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$1,895,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,804 SqFt Days Listed: 62
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 60ft.

Welcome to White Marlin -- a true fishermans paradise! Step into this beautiful 3-bedroom, 3-bathroom coastal retreat, featuring an open-concept design perfect for relaxing or entertaining. The expansive kitchen with tile countertops offers ample space, and the screened-in balcony lets you enjoy serene views without interruptions. Outside, youll find a 60-foot concrete dock and boat ramp, ideal for fishing enthusiasts, and a refreshing pool to cool off after a day on the water. With a propane backup generator for peace of mind, youre ready for any occasion. Unwind on your private beach and savor breathtaking sunsets over turquoise waters -- a slice of paradise awaits you here!

$1,799,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
3 Bed, 3 Baths, 1,680 SqFt Days Listed: 21
Townhouse - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: First Come Dock130ft

Little Basin Key Lime Villa #3 is a beautifully appointed, 3 bedroom, 3.5 bath townhome with proven rental income. Nestled amongst a quaint row of rocking chair adorned porches, this residences design takes inspiration from Old Town Key West and features postcard views of sunset from deck and docks. The immaculate, tropically landscaped grounds lead to the shared dockage, pool, tiki hut, and cabana. Parrot fish and mangrove snapper swirl around the waterfront with room for boats up to 30 ft, and a floating dock for guest use. Located on Upper Matecumbe Key, Bayside, in the Heart of Islamorada, the compound is right next door to Library Beach and is situated within walking distance to the best local sunset venues in the American Caribbean. Watch Sunset Celebrations each day and Full Moon Parties each month from your private porch! Across, on the Oceanside of the island, The Morada Way Art Walk is every Third Thursday and many local boutiques, breweries and fine dining restaurants are within walking distance. The first floor is designed in an open concept with soaring ceilings featuring dining area, kitchen, half bath and guest bedroom with ensuite bathroom. Upstairs leads to two more bedrooms with ensuite bathroom, and the master bedroom features french doors leading to lovely covered porches. Fully furnished in immaculate white decor - come stay for a week .... or, forever! Boats up to 30 allowed at dock on a first come, first serve basis. Note: Easy to show! Agent must accompany.

$1,695,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 1,782 SqFt Days Listed: 70
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift40ft.

Venetian Shores - the Upper Keys most coveted boating neighborhood. Immediate bay access and *very quick* ocean access via Snake Creek! An absolutely stunning home - ground level and above flood. CBS, metal roof, impact windows and doors, irrigation, 18K# boat lift and and low maintenance yard adds up to all fun and no honey-do list. Enjoy the serenity of your backyard on this plugged canal just a block away from your (permanent) slip in the private Venetian Shores marina. Lift in place! High quality renovation of the bathrooms, chefs kitchen with gas cooktop and Thermador appliances! This is a must see. Slip #25 will hold up to a 40 boat LOA.

$1,685,900
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,920 SqFt Days Listed: 133
-0.83% ($14,100) 1 Price Change : Last Change 48 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.Concrete

Incoming producing property with future bookings already in place! This two story-waterfront property in the Florida Keys within Lower Matecumbe Key (near mile marker 74) 3 bedrooms and 3 baths total (2 bed/1bath on the second floor, 1bed/1bath on first floor, and 1 full bath on exterior) on the ocean side with 1,920 sq ft of living space. Second floor has 2 bedrooms, 1 bath and first floor has 1 bedroom and 1 bath with an additional full bathroom on the exterior of the property. This unique canal front property offers a 6,600 sq ft total lot size with access to the open ocean and bay within minutes. 60 FT concrete dock offers space for your boats, jets skis and more. 2 boat lifts included in the purchase, one can hold up to 10,000 lbs and other 15,000 lbs. Plenty of parking for multiple cars within the actual property. Furniture can be included in the sale. Call us today for in-person/virtual showings.

$1,660,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,380 SqFt Days Listed: 8
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 18ft.

BEAUTIFUL WATER FRONT WHITE MARLIN BEACH HOME. THIS NEWLY UPDATED CBS CONSTRUCTION HOUSE HAS A PRIVATE BAY FRONT WHITE MARLIN BEACH HOME OWVER PARK DOWN THE STREET. HIGH END APPLIANCES WITH VAULTED CEILINGS, IMPACT DOORS/WINDOWS AND METAL ROOF. THE HOME FEATURES A BEAUTIFUL DOCK THROUGH THE MANGROVES WHICH CAN ACCOMMODATE A 22 FT BOAT WITH DIRECT ACESS TO THE BAY. PLEASE CONTACT LISTING AGENT FOR SHOWINGS.

$1,650,000
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 1,769 SqFt Days Listed: 49
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp

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!

$1,650,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,278 SqFt Days Listed: 111
-2.94% ($50,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp

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 homeowners 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.

$1,550,000
Plantation Key
Port Of Call   - MM: 88.50
2 Bed, 2 Baths, 1,248 SqFt Days Listed: 480
-10.14% ($175,000) 3 Price Changes : Last Change 33 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip

Ocean View Completely Remodeled Townhouse in Beautiful Islamorada!This beautifully updated town home offers 2 bedrooms, 2 bathrooms and a powder room including an ocean view Master Suite, with private porch and roof top deck, an amazing kitchen, with sunroom dining, open living space with ocean views and a screened porch. Located in Private Port of Call allowing weekly rentals with only 10 units featuring an ocean front pool, boat slip, sandy beach, carport, storage, laundry room in the unit with a pantry. This is a great investment opportunity with excellent rental income. Call for an appointment today!

$1,550,000
Upper Matecumbe Key Islamorada
Grove Park   - MM: 81.50
2 Bed, 2 Baths, 1,556 SqFt Days Listed: 35
-3.13% ($50,000) 1 Price Change : Last Change 5 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Welcome to one of downtown Islamoradas most exclusive properties- a spacious estate thats hitting the market for the first time in generations. This ranch-style home sits proudly on four contiguous lots in the peaceful Grove Park Subdivision, offering something thats increasingly scarce in the Keys: space to breathe. With two bedrooms and an oversized garage (50 x 26) thats perfect for an artists studio, boat and car storage plus a Workshop, and Utility buildings. Space to park your RV or Camper. This property gives you room to live and create.Step outside and youll find yourself in a tropical paradise. Fruit trees dot the landscape, and carefully planned gardens create a private sanctuary. Lounge in your Gazebo and an in-ground pool (25 x 40) beckons on those warm Florida afternoons, while the lush landscaping ensures your privacy from the world beyond.Location? It doesnt get better than this. Take a short stroll and youre in the vibrant heart of Islamorada. Wander through Artists Alley, browse local shops, or treat yourself to dinner at some of the Keys finest restaurants - all just minutes from your front door.This property isnt just a home - its a blank canvas of possibilities in paradise. And with properties like this becoming increasingly rare in the Keys, it wont be available for long.

$1,350,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
3 Bed, 3 Baths, 960 SqFt Days Listed: 408
-3.57% ($50,000) 3 Price Changes : Last Change 27 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Beautiful Downtown Islamorada Cottage! This newly constructed home is located on an oversized lot with a pool, outdoor entertaining area, plenty of storage, parking, and handicap access. The home features 3 bedrooms & 3 bathrooms with two of the bedrooms ensuite. The home offers a great floor plan and has been tastefully decorated with a beautiful kitchen including stainless steel appliances. This is a great investment with rental history. Dont miss the opportunity to own where you can walk and ride your bike to all the places downtown Islamorada has to offer including shopping, restaurants, bars, and all the amenities The Sports Fishing Capital of the World has to offer!

$1,350,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
4 Bed, 4 Baths, 1,459 SqFt Days Listed: 6
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Your Slice of Paradise Awaits in Downtown IslamoradaDiscover the perfect blend of modern coastal living and convenience with this beautifully remodeled ground-level duplex in the heart of Islamorada. Located just a moment from the famous Cheeca Lodge and the vibrant Arts District, youll be surrounded by charming shops, restaurants, and galleries.Property Highlights: Two Separate Units PLUS a Guest Space: Each of the two dwellings is thoughtfully designed with a bright, airy ambiance to complement the island lifestyle. Use one unit for yourself and rent out the other, and/or welcome family and friends to visit! Durable Construction: Built with concrete and topped with a sturdy metal roof, this home is designed to withstand the elements. Impact windows and doors provide added protection and energy efficiency. Private Outdoor Oasis: The fully fenced yard features an electric gate, artificial turf for low maintenance, and lush landscaping with vibrant tropical foliage, perfect for relaxing or entertaining.Why Youll Love It:Whether youre looking for a permanent home or a vacation retreat, this property delivers the ideal Florida Keys lifestyle. The Village of Islamorada recognizes two dwelling units, adding significant value to the property.Dont miss your chance to own this coastal gem in an unbeatable location! Buyers should be able to convert this building in to one single-family home and transfer one of the building rights to another Village non-waterfront lot that is deemed appropriate by the Village. Two units are recognized by the Village. Buyers must confirm all with Village of Islamorada.

$1,350,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,550 SqFt Days Listed: 168
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This newly remodeled 3 bedroom, 3 bathroom home is located on upper Matecumbe in the heart of Islamorada, Florida. The home features a unique layout with 1 bedroom and 1 bathroom downstairs, and 2 bedrooms and 2 bathrooms upstairs. The home boasts high-quality construction and modern finishes throughout. The open-concept living area is perfect for entertaining, with a spacious kitchen featuring stainless steel appliances and granite countertops. The bedrooms are all generously sized and offer plenty of natural light. Outside, the home features a large deck perfect for enjoying the beautiful Florida weather. The property is within proximity to world-class restaurants and is accessible to some of the best fishing and diving spots in the world. This home is the perfect blend of luxury and convenience, making it an ideal choice for those looking to experience the best that Islamorada has to offer.

$1,325,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 2,808 SqFt Days Listed: 50
-1.85% ($25,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Paradise Found: Renovated Jungle Treehouse!Welcome to your dream retreat in the heart of the Florida Keys. Nestled in the highly sought-after village of Islamorada, this exquisitely remodeled 3-bedroom, 3-bath estate redefines luxury living- 2/2 up and legal nonconforming 1/1 down. Perfectly situated on a sprawling 15k+ square-foot lot (14k sf residential dry and 1k sf easement) , this property offers an unparalleled combination of elegance, privacy, and tropical charm. Concrete roof fully resurfaced in 2024, and electrical, and state-of-the-art impact windows, providing peace of mind and protection while letting in abundant natural light. The interiors have been meticulously updated whilst keeping the Old Florida Charm alive. The kitchen is a true chefs dream.

$1,325,000
Plantation Key
Toners Nautical Sh   - MM: 87.00
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 54
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Escape to paradise in this stunning Islamorada retreat! This beautiful professionally remodeled, low maintenance, 2-bedroom, 2-bathroom concrete home offers the perfect blend of modern luxury and tropical tranquility. Featuring an updated metal roof, new impact windows and doors, all new plumbing and electric with a brand-new A/C unit, this home is ready to enjoy the island lifestyle starting on day one. Step outside to enjoy a stunning resort style 34x17 heated pool with a large deck area, complete with a two-story tiki hut featuring a freshly thatched roof -- ideal for entertaining. This property lives like a large home with an abundance of living and storage space. Relax in the expansive 360 sq ft screened-in patio with living and dining areas or explore the various serene spots throughout the lush tropically landscaped 15,870 sq ft double lot property, all enhanced with extensive native foliage and lighting to create an enchanting atmosphere. A short 150 walk brings you to a user-friendly neighborhood boat ramp, offering immediate access to world-class sportfishing in the Atlantic Ocean, excellent backcountry fishing in the Gulf, or a leisurely boat ride to nearby waterfront restaurants. Dont miss the chance to own this exceptional property in one of the most sought-after locations in the Florida Keys!

$1,300,000
Upper Matecumbe Key Islamorada
Green Turtle Beach   - MM: 81.00
2 Bed, 2 Baths, 772 SqFt Days Listed: 167
-3.70% ($50,000) 1 Price Change : Last Change 109 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

This stunning property offers a rare opportunity with two lots and over 24,000 square feet of space, situated in the heart of Islamorada. This property is one of the sixteen durable Red Cross homes constructed in Islamorada. Built with solid poured concrete, these homes are designed to withstand hurricanes. features ample room for EXPANSION, allowing you to customize the space to suit your needs and desires.This 2-bedroom, 1-bathroom home has been completely renovated in 2023 with modern upgrades. The bathroom features custom cabinetry and a walk-in shower with a glass enclosure. The updated kitchen includes stainless steel appliances--a propane range, microwave, dishwasher, and refrigerator--along with custom cabinets. Plus, the entire property is fully fenced, offering both privacy and security.The expansive outdoor space offers endless possibilities--whether you envision adding a pool, tennis court, or a beautiful garden, the choice is yours.Dont miss the chance to own a home where you can easily walk or bike to all the attractions downtown Islamorada has to offer, including shopping, restaurants, bars, farmers markets, and everything that makes The Sports Fishing Capital of the World so special!

$1,299,999
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,314 SqFt Days Listed: 101
-13.33% ($200,000) 2 Price Changes : Last Change 75 Days Ago
Single Family - Contingent - Waterfront No
Side of Island: Ocean - Dockage: Other Dockage

PRICE REDUCTION: Anglers Reef. *7 DAY RENTAL LICENSE* Looking for a second home that pays for itself? Or an investment property w/ an even higher return? This beautiful home situated in Islamorada, better known as Village of the Islands, is already generating income w/ short term rentals to offset your carrying costs. Live the world famous tropical lifestyle & fish for dinner half of the year, cover your mortgage by charging others to enjoy the same experience the other half! Remodeled 2/3 home with 4 porches, 2 carports, ocean views and a community pool. Upgrades include impact windows & doors, a metal roof, new plank vinyl floors, kitchen includes stainless steel appliances, wood cabinets and granite counter tops. Anglers Reef is Islamoradas Upscale Oceanfront Gated Community with 52 homes. Amenities include gated entryway, a marina, community pool on the Ocean, 2 sandy beaches & quaint streets to take walks. Call today for a showing.

$1,200,100
Windley Key
Pelican Cove Resort   - MM: 85.50
3 Bed, 3 Baths, 1,680 SqFt Days Listed: 123
-14.28% ($199,900) 2 Price Changes : Last Change 32 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Ocean - Dockage: First Come Dock

Peaceful Palms is a newly-constructed coastal development and spruced weekly vacation rental located in the gated community of Islamorada, Florida. This high-end property includes 15 townhomes, all positioned to offer oceanfront locations and views. Residents can enjoy stunning sights of the Sandbar and Alligator Reef Lighthouse, along with beautiful sunrises. For those interested in boating, there are oceanfront docking facilities available. The development also features an oceanfront pool, making it an ideal spot for a Florida Keys vacation or investment. Each townhome includes three bedrooms, three bathrooms, a spacious garage, and balconies on the second and third floors with oceanfront views. The property is pet-friendly and located near excellent fishing and diving spots. With the possibility of new building permits being limited in the Florida Keys, investing in Peaceful Palms could be a timely opportunity. Currently, the townhomes are available at pre-construction prices.

$1,199,999
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,376 SqFt Days Listed: 8
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Other Dockage

Anglers Reef, Islamoradas Upscale Oceanfront Gated Community, 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 doors & windows. The community features 2 sandy beaches, a pool & marina on the Atlantic Ocean. Home has been in rental program for many years with a good following. Own your vacation home for free & more. Great investment. Call today for a showing!

$1,195,000
Plantation Key
Plantation Ridge   - MM: 87.00
3 Bed, 3 Baths, 1,152 SqFt Days Listed: 92
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Boat Ramp

Discover your dream getaway in this charming island retreat, perfectly situated on one of Islamoradas most coveted streets. Surrounded by tropical lush vegetation, this all-concrete property offers the ideal blend of privacy and access to paradise, just steps away from Founders Park, featuring a beach, tennis and pickleball courts, and an Olympic-sized pool.This two-bedroom, one-bathroom home boasts multiple outdoor decks, including a spacious rooftop deck with breathtaking ocean views and refreshing breezes. Relax in the gorgeous pool or enjoy the abundant shaded yard space, perfect for family gatherings or tranquil afternoons among the vibrant flora.For added convenience, a separate one-bedroom, one-bathroom bonus studio downstairs provides extra space for guests, along with a garage for your vehicles and storage needs. Launch your boat from the ramp just 200 feet from your doorstep, making it easy to explore the beautiful waters of the Florida Keys.

$1,149,000
Plantation Key
Bay Ridge   - MM: 87.50
3 Bed, 3 Baths, 1,682 SqFt Days Listed: 142
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Othe

Welcome to your charming ground-level concrete home nestled in the highly sought-after Bay Ridge subdivision in Islamorada! This property, situated on a corner lot, boasts a prime location within the coveted X flood zone. Step into this spacious abode offering 3 bedrooms, 2 bathrooms, and bonus room with a built-in bar, ideal for accommodating family gatherings and entertaining guests. The layout provides ample flexibility to tailor the space to your unique lifestyle preferences. Outside, you will enjoy the spacious corner lot offering mature landscaping and lush green lawn along with a brick-paved circular driveway. Immerse yourself in the incredible community amenities, including a beautiful marina, inviting pool, and convenient boat ramp, perfect for enjoying the lifestyle at your leisure. For outdoor enthusiasts, nearby Founders Park offers a sandy beach, olympic-size pool, boat ramp, ball fields, tennis/pickleball courts, and a dedicated dog park. Whether you choose to enjoy the property in its current state or embark on a journey of customization to fulfill your vision, the options are boundless.

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 01-28-2025.
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