Islamorada, FL 2-Story Homes for Sale

Pickle Ball Estate is a stunning new luxury retreat in the heart of Islamorada, masterfully crafted by 4 Keys Construction. This brand-new four-bedroom, five-bathroom residence is a true standout, blending refined coastal design with resort-style living.Designed for both relaxation and entertainment, the home features a private pickleball court, making it a rare and exciting find in the Florida

Dominic Rivera Pine River Realty, LLC.

VA assumable!Experience refined waterfront living in the Florida Keys, where luxury meets effortless access to world-class boating and fishing. This exceptional canal-front residence is thoughtfully designed for discerning buyers who value privacy, convenience, and a true connection to the water. A private dock with newly added 15,000 lb boat lift provides seamless access to open water,

Caroline Hendrix Coldwell Banker Schmitt RE Co

Welcome to paradise. This tastefully redone 3-bd, 3 has it all + has a downstairs cabana lounging area great for flex space. This area with is not included in SF. Large carport area with 14ft ceilings. Property has a resort-style feel with its ideal waterfront location. With a bright interior, this property provides the perfect blend of comfort and Keys lifestyle. 50 ft private dock with trex

Kathleen Morris Compass Florida, LLC

Estate Opportunity - Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage,

Elizabeth Jolin Coldwell Banker Schmitt RE Co

Located in the private gated Seven Acres community, this three bedroom, three bathroom home sits on an approximately one third acre lot surrounded by mature tropical landscaping. Built for durability, the home features steel construction, a metal roof, Hardie board siding, and impact windows and doors. Inside, vaulted tongue and groove ceilings and hardwood floors create a warm and inviting feel.

David Jimenez Amp Realty Group, LLC

Welcome to coastal living in this two-story CBS construction home with concrete roof, impact doors and windows. This waterfront residence is designed for both relaxation and entertaining. Perfectly positioned on a deep-water canal, this home offers direct boat access to the ocean and a private dock with 10,000 lb boat lift. This home has 3 bedrooms and 3 full bathrooms. The kitchen has custom

James Ruggles The Keyes Company

New construction waterfront residence featuring quality material and modern design throughout. This home offers impact-resistant doors and windows, a garage, and open living spaces designed for comfortable coastal living. Outdoor amenities include a private pool, built-in grill area, and approximately 45-foot dock providing convenient boating access. Constructed with high-quality materials and

Merlin Perez Golden International Realty Corp

Experience true oceanfront living in the Florida Keys with this exceptional home in Tavernier. Showcasing breathtaking 180-degree ocean views, this property offers a front-row seat to some of the most stunning scenery in the Keys—all from the comfort of your own deck. Set on a rare, expansive lot, there’s ample space to entertain family and friends, making it perfect for gatherings and relaxing

Christian Salgado MDZ Realty, LLC.

Ocean views, deepwater dockage, and the rare ability to legally operate nightly rentals. This exceptional oceanfront duplex offers a standout turnkey investment opportunity, combining the perfect trifecta for your portfolio: panoramic ocean views, deepwater dockage, and approved nightly rental capability. An ideal multi-family compound and a rare chance to own a fully versatile, income-producing

Amy Bruggeman American Caribbean Real Estate

A rare architectural masterpiece by renowned architect Max Strang, this modern coastal estate in Port Antigua, Islamorada, redefines luxury waterfront living. Set on a private sandy beach, the residence offers 5 bedrooms, 6 full baths and 2 half baths across 6,367 SF of interior space and 10,483 total SF. Strang’s signature tropical modernist design showcases natural materials, clean lines, and

Angel Nicolas Serhant

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWSWelcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters. The

Steven Koleno Beycome of Florida LLC

Solid Concrete Home - Steps from Harry Harris Park!This beautifully updated 4Bedroom/2Bathroom concrete home with a concrete roof offers everything you've been looking for. Upstairs features 2 bedrooms and 1 bath with a wraparound screened porch, while downstairs provides another 2/1 with its own screened patio — ideal for guests or family. The chef's kitchen boasts quartz countertops, new

Tracey Petrusha LoKation

ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community that allows Vacation Rentals, This home features 2 bedrooms, 2.5 bathrooms with carport & 4 porches. Upgrades include Brazilian Cherry hardwood floors, kitchen with granite countertops and SS appliances with 2 breakfast bars & tons of cabinet space. The home also has a composite decking, metal roof & impact

Scott Ofstein Berkshire Hathaway Florida Realty

Beautifully renovated 3-bedroom, 2-bathroom home in desirable IndianHarbor, this property has been completely updated with high-end finishes and thoughtful details throughout.Open-concept living area and kitchen, The house features new large impact windows and a layout that utilized all of the space. The kitchen features brand-new stainless-steel appliances, custom cabinetry, quartzite

Steven Koleno BEYCOME OF FLORIDA LLC

Set on 1.38 acres of pristine oceanfront in the Florida Keys, this private estate offers the perfect blend of luxury, serenity, and tropical beauty. With an enormous 150-foot private beach, this stunning 4,770-square-foot residence presents an unparalleled opportunity to experience the magic of oceanfront living.The home features five bedrooms and five and a half baths, including separate guest

Annie Hagen Ocean Sothebys Intl Realty

Rare find at the Anchor Condominium! These units rarely come on the market, making this two-bedroom, one-and-a-half-bath condo a truly exceptional opportunity. Located at mile marker 92.5, this property sits perfectly between the vibrant atmosphere of Key Largo and the charm of Islamorada. The home features impact-resistant windows and sliders, and the building roof was replaced in late 2024. The

Margaret Crowley Florida Keys Realty Group

Turnkey Florida Keys retreat, already approved for short-term rentals! This amazing 5-bedroom, 3-bathroom home is the perfect blend of luxury lifestyle and income potential. Whether you're an investor seeking strong returns, a buyer looking for a vacation home, or planning your dream retirement in paradise, NO HOA . Comes with solar panels that save you $$$ Impact door and windows and beautiful

Adriana Gonzalez Dalton Wade Inc

Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene. The home enjoys unobstructed water views and nightly sunsets that paint the sky in

Judy Rossignol Paradise Florida Keys Real Est

Private location for your pleasure at this roomy townhouse offering an abundance of space to enjoy. Spiral stairs leading to the primary suites with an additional loft for your quests. Soft carpet on the living area floors with tile in the remodeled kitchen and beautiful bathrooms. Two pets allowed, with first come first serve the waterfront area. Pool and club house for your recreation along

Barbara Eads Barbara Eads Realty Inc.

Nestled in the Safety Harbor enclave, Islamorada, this stunning Gulfside estate offers unparalleled blend of luxury and tranquility. Situated on a prime point w/open water and protected dockage, makes this a boater's paradise. With concrete seawall/2 boat lifts this home is appointed for waterfront living. Easy ocean access through Channel 5. Home features 8 ensuite BRs plus 2 half BAs. The

Nancy Muniz Coldwell Banker Realty

CANAL FRONT - DIRECT OCEAN ACCESS!! Welcome to an experience in lifestyle. Coveted by many but enjoyed by a select few, this unique upper Keys location is surrounded by protected land preserving the natural beauty of these beautiful islands! The cut in dock basin complete with a 10k boat lift makes those days on the water a breeze. Coastal luxury is the theme on the main level from the kitchen's

Susan Holler LoKation

ANCHOR IN PARADISE- 4 BEDROOM, 2 BATH IN ISLAMORADA- EXECUTIVE BAY CLUB, THIS IMMACULATE CONDO WILL CONVEY FULLY FURNISHED ALL COMPLETELY RENOVATED & UPDATED W/HURRICANE IMPACT WINDOWS, SLIDING GLASS DOORS, WASHER/DRYER DOWNSTAIRS. PERFECT RETREAT W/SANDY BEACH, POOL, TENNIS COURTS, CLUBHOUSE FOR GATHERINGS, DOCKAGE AVAILABLE, BRAND NEW ONSITE MARINA, WALKING DISTANCE TO 'FOUNDER'S PARK' & FINE

Lidia Yoham Anchor Realty of FL, LLC.

Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfront estate offering rare privacy and breathtaking natural beauty in the heart of Islamorada. Set on over an acre of lush tropical land, this coastal retreat boasts 165 feet of private sandy Atlantic beach, where you can launch a kayak or paddleboard right from your backyard and soak in endless turquoise

Joy Martin American Caribbean Real Estate

Experience luxury waterfront living in the heart of the Florida Keys! 4 bedrooms and 2 bathrooms. This stunning modern home offers sleek finishes, breathtaking canal views, and direct boating access. Enjoy the spacious outdoor entertainment area, complete with a private dock, lush synthetic turf, and a large jacuzzi—perfect for relaxing under the stars. The upper-level terrace provides an ideal

Dahiana Rojas de Rojas Canvas Real Estate

Boater’s dream home in White Marlin Beach, Islamorada. Unique 2-story single-family home with split layout, two 800 square feet 2BD/1BA units. Separate entrances and laundry in each unit, 70' dock with private boat ramp on a tranquil mangrove canal. This property is facing mangrove with maximum privacy, just 7 homes from the bay! Plenty of parking for RVs/trailers. Enjoy access to the White

Po Yen Hsueh Compass Florida, LLC

Your dream getaway in the heart of the Florida Keys! This light-filled, spacious 2br/2bth home is located in the highly sought-after Angler's Reef community in Islamorada. Fully furnished, tastefully decorated and turnkey, this well-maintained property is perfect for ocean lovers or savvy investors alike.With over 12 years in a successful vacation rental program and an active vacation rental

Rosana Velilla Serrano & Associates Real Estate, LLC

Great opportunity here at this immaculate three-bedroom two bath home. Beautiful marble kitchen counter tops accented with white cabinets and stainless-steel appliances. Vaulted ceilings with roomy bedrooms and glass sliding shower doors in the primary suite. Metal roof with modern window treatments and tile floors throughout this well-kept family home. Open patio to enjoy your morning coffee and

Barbara Eads Barbara Eads Realty Inc.

"Blue Haven" is a beautifully renovated elevated 2-story residence in the heart of Islamorada, offering the ideal blend of modern upgrades and relaxed Florida Keys living. This fully remodeled home features a vibrant blue exterior and a bright, contemporary interior designed for comfort and style. The home offers 3 bedrooms and 2.5 bathrooms, with nearly 1,700 square feet of interior living space

Andres Navarro Harbour Residential Realty LLC