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

Total Listings 112
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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: 213
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
$17,000,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 86
Single Family - 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
$9,495,000
Plantation Key
Misc Plantation Key   - MM: 85.00
6 Bed, 6 Baths, 6,573 SqFt Days Listed: 295
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. 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.

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: 61
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!

200  Atlantic Street  For Sale, MLS 579361
$7,900,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
8 Bed, 8 Baths, 4,744 SqFt Days Listed: 515
-1.25% ($100,000) 1 Price Change : Last Change 319 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Bunny Key, a premiere historic Islamorada oceanfront plantation. It has been over two decades since this property has been available. Known by its provenance that starts as the LaBranche Fishing Camp in 1937, where it is said the owner and author penned many a fishing tale with the ocean as his muse and passion for fly fishing as his motivation. 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. 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

  South Drive  For Sale, MLS 585035
$6,300,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
5 Bed, 5 Baths, SqFt Days Listed: 138
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 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. The 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.

181  Indian Mound Trail  For Sale, MLS 573005
$5,995,000
Plantation Key
Indian Waterways   - MM: 89.00
6 Bed, 6 Baths, 8,646 SqFt Days Listed: 989
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

MAKE YOUR LIFESTYLE CHANGE AT PINEAPPLE PLANTATION! Are you ready for year round sunsets and panoramic bay views from this elegant custom built home? Start by entering this gated estate, meander through the extraordinary grand entrance leading you to an expansive great room with soaring ceilings and over 8,000 sq. ft. of living space offering chefs kitchen, media room,

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: 777
+4.65% ($200,000) 6 Price Changes : Last Change 308 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!

298  South Drive  For Sale, MLS 581391
$4,290,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
4 Bed, 4 Baths, 3,938 SqFt Days Listed: 376
-14.03% ($700,000) 3 Price Changes : Last Change 104 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.

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: 81
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

144  Bayview Drive  For Sale, MLS 573791
$3,750,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
3 Bed, 3 Baths, 3,805 SqFt Days Listed: 942
-3.82% ($149,000) 17 Price Changes : Last Change 213 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin113ft.

Beyond compare, this Polynesian inspired exquisite keys waterway Harum Designed custom home is 99% complete, pool is in, landscaping is underway. This spectacular home is not to be missed if you are looking for a yachtsmans location w/over 110ft of deep water dockage w/unlimited beam on deep water Hurricane Creek. Cathedral ceilings grace this masterpiece and its 3 bedroom and 3.5 baths is complimented by custom LED lighting, drop down TV. Incredible storage, 2 garages, generous and spacious covered gathering areas. The residence boasts an extraordinary creekside covered balconies overlooking Hurricane Creek with views of the Florida Bay making this a Florida Keys Treasure. The finished work detail is to much to list. Contact agent for full details and showing appointment.

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: 167
-5.66% ($219,000) 1 Price Change : Last Change 103 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: 177
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: 89
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.

75971  Overseas Highway  For Sale, MLS 580319
$3,399,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
4 Bed, 4 Baths, 6,065 SqFt Days Listed: 452
-2.89% ($101,000) 1 Price Change : Last Change 262 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None,Other Dockage

Income Property! A successful weekly vacation rental, Turtle Nest Estate has achieved an average gross income of $200,000/year so this property could potentially be self-funding! With booked rentals in place, the buyer will honor all future bookings and leases will be transferred upon sale. In addition to rental income, you can also enjoy your own tropical beachfront paradise in desirable Islamorada near all the most popular diving and fishing spots. Relax on the 150-foot beach, soak in some rays by the pool, or enjoy nearby fine dining, entertainment & local attractions. This luxurious home offers more than 6,000 sf under air, an oceanfront pool with integrated hot tub, a wade-in sandy beach and an observation pier. Two-car garage, elevator, theater room, split plan, guest wing & more!

161  Palo De Oro Drive  For Sale, MLS 581489
$3,350,000
Plantation Key
Venetian Shores   - MM: 86.00
8 Bed, 8 Baths, 6,308 SqFt Days Listed: 369
-25.56% ($1,150,000) 3 Price Changes : Last Change 170 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 100ft.Concrete

Enjoy astounding views upon entering this estate home with soaring ceilings and floor-to-ceiling windows. The home is set on nearly a half-acre lot and offers eight bedrooms and six-and-a-half bathrooms. Views of Snake Creek and the ocean beyond can be seen from screened-in balconies on all three levels. A beautiful screened-in pool and spa, 100 feet of protected dockage and mature tropical landscaping with lighting complement the outdoor oasis. The home is complete with a double four-car garage, separate guest quarters, an elevator, and a gated driveway.

288  South Drive  For Sale, MLS 584685
$3,300,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
5 Bed, 5 Baths, 3,692 SqFt Days Listed: 163
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin

Spectacular & Private Oceanfront Estate with Pool & Protected Dockage in a deep water, modern marina covered with Ipe wood, surrounded by magnificent Silvestre palms and adjacent to a .75 acre sandy, water front lot covered with coconut palm trees! This magnificent concrete home is located in one of the most prestigious communities in all of the Florida Keys, Plantation Point, a very private, four home, double gated community in Islamorada; The Sport Fishing Capital of the World.

153  Sunset Drive  For Sale, MLS 582184
$3,295,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
4 Bed, 4 Baths, 2,618 SqFt Days Listed: 317
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

This original 1971 beach house has been entirely renovated, complete with a brand new top-floor master suite addition and fresh coastal design. The residence features solid concrete block construction, three bedrooms, two bathrooms, and legal downstairs one-bedroom, one-bathroom guest quarters. Additional amenities include a covered carport, plus a canalfront lot with protected dockage, a boat lift, a pool, and a bar beneath a tiki hut. This property is a must-see to appreciate the beautiful interior finishes, panoramic ocean views, and fantastic outdoor spaces.

75445  Overseas Highway  For Sale, MLS 586728
$3,240,000
Lower Matecumbe
Matecumbe Ocean Bay   - MM: 75.00
4 Bed, 4 Baths, 3,185 SqFt Days Listed: 17
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

OCEANFRONT ESTATE! Behind the gate and concrete wall surrounding this property, you will find the most beautifully remodeled, four bedroom, four and one-half bath home, overlooking the Atlantic Ocean. Three en suite bedrooms feel like master suites with phenomenal views. Fourth bedroom and adjacent bath located its in own wing. Open gathering space with built-in workspace and wet bar; amazing modern kitchen. Featuring a sandy beach complete with horseshoes & hammock, a grand, in-ground pool, boat ramp, concrete seawall and potential for dockage! Three exterior terraces/lanais for entertaining or private sunbathing all with incredible ocean views. The half bath is serviceable by a door leading to pool. One car garage and plenty of parking outside for vehicles/RV. Paradise Found!

110  Bayview Isle Drive  For Sale, MLS 574354
$3,200,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 3,240 SqFt Days Listed: 909
-13.51% ($500,000) 3 Price Changes : Last Change 29 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift140ft.

ANCHORS AWEIGH - 140 of deep-water, protected, concrete/paved dockage is enjoyed at this serenely secluded property with sunset views. It is rare to find 2 adjoining lots in Venetian Shores with beautiful bay views, and convenient, direct access to Snake Creek. Remodeled in 2005 & designed to take advantage of magnificent views from every level. Downstairs rec room also used as 5th bedroom.

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 08-17-2019.

Shoreline Properties
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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