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

Total Listings 76
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$13,900,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
7 Bed, 7 Baths, 6,198 SqFt Days Listed: 175
-22.35% ($4,000,000) 1 Price Change : Last Change 33 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Welcome to your own private estate immersed on almost four acres in Islamorada with close to 400 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 drea

$13,000,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 516
-23.53% ($4,000,000) 5 Price Changes : Last Change 14 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.

$11,900,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 7,813 SqFt Days Listed: 63
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Built in 2006 and situated on over 10 acres off of the Old Highway on Plantation Key, this estate is luxury at its finest with a private and gated entrance. The property is nestled right on the Atlantic Ocean with 450 ft. of beach frontage and features some of the most beautiful tropical landscaping consisting of Sea Grape trees, and yellow and red Royal Poinciana trees, to name a few. Nestled between the main house and the guest house is a heated pool and hot tub designed with Keystone deck to complete the island feel of the exterior of the property. The aesthetic of the main and guest house resembles a Southern manor combined with regal Caribbean touches and attention to detail. The main house offers 6,652 sq. feet, where the third story is home to a grand master suite and an additional

$8,490,000
Plantation Key
Misc Plantation Key   - MM: 85.00
6 Bed, 6 Baths, 6,573 SqFt Days Listed: 725
-10.58% ($1,005,000) 2 Price Changes : Last Change 113 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.

$8,300,000
Plantation Key
Lake Harbor   - MM: 89.00
5 Bed, 5 Baths, 6,269 SqFt Days Listed: 407
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!

$7,900,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
8 Bed, 8 Baths, 4,931 SqFt Days Listed: 231
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

$7,900,000
Plantation Key
Key Heights   - MM: 88.50
5 Bed, 5 Baths, 5,457 SqFt Days Listed: 287
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!

$7,900,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
8 Bed, 8 Baths, 4,744 SqFt Days Listed: 287
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.

$7,500,000
Lower Matecumbe
Lower Mat Harbor   - MM: 75.00
4 Bed, 4 Baths, 4,610 SqFt Days Listed: 491
-5.66% ($450,000) 1 Price Change : Last Change 34 Days Ago
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!

$6,795,000
Plantation Key
Misc Plantation Key   - MM: 85.00
5 Bed, 5 Baths, 10,000 SqFt Days Listed: 43
PreConstructi - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

One of a kind offering. Start building your dream home and dock without the wait. Over 1250 feet of bay front! Privacy, security and seclusion abound. Active permit in hand. 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

$6,645,000
Plantation Key
Trop Coral Reef   - MM: 89.00
7 Bed, 7 Baths, 5,839 SqFt Days Listed: 359
-5.00% ($350,000) 1 Price Change : Last Change 15 Days Ago
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

$5,950,000
Upper Matecumbe Key Islamorada
Caribee Beach   - MM: 80.00
6 Bed, 6 Baths, 2,635 SqFt Days Listed: 58
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift100ft.

CARIBEE BEACH HOUSE is the perfect mix of old school Islamorada charm combined with present-day, stylish luxuries. One of the few oceanfront estates with a deep water basin and its own channel allowing access for larger vessels. 200 of shoreline with a sandy beach and fabulous views of Alligator Lighthouse. The 100 dock features a 24k lb boatlift and the irreplaceable concrete jetty has a boathouse and 4,500 lb lift for your skiff. The main house is 3 bedrooms / 3 bathrooms and is fully renovated. The new guesthouse is 3 bedrooms / 2 bathrooms and has a 3 bay garage on the first floor. Fully fenced-in and gated, a custom putting green, heated and chilled pool, zipline, and biking distance to everything Islamorada has to offer, makes for a perfect package! The property has the space and

$5,450,000
Windley Key
Galen Beach   - MM: 85.00
4 Bed, 4 Baths, 3,035 SqFt Days Listed: 293
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock,Basin,

Build a better life at Blue Harbor. This stunning contemporary 3,035 sq. ft. retreat is nestled on 1+ acre and redefines oceanfront living. With 200 feet of deepwater dockage and a private boat basin, this modern four bedroom is a truly unique property. In the heart of Islamorada, this newly renovated 4/3 celebrates the stunning Atlantic Ocean in every way with 360-degree panoramic ocean views from the second-floor wrap-around patio, to the stainless steel and glass-lined staircase, to each of the four luxurious bedrooms! Blue Harbor is designed to meet your every need. The state-of-the-art gourmet kitchen boasts crisp white custom cabinetry, quartz countertops, and state-of-the-art appliances like Wolfs induction Chefs range, a Subzero refrigerator, and a Miele dishwasher.

$5,000,000
Plantation Key
Key Heights   - MM: 88.50
4 Bed, 4 Baths, 4,103 SqFt Days Listed: 67
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift400ft.Concr

Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires Row... Islamoradas premier address. New dock with two new boat lifts (16,000 lb. and 10,000 lb.) to enjoy one of the best boating locations in the Keys, plus a 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 great income potential.

$4,950,000
Plantation Key
Key Heights   - MM: 88.50
5 Bed, 5 Baths, 2,557 SqFt Days Listed: 316
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.

$4,875,000
Plantation Key
Plantation Beach   - MM: 87.50
6 Bed, 6 Baths, 2,839 SqFt Days Listed: 36
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift100ft.

Welcome to one of Islamoradas most prestigious addresses and the epitome of upscale Keys living. An impressive offering that leaves no box unchecked and carries a major presence. In many ways this property is special, but the private canal that leads to the lagoon in the front yard is a favorite amongst guests. The main house underwent a full nut and bolt restoration while still preserving its original Keys character. The first floor offers an open kitchen and living area, as well as 3 bedrooms / 2 bathrooms with bay views from almost every room. The custom interior staircase leads to the second floor private master with endless bay views and its private porch. The detached guesthouse has 2 bedrooms and a bathroom on the second floor. The garage occupies the first floor and has front

$3,750,000
Lower Matecumbe
Mat Ocean Bay   - MM: 77.00
6 Bed, 6 Baths, 4,696 SqFt Days Listed: 355
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat RampRip Rap

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 fine 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...

$3,649,500
Lower Matecumbe
Port Antigua   - MM: 74.50
6 Bed, 6 Baths, 5,370 SqFt Days Listed: 42
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift77ft.Concre

A one-of-a kind home, located in the heart of Islamorada Fla., the fishing capital of the world. Enjoy beautiful bay views from this custom-built Port Antigua pool home which is being sold fully furnished including the golf cart, ice maker, kayaks, bikes and fishing equipment. Bring your toothbrush and clothes 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 seating to enjoy fabulous sunsets. The 3rd floor features an open concept living, dining and kitchen with unobstructed bay views, including the master bedroom with his and hers separate bathrooms. This custom home is impeccably built from the ground floor

$3,445,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 4,696 SqFt Days Listed: 142
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

$3,395,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
3 Bed, 3 Baths, 3,805 SqFt Days Listed: 1372
-12.93% ($504,000) 18 Price Changes : Last Change 315 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin113ft.

Beyond compare, this Polynesian inspired exquisite keys waterfront Harum designed custom home is complete. 3 bedrooms 3 and a half baths with additional office that could be 4th bedroom, pool, exquisite landscaping, 110ft plus deep water dock w/shore power, Lutron system with Onos Sound throughout. Marvel at the vaulted beam tongue and groove cathedral ceilings throughout and custom designed kitchen and living area opening up to a massive covered pavilion for entertaining in addition to the enormous covered entertaining and living area on ground level where you will also find sports and storage rooms and 2 separate car garages for boats or vehicles. Located on Hurricane Creek this residence offers deep water draft up to 6 ft with unlimited beam with easy access to Gulf, Bay and Atlantic.

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 10-20-2020.

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

1(800) 692-3605
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