home over looking calm deep blue waters from the back porch, with a short ride to the Atlantic Ocean. This is one of the premier boating neighborhoods in all of the Fl. Keys. 3 bedroom 2 bath split floor plan has high ceilings, open floor plan and a big screen porch for all your outdoor enjoyment. The home faces south with nice breezes and a tropical back yard with dock and boat ramp. New copper metal roof, tiki hut, private outdoor shower and a storage area downstairs! Dont miss this one! Please call listing agent for details or showings.

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: 115
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.

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: 245
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
$770,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 151
-3.14% ($25,000) 1 Price Change : Last Change 8 Days Ago
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.

1089  Ocean Drive  For Sale, MLS 588322
$789,000
Summerland Key
Summerland Beach   - MM: 25.00
2 Bed, 2 Baths, 1,020 SqFt Days Listed: 22
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Dreaming of a house that looks out on the open sea? This is an exceptional opportunity to purchase a gorgeous little oceanfront hideaway with lots of character and the feel of a Polynesian beach resort. The property is located in Summerland Beach, a safe, friendly neighborhood of estate homes only 25 miles from Key West. It offers good boating access to Niles Channel and spectacular views of sea and sky. Nestled on almost half an acre of mature native forest and green lawns, this sturdy architectural gem from the 1970s is built on wooden piers using heavy natural cedar and pine with a standing-seam steel roof. Wide roof overhangs provide shade and rain protection. The home is configured into separate living and sleeping areas connected by a deck and landscaping. The open concept

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: 199
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.

1121  Ocean Drive  For Sale, MLS 582802
$989,000
Summerland Key
Summerland Beach   - MM: 25.00
2 Bed, 2 Baths, 2,304 SqFt Days Listed: 393
-22.43% ($286,000) 2 Price Changes : Last Change 32 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.

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: 322
-9.10% ($100,000) 3 Price Changes : Last Change 157 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!

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: 242
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

24318  Caribbean Drive  For Sale, MLS 587651
$1,095,000
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,713 SqFt Days Listed: 65
-2.84% ($32,000) 1 Price Change : Last Change 26 Days Ago
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: 336
-4.60% ($55,000) 1 Price Change : Last Change 202 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

1090  Gulf Drive  For Sale, MLS 586962
$1,199,000
Summerland Key
Summerland Cove Isle   - MM: 25.50
2 Bed, 2 Baths, 1,502 SqFt Days Listed: 122
-4.00% ($50,000) 1 Price Change : Last Change 1 Day Ago
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

650  Cruikshank Isle   For Sale, MLS 588474
$1,200,000
Summerland Key
Cruikshank Island   - MM: 24.50
2 Bed, 2 Baths, 1,638 SqFt Days Listed: 10
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davit Pads152ft.

This custom built concrete Oceanfront home is located on Cruikshank Isle, a small coastal Island of 8 homes on Summerland Key. Offering over 1,600 sq ft, this home features an open floorplan and is highlighted by endless ocean views from every room. The spacious Great Room, centered by a coral fireplace, enjoys Keys famous sunsets over the ocean through walls of glass. The full length waterfront Porch is accessed by all rooms including the 2 Master Suites at each end of the home. Fantastic deep draft boating and immediate ocean access from the full 152 concrete dock and seawall. The 11,761 sq ft fully fenced lot allows for plenty of space for all of your toys.

25361  1St Street  For Sale, MLS 588349
$1,378,000
Summerland Key
Summerland Beach   - MM: 25.00
3 Bed, 3 Baths, 2,535 SqFt Days Listed: 20
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Summerland Key Beach ocean front jewel. 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
$1,399,500
Summerland Key
Summerland Key Cove   - MM: 25.00
5 Bed, 5 Baths, 3,651 SqFt Days Listed: 37
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

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: 112
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.

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 12-11-2019.

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