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142 Harbor Dr, Islamorada
$1,850,000
3 Beds ⋅ 2 Baths ⋅ 622027 MLS
Experience the ultimate Florida Keys lifestyle in this spacious Islamorada canal front home featuring 70 feet of dockage and a 10,000 lb boat lift! The home offers 3 beds/ 2 baths laid out with 2 bedrooms and 1 bathroom upstairs, plus 1 bedroom and 1 bathroom downstairs, with a bonus convenient laundry / storage area not counted in the Sqft. Relax and Enjoy a large, open porch overlooking the canal under a solid concrete roof, perfect for relaxing and taking in the coastal breezes. Impact-resistant windows and doors throughout provide added peace of mind. Outdoor living is at its finest with a tiki hut, fire pit, jacuzzi, golf course, and even an ice maker to keep your coolers stocked for those perfect boating days! Ample parking provides plenty of room for multiple vehicles and boat trailers. Ideally situated in a friendly oceanside neighborhood near Tavernier Creek, you'll enjoy quick boating access to the bayside in just minutes. Fantastic restaurants, shopping, and everything that makes Islamorada special are right around the corner! This canal front home offers the perfect combination of comfort, convenience, fun and the laid-back Florida Keys lifestyle!

142 Harbor Dr, Islamorada
101 Orange Ln, Islamorada
$735,000
4 Beds ⋅ 3 Baths ⋅ 621604 MLS
Solid Concrete Home on Plantation Key! Live the Islamorada lifestyle from this solid concrete home in a desirable Plantation Key subdivision. The home is ground level and built above flood. It offers 4 bedrooms, 3 bathrooms, a comfortable living area, and a large dining room for entertaining family and friends. Out back, a spacious, fully fenced yard has plenty of room for a pool, a garden, or simply relaxing outdoors. Owners can use the neighborhood HOA park, its boat ramp for direct bay access, with the ocean a short run away and short term dockage. Founders Park is just minutes away, with a swimming pool, sandy beach, boat ramp, playground, dog park, and tennis and pickleball courts. Acclaimed restaurants, shopping, schools, and the hospital are all close by. This home puts you in the middle of everything Islamorada has to offer. Orange Lane is a great fit for investors, renovators, or buyers who want to build equity.

101 Orange Ln, Islamorada
18 Pen, Islamorada
$3,900,000
3 Beds ⋅ 3 Baths ⋅ 621575 MLS
Sunset views in Islamorada's most coveted location: PEN KEY CLUB. From the front doorstep, you can see straight through the house to the sparkling waters of Florida Bay, so the view will take your breath away before you put a foot inside the house! Established in the 1950s, Pen Key Club is a small, private, gated bayfront community on Upper Matecumbe Key, Islamorada's ''downtown'' island. The location is excellent by land and sea. Boating access is exceptional. In fact, it's why the club was founded here. Immediate access to Florida Bay and quick, easy access to the ocean through Whale Harbor Channel. Dockage for boats to 32 feet (plus engines) is available for club members only. Quiet and tucked away, it's close to many of Islamorada's favorite restaurants, including Chef Michael's, Kaiyo and Pierre's, as well as shops and local gathering places like the Cheeca Lodge. Owners share a pool, marina and sunset viewing areas, while the association cares for the landscaping. An onsite property manager receives packages and helps owners with day-to-day needs, making it easy to live here full time or to come and go. Overlooking the marina and bay, this one-level home has high ceilings and two large living areas lined with wide banks of impact glass doors. Expansive bay views extend throughout the main living areas and primary bedroom suite. The large covered patio offers plenty of space for morning coffee, dinner with friends and a front-row seat for the sunset. The comfortable layout puts everything on one floor, with three bedrooms, each with an en suite bath, plus a separate office, laundry room and garage. Concrete construction, impact windows and doors and a metal roof add strength and peace of mind. You really can have it all: big bay views, dockage, excellent boating access and favorite restaurants and shops nearby, with the ease of a single-level home in a peaceful community where living is easy.

18 Pen, Islamorada
80902 Old Hwy, Islamorada
$2,950,000
4 Beds ⋅ 3 Baths ⋅ 621398 MLS
RARE OPPORTUNITY IN CORAL COVE! Welcome to Island Hopper, an award-winning tropical plantation-style home in one of Islamorada's most private gated communities. Set on an oversized double lot, this beautifully updated 4-bedroom, 3-bath home offers 3,550 sq. ft. of living space plus 1,200 sq. ft. of covered outdoor living. A spectacular wraparound porch, soaring windows, and abundant natural light capture the relaxed elegance of Keys living. The private top-floor primary suite features a walk-in closet, Jacuzzi tub, and adjoining office. Recent upgrades include impact windows and doors, four new A/C units, approximately 5,000 sq. ft. of new marble pavers, 7,500 sq. ft. of new turf, and lush tropical landscaping with mature orchids and privacy hedging. Enjoy the privacy of a dry-lot home with the benefits of waterfront living. Coral Cove's amenities include community boat dockage with water and power, fish-cleaning station, oceanfront pool, and tiki huts. Four covered parking spaces plus dedicated golf-cart parking complete the property. Ideally located in the heart of Islamorada, within walking distance of restaurants, shopping, and entertainment. With only 9 homes in Coral Cove, opportunities to own in this special community are exceptionally rare.

80902 Old Hwy, Islamorada
80939 Overseas Hwy, Islamorada
$3,900,000
7 Beds ⋅ 7 Baths ⋅ 621298 MLS
Rare opportunity in downtown Islamorada. This is a development dream property on three quarter of an acre with six transient units,one market rate unit plus a commercial restaurant. Lots of options for redevelopment from restaurant with employee housing to a small boutique hotel with its own eatery. License for more than 200 seats with indoor and outdoor dining and plenty of parking ,opportunities like this in the heart of Islamorada are not available often. This is a must see and won't last .

80939 Overseas Hwy, Islamorada
75433 Overseas Hwy, Islamorada
$3,999,000
4 Beds ⋅ 4 Baths ⋅ 621270 MLS
Wake up to the sunrise over the Atlantic from this private oceanfront retreat offering two separate residences, a sandy beach, and direct access from Highway to Ocean. This unique property offers a 3BD/3BA main residence plus a separate 1BD/1BA guest house, ideal for extended family, visiting friends, private home, or income producing estate. Enjoy a sandy beach, pool, two beachside tiki huts, observation pier, concrete boat ramp and rock jetties for tide protection, creating the ultimate setting for entertaining and waterfront living. Extensive upgrades include impact windows and doors, metal roof, A/C, stucco, paint, appliances and more. With abundant parking for cars, boats, trailers, toys and guests, there is room for everyone. Just minutes by boat to Alligator Lighthouse and nearby Caloosa Marina for fuel, ice, boat storage and food. A rare opportunity to own a true oceanfront Keys compound with space, privacy and a stunning view!

75433 Overseas Hwy, Islamorada
74049 Overseas Hwy, Islamorada
$3,750,000
4 Beds ⋅ 4 Baths ⋅ 620893 MLS
Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property offers the space, privacy, and tropical lifestyle that make the Florida Keys one of the most sought-after destinations in the world. Currently operating as a successful VRBO vacation rental, this turnkey, income-producing property is being sold fully furnished, allowing the new owner to seamlessly continue operating it as a successful vacation rental from day one or immediately begin enjoying it as a private island retreat. Designed with flexibility in mind, this two-story home features a total of 4 bedrooms, 4 bathrooms, and two full kitchens. The upper level offers 3 bedrooms, 2 bathrooms, a full kitchen, and a private balcony, while the lower level offers a handicap-friendly layout, with a 1 additional bedroom, 1 bathroom, a cabana bath, and a second full kitchen. Step outside to your private pool, then take just a few steps to your own private beach, creating the ultimate island experience. A new A/C system and metal roof also adds comfort and peace of mind. Conveniently located just minutes from Robbie's Marina and Theater of the Sea, you'll enjoy world class fishing, boating, snorkeling, waterfront dining, and everything that makes Islamorada one of the premier destinations in the Florida Keys.

74049 Overseas Hwy, Islamorada
84961 Old Hwy Unit A1, Islamorada
$439,000
1 Beds ⋅ 1 Baths ⋅ 620845 MLS
Charming concrete bungalow in the heart of Islamorada! Move right into this beautifully updated 1BR/1BA retreat featuring fabulous ocean views from your private rooftop deck. Blending timeless Florida Keys charm with modern finishes, this home offers durable concrete construction with beautiful interior finishes, impact windows, an updated electrical panel, and parking for two vehicles. Relax under the covered Chickee Hut while enjoying spectacular Atlantic sunrises and unforgettable sunset skies. Community amenities include dock privileges, the Atlantic Ocean Jetty Area, a community Chickee Hut, and a low HOA fee of just $149/month, all conveniently located near Snake Creek Marina. Looking for a weekend getaway, vacation rental, or full-time island escape, this is your opportunity to experience the best of Florida Keys living.

84961 Old Hwy Unit A1, Islamorada
77340 Overseas Hwy, Islamorada
$3,799,999
2 Beds ⋅ 2 Baths ⋅ 619064 MLS
Estate Opportunity Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot size allows a discerning buyer to imagine the best. The site easily accommodates the vision of an estate property with pool, tennis or pickleball court, expansive outdoor living, caretaker's cottage, and generous waterfront dockage--all while maintaining privacy rarely achieved in the Keys. Positioned on a deep basin, the property provides protected dockage while being only seconds from Florida Bay and minutes under the bridge to the Atlantic Ocean, placing world-class backcountry and offshore fishing within immediate reach. An existing legal nonconforming home with a waterfront swimming pool currently sits on the property and may be used as a residence or rental while architectural plans and permits are finalized, offering flexibility during the planning process. For buyers who understand the value of land in the Florida Keys, this offering represents something increasingly difficult to find: the opportunity to create a custom waterfront estate tailored entirely to your vision, rather than inheriting someone else's. A remarkable parcel for a remarkable build.

77340 Overseas Hwy, Islamorada
110 E Ridge Rd, Islamorada
$575,000
3 Beds ⋅ 2 Baths ⋅ 619040 MLS
YES, THIS HOUSE NEEDS SOME WORK -- BUT HOW DOES A 4.9% INTEREST RATE SOUND? For a qualified buyer, the existing VA loan may be assumable at an attractive 4.9% interest rate. And here's the important part: you do NOT have to be a Veteran to qualify for the assumption. Buyer qualification, loan servicer approval, and applicable terms and conditions are required. Now, about the house. This 3-bedroom Islamorada home is livable in its current condition, but it's ready for updating and a new owner's vision. The home is dated and needs a new roof, while its concrete construction, generously sized rooms, functional floor plan, and oversized lot provide plenty to work with. Update it over time or take on a larger renovation and make it completely your own--the choice is yours. Then there's the location--something you can't renovate or replace. Founders Park is directly across the street, putting the bayfront beach, community pool, public boat ramp, sports fields, playgrounds, dog park, and year-round community events practically at your doorstep. This isn't a shiny, newly remodeled home--and that's part of the opportunity. It's a chance to buy in a desirable Islamorada location, add your own improvements and style, and potentially take advantage of an assumable VA loan at 4.9%. Bring your ideas, envision the possibilities, and be sure to ask about the loan assumption.

110 E Ridge Rd, Islamorada
75131 Overseas Hwy, Islamorada
$3,999,000
3 Baths ⋅ 618928 MLS
Beautiful 100' of oceanfront property on Lower Matecumbe Key. This offering consists of a 100' lot with a triplex apartment building (3 TDRs),.This gives you lots of possibilities for redevelopment of the property. Fantastic near 180° ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Note: One of the owners is a State of Florida Real Estate Licensee

75131 Overseas Hwy, Islamorada
150 List St, Islamorada
$4,499,500
1 Beds ⋅ 1 Baths ⋅ 618918 MLS
Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one bedroom and one bathroom - ideal as a weekend escape, guest retreat, or comfortable interim residence while you bring your custom waterfront vision to life. For boating enthusiasts, the estate offers dockage with direct bay access, placing world-class fishing, sandbars, and crystal-clear waters just moments away. A PERMIT HAS BEEN ISSUED to repair and expand the existing dock and add two boat lifts (20,000 lb and 16,000 lb), significantly enhancing the property's boating capabilities and long-term value. Surrounded by multimillion-dollar estate home sales, this offering represents a rare chance to secure a premier bayfront parcel in one of Islamorada's most sought-after locations. With the existing estate slated for demolition and redevelopment, the conceptual renderings unveil a spectacular 4,872-square-foot custom residence offering five bedrooms, five and a half bathrooms, a three-car garage, and a resort style pool - all thoughtfully designed to capture water views from every vantage point. This vision blends refined indoor living with outdoor elegance, creating a seamless waterfront sanctuary. Whether you envision a private coastal retreat or an entertainer's paradise, this remarkable bayfront estate offers endless possibilities in an unparalleled setting.

150 List St, Islamorada
75131 Overseas Hwy, Islamorada
$5,999,000
3 Beds ⋅ 3 Baths ⋅ 608546 MLS
Beautiful 200' of oceanfront property on Lower Matecumbe Key. This offering consists of one 100' lot, vacant with TDR & contiguously, a 100' lot with a triplex apartment building (3 TDRs),.This gives you endless possibilities for redevelopment of the property. The vacant lot has an additional 200' of bay bottom. Fantastic 180° ocean views make for gorgeous sunrises on the naturally sandy beaches. View Alligator Lighthouse, watch dolphins, manatees, and birds feeding on fish right in front of you. At night, beautiful full moon risings, cruise ships with their lights passing, and plenty of stars. Launch kayaks from the beach to do a little tarpon fishing and bonefish are making a comeback so you can wade with your fly rod for a thrill. Also snorkel for lobster in season in all the little crevices and holes off shore of the property. Recap: 200' of oceanfront made up of 1 vacant lot with TDR, 1 lot with 3 apartments, bay bottom on the vacant lot, for a total of 4 TDRs on the property Note: One of the owners is a State of Florida Real Estate Licensee

75131 Overseas Hwy, Islamorada
159 Iroquois Dr, Islamorada
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 618050 MLS
Discover island living at its finest in this beautifully remodeled 3-bedroom, 3-bath ''Florida Modern'' CBS home, ideally located in the desirable Lower Matecumbe Beach neighborhood of Islamorada. A light-filled open-concept layout seamlessly connects the living, dining, and kitchen areas-perfect for entertaining or relaxed island living. The home features three spacious bedrooms and three full bathrooms, including a luxurious primary suite with a sleek modern en-suite bathroom and a large walk-in closet. A versatile bonus room offers endless possibilities as a media room, den, office, or children's retreat. The oversized gourmet kitchen is a chef's dream, showcasing brand-new high-end stainless steel appliances, elegant quartz countertops, and generous storage. Impact-resistant windows and sliding glass doors provide peace of mind while enhancing the home's clean, contemporary style. Step outside to your private backyard and enjoy peaceful sunrise views or savor coffee and cocktails beneath the shaded gazebo. Boaters will love the newly decked 60-foot dock, offering immediate access to both the Atlantic Ocean and Florida Bay. From watching manatees glide by to cleaning the day's catch at the large fish station, every detail is designed for waterfront living. There is enough space to have an in-ground pool. An added bonus is the voluntary HOA, which provides access to a wide sandy beach, known as a turtle-nesting haven. Welcome to your place in paradise. 🌴

159 Iroquois Dr, Islamorada
105 Palm Ave, Islamorada
$4,600,000
1 Beds ⋅ 4 Baths ⋅ 618814 MLS
This is an exceptionally rare chance to secure a versatile mixed use commercial property in Islamorada's most established business corridors. Sale does not include real estate business. These three building and the land are ideally positioned for a wide range of commercial uses. Its central location within the Village of Islamorada provides strong access to both local residents and year-round visitor activity, making it an appealing option for investors and owner-operators. The building features a practical, adaptable layout suitable for professional offices, medical or wellness services, boutique retail, administrative operations, or specialty businesses. Large front-facing windows bring in natural light and enhance street presence, creating an inviting entry point for customers and clients. The interior opens into a flexible main area that can function as a reception space, retail floor, open office environment, or showroom. The footprint also supports the creation of private offices, treatment rooms, or storage areas, allowing businesses to tailor the space to their operational needs. On-site parking adds significant value, providing convenient access for customers and employees--an important advantage in Islamorada's commercial zones. Excellent signage opportunities ensure strong brand exposure. Easy ingress and egress make the location suitable for both destination-based and walk-in business models. Surrounded by established businesses, restaurants, marinas, and residential neighborhoods, the property benefits from a diverse and active customer base. Islamorada's strong local economy and tourism-driven demand enhance the long-term appeal of this location. With limited standalone commercial inventory available in the Upper Keys, 81579 Old Highway offers a unique setting for multiple uses within walking distance to Cheeca Lodge, The Moorings, and Worl Wide Sportsman. Totally renovated in 2019. Virtual tour www.166bayviewdrive,com

105 Palm Ave, Islamorada
114 Sunset Dr, Islamorada
$2,750,000
3 Beds ⋅ 4 Baths ⋅ 618633 MLS
Tastefully updated canal-front pool home on beloved Sunset Drive! This delightful residence was recently remodeled from top to bottom by a local and renowned builder and features a bright open floor plan, modern kitchen with stainless steel appliances, and coastal-inspired finishes throughout. Bonus pre-firm 1BA/1BA downstairs. The exterior offers a private pool, spacious lounging areas, and substantial dockage suitable for a large vessel, providing immediate access to open water. Clean lines, natural light, and thoughtful updates create a move-in-ready retreat to relax and absorb the peacefulness of island life. Don't miss this delightful waterfront offering in one of the Florida Keys' most desirable boating locations!

114 Sunset Dr, Islamorada

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