$7,900,000 $42,409 est/mo Sourced by Back At You

207 & 209 E Carroll Street,Upper Matecumbe Key Islamorada, FL 33036

Upper Matecumbe Key Islamorada FL, 33036

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Experience the unparalleled appeal of FairWinds, nestled in the heart of coveted downtown Islamorada. This exceptional oceanfront estate is a distinctive and idyllic beachside compound, seamlessly blending casual elegance with the convenience of desirable amenities. Pass through the entrance gate, meander the Chicago brick drive, and enjoy the captivating, lush tropical gardens, complete with native and tropical specimens, as well as a variety of fruit trees that guide your way toward the serene pastel blues of the Atlantic Ocean. A private sandy beach awaits a secluded haven for cherished moments with friends and family. Privacy and recreation harmoniously coexist in the remarkable four bedroom, three and one-half bath grand Caribbean inspired main house, which features wrap-around porches and wide verandas, complete with awe-inspiring ocean vistas. Savor breathtaking sunrises and the historic Alligator Reef Lighthouse, with the occasional sea turtle nesting on your beach, as well as schools of bonefish and tarpon on the flats just of offshore. This property features a guesthouse with three bedrooms, two baths and split floor plan. In addition, there is a detached three-bay carriage house with private captain's or staff quarters on top. A spacious four-car garage beneath the main house ensures ample room for both land and sea adventure. Discover your slice of a Caribbean paradise right at home, within walking distance to excellent restaurants, resorts, spas, and charming shops that exemplify the essence of allure, Islamorada-style. Embrace simplistic beauty, barefoot elegance, and boundless possibilities that await at FairWinds.


Listing TypeFor Sale
Days On Site106
Listing Provided ByOcean Sotheby's International Realty | Eric M. Rizzo


Bath(s) 6 Total
SQ Feet4,931
ZoningR1 - Residential Single

Market Activity 33036

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The data relating to real estate for sale on this web site come s in part from the Internet Data Exchange program of the Marathon and Lower Keys Association of REALTORS®, Inc. MLS. Real Estate listings held by brokerage firms other than Coldwell Banker Schmitt are marked with the MLS logo and detailed information about them includes the name of the listing broker’s office.

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Learn More About This Property

CityUpper Matecumbe Key Islamorada
Zip Code33036
Area23 Upper Matecumbe
Community NameStrattons (82.5)
Listing VS Median (in Strattons (82.5))
low | high
100% of Average
low | high
100% of Average
$ / SqFt:
low | high
71.004003003738% of Average
On Site:
low | high
73.867595818815% of Average
Sourced by Back At You
Listing Updated: August 16, 2023 at 3:22:50 AM PDT