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$649,000
1 Beds ⋅ 1 Baths ⋅ 620677 MLS
Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islamorada, which is recognized as ''The Sport Fishing Capital of the World''. Islamorada is renowned for fine dining, water sports, The Art District, galleries, shopping and breweries. The resort encompasses 27 acres with 1,200' of beach frontage and a 525' fishing pier. This beautiful one-bedroom King suite, with additional sleeper sofa in the living room and private screened balcony, overlooks the garden and waterfall. This is a luxury, income-producing property. Nightly rentals are allowed, with onsite management, an owner's closet, and owner's use of up to 28 days. The resort offers a 24-hour shuttle, valet parking, concierge service, 5-star fine dining, ballroom, conference room, a spa, fitness center, beach, pools, dock, tiki bars, 9-hole par 3 golf course, Pickle Ball courts, lighted tennis courts, lush gardens, bike path, fishing, diving, snorkeling, water sports and Camp Cheeca for children.

81801 Old Hwy Unit 754, Islamorada
$629,900
2 Beds ⋅ 2 Baths ⋅ 620555 MLS
Welcome to Futura Yacht Club! Your island getaway awaits in this highly desirable Plantation Key community. Unit 304 is a 2 bed, 2 bath, beautifully maintained condo. Florida Bay views make this third floor perch heavenly. A hideaway murphy bed is an additional feature adding to the desirability of this coastal condo as an ideal second home or rental. Owners and renters benefit from extensive community amenities, including a boat ramp, on-site boat and trailer storage, a large pool with adjacent club area, kayak storage, paddleball and basketball courts, and well-maintained grounds with shaded picnic spots. The on-site management team maintains the serenity of this community. This immaculate condo is being sold fully furnished. Futura is the place to be for boating, with short run times to the Ocean and Florida Bay. Easy boating and spectacular Florida Bay sunsets make for a beautiful investment in island living.

88540 Overseas Hwy Unit APT 304, Islamorada
$609,900
2 Beds ⋅ 2 Baths ⋅ 620243 MLS
Experience the ultimate Florida Keys lifestyle in this bright and spacious townhouse-style condo located in sought-after Executive Bay Club in Islamorada. Ideally situated next to Founders Park, this gated bayfront community offers an unbeatable combination of location, lifestyle, and investment potential. One of the standout features of this residence is the rare open kitchen layout, creating a more spacious and inviting main living area ideal for everyday living or entertaining. EBC is highly desirable for boaters and investors alike, with first-come, first-served dockage available for boats, immediate bay access, and quick ocean access via Snake Creek and Tavernier Creek. Residents and guests enjoy a private sandy beach with beautiful sunset views, plus community amenities that include a renovated pool and clubhouse, tennis courts, pickleball courts, BBQ area, kayak launch, kayak storage, trailer parking, and secure gated entry. Short-term rentals are allowed with a 28-day minimum, making this an excellent opportunity for full-time living, a vacation getaway, or an income-producing property. Located in the heart of Islamorada and within walking distance to Founders Park events, recreation, and nearby dining, this property offers the ideal blend of waterfront enjoyment, boating convenience, and rental flexibility in one of the Florida Keys' most desirable communities.

87200 Overseas Hwy Unit APT A 7, Islamorada
$699,000
1 Beds ⋅ 1 Baths ⋅ 619668 MLS
Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, income-producing property in the heart of Islamorada. This beautifully appointed one king-bedded room with kitchen, private screened in balcony, with owners closet, offers the ideal blend of personal retreat and investment potential. Set within one of the Florida Keys' most celebrated resorts, owners and guests enjoy a true luxury experience, featuring exceptional dining, new ballroom, two tiki bars, a full-service spa, fitness center, and multiple resort-style pools, 9 hole, Par 3 golf course, The property boasts direct beach and dock access, along with lighted tennis courts, pickleball courts and a wide array of water sports, all surrounded by lush tropical landscaping. Nightly rentals are permitted, creating strong income potential, while professional onsite management provides seamless maintenance and guest services. Ideally located just moments from Islamorada's renowned restaurants, galleries, breweries, shopping, and vibrant art district, this is a unique chance to own within one of the Keys' most historic and sought-after destinations.

81801 Overseas Hwy Unit # 729, Islamorada
$635,000
3 Beds ⋅ 3 Baths ⋅ 619364 MLS
Welcome to effortless coastal living in the desirable Executive Bay Club community--where comfort, style, and resort-style amenities come together in a relaxed Keys setting. This nicely updated 3-bedroom plus loft townhouse offers a spacious and versatile layout designed for easy everyday living and entertaining. Upstairs, you'll find three inviting bedrooms, two full baths, and a charming loft--perfect for additional guests, a home office, or a cozy retreat. Downstairs, thoughtful updates create a seamless flow, with a level floor plan that connects the living and dining areas--no step-down interruptions--enhancing both function and openness. The expanded kitchen is a standout feature, showcasing stainless steel appliances, generous counter space, and a peninsula with double-sided storage, ideal for both cooking and gathering with friends and family. A full bath on the main level adds convenience for guests. Beyond your front door, Executive Bay Club offers an array of amenities to complement the coastal lifestyle. Enjoy two tennis and pickleball courts, newly expanded first-come, first-serve dockage for your boating adventures, and a beautifully renovated pool area complete with updated pool deck and bath facilities. The refreshed clubhouse provides an inviting space to relax and connect with neighbors. Whether you're seeking a full-time residence or a weekend escape, this welcoming townhouse delivers the perfect blend of elegance, comfort, and laid-back island living.

87200 Overseas Hwy Unit S3, Islamorada
$665,000
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
$630,000
3 Beds ⋅ 2 Baths ⋅ 619040 MLS
If you're looking for a property with potential in a highly desirable area of Islamorada and are prepared to put in the work, this is an opportunity worth considering. Sellers are motivated and will entertain offers. This 3-bedroom home offers a chance to purchase in one of Islamorada's most desirable areas and update the property to fit your needs, investment goals, or long-term plans. The home sits on an oversized lot and features a functional floor plan with generously sized rooms and a kitchen that opens to the living and dining areas. The concrete construction and larger homesite provide a solid starting point for renovation and improvement. Located directly across from Founder's Park, the property offers convenient access to a bayfront beach, community pool, public boat ramp, baseball fields, playgrounds, dog park, and community events throughout the year. The oversized lot also provides additional outdoor space compared to many nearby properties.

110 E Ridge Rd, Islamorada
$630,000
2 Beds ⋅ 2 Baths ⋅ 617971 MLS
Private location for your pleasure at this roomy townhouse offering an abundance of space to enjoy. Spiral stairs leading to the primary suites with an additional loft for your quests. Soft carpet on the living area floors with tile in the remodeled kitchen and beautiful bathrooms. Two pets allowed, with first come first serve the waterfront area. Pool and club house for your recreation along with a nice, landscaped community for your pleasure. 28-day rentals permitted. Garden setting from you extended living room to enjoy the outdoors at your back yard.

87200 N Overseas Hwy Unit N2, Islamorada