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$699,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 88
Condo - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: None

LOVE AT FIRST SIGHT! This is an Unbelievable opportunity to own a TURN KEY unit at The Palms of Islamorada. Endless views of the Atlantic Ocean including Alligator Reef Lighthouse from the balcony or the over 200 feet of seawall. Unit comes completely furnished - ready to move in or rent. Conveniently located within walking distance to fine dining with sunset views, marinas and dive opportunities. All you need to settle into this exceptional unit are your personal items. Everything is done and ready for you. All furnishings, linens, kitchen essentials and artwork are included. There are two large bedrooms both with king size beds. The master suite features a full wall of built-in closets and drawers hidden behind attractive sliding cabinet style and mirrored doors. The ensuite bath is completely updated featuring a Jacuzzi jetted bathtub, large tiled stall shower, and a double vanity - your own PRIVATE spa! The 2nd bedroom area has a king bed, full closet, private updated bathroom and pocket door for a private experience for your guests. The kitchen has everything...updated cabinets in todays colors, new Cambria quartz countertop and all newer stainless-steel appliances. You will love having your own new Bosch stack front loading washer and dryer in the unit. The kitchen offers casual dining with 4 bar stools for casual dining at the counter and youll love the hand carved teak dining table for more formal dining. The living room seating provides a cozy place to relax after a hard day of fishing and diving. The balcony overlooking the ocean presents endless views of the ocean and comfortable outdoor furnishings. Hurricane impact certified. Passed the Milestone inspection. Covered parking space. EVERYTHING is included!!The Palms is one of the most sought-after condo complexes in the Islamorada area due to the unparalleled ocean views. There have been very few units for sale in the past several years. Now is your opportunity to own one!

$725,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 550 SqFt Days Listed: 408
Condotel - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

***Seller Financing now an option! ***Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the Sportfishing Capital of the World. Condo Features -This spacious King Bed Suite offers a large living room area with a pull-out queen bed, a grand bathroom with walk-in shower and soaking tub, a fully equipped kitchenette, and a private screened in porch with views of the lush landscape and large coconut palms. This exceptional income-producing property allows nightly rentals. Owners use their units up to 28 days a year and receive a monthly check for the remainder of the time. Its a hands-off income generator!The Resort -Enjoy 27 acres of Islamorada oceanfront that include 3 world class restaurants, 2 open-air tiki bars, 1,200 of private beach, 525 fishing pier, 2 family pools, 1 adults only pool, beach and pool side cabanas, 9 hole golf course designed by Jack Nicklaus, 6 sports courts, 15,000 sqft of event space, valet parking, 24 hour shuttle service, concierge service, on site boat trailer parking, watersports activities, fitness center and Camp Cheeca.

$725,000
Upper Matecumbe Key Islamorada
Palms Of Isla   - MM: 80.00
2 Bed, 2 Baths, 981 SqFt Days Listed: 253
-6.45% ($50,000) 1 Price Change : Last Change 2 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

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.

$1,200,000
Upper Matecumbe Key Islamorada
Beacon Reef   - MM: 83.00
2 Bed, 2 Baths, 1,275 SqFt Days Listed: 37
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Boat

Welcome to Unit #409 at Beacon Reef, an oceanfront gem located in the heart of Islamorada. Beacon Reef is well-run, meticulously maintained, and units are rarely available for a reason. This beautifully appointed 2-bedroom, 2-bathroom residence offers approximately 1,275 square feet of comfortable, coastal living. The primary suite features a king-sized bed, en-suite bathroom, and direct access to a private balcony with sweeping ocean views, while the guest bedroom provides space for two queen-sized beds and a generous closet. The open-concept living area flows effortlessly into a fully equipped kitchen with granite countertops, and a breakfast bar, complemented by a formal dining area. Additional conveniences include an in unit laundry area with full-sized washer and dryer, impact windows, and a spacious screened-in balcony.Beacon Reef is a gated, resort-style community offering a wealth of amenities, including a beach-entry heated pool, therapeutic hot tub, ocean-view fitness center, and a deep water private marina with boat slips available for vessels up to 35 feet (first-come, first-served). Residents also enjoy a sandy beach, fishing pier, BBQ area under the tiki hut, and lush tropical landscaping throughout the property. Ideally located, this unit is just minutes from Islamoradas world-class fishing, diving, restaurants, galleries, and marine attractions, offering both seclusion and convenience. Whether youre seeking a permanent residence, weekend retreat, or seasonal getaway, Unit #409 is your invitation to live the Florida Keys lifestyle.

$2,850,000
Upper Matecumbe Key Islamorada
Tarpon Flats   - MM: 81.50
3 Bed, 3 Baths, 2,072 SqFt Days Listed: 33
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock150ft

Experience refined coastal living at Tarpon Flats, Islamoradas most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the charm of Old Florida meets the timeless elegance of Nantucket.This three-story home offers a thoughtful layout and spectacular bay views throughout. The ground floor features covered parking, a versatile multi-purpose room, and access through a gracious foyer entry. Upstairs, the main living level boasts an open-concept kitchen and dining area with panoramic bay vistas, two bedrooms, two bathrooms, and a tranquil porch ideal for enjoying sunset skies. The top floor is reserved for the expansive master suite, complete with a private balcony and sweeping waterfront views.Tarpon Flats offers an amenity-rich lifestyle tailored to the discerning buyer. Enjoy a waterfront pool and gazebo, private beachfront access, generous dockage for your skiff, a charming greenhouse, and a tennis court with shaded seating for guests. Adding to the ease of ownership, the community provides a full-time concierge service and an on-site handyman, ensuring both comfort and convenience year-round. Sophistication, privacy, and natural beauty converge in this exceptional Islamorada retreat--come discover what makes Tarpon Flats truly one of a kind.

$2,950,000
Upper Matecumbe Key Islamorada
Bay Colony Villas   - MM: 81.50
4 Bed, 4 Baths, 2,072 SqFt Days Listed: 138
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock150ft

Only sophistication and class represented in Islamoradas most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off its manicured landscaping. One of only 12 luxury bayfront homes on a sprawling four-acre parcel. The property exudes a unique charm blending Old Florida allure with the timeless essence of Nantucket. Covered parking and a versatile multi-purpose room on the ground floor with a foyer entry. On the second floor you will find an open living space with the kitchen & dining room overlooking the bay, 2 bedrooms/2 bathrooms, and serene positioning for nightly sunsets. The third floor is dedicated to the master suite and maids quarters with more amazing views from the private balcony. If amenities are what youre after, Tarpon Flats delivers on all fronts: a beautiful tennis court with covered seating for spectators, a rare greenhouse to nurture your beloved plants, a waterfront pool & gazebo leading down to the beachfront, and plenty of dockage for your skiff. Come see the exclusivity of Tarpon Flats for yourself.

$3,150,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
4 Bed, 4 Baths, 2,576 SqFt Days Listed: 822
-1.56% ($50,000) 2 Price Changes : Last Change 133 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 400ft.

NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenance concrete block construction, this home has been built above flood level. Spacious living area of more than 2,500 square feet, with fully collapsing Euro doors both on the second floor, leading out to a covered balcony, and on the first floor, opening to the private pool and deck, Oceanside House 6 boasts four bedrooms with ensuite baths, plus a first floor powder room. Large open kitchen, island and living area flow seamlessly. The property also allows vacation rentals. This beauty will not last! Make an appointment to visit the site today.Owner is Florida licensed real estate agent.

$3,995,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
1 Bed, 1 Baths, 946 SqFt Days Listed: 176
-16.77% ($805,000) 8 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 65ft.

This remarkable 34,000 sq ft lot on the Florida Bay is a true paradise for anyone seeking a waterfront lifestyle in the heart of Islamorada, specifically Upper Matecumbe. With expansive open water views, this property offers an idyllic setting to enjoy the natural beauty of the Florida Bay. One of the key highlights of the lot is its exceptional dockage (65 ft), which has previously accommodated a 36-foot Bertram, making it perfect for boating enthusiasts. The property also offers ample space for a pool and garage, allowing for a customized design that maximizes the waterfront experience. Beautiful sunsets grace the horizon, casting vibrant colors across the water and clouds, creating a tranquil atmosphere for evening relaxation. The lot is also a sanctuary for wildlife enthusiasts, with an abundance of aquatic species, like fish, birds, manatees, and a multitude of different birds. Its a perfect canvas for your dream residence or vacation retreat. With easy access to the Atlantic Ocean and iconic spots like Alligator Reef, whether you prefer fishing, diving, or simply unwinding by the water, this property is one of the best on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation. May also purchase the vacant lot up front that has a Market Rate TDR on it. Combined you would have ability to build 2 large homes on a combined 49,000 of land. This would make an exceptional family compound in the heart of Islamorada. Possible owner financing. Owner / Agent

$3,995,000
Upper Matecumbe Key Islamorada
Caribee Beach   - MM: 80.00
2 Bed, 2 Baths, 1,578 SqFt Days Listed: 29
-6.00% ($255,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Seize the rare opportunity to build your dream home in one of Islamoradas most coveted locations! Located directly across from the iconic Alligator Reef Lighthouse. Across the street from a protected preserve that will never be developed, and featuring a deep water channel capable of accommodating boats up to 40 feet, this property offers unmatched privacy and access.Imagine living just a short stroll from the legendary Square Grouper, Midway Cafe, Robbies. Down the road from some of the best restaurants in Islamorada like Ziggies, Mad Dogs, and Chef Michaels. This oversized lot, just shy of an acre, provides the perfect canvas for a builder, developer, or savvy end user to craft a stunning, custom-designed home in an unparalleled location. Dont miss your chance to secure this exceptional piece of paradisean extraordinary opportunity to live where others only dream!

$4,250,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
4 Bed, 4 Baths, 2,574 SqFt Days Listed: 68
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

$5,299,000
Upper Matecumbe Key Islamorada
Venetian Shores   - MM: 86.00
6 Bed, 6 Baths, 4,964 SqFt Days Listed: 94
-3.64% ($200,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift100f

Exquisite Tri-Level Waterfront Estate in Islamorada!Step into luxury with this remarkable home in the prestigious Venetian Shores, designed for the most discerning buyer. Offering six bedrooms, five bathrooms, and a spacious 5000sqft of magnificently designed living space, this residence boasts an open-concept floor plan with soaring ceilings, a fireplace and a grand living area.Enjoy seamless indoor-outdoor living with an expansive wraparound veranda, perfect for soaking in the breeze and relaxing water views. The beautifully landscaped 10,000sqft lot provides privacy and tranquility, while the swimming pool offers the ultimate relaxation.For boating enthusiasts, this property is a dream come true! Featuring 100 of deep-water concrete dockage equipped with a 20,000lb catamaran width elevator boat lift and a 5500lb set of davits you will enjoy immediate access to both the Atlantic Ocean and Florida Bay for excellent offshore and backcountry fishing. A two-car garage with a new A/C unit, plus additional covered carport parking, ensures ample space for vehicles and storage along with a beautifully paved driveway.Come experience the best of the Florida Keys lifestyle in this exceptional waterfront retreat!Updates....1. NEW 2-car Air Conditioning Split with 10-year warranty2. New Dock and Stair Brick Pavers3. New third-floor Impact Windows4. Two New third-floor Impact French Doors5. Two New third-floor electric Rolladen Hurricane Shutters6. Swimming poll resurfacing with new glass edge surround7. Dock has a 220-volt pedestal to service dock-side marine electric needs

$5,990,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
4 Bed, 4 Baths, 2,574 SqFt Days Listed: 68
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock,Basi

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

$5,990,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
4 Bed, 4 Baths, 2,574 SqFt Days Listed: 68
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

$6,395,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 3,019 SqFt Days Listed: 5
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.

Seeking privacy, luxury AND convenience? This custom bayfront estate built by the current owner in 2014 offers it all! Situated on a peninsula with 250+ feet of crystal-clear open water frontage, this one-of-a-kind Keys home is located in the heart of Islamorada within walking distance of all your favorite local dining spots. As you enter the gated estate, you are welcomed home by unparalleled privacy and seclusion. This open water home has no neighbors looking through side yards and of course, no neighbors across a canal. Designed to offer the ultimate combination of location, deep-water dockage, storm resiliency and open water views, this luxurious home also boasts marble floors throughout and a gorgeous floating staircase. Begin your day by stepping out of your bedroom to your private bayfront terrace and into a stunning second floor Infinity Edge pool, complete with a heater/chiller. In the evening, experience the brilliance of Islamoradas sunsets from every room, the rooftop or outdoor lanais, which provide a grand total of almost 6,000 sf of combined indoor and outdoor living space. Floor-to-ceiling sliding glass doors disappear into pockets, bringing the indoors out and the outdoors in. Just one step outside the main kitchen is a full outdoor kitchen and bayside dining, al fresco. For stargazing, venture up to the rooftop deck for a breathtaking front row seat. Ready to get on the water? Your boats will comfortably berth on the 100 deep water dock with two lifts and are kept safe by built-in storm protection. Other functional luxuries include an elevator, an enormous three-car 2,200 sf garage with workshop/storage, camera/security system and mature landscaping with fruit trees. A fourth bedroom with bath can be easily added without modifying the structure at a reasonable cost. With all living space above flood and built to withstand sustained 200 mph winds, this concrete home has accordion shutters over impact for ultimate storm resiliency. Call today!

$6,750,000
Upper Matecumbe Key Islamorada
The Russell Estates   - MM: 83.50
6 Bed, 6 Baths, 4,566 SqFt Days Listed: 167
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

This breathtaking three-story beachfront home boasts six spacious bedrooms and five lavish bathrooms and three living rooms, perfectly blending resort-style living with the utmost comfort. Located in a serene cove with a pristine natural beach, the home features floor-to-ceiling windows that offer stunning 180-degree panoramic views of the ocean. Every corner is meticulously designed with tasteful decor, exuding elegance while providing a personal, comfortable atmosphere. The property is in downtown Islamorada, Florida Keys, and includes a private beachfront terrace, a third-story private balcony, and a tranquil pool with a tiki hut, making it ideal for relaxation and entertaining. The outdoor spaces feature a cozy firepit, offering the perfect setting for intimate gatherings with the sound of the waves as a backdrop. As a vacation rental, this residence is a lucrative investment opportunity in a highly sought-after area. This home is a true masterpiece, offering unparalleled luxury, privacy, and breathtaking views.

$9,650,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
6 Bed, 6 Baths, 6,866 SqFt Days Listed: 328
-10.23% ($1,100,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,BasinConcr

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms and one bathroom. The kitchen features marble countertops, a gas range, and counter seating. With a separate dining area and 30 ft high ceilings in the great room, floor-to-ceiling windows offer breathtaking views of the bay waters and dynamic sunset skies. The infinity edge pool with a spa offers reflections of beautiful palms and exquisite landscaping. The outdoor cabana kitchen is perfect for al fresco dining, and the boat basin with dockage allows for easy access to the waters of Florida Bay. A whole-house generator ensures uninterrupted comfort and tiki torches light the backyard terraces. Dont miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

$25,000,000
Upper Matecumbe Key Islamorada
Russell Estates   - MM: 83.20
7 Bed, 7 Baths, 6,935 SqFt Days Listed: 150
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Basin,Boat

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 4 acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury. An expansive infinity-edge pool blends seamlessly into the sparkling waters of the bay while lush gardens create a serene oasis. The homes architecture showcases graceful, custom finishes and rich hardwoods, all hallmarks designs that evoke the spirit of the Islands. Spanning over 6,900 square feet, the interior is a seamless fusion of open-concept living spaces and private retreats. Soaring vaulted ceilings and vast windows invite abundant natural light and spectacular views of the bay, creating an indoor-outdoor flow. The primary suite serves as your personal sanctuary, complete with private terrace, spa-inspired bathroom, and walk-in closets fit for a connoisseur of fine living. Each guest has direct access to outdoor spaces and views. A bonus, versatile bunk room/media center sits just off the west wing of the home. The charming guest house is the perfect complement to the main home, nestled in its own secluded on site location this delightful addition exudes a warm, welcoming ambiance ideal for hosting guests, or as a private office or creative studio. This downtown Islamorada estate in an incomparable location; walking distance to shopping, dining, and local culture, also has appeal that extends to those with a passion for the great outdoors. Two protected docking basins and boat lift, sandy lounging beach, expansive outdoor lanai and outdoor kitchen offers the ideal space for entertaining or enjoying a quiet evening watching the sunset. Fly the seaplane in or land the helicopter. Premier boating access just moments away from the Intracoastal waterway and Ocean channels. Serenity Cay is not just a home, its an experience.

$29,500,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
5 Bed, 5 Baths, 8,680 SqFt Days Listed: 68
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 100ft.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 06-15-2025.
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