Steven Koleno

Steven Koleno Consumer-First Real Estate Architect

$2,300,000.00
1585 SOUTH DRIVE, SARASOTA, FL - 34239
3 beds
3.5 baths
2,764 sqft
$2,300,000.00
1585 SOUTH DRIVE, SARASOTA, FL - 34239
Steven Koleno
$2,300,000.00
3 beds
3.5 baths
2,764 sqft
1585 SOUTH DRIVE, SARASOTA, FL - 34239
For Sale
Photo 1
  • Built in 1964
  • 2 garage spaces
  • $832.13/sqft
  • Lot size: 16,433 sqft
  • 6 days on market

Set on a beautiful corner lot in the highly sought-after Cherokee Park neighborhood, this charming two-story residence offers three bedrooms, three-and-a-half baths, and a rare opportunity to create a home tailored to your vision. Surrounded by a lush, expansive yard with ample room for a pool, the property offers exceptional flexibility for its next owner. Enjoy the home's timeless character as it is, or take advantage of the opportunity to create your dream home in one of Sarasota's most established neighborhoods. Inside, a light-filled, open floor plan is complemented by beautiful wood floors and an inviting sense of warmth throughout. The main level features a comfortable guest bedroom with an adjacent full bath, as well as a spacious en-suite primary bedroom, offering the ease and convenience of first-floor living. Upstairs, a private en-suite retreat is filled with character, featuring charming dormer windows, built-in window seats, and extensive storage. Adding to the property's remarkable potential is a recently approved variance along the side of the lot, providing an additional 10 feet of buildable envelope and expanding the possibilities for a future renovation, addition, or new residence. Ideally situated West of the Trail, this exceptional property places you close to top-rated schools, Sarasota Memorial Hospital, the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and vibrant downtown Sarasota. With its coveted location, generous homesite, and unique development potential, this Cherokee Park property presents an extraordinary opportunity to create something truly special.

  • Directions: Osprey Avenue to West on South Drive. Home is on the right.
  • County: Sarasota
  • Geo subdivision: CHEROKEE PARK

Nearby Schools

Southside Elementary

Sarasota Middle

Sarasota High

Features

Financial

Let's get in touch!

Steven Koleno

Steven Koleno

Consumer-First Real Estate Architect

See also

For Sale
2420 NOVUS STREET, SARASOTA, FL - 34237
$2,250,000.00
4 bds
4.0 ba
2,802 sqft
2420 NOVUS STREET, SARASOTA, FL - 34237
For Sale
4508 WOODSIDE ROAD, SARASOTA, FL - 34242
$2,349,000.00
3 bds
2.0 ba
2,341 sqft
4508 WOODSIDE ROAD, SARASOTA, FL - 34242
For Sale
2631 PURITAN TERRACE, SARASOTA, FL - 34239
$2,150,000.00
4 bds
4.0 ba
3,675 sqft
2631 PURITAN TERRACE, SARASOTA, FL - 34239
Stellar MLS
  • Source: Stellar MLS
  • MLS #: A4704763
Listing updated: September 5, 2026 at 10:47AM
Listing provided by: Kelly Quigley, MICHAEL SAUNDERS & COMPANY
Last checked 5 days ago
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.