Upper Matecumbe Key Islamorada Florida homes for sale starting at Fifty Thousand Dollars

$2,695,000 - Upper Matecumbe Key Islamorada, FL

82762 Overseas Highway Upper Matecumbe Key Islamorada, FL - Open Bay Views, Boat Dockage and more... all in the Heart of Downtown Islamorada! Have you been dreaming of living downtown, but can't find a home with dedicated boat dockage and open water views? If so, this custom home in Madeira Bay is your dream come true! Enjoy open water views from the porch, living room, kitchen, loft and bedroom plus soaring ceilings and lots of living space. The Madeira Bay gated community is a hidden treasure of only 8 homes tucked in behind one of Islamorada's most beloved local restaurants in a peaceful private neighborhood. In addition to the community dock there is also a community pool and a gradual shoreline for launching a boat, paddle board or kayak or for wading directly into the bay with your rafts and floats! Stunning great room opens to the bay view porch on the main living level where there are also three bedrooms and two full baths in a split plan. There is also an open loft bedroom with full bath upstairs off the great room featuring beautiful bay views. The fully permitted downstairs is connected by internal spiral stairs and adds a separate ground level entrance plus a spacious second living room, wet bar area for entertaining, plus a private guest bedroom with a full bath and outdoor porch. There is also an attached garage for protected parking and/or storage. The downtown location offers immediate access to shopping, fine dining, bars, galleries, art studios and all the regular local art festivals, full moon parties and events. Madeira Bay homes rarely come on the market and this one is a must see!

$1,699,000 - Upper Matecumbe Key Islamorada, FL

36 Park Road Upper Matecumbe Key Islamorada, FL - Stunning new custom home in the heart of Islamorada. This exceptional, brand-new ground-level home was thoughtfully designed and expertly crafted with meticulous attention to detail. A professional interior designer curated high-end fixtures and elegant finishes throughout, creating a polished and inviting living space.Offering a rare 4-bedroom, 3-bathroom split floorplan, the home features a spacious open-concept layout ideal for both everyday living and entertaining. Soaring 10-foot vaulted ceilings and oversized 8-foot doors define the home's modern architectural style.Additional highlights include a two-car garage, a heated swimming pool, and quality construction that sets a new standard for homes in the area.Located in desirable downtown Islamorada, you're close to popular restaurants, shopping, a grocery store, and a beloved brewery. With new construction permits currently suspended in Islamorada, opportunities like this are becoming increasingly rare.Don't miss your chance to own one of the last newly built homes in this prime location - this property truly checks all the boxes.

$1,600,000 - Upper Matecumbe Key Islamorada, FL

100 Seashore Drive Upper Matecumbe Key Islamorada, FL - Welcome to Turtle's 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.

$1,400,000 - Upper Matecumbe Key Islamorada, FL

131 Ocean Lane Upper Matecumbe Key Islamorada, FL - 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.

$1,300,000 - Upper Matecumbe Key Islamorada, FL

81216 Old Highway Upper Matecumbe Key Islamorada, FL - 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. Don't 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!

$1,200,000 - Upper Matecumbe Key Islamorada, FL

83201 Old Highway Upper Matecumbe Key Islamorada, FL - Welcome to Unit #409 at Beacon Reef, an oceanfront gem located in the heart of Islamorada. Beacon Reef is well-run, meticulously maintained, and units are rarely available for a reason. This beautifully appointed 2-bedroom, 2-bathroom residence offers approximately 1,275 square feet of comfortable, coastal living. The primary suite features a king-sized bed, en-suite bathroom, and direct access to a private balcony with sweeping ocean views, while the guest bedroom provides space for two queen-sized beds and a generous closet. The open-concept living area flows effortlessly into a fully equipped kitchen with granite countertops, and a breakfast bar, complemented by a formal dining area. Additional conveniences include an in unit laundry area with full-sized washer and dryer, impact windows, and a spacious screened-in balcony.Beacon Reef is a gated, resort-style community offering a wealth of amenities, including a beach-entry heated pool, therapeutic hot tub, ocean-view fitness center, and a deep water private marina with boat slips available for vessels up to 35 feet (first-come, first-served). Residents also enjoy a sandy beach, fishing pier, BBQ area under the tiki hut, and lush tropical landscaping throughout the property. Ideally located, this unit is just minutes from Islamorada's world-class fishing, diving, restaurants, galleries, and marine attractions, offering both seclusion and convenience. Whether you're seeking a permanent residence, weekend retreat, or seasonal getaway, Unit #409 is your invitation to live the Florida Keys lifestyle.

$1,150,000 - Upper Matecumbe Key Islamorada, FL

82260 Overseas Highway Upper Matecumbe Key Islamorada, FL - MOTIVATED SELLERS! Paradise Found: Renovated Jungle Treehouse in Islamorada. This fully renovated CBS home blends modern upgrades with Old Florida charm in a peaceful secluded location. Featuring 3 bedrooms, 3 full baths, and a large downstairs flex space, it's perfect for relaxing or entertaining. Set on an oversized 15,000+ sq ft lot with lush landscaping and a rooftop deck, the home feels like a private retreat. Upgrades includes, new buried electrical lines and panels, and impact windows throughout. Enjoy access to a shared day dock with a full easement--great for kayaking, swimming, or fishing in the bay. (Note: boating rights not included.) Located in the heart of Islamorada, this home offers elegance, privacy, and island living at its finest.

$825,000 - Upper Matecumbe Key Islamorada, FL

100 Parker Drive Upper Matecumbe Key Islamorada, FL - 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 Islamorada's 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 you're 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 Islamorada's 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.Don't 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!

$725,000 - Upper Matecumbe Key Islamorada, FL

81801 Overseas Highway Upper Matecumbe Key Islamorada, FL - ***Seller Financing now an option! ***Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the ''Sportfishing Capital of the World''. Condo Features -This spacious King Bed Suite offers a large living room area with a pull-out queen bed, a grand bathroom with walk-in shower and soaking tub, a fully equipped kitchenette, and a private screened in porch with views of the lush landscape and large coconut palms. This exceptional income-producing property allows nightly rentals. Owners use their units up to 28 days a year and receive a monthly check for the remainder of the time. It's a hands-off income generator!The Resort -Enjoy 27 acres of Islamorada oceanfront that include 3 world class restaurants, 2 open-air tiki bars, 1,200' of private beach, 525' fishing pier, 2 family pools, 1 adults only pool, beach and pool side cabanas, 9 hole golf course designed by Jack Nicklaus, 6 sports courts, 15,000 sqft of event space, valet parking, 24 hour shuttle service, concierge service, on site boat trailer parking, watersports activities, fitness center and Camp Cheeca.

$725,000 - Upper Matecumbe Key Islamorada, FL

79901 Overseas Highway Upper Matecumbe Key Islamorada, FL - Fabulous top floor location with spectacular ocean views! This spacious condo has tile floors throughout and a lovely open terrace to enjoy the ocean view and breezes. Both bedrooms are spacious and the primary bedroom opens to the oceanfront terrace. The Palms of Islamorada is conveniently located close to the downtown Islamorada area. You are only minutes from enjoying shopping in the boutiques and galleries and eating in numerous restaurants that are very close by. The Palms has an oceanfront pool, hot tub, assigned parking with plenty of guest parking, 2 gyms as well as kayak and paddleboard storage. A fantastic view of Alligator Lighthouse is included at no extra cost.

Upper Matecumbe Key Islamorada, Florida listings for sale

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