Islamorada Florida Real Estate

LIVE, WORK & PLAY IN ISLAMORADA | RARE SC COMBO ZONING! Income + residence at MM 82.8 on high-visibility Overseas Hwy! Walk to beach, shops & dining. Street-to-street 50x150 lot w/ Old Hwy rear access & parking for work trucks, trailers & boats. COMMERCIAL OFFICE: Fully outfitted CBS bldg w/ 6" concrete roof, dual mini-splits, full bath, separate meter, 3-phase electric & impact shutters.

Exceptional investment and lifestyle opportunity in the heart of Plantation Key. This offering includes a triplex income property together with the adjacent multifamily lot, giving you both immediate rental income and room to grow. In Islamorada, it's rare to find side-by-side multifamily parcels in such a convenient, desirable neighborhood.

Waterfront Islamorada Pool Home with Private Beach Access & New 60' Dock. Experience the best of the Florida Keys in this beautifully updated waterfront retreat in Islamorada, accommodating up to 12 guests and ideal for family vacations, multigenerational gatherings, or extended stays.

10,000 SF open warehouse-style space available in the heart of Islamorada. The space features expansive interior floor area, two offices, modern multi-stall bathrooms. Five oversized loading doors provide substantial clearance, easy access and excellent natural light.

74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access.

WAKE UP TO A BREATHTAKING OCEAN VIEW IN THIS RARELY AVAILABLE OCEANFRONT CONDO COMMUNITY! LOCATED ON MILLIONAIRE'S ROW IN HIGHLY DESIRABLE ISLAMORADA/PLANTATION KEY. ENJOY A SPARKLING OCEANFRONT HEATED POOL, A 300 FT FISHING PIER/DOCK TO TIE UP YOUR BOAT FOR LOADING AND UNLOADING. KAYAK STANDS FOR THOSE THAT PREFER NON MOTORIZED ACTIVITIES.

Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islamorada, which is recognized as ''The Sport Fishing Capital of the World''. Islamorada is renowned for fine dining, water sports, The Art District, galleries, shopping and breweries.

Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and native birdlife, the property offers boating access to both Florida Bay and the Atlantic Ocean.

Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre of bayfront property, a dramatic arrival unfolds beneath soaring 30ft ceilings, leading into a grand living space framed by turquoise bay views.

OCEAN ACCESS WATERFRONT OPPORTUNITY IN VENETIAN SHORES! Immaculate 2-story CBS concrete home offering the ultimate Florida Keys lifestyle! Situated on a 100' wide deep-water canal with NO FIXED BRIDGES and direct access to both the Atlantic Ocean and Florida Bay via Snake Creek, this is a boater's dream. Minutes to open water with a private dock featuring power and davits, perfect for large boats.

A truly once in a generation opportunity to build your dream estate in the heart of Islamorada's coveted Lower Matecumbe. This exceptional vacant homesite is one of the few remaining parcels of its size available in all of Islamorada, offering an incredibly rare combination of breathtaking ocean views and expansive wide canal views.

Private Bayfront Estate in desirable Islamorada offering a serene ambiance on an oversized parcel of pristine bayfront with breathtaking sunsets and unobstructed panoramic views of the Florida Bay. This exceptional waterfront retreat features an irreplaceable protected boat basin, concrete jetty, and T-dock providing superior deep-water dockage.

This island resort unit offers stations for dockage up to 25-foot boats daytime only, trailer storage and boat ramp. There is a pool for the development, pickle ball and tennis courts. The unit has hurricane impact windows as well as updated balcony area. It offers a large garage area with plenty of storage space. Injoy island living in the Keys .

Move-in ready townhouse located in the heart of Islamorada! This 2-bedroom, 1.5-bath home has been well maintained and features impact windows and doors, fresh interior paint, a metal roof in 2024, newer AC, upgraded electrical throughout and a washer and dryer in the unit. The galley kitchen provides ample cabinet space, induction stove top, dishwasher and pantry.

TURN KEY Canal-Front Islamorada Home with Pool, Dock & Private Beach Access Luxury canal-front home in Islamorada offering spacious living, refined coastal design, and exceptional outdoor amenities. This meticulously maintained residence features a flexible split floor plan with a main-level living area, wet bar, bedroom, and full bath overlooking the outdoor kitchen and resort-style pool.

Islamorada top-floor condo at Ocean Harbour with Atlantic ocean views and a boat slip. 3 bedroom, 2 bathroom luxury condo offers expansive ocean views and comfortable living space.

Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly four acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury.

Escape to your own slice of paradise with this cozy and beautifully kept 1-bedroom, 1-bath Jayco RV. Whether you're looking for a peaceful weekend retreat, a seasonal getaway, or a spot with great rental potential, this charming hideaway has it all. Wake up to the soothing sounds of the Atlantic and enjoy unforgettable sunrises and sunsets right from the jetty.

LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand-new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pristine bayfront offering deep-water dockage with a 20,000 lb boat lift, a white sandy beach and stunning unobstructed panoramic views of the Florida Bay located in desirable Lower Matecumbe.

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available.Experience luxury coastal living at its finest in this exceptional Gated bayfront estate, ideally situated in the heart of Islamorada.

Big, beautiful, and exceptionally solid, this waterfront Islamorada residence is perfectly situated on Sandy Cove Basin with protected deep-water dockage for multiple boats and direct bay access. A gated, pavered double driveway leads to an inviting foyer where marble floors and a private elevator welcome you.

A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a protected deepwater basin. Designed for elevated living, The Oasis blends resort-style amenities with the privacy and scale of a true Florida Keys compound.

Newly completed in 2025, this exceptional oceanfront estate is located in the heart of The Florida Keys on the premier ocean side of Islamorada. A gated entry welcomes you through lush tropical landscaping and a diverse fruit-tree grove, setting a private and refined arrival.

Experience unparalleled oceanfront living at Chateau On The Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami.

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.

Spectacular Direct Ocean Views! Islamorada's Best-Kept Secret! This beautifully appointed 2-bedroom, 2-bath residence offers breathtaking, unobstructed ocean views from your private waterfront balcony. Step outside and enjoy a refreshing swim in the oceanfront pool or take a dip directly in the crystal-clear Atlantic.

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.

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.

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 views.

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.

Rarely available, turnkey Deepwater Boater's Retreat with Private Beach Access in the Heart of IslamoradaTucked away on a quiet cul-de-sac in one of the most desirable enclaves in Islamorada, this fully designer-updated 3+ bedroom, 3.5-bath home delivers the ultimate Florida Keys lifestyle--where luxury, durability, and world-class boating converge.

Simply the best location, exclusive & extremely private. It's tucked away in the prestigious "Plantation Lake Estates," a highly sought-after gated community with an on-site boat ramp and park.

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.

Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a cozy loft. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area - ideal for entertaining.

This exceptional canal-front vacant lot on Lower Matecumbe Key represents a truly prime piece of cleared real estate. The permit for this property is being picked up 6/12/26. Seize this rare opportunity to build your dream home in a highly sought-after Keys location.

Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Great vacation and income producing condotel in the Sport Fishing Capital of the World.

A New Standard of Paradise - Live with views of the Atlantic Ocean everyday. This home has been updated and beautified from top to bottom. Marble flooring throughout living areas. Eat in kitchen offers large island, snack counter and full size wine cooler. Dishwasher installed 12/25. There is also a hot water dispenser.

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.

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.