Upper Matecumbe Key Islamorada Homes For Sale on the Ocean Side

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!

Historic and charming 1936 Red Cross Home - Fully Remodeled - on 1/2 acre - in the heart of town! Step into history with this beautifully remodeled 1936 Red Cross home, originally built by the Red Cross to shelter hurricane survivors. Constructed entirely of concrete, including a solid concrete roof topped with durable metal, this home is built to last. Modern upgrades include impact windows and doors for added security and energy efficiency. Situated on over half an acre with tropical landscape in the heart of town, this 2-bedroom, 1-bathroom home offers both historic charm and modern convenience. The fully updated interior blends timeless character with contemporary comforts, making it move-in ready. Located on a road popular with walkers, joggers, and bicycle riders, this home is just moments from many shops, restaurants, and the vibrant Morada Way Arts District. Close to world famous Cheeca Lodge and the newly renovated Islander Resort which welcomes locals to its beach/pool bar and restaurants. With plenty of room for a pool or future expansion, the possibilities are endless. RV hookup. Dont miss this rare opportunity to own a true Florida treasure!

Your Slice of Paradise Awaits in Downtown IslamoradaDiscover the perfect blend of modern coastal living and convenience with this beautifully remodeled ground-level duplex in the heart of Islamorada. Located just a moment from the famous Cheeca Lodge and the vibrant Arts District, youll be surrounded by charming shops, restaurants, and galleries.Property Highlights: Two Separate Units PLUS a Guest Space: Each of the two dwellings is thoughtfully designed with a bright, airy ambiance to complement the island lifestyle. Use one unit for yourself and rent out the other, and/or welcome family and friends to visit! Durable Construction: Built with concrete and topped with a sturdy metal roof, this home is designed to withstand the elements. Impact windows and doors provide added protection and energy efficiency. Private Outdoor Oasis: The fully fenced yard features an electric gate, artificial turf for low maintenance, and lush landscaping with vibrant tropical foliage, perfect for relaxing or entertaining.Why Youll Love It:Whether youre looking for a permanent home or a vacation retreat, this property delivers the ideal Florida Keys lifestyle. The Village of Islamorada recognizes two dwelling units, adding significant value to the property.Dont miss your chance to own this coastal gem in an unbeatable location! Buyers should be able to convert this building in to one single-family home and transfer one of the building rights to another Village non-waterfront lot that is deemed appropriate by the Village. Two units are recognized by the Village. Buyers must confirm all with Village of Islamorada.

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.

Location, Location, Location. Welcome to one of downtown Islamoradas most exclusive properties- a spacious estate thats hitting the market for the first time in generations. This ranch-style home sits proudly on four contiguous lots in the peaceful Grove Park Subdivision, offering something thats increasingly scarce in the Keys: space to breathe. With two bedrooms, a 3rd Bedroom option, and an oversized garage (50 x 26) thats perfect for an artists studio with office Loft, boat and car storage plus a Workshop, and Utility buildings. Space to park your RV or Camper. This property gives you room to live and create.Step outside and youll find yourself in a tropical paradise. Fruit trees dot the landscape, and carefully planned gardens create a private sanctuary. Lounge in your Gazebo and an in-ground pool (25 x 40) beckons on those warm Florida afternoons, while the lush landscaping ensures your privacy from the world beyond.Take a short stroll and youre in the vibrant heart of Islamorada. Wander through Artists Alley, browse local shops, or treat yourself to dinner at some of the Keys finest restaurants - all just minutes from your front door.This property isnt just a home - its a blank canvas of possibilities in paradise. And with properties like this becoming increasingly rare in the Keys!

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.

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.