Islamorada FL Lots, Land for Sale

A rare opportunity to own an expansive bayfront parcel at Mile Marker 81 on Upper Matecumbe Key, offered for sale for the first time since its acquisition in 1937. Located in the heart of Islamorada, this remarkable property encompasses approximately 5.26 total deeded acres, including approximately 2.84 acres of upland, with more than 250 feet of frontage on Florida Bay. The substantial acreage and natural setting offer exceptional privacy and seclusion, while still being close to the restaurants, marinas, shops, galleries, and world-class boating and fishing that define the Islamorada lifestyle. With its coveted Upper Matecumbe Key location, expansive bayfront, and rare parcel size, this is an extraordinary opportunity to create a private waterfront estate in the Florida Keys. Zoned Native Residential (NR), allowing single-family residential use subject to applicable Village requirements. Allowable clearing, building area, and development potential are subject to applicable Village of Islamorada regulations. Buyer to independently verify all development potential with the Village of Islamorada.

Overseas Highway, Islamorada

$15,000,000

621011 MLS

Discover an extraordinary opportunity on Florida Bay in Plantation Key, offering a rare combination of privacy, natural beauty and approximately 1,250 feet of waterfront with sweeping open-water views and spectacular sunsets. The property encompasses 21+ acres, with approximately 5 acres already cleared for the homesite and improvements. The remaining acreage creates an exceptional natural backdrop and sense of seclusion rarely found in the Florida Keys. A private drive winds through the tropical surroundings to the homesite, while a completed observation dock offers a beautiful setting to enjoy Florida Bay. Designed for this remarkable property is an exceptional 8-bedroom luxury residence created for sophisticated Keys living. Plans feature eight bedroom suites, expansive living and entertaining spaces, a chef-inspired kitchen with oversized island, private office, game room, elevator, extensive garage and storage areas, covered balconies and terraces, plus a pool and spa with generous outdoor living areas. For a buyer who purchases prior to completion, a unique opportunity awaits. The seller will pay the building costs for the planned residence, subject to the terms, specifications and allowances of the purchase agreement. Depending on the stage of construction, the buyer may also have the opportunity to personalize available finishes, selections and certain design elements. Ideally positioned near Snake Creek, enjoy convenient Bay-to-Ocean access with no fixed-bridge restriction and proximity to Founders Park. A remarkable opportunity to create a private Florida Bay retreat where luxury, privacy and the natural beauty of the Keys come together in one exceptional setting.

86600 Overseas Hwy, Islamorada

$2,800,000

620931 MLS

Rare oceanfront Pristine parcel offering approximately 0.56 acres (100 x 244') with 100 feet of Pristine Atlantic Shoreline and active building permit for your dream home/estate. Features a new 80-plus foot dock with a tiki hut and direct access to world-class fishing, diving, snorkeling, and boating. Enjoy sweeping sunrise views over the beautiful Atlantic Ocean and sightlines to the iconic Alligator Reef Lighthouse. Situated on prestigious Millionaire's Row and adjacent to protected preserve land for privacy. Directly across to famous Robbie's Marina and market place ,dining, shopping, and local attractions. An exceptional setting to build a custom waterfront estate in one of Islamorada's most desirable location.'

77481 Overseas Hwy, Islamorada

$3,600,000

620556 MLS

RARE WATERFRONT OPPORTUNITY! With BPAS allocations becoming increasingly limited, this is your chance to build the waterfront home of your dreams in the prestigious Venetian Shores, one of islamorada's most desirable boating communities. This oversized 8,700+ sq ft. waterfront lot offers significant advantages with house permits APPROVED and ready for pickup and the dock permit close to approval, allowing you to build almost immediately. Boaters will appreciate the exceptional access to both the Atlantic Ocean and Florida Bay, making it easy to spend your days offshore fishing, diving, snorkeling, or exploring the renowned backcountry waters of the Florida Keys. Whether you're envisioning a luxury full-time residence of the ultimate island getaway, this is a rare opportunity to build in one of the Keys' premiere waterfront neighborhoods.

101 Stromboli Dr, Islamorada

$3,900,000

620460 MLS

A truly once in a generation opportunity to build your dream estate in the heart of Islamorada's coveted Lower Matecumbe. This exceptional vacant homesite is one of the few remaining parcels of its size available in all of Islamorada, offering an incredibly rare combination of breathtaking ocean views and expansive wide canal views. Encompassing over 32,000 square feet, this extraordinary property provides the perfect canvas for a custom waterfront residence designed to capture spectacular sunrises, refreshing ocean breezes, and the unmatched beauty of the Florida Keys. Its unique setting offers the best of both worlds--open water vistas in the front and a wide canal in the rear, creating an unparalleled lifestyle for boating enthusiasts and those seeking privacy, space, and unforgettable scenery. Opportunities to acquire a property of this caliber have become increasingly scarce in Islamorada, where large vacant parcels are exceptionally limited. Whether you're envisioning a private family compound or a legacy waterfront estate, this one-of-a-kind offering represents a chance to create something truly extraordinary in one of the Florida Keys' most desirable destinations.

74900 Overseas Hwy, Islamorada

$1,595,000

620208 MLS

DIRECT OCEANFRONT LOT IN ISLAMORADA WITH ACTIVE BUILDING PERMIT! A rare opportunity to own a beautifully situated direct oceanfront parcel in the heart of Islamorada, offering breathtaking panoramic views of the Atlantic Ocean. An active building permit is already in place, allowing you to begin construction of your dream waterfront estate immediately, or take advantage of the Village of Islamorada's available two-year permit extension. This spacious homesite includes a mangrove height reduction permit, allowing the mangroves to be trimmed to six feet. Upon completion, the property will enjoy unobstructed ocean views at ground level, creating an exceptional setting for luxury coastal living. Enjoy direct ocean access with convenient nearby Florida Bay access via Snake Creek, as well as close proximity to dry-dock marina facilities. Potential exists for an observation deck and/or dock, further enhancing the property's appeal and maximizing the spectacular waterfront setting. The elevation rendering is conceptual and provided for illustrative purposes. Utilize the approved plans currently in place or modify them to create a custom residence tailored to your vision. Opportunities like this are increasingly rare--build your dream home and experience the unparalleled beauty, boating, fishing, and island lifestyle that make the Florida Keys so desirable.

229 Coral Rd, Islamorada

$995,000

619655 MLS

Potential Short sale!!!Waterfront commercial investment opportunity with 100 feet of dockage on a 13,500 sq ft lot, offering both canal frontage and open ocean views--an increasingly scarce combination in the Upper Keys. Ideally located just outside Port Antigua and White Marlin Beach, the property benefits from strong visibility and proximity to established boating and residential communities. The site features convenient eastbound ingress and egress, supporting efficient operations and customer access. Zoned Commercial Fishing, it allows for a diverse range of income-producing uses, including charter services, boat rentals, marine repair, seafood distribution, restaurant or other waterfront commercial ventures. With direct water access, substantial dockage, and flexible zoning, this parcel is well-positioned for long-term appreciation and immediate revenue potential in a supply-constrained coastal market.

74520 Overseas Hwy, 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

$4,499,500

618920 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 for a 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. 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 remarkable bayfront estate offers endless possibilities in an unparalleled setting.

150 List St, Islamorada

$6,750,000

607307 MLS

OCEANFRONT ACREAGE IN HEART OF ISLAMORADA! Discover a unique opportunity to own oceanfront acreage right in the heart of Islamorada, the jewel of the Florida Keys. This remarkable property encompasses over 7 acres of pristine upland, complemented by baybottom, and comes with a coveted building right, allowing you to create your dream estate. With an astonishing 700 feet of direct Atlantic beachfront, your oasis in paradise awaits. Nestled in the vibrant community of Upper Matecumbe Key, you have the canvas to craft your vision, with space for your main residence, a caretaker cottage, a detached guest house, a tennis court, and even a charming boardwalk leading to your very own private sandy beach. Not only does this piece of paradise offer unparalleled beauty and space, but it also boasts zoning that allows for weekly rental potential, making it a valuable investment. Seize the opportunity to make your waterfront dreams a reality in the Florida Keys. This is your chance to create a legacy estate that combines coastal luxury with the convenience of town living. Don't miss out on this once-in-a-lifetime opportunity!

82900 Old Hwy, Islamorada

$2,000,000

615938 MLS

Beautiful 100' wide oceanfront lot on Lower Matecumbe Key, Village of Islamorada. Includes bay bottom and TDR so you do not have to wait in line to start your dream home. 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. Note: One of the owners is a State of Florida Real Estate Licensee

Overseas Hwy, Islamorada

$825,000

616719 MLS

This exceptional canal-front vacant lot on Lower Matecumbe Key represents a truly prime piece of cleared real estate. The permit for this property is in hand and ready for building. Seize this rare opportunity to build your dream home in a highly sought-after Keys location.

149 Iroquois Dr, Islamorada

$1,075,000

617028 MLS

ACTIVE BUILDING AND DOCK PERMITS. START BUILDING TODAY! Your tropical dream awaits with the lowest-priced waterfront lot featuring an active building permit in Islamorada. Imagine waking up to sunlit mornings, salty breezes, and the soft embrace of warm sand beneath your feet. Welcome to White Marlin Beach, where your vision of paradise comes to life. Vacant lots with active building permits are a rare find, and this one is ready for you to create your dream retreat. Picture a three-bedroom, four-bathroom island escape blending coastal charm with modern luxury. Two spacious, sunlit stories are designed for relaxation, complete with an elevator to ensure comfort and convenience. Expansive porches invite you to unwind, sip your morning coffee with bay views, feel the ocean breeze in your hair, and enjoy evenings under a canopy of stars. New construction offers more than a fresh startâ€''it brings favorable insurance rates, a solid foundation, and the confidence of quality craftsmanship. This is your gateway to maritime bliss. The private homeowners' park features one of the few sandy beaches in the Keys, perfect for building sandcastles, watching sunsets, and creating cherished memories. This property offers convenient access to vibrant dining, boutique shopping, and an inspiring arts scene. It's more than just a property; it's an invitation to embrace the island lifestyle. Opportunities like this don't wait. Ready to turn your dream into reality? Dive into your future at White Marlin Beachâ€''your tropical oasis is calling!

142 Gulfview Dr, Islamorada

$6,500,000

611386 MLS

Once in a lifetime investment in the heart of Islamorada. This exceptional property offers a wide range of potential uses as it includes two Village Center parcels stretching from Highway to Bay, currently featuring a spacious 3,995 sqft restaurant and bar with a coveted 5COP liquor license - no food quota. Village Center zoning allows for multiple use opportunities including, but not limited to, single family estate, multi family compound, luxury townhomes, vacation rentals, restaurants, marinas, general store with package sales, and much more. The property spans 30,415 sqft. Includes a Bayfront boat basin, and plans for an additional 100' dock to be constructed. The Village of Islamorada officially recognizes three waterfront market-rate dwelling units . The three waterfront Transferable Development Rights (TDRs) can be utilized onsite, transferred to another location, or sold to a receiver site. The Village Center Zoning would allow up to 8 market-rate dwelling units to be developed on site for a new luxury townhome community, with the transfer in of additional TDRs. Whether you're looking to rehab a local iconic business, start a new business, redevelop the entire site, or create a spectacular residential estate, this unicorn property is perfectly located. ***Buyer to verify ALL information.***

81910 & 81908 Overseas Hwy, Islamorada

$5,999,000

608979 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

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