Summerland FL Real Estate, Homes, Condos for Sale

Welcome to your slice of paradise in the heart of the Florida Keys! Nestled on the picturesque shores of Summerland Key, the waterfront haven that embodies the quintessential Florida Keys lifestyle. This charming 2 bedroom 2 bath property boasts the perfect blend of comfort, convenience, and coastal charm. Enjoy the breathtaking beauty of living on the water, with 60 ft of canal frontage and quick access to both the Atlantic Ocean and the Gulf of Mexico. This is a boater's dream come true! Summerland Key offers a laid-back island lifestyle, with easy access to world-class fishing, diving, and snorkeling. Discover nearby restaurants, shops, and attractions, or simply savor the tranquility of your own tropical paradise.

24357 W Caribbean Drive, Summerland

$2,150,000

3 Beds ⋅ 2 Baths ⋅ 606553 MLS

Enjoy the true ''Island Life'' in this stunning almost 2100 sq. ft. waterfront property, with a pool, in sought after Summerland Cove Isles. This quiet and highly desirable subdivision is known for its 60' wide clean flow through turquoise canals with excellent deep water boating access to both the Atlantic and the Gulf. You are up on plane in just minutes after you leave your dock and head out to do some world class Florida Keys fishing and diving. This 3 bedroom 2 bath concrete fortress is situated on an oversized lot offering 90' of dockage with a 15,000 pound boat lift and 10,000 pound davits to accommodate both your offshore and backcountry boats. Once inside you are welcomed into a spacious living area flooded with natural light from the oversized picture windows on three sides, it is the perfect room for entertaining. Step up into the well appointed eat in kitchen which offers quartz counters and updated stainless steel appliances featuring a gas stove with a hideaway venting system. The large master has a beautiful oversized walk in shower with a bench, built in closets, and dual sinks for convenience. The guest bedrooms and bath are also generous in size and continue with the keys decor to give the home a real island feel throughout. Mature tropical landscaping, paver driveway, and expansive outdoor entertaining area by the in ground pool with privacy fence and electric roll down shades add to the keys ambiance of this impressive home. The solid concrete construction, metal roof, and impact windows and doors, with added roll down shutters, help to keep insurance premiums lower. Summerland Key is located close in proximity to our Lower Keys backcountry known for stellar flats fishing and lobstering, as well as beautiful pristine out island sandy beaches. Only a short drive to Key West where you will find fabulous restaurants and nightly entertainment.

1126 Lagoon Drive, Summerland

$1,275,000

2 Beds ⋅ 2 Baths ⋅ 606463 MLS

Location...Location... Location!Near the end of Ocean Drive, on coveted Summerland Key, Just 2 mins from BOTH Ocean & Gulf access, lies this beautifully remodeled gem! GORGEOUS Quintessential Beach Cottage- beautifully Renovated & ready for her new owners.Boat Owner? She's ready...60' concrete dock on 60' wide canal.Private plane? Bring it...Airstrip community-short golf cart ride or walk away!NEW Impact windows & doors, Bright & White kitchen with Gleaming Quartz Countertops- Shiny Stainless Steel appliances, ample cabinetry & spacious kitchen island is ready to entertain! Open floor-plan creates airy feel. Generously sized Two Bedrooms, Two Renovated Baths, Metal Roof (2015), Over-sized Garage with ample storage, Updated HVAC (2021).The work is done, time to play- welcome to paradise! Hurry to claim!

1342 Ocean Drive, Summerland

$2,295,000

3 Beds ⋅ 2 Baths ⋅ 606457 MLS

Exclusive Summerland Cove offering! This quality, concrete home has an incredible location for view, privacy, and exceptional boating access. Concrete structure including floors, decks and lower storage room. Summerland Key is known for is beautiful aqua canals, deep water boating access, and easy proximity - just 24 miles to Key West. Interior sq ft is 2160- the main living floor is 2 bedrooms / 2 baths- and the 3rd bedroom is a huge open loft upstairs. Beautiful kitchen with white cabinets, quartz countertops and new stainless appliance package. . Warm wood accents throughout the home. Elevated higher than average, with great clearance for parking underneath- even an RV or tall boat trailer. Screen porch offers fantastic ocean and lagoon views and spectacular sunsets. 64' concrete dock with davits and fish cleaning table. Fenced yard and pool. Metal roof, impact windows and doors.

1165 Lagoon Drive, Summerland

$5,495,000

3 Beds ⋅ 4 Baths ⋅ 606236 MLS

This is Keys Luxury: a Coastal Island Style Home! Architecturally striking, state-of-the-art, CBS home & a spectacular observation deck where you can see for miles and miles! The home drinks in outdoor living. Designed facing West, for year round sunset views. Kitchen opens onto the pool deck. Featuring a gourmet kitchen: granite, custom cabinetry, Sub Zero/ Wolf appliances. The center island has a custom black walnut top, with a copper sink. Dramatic elevated infinity edge pool sits16 feet in the air. Surrounded by fire features. Spa spills into pool. Bar and lanai area equipped with a gas fireplace.Patio bar has a black walnut top, bar sink, appliances. The back wall on the bar is reclaimed pecky Cyprus. Full bath located by the pool bar. Sunsets, water views, taken in from the pool deck, lanai and from the observation deck. Well appointed Master Bedroom, two walk-in closets, grandiose master bath: two vanity's, a sumptuous tub, a walk in shower and an outdoor shower! Off the master suite is the Sunset area with wet bar & white washed ceilings, add a pool table or it's a sitting room. Two more bedrooms en suite with full baths. Natural light streams in through the top of the line impact windows and doors. Staircase has custom black walnut treads. 130 feet concrete dock spans both lots. Room for plenty of water craft. Protected deep water dockage. Immediate access to the Ocean, world-class offshore fishing & diving. Another modern feature is that it is Smart Home ready. The home is equipped with an elevator. Park vehicles under the home, providing access to the elevator. Storage room with ample space. Plenty room for parking on this large property. An underground LP gas tank. Quality concrete construction, fully custom residence, just a stone's throw from the Ocean. Perfect for those seeking splendor and luxury, with a bit of fun thrown in! While under construction, purchase at any stage. Price will increase as construction progresses to completion.

999 Flagship Drive, Summerland

$1,150,000

3 Beds ⋅ 2 Baths ⋅ 606235 MLS

This picturesque real estate gem boasts 3 bedrooms and 2 bathrooms in a location that promises to elevate your Florida Keys lifestyle, offering a blend of tranquility and convenience making it an idyllic oasis for those seeking a peaceful and luxurious lifestyle. Low Insurance costs make it affordable. Porches and decks everywhere. Outdoors, an oasis awaits you with a private fenced backyard where a sparkling swimming pool invites you to cool off during hot summer days and provides the ideal spot for relaxation, family gatherings and entertaining friends. Includes 60' of concrete seawall and easy deep-water boating to the Atlantic and Gulf of Mexico. The metal roof enhances the home's durability, ensuring protection from the elements and peace of mind for years to come. New HVAC that has 8 years of warranty remaining. An added convenience is the downstairs storage area, providing plenty of room for all your outdoor equipment, sporting gear, and water essentials. For those with a passion for aviation, this property boasts airport access, providing added convenience for private pilots. Don't miss the chance to make this coastal retreat your forever home! Annual insurance costs are: Wind: $2,963, Home Owners: $1,395 and Flood: $714.

76 W Shore Drive, Summerland

$1,999,900

4 Beds ⋅ 3 Baths ⋅ 606195 MLS

Bright and spacious Summerland Key beach cottage retreat, on a peaceful corner lot, with endless turquoise Water Views! This prime location is ideal for the avid boater, outfitted with all the necessities including 120' seawall, 17K boat lift, 7500 lb. davits, fillet station, and enviable access to both the Gulf and Atlantic within minutes. Inside, a recently updated kitchen boasts a subway tile backsplash and sleek granite countertops. Modern wood floors throughout the home provide warmth within the space. Four generous bedrooms offer an abundance of space for family and visitors. Entertain guests and dine al fresco from the spacious open back porch, overlooking the well-maintained yard and gorgeous canal below. Rinse off salt and sand in a sizeable outdoor shower, and cool off after a day on the water in the sparkling in-ground pool. Nestled within the confines of the tranquil, established Summerland Cove Isle neighborhood, while just minutes to shops and restaurants in town! Don't wait, schedule a tour of this picturesque property today!

1082 Bay Drive, Summerland

$3,490,000

2 Beds ⋅ 3 Baths ⋅ 605854 MLS

Summerland Beach is an oceanside community in the Lower Florida Keys. With its beautiful palm trees and vibrant flowers, this seaside oasis offers a tranquil escape from the bustling outside world. Nestled on the edge of paradise, this extraordinary private oceanfront beach home welcomes you with its thatched-covered lanai entrance and glass bamboo-etched front doors.As you step inside, the energy of the ocean immediately captivates you, with mesmerizing views stretching as far as the eye can see. The spacious open-concept living area seamlessly connects the kitchen and dining spaces, boasting floor-to-ceiling windows that blur the line between indoor and outdoor living. Through these expansive windows, you can enjoy breathtaking vistas of the turquoise ocean, leading to a magnificent terrace overlooking the pool. This terrace serves as the perfect sanctuary to relax and completely immerse yourself in the beauty of the surrounding oceanscape. Those who truly want to embrace the coastal environment will find a delightful outdoor living experience downstairs. A custom bar adorned with seashells and nautical artifacts adds a charming touch to the space, honoring the area's rich maritime heritage. Additionally, there is a cooking area, hot tub, and more to enhance your outdoor experience. The pool's shimmering blue water seamlessly merges with the vast expanse of the ocean, and strategically placed lounge chairs on the sandy beach invite you to bask in the warm sun while enjoying the gentle ocean breeze. It is here that you can fully appreciate the unparalleled coastal setting. One of the true highlights of Summerland Beach is the daily display of sensational sunrises and sunsets. Imagine vibrant hues of orange, pink, and gold painting the sky, casting a spectacular glow upon the pool and the ocean.

361 Ave D, Summerland

$570,000

605346 MLS

ZONED FOR Weekly VACATION RENTALS! This is chance at an Investment Opportunity! Build your dream home today with income generating potential. Take advantage of this incredible investment property located on Mile Marker 25. This lot offers the perfect opportunity to build your dream home immediately. There are two lots side by side with one being ROGO exempt. With a ROGO letter on hand, there's no need to wait to start building. Situated in an AE Flood Zone. Additionally, it is zoned for SR, opening up the potential for daily, weekly, or monthly rentals. This means you can build a beautiful home and capitalize on the income-generating potential.

45th Street, Summerland

$17,999,900

6 Beds ⋅ 8 Baths ⋅ 605262 MLS

Just minutes from Key West, Tarpon Ranch is Summerland Key's finest private estate and the epitome of relaxed elegance. Designed by one of the best, it's a masterful union of architectural splendor with the casual atmosphere that defines the Keys lifestyle. Through the custom front gates, past a custom bronze tarpon fountain to a jaw dropping porte-cochere with exposed Ipe wooden trusses & columns are exquisite details everywhere your eyes focus. Dramatic 19' soaring cathedral ceilings, distressed & stained pine beams, magnificent Ipe pillars & custom 10 ft nano impact mahogany doors that completely open the whole house up to view the Atlantic. One of a kind heated and chilled, salt water infinity pool, competition depth with inlaid tarpon lane (25 yards) and even a swim up bar with stools. The 6 bedrooms, 6 full & 2 1/2 baths, are evenly split between the main house and the guest house by a covered breezeway. The huge great room wraps around a stunning chef's kitchen with top of the line Viking, Subzero & Miele appliances, blue labradorite granite counters w/custom inset nautilus shells. The great room also includes a casual dining area & a full custom walnut bar with ice maker, dishwasher, wine cooler & 2 subzero refrigerator drawers. Dine in a formal dining room or cook next to the pool in your indoor outdoor kitchen w/top of the line Lynx Professional & Kalamazoo appliances which opens directly to the indoor or outdoor sun room. A 520 bottle wine room, multi-zoned audio system, whole home generator, 330 gallon aquarium, enormous carport parking for at least 6 flats boats & multiple cars w/direct access to boat ramp, 100' seawall on a protected canal, 2 boat lifts, elevator, gym, 2 car garage, covered entertaining game room areas & even a room to view your pool through a pair of mermaid windows. 3 sets of washer & dryers. The list goes on...you will be amazed! Located within sight of world class & world famous tarpon flats.

1300 Sunset Boulevard, Summerland

$1,400,000

3 Beds ⋅ 2 Baths ⋅ 604759 MLS

Location! Location! Don't miss the opportunity in Summerland cove Isle. Very private fenced yard, fabulous concrete home with a metal roof. Very wide and clean flow through canal and Minutes away from the open water, 3 bedrooms 2 bath home has beautiful tile floors and granite countertops plus an upstairs screened porch for all your entertainment. There is covered parking for 6 cars. New A/C installed in 2019. Large downstairs storage room. There are 2 Functional boat davits on the deep-water canal. Plenty of room for a pool.

947 Gulf Drive, Summerland

$1,699,000

2 Beds ⋅ 2 Baths ⋅ 604706 MLS

Picturesque Summerland Key sanctuary on an oversized 10,400 sq ft lot with enviable boating access, situated on a pristine canal! Made for entertaining, this home boasts expertly utilized outdoor living space. Lush native landscaping surrounds a sparkling plunge pool, creating a private backyard oasis. A concrete dock, with a 24,000 lb boat lift and a 4,000 jet ski davit, allows for easy access to incomparable fishing and diving, and a kayak launch provides added convenience. Wash away salt and sand in a waterside outdoor shower. Steps away from your fillet station, enjoy grilling your fresh catch on a pristine grill with additional cooktop and prep space. Entertain in the shade with evening cocktails from the comfort of your chickee hut. This home truly encompasses the coveted Keys lifestyle. Inside, the open-concept main living area lends itself to relaxation. The home is bright and modern, recently updated with stylish shiplap accents, bringing warmth and character to the space. The kitchen makes culinary endeavors a breeze with sleek quartz countertops, kitchen island with counter seating, stainless steel appliances, gas range, and tasteful open shelving. The dining area is flooded with natural light and features picture windows overlooking the tropical grounds below. The spacious main bedroom boasts a walk-in closet and en suite half bathroom, with access to the expansive open back balcony through impact glass doors. The balcony overlooks the immaculate canal below, the perfect backdrop for enjoying summery sea breezes. Right down the road, you will have access to private Summerland Key Airport. Just minutes to excellent dining and shops in town but nestled within a tranquil neighborhood, this Summerland Key slice of paradise has it all. Schedule a showing today!

1330 Ocean Drive, Summerland

$999,000

2 Beds ⋅ 2 Baths ⋅ 604000 MLS

This stunning property presents an incredible opportunity to own a slice of paradise in the beautiful Florida KeysCanal front 60 ft concrete dock or Fly into Summerland Airport, this UPDATED 2 bedroom 2 bath 1499 sq ft home The well-appointed kitchen is a chef's dream, complete with modern appliances, ample cabinet space, and a convenient breakfast bar. The adjacent dining area is ideal for entertaining guests or enjoying intimate family meals. beautifully renovated, The main living area is bathed in natural light, courtesy of large windows that showcase the picturesque water views. huge laundry room with plenty of storage. Concrete Block home, some impact windows others offer accordion shutters. large storage room offers plenty of storage. New metal roof 2017, info on Summerland Airport info www.summerlandkeyairport.com

129 S Lake Drive, Summerland

$980,000

3 Beds ⋅ 2 Baths ⋅ 602225 MLS

Welcome to the best of both worlds in one of the most beautiful places in the country! Fly in and fish! Park your plane in the front yard, and your boat in the back. This 3/2 concrete home offers 1,400 SF of living space, room to park your plane (tie downs in the front yard), with 4 foot control depth on a beautiful clean canal. There is a large workshop to keep your tools and toys. After a day of fishing, rinse off in the outdoor shower then relax under the tiki hut. Offered furnished.

168 S Airport Drive, Summerland

$5,900,000

5 Beds ⋅ 7 Baths ⋅ 601840 MLS

The luxury oceanfront home located in one of Summerland Keys' most desirable neighborhoods is a masterpiece in the making. Boasting an impressive southern ocean view, this colossal 6,128 SQ FT home is currently under construction and is constructed entirely of concrete. Designed with the entertainer in mind, this home offers a spacious living area located on the 3rd floor that accentuates the amazing ocean view. The expansive floor plan encompasses five master ensuite's, a private home theater, and a private office overlooking the Atlantic Ocean. The home's 3rd floor infinite edge pool and spa provide the ultimate relaxation spot, where you can enjoy serene evening sunsets. With 90' of ocean frontage, you will have plenty of room to park your yacht and flats boat with a 24,000LB boat lift & a 10,000LB boat lift, providing immediate access to the Atlantic or Gulf of Mexico for world-class fishing. Summerland Key is conveniently located between Marathon Key & Key West, and just a short boat ride to Looe Key Coral Reef for incredible snorkeling and scuba diving. The sandy beaches of Bahia Honda State Park are just minutes away. Summerland Key is one of the unique islands in the Florida Keys to have its own private airstrip.This modern oceanfront home is designed to the 2020 FLA Building Code with 180MPH wind load. The property is currently under construction, and only authorized personnel are allowed to enter the job site. Owning a place in paradise is a dream for many, and this luxury oceanfront home offers the perfect opportunity to make that dream a reality. With its impressive design, stunning ocean views, and convenient location, this home is sure to impress. Contact the listing agent for more details on this spectacular property.

220 E Caribbean Drive, Summerland

$2,200,000

601138 MLS

Amazing opportunity in an amazing location!!! This Rogo Exempt property has the deepest draft boating in the Lower Florida Keys. 118' of protected dockage (concrete seawall) Fenced over1/2 acre with open water views and lush tropical mature landscaping and is ready to build. Plans are for a large 5 bedroom 4.5 bath CBS home with a pool. Buy it now or have it built to suit your taste. See MLS# 601133 for all inclusive price.

616 E Shore Drive, Summerland

$2,495,000

2 Beds ⋅ 4 Baths ⋅ 600810 MLS

SELLER FINANCING with 50% down. Highly visible Working Waterfront property. RARE & HARD TO FIND..Zoned Commercial Fishing Special District 13. Tier 3. Two buildings located on property, CBS building is 813 SF with 2 bathrooms, and wood frame building is 1152 SF with 2 full bathrooms. Large storage shed, boat ramp, plenty of dockage, located on a large turn around boat basin with 5ft of control depth. Sewer Connection completed to both buildings. Two electric meters, two water meters. Property is approx 94' x 117' and extends from Flagship to Center Street. Muni Code (CFSD13) & Survey located in documents tab.

24931 Overseas Highway, Summerland

$2,394,000

4 Beds ⋅ 4 Baths ⋅ 600732 MLS

Spectacular, Brand New Home in desirable Summerland Cove Isles, situated on a Deep Water Canal with Direct Ocean Access! Magnificent three story beauty featuring parking and storage on the ground floor and split floor plan, light open living space above, with a regal elevator between the two. Two generous master suites with large closets and luxuriously finished ensuite bathrooms provide the ability to relax in the epitome of comfort, along with two additional spacious bedrooms for your guests. Exquisitely laid out Chef's Kitchen offers top of the line stainless-steel appliances, with expansive peninsula, maximizing prep space. Enjoy the peace of mind offered by CBS construction and impact-resistant windows & doors throughout, expertly arranged to allow loads of natural light into the space. Up the spiral staircase, enjoy serene open ocean views from the sprawling rooftop deck, or look down on the exquisitely landscaped back yard retreat. Downstairs features a sparkling pool with ranging sundeck and sitting ledge, adjacent to 40' dock and new 20,000-pound boatlift. A graciously appointed summer kitchen will maximize your poolside entertaining potential, fully equipped for a day enjoying the marvelous Florida Keys' weather. Truly the best of all worlds wrapped up in this home, with an ideal location in an enviable neighborhood, yet quick access to world-class fishing and boating as well as delectable restaurants and stores. Don't wait to see this Summerland gem!

927 Gulf Drive, Summerland

$5,600,000

4 Beds ⋅ 4 Baths ⋅ 600668 MLS

Spectacular Open Water location, with fabulous views from this well-built Oceanfront concrete home. Direct Ocean access from the step down concrete seawall/dock that wraps around the waterside of the property, including the boat basin with two boat lifts and a fish cleaning station. Relax in large pool with over-spill hot tub & a big pool patio area and a covered patio for entertaining, which drinks in the Ocean view. Interior features abound: wood cabinetry, granite, marble, and more. Double bronze doors adorn the entrance and foyer. There is a formal dining room off the kitchen. The master bedroom opens onto a porch, facing the Ocean. Soaring ceilings in the living room, with Casablanca style rotating fans. The upstairs level has a lovely deck that faces the Ocean, perfect to relax, enjoy the sunsets, and where you can see for miles and miles. Gated and fenced.

974 Flagship Drive, Summerland

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