1585 South Drive, SARASOTA, FL 34239
Local realty services provided by:Better Homes and Gardens Real Estate Atchley Properties
Upcoming open houses
- Thu, Sep 2502:00 pm - 04:00 pm
- Sun, Sep 2812:00 pm - 03:00 pm
Listed by:nick gard
Office:coldwell banker realty
MLS#:A4666035
Source:MFRMLS
Price summary
- Price:$2,275,000
- Price per sq. ft.:$618.54
- Monthly HOA dues:$27.08
About this home
Welcome to 1585 South Drive, a timeless cottage-style residence in the beloved West of Trail community of Cherokee Park. Thoughtfully updated and rich with character, this home seamlessly blends historic charm with modern comfort. Refinished white oak floors, abundant natural light, stylish finishes, and a gracious, contemporary layout make it truly move-in ready. Elevated more than 10 feet above sea level yet just three houses from the bay, the home enjoys both beauty and peace of mind on a corner lot at the quiet end of the street.
From the inviting brick front porch, step into a foyer with custom board-and-batten detailing. To the right, a generous living room encourages gathering; to the left, a versatile office, den, or sitting room is tucked behind sliding doors for a quieter retreat. Expansive windows frame leafy views and bathe the interiors in light.
At the heart of the home, the oversized kitchen impresses with a large central island, abundant counter space, walk-in pantry, wet bar, and KitchenAid appliances. The adjoining dining room opens to the backyard and screened porch, creating seamless indoor-outdoor living.
The primary suite is privately situated on the main level, offering a spacious walk-in closet, serene ensuite bath, and direct screened porch access. Nearby, a second bedroom with its own hall bath serves perfectly as a guest suite, children’s room, or home office. Upstairs, a private retreat includes a large bedroom with dormer windows, built-in window seats, an ensuite bath, and extensive storage.
Additional highlights include a recently remodeled marble powder room, a well-equipped laundry room, an irrigation well, and an attached two-car garage. The generously sized lot offers ample room for a pool, guest house, or future expansion.
Sarasota's West of Trail neighborhoods are coveted for their proximity to Sarasota Memorial Hospital, downtown, and the sugar white sands of Siesta Key. Cherokee Park is perhaps the most prized of these, celebrated for its stately homes, wide tree-lined streets with sidewalks, walkability to Southside Village and Southside Elementary, and cherished traditions — from bustling Halloweens to twinkling luminaries and carriage rides at the holidays. While the surrounding streets boast their share of impressive new construction, this well-proportioned and well-preserved original stands apart for its enduring charm, turnkey livability, and exceptional value. Designer furnishings by Pecky Interiors are optionally available.
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Home facts
- Year built:1964
- Listing ID #:A4666035
- Added:1 day(s) ago
- Updated:September 24, 2025 at 05:32 PM
Rooms and interior
- Bedrooms:3
- Total bathrooms:4
- Full bathrooms:3
- Half bathrooms:1
- Living area:2,764 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Electric
Structure and exterior
- Roof:Shingle
- Year built:1964
- Building area:2,764 sq. ft.
- Lot area:0.38 Acres
Schools
- High school:Sarasota High
- Middle school:Brookside Middle
- Elementary school:Southside Elementary
Utilities
- Water:Public, Water Connected
- Sewer:Public Sewer, Sewer Connected
Finances and disclosures
- Price:$2,275,000
- Price per sq. ft.:$618.54
- Tax amount:$25,811 (2024)
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