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 31
Order By:

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: 18
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: 95
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.

25240  Margaret Street  For Sale, MLS 587342
$429,000
Summerland Key
Summerland Estates   - MM: 25.00
2 Bed, 2 Baths, 1,204 SqFt Days Listed: 32
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Boat Ramp,First Come

Fantastic dry lot opportunity on high demand Summerland Key. Property includes a second lot to the east with south and west elevations bordered by retired government owned property which yields fantastic elbow room and privacy! The 2/2 stilted home with metal roof has potential for third bedroom or office/den area. Very nice screened outdoor living/entertaining area patio rear of lower level. Located near the Summerland airstrip ocean side. Property ownership includes access to home-owners marina park with boating ramp and access, no mandatory fees associated with park access.

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 ......

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: 121
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: 190
-2.18% ($10,000) 2 Price Changes : Last Change 83 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.

25052  Palm Lane  For Sale, MLS 586058
$469,000
Summerland Key
Summerland Key Gard   - MM: 25.00
3 Bed, 3 Baths, 1,458 SqFt Days Listed: 131
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

CBS raised ground level home beautifully updated located in Summerland Key. Featuring a brand new kitchen with soaring ceilings this home is one of the few move in ready options under 500k available today. Enjoy the extended living space outside on the tile and stacked stone patio which flows seamlessly from the kitchen and living room. The master suite is expansive with vaulted ceilings and opens to the fully fenced private backyard. On demand hot water heater, custom double vanity sinks, and stainless steel appliances are just a few of the endless upgrades this home boasts. Schedule your private tour now.

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.

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
Contact Us