Misc Upper Matacumbe (82.0) Real Estate, Homes, Condos for Sale in Islamorada, FL

3 Beds ⋅ 2 Baths ⋅ 620603 MLS

Welcome to 154 Biscayne Boulevard in the heart of Islamorada. This beautifully maintained 3 bedroom, 2 bathroom concrete home is designed for those who want to enjoy life on the water. Located in the highly sought after Port Antigua neighborhood, this home offers the perfect balance of comfort, durability, and island living. Whether you are searching for a full time residence, a weekend retreat, or an investment opportunity in the Florida Keys, this is your chance to own a piece of paradise and experience everything Islamorada has to offer. Built for lasting peace of mind, the home features a concrete roof, full impact windows and doors, and an inviting open concept floor plan that seamlessly connects the kitchen, dining, and living areas. Natural light fills the space, creating a bright and welcoming atmosphere that is perfect for everyday living or entertaining family and friends. Step outside to the spacious screened balcony overlooking the canal, the perfect place to enjoy your morning coffee or unwind in the evening while taking in the tropical breeze. Downstairs, the covered outdoor living area offers exceptional space for entertaining, relaxing after a day on the water, or storing everything you need for the Florida Keys lifestyle. For boating enthusiasts, this property features a concrete dock with two boat lifts, and quick access to some of the best fishing and boating waters in the world. A large enclosed storage area provides plenty of room for fishing gear, paddleboards, diving equipment, and all of your essentials.

154 Biscayne Blvd, Islamorada

$13,750,000

5 Beds ⋅ 7 Baths ⋅ 620590 MLS

Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by renowned architects Charles Vincent George occupies 1.27 private acres with panoramic open-water views, spectacular year-round sunsets, protected boat basin, solar panels and a rare sandy beach area. Designed to maximize its exceptional setting, the residence offers seamless indoor-outdoor living with floor-to-ceiling impact-rated glass, expansive covered terraces, and walls of retractable sliders that frame breathtaking bay views from every room. A dramatic floating staircase, 12-foot interior doors, engineered hardwood flooring, and superb designer finishes define the home's clean contemporary design. The main residence features 4 bedrooms all ensuite, and 1 half bath. It is complemented by a detached 1-bedroom, 1-bath guest house. The kitchen features quartz countertops, premium Miele and Thermador appliances, and a hidden walk-in pantry. Upstairs is a spacious family/media or fitness room that leads onto a large deck with exquisite views of Florida Bay. Separate laundry/storage room. Fully integrated Loxone Smart Home system controls lighting, security, audio, and six independent HVAC climate zones. Outdoor amenities include an elevated heated and chilled 50FT saltwater lap pool, expansive entertaining terraces, mature tropical fruit trees & landscaping, an air conditioned garden shed, architectural landscape lighting, and a gated entrance ensuring exceptional privacy. The protected boat basin features a composite dock, 12,000 lb boat lift, with immediate access to world-class fishing & diving. At the front is an oversized air-conditioned garage with EV charging & a half bath. A covered carport is adjacent to the main house. A rare opportunity to acquire one of Islamorada's premier contemporary bayfront estates, combining exceptional architecture, outstanding construction and spectacular sunsets.

19 Avacado St, Islamorada

$1,295,000

6 Beds ⋅ 3 Baths ⋅ 620458 MLS

3 plex ( 3 separate units) in the heart of downtown Islamorada. A total of 6 bedrooms and 3 baths. Two of the units are remodeled. Walk to Shopping, Boutiques, Bars, Restaurants, World Wide Sportsman/Bas Pro Shops, Florida Keys Brewery. Or take your street legal golf cart. Currently fully rented on annual leases. Would make great 30 days rentals or really great employee housing. Do not miss this opportunity. Two separate electric meters and one water meter.

81160 Old Hwy, Islamorada

$1,199,000

3 Beds ⋅ 3 Baths ⋅ 619848 MLS

Experience all that Islamorada has to offer from this stunning home that was constructed in 2020. This two-story residence offers 3 spacious bedrooms and 2 full bathrooms on the ground floor. The second floor has a large great room - ideal for a home office, second living room, playroom, or media space--adding extra versatility to the layout. Additionally, there is another full bathroom upstairs. Step into an open-concept main living area with numerous windows to let in the natural light. Easy to clean tile throughout. The heart of the home is a modern kitchen featuring a large island, custom cabinetry, and premium finishes--perfect for entertaining and everyday living. The spacious side and backyard provide ample space for trailers, boats, or a future pool, making it perfect for outdoor enthusiasts. Speaking of pool, there is a current, valid pool permit that has been issued for the property and can be transferred to the next owner. This home is located just minutes from the ocean, marinas, shopping, and dining. It is zoned for highly rated Coral Shores High School. This home offers the rare opportunity to own an almost new, move-in-ready property in the Upper Keys. Don't wait--schedule your private showing today and make this modern island retreat your forever home!

143 N Hammock Rd, 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

$350,000

619014 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

$15,950,000

6 Beds ⋅ 8 Baths ⋅ 618816 MLS

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWS Welcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters. The residence includes 6 bedrooms, 7.5 bathrooms and was designed to blend coastal elegance with effortless waterfront living. In addition to the bedrooms, the main home provides a complete gym and office. A separate guest house includes a living room, full kitchen, laundry room, and two bedrooms with ensuite bathrooms. Located in the heart of Islamorada, the home is walkable to several restaurants. Agents Welcome

20 Avacado St, Islamorada

$12,000,000

5 Beds ⋅ 7 Baths ⋅ 618003 MLS

Situated bayfront on an expansive 1.27-acre parcel, this striking contemporary residence commands breathtaking open-water views from every room. Built in 2017, the home stands sentinel over the bay, defined by clean modern lines, walls of glass, and seamless indoor-outdoor living. Floor-to-ceiling impact-resistant sliders frame ever-changing water vistas, while retractable blinds and soaring 12-foot interior doors enhance light, scale, and flow throughout. Designed by Charles Vincent George and built by Zee Hopman, the residence blends cutting-edge design with warmth and livability. Cool modern architecture is thoughtfully grounded by earthy tones and softened with cozy farmhouse-style furnishings and curated antiques, creating a welcoming contrast that feels both sophisticated and inviting. The main home offers 4 bdr and 4.5 baths, complemented by a separate 1-bdr, 1-bath guest house, ideal for extended family or guests. The heart of the home is a chef's kitchen featuring quartz countertops, premium Miele and Thermador appliances, a walk-in pantry, and engineered hardwood flooring throughout. Additional highlights include a laundry room, family/exercise room, and a Loxone Smart Home system with two HVAC systems and six climate zones for effortless comfort and efficiency. Outdoors, the property is a private tropical retreat. An elevated, heated, chilled saltwater pool is surrounded by an expansive patio perfect for entertaining, while lush landscaping, gated entry, and ambient night lighting create a serene, resort-like atmosphere. Boaters will appreciate the protected boat basin, composite dock, and 12,000 lb. boat lift, offering direct access to open water. Additional amenities including solar panels, climate-controlled garden shed, carport, and an oversized air-conditioned garage with electric vehicle charging and motorhome hookup. This is a rare offering—an architecturally significant bayfront home that marries modern innovation, exceptional waterfront living

19 Avacado St, Islamorada

$1,200,000

3 Beds ⋅ 2 Baths ⋅ 614683 MLS

Ideally located in the heart of Islamorada, this charming home is perfectly updated with a harmonious blend of old and new Keys characteristics and a light and airy layout and enclosed sun room that brings the lovely landscaping inside! A serene pool and oversized backyard with plenty of privacy provide book ends to lovely days of beat the heat splashes during the day and evenings of peace and relaxation in this magical nighttime retreat. This solid CBS house has a reinforced concrete roof, impact windows and doors, and a spacious garage. This 3 bedroom/2 bathroom abode is built with island living in mind with peaceful surroundings and walking or biking distance to all that ahhhmazing Islamorada has to offer.

32 Park Rd, Islamorada

$1,635,500

3 Beds ⋅ 4 Baths ⋅ 610448 MLS

Little Basin Key Lime Villa #1 is a beautifully appointed, 3 bedroom, 3.5 bath townhome with proven rental income. Nestled amongst a quaint row of rocking chair adorned porches, this residence's design takes inspiration from Old Town Key West and features postcard views of sunset from deck and docks. The immaculate, tropically landscaped grounds lead to the shared dockage, pool, tiki hut, and cabana. Parrot fish and mangrove snapper swirl around the waterfront with room for boats up to 30 ft, and a floating dock for guest use. Located on Upper Matecumbe Key, Bayside, in the 'Heart of Islamorada, ' the compound is right next door to Library Beach and is situated within walking distance to the best local sunset venues in the American Caribbean. Watch Sunset Celebrations each day and Full Moon Parties. Not to Mention Wildlife from your private porch! Across, on the Oceanside of the island, The 'Morada Way Art Walk is every Third Thursday and many local boutiques, breweries and fine dining restaurants are within walking distance. The first floor is designed in an open concept with soaring ceilings featuring dining area, kitchen, half bath and guest bedroom with ensuite bathroom. Upstairs leads to two more bedrooms with ensuite bathroom, and the master bedroom features French doors leading to lovely covered porches. Fully furnished in immaculate white decor Boats allowed at dock on a first reserve, first serve basis. Legal Weekly Vacation Rental with 3 master ensuites no need to share a bathroom here. - come stay for a week and rent every other week legally .... or, come and stay forever! Past 6 Months over $86k in rental income alone.

84 Johnston Ave Unit 1, Islamorada

$22,500,000

7 Beds ⋅ 9 Baths ⋅ 618525 MLS

Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla House overlooks 500+ feet of pristine Florida Bay waterfront. New custom construction melds traditional Caribbean architecture with clean modern aesthetics. The over 8,800 square feet of air conditioned living space is thoughtfully designed with bright open interiors which blend sophistication and comfort while framing breathtaking views of Florida Bay. You enter a sunlit two-story foyer leading you upstairs to a bespoke great room, encapsulating a dramatic vaulted wood ceiling, spacious living area, and a custom gourmet chef's kitchen. Floor to ceiling glass doors frame an unobstructed view of the spacious bay-view terrace, which features a 50 foot elevated infinity edge swimming pool and outdoor kitchen with bar. On the upstairs level you will also find a serene primary suite, five generous en-suite guest bedrooms, a powder room, and a large laundry room. The lower level offers a separate one bed en-suite with its own entrance and patio. A media room with adjoining bathroom is the ideal flex space. A 1,600 square foot three car garage and a carport area completes the lower level. All told, there is nearly 25,000 square feet under roof cover. The estate's tropical grounds are designed to complement the home's architecture. A private floating dock offers unimpeded views of Florida Bay. Located in the heart of Islamorada, this property offers rare walkability to some of the village's most recognizable attractions. This location allows you unparalleled access to the best of Islamorada's dining, entertainment, and waterfront lifestyle. Isla House represents a rare opportunity to own one of Islamorada's most unrivaled, captivating, and serene waterfront estates—a sanctuary of elegance, craftsmanship, and timeless island charm.

81486 Overseas Hwy, Islamorada

$3,560,000

4 Beds ⋅ 5 Baths ⋅ 608508 MLS

AUCTION BIDDING OPEN: BIDDING ENDS TODAY 12/5/24 4pm. PREVIOUSLY LISTED AT $5.5M.CURRENT HIGH BID $2.85M. Showings By Appt. Opulent and stylish island castle; the epitome of class and luxury make this home one to remember. Located on a quiet and private island with only three residences, your secret great escape tucked away in the heart of downtown Islamorada awaits. Adorned with Swarovski crystal chandeliers, beautiful finishings sweeping staircase, elevator, 9 hole golfing green, 5 car garage, extreme storage options and parking, double living rooms, open and spacious relaxing and entertaining verandas throughout, third floor primary suite, and multiple ample docking areas example just a few rarities this property has to offer. Two docks, one with lift. Excellent boating location.

80908 Overseas Hwy, Islamorada

$4,800,000

3 Beds ⋅ 3 Baths ⋅ 607157 MLS

For statistical purposes.

189 Avacado St, Islamorada

$2,800,000

4 Beds ⋅ 3 Baths ⋅ 617267 MLS

Excellent price adjustment and ready for you to fall in love!! Premier Islamorada location! Exceptional waterfront property within the quaint gated neighborhood of Coral Cove. Just a step away from the ocean, this concrete home built with a concrete roof, offers 4 bedrooms and 3 baths, configured with 2 bedrooms and 2 baths upstairs, and a 2 bedrooms, 1 bath guest suite located downstairs. Tile floors throughout, updated kitchen, granite counters, brand new AC system, split bedroom, expansive outdoor space, and captivating ocean views! Walk or bike to Islamorada's local restaurants, shops, bars, and Events. Watch the stars at night, and greet the manatees and lobster that frequent this waterfront. This residence also includes a garage, outdoor entertaining, tiki hut, private dockage for appx 27ft boat, tropical landscaping, and low maintenance property. Being offered furnished. The community of Coral Cove offers its 10 homeowners an oceanfront pool, community dockage, and private gated entrance. Don't miss out on this incredible opportunity to own your private waterfront home in the heart of Islamorada. This impeccable residence shows beautifully!

80909 Old Hwy, Islamorada

$2,425,000

3 Beds ⋅ 4 Baths ⋅ 617758 MLS

Welcome to Coral Cove Residence 3, perfectly positioned in the heart of Islamorada. This turn-key, thoughtfully designed three-bedroom, three-and-a-half-bath residence was built in 2020 and features quality construction and well-appointed appliances throughout. A beautiful open floor plan allows natural light to flow effortlessly, creating an inviting coastal living environment. Located within Coral Cove, a private bayfront community of just eight residences, this home offers both exclusivity and convenience. The residence boasts its own private pool, ideal for relaxing or entertaining, while the community also features a stunning bayfront pool with sweeping sunset views over the water. An assigned boat slip in the community marina provides easy access to the bay and ocean beyond, perfect for boating, fishing, and enjoying life on the water. Weekly rentals are permitted, making this an excellent opportunity for a vacation home that can offset carrying costs, an income-producing investment, or a combination of both. The intimate, well-maintained community offers a peaceful retreat while remaining within walking distance to Islamorada's dining, art galleries, boutiques, and local attractions. A rare opportunity to own a turn-key property in one of downtown Islamorada's most desirable bayfront communities.

81906 Overseas Hwy Unit 3, Islamorada

$1,600,000

3 Beds ⋅ 4 Baths ⋅ 608752 MLS

Little Basin Key Conch Villa #6 is a beautifully appointed, 3 bedroom, 3.5 bath townhome with proven rental potential. Nestled amongst a quaint row of rocking chair adorned porches, this residence's design takes inspiration from Key West Coastal Conch-Style and features postcard views of sunset from deck and docks. The immaculate, tropically landscaped grounds lead to the shared dockage, pool, tiki hut, and cabana. Mangrove snapper swirl around the waterfront as manatee ride the current of the natural creek with room for boats up to 30 ft, and a floating dock for kayak launching. Located on Upper Matecumbe Key, Bayside, in the 'Heart of Islamorada,' the compound is right next door to Library Beach and is situated within walking distance to the best local sunset venues in the American Caribbean. Watch Sunset Celebrations each day and Full Moon Parties each month from your private porch! Across, on the Oceanside of the island, The 'Morada Way Art Walk is every Third Thursday and many local boutiques, breweries and fine dining restaurants are within walking distance. Floor Plan: The first level is designed in an open concept with soaring ceilings featuring dining area, kitchen, halfbath(powder room) and queen guest bedroom with ensuite bathroom. Upstairs leads to two more king bedrooms with ensuite bathroom, and the master bedroom features french doors leading to lovely covered porches. Fully furnished in immaculate white decor ... Conch Villa 6 is in the middle 4th one from the waterfront. Frequently rented, Appointment required. Do not enter. March is completely booked, can view late February or after March.

84 Johnston Ave Unit 6, Islamorada

$2,000,000

617671 MLS

PRIME LOCATION IN DOWNTOWN ISLAMORADA! The oversized lot is CLEARED and offers 78 feet of US Hwy 1 frontage and a total of 18,385 square feet. Many options for parking, storage or development.

81213 Overseas Hwy, Islamorada

$2,083

607707 MLS

Prime commercial retail space in the heart of Islamorada! Min. of 1,000 SF of commercial space which is expandable to 2,000 SF based on your needs. Great visibility on RT 1 / Overseas Hwy, Ground floor unit . Zoned Village Center. $25 per SF (annually) + NNN + plus sales tax.

82681 Overseas Hwy, Islamorada

$5,400,000

5 Beds ⋅ 4 Baths ⋅ 608986 MLS

This remarkable property is located in Islamorada's downtown area and offers unparalleled waterfront living. Situated on 1.24 acres of prime real estate, with an impressive 100 feet of bay frontage, this estate blends privacy, tranquility, and breathtaking views of the sparkling Florida Keys waters. The property features two distinct ground-level homes, each with its unique charm and character. The main house, built in 1967, offers three bedrooms and two baths, with ample space for comfortable living and entertaining. Adjacent to the main residence is a guest house complete with two bedrooms, two baths, and a fully equipped kitchen, perfect for accommodating guests. Step outside onto the landscaped grounds with lush, mature foliage, creating a serene oasis for relaxation and enjoyment. The property is secured with gated entry and fencing, ensuring privacy and peace of mind. Boating enthusiasts will delight in the deep water dockage, providing direct access to the pristine waters of the bay and beyond. With neighboring properties conveying multimillion-dollar sales, this is a rare opportunity to own a slice of paradise in one of Islamorada's most coveted locations. Whether you're seeking a permanent residence, vacation retreat, or investment opportunity, this property offers the ultimate waterfront living, where luxury meets lifestyle in perfect harmony.

18 Avacado St, Islamorada

$650,000

2 Beds ⋅ 2 Baths ⋅ 613780 MLS

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!

100 Parker Dr, Islamorada

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Misc Upper Matacumbe (82.0) Real Estate & Homes