Lower Matecumbe Homes with Canal Front Waterfront features

Lower Matecumbe Homes with Canal Front Waterfront features

Welcome to Lower Matecumbe, a hidden gem nestled in the heart of the Florida Keys! Located within the charming city of Islamorada in Monroe County, this enchanting island offers a unique blend of natural beauty, vibrant marine life, and a laid-back lifestyle that many dream of. Lower Matecumbe is renowned for its stunning sunsets, crystal-clear waters, and an array of outdoor activities that make it a paradise for nature lovers and water enthusiasts alike.

One of the most appealing aspects of Lower Matecumbe is its exquisite canal-front waterfront homes. Imagine waking up to the gentle sound of waves lapping at your dock, with your private slice of paradise just steps away. These homes boast direct access to the sparkling waters of the Atlantic Ocean, making them perfect for boating, fishing, and paddleboarding. Many properties feature spacious outdoor living areas, lush tropical landscaping, and breathtaking views that capture the essence of island living.

Whether you’re looking for a cozy retreat or a luxurious waterfront estate, Lower Matecumbe has something for everyone. The local community is warm and welcoming, with a variety of shops, restaurants, and recreational activities that cater to all ages. With its rich history, diverse wildlife, and stunning natural surroundings, Lower Matecumbe is not just a place to live—it's a lifestyle.

If you’re ready to embrace the island way of life and explore the enchanting homes with canal front waterfront features, Lower Matecumbe awaits you with open arms. Your dream home in paradise is just a heartbeat away!

Newest Lower Matecumbe Homes with Canal Front Waterfront features

$999,999
3 Beds ⋅ 3 Baths ⋅ 621101 MLS
This waterfront home offers 36 feet of dockage and a beautifully renovated interior designed for effortless Keys living. Thoughtfully updated and tastefully decorated, the home is move-in ready and ideal for full time living or weekend getaway. The layout is exceptionally well-suited for hosting and entertaining, with two bedrooms and two bathrooms on the main living level, and a large separate guest suite and bonus area on the lower level providing privacy and flexibility. Enjoy peaceful views from the screened-in porch, perfectly positioned to capture a straight, open view down the canal, while the spacious backyard offers plenty of room to relax, entertain, and a blank canvas to further enhance your outdoor living experience to your liking. Boaters will appreciate quick access to the ocean, with a beautiful sandbar/beach nearby, perfect for anchoring up for a day of sun, as well as convenient routes to the bay via Channel 2 or Channel 5 bridges. Additional features include a rare garage space, ideal for storing a golf cart, jet skis, and gear while keeping everything protected from the elements.Located on Lower Matecumbe Key, this property provides a walkable Keys lifestyle. Stroll down to the fishing pier to catch dinner and take in a sunset view or hop in the golf cart and ride down to the locals favorite, Habanos restaurant and their new tapas bar right on the ocean for dining and drinks. This is a must-see waterfront opportunity combining comfort, functionality, and the best of island living.

100 Iroquois Dr Unit Unit 5, Islamorada
$2,890,000
3 Beds ⋅ 3 Baths ⋅ 620743 MLS
Welcome to your coastal retreat in the highly sought-after Port Antigua neighborhood--where relaxed Keys living meets exceptional boating access and resort-style amenities. Residents enjoy a private homeowner's beach and boat ramp, enhancing the ease of life on the water. This solid CBS construction home offers approximately 75 feet of dockage, a 12,000 lb boat lift, and a convenient fish cleaning station--perfect for avid boaters and anglers alike. After a day on the water, unwind by the beautifully designed pool where a spa cascades into the water, complete with a swim jet, heater, and chiller for year-round enjoyment. Upstairs, the open floor plan is bright and inviting, anchored by a well-appointed kitchen featuring stainless steel appliances, quartz countertops, and a generous island ideal for gathering. Two spacious bedrooms and baths provide comfort and privacy, while a versatile Florida room serves perfectly as a home office and gym. Built for durability and peace of mind, the home includes a concrete roof, impact windows and doors, and an Arlo security system. A rooftop deck offers additional space to relax and take in the coastal surroundings. Downstairs, an expansive covered entertaining area flows seamlessly to the pool and tiki hut--thoughtfully equipped with lighting, ceiling fan, grill, side burner, sink, and refrigerator--creating the ultimate setting for outdoor living. Elevated above flood, the guest quarters feature a private living area, bedroom, and bath with access from both the pool and interior, making it ideal for visitors. A perfect blend of comfort, function, and island charm--this is Port Antigua living at its finest.

101 Madeira Ct, Islamorada
$11,700,000
6 Beds ⋅ 8 Baths ⋅ 620680 MLS
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. Completed in 2025, the three-level main residence features two primary suites, three guest bedroom suites, media room, an elevator, and a custom kitchen showcasing mahogany cabinetry and Thermador appliances. Expansive balconies extend the living spaces into the natural surroundings. The third-level Sunset Lounge elevates entertaining with a full bar, wine storage, generous seating, a mega-TV, and views toward Florida Bay. Outdoors, the property features a saltwater pool and spa, covered dining and entertaining areas, a private pickleball court, and a dock with boat lift. A detached guest house provides comfortable accommodations with added separation from the main residence. This distinctive Islamorada estate brings together natural beauty, recreation, boating access, and elevated island living.

77350 Overseas Hwy, Islamorada
$3,100,000
5 Beds ⋅ 3 Baths ⋅ 620602 MLS
Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathrooms with an open living floor plan. The main living level features three bedrooms and two bathrooms, complemented by a spacious living, dining, and kitchen area--ideal for entertaining and relaxed Keys living. The lower level includes two additional bedrooms and one bathroom, all above flood, perfect guest quarters with a full kitchen. Brand new exterior paint! Enjoy 75 feet of deep-water concrete dockage equipped with a 15,000 lb boat lift, providing excellent boating access. The home is solid concrete construction with a metal roof, fenced yard, and plenty of room for a pool. Port Antigua is known for its exceptional amenities, including one of the best private beaches in the Keys and a community boat ramp. With immediate access to Florida Bay and quick proximity to the Atlantic Ocean, this property offers the ultimate Florida Keys lifestyle--boating, water access, and island living at its finest.

117 El Capitan Dr, Islamorada
$3,900,000
620460 MLS
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. Encompassing over 32,000 square feet, this extraordinary property provides the perfect canvas for a custom waterfront residence designed to capture spectacular sunrises, refreshing ocean breezes, and the unmatched beauty of the Florida Keys. Its unique setting offers the best of both worlds--open water vistas in the front and a wide canal in the rear, creating an unparalleled lifestyle for boating enthusiasts and those seeking privacy, space, and unforgettable scenery. Opportunities to acquire a property of this caliber have become increasingly scarce in Islamorada, where large vacant parcels are exceptionally limited. Whether you're envisioning a private family compound or a legacy waterfront estate, this one-of-a-kind offering represents a chance to create something truly extraordinary in one of the Florida Keys' most desirable destinations.

74900 Overseas Hwy, Islamorada
$1,890,000
5 Beds ⋅ 3 Baths ⋅ 620271 MLS
Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly sought-after Lower Matecumbe. This exceptional 5-bedroom, 3-bath residence combines contemporary design with breathtaking water views, creating a truly unique island retreat. The thoughtfully designed layout features three spacious bedrooms on the lower level and two additional bedrooms upstairs, connected by a spectacular modern staircase that serves as a striking architectural centerpiece. Soaring ceilings and expansive windows fill the home with natural light, while the open-concept floor plan seamlessly connects the living, dining, and entertaining spaces. The sleek, modern kitchen is perfectly positioned to serve both everyday living and waterfront gatherings. Generously sized bedrooms and beautifully appointed bathrooms provide comfort and privacy for family and guests alike. Step outside to an impressive 667-square-foot waterfront screened deck overlooking the tranquil lagoon, offering the perfect setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Boaters will appreciate the deep-water dockage featuring a large boat slip and 16k boat lift, with convenient access to both the Atlantic Ocean and Florida Bay. Enjoy stunning views of the bayside lagoon and the ocean, along with world-class fishing, diving, and boating right from your backyard. Additional amenities include covered parking and ample storage space for all your water toys. Offering the perfect blend of modern elegance, waterfront living, and premier boating access, this remarkable Lower Matecumbe property is a rare opportunity to own a piece of paradise in one of Islamorada's most desirable locations. Onsite property management for true peace of mind.

74980 Overseas Highway Unit 3, Islamorada
$6,150,000
6 Beds ⋅ 7 Baths ⋅ 620190 MLS
Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence seamlessly blends architectural elegance with modern comfort. The heart of the home features a chef's kitchen outfitted with top-of-the-line appliances, custom cabinetry, and breath taking stone finishes on the countertops and backsplash. A thoughtfully placed custom steam shower adds a spa-like element to the home's exceptional amenities. This home is perfect for everyday living and elevated entertaining. Expansive living spaces flow effortlessly to the outdoors, where covered lounge areas, low-maintenance artificial turf, and tropical landscaping create the ultimate indoor-outdoor lifestyle. A full laundry room and spacious garage add practicality to the property's thoughtful design. Boating enthusiasts will appreciate 100 feet of prime dockage plus an additional 20 feet of canal frontage, offering unmatched access and flexibility for multiple watercraft. Not included in the listed square footage is a 488 SF garage and over a thousand square feet of covered patio. This home is perfect for the indoor/outdoor entertainer. A true statement of coastal luxury—this is Florida Keys living at its finest.

194 Buttonwood Ln, Islamorada
$4,750,000
4 Beds ⋅ 5 Baths ⋅ 619714 MLS
Double Lot! Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story residence offers 4 bedrooms, 4.5 baths, and an extraordinary 220 feet of dockage with dual boat lifts. Every bedroom is beautifully appointed across thoughtfully designed living levels. Step outside to your private marina, where turnkey boating infrastructure meets the crystalline waters of the Florida Keys. Port Antigua residents enjoy exclusive access to a private beach and boat ramp amenities known only to a select few. Where unmatched dockage and island luxury converge in one of Islamorada's most coveted addresses.

44 W Plaza Del Lago, Islamorada
$995,000
619655 MLS
Potential Short sale!!!Waterfront commercial investment opportunity with 100 feet of dockage on a 13,500 sq ft lot, offering both canal frontage and open ocean views--an increasingly scarce combination in the Upper Keys. Ideally located just outside Port Antigua and White Marlin Beach, the property benefits from strong visibility and proximity to established boating and residential communities. The site features convenient eastbound ingress and egress, supporting efficient operations and customer access. Zoned Commercial Fishing, it allows for a diverse range of income-producing uses, including charter services, boat rentals, marine repair, seafood distribution, restaurant or other waterfront commercial ventures. With direct water access, substantial dockage, and flexible zoning, this parcel is well-positioned for long-term appreciation and immediate revenue potential in a supply-constrained coastal market.

74520 Overseas Hwy, Islamorada
$649,000
2 Beds ⋅ 2 Baths ⋅ 619328 MLS
This island resort style unit offers stations for dockage up to 25-foot boats, 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.

118 Cortez Dr Unit B2, Islamorada
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 618050 MLS
Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach neighborhood of Islamorada. A light-filled open-concept layout seamlessly connects the living, dining, and kitchen areas--perfect for entertaining or relaxed island living. The home features three spacious bedrooms and three full bathrooms, including a luxurious primary suite with a sleek modern en-suite bathroom and a large walk-in closet. A versatile bonus room offers endless possibilities as a media room, den, office, or children's retreat. The oversized gourmet kitchen is a chef's dream, showcasing brand-new high-end stainless steel appliances, elegant quartz countertops, and generous storage. Impact-resistant windows and sliding glass doors provide peace of mind while enhancing the home's clean, contemporary style. Step outside to your private backyard and enjoy peaceful sunrise views or savor coffee and cocktails beneath the shaded gazebo. Boaters will love the newly decked 60-foot dock, offering immediate access to both the Atlantic Ocean and Florida Bay. From watching manatees glide by to cleaning the day's catch at the large fish station, every detail is designed for waterfront living. An added bonus is the voluntary HOA, which provides access to a wide sandy beach, known as a turtle-nesting haven. Welcome to your place in paradise. 🌴

159 Iroquois Dr, Islamorada
$4,750,000
5 Beds ⋅ 5 Baths ⋅ 615676 MLS
Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime waterfront location, this beautiful resort-style residence offers generous living spaces, including both upstairs and downstairs primary suites, three additional guest suites, a dedicated office, shaded porches on both levels and a spacious garage for ultimate flexibility. The gourmet kitchen flows seamlessly to a fully equipped outdoor kitchen and shaded lounge area--ideal for al fresco dining by the pool amid lush tropical landscaping. A rare combination of classic design, modern amenities, and timeless island charm. Effortless boating and space for all of your waterfront toys with 75' of deepwater dockage and quick access to both ocean and bay. Nearby homeowner's park provides the added bonuses of a private, sandy beach and boat ramp. With the serene, wide canal views and cooling bay breezes, and this is where luxury, comfort, and natural beauty, convenience converge.

88 W Plaza Del Lago, Islamorada
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