Upper Matecumbe Key Islamorada Homes For Sale on the Ocean Side

MOTIVATED SELLER!! ALL OFFERS WILL BE CONSIDERED!! SELLER OFFERING $10k CREDIT TOWARD CLOSING COSTS!!Welcome to 100 Parker Drive, a delightful 2-bedroom, 2-bath all-concrete home nestled in one of Islamoradas most sought-after neighborhoods. Tucked away between the Overseas Highway and the Old Highway, this quaint, quiet, and family-friendly street is a hidden gem, offering the perfect blend of island charm and small-town community living.This partially updated retreat boasts a private, fenced-in paver patio, ideal for outdoor entertaining, morning coffee, or a peaceful evening under the palms. Surrounded by lush tropical landscaping, it offers a serene escape just minutes from the heart of downtown Islamorada.Whether youre looking for a full-time residence, a seasonal getaway, or an investment property, this home is turn-key and a prime opportunity for both long- and short-term (28 day or more) rentals. The Parker Drive community is vibrant and welcoming, with plenty of families and children, making it an excellent choice for those seeking a neighborhood feel with the perks of island life.Location is everything! From here, you can bike to Islamoradas best restaurants, boutiques, art galleries, breweries, and marinas--all just a short ride away. Take a quick drive to the local schools, parks, and waterfront attractions that make Islamorada one of the most desirable places to call home.Dont miss your chance to own a piece of paradise! This unbeatable location and potential for return on investment make it a rare find in Islamorada. Schedule a showing today!

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!

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.

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.

NEWEST DEVELOPMENT IN DOWNTOWN ISLAMORADA!! Come preview finished units NOW. Only ONE HOUSE LEFT. An exclusive, gated enclave on the Atlantic Ocean, Oceanside is nestled between the Cheeca Lodge and the Caribbean Resort, offering the very best of location, privacy and island living. Low maintenance concrete block construction, this home has been built above flood level. Spacious living area of more than 2,500 square feet, with fully collapsing Euro doors both on the second floor, leading out to a covered balcony, and on the first floor, opening to the private pool and deck, Oceanside House 6 boasts four bedrooms with ensuite baths, plus a first floor powder room. Large open kitchen, island and living area flow seamlessly. The property also allows vacation rentals. This beauty will not last! Make an appointment to visit the site today.Owner is Florida licensed real estate agent.

Seize the rare opportunity to build your dream home in one of Islamoradas most coveted locations! Located directly across from the iconic Alligator Reef Lighthouse. Across the street from a protected preserve that will never be developed, and featuring a deep water channel capable of accommodating boats up to 40 feet, this property offers unmatched privacy and access.Imagine living just a short stroll from the legendary Square Grouper, Midway Cafe, Robbies. Down the road from some of the best restaurants in Islamorada like Ziggies, Mad Dogs, and Chef Michaels. This oversized lot, just shy of an acre, provides the perfect canvas for a builder, developer, or savvy end user to craft a stunning, custom-designed home in an unparalleled location. Dont miss your chance to secure this exceptional piece of paradisean extraordinary opportunity to live where others only dream!

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms, while the fourth is a charming bunk room, perfect for family gatherings.Enjoy a state-of-the-art kitchen that flows into open-concept dining and living areas. Additional features include a powder room, ample closet space, two oceanfront balconies, and a two-car garage with electric charging. Experience maintenance-free living with potential for passive income in a safe, gated environment.The Islands of Islamorada enhances your lifestyle with 615 feet of pristine swimming beach and a private boat basin. Relax at two oceanfront pools, enjoy the oceanfront bar, or play pickleball. Golf enthusiasts can practice at the unique driving range extending into the ocean. Surrounded by lush landscaping, the community offers a variety of water activities to immerse you in the Keys lifestyle.These villas can also participate in a vacation rental program, providing a lucrative investment opportunity with a five-star hotel management company. With a dedicated concierge on-site, every desire can be fulfilled--from seaplane flights to gourmet dinners in South Beach. Discover unparalleled coastal elegance at The Islands of Islamorada, where every moment is a celebration of paradise.

This breathtaking three-story beachfront home boasts six spacious bedrooms and five lavish bathrooms and three living rooms, perfectly blending resort-style living with the utmost comfort. Located in a serene cove with a pristine natural beach, the home features floor-to-ceiling windows that offer stunning 180-degree panoramic views of the ocean. Every corner is meticulously designed with tasteful decor, exuding elegance while providing a personal, comfortable atmosphere. The property is in downtown Islamorada, Florida Keys, and includes a private beachfront terrace, a third-story private balcony, and a tranquil pool with a tiki hut, making it ideal for relaxation and entertaining. The outdoor spaces feature a cozy firepit, offering the perfect setting for intimate gatherings with the sound of the waves as a backdrop. As a vacation rental, this residence is a lucrative investment opportunity in a highly sought-after area. This home is a true masterpiece, offering unparalleled luxury, privacy, and breathtaking views.