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Under contract-accepting backup offers. Step inside this freestanding villa and instantly feel at home. With over 2,100 square feet of living space, cathedral ceilings, and a spacious great room featuring a wood-burning fireplace and built-in wet bar, this residence blends comfort, character, and the charm of The Meadows lifestyle. The flexible three-bedroom layout includes a room with double doors currently used as a den"”ideal for a home office or cozy reading retreat. Freshly painted and featuring new carpet in the bedrooms, the home feels bright and inviting, while allowing the next owner the opportunity to personalize a few updates to their own taste. An enclosed sun porch offers a front-row view of the golf course, perfect for morning coffee or evening sunsets. The courtyard-style entry and attached two-car garage provide easy access and a sense of privacy, while the large primary suite offers a peaceful haven with generous space and a tranquil view. Highland Park is an intimate enclave of just 20 villas, offering a community pool and panoramic views of gardens and golf course greens. The Meadows features miles of walking and biking trails, an active community center, and a full social calendar"”all within minutes of Nathan Benderson Park, local shopping, dining, and a short drive to downtown Sarasota and the beaches. 4442 Highland Park is more than a home"”it's an invitation to live surrounded by beauty, convenience, and a welcoming community.
| DAYS ON MARKET | 116 | LAST UPDATED | 2/5/2026 |
|---|---|---|---|
| TRACT | HIGHLAND PARK | YEAR BUILT | 1988 |
| COMMUNITY | 34235 - Sarasota | GARAGE SPACES | 2.0 |
| COUNTY | Sarasota | STATUS | Pending |
| PROPERTY TYPE(S) | Condo/Townhouse/Co-Op |
| Elementary School | Gocio Elementary |
|---|---|
| Jr. High School | Booker Middle |
| High School | Booker High |
| PRICE HISTORY | |
| Prior to Jan 23, '26 | $400,000 |
|---|---|
| Jan 23, '26 - Today | $375,000 |
| ADDITIONAL DETAILS | |
| AIR | Central Air |
|---|---|
| AIR CONDITIONING | Yes |
| AMENITIES | Cable TV, Maintenance Grounds, Maintenance Structure, Pest Control |
| APPLIANCES | Dishwasher, Dryer, Range, Range Hood, Refrigerator, Washer |
| AREA | 34235 - Sarasota |
| CONSTRUCTION | Block, Stucco |
| EXTERIOR | Courtyard |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central |
| HOA DUES | 2049 |
| INTERIOR | Coffered Ceiling(s), Crown Molding, Eat-in Kitchen, High Ceilings, Walk-In Closet(s), Wet Bar |
| PARKING | Garage Door Opener, Attached |
| SEWER | Public Sewer |
| STORIES | 1 |
| STYLE | Florida |
| SUBDIVISION | HIGHLAND PARK |
| TAXES | 3127 |
| UTILITIES | Cable Available, Cable Connected, Electricity Connected, Sewer Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Garden, Golf Course |
| WATER | Public |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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*Estimate only
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Listing provided by Ryndie Brusco, MICHAEL SAUNDERS & COMPANY, 941-951-6660
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 2/21/26 2:21 AM PST.
This IDX solution is (c) Diverse Solutions 2026.