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Browse All Islamorada FL Between $300K - $400K Properties for Sale

84961 Old Hwy Unit 28, Islamorada
$375,000
1 Beds ⋅ 1 Baths ⋅ 621872 MLS
ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this charming 1-bedroom, 1-bath trailer offers the perfect opportunity to enjoy the laid-back Florida Keys lifestyle. Ideally situated in the heart of Islamorada, this property offers a relaxed island atmosphere with the convenience of being just minutes from renowned waterfront restaurants, local breweries, boutique shopping, and the many attractions that make Islamorada so desirable. Step outside and enjoy the island breeze, or take advantage of the community's wonderful oceanfront amenities, including a chickee hut, oceanfront jetty, and dock privileges. Relax under the chickee hut while taking in beautiful sunrises and breathtaking sunsets over the water. Low monthly HOA fees of just $149 include common area and road maintenance. Don't miss this opportunity to own your own slice of paradise in the Sport Fishing Capital of the World and experience everything that makes the Florida Keys so special! YOU OWN THE LAND.

84961 Old Hwy Unit 28, Islamorada
87455 Old Hwy Unit APT 234, Islamorada
$399,000
2 Beds ⋅ 2 Baths ⋅ 621854 MLS
Enjoy a tropical retreat at Plantation By The Sea, an oceanfront community in Islamorada. Relax beside the sparkling oceanfront pool or cast a line from the community fishing pier, then head out for waterfront dining, live music, and eclectic local shops. This inviting 2-bedroom, 1.5-bath condo offers a two-level layout with living spaces downstairs and both bedrooms upstairs. Bamboo flooring adds warmth to the living and dining areas and bedrooms. The updated kitchen features white cabinetry and generous counter and storage space. The open living and dining area flows onto a covered balcony nestled among tropical greenery - a pleasant spot for morning coffee or unwinding after a day exploring the island. Both upstairs bedrooms feature sliding glass doors opening to balcony spaces. An updated full bathroom with a tiled walk-in shower, a convenient downstairs half bath, and an in-unit Bosch washer and dryer add everyday comfort. Assigned covered parking and a ground-level storage room provide added convenience. Community amenities also include an oceanfront clubhouse with a kitchen, a pool table, and a ping-pong table - a great place to entertain friends and family. Take in ocean views while working out in the fitness center, or unwind in the men's and women's saunas. Gated entry and kayak and paddleboard storage add to the community's appeal. Nearby Founders Park offers a beach, Olympic-size swimming pool, tennis and pickleball courts, ball fields, and an amphitheater. Whether you're seeking a seasonal getaway or a year-round home, this welcoming condo puts the best of Islamorada within reach.

87455 Old Hwy Unit APT 234, Islamorada
79901 Overseas Highway Unit 217, Islamorada
$399,000
1 Beds ⋅ 1 Baths ⋅ 621774 MLS
Discover this 1 bedroom / 1 bath condo at The Palms of Islamorada, ideally located in the heart of Islamorada on Upper Matecumbe Key. Offering 827sf of living space, this condo features a spacious open porch, covered parking, and convenient kayak and paddleboard storage. The Palms is a gated oceanfront community situated directly on the Atlantic Ocean, with views of Alligator Lighthouse. Residents enjoy a variety of amenities, including a waterfront swimming pool, jacuzzi, tiki hut for entertaining and grilling, fitness facilities, and a community room. Conveniently located near Mile Marker 80, The Palms is adjacent to Lazy Days Restaurant and just minutes from local favorites such as Papa Joe's and Bud N' Mary's Marina. Nearby marinas offer boat storage options, while numerous restaurants, shops, and recreational activities are just a short distance away. Whether you're looking for a primary residence or a seasonal getaway, this condo offers a wonderful opportunity to enjoy the Florida Keys lifestyle in a central Islamorada location.

79901 Overseas Highway Unit 217, Islamorada
High Point Rd, Islamorada
$400,000
621733 MLS
Opportunity awaits to bring your vision to life! This 14,300-square-foot parcel encompasses approximately one-third of an acre, with 130 feet of frontage and 110 feet of depth. Situated on the bayside of Plantation Key in the established High Point neighborhood, this oversized Florida Keys vacant land opportunity offers the space to envision your own island retreat. Partially cleared and fenced, the property is conveniently located near schools, restaurants, shopping, boating, fishing, and all that Islamorada has to offer. Preliminary communications with the Village of Islamorada Building and Planning Departments indicate that the parcel is buildable; however, no formal building approval or permits are currently in place. No protected species restrictions or conservation easements are currently known. Buyers are to independently verify all.

High Point Rd, Islamorada
40 High Point Rd Unit 703, Islamorada
$374,000
2 Beds ⋅ 2 Baths ⋅ 620635 MLS
Turn key furnished condo in Islamorada! This beautifully appointed 2 bedroom, 2 bath condo features an open floor plan, abundant natural light and a rare balcony. Remodeled unit which includes impact windows and doors, crown molding, wood engineered laminate flooring, and a full size washer and dryer. The open-chef's kitchen boasts a spacious breakfast bar, extra tall hardwood cabinets, granite counter tops and backsplash, under-cabinet and recessed lighting, a dishwasher, and a newer refrigerator in 2022. The primary ensuite offers a walk-in closet with custom shelving. AC was replaced in 2023, Metal roof installed in 2024. The complex offers a heated swimming pool, and clubhouse. Founder's Park, Islamorada's Community Park, is on the same island. Admission into the park is free for Islamorada residents. The park offers an Olympic size swimming pool, tennis courts, pickleball courts, ball fields, marina, beach and boat ramp. Plantation Villas is close to Plantation Key Elementary School and Coral Shores High School, grocery store, shopping, restaurants and movie theater.

40 High Point Rd Unit 703, Islamorada
200 Wrenn St Unit APT 502, Islamorada
$399,000
1 Beds ⋅ 1 Baths ⋅ 619403 MLS
Beautiful 1 bedroom, 1 bath condo at Seagulls Condominium in Islamorada with stunning ocean views. Fully furnished and ready to move in or rent. Enjoy resort- style living with oceanfront heated pool, clubhouse and game room. Convenient location close to local dining, shops, and all the beauty the Florida Keys have to offer. Perfect for vacation getaways, living or rental investment.

200 Wrenn St Unit APT 502, Islamorada
Waterfront Waterfront Tdr, Islamorada
$400,000
619203 MLS
This is for the sale of 1 (one) Waterfront Transferable Development Right (TDR aka TBR) for use in The Village only. Buyer to pay ALL closing costs associated with the transaction and the transfer fee to The Village. The sale DOES NOT include any real property. Buyer must have an eligible property to which the rights can be transferred.

Waterfront Waterfront Tdr, Islamorada
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