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$2,050,000
3 Beds ⋅ 3 Baths ⋅ 619722 MLS
Impeccably Designed Islamorada Waterfront Retreat! Welcome to your private island oasis! This stunning 3BR/3BA solid concrete waterfront home on Lower Matecumbe Key combines comfort and style with the ultimate Florida Keys lifestyle. Beautifully updated, this turnkey residence is move-in ready for immediate enjoyment. The inviting floor plan features a well-appointed kitchen with quartz countertops and stainless appliances with open living concept, a spacious primary en suite, and a versatile downstairs guest suite with bedroom and living area--perfect for hosting family and friends or creating your own private retreat. Situated on a canal with immediate ocean access, the property includes 75 feet of concrete dockage with boat lift for the boating enthusiast. The resort-style backyard is designed for endless entertaining with a heated pool, expansive sun deck, screened porch, and multiple indoor-outdoor living spaces--your personal vacation paradise. Located just minutes from Islamorada's acclaimed restaurants, local marinas, world-class fishing, and island attractions, this exceptional home offers the perfect balance of waterfront tranquility and vibrant Keys living. Whether you're lounging poolside, departing for a day on the water, or gathering with loved ones, every day feels like a getaway. Low Flood Insurance currently $2075 available to transfer.

137 Cortez Dr, Islamorada
$1,787,500
3 Beds ⋅ 2 Baths ⋅ 614243 MLS
Calling All Anglers and Investors, Best Priced Pool Home with Views of the Ocean and direct oceanfront access in minutes. Fantastic rental history. 75 ft concrete dock with a boat lift. Built in pool, Master 3rd floor suite with unobstructed views of the Ocean. Impact windows and doors, metal roof. The property is fenced with tropical Landscaping. This recently up dated kitchen with Island eat in kitchen counter, all new stainless steel appliances, all new floors throughout. Master extra large 2nd and 3rd bedrooms, with walk in closet. A boater paradise 75ft of concrete dock with 20,000 lb. boat lift, A set of davits and built in pool with pool heater/chiller for the ultimate outdoor experience. Canal depth is estimated to be 10-12 ft. Direct Ocean Access for your boat. Just 5 minutes to the Ocean and Bay access too. Income producing property with future bookings. The property includes a great yard for entertaining with: Fully gated and fenced yard Automatic sprinkler system, Electric Gate Located on a very quiet dead end street

150 Columbus Dr, Islamorada
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 616594 MLS
Seller will consider seller financing. Florida Keys waterfront home, offered fully furnished, no homeowners association, 1,786 SqFt living area (larger than tax roll) fully renovated 3 bedroom, 3 bath waterfront property situated in Lower Matecumbe Key with 7,500 SQ FT lot. New seawall was completed & elevated in 2021. Boaters paradise w/75FT of dockage, under 5 minute ride to open ocean + easy access to bay as well, plenty of space to install a boat lift. There is also a private neighborhood concrete boat ramp that can be used. Canal depth is estimated 10-12 FT. Unique layout offers 2 bedrooms & 2 baths on the second floor with full kitchen & spacious living room area, washer & dryer. First floor offers 1 bedroom & 1 bath, washer & dryer, full kitchen (separate living units). New roof/hurricane impact windows. Easy storage space. Ample parking.

126 Columbus Dr, Islamorada
$390,000
1 Beds ⋅ 1 Baths ⋅ 606501 MLS
Step inside this Islamorada 1bd/1ba condo and see the updated kitchen with Frigidaire appliances and real wood cabinetry. The living room has a real wood Built-in for plenty of storage. The bedroom has a walk-in closet for even more storage. From the front porch you can view the Common Areas featuring Pickleball/Tennis Courts, Dockage for your boat up to 25'(first come first serve), Pool, Shuffleboard and BBQ/Picnic area. There is also Boat/Trailer Storage, Boat Ramp and designated car wash area and Laundry. Don't miss this opportunity to own in highly desirable Lower Matecumbe!

119 Cortez Dr Unit F2, Islamorada
$6,700,000
4 Beds ⋅ 5 Baths ⋅ 616619 MLS
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. Expansive covered verandahs, a 15' x 30' heated seaside pool, and beachside hammocks invite slow, sun-filled days and relaxed gatherings. Across the street, a separate canalfront parcel with a 37.5' concrete dock provides protected deep-water dockage and space for boats, trailers, and water toys — an extraordinary pairing of true beachfront living and convenient boating access. Inside, the home's 3,860 square feet is designed for easy Keys living with generous main-level living areas and bedrooms, plus a spacious upstairs suite with private bath and roof-top deck capturing panoramic ocean vistas. Four bedrooms and five baths accommodate family and guests comfortably, while breezy porches and open gathering spaces make entertaining effortless. Highlights you'll love: 165' of private sandy Atlantic beach with direct ocean entry, 37.5' private concrete dock on canalfront lot for boating convenience, 15' x 30' heated seaside swimming pool with expansive sun decks, over one acre of tropical privacy and mature landscaping, 4 bedrooms | 5 baths | 3,860 sq. ft. with thoughtful single-level layout plus upstairs suite and roof deck. A true Keys treasure, The Last Resort delivers a rare mix of sandy beach, deep-water dockage, and timeless coastal charm. Ann exceptional opportunity to create your own island legacy!

109 Columbus Dr, Islamorada
$615,000
2 Beds ⋅ 2 Baths ⋅ 617914 MLS
Welcome to 112 Cortez Drive, a beautifully updated 2 bedroom, 2 bath townhouse-style condo tucked along a quiet street on Lower Matecumbe Key. This inviting updated residence offers a multi-level design that provides wonderful separation of space & a naturally bright, coastal ambiance throughout. The main living area features an open layout with comfortable gathering spaces, as well as a functional kitchen. Each bedroom is situated on its own floor with a dedicated bathroom nearby, giving both owners & guests a true sense of privacy. Vaulted ceilings & large windows enhance the home's airy atmosphere. Two screened balconies that extend the living space outdoors—ideal spots to relax, dine, or simply enjoy the outdoors. The upper-level balcony offers a private sitting area off the primary bedrooms adding to the property's tranquil setting & where you can enjoy sunrise & ocean breezes. It is rare to have an oversized garage -- offering abundant room for a vehicle, outdoor equipment, small boat, paddleboards, kayaks, bikes, fishing gear, & additional storage. There is also convenient space for laundry appliances & a freezer. Carport is used for additional outdoor seating area & gardens but has plenty of room for an additional car or boat that may need to be under cover. Enjoy an impressive list of amenities: a spacious & heated swimming pool surrounded by mature tropical landscaping, dockage w/abundant electric and water stations, a private boat ramp, boat & trailer storage yard, fish-cleaning stations, pickleball & tennis courts, shuffleboard, tiki with BBQ area, & a clubhouse with pool bathroom & mail room. Quick and easy access within minutes to the Atlantic Ocean & Florida Bay Whether you're searching for a primary home, a seasonal escape, or an income-producing property, 112 Cortez Drive delivers the perfect blend of comfort, convenience, & the relaxed lifestyle that defines the Florida Keys & just a 10 min to world famous downtown Islamorada.

112 Cortez Dr Unit B1, Islamorada
$1,200,000
2 Beds ⋅ 1 Baths ⋅ 609634 MLS
Islamorada waterfront home boasting 112 feet of canal frontage. Situated on 1.5 expansive lots totaling 11,250 square feet, this charming 2-bedroom, 1-bathroom residence features a spacious screened-in porch on the upper level spanning over 800 square feet. The seamless integration of indoor and outdoor living spaces, complemented by lush landscaping, creates a tranquil retreat reminiscent of being nestled among the treetops. Recent interior paint updates, along with an upgraded kitchen and partially renovated bathroom, enhance the home's appeal. The main bedroom features a spacious walk-in closet and convenient en-suite access to the bathroom. Meanwhile, the guest bedroom boasts pocket sliding doors that seamlessly connect to the covered screened porch. The lower level includes a 2-car garage with electric doors, offering ample space for boat storage and all your recreational gear. With room for a pool on the property, the outdoor amenities extend to a large covered deck and an outdoor shower. There are two docks, a fish cleaning station, and access to a subdivision boat ramp. The canal system provides easy entry to the Atlantic Ocean and quick access to the bayside.

110 Columbus Dr, Islamorada
$1,350,000
3 Beds ⋅ 3 Baths ⋅ 616133 MLS
Incoming producing property with future bookings already in place! Beautiful Florida Keys home, 1,827 SqFt living area (larger than tax roll) fully renovated 3 bedroom, 3 bath waterfront property situated in Lower Matecumbe Key with 7,500 SQ FT lot. New seawall was completed and elevated in 2021. Boaters paradise with 75FT of dockage, under 5 minute ride to open ocean + easy access to bay as well, plenty of space to install a boat lift. There is also a private neighborhood concrete boat ramp to drop a boat in and out. Canal depth is estimated to be 10-12 FT. This unique layout offers 2 bedrooms and 2 baths on the second floor with a full kitchen and spacious living room area, washer and dryer. First floor offers 1 bedroom and 1 bath, washer and dryer, full kitchen and its own washer and dryer for your convenience (separate living units). New roof/hurricane impact windows throughout. Easy storage space. Ample parking.

126 Columbus Dr, Islamorada