Islamorada FL Waterfront Real Estate, Homes, Condos for Sale

3 Beds ⋅ 3 Baths ⋅ 619364 MLS

Welcome to effortless coastal living in the desirable Executive Bay Club community--where comfort, style, and resort-style amenities come together in a relaxed Keys setting. This nicely updated 3-bedroom plus loft townhouse offers a spacious and versatile layout designed for easy everyday living and entertaining. Upstairs, you'll find three inviting bedrooms, two full baths, and a charming loft--perfect for additional guests, a home office, or a cozy retreat. Downstairs, thoughtful updates create a seamless flow, with a level floor plan that connects the living and dining areas--no step-down interruptions--enhancing both function and openness. The expanded kitchen is a standout feature, showcasing stainless steel appliances, generous counter space, and a peninsula with double-sided storage, ideal for both cooking and gathering with friends and family. A full bath on the main level adds convenience for guests. Beyond your front door, Executive Bay Club offers an array of amenities to complement the coastal lifestyle. Enjoy two tennis and pickleball courts, newly expanded first-come, first-serve dockage for your boating adventures, and a beautifully renovated pool area complete with updated pool deck and bath facilities. The refreshed clubhouse provides an inviting space to relax and connect with neighbors. Whether you're seeking a full-time residence or a weekend escape, this welcoming townhouse delivers the perfect blend of elegance, comfort, and laid-back island living.

87200 Overseas Hwy Unit S3, Islamorada

$1,599,000

4 Beds ⋅ 3 Baths ⋅ 619331 MLS

Island Living in Prestigious Venetian Shores! Welcome to this newly custom-built 4bd/3ba residence ideally positioned on a tranquil plugged canal in one of the most sought-after subdivisions in the Florida Keys. Upstairs, enjoy a spacious open porch that flows seamlessly into a light-filled open concept floor plan. The designer kitchen features solid wood cabinetry, quartz countertops, a large island with waterfall edges, and accent-colored cabinetry for a modern coastal touch. The lower level offers the perfect guest quarters, complete with a private bedroom overlooking the pool, a large bathroom, and a generous living space. Concrete construction with metal roof and impact windows and doors allows you to enjoy the benefits of newer construction. Outdoor entertaining is a breeze with multiple seating areas and a large gazebo, and paver driveway that extends into a beautifully designed pool area. The concrete pool includes a water feature and LED lighting. Additional features include tall covered parking suitable for RVs and boats, and spray foam Icynene insulation in the attic for energy efficiency and reduced cooling costs. Buyers of new hones like this one can save an average of $25,335 over the first 10 years in lower utility bills and reduced repair costs compared to 20 year old homes - Based on recent study, Realtor.com. Boaters will love the nearby Venetian Shores marina with available boat slip rentals and convenient nearby access to boat ramps at Founders Park which also offers a sandy beach, pool, dog park and sports fields. Whether you're looking for a full-time residence or a weekend escape, this exceptional home captures the best of Florida Keys living! SELLER WILL PAY FOR A YEAR OF STORAGE FOR UP TO A 30' BOAT AT SNAKE CREEK MARIN

124 Venetian Way, Islamorada

$665,000

2 Beds ⋅ 2 Baths ⋅ 619328 MLS

This island resort style unit offers stations for dockage up to 25-foot boats, trailer storage and boat ramp. There is a pool for the development, pickle ball and tennis courts. The unit has hurricane impact windows as well as updated balcony area. It offers a large garage area with plenty of storage space.

118 Cortez Dr Unit B2, Islamorada

$1,695,000

3 Beds ⋅ 2 Baths ⋅ 619311 MLS

Desirable Venetian Shores 3 bedroom / 2 bath home just steps to your boat slip! Enjoy a direct sight line view of your boat and surround yourself with peaceful water views from almost every window of this bright, open-concept residence on one of the neighborhood's premier streets. This home offers the truly rare treat of wrap-around views of coastal living with a wide panorama of the private community marina and direct view of your assigned boat slip, plus water views of the closed canal in back. Don't miss this opportunity to live in Islamorada's most desirable neighborhood and enjoy the best boating in the Keys! With just minutes from your boat slip to Florida Bay and easy ocean access through Snake Creek to the Atlantic Ocean, you can delight in fishing, diving, offshore sandbars and boating to more than a dozen nearby waterfront restaurants and bars. This stilt home, built on reinforced concrete pilings, has all the living space on one level upstairs including an open kitchen with newer appliances (2023), large pantry, great room with high ceilings and a sun porch. There are also three large bedrooms in a split plan all with ample closet space. This family home offers the security of a reinforced metal roof, outdoor cameras and an alarm system, and the front door and most of the windows have also been upgraded to impact glass. Downstairs are two carports with workshop, a central tackle/storage room, and a sizable back yard with a sunken outdoor kitchen area/patio for enjoying afternoon barbecues after a day on the water. The expansive front yard has low maintenance landscaping and offers lots of parking for family, friends and all your toys. Relax with your favorite beverage on your covered front porch for a perfect view of the famous Florida Keys sunsets over the marina every night. Marina includes power/water and allows a variety of boat lifts to suit your boat. Ready to enjoy the best Islamorada has to offer with your boat steps from your door? Call today!

113 San Juan Dr Unit & Boat Slip, Islamorada

$24,995,000

7 Beds ⋅ 11 Baths ⋅ 619281 MLS

Experience unparalleled oceanfront living at the Chateau on the Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly unforgettable. Completely reimagined and newly constructed in 2023, this residence showcases exceptional modern design, engineering, and craftsmanship. Set on just under 2 acres of pristine coastline, the property offers 19,784 SF of total living and entertaining space, including 10,182 SF under air. Inside, soaring ceilings and walls of glass create a seamless indoor-outdoor connection, filling the interiors with natural light and highlighting refined, couture-level finishes. Amenities include a fitness center, indoor basketball and pickleball court, a Baccarat-inspired grand ballroom, and a custom Glamour Suite. Outdoors, a mosaic pool and spa overlook the Atlantic Ocean, complemented by alfresco dining, a firepit lounge, and multiple terraces with sweeping coastal views. A 300 inch outdoor LED theater and rooftop terrace elevate the experience. A 100ft private dock provides direct ocean access. Approved plans include 6 additional suites, including 2 oceanfront residences, allowing expansion into a multi-structure compound. A rare legacy estate defined by privacy, scale, and presence

82719 Old 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

$1,075,000

2 Beds ⋅ 2 Baths ⋅ 619193 MLS

Experience the relaxed lifestyle of Islamorada at its finest, at Ocean Harbor Condominiums. This first-floor unit sits directly above its assigned covered parking space and is conveniently closest to the elevator for easy access. A private backyard staircase leads you straight to the pool, and the beach is just steps from your door. This home can serve as a personal retreat or monthly vacation rental, and offers the perfect mix of comfort, convenience, and coastal charm. Inside, the spacious 2 bed/ 2-bath split floor plan offers 1,536 square feet of thoughtfully designed living space, providing privacy for guests, family, or friends. The primary suite features unobstructed ocean views, allowing you to wake up to the beauty of the sea each morning. The living room shares these sweeping vistas, perfect for tranquil sunrises. Enjoy your morning coffee on the porch or take a short walk to the Tiki Hut at the point, which offers ample entertainment space complete with barbecue grills and ice makers ideal for gatherings. Ocean Harbor is a gated community known for its extremely well maintained grounds, with meticulously raked beaches, freshly cut grass, and lush tropical landscaping. Resort style amenities include a large pool and jacuzzi, tennis courts, and a jetty with a Tiki Hut offering breathtaking, unobstructed ocean views. The beautifully appointed clubhouse features a gym, co-working space, and lounge areas. Outdoor grills are located throughout the beach area and near the clubhouse for casual entertaining. For boating enthusiasts, there's a boat launch for trailers, on-site boat storage, and slips available for rent for long term, which just might be cheaper than owning one and paying property taxes on the slip you own. Additional conveniences include electric vehicle charging stations, a pet-friendly policy allowing up to two pets of any size, and one assigned covered parking space. Call today for your private showing!

87851 Old Hwy Unit M3, Islamorada

$3,800,000

4 Beds ⋅ 5 Baths ⋅ 619187 MLS

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 15, Islamorada

$4,000,000

4 Beds ⋅ 5 Baths ⋅ 619186 MLS

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 8, Islamorada

$4,000,000

4 Beds ⋅ 5 Baths ⋅ 619185 MLS

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open, airy, and light-filled design. Residences are being offered fully furnished and amenities include open-concept kitchen, dining, and living spaces, powder room, ample closets, two oceanfront balconies, laundry room, 8 ft interior doors, and a 2-car garage with electric charging and added storage. The Beach Club delivers a luxurious experience with its pristine 600ft beach, private boat basin with ample dockage, two oceanfront pools, an oceanfront bar, fitness center, playgrounds for the kids, pickleball courts, unique driving range that extends into the ocean, plus a plethora of water activities allowing guests to fully immerse themselves in the Keys lifestyle. The privacy and exclusivity of this community set itself apart as a gated secluded beach destination environment surrounded by lush, mature landscaping that allows for either full time residency or effortless multigenerational vacations complete with and attentive staff. Open model unit available to show anytime. Some interior photos are from comparable villas within the property and not exact villa listed.

82779 Old Hwy Unit 7, Islamorada

$4,445,000

8 Beds ⋅ 4 Baths ⋅ 619083 MLS

Venetian Shores, the premier waterfront community in Islamorada!!! Looking for that larger than life home, well this is it! We have an 8 bedroom, 4 baths a pool, with nearly 5,000 sq. ft. of living area. Quick access to the Atlantic Ocean and Florida Bay with in minutes via Snake Creek. What makes this location unique is the 100 foot wide, deep water canals and what make this property more unique and valuable than others, we offer 100 linear feet of dockage. There is a 30,000 pound lift for your large boats and a 10,000 lift for your smaller boats. And there is still room for another vessel or personal water crafts. This home offers three levels, the main level has three bedrooms a full bath a kitchenette and living area with great views of the water. The second level, large living area with soaring ceilings, a massive kitchen, 2 bedrooms and a full bath. The third level offers 3 bedrooms and 2 full baths. There is an abundant pool and bar area for entertaining family and friends. Looking for a home to accommodate the large extended family, this is it or put it out in the Airbnb world, it would make a great income property.

136 San Remo Dr, Islamorada

$3,999,999

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

$4,500,000

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

$4,900,000

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 submitted 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

$4,900,000

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 submitted 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

$15,990,000

6 Beds ⋅ 9 Baths ⋅ 618911 MLS

Newly completed in 2025, this exceptional oceanfront estate is located in the heart of The Florida Keys on the premier ocean side of Islamorada. A gated entry welcomes you through lush tropical landscaping and a diverse fruit-tree grove, setting a private and refined arrival. Set on over 2 usable acres with 210 feet of private sandy beachfront and a protected cove, the residence spans 7,590 square feet of interior living space & 1,736 square feet of exterior living, with an expansive 230-foot dock. Designed for seamless indoor-outdoor living, the home features a dramatic great room with 23-foot ceilings, panoramic Atlantic exposure, and expansive covered terraces with summer kitchen and outdoor dining areas. A 65-foot heated lagoon-style pool with swim-up bar and fire-pit lounge creates a resort-caliber setting. The chef's kitchen is appointed with Sub-Zero, Wolf, and Thermador appliances. Additional highlights include dual primary suites, private orchid garden, lounge & recreation room, elevator, Sonos surround sound, impact windows and doors, metal roof, double-height garage, water-sports storage room and a full home generator. The essence of beachfront living in Islamorada, combining impressive scale and ultimate privacy. ***A contiguous 0.7-acre lot with development rights for an ancillary building with upstairs storage is available separately.

88351 Old Hwy, Islamorada

$4,645,000

618904 MLS

Experience breathtaking sunsets throughout the year on this waterfront lot ready for construction in Islamorada. There's no enduring lengthy waiting periods for development - this parcel comes with an active permit and holds a Residential Estate zoning designation. Encompassing a generous expanse from the highway to the bay, the property boasts an impressive 1.2 acres of land plus another .24 acres of bay bottom, accommodating deep-water dockage and a picturesque sandy beach. Seize the opportunity to actualize your ideal residence right now!

75750 Overseas Hwy, Islamorada

$775,000

2 Beds ⋅ 2 Baths ⋅ 618895 MLS

The first thing you notice as you walk up to this home is the view, bright blue ocean over green treetops. Step inside and it opens up even more: ocean, sky, and a wide lagoon with a sandy beach below. Sunset here is stunning. This very spacious 2 bedroom, 2 bath end-unit condo offers 1,330 square feet of single-level living with windows on three sides! Located on the second floor, above covered parking, it's that just-right height that makes all the difference. High enough for the views and breezes, without feeling disconnected. Access is easy by elevator or stairs. The oversized screened porch takes full advantage of the ocean and lagoon views and truly extends your living space. Inside, the home has been thoughtfully upgraded for both style and peace of mind. Gorgeous wood-plank tile flows seamlessly throughout the entire condo, including the expansive screened porch, creating a clean coastal look with easy maintenance. The bright kitchen features quartz countertops and stainless appliances - fresh, modern, and functional. Bathrooms have been tastefully updated, the electrical system has been upgraded, and hurricane impact windows and doors provide security and efficiency. Patio surrounded by smoothly operating accordion shutters. A tankless hot water heater adds to the home's smart improvements. You'll also appreciate the recently expanded storage closets and pantry space - something you don't always find in condo living. The community is shady, green, and peaceful. Amenities include a full-service marina (yes, even fuel) with long-term dockage available, waterfront pool, clubhouse, tennis and pickleball courts - soon to be lit for night play. Pets are welcome here. Coral Harbour Club is just five minutes from Founders Park, with its bay front beach, sports programs, dog park, and year-round community events. An updated, move-in ready condo with real ocean views, boating access, and one of the best locations in the Upper Keys. This one is worth seeing in person!

88181 Old Hwy Unit F24, Islamorada

$3,995,000

5 Beds ⋅ 3 Baths ⋅ 618653 MLS

Waterfront pool home with dockage in Venetian Shores offered furnished. Experience the ultimate Florida Keys lifestyle in this beautifully updated canal-front residence designed for relaxed coastal living and effortless entertaining. The home offers 5 bedrooms and 3 bathrooms, with approximately 2,640 square feet of living space, including 3 bedrooms and 2 bathrooms upstairs totaling approximately 1,500 square feet, and 2 bedrooms and 1 bathroom downstairs totaling approximately 1,140 square feet. The private resort-style backyard features a heated pool with sun shelf, hot tub, expansive patio, hammock lounge, and mature palms creating a true tropical setting. Enjoy deep-water canal frontage with 70 feet of dockage and two boat lifts rated at approximately 15,000 pounds and 20,000 pounds, providing exceptional boating capacity. Located on one of Venetian Shores' desirable 100-foot-wide canals, the property offers generous maneuvering space and convenient access to both the Atlantic Ocean and Florida Bay through nearby Snake Creek, making offshore fishing and backcountry boating easily accessible within minutes. The custom tiki pavilion includes a full outdoor kitchen with built-in grill, refrigeration, sink, bar seating, mounted TV, and generous space for hosting gatherings year-round. Inside, the bright open-concept living area showcases vaulted ceilings with exposed beams, abundant natural light, and French doors that create seamless indoor-outdoor flow to the balcony overlooking the canal. The primary suite offers balcony access, dual vanities, soaking tub, glass-enclosed shower, and walk-in closet. A gated brick driveway provides generous parking, and the home is offered furnished for immediate enjoyment or continued use as a full-time residence, seasonal escape, or investment opportunity. This Venetian Shores waterfront property delivers the location, spacious layout, wide canal setting, and boating infrastructure buyers are searching for in the Florida Keys.

105 Palo De Oro Dr, 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

$3,800,000

5 Beds ⋅ 3 Baths ⋅ 618165 MLS

Tired of waiting on Uber or Freebee? Why not make this stunning bayfront estate your own private slice of paradise, right in the heart of Islamorada? Just a flip-flop stroll away from local favorites like MEAT Eatery, Shima, Marker 88, and City Hall Café, this property places you at the vibrant core of island living. Behind its private, fully fenced grounds, you'll discover sweeping bay views and a rare tiki hut at the end of the dock—your new go-to spot for toasting unforgettable sunsets. Upstairs, the open-concept living area spills out through sliding glass doors onto a spacious, screened-in terrace, perfect for laid-back evenings or lively gatherings. This level also features three bedrooms and two baths, providing plenty of space for guests or family. Step down from the terrace to your own tropical oasis, complete with a pool, backyard, beach, and dock. The ground floor adds even more flexibility with two additional bedrooms, a bath, and a relaxed living area—ideal for guests or extended family. Whether you're looking for your forever getaway in the Keys or a smart investment when you're not soaking it all in yourself, this property is a rare find. Come see why life really is better by the bay.

87950 Overseas Hwy, Islamorada

$4,999,900

4 Beds ⋅ 4 Baths ⋅ 614893 MLS

Enjoy endless ocean views and direct access to the white sandy beaches of Islamorada from this oceanfront retreat. Behind your own private gated entrance, this solid concrete block home offers four bedrooms, four full bathrooms, and a bonus space. Inside, hardwood floors run throughout an open layout featuring a breakfast nook, dining bar, and spacious living area -- ideal for entertaining. The chef's kitchen is equipped with stainless steel appliances, a gas stove, and modern finishes. The master suite includes a private balcony overlooking the updated saltwater pool and a jetted tub for ultimate relaxation. This one-of-a-kind property also allows weekly rentals, making it a strong investment in one of the Keys' most sought-after locations.

75761 Overseas Hwy, Islamorada

$18,000,000

2 Baths ⋅ 613627 MLS

''The Pulse of Islamorada'' ... Iconic Islamorada Restaurant & Cabana Bar available for Sale, Real Estate and Business included. Spanning over 1,000 feet of bayfront and 500 ft of Highway frontage, where the locals & visitors come from near & far to watch nightly sunsets over the bay, enjoy food & libations, and listen to live bands daily. This property includes over 5 acres of real estate (survey available), full service bar with 5 Cop liquor license, 250 seat outdoor restaurant, private party & tournament hosting area. New parking lot, lighting, & drainage completed in 2020 with plenty of parking to expand the business. Concrete building built in 2015/2016 for gift shop, bathrooms, laundry, prep kitchen, storage, and more. In addition, property includes main kitchen, special event tiki bar, dockage, beach, boat ramp, and more. Sale includes 4 on site building rights & 2 boat slips in the Islamorada Yacht Basin located adjacent to property. Room for expansion. Voted Best Sunset year after year. Additional information and financials available upon request. NDA and POF required. Contact Listing Agent . All information to be verified by Buyer/Buyer's Agent.

96 Madeira Rd, 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

$6,495,000

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

$29,500,000

6 Beds ⋅ 6 Baths ⋅ 618152 MLS

A once-in-a-lifetime opportunity to own one of South Florida's most iconic properties. Welcome to Tea Table Key, a breathtaking 15-acre private island estate, accessible by car or by boat, located just minutes from downtown Islamorada and directly across from the famous Alligator Reef Lighthouse. Surrounded by vivid turquoise waters, this extraordinary sanctuary offers complete privacy and a front-row seat to nature's daily spectacle -- herons and egrets gliding overhead, pelicans diving at sunrise, and eagles soaring above your shoreline. Enjoy the rare luxury of total seclusion without sacrificing convenience. Within minutes, you're immersed in Islamorada's finest restaurants, art galleries, and shopping, yet at home you're embraced by the stillness of your own island world. Conveniently located approximately 1 hour and 30 minutes from Miami International Airport, or a 25-minute helicopter or seaplane ride, Tea Table Key offers an unmatched combination of accessibility and exclusivity. The island features a beautifully updated 6-bedroom residence, along with a tennis court and private dockage. Whether you choose to enjoy the comfort of the existing home or envision an entirely new luxury residence, Tea Table Key presents a truly incomparable canvas in one of the most sought-after destinations in the Florida Keys.

79775 Overseas Hwy, 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. 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

$4,750,000

5 Beds ⋅ 5 Baths ⋅ 615676 MLS

Experience elevated coastal living in this elegant Port Antigua retreat. Thoughtfully designed for comfort, privacy, effortless entertaining and situated in a prime waterfront location, this beautiful resort-style residence offers generous living spaces, including both upstairs and downstairs primary suites, three additional guest suites, a dedicated office, shaded porches on both levels and a spacious garage for ultimate flexibility. The gourmet kitchen flows seamlessly to a fully equipped outdoor kitchen and shaded lounge area--ideal for al fresco dining by the pool amid lush tropical landscaping. A rare combination of classic design, modern amenities, and timeless island charm. Effortless boating and space for all of your waterfront toys with 75' of deepwater dockage and quick access to both ocean and bay. Nearby homeowner's park provides the added bonuses of a private, sandy beach and boat ramp. With the serene, wide canal views and cooling bay breezes, and this is where luxury, comfort, and natural beauty, convenience converge.

88 W Plaza Del Lago, Islamorada

$6,900,000

3 Beds ⋅ 3 Baths ⋅ 616520 MLS

Welcome to Casa Mar Azul, a one-of-a-kind oceanfront estate located along the iconic Old Highway in Islamorada — a rare offering with 200 feet of oceanfront shoreline, a private jetty with dockage, and breathtaking panoramic views of the Atlantic Ocean. This elegant coastal retreat blends indoor-outdoor living with an open floor plan and soaring vaulted tongue-and-groove ceilings that bring warmth and character to the airy living space. Floor to ceiling windows and doors lead to an expansive open terrace, where unobstructed ocean views take center stage and sea breezes invite total relaxation. Upstairs, you'll find two spacious bedrooms and two full baths, each thoughtfully designed for comfort and ease. A versatile bonus room opens to a covered lanai that leads directly to your own sandy beach — the perfect spot for morning coffee or sunset gatherings. The private jetty stretches 200 feet into the turquoise waters and offers dockage at the end, ideal for boating, fishing, or simply soaking in the serenity of the sea. Nestled within mature tropical landscaping, this estate offers a sense of seclusion while being just steps or a short bike ride from Islamorada's best — charming restaurants, local boutiques, and vibrant art galleries. Whether you're looking for a serene island escape or a place to entertain in style, this exceptional property captures the spirit of the Florida Keys with timeless charm and coastal elegance. Offered by appointment only — your piece of paradise awaits.

82749 Old Hwy, Islamorada

$2,075,000

2 Beds ⋅ 2 Baths ⋅ 618666 MLS

What does everyone dream of? The smallest house in the best neighborhood -- and this one delivers. Welcome to easy, breezy living in Port Antigua, where charm, quality, and location come together beautifully. This thoughtfully updated home is being offered fully furnished -- from stylish pieces down to kitchen wares, dishes, and linens -- making your transition to the Keys seamless. Just bring your flip-flops. Impact windows and doors are installed throughout, including three skylights set into the concrete roof, so you can relax knowing your investment is well protected while natural light pours in from above. Upstairs, the open-concept living space feels airy and inviting, perfectly suited for gathering with friends and family. Triple sliding glass doors lead to a spacious second-floor terrace, creating that effortless indoor-outdoor flow we all love about coastal living. A separate laundry room just off the kitchen adds everyday convenience without sacrificing style. Both bedrooms feature their own sliding glass doors to the terrace, welcoming in sunshine and soft island breezes -- a gentle reminder that you're living somewhere special. Downstairs, you'll find abundant storage space and a 70-foot concrete dock complete with a fish-cleaning station and boat lift -- ready for offshore adventures or sunset cruises at a moment's notice. The yard is designed for low-maintenance enjoyment, with river rock and a clean concrete driveway in front, and artificial turf in the back for a lush look without the upkeep. This is the one you've been waiting for -- refined yet relaxed, polished yet playful. A perfectly sized slice of paradise in one of the Keys' most desirable neighborhoods.

121 Lisbon Ct, Islamorada

$2,790,000

3 Beds ⋅ 2 Baths ⋅ 617520 MLS

Beach life simplicity perfectly describes this pristine 3 bedroom, 2 bath oceanfront home with pool, covered patio, and gated for privacy. Stunning beach and ocean views are enjoyed from upper porch, lower level covered patio, living room and 2 of the 3 bedrooms. Fully remodeled in 2021, this charming get-away has been entirely refreshed with new everything...including impact windows and doors, metal roof, flooring, new appliances, central air, pool equipment and electric gate. Furnishings and finishes reflect the coastal cottage style creating the epitome of relaxation and embodying the Florida Keys lifestyle.

75055 Overseas Hwy, Islamorada

$4,700,000

4 Beds ⋅ 4 Baths ⋅ 617501 MLS

Welcome to 166 Bayview Drive, a rare bayfront estate in the prestigious Safety Harbor neighborhood of Lower Matecumbe Key. Located at Mile Marker 74, this property offers direct access to Florida Bay and the Atlantic Ocean, placing you in the heart of Islamorada's world-class boating and sportfishing scene. The home enjoys unobstructed water views and nightly sunsets that paint the sky in brilliant hues. A Tiki at the water's edge provides a perfect perch for morning coffee or evening cocktails, while mature landscaping adds privacy and tropical charm. Boaters will appreciate the deep-water dockage with davits, ideal for quick access to open water. The 2,478-square-foot residence features 4 bedrooms and 4 bathrooms, with tile flooring throughout and expansive windows that frame the bay. The open-concept living and dining areas flow into a well-appointed kitchen. The primary suite offers direct water views and private outdoor access. Outdoor living is elevated with a spacious pool and deck area, balcony, and brick paver walkways. The white picket fencing and lush landscaping complete the coastal aesthetic. Additional features include CBS construction, off-street parking, FKAA water service, septic system, and low HOA fees. Pets are welcome. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, 166 Bayview Drive delivers unmatched location, views, and lifestyle in the Florida Keys.

166 Bayview Dr, 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

$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

$999,000

2 Beds ⋅ 2 Baths ⋅ 618847 MLS

Beautiful Atlantic Ocean views surround this newer concrete home featuring an open-concept floor plan with 2 bedrooms and 2 bathrooms. Tastefully furnished with a coastal flair, the spacious living area flows into a kitchen appointed with custom wood cabinetry, quartz countertops, stainless steel appliances, and a high-end water filtration system. Impact windows and doors, plantation shutters, new A/C, and new gutters add to the home's quality. A true boater's dream, the property offers direct ocean access and convenient Florida Bay access via Snake Creek. Take in breathtaking sunrises and sunsets from your own slice of paradise. Whether you're seeking a full-time residence or the ultimate Florida Keys retreat, this home delivers the best of the Keys lifestyle. YOU OWN THE LAND!

84961 Old Hwy Unit 18, Islamorada

$459,000

2 Beds ⋅ 2 Baths ⋅ 618199 MLS

🌊 Spectacular Direct Ocean Views! ✨ Islamorada's Best-Kept Secret! This beautifully appointed 2-bedroom, 2-bath residence offers breathtaking, unobstructed ocean views from your private waterfront balcony. Step outside and enjoy a refreshing swim in the oceanfront pool or take a dip directly in the crystal-clear Atlantic. Perfectly situated near Bud & Mary's Marina and just minutes from Islamorada's most beloved restaurants, this location captures the very best of island living. This property is truly a must-see--and it's priced to sell. Seller will consider all reasonable offers.

79901 Overseas Highway Unit 204, Islamorada

$3,495,000

4 Beds ⋅ 5 Baths ⋅ 616523 MLS

Welcome to Your Florida Keys retreat or income-producing rental, with 7-day rentals approved! Maison Residences presents its final developer unit, #201, offering 4 bedrooms, 4.5 bathrooms and a spacious open layout designed for true oceanside living. Step off your private elevator into a grand room with soaring 10-foot ceilings and 9-foot stacked sliders that frame endless Ocean views. The open plan connects casual dining, island seating, and a gourmet kitchen outfitted with Sub-Zero and Wolf appliances, Caesar-stone counters, and abundant storage. Oversized covered terrace expand your living space outdoors, where multiple seating areas, TV, a fireplace, and an infrared/gas grill create the ultimate setting for entertaining against the ocean backdrop. The master suite features king-sized accommodations, terrace access, and a spa-inspired ensuite with a luxurious tub and glass shower. Three additional guest suites, 2 with king beds and private balconies, 1 with two twin beds and all with en-suite baths that provide comfort and privacy. This exclusive enclave sits between the Atlantic Ocean and Florida Bay on Islamorada's most vibrant island, Upper Matecumbe Key. Maison's private grounds include over 350 feet of natural sand beach, a 155-foot day pier, lavish 86-foot lagoon-style pool, heated jacuzzi, and space for every water activity. Details such as porcelain tile, U-Line beverage center, Lynx grill, Kohler fixtures, built-in closets, and energy-efficient construction reflect luxury and comfort at every turn. Owning at Maison Residences gives you the rare flexibility to enjoy your home while also generating income. With 7-day minimum rentals approved, you can use your residence as a private retreat and still take advantage of strong demand for luxury short-term stays in Islamorada. This makes Unit 201 not only a lifestyle purchase with world-class boating, fishing, diving, and snorkeling, but also a smart investment opportunity!

80639 Old Hwy Unit 201, Islamorada

$10,900,000

6 Beds ⋅ 5 Baths ⋅ 618449 MLS

A refined expression of waterfront living, this six-bedroom, four-bath residence is set on a desirable over ½ acre lot with panoramic water views from every room. Offering 220+ linear feet of concrete dockage with three boat lifts, the property is exceptionally suited for large vessels with effortless access to the open Florida Bay/Gulf or Ocean via Channel 5 bridge. Two separate parcels included in this sale, opening options in the future for the fortunate owner that resides here. Completely renovated in 2020, the home presents a clean, contemporary aesthetic with Viking appliances, bespoke finishes, and a subtle, neutral palette inspired by the flowing surrounding turquoise waters. A custom saltwater pool equipped with both heater and chiller provides year-round enjoyment for everyone. This Safety Harbor residence delivers both elegance and function for the discerning boater or sunset lover. Impeccably maintained and move-in ready, it offers a rare combination of low-maintenance living, thoughtful design, quiet living and enduring appeal in the Florida Keys. Private showings available by appointment.

186 & 165 Bayview Dr, 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

$8,590,000

8 Beds ⋅ 10 Baths ⋅ 613653 MLS

Nestled in the exclusive Safety Harbor enclave of Islamorada, this stunning Gulfside estate offers an unparalleled blend of luxury and tranquility. Situated on a prime point, the property boasts breathtaking open water views and the added advantage of protected dockage, making it a boater's paradise. With a concrete seawall, two boat lifts equipped with power and water, and a fish cleaning station, this home is perfectly appointed for waterfront living. Easy ocean access through the nearby Channel 5 Bridge adds to its appeal for avid anglers and adventure seekers alike. Inside, the home features eight spacious bedrooms, each with its own ensuite bath, plus two additional half baths for convenience. The master suite is a private sanctuary with a spa-inspired bath, while the open layout showcases spectacular water views through impact windows and sliding glass doors. An elevator ensures effortless access to all levels, and the wraparound balcony invites you to savor unobstructed panoramas. The gourmet kitchen, complete with high-end stainless steel appliances and gas cooktop, is a chef's delight, complemented by an outdoor kitchen for alfresco entertaining. With its seamless indoor-outdoor design and unmatched location, this property is the epitome of luxurious Keys living. Owner/Agent

162 Bayview Dr, Islamorada

$11,000,000

4 Beds ⋅ 4 Baths ⋅ 616886 MLS

Commanding 170 feet of private Florida Bay frontage, and situated on over and acre of precious Islamorada land, Eagle Point is a contemporary coastal estate that captures the essence of refined waterfront living. Designed for both serenity and sophistication, the residence blends clean architectural lines with the natural beauty of its tropical surroundings. Gated and beautifully landscaped, the property opens to sweeping open-water vistas framed by swaying palms and fruit trees orchard upon your entrance. Expansive glass walls flood the interiors with natural light, connecting elegant living and dining spaces to the outdoors providing vast screened porched both upstairs and down. The kitchen anchors the home with gorgeous views and function ideal for entertaining or quiet evenings at home. A downstairs flex room and private gym add versatility and wellness to daily life, while multiple rooftop terraces invite sunset gatherings and panoramic bay views. Outside, the resort-inspired amenities continue with a lagoon-style pool, putting green, and ample deepwater dockage with boat lift with Bay to Ocean access in minutes via Channels 2 or 5, offering effortless access to world-class boating and fishing. Just off the edge of the channel lies a rare bayside reef teeming with life and providing snorkeling right off your own dock. Located on the Lower Matecumbe island of Islamorada, Eagle Point balances modern coastal luxury with timeless island tranquility—an estate designed for those who seek both beauty and belonging by the water.

75280 Overseas Hwy, Islamorada

$3,300,000

3 Beds ⋅ 3 Baths ⋅ 618699 MLS

74560 Overseas Highway is a dynamic waterfront commercial asset with multiple revenue paths and significant redevelopment potential. Situated on a 15,000 SF parcel with generous on-site parking and 100 feet of seawall capable of accommodating up to 8 slips, the property delivers premier highway exposure and immediate Florida Bay and Atlantic Ocean access. Zoning supports four affordable housing units, one market-rate residence, and 5,640 SF of commercial space, creating a layered income strategy that blends residential density with marine-oriented business activity. The existing structure features expansive wraparound windows framing sweeping Atlantic views, plus a top-floor penthouse suite suited for owner occupancy, executive housing, or premium rental use (subject to approvals). The building configuration can also accommodate a rooftop helipad. Commercial Fishing zoning allows for uses such as a destination restaurant, seafood market, marine outfitter, charter or backcountry fishing headquarters, marina-support retail, or other enterprises aligned with the working waterfront. This is a high-visibility, commercial platform where housing, marine access, and US-1 frontage intersect to create compelling long-term value.

74560 Overseas Hwy, Islamorada

$6,700,000

4 Beds ⋅ 5 Baths ⋅ 616619 MLS

Iconic Islamorada Oceanfront Retreat. Welcome to The Last Resort, a one-of-a-kind oceanfront estate offering rare privacy and breathtaking natural beauty in the heart of Islamorada. Set on over an acre of lush tropical land, this coastal retreat boasts 165 feet of private sandy Atlantic beach, where you can launch a kayak or paddleboard right from your backyard and soak in endless turquoise views. Expansive covered verandahs, a 15' x 30' heated seaside pool, and beachside hammocks invite slow, sun-filled days and relaxed gatherings. Across the street, a separate canalfront parcel with a 37.5' concrete dock provides protected deep-water dockage and space for boats, trailers, and water toys — an extraordinary pairing of true beachfront living and convenient boating access. Inside, the home's 3,860 square feet is designed for easy Keys living with generous main-level living areas and bedrooms, plus a spacious upstairs suite with private bath and roof-top deck capturing panoramic ocean vistas. Four bedrooms and five baths accommodate family and guests comfortably, while breezy porches and open gathering spaces make entertaining effortless. Highlights you'll love: 165' of private sandy Atlantic beach with direct ocean entry, 37.5' private concrete dock on canalfront lot for boating convenience, 15' x 30' heated seaside swimming pool with expansive sun decks, over one acre of tropical privacy and mature landscaping, 4 bedrooms | 5 baths | 3,860 sq. ft. with thoughtful single-level layout plus upstairs suite and roof deck. A true Keys treasure, The Last Resort delivers a rare mix of sandy beach, deep-water dockage, and timeless coastal charm. Ann exceptional opportunity to create your own island legacy!

109 Columbus Dr, Islamorada

$2,495,000

3 Beds ⋅ 4 Baths ⋅ 617838 MLS

Perfectly positioned in the heart of Upper Matecumbe Key, this stunning residence places you in downtown Islamorada--just a short stroll to the area's most celebrated restaurants, art galleries, and island attractions. Privately gated and approached by a Chicago paver driveway, this absolutely turn-key 3-bedroom, 3.5-bath residence is part of an exclusive collection of just eight bayfront homes and was completed in 2020 with refined design, upscale finishes, all stainless-steel Bosch appliances, and exceptional craftsmanship throughout. Elegant interiors and thoughtful details create a sophisticated yet relaxed island lifestyle. The home features a private pool with a wood deck at the rear--ideal for entertaining or unwinding in complete privacy--while residents also enjoy access to a community bayfront pool overlooking breathtaking sunset views. An assigned boat slip on the bay provides effortless access to Florida Bay and the Atlantic beyond. Boat lift currently in place can hold boats up to 5,000Lbs. Adding to its appeal, 7-day rentals are permitted, making this property a rare and superior investment opportunity in one of Islamorada's most walkable and desirable locations. Ideal for a full-time residence, island getaway, or income-producing asset, this home offers an exceptional blend of luxury, lifestyle, and flexibility. Coral Cove is located in an X flood zone, providing additional peace of mind.

81906 Overseas Hwy Unit 2, Islamorada

$4,600,000

5 Beds ⋅ 6 Baths ⋅ 617341 MLS

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout. Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation. On the main floor, the gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock. This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

117 Leoni 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

$24,995,000

5 Beds ⋅ 8 Baths ⋅ 617705 MLS

Newly completed private oceanfront estate on 2+ acres in Plantation Key, offering an extraordinary combination of scale, privacy, dockage, and resort-style living in the heart of the Florida Keys. Designed for luxury coastal living, entertaining, and extended stays, this exceptional estate features over 9,000 sq. ft. of interior living space and more than 15,000 sq. ft. under roof. Set behind a gated entry, the residence offers 5 ensuite bedrooms, 5 full baths, 3 half baths, multiple flex spaces, an elevator, expansive covered porches, and seamless indoor-outdoor living. Additional luxury spaces include an in-home theater, private gym, and a massive office overlooking the ocean, all of which could easily serve as additional bedrooms, creating the potential for an 8-bedroom layout. The outdoor spaces are designed to showcase the Atlantic Ocean setting, with a resort-style pool, jacuzzi, generous lounging areas, and sweeping oceanfront views. Boaters will appreciate the 80-ft dock, 20,000 lb boat lift, and 160-ft jetty, creating outstanding access for enjoying the Keys lifestyle. With vacation rental zoning, the property also offers investment flexibility for those seeking personal use, income potential, or a legacy estate. Private oceanfront acreage of this scale is increasingly rare in the Upper Keys, making 87895 Old Hwy a standout opportunity for the buyer seeking a newly completed Florida Keys estate with privacy, presence, flexible living space, and exceptional waterfront amenities.

87895 Old Hwy, Islamorada

$750,000

3 Beds ⋅ 2 Baths ⋅ 613083 MLS

All NEW NEXT TO MARINA & POOL Stunning Islamorada 3 full bedrooms 2 brand new bathrooms plus oversized loft with additional queen and three twin beds. This Townhouse has ALL NEW kitchen, new bar, new built-ins, new custom fishing closet & storage, brand new 4 ton AC unit, 2 brand new Bathrooms with showers, new extended loft area, new full size Washer/Dryer, new BBQ area with new patio chicago brick pavers plus private patio shaded area with beautiful palms trees, serena & lily furniture inside, new electric panel, new electric water heater, new 80' smart OLED TV, new area just for refreshments, coffee and bar, new 4 ton AC unit, high end hurricane impact windows and doors that are reflective and cannot see inside. New Electric car charging electric panel exclusive to this unit. Best area in the community next to pool and marina with two pickleball courts and basketball court in the rear. Sleeps easily over 10 people. King bed in the master bedroom, 2 queen mattress in additional bedroom and loft along with 5 twin mattresses. Rented in winter for over $6,500 a month! Call today! This community features a new private beach, marina, dock and clubhouse. Being SOLD fully furnished and fully equipped with high end appliances (FRIGIDAIRE), high end furniture (SERENA & LILY) and furnishings. See 3 Videos: https://youtu.be/P8cOME8P_kY; https://youtu.be/b6RmPMU8pvk; https://youtube.com/shorts/BEo0F_YzVFE;

87200 Overseas Hwy Unit V9, Islamorada

$2,500,000

3 Beds ⋅ 3 Baths ⋅ 618461 MLS

Located in the highly desirable Venetian Shores neighborhood in Islamorada, this canal front home offers 70 feet of dockage with a brand new concrete dock and seawall, making it an excellent opportunity for boating enthusiasts. Enjoy quick and convenient access to both the Atlantic Ocean and Florida Bay through Snake Creek, one of the most sought-after boating access points in the Florida Keys. This prime location allows for easy navigation whether heading offshore or exploring the backcountry. Situated on a 7,000 square foot lot, the property features a two-bedroom, two-bathroom layout upstairs, along with a one-bedroom, one-bathroom downstairs, offering additional flexibility for guests, extended family, or bonus space. The home has been freshly painted and is ready for immediate enjoyment, while also presenting an opportunity to update, expand, or build new in a neighborhood known for redevelopment and custom homes. For boaters, this property is ready to go--complete with a new concrete dock and seawall, ideal for accommodating a large vessel. A boat lift permit has already been applied for and approved by the Village of Islamorada, providing added value and convenience for the next owner. Venetian Shores is known for its wide canals, excellent water access, and close proximity to dining, marinas, and local amenities. Whether you're looking for a primary residence, vacation home, or future investment, this property offers strong potential in one of Islamorada's most desirable waterfront communities.

109 Milano Dr, Islamorada

$18,999,000

6 Beds ⋅ 8 Baths ⋅ 615643 MLS

A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a protected deepwater basin. Designed for elevated living, The Oasis blends resort-style amenities with the privacy and scale of a true Florida Keys compound. The grand porte-cochère entry sets the tone, leading to a single-level main residence with soaring ceilings, white oak floors, and 12' retractable glass walls that frame sweeping ocean views. The chef's kitchen is anchored by a Calacatta marble island, Thermador appliances, and a walk-in pantry, opening to a spacious great room and dining area ideal for entertaining. The main home features four bedrooms, six full bathrooms, and a soundproof theater room. The primary suite is a private retreat with a fireplace, dual walk-in closets, a safe room, and a spa-inspired bath with a steam shower. Each additional bedroom includes an en suite bath, private balcony, and ocean views. A detached guest house offers two additional bedrooms and bathrooms, creating a total of six bedrooms across the estate with endless space for expansion. The summer kitchen, alfresco dining areas, and multiple lounging terraces offer seamless indoor-outdoor living. The deepwater basin accommodates larger vessels and provides quick access to the Atlantic and Bay. Amenities rival a private resort: soundproof theater, fitness center with sauna, golf simulator, and two resort-style pools—each with a spa, sun deck, and outdoor entertaining spaces. Discreetly luxurious and effortlessly livable, The Oasis redefines waterfront living in the Florida Keys. Designed for ultimate security and safety, this home was built to provide unmatched peace of mind. Every element was designed with meticulous attention to detail and an uncompromising commitment to quality. The Oasis is not just a residence—it is a lifestyle statement in one of the Florida Keys' most desirable locati

87429 Old Hwy, Islamorada

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