Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

$5,475,000
75851 Overseas Highway
Lower Matecumbe, FL 33036
MLS# 614879
Status: Closed
5 beds  |  7 baths  |  3978 sqft
 | 
Southwind
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Southwind Gated private oceanfront estate Welcome! 5 bedrooms, 6.5 bathrooms Pickleball!! Pickleball and golf Turf putting green! Surrounded by mature palms and low maintenance tropical landscape. Paver driveway Beautiful entrance, garage Dining room and counter dining, all with views. Kitchen open to dining room Island kitchen with ocean views Spacious dining room with ocean views. Dining and entrance foyer. Living open to dining room Main living room with walls of glass form amazing ocean views! Living room with open ocean views. Living room to balcony, first floor First floor covered balcony overlooking ocean, beach and pier. First floor covered dining with ocean and beach views. Covered outdoor dining on first floor. First floor out door dining overlooking beach and ocean. Custom stairway with etched glass and special lighting. First floor guest bedroom Guest bath First floor wrap around patio First floor Guest bedroom First floor balcony view of yard. Guest bedroom Guest bath From first floor to second, custom stairway. Custom stairway showcasing etched glass mural. Stairway to top floor. Top floor landing Top floor living room with tongue and groove ceilings. Top floor morning kitchen Top floor living with stunning views. Top floor sitting area. Top floor guest wing Top floor guest suite Top floor guest suite with private ocean view balcony Top floor guest bedroom balcony Top floor guest room balcony Spectacular beach and pier. Oceanview from top floor balcony. Guest bath Guest suite Top floor guest room balcony view Guest room Guest bath Primary bedroom with private balcony Primary beroom with private balcony Primary bedroom Top floor primary bedroom balcony Top floor primary bedroom balcony Top Floor balcony overlooking pool. Top floor south balcony view. Primary bath Primary suite bathroom Primary suite bathroom Top floor primary bath covered balcony. Primary suite bathroom 75851 Overseas Hwy Top floor guest room view. North side South side First floor wrap-around porch view of pool. Bar and covered recreation area. Covered bar and entertainment area. Sweeping stairway to pool deck next to covered bar and beach. Gorgeous pool and spa Pool and spa with extra features and outdoor shower. Beach Picture yourself here! 75851 Overseas Hwy Firepit Exquisite oceanfront home! Concrete construction. 75851 Overseas Hwy From the fishing pier... 75851 Overseas Hwy ...Into the ocean. 75851 Overseas Hwy 75851 Overseas Hwy 75851 Overseas Hwy 75851 Overseas Hwy 75851 Overseas Hwy Oceanfront estate with all the amenities for Keyslife fun! 75851 Overseas Hwy Highway to ocean Island living. 75851 Overseas Hwy Looking west. Birdseye of the beautiful beach! Birdseye 75851 Overseas Hwy 75851 Overseas Hwy 75851 Overseas Hwy 75851 Overseas Hwy

Property Description
Welcome to your private tropical retreat in the heart of Islamorada, Florida Keys. This stunning gated oceanfront estate showcases unparalleled beauty with a private walk-in sandy beach, offering direct access to crystal-clear waters. Designed for both relaxation and recreation, the property features 5 spacious bedrooms, 6.5 luxurious bathrooms, a resort-style pool, a pickleball court, and a putting green, all set amidst lush, tranquil landscaping. Wake up to spectacular ocean views from nearly every room, and enjoy the serenity of your tropical surroundings. This property is offered turn-key, fully furnished and equipped, making it an ideal primary residence, second home, or lucrative vacation rental opportunity in one of the Keys' most desirable locations.Your dream oceanfront lifestyle awaits in Islamorada — where every day feels like a vacation.

Details
Maps
Contract Information
Current Price: $5,475,000
Listing Date: 2025-05-03
Listing Board: Florida Keys
Leased Price Monthly: $5,475,000
As is Rght to Inspct: Yes
Species List: Yes
Location, Tax & Legal
Street #: 75851
Street Name: Overseas
Street Suffix: Highway
Key/Island: Lower Matecumbe
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Mat Ocean Bay (75.0)
Area: 22 - Lower Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 1
Pool: Yes
Year Built: 1992
Lot Size: 100' x 380'
Lot SqFt: 37447
Lot Sqft Source: Property Data Card
Acres: 0.86
Living Apx SqFt: 3978
SqFt Source: Property Data Card
Total Bedrooms: 5
Full Baths: 6
Half Baths: 1
Total Baths: 7
Rentals Allowed: Yes
Min Rental Days: 7
Association Info
Mandatory Home Owners Asc: No
Voluntary Home Owners Asc: No
1st Right of Refusal: No
License Info
Transient Rntl Licns: Yes
Dockage
Dock Length: 150
Dock: Wood
Building Style
Above Flood: Yes
# Stories: 3 Stories
Pool Info
Heated: Yes
Status Change Info
Under Contract Date: 2026-03-31
Leased Date: 2026-05-05
Leased Price Monthly: $5,475,000
Status: Closed
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Oceanfront; Open Water
Waterview: Ocean View; Open Water View
Vehicle Storage: Garage; Attached; Auto Door Opener; Covered Parking
Furnished: Furnished
Cooling: Ceiling Fans(s); Central Air
Heating: Central
Utilities: Buyer to Verify; Cable Available; FKAA; Municipal Sewer
Interior Features: Entrance Foyer; Granite Counter Top; Smoke Alarms; Storage; Walk-in Closet(s); Wet Bar
Appliances: Dishwasher; Dryer; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer; Wine Cooler
Exterior Features: Bar; Fencing; Hot Tub; Lighting; Outdoor Shower; Privacy Wall/Fence; Sandy Beach; Storage
Pool Info: In Ground; Concrete; Decked
Construction: CBS; Concrete
Floor: Marble; Tile
Roof: Metal Roof
Pets: Pets Allowed
Neighborhood Feature: Bike Paths
Security: Electric Gate
Land Size: 1/2 - Less Than 1 AC
Terms: Cash; Conventional
Listing Office: Ocean Sotheby's International Realty

Last Updated: May - 05 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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