Islamorada Real Estate

Welcome to Islamorada, a captivating village nestled in the heart of the Florida Keys, Monroe County. Known as the “Sportfishing Capital of the World,” this enchanting destination offers a unique blend of natural beauty, vibrant culture, and a relaxed island lifestyle that is simply irresistible.

Islamorada comprises a series of picturesque islands, each adorned with stunning beaches, crystal-clear waters, and lush tropical landscapes. Whether you’re an avid angler, a water sports enthusiast, or simply seeking a tranquil retreat, Islamorada has something for everyone. The warm, sunny climate invites you to explore its numerous outdoor activities, from kayaking through mangroves to diving in vibrant coral reefs teeming with marine life.

Beyond its natural allure, Islamorada boasts a rich history and a thriving artistic community. The village is home to charming boutiques, art galleries, and local eateries serving up fresh seafood and island-inspired cuisine. Don’t miss the chance to indulge in the local culture by attending one of the many festivals or events that celebrate the unique heritage of this coastal paradise.

Real estate in Islamorada offers a diverse range of options, from luxurious waterfront estates to cozy cottages tucked away in lush gardens. With its breathtaking sunsets and a laid-back lifestyle, living in Islamorada is like being on a permanent vacation.

If you’re seeking a place where adventure meets serenity, Islamorada is the perfect destination to call home. Discover the magic of island living and make your dreams come true in this tropical paradise!

Newest Listings in Islamorada

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 611801 MLS

Peaceful Palms - is a newly-built luxury coastal development situated in the gated community of Islamorada, FL. This upscale property features 15 high-end townhomes, all boasting an oceanfront location, as well as oceanfront views. You can enjoy spectacular views of the acclaimed Sandbar and Alligator Reef Lighthouse, as well as breathtaking sunrises. For boating enthusiasts, there are oceanfront docking facilities available for rent. Additional amenities include an oceanfront pool, making it an ideal location for a Florida Keys getaway and investment property. Once assessments and approvals have been completed this year, Peaceful Palms is set to cater to weekly vacation rentals, a rarity in Islamorada. Each townhome comes with three bedrooms, three bathrooms, a spacious garage, and balconies on the second and third floors with oceanfront views. Peaceful Palms is pet-friendly. The world-class fishing and diving opportunities of Islamorada are an added attraction. With the potential halt in issuing new building permits in the Florida Keys, investing in Peaceful Palms presents a unique and timely opportunity.

84745 Old Highway Unit #1, Islamorada

Listing Courtesy Of Your Home Sold Guaranteed Realty Services, Contact: (561) 221-2292

$1,700,000

3 Beds ⋅ 2 Baths ⋅ 611787 MLS

Discover the ultimate waterfront retreat in the heart of Islamorada, in the highly sought after neighborhood of White Marlin Beach. This captivating 3-bedroom, 2-bathroom gem is a dream come true. The interior features an open floor plan with 9-foot ceilings and ceramic tile. Embrace the coastal lifestyle with stunning water views right from your backyard and revel in the convenience of a private boat ramp and dock. Take a short trip just a couple blocks away to your private homeowner's park with sandy beach. Safety and security are paramount, thanks to the fully fenced yard with electric sliding gate and impact windows and doors. The one-car garage, carport and shop provide space for multiple vehicles and hobby projects.

121 Venetian Drive, Islamorada

Listing Courtesy Of TruRes Real Estate, Inc., Contact: (305) 820-2124

$950,000

3 Beds ⋅ 2 Baths ⋅ 611785 MLS

Welcome to Keys Cottage, a delightful haven nestled in the heart of Downtown Islamorada. This enchanting three-bedroom, two-bath residence exudes charm and offers an abundance of space for relaxation and entertainment. Savor your morning coffee on the inviting outdoor porch, surrounded by lush landscaping that enhances the serene atmosphere. The expansive front and backyard provide ample room for outdoor activities and gatherings. Ideally situated, you are just moments away from renowned dining establishments such as Ziggie & Mad Dog's, Chef Michaels, Pierre's, and Kaiyo Grill and Sushi. Experience the perfect blend of comfort and convenience in this idyllic retreat.

110 Knowles Street, Islamorada

Listing Courtesy Of Coldwell Banker Schmitt Real Estate Co., Contact: (305) 743-5181

$1,700,000

3 Beds ⋅ 2 Baths ⋅ A11674250 MLS ⋅ White Marlin Beach Sec 1 BLDG.

121 Venetian Dr, Islamorada

Listing Courtesy of TruRes Real Estate Inc., Contact:

$4,949,000

A11673748 MLS

This property features 3 acres of industrial upland, complemented by an additional 9 acres of bayfront land, which can be negotiated, including plans for a 100' dock and two 30k lb boat lifts. The property has 150 ft of US1 frontage and is conveniently located north of the weigh station. The Village of Islamorada officially recognizes 1,972 sq. ft. of non-residential floor area, one market-rate dwelling unit, and two affordable housing units. The current zoning code permits the construction of over 30,000 square feet, based on 3.12 acres or 10,000 sq. ft. per acre. Presently, there are four structures on the property. The seller is open to subdividing to meet the buyer's needs. This is one of the few properties in Monroe County with a wide range of potential uses, including residential.

86560 Overseas Hwy, Islamorada

Listing Courtesy of Real Estate Sales Force, Contact:

$6,999,000

5 Beds ⋅ 6 Baths ⋅ 611760 MLS

Welcome to Southwinds, your exclusive oceanfront oasis in the heart of Lower Matecumbe, Islamorada. This stunning 5-bedroom, 6.5-bath CBS home embodies luxury and tropical living. Spanning nearly 4,000 sq. ft., Southwinds offers breathtaking ocean views, with floor-to-ceiling impact windows that flood the interior with natural light, seamlessly connecting you to the stunning beauty of the Atlantic. One of the standout features of Southwinds is its 100' natural sandy beach, a rare find in Keys oceanfront homes. Stroll the 150' foot pier which features water, electric and a fish cleaning station. Read a book or enjoy your favorite beverage under the tiki. The pool features a spillover edge, bubbler, sun shelf and hot tub. The grand outdoor Mahogany bar is ideal for entertaining against the backdrop for the ocean breezes. A private pickleball court offers hours of fun and fitness for you and your guests, right in your own backyard. Paired with a putting green, this home provides a truly unique lifestyle experience that caters to the active, outdoor enthusiast.The home features a large kitchen with a pass-thru, an induction range, wine and beverage coolers, and two sets of washers and dryers for ultimate convenience. The third-floor wet bar and expansive open balconies offer additional space to enjoy the spectacular views. The gated property also features landscape lighting, an irrigation system, a spacious garage, and storage room.Southwinds is a sanctuary for those seeking a private retreat or a valuable investment. Whether you're in search of a second home or a high-performing rental property, this residence offers everything you could desire. Zoning allows for weekly vacation rentals, Southwinds presents an ideal opportunity for generating rental income.

75851 Overseas Highway, Islamorada

Listing Courtesy Of American Caribbean Real Estate, Christie's International Real Estate, Contact: (305) 664-4966

$2,450,000

2 Beds ⋅ 2 Baths ⋅ 611759 MLS

Welcome to this charming Old Florida-style cottage, an ideal weekend retreat nestled on Lower Matecumbe Key in Islamorada! This property is set on nearly half an acre, boasting an impressive 100 ft of private beach frontage directly on the crystal-clear ocean. This cottage is a perfect fixer-upper opportunity, offering you the chance to renovate and personalize the existing structure or build your dream home on this stunning piece of prime real estate. Step inside to discover two spacious bedrooms and two full bathrooms. The interior features beautiful beamed and tongue-and-groove ceilings, adding a touch of character and warmth to the space. Imagine starting your mornings with a cup of coffee or unwinding in the evenings with a glass of wine, all while enjoying breathtaking views of the magnificent Atlantic Ocean. The gentle ocean breezes create a serene atmosphere, perfect for quiet contemplation and entertaining friends and family. With its prime location and charming features, this cottage is a rare find that invites you to embrace the laid-back Florida Keys lifestyle. Don't miss your chance to make this idyllic getaway your own!

75621 Overseas Highway, Islamorada

Listing Courtesy Of Ocean Sotheby's International Realty, Contact: (305) 712-8888

$1,650,000

3 Beds ⋅ 3 Baths ⋅ 611751 MLS

This is it!! Your Florida Key Oasis! Quintessentially Key-z, this home has it all ... and then some. Located in the very desirable Indian Waterways Community of Tavernier on Plantation Key. Stylish Two Bedroom / Two Bath Main house plus a super inviting 1/1 guest house that your guests will never want to leave! Relax and entertain in the canal front Tiki hut as you enjoy tropical breezes. Cool off on the Custom Outdoor Shower after you dock your boat. Composite Dock ensures longtime enjoyment. And an Outstanding Double-sided Garage + storage room is a major Bonus!!! As Well as the personal boat ramp, that is perfect for launching/storing a flats boat, skiff, Jet Ski, or Kayak. Both the Main House and Guest House boast gorgeous, exposed wood-beamed ceilings that are gleaming works of Art. Large Bedrooms and stylishly updated Bathrooms. Great privacy with a nature preserve across the Street CBS Construction and a White Picket Fence add to the irresistible charm of this property that personifies 'Tropical Chic.' Super Close proximity to Tavernier Creek via the famous 'Toilet Set Cut'. World Class deep water, reef, and backcountry fishing are mere minutes away as are incredible diving, snorkeling, Lobstering, and sandbar-ing! Come Grab a slice of Florida Keys Living!

157 Caloosa Street, Islamorada

Listing Courtesy Of American Caribbean Real Estate, Christie's International Real Estate, Contact: (305) 664-4966

$415,000

611746 MLS

Fabulous Plantation Beach lot only 3 lots from the bayfront Homeowner's Park! This lot is currently #30 in BPAS system. Plantation Beach is a lovely neighborhood with bayfront and non waterfront homes. The Homeowner's Park is on the bay and features a boat ramp, jetty into the bay, roped off swimming area, volleyball court and kayak and paddleball racks. There is plenty of parking for your truck and trailer once you put your boat in the water. Make this your home in the Florida Keys!

133 Orange Lane, Islamorada

Listing Courtesy Of Coldwell Banker Schmitt Islamorada, Contact: (305) 664-4470

$775,000

2 Beds ⋅ 2 Baths ⋅ 611745 MLS

Fabulous top floor location with spectacular ocean views! This spacious condo has tile floors throughout and a lovely open terrace to enjoy the ocean view and breezes. Both bedrooms are spacious and the primary bedroom opens to the oceanfront terrace. The Palms of Islamorada is conveniently located close to the downtown Islamorada area. You are only minutes from enjoying shopping in the boutiques and galleries and eating in numerous restaurants that are very close by. The Palms has an oceanfront pool, hot tub, assigned parking with plenty of guest parking, 2 gyms as well as kayak and paddleboard storage. A fantastic view of Alligator Lighthouse is included at no extra cost.

79901 Overseas Highway Unit #512, Islamorada

Listing Courtesy Of Coldwell Banker Schmitt Islamorada, Contact: (305) 664-4470

$650,000

2 Beds ⋅ 3 Baths ⋅ 611729 MLS

Experience the ultimate Florida Keys lifestyle in this spacious 2-bedroom, 3-bath condo located in the highly sought-after, gated Executive Bay Club. With manned security for added peace of mind, this unit offers a versatile sleeping loft and a cozy office/sleeping nook, providing ample space for family and guests.The bright kitchen boasts granite countertops, stainless steel appliances, and a tankless hot water system. The master bedroom features its own private bathroom, while both bedrooms include plantation shutters for added privacy and style. You will enjoy this unit's close location to the pool and sandy beach, as well as easy access to community amenities like the clubhouse, dockage, and tennis and basketball courts--all just steps away from Founders Park, where local festivals and events take place throughout the year. Pet owners will appreciate that the community allows 2 approved pets, making it a perfect fit for animal lovers. Don't miss this fantastic opportunity--ask about the rental income potential!

87200 Overseas Highway Unit #M5, Islamorada

Listing Courtesy Of Still Water Properties, Contact: (813) 480-7411

$2,150,000

2 Beds ⋅ 3 Baths ⋅ 611664 MLS

RARE OPPORTUNITY to own an oceanfront home in the prestigious Anglers Reef development in Islamorada. Deeded boat slip accommodating up to a 31 ft boat included in offering. A beautiful 2-bedroom, 2.5-bath, 2-story home with 2 porches and a balcony overlooking the Atlantic Ocean. Located in the gated community of Anglers Reef on Windley Key approximately half way between Miami and Key West. This property contains 2 large bedroom suites with bathrooms on the 2nd floor. A living room, kitchen, dining room and powder room on the main level. Looks out on the community pool and marina (see included video). Upgrades include impact windows/doors, metal roof, composite decks/railings, granite counter tops with wood cabinets, tile floors downstairs and bamboo floors upstairs, shutters/blinds, brand new dishwasher and refrigerator. The community features 2 sandy beaches, pool, gated entry, marina, kayaks and paddle boards. Perfect home for primary residence, vacation family home or investment property. Call today for a showing

144 Anglers Way, Islamorada

Listing Courtesy Of BHHS Florida Realty, Contact: (954) 752-5100

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.