4403 HIGHLAND OAKS Circle Rare opportunity in The Highlands, with exceptional privacy, space and potential! Discover the possibilities in this spacious, single-story, four-bedroom pool home in The Highlands, the crown jewel of The Meadows. On an expansive 100-foot-wide lot with no neighbors in sight and tranquil preserve views, this home offers exceptional privacy in a phenomenal location, just five minutes from 90-plus restaurants and outstanding shopping. A sought-after floor plan features 3, 000 square feet under air and 4, 500 square feet under roof, including an expansive covered lanai ideal for Florida indoor-outdoor living. High ceilings, oversized windows and walls of sliding glass doors fill the home with natural light and showcase the beautiful, private setting. Offering four bedrooms, three-and-a-half baths, plus a flex room, it was thoughtfully designed for maximum privacy as the primary suite and guest bedrooms occupy separate wings. Outside, a large pool invites relaxation and entertaining, while the generous covered lanai provides ample space for alfresco dining and lounging, all overlooking a bountiful mango tree, queen palms and peaceful preserve. Ready for updating, this home offers tremendous potential, an outstanding floor plan and valuable improvements, including a 2016 tile roof and hurricane-rated garage door, 2017 pool resurfacing and two new air-conditioning systems in 2025. All near all the fun The Meadows has to offer and five minutes to the UTC Mall, a world-class destination for shopping, dining and entertainment. On 1, 600 lush acres just 15 minutes from downtown Sarasota, The Meadows combines resort living with the beauty of untouched nature. Enjoy 14 miles of scenic trails, an active social calendar, new fitness center, Junior Olympic pool, 10 pickleball courts, two 18-hole golf courses and 15 Har-Tru tennis courts. Ideally near award-winning beaches, cultural attractions, Nathan Benderson Park, Mote SEA Aquarium, Whole Foods, Trader Joe's, and the upcoming Sarasota Orchestra and Legacy Bike Trail. A rare opportunity to create your dream Florida home in an exceptional setting! A 2016 tile roof and hurricane-rated garage door, 2017 pool resurfacing, two new air-conditioning systems in 2025 and above floodplain in flood zone X.