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$2,260,000
Lower Matecumbe
Mat Ocean View   - MM: 76.50
2 Bed, 2 Baths, 1,071 SqFt Days Listed: 22
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

Welcome to your slice of paradise in the sought-after Matecumbe Ocean View neighborhood! This beautifully upgraded concrete home (including the roof) is built for durability, comfort, and style. Fully fenced and thoughtfully designed, the exterior grounds features sleek new concrete and turf along the sides of the house for a clean, modern look.The backyard is an entertainers dream with a full outdoor kitchen, a sparkling pool, and a spacious 75 ft. concrete seawall complete with a 15,000 lb elevator boat lift. Enjoy quick and easy access to the ocean via a marked channel--perfect for boating enthusiasts who want to be on the water in just minutes. Great fishing and diving awaits! Inside, youll find an upgraded interior featuring stainless steel appliances, a wine fridge, a walk-in pantry, and generous living space. The large bedrooms offer comfort and privacy, while the expansive balcony invites you to relax and soak in the coastal breezes. Matecumbe Ocean View is a desirable community with its own boat ramp conveniently located at the beginning of the street, making launching a breeze. This home is close to great amenities located in Islamorada like Robbies, Worldwide Sportsman, a number of restaurants, Bud N Marys Marina and more! Whether youre looking for a full-time residence or a vacation escape, Cortez Dr is the ideal blend of luxury, function, and Keys lifestyle.

$2,200,000
Plantation Key
Kahiki Harbor   - MM: 91.00
4 Bed, 4 Baths, 1,708 SqFt Days Listed: 71
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Other Dockage

Now Available! One-of-a-kind Opportunity in the desirable Kahiki Harbor neighborhood. 165 waterfront Corner Lot. Vintage 4 bedroom / 3 bath Custom built Keys home. 2/2 upstairs and a Great Room with all doors opening to the walk-around porch. Downstairs has 700 of additional enclosed storage, laundry, bathroom and two bedrooms. The home sits in the peaceful Kahiki Harbor neighborhood with deep water dockage all the way around the property. Davits and a concrete dock at one end, with additional dockage areas, a Gazebo and a Sailboat Launch Ramp following the corner of the 8,760 oversized lot. The large yard offers potential for a pool and outside entertaining areas. Endless possibilities await!- Build your Dream Home on this Unique and One-of-a-Kind Property, just off Tavernier Creek and minutes from the Ocean or Bay.

$2,100,000
Lower Matecumbe
Matecumbe Ocean Bay   - MM: 75.00
2 Bed, 2 Baths, 1,322 SqFt Days Listed: 215
-14.29% ($350,000) 1 Price Change : Last Change 82 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

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. Dont miss your chance to make this idyllic getaway your own!

$2,049,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,295 SqFt Days Listed: 293
-1.91% ($40,000) 1 Price Change : Last Change 44 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift,Dav

**Waterfront Paradise: Solid Concrete Home on Deep Water Canal**Nestled along a serene deep water canal, this exquisite solid concrete home awaits its new owner. Embark on a brick paver driveway that leads to a turn-key residence designed to impress.As a boaters paradise, this property boasts a private boat lift, davit, clean out station, and outdoor shower. Access to the communitys boat ramp allows for effortless excursions.Step inside and be captivated by the beautifully furnished interior with breathtaking canal views. The open floor plan seamlessly blends the gourmet kitchen, dining area, and living room, offering an inviting space for entertaining and relaxation. Top-of-the-line appliances and entertainment areas elevate the living experience.The spacious master bedroom and bathroom provide a luxurious oasis with access to a large screened balcony. The master bathroom features a soaking tub, separate shower, and double vanity.The downstairs level offers an enclosed garage with two bay doors and ample storage. A custom-made bar, full bathroom, and additional storage space create a versatile flex room perfect for various uses.The propertys tranquil exterior features lush landscaping, gardens, and a charming front porch. The rear stairs provide convenient access to the waterfront.With a straight shot to the bay and just around the corner from the ocean via Tavernier Creek, this home offers unparalleled access to the water. The neighborhood community offers a boat ramp for members.This dream home is a rare find. Dont miss this opportunity to own a piece of paradise. Call today to schedule a private showing and experience the beauty of this solid concrete waterfront residence. Call Today!

$1,999,999
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,674 SqFt Days Listed: 221
-6.98% ($150,001) 1 Price Change : Last Change 35 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip31ft.

ANGLERS REEF OCEANFRONT HOME WITH DEEDED DOCK. 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

$1,859,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,804 SqFt Days Listed: 163
-1.90% ($36,000) 1 Price Change : Last Change 25 Days Ago
Single Family - Contingent - 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!

$1,795,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
4 Bed, 4 Baths, 1,629 SqFt Days Listed: 190
-7.95% ($155,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits70ft.Concrete

Discover unparalleled Keys living at 190 Gulfview Dr in Islamoradas exclusive White Marlin Beach. This exquisite 4-bedroom, 3-bath home boasts 70 feet of private dockage with seamless access to both ocean and bay waters. Enjoy a sparkling pool with covered entertainment space, an expansive upstairs balcony, and abundant storage for your gear. The additional downstairs living area offers extra flexibility, perfect for guests. With private access to White Marlin Beach, youll be steps from pristine sands and breathtaking sunsets. This property offers exceptional rental history with repeat guests and strong cash flow which make this an outstanding investment. Embrace luxury island living at its finest!

$1,740,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 1,568 SqFt Days Listed: 96
-10.77% ($210,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 70ft.

Venetian Shores location for under $2M! This spacious and solid concrete house has an excellent location right off Snake Creek for fast access to both Ocean & Bay, fuel, bait and provisions. Enjoy 70 of commercially zoned dockage in the best Islamorada location available! Upstairs features an open floor plan with gourmet kitchen and breakfast bar, office area, bonus room, roomy bedrooms and two full bathrooms. Downstairs guest suite with bathroom & kitchen plus screened patio to access the outside tiki hut and nice outdoor living on the canal.

$1,660,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
3 Bed, 3 Baths, 1,380 SqFt Days Listed: 109
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 OWNER 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.

$1,600,000
Upper Matecumbe Key Islamorada
Green Turtle Beach   - MM: 81.00
3 Bed, 3 Baths, 2,128 SqFt Days Listed: 19
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Welcome to Turtles Nest, a charming home offering the perfect blend of comfort, flexibility, and Florida Keys lifestyle, all set on an oversized, lushly landscaped corner lot in the heart of Islamorada. A 3 Beds - 2 Baths + Office & Two-Car Garage - 2,128 Sq. Ft. under Air conditioning on an oversized, 12,300 Sq. Ft. lot. This beautifully maintained home with a private office/flex space features a spacious, sun-filled layout with impact-resistant windows. The enclosed wraparound sunroom is ideal for year-round enjoyment. Enjoy the convenience of two full laundry rooms, a rare bonus for seasonal or full-time residents. The private office with its own exterior entrance offers the perfect setup for remote work or guests. The home also boasts a fully air-conditioned and heated 2-car garage, perfect as a workshop, gym, or storage space. Step outside to find an outdoor shower with hot water, an electric gated entry, and dedicated boat trailer parking. The tropical landscaping with mature greenery and fruit trees surrounds the home, providing privacy and a true island retreat vibe. Located in an exclusive neighborhood with deeded access to the renowned and historic Green Turtle Beach, private oceanfront park, perfect for enjoying sunrises, walks, kayaking, or beach picnics for just $33 a month. Just minutes from world-class restaurants, galleries, spas, pickleball courts, and more. This home offers a peaceful island living with a walkable, vibrant lifestyle. Furnishings available and negotiable.

$1,599,900
Plantation Key
Indian Waterways   - MM: 89.00
3 Bed, 3 Baths, 1,769 SqFt Days Listed: 38
-1.54% ($25,100) 1 Price Change : Last Change 3 Days Ago
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!

$1,450,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
2 Bed, 2 Baths, 960 SqFt Days Listed: 74
-3.01% ($45,000) 2 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift75ft

Welcome to Two White Turtles, a beautifully renovated, turnkey waterfront coastal paradise retreat - perfect for a vacation rental, second home, or primary residence. This stunning canal-front property offers homeowner access to a rare white sandy BEACH and is designed for the ultimate Florida Keys lifestyle. The grand French door entrance leads to open-concept areawhich features soaring wood-beamed ceilings, abundant natural light, a gourmet chefs kitchen with quartz countertops, French door refrigerator, all stainless appliances, a pantry with pullout drawers, ample storage, a dining spot and living space for entertaining or lounging while watching a 55 TV. Off the lounge are two ensuite bedrooms, each with their ownbathroom, wall mounted TV, abundant closet space, and dual sinks with a walk-in shower in the primary suite. Outdoors, relax in the tiki hut by the canal, rinse off in the outdoor shower, or unwind in the private backyard overlooking the mangroves. The 75 dock with a 7k boat lift and davits makes this a boaters paradise, offering direct ocean and quick bay access via Channel 2 and 5 bridges - just minutes from Alligator Reef Lighthouse. Additional features include a one-car garage with extra storage, ample parking for trailers, multiple vehicles, and an RV. Featuring a fenced, no-maintenance turf grass yard with pavers, a newer 5V crimp roof, with impact windows and doors. Peekaboo ocean views, starry nights, and ocean breezes enhance the homes serene setting. A bonus generator, extra fridge and freezer also add convenience. An easy walk to some nearby restaurants is a plus, making this location a perfect slice of paradise. Come watch the manatees float by and experience Keys living at its finest. Schedule your private showing today!

$1,400,000
Upper Matecumbe Key Islamorada
Oceana   - MM: 82.00
3 Bed, 3 Baths, 897 SqFt Days Listed: 36
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Located in downtown Islamorada, this property offers an ideal lifestyle with a great floor plan for work-life balance. The separate office guest quarters overlooking the pool creates a perfect work environment. This home offers 3 bedrooms & 3 bathrooms, and a split floor plan, ideal for a family that is looking for privacy and space. Enjoy the large private inground pool, & outdoor entertainment area along with access to a sandy beach with dock, boat launch, and stunning ocean views, all within walking distance to restaurants, shops, and art galleries.

$1,300,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
3 Bed, 3 Baths, 960 SqFt Days Listed: 8
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!

$1,300,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,240 SqFt Days Listed: 72
-7.14% ($100,000) 1 Price Change : Last Change 30 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Looking for a home to accommodate you and your guests? This concrete construction property features three bedrooms and two baths on the upper level. Lower level offers two bedrooms and one bath, plus a waterfront screen porch, open floor plan, legally permitted enclosure with a living area that includes a kitchenette, plus living room. Plenty of storage with attached workshop/garage. Located on a plugged canal in Venetian Shores, there is a marina available for lease dockage monthly depending on availability.

$1,275,000
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,620 SqFt Days Listed: 46
-3.77% ($50,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your perfect getaway in the heart of the Florida Keys! This beautifully updated 2-bedroom, 2.5 bathroom townhouse is located in Islamorarda in a resort-style community with fantastic amenities. Whether youre looking for a vacation home, an investment property, or both, this tropical retreat offers everything you need.Enjoy an open-concept living space with abundant natural light, a fully equipped kitchen, and spacious bedrooms with en-suite bathrooms. Step outside to your private balcony or patio and soak in the island breeze. This townhome is the only property in association that is situated on two lotsThe community features a sparkling pool, a marina with boat dockage. With weekly rentals allowed, this property is a fantastic income opportunity in a high-demand tourist destination.Located just minutes from world-class fishing, boating, snorkeling, and dining, this townhouse offers the ultimate Florida Keys lifestyle. Dont miss out on this rare opportunity--schedule your private tour today!

$1,199,999
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,376 SqFt Days Listed: 109
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Other Dockage

ANGLERS REEF HOMEf, 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!

$1,199,000
Plantation Key
Toners Nautical Sh   - MM: 87.00
2 Bed, 2 Baths, 1,200 SqFt Days Listed: 155
-9.51% ($126,000) 3 Price Changes : Last Change 2 Days Ago
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!

$1,195,000
Plantation Key
Plantation Ridge   - MM: 87.00
3 Bed, 3 Baths, 1,152 SqFt Days Listed: 193
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.

$1,100,000
Plantation Key
Bay Ridge   - MM: 87.50
3 Bed, 3 Baths, 1,682 SqFt Days Listed: 243
-4.26% ($49,000) 1 Price Change : Last Change 52 Days Ago
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 05-09-2025.
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