Summerland Key Real Estate

Summerland Key Real Estate

Welcome to Summerland Key, a beautiful island paradise located in Monroe County, Florida. This charming city is a hidden gem nestled in the heart of the Florida Keys, offering a unique blend of natural beauty, outdoor adventures, and a laid-back island lifestyle.

Situated in the southernmost part of Florida, Summerland Key is surrounded by crystal-clear turquoise waters and pristine white sandy beaches. This coastal community is renowned for its world-class fishing, diving, and boating opportunities, making it a haven for water enthusiasts. Whether you're an avid angler looking to reel in the catch of a lifetime or a scuba diving enthusiast eager to explore vibrant coral reefs, Summerland Key has something for everyone.

Aside from its stunning natural surroundings, Summerland Key boasts a close-knit community and a relaxed atmosphere. Residents and visitors alike can enjoy a range of amenities, including quaint shops, delicious seafood restaurants, and vibrant local art galleries. The city also offers excellent schools, making it an ideal place for families to settle down and raise children.

With its convenient location in Monroe County, Summerland Key is just a short drive away from the vibrant attractions of Key West, including its lively nightlife, cultural events, and historical landmarks. Whether you're looking for a peaceful retreat or an adventure-filled getaway, Summerland Key offers the perfect balance of tranquility and excitement.

Come and discover the allure of Summerland Key, where the sun-kissed beaches, breathtaking sunsets, and warm hospitality await. Whether you're seeking a permanent residence or a vacation home, this idyllic city is a true paradise for those who appreciate the beauty of coastal living.

Newest Listings in Summerland Key

$375,000
A12064574 MLS
Vacant lot with active building permit. Permit and plans include a fully designed green home with full concrete construction and concrete roof for 3 bedroom 2.5 bathrooms, large porch, storage and guest space, downstairs storm rated impact windows and doors, solar panel, gray water reclaim system plus rainwater system for irrigation and boat washing fish at Dawn cook your cat by dusk near Loki Tiki in lower ramrod key.

27378 Jamaica Lane, Summerland Key
$985,000
A12049052 MLS
ROGO EXEMPT CANALFRONT WITH GREAT SUNSETS AND OPEN WATER VIEWS READY FOR YOU TO BRING YOUR BOAT WITH STEP DOWN DOCK. DOCK NEEDS SOME TLC. ACTIVE WATER METER ON SITE, SEWER STUBBED IN AND READY FOR CONNECTION AS A PRIOR HOME WAS DEMOLISHED. BUYER TO VERIFY ALL INFORMATION. POWER IN FRONT. SURVEY AVIALABLE. TWO STORY HOME WOULD PROVIDE SPECTACULAR VIEWS AND A TREMENDOUS OPPORTUNITY FOR YOUR VISION, NOW OR LATER. OWNER/AGENT SOLD AS IS.

Summerland Key
$1,775,000
4 Beds ⋅ 4 Baths ⋅ A12042729 MLS
Brand new waterfront in the Keys, built for you from the ground up. This is a preconstruction home in Cutthroat Harbor Estates. You buy now and it gets built for you, delivered turnkey. Picture it: your boat at the private dock on approx. 102 ft of canal seawall, a pool and jacuzzi below, coffee on the rooftop deck. Elevated 4 bed, 4 bath, outdoor kitchen, solar and efficient systems, brand new and low maintenance. And the best part? The permit is already secured, so your home gets built now instead of years from now.

193 Galleon Lane, Summerland Key
$170,000
A12018646 MLS
If you love fishing, love the water, and hate the big crowds, this is the place for you! Upon arrival, the first thing you will notice is the peace and quiet. Easy access to the Gulf of America and Atlantic Ocean. This property is adjacent to my other listing which is owned by the same person. This would be an excellent opportunity to own a double lot on Big Torch Key! Adjacent property (blue house) MLS#A12018522; 4276 Dorn Rd.**Water photos at the end are for reference to show what the water looks like at the end of the canal. This property does not directly have this view**

Lot 27 Lot 27 Dorn Road, Summerland Key
$350,000
2 Beds ⋅ 1 Baths ⋅ A11979130 MLS
Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or income-producing rental. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white kitchen pops with marble countertops and a stunning blue tile backsplash, bringing those breezy ocean vibes right into your home. It's light, cheerful, and perfect for entertaining friends and family after a day on the water. And here's the best part — even though this property sits on a dry lot, you still enjoy beautiful open water views. Venture Out is one of the most sought-after gated communities in the Lower Keys, known for its active lifestyle and incredible amenities: Heated community pool, Marina & boat ramp with direct ocean and Gulf access, Tennis & pickleball courts, Basketball courts, Private convenience store, Children's playground & pool, Recreation hall, 24-hour gated security. Bring your boat, your golf cart, and your flip-flops — this neighborhood was made for enjoying the water. Located just 20 miles from Key West, you're close enough for dining, nightlife, and the airport — but far enough away to enjoy peaceful island living. If you've been dreaming of a cozy, beach-inspired Keys escape with income potential and resort-style amenities... this is the one.

701 Spanish Main Drive Unit 536, Summerland Key
$1,100,000
3 Beds ⋅ 2 Baths ⋅ A12018522 MLS
Welcome to your slice of paradise! Down in Big Torch Key, you'll feel a sense of solitude, satisfaction and serenity. Minimal, if any, noise or light pollution on this Key; look up at night and you will see stars you've never seen before! Quick and easy access to the Atlantic and Gulf of America, plenty of fishing spots and places to relax on the water without those big upper Key crowds. The adjacent vacant lot for sale is owned by the same person - a perfect opportunity to purchase two lots and transform into one! With this dock size already at 65', imagine how many more boats you could dock with both lots!Vacant land MLS#A12018646**Water photos at the end are for reference to show what the water looks like at the end of the canal. This home does not directly have this view**

4276 Dorn Road, Summerland Key
$1,050,000
3 Beds ⋅ 3 Baths ⋅ A11986220 MLS
Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly found in the Keys. The elevated concrete home features a spacious layout, multiple balconies, and abundant natural light throughout. With kitchen and bathrooms ready for renovation, this is the perfect canvas to create a custom waterfront residence or maximize value through a strategic upgrade.Enjoy ample outdoor space with room for expansion, a pool, additional storage or enhanced landscaping - making this property uniquely versatile for both end-users and investors.Ideally located within close proximity to Key West, offering convenient access to world class dining, entertainment and boating, while still enjoying the privacy and tranquility of canal front living.

27403 Antigua Lane, Summerland Key
$895,000
3 Beds ⋅ 2 Baths ⋅ A11998100 MLS
Offered in the highly sought-after Jolly Roger Estates, this beautifully maintained, one-owner canal-front home is just 11 years old and truly move-in ready. Elevated and thoughtfully designed, the 1,296 sq. ft. residence offers three bedrooms and two bathrooms, enhanced by refined finishes including crown molding, tray ceilings, tile showers, and a bright, open-concept living space ideal for coastal living. Built for both comfort and peace of mind, the home features a metal roof installed in 2018 along with impact-rated windows and doors throughout. Enjoy added privacy and nightly sunset views over the protected salt marsh directly across the street—an unspoiled natural backdrop that will never be developed. Boaters will appreciate the free-flowing, clear-water canal with excellent access to both the ocean and the bay. The private dock with a 7,000-lb side-lift boat elevator makes heading out for fishing, diving, or sunset cruises effortless. The spacious lot offers a large driveway, double covered parking, and ample room for boat trailers and additional vehicles. Downstairs, a full concrete pad and enclosed angler's room provide the perfect space for storing fishing gear, dive equipment, and all your island toys. Located near mile marker 28.5, Jolly Roger Estates is a peaceful, palm-lined waterfront community on the Atlantic side of Little Torch Key, offering direct access to Pine Channel and world-class boating, fishing, and diving at nearby Looe Key Reef.

437 Pirates Road, Summerland Key
$269,999
A4697420 MLS
Beautiful .55 acre lot in Summerland Key, FL. Summerland Key is a unique fly-in community with a private airstrip and marina close by. SUMMERLAND ESTATES SUMMERLAND KEY PB2-167 PT LT 25 (LOT A 90 FT X 264.75 FT). Buyer is responsible for conducting due diligence on the property prior to purchase.

Sunset Boulevard, Summerland Key
$4,250,000
5 Beds ⋅ 6 Baths ⋅ R11113452 MLS ⋅ The Seven Palms - A Key West Oasis BLDG.
Welcome home to an exceptional new-construction residence in a private, gated community offering resort-style amenities, a boat slip and nightly rental opportunities. Conveniently located next to Summerland Key Airport, this fully upgraded home features a private elevator, a stunning infinity pool overlooking the water and an expansive rooftop deck perfect for enjoying breathtaking Florida Keys sunsets. Only have two homes remaining.

231 E Shore Drive Unit Unit 2, Summerland Key
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