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Islamorada LUXURY Homes for Sale, Single Family Houses, Florida Keys Real Estate

Total Listings 109
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75900  Overseas Highway  For Sale, MLS 590677
$17,900,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
7 Bed, 7 Baths, 6,198 SqFt Days Listed: 33
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Welcome to your own private estate immersed on almost six acres in Islamorada with over 600 feet of glistening sandy beach. This magnificent estate sets a new standard of island living. Drive along your lush private driveway, past your tennis court and enter the foyer where you are greeted with views upon views of Florida Bay, beach sand and serenity. The Master Suite - perfectly situated on the first floor features an oversized sitting area, his and her walk-in closets, his and her bathrooms and an outdoor patio. Five additional en suite bedrooms plus a guesthouse with an additional 418 SqFt comprise 6,148 SqFt of ample living area. Custom features include Crema Marfil brushed stone floors, built-in cabinetry and Florida Keystone fireplaces. The chefs kitchen is an epicurean dream

79775  Overseas Highway  For Sale, MLS 585835
$15,000,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 374
-11.76% ($2,000,000) 1 Price Change : Last Change 241 Days Ago
Off Shore Isl - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits40ft.

An extremely rare and stunning private island, accessible by car, Terras Key is a gated Caribbean Island located at Mile Marker 79.7 in Islamorada. Jutting into the blue-green waters of the Atlantic Ocean, Terras Key features a 2,000+- driveway enabling you to reach restaurants and shopping easily.Enjoy the conveniences of the modern world, including all utilities, while surrounded with the privacy of your own +15.5 Acre Island with miles of open water views and views of Alligator Reef Light. The compound includes 5 bedrooms and 4 baths, pool, cabana, dockage, and a tennis court. This extraordinary private island is a landmark in Islamorada and the Florida Keys and has not been offered for sale for over 27 years.

139  Gimpy Gulch Drive  For Sale, MLS 582483
$8,900,000
Plantation Key
Misc Plantation Key   - MM: 85.00
6 Bed, 6 Baths, 6,573 SqFt Days Listed: 583
-6.27% ($595,000) 1 Price Change : Last Change 210 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

Opulent, alluring and meticulously detailed, this Islamorada Estate is where perfection meets the Bay ~ welcome to The Fish Ranch. Located on Plantation Key, The Fish Ranch estate features two (2) single family residences plus a media house, and cabana with outdoor kitchen. World-class designs make this one of the more distinguished estates for the most discriminating buyer. Elevator shaft, 100 swimming pool with two beach entries, hot tub, 250 of sandy beach, putting green, dockage, architectural designed landscaping with fire pit and lighting throughout. Also included with this property is an additional 19,729sf lot.

89707  Old Highway  For Sale, MLS 587281
$8,300,000
Plantation Key
Lake Harbor   - MM: 89.00
5 Bed, 5 Baths, 6,269 SqFt Days Listed: 265
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Lift,Davi

Welcome to Mima Grada... your Florida Keys oceanfront dream estate with everything you desire to live the ultimate island life. Enjoy your own private boat basin with boat lift and jet ski davits, sprawling sandy beach, lagoon-style pool/spa with poolside tiki bar, private lighted tennis court, and of course expansive ocean views. This spacious beach mansion stands out as one of the most elegant on Islamoradas Millionaires Row, which is an eclectic collection of unique open water estates all with distinctive entry gates, winding driveways and lush tropical foliage. Enjoy the serenity and privacy of Mima Grada with your immediate family or feel free to invite all your friends with plenty of room for entertaining both inside and out including two private guest suites. Must see!

75300  Overseas Highway  For Sale, MLS 586167
$7,950,000
Lower Matecumbe
Lower Mat Harbor   - MM: 75.00
4 Bed, 4 Baths, 4,610 SqFt Days Listed: 349
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp,

Sea Garden is located on an impressive landscaped 1.5 acre bayfront parcel sprinkled with orchids and boasts a highly unique bayside coral reef right behind the docks. This completely solar powered home has been built to last and offers over 120 of deep water dockage with 13k boat lift plus kayak/paddleboard ramp and floating dock. Three car garage with upstairs guest house is an added bonus to this already impeccable estate. Watch the bald eagles fly by, the painted sky sunsets and enjoy the natural surrounding beauty of the Florida Keys right from your back porch!

209 E Carroll Street  For Sale, MLS 590112
$7,900,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
8 Bed, 8 Baths, 4,931 SqFt Days Listed: 89
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

FairWinds~A unique two acre oceanfront estate, discretely situated in downtown Islamorada on Upper Matecumbe Key. FairWinds reflects elegance, beauty, seclusion, along with many amenities. Inside the gates are enchantingly lush tropical gardens with carefully cultivated native specimens leading to the shimmering pastel blues of the Atlantic ocean, which gently caresses the 250+ feet of secluded sandy beach. This very special compound blends privacy with abundant recreational opportunities, ideally suited to create cherished memories with family and friends. FairWinds offers a grand main house, complete with a wrap-around porch, wide verandas and stunning ocean views, perfect for memorable gatherings of family and friends. Watch the sun rise beyond the historic Alligator Reef Lighthouse

88663  Old Highway  For Sale, MLS 589040
$7,900,000
Plantation Key
Key Heights   - MM: 88.50
5 Bed, 5 Baths, 5,457 SqFt Days Listed: 145
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 100ft.Concrete

Expansive oceanfront family estate compound never before offered for sale! Known as Plantation House, this unique property was once the star of the Islamorada Tour of Homes and was featured for its 2.5+ acres of tropical gardens complete with numerous manicured foot paths lined with coral stones. As one of Islamoradas exclusive Millionaires Row properties, the homes entrance is privately gated and offers a winding paved driveway meandering through the trees and opening to reveal the 5,457 sf home with oceanfront pool, elevator, deep dockage, sandy beach, private boat ramp and endless ocean views. The permit has been approved to replace the damaged dock in its previous footprint, including the gazebo at the end. This one-of-a-kind property is ready to refresh and make your own!

200  Atlantic Street  For Sale, MLS 589035
$7,900,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
8 Bed, 8 Baths, 4,744 SqFt Days Listed: 145
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Introducing Bunny Key, an extraordinary historic Islamorada oceanfront plantation. Once you enter the gate you will be entranced by the prettiest beach on the island of Islamorada with an estimated 240 feet lining the Atlantic ocean and lovely new dock. The main home and guest wing of 3 bedrooms radiate character at every corner, reminiscent of a time gone by with the inviting Old Florida porch stepping out on to the beach. The Kitchen is lined in custom Pecky Cypress cabinets and stone counters which blends beautifully with the Dade County pine flooring throughout. There is a historic 3 bedroom guest home and a 2 bedroom caretakers cottage on the sprawling grounds each with beautiful verandas featuring ocean vistas. Detached garage and outdoor kitchen area can also be found.

158  Key Heights Drive  For Sale, MLS 588557
$7,900,000
Plantation Key
Key Heights   - MM: 88.50
5 Bed, 5 Baths, 6,183 SqFt Days Listed: 178
+6.84% ($506,000) 1 Price Change : Last Change 155 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Lift,Boat

Only the finest of materials, appliances, whole house systems and true attention to detail make up this custom-built bayfront estate which exemplifies all the best in quality home construction. Enjoy sweeping open water views and unequaled casual Keys living from the security and comfort of expansive spaces set with a classic understated design. Amenities include: Vaulted ceilings of Yellow Alaskan Cedar Spanish Limestone floors Large screen theater/media room Gym Grand master suite with private balcony Two guest suites Two den/office spaces (both can be utilized as addl bedrooms) Solid maple cabinetry Wolfe & Subzero Appliances Multi-head shower systems Mahogany interior doors Security system Anderson impact/insulated windows

88987  Old Highway  For Sale, MLS 587930
$6,995,000
Plantation Key
Trop Coral Reef   - MM: 89.00
6 Bed, 6 Baths, 5,839 SqFt Days Listed: 217
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Through a long winding and manicured driveway off of the Old Highway you will enter this exquisite Seaside Villa located on Plantation Key in Islamorada, FL. Sitting on 2 acres, this Atlantic Ocean facing property has 170 ft of shoreline with deep water dockage, boat lift and sandy beach, a rare find in the Florida Keys. Step up the imperial staircase into the breathtaking great room with commanding views overlooking the ocean featuring 5839 sq ft plus an additional 2387 sq ft on the ground floor for a total of 8,226 sq ft. of grand living space with 3 levels offering 6 bedrooms, 4 bathrooms, and 1 half bath with an additional 1 bedroom en suite, 1 full bath and 1 half bath on ground level. The distinctive features of this home consist of exquisite wood and marble floors, 8 high solid

86600  Overseas Highway  For Sale, MLS 587086
$6,495,000
Plantation Key
Misc Plantation Key   - MM: 85.00
5 Bed, 5 Baths, 10,000 SqFt Days Listed: 282
PreConstructi - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Start building your dream home or one of a kind trophy estate without the wait. Active permit in hand. A Village dock permit is assured in a recorded Village Council Meeting. Over 21 acres offering private access from US-1 to your estate and year round sunsets over a secluded pristine cove on one of the largest residential parcels available in the Keys. Fish for bonefish and tarpon along your private cove, or snook in your private creek or ponds within the property. Snorkel from your beach. Watch the manatees, dolphin and turtles frolic around the basin. A bird lovers paradise. Enjoy quick ocean and bay access via Snake Creek accommodating boats of almost any size. Like living on your own very private and secluded nature preserve. Perfect for a family compound or corporate retreat.

  South Drive  For Sale, MLS 585035
$6,300,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
5 Bed, 5 Baths, SqFt Days Listed: 426
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Other Dockage2

This is an incredible real estate land opportunity on the ocean side of Plantation Key known as Plantation Point South. This 9-acre, estate property boasts of approximately 750 feet of shoreline bordering a secluded, conservation parkland with a sandy beach. Build your new, custom home high atop terraced land, positioned to take full advantage of the propertys spectacular ocean views. The elevation of this building site allows for ground level construction making it the perfect setting for a family compound to pass down to future generations. Approximately 400 feet of sandy beach below offers an abundance of sky-high coconut palms with permit to add a pier leading to your very private oceanfront observation platform with a day bed.

80221  Overseas Highway  For Sale, MLS 588502
$5,700,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 81.20
4 Bed, 4 Baths, 3,195 SqFt Days Listed: 181
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

COCOMOS is a picturesque, and tropical, island retreat, on a beautiful 3-acre ocean-front estate, just a short walk away from the art district in Islamorada. This property is secluded with a private, electronically gated entry. Outdoor amenities include 250 of pristine sandy beach, pool with waterfall and ocean-front pool deck, outdoor shower, huge furnished Chickee with full summer kitchen, new dock, pond, great lawn and lush landscaping. The main house hosts 3 bedrooms and 3 baths with two living rooms and two kitchens. The guest house hosts 2 queen beds, a sleeper sofa, kitchen, bath and 2 ocean-front patios.

85289  Old Highway  For Sale, MLS 588920
$5,450,000
Windley Key
Galen Beach   - MM: 85.00
4 Bed, 4 Baths, 3,035 SqFt Days Listed: 151
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Basin,

Welcome to Blue Harbor! This property has been totally renovated and offers over an acre of land, 200ft of dockage, and a spectacular pool. Exceptional in every way, this home comes with an exclusive and private deep water boat basin along the Atlantic Ocean, something you will not find elsewhere! This spacious residence has four bedrooms and three bathrooms with an abundance of windows in every room and hurricane proof sliding glass doors for panoramic water views. This home has been designed so that you are able to effortlessly capture the ocean view from any vantage point, whether its from the front balcony, the stainless steel and glass lined staircase, or the luxurious master bedroom. This listing is complete with brand-new stainless-steel appliances and a state-of-the-art chefs gour

162  Key Heights Drive  For Sale, MLS 588621
$4,950,000
Plantation Key
Key Heights   - MM: 88.50
5 Bed, 5 Baths, 2,557 SqFt Days Listed: 174
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin,Boat Lift,Davi

Exclusive Bayfront Home in Islamorada. This extraordinary home is truly a tropical Keys paradise, surrounded by a spectacular protected boat basin. This fabulous home features custom handmade mahogany doors throughout, marble floors, expansive great room with gorgeous views of the bay, chefs gourmet kitchen, beautiful master suite with amazing custom bathroom and bay views, home theater room, custom pool with beach entry and waterfall, and a 90 foot concrete dock with boat lift and davits. Mature landscaping abounds, providing a lush tropical experience. The ultimate beach jetty offers privacy and world class sunset views. The ground level front entry elevation is at a remarkable 15 feet, making this one of the highest ground elevations in the Keys. Truly a unique oasis in Islamorada.

85261  Old Highway  For Sale, MLS 587825
$4,900,900
Windley Key
Unplatted Windley Key   - MM: 88.00
3 Bed, 3 Baths, 1,839 SqFt Days Listed: 224
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Ramp

MAGNIFICENT OCEANFRONT PARCEL WITH JUST UNDER 3 ACRES on Windley Key in Islamorada. This property boasts a huge, IRREPLACEABLE, DEEPWATER boat basin to house and protect many boats PLUS just over 500 Linear Feet direct Atlantic Ocean frontage. Ground Level home offers a fireplace and endless ocean views from the large deck. Catch the endless ocean breezes at the waterfront Tiki. Hut. A rare and unique opportunity.

88547  Old Highway  For Sale, MLS 576121
$4,500,000
Plantation Key
Key Heights   - MM: 88.50
4 Bed, 4 Baths, 4,103 SqFt Days Listed: 1065
+4.65% ($200,000) 6 Price Changes : Last Change 596 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Davits400f

Open Oceanfront Estate with Deep Dockage on 1.5 Acres on Millionaires Row... Islamoradas premier address. Brand new dock with two new boat lifts to enjoy the best boating in the Keys! Spacious 4,103 s.f. home with 4 bedrooms, 3 full baths, a large heated pool, winding private driveway, and a soaring central atrium surrounded by walls of windows to frame the ocean view. Open ocean views from the living room, Florida room, porches, master bedroom and upstairs loft. Living room with wet bar and pass-through window to the gourmet kitchen and separate dining room, all with Saturnia stone floors. Direct boating access to the best offshore fishing and diving, plus quick Florida Bay access. RE Zoning allows weekly rentals for income potential. Call today!

112 & 116  Buena Vista Court  For Sale, MLS 590270
$4,499,999
Lower Matecumbe
Port Antigua   - MM: 74.50
6 Bed, 6 Baths, 5,370 SqFt Days Listed: 79
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift153ft.Concr

Never before on the market! This magnificent Port Antigua home on a double lot provides approximately 153 linear ft. of dockage. Enjoy beautiful bay views from this custom built Port Antigua pool home which is being sold fully furnished including the golf cart! Bring your toothbrush and start making family memories in this move-in ready home which was built to exacting standards. The commercial-grade, elegant 4-stop elevator takes you from the ground level to the rooftop deck which has a propane fire pit and and seating to enjoy fabulous sunsets. The 3rd floor features an open concept living, dining and kitchen with bay views as well as the master bedroom with his and hers separate full baths. Each floor has an on demand water heater, A/C , washer and dryer. The second floor has another

240  Costa Bravo Drive  For Sale, MLS 589104
$3,995,000
Lower Matecumbe
Port Antigua   - MM: 74.50
4 Bed, 4 Baths, 4,134 SqFt Days Listed: 142
-13.06% ($600,000) 2 Price Changes : Last Change 80 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift90ft.

Celebrate sunset views EVERY night from this beachfront Port Antigua home which also has dockage across Costa Bravo Dr. on the protected canal. The main living level boasts an open floor plan and vaulted ceilings, 3 bedrooms, 3 baths plus an office! The kitchen is open to the living and dining areas so that you can enjoy views of the bay while preparing the days catch and features a large cooking island with ample seating, Stainless steel GE Profile and Jenn-Air appliances. Enjoy bay views from the living area where 12 ft. sliding glass doors pocket out of sight and open to a spacious covered porch. Everything tastes better when you are enjoying bay views from the dining area. Another set of 12 ft. sliding glass doors in the dining area pocket to let the outside in. In addition.....

298  South Drive  For Sale, MLS 581391
$3,800,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
4 Bed, 4 Baths, 3,938 SqFt Days Listed: 664
-23.85% ($1,190,000) 5 Price Changes : Last Change 99 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Lift38ft.

This Islamorada Gem is located in a very private ocean front enclave. The open living/dining area over looks the ocean with 20 ceilings through floor to ceiling windows. Both master suites open to ocean view terraces. A luxurious den with 50 flat screen Apple TV is a quiet retreat. All levels are serviced by elevator. Situated on a gated 1/2 acre lushly landscaped lot with paver drive and two car garage, this home is one of only 4 in the enclave. The 38 protected dock has 20K LB lift in the HOA marina. The new marina park is newly landscaped. Concrete pool and spa has new equipment. A fully equipped poolside bar has new appliances including stainless grill, refrigerator and Ice maker. Quality construction with West Indies design. Offered furnished.

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 05-31-2020.

Broker's Edge Realty
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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