4403 HIGHLAND OAKS CIRCLE
Sarasota, FL 34235

3 Beds 3 Full 1 Half Bath 3016 sq ft 1 Day on Market HOA $2,354.00/yr

Rare opportunity in The Highlands: 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. Set 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+ restaurants and outstanding shopping!
A highly 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. Thoughtfully designed for maximum privacy, the primary suite and guest bedrooms occupy separate wings, offering four bedrooms, three-and-a-half baths, plus a flex room.
Outside, a large pool invites relaxation and entertaining, while the generous covered lanai provides ample space for alfresco dining and lounging, all overlooking the 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, two new A/C systems in 2025. Ideally situated outside the designated high-risk floodplain in flood zone X.
All near to all the fun The Meadows has to offer and five minutes to the UTC Mall, a world-class destination for shopping, dining, and entertainment.
Set on 1,600 lush acres just 15 minutes from Downtown Sarasota, The Meadows combines resort living with ...

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Listing Courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY
941-364-4000

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Per Month
Principal and Interest
Property Taxes 638
HOA Fees 196
Homeowners Insurance 412
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Property Last Updated: November 12, 2026 12:37 AM - ET