Summerland Key Homes for Sale, Single Family Houses, MLS Home Listings

Summerland Key real estate is known for its outstanding luxury and waterfront Florida Keys homes.  The prestigious island is located a mere 20 minutes from the popular Key West, while at the same time being a private enclave of unparalleled beauty and exclusive real estate.  Houses for sale in Summerland Key exude the beauty and tranquility of their surroundings.  Interested in Summerland Key homes for sale?  Browse the Florida Keys MLS to see all available listings in Summerland Key.

Total Listings 35
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676 E Shore Drive  For Sale, MLS 587536
$329,000
Summerland Key
Summerland Beach   - MM: 25.00
2 Bed, 2 Baths, 870 SqFt Days Listed: 75
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Great starter home on a large lot with mature landscaping which includes right of use of Blanche Bergin Park Marina for boat access and launch (see documents tab) as well as convenience to the Summerland airstrip. This 2 bedroom, 1 bath ground level home offers an additional bonus room, has hardi-board siding, a metal roof and is hooked up to sewer.

25095  5th Street  For Sale, MLS 586498
$429,000
Summerland Key
Summerland Beach   - MM: 25.00
2 Bed, 2 Baths, 832 SqFt Days Listed: 152
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Two bedroom, one bath home with spacious kitchen/living area. Vaulted Ceilings. Full length screened porch. Enjoy nature from your porch. Custom built home in 1999, located in beautiful Keys Hammock(hardwood forest) Corner lot with lots of mature native trees. Lots of outside area, room to park your RV, Boat or other toys.

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: 120
-1.34% ($6,000) 3 Price Changes : Last Change 9 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 ......

25024  45Th Street  For Sale, MLS 586192
$449,000
Summerland Key
Summerland Estates   - MM: 25.00
5 Bed, 5 Baths, 1,812 SqFt Days Listed: 178
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This property offers endless opportunities for income potential and/or building on the adjacent lot. It has plenty of space for a hanger to store your plane, a couple of boats, and a large pool. The community boat ramp is deeded to the property, and a community air strip is located right down the road.

227 North Airport Drive  For Sale, MLS 585180
$449,000
Summerland Key
Summerland Key Cove   - MM: 25.00
1 Bed, 1 Baths, 756 SqFt Days Listed: 247
-2.18% ($10,000) 2 Price Changes : Last Change 141 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Fly into beautiful Summerland Key, midway between Key West and Marathon, considered to be one of the most prestigious tropical islands in the Florida Keys. Soar over the magnificent and breathtaking views of the spectacular reefs and tropical waters. Then park your airplane under your home and enjoy world famous boating and fishing in the waters surrounding Summerland Key. Or leave for the fun and nightlife of Key West only minutes away. If you are not an aviator, take the drive across the 42 bridges of the Overseas Highway on your way to Paradise. Directly on the private Summerland Key airport, this home away from home is the perfect place to get away from it all! Features cement plank siding, metal roof, and large doors and windows offering natural light and cool tropical breezes.

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: 213
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

287  Airport Drive  For Sale, MLS 588664
$499,000
Summerland Key
Summerland Key Cove   - MM: 25.00
4 Bed, 4 Baths, 1,260 SqFt Days Listed: 2
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Other Dockage

Rare find! 4BR/2BA cottage located directly on the Summerland Key Airstrip! This newly remodeled home is super charming and boasts an open floor plan featuring vaulted Dade County Pine ceilings, terrazzo floors, new Kitchen with stainless appliances, farmhouse sink, island and pantry. The split floor plan offers dual zone a/c, 3 Guest Bedrooms, new Guest Bathroom and a Master with new ensuite Bath. Storm ready with impact doors and windows and metal roof. Located next to the community park which offers lots of back yard privacy and easy access to the community boat ramp offering excellent ocean and back country access.

24830  Park Drive  For Sale, MLS 588001
$499,999
Summerland Key
Summerland Key Cove   - MM: 25.00
3 Bed, 3 Baths, 1,188 SqFt Days Listed: 44
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This Beautiful 3BD/2BR Home is located in Summerland Key Cove. It features custom bathrooms, beautiful wood tile flooring and many other features. The Master walk in closet showcases custom built shelving for additional storage. It includes all stainless steel appliances and washer and dryer. The home also features a downstairs lower enclosure with built in shelving. One of the best features is the outdoor space, you have tons of entertaining space underneath on the concrete slab, with the entire back yard in stone featuring beautiful landscaping all around the home. You also have private access to the neighborhood boat ramp. And youre only a quick 25 minute drive to Key West.

195  Airport Drive  For Sale, MLS 588165
$595,000
Summerland Key
Summerland Key Cove   - MM: 25.00
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 35
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Other Dockage

Fly In & Fly Out....Summerland Key Community....Beautiful Concrete Block Home With Pre-Stress Concrete Beam Construction. Airplane Hanger, Large Screen Porch & Hot Tub, Ample Storage Up & Down, Cargo Lift, Fence. Features 2 Bedrooms With 2 Full Baths, Open Layout With High Ceilings, Custom Kitchen, Large Walk-In Pantry, Laundry Room &Tile Floors Throughout. Access To The Park & Pond. Conveniently Located With Quick Commute to Key West & Big Pine Key. Fly In, Fish, Play, Dive Looe Key, Visit Back Country Beaches...Enjoy Your Stay & Key West Night Life....

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: 83
-0.72% ($5,000) 1 Price Change : Last Change 25 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: 61
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: 6
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: 118
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: 248
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: 154
-3.14% ($25,000) 1 Price Change : Last Change 11 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: 25
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: 202
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: 396
-22.43% ($286,000) 2 Price Changes : Last Change 35 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: 325
-9.10% ($100,000) 3 Price Changes : Last Change 160 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: 245
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

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 12-14-2019.

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