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

Total Listings 103
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75900  Overseas Highway  For Sale, MLS 583768
$18,000,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
7 Bed, 7 Baths, 6,198 SqFt Days Listed: 331
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Nestled in six tropical acres on the bay in Islamorada on Lower Matecumbe Key is this rare parcel boasting over 600 feet of white sand beach and deep water dockage. This spectacular private estate offers 6,198 square feet of living space with six bedrooms and six-and-a-half bathrooms. The guest home offers an additional 418 square feet with one bedroom and one bathroom. Enter down a private driveway cocooned by tropical landscaping and arrive on the doorstep of this stately island-style residence. The distinctive design and craftsmanship are evident upon entering. This one-of-a-kind estate was designed to take in the captivating bay views from every room. Offering an elegant living room, formal dining room, comfortable family room and spacious sunroom with vaulted ceilings.

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: 204
-11.76% ($2,000,000) 1 Price Change : Last Change 72 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: 413
-6.27% ($595,000) 1 Price Change : Last Change 41 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: 95
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 Mimi 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: 179
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!

158  Key Heights Drive  For Sale, MLS 588557
$7,394,000
Plantation Key
Key Heights   - MM: 88.50
5 Bed, 5 Baths, 6,183 SqFt Days Listed: 8
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: 47
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 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 wood doors, ironwork fixtures,

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: 112
PreConstructi - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Pre-construction! No waiting to build your dream home in paradise! Building permit in hand for main house, guest house and caretakers cottage. Dockage assured in Village Council Meeting. THE CROWN JEWEL OF ISLAMORADA is a must see - Over 21 acres spanning from US-1 to the beautiful bay. Over 1250 feet of secluded bay front! Running from US-1 to the bay, your estate insures privacy and seclusion like no other as well as year round sunsets. Fish, snorkel and swim in your own secluded cove, or fish, kayak and paddle board in your very own free flowing creek (historically known as Little Snake Creek) connecting two salt water lakes loaded with tarpon and snapper. A very rare opportunity to own a true trophy estate in the Florida Keys. 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: 256
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: 11
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.

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: 4
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: 54
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: 895
+4.65% ($200,000) 6 Price Changes : Last Change 427 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!

1108  Venetian Boulevard  For Sale, MLS 585884
$3,995,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 4,696 SqFt Days Listed: 199
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Davits120f

This Venetian Shores Bay Front home offers everything for the serious boater. With 120 of concrete dock, a 60,000 # extra wide boat lift and davits for your bay boat this home can handle all your vessels. There is plenty of depth and a wide channel (88) will accommodate boats as large as 65 with easy ocean access through Snake Creek. The third floor is an open concept living room, dining room and kitchen with built in cabinets has expansive open water views. There are 3 bedrooms with fantastic views on the second floor. The master has his and her bathrooms and walk-in closets. The ground floor has two bedrooms with a Jack and Jill bathroom. There is also a storage room for all of your boating accessories. With over 12,000 sq ft this is one of the largest lots in Venetian Shores

80639  Old Highway 101 For Sale, MLS 587835
$3,995,000
Upper Matecumbe Key Islamorada
Maison Matecumbe   - MM: 81.00
4 Bed, 4 Baths, 2,997 SqFt Days Listed: 54
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Welcome to Maison Residences, your private oceanfront retreat in Islamorada. Enjoy open ocean views as soon as you step inside the front door! The view widens as you walk through the kitchen and dining area to the living area and the open lanai. This same view can be enjoyed from the luxurious master bedroom and balcony. Nature lovers can watch the wading birds feeding in the shallows, the pelicans diving for breakfast and porpoises playing without leaving your porch. Views of the lawn, palm trees, beach, dock and ocean will fill our mind and entice you to come back often. This smart home was finished with great attention to detail and features 10 ft. ceilings, 9 ft. doors, 2 AC units with 3 zones, Wolf and SubZero appliances, privately keyed elevator, 86 ft. resort style pool,

298  South Drive  For Sale, MLS 581391
$3,990,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
4 Bed, 4 Baths, 3,938 SqFt Days Listed: 494
-20.04% ($1,000,000) 4 Price Changes : Last Change 61 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.

77001  Overseas Highway  For Sale, MLS 588012
$3,750,000
Lower Matecumbe
Mat Ocean Bay   - MM: 77.00
6 Bed, 6 Baths, 4,696 SqFt Days Listed: 43
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp145ft.Rip R

Tucked away on two exquisite oceanfront acres with sandy beach is this perfect island retreat. Lush tropical gardens with tall coconut palms cocoon the 5 bedroom, 5 1/2 bath 4700SF residence plus separate poolside guest quarters. A welcoming foyer opens to a showcase stairway which leads to the top floor master suite with private oceanfront balcony and spacious master bath with double walk-in closets.The open living area with endless ocean views boasts exquisite finishes such as tiled custom bar, polished porcelain tile floors, and soothing colors reflecting the casual Keys life style. The gorgeous kitchen features a granite-topped island with high quality appliances, a pantry and laundry room. Wrap-around porches offer lazy ocean gazing over the sandy beach to the sparkling Atlantic...

80531  Old Highway  For Sale, MLS 584600
$3,650,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
3 Bed, 3 Baths, 2,044 SqFt Days Listed: 285
-5.66% ($219,000) 1 Price Change : Last Change 222 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None,Other DockageCo

A one-of-a-kind 4.33-acre estate on Upper Matecumbe Key. Enter the gate and follow the classic brick driveway to one of Islamoradas most private settings. The main house, which is above the flood zone, offers two bedrooms and two-and-a-half bathrooms, featuring high beamed ceilings, tile floors, and ocean views. A guest cottage offers one bedroom, one bathroom, and a large sitting room. Watch the colors of beautiful sunrises and incredible sunsets reflect off Alligator Lighthouse from all rooms. Look for tailing bonefish and wading birds, or just sit by the pool and relax--Mother Nature is your living room. A caretakers cottage as well as a guest cottage can be added to the property as of right. Two additional lots have the possibility to be rezoned.

262  Sunset Drive  For Sale, MLS 584415
$3,600,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
4 Bed, 4 Baths, 2,835 SqFt Days Listed: 295
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift90ft.

Mesmerizing water views from just about every room in this four-bedroom, three-and-a-half bathroom home including downstairs guest quarters. This beautiful house with beach access has a multitude of amenities such as natural coral accents, a gourmet kitchen with custom wood cabinetry, double ovens, and bar seating. The wonderful outdoor living spaces include an in-ground pool with a heater, chiller, lights and a waterfall, and terraces with open ocean views. Additional amenities include dockage for two boats, electric shutters, a multi-car garage, a workshop, and an elevator with etched glass artistry. The third floor is all master suite with elevator access, dual walk-in closets, an office, a sitting area, a spacious master bathroom, and two balconies for sunrise and sunset views.

160  Stromboli Drive  For Sale, MLS 585753
$3,500,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 4,353 SqFt Days Listed: 207
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Great views of Snake Creek and out to the ocean from this beautiful 5 bedroom home on almost 1/2 acre of creekfront lot in Venetian Shores. Approximately 130 along Snake Creek and approximately 160 along the canal. Home features split level with 4 bedrooms on 1st level, large living/kitchen area with screened balcony on mid level and master bedroom on top level, all connected with soaring open foyer. Nice pool with spa, screened outdoor grilling area, 9 hole putt-putt golf course along creek and canal, large garage, davits and nicely landscaped grounds.

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 12-13-2019.

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

1(800) 692-3605
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