1585 South Drive, Sarasota, FL 34239
For Sale $2,300,000
Save Property
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.
Ceiling Fans(s)
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Stone Counters
Walk-In Closet(s)
Window Treatments
Taxes: $25,958.18
Tax Year: 2025
Bar Fridge
Built-In Oven
Dishwasher
Disposal
Dryer
Microwave
Tankless Water Heater
Washer
Trees/Woods
Elementary School: Southside Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Sarasota High
MLS Area: 34239 - Sarasota/Pinecraft
Total Square Footage: 3,678
Price per Square Feet: $832.13
Total Floors: 2
Water: Public
Construction: Wood Siding
Date Listed: 2026-09-04 00:00:00
Furnished: Unfurnished
Parking: Driveway, Garage Door Opener
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Tile, Wood
Roof: Shingle
Heating: Central
Cooling: Central Air
Laundry: Inside, Laundry Room
Pets: Yes
Sewer: Public Sewer
Lot Desc.: Corner Lot, City Limits, Sidewalk, Paved
Parcel ID: 2039030009
Listing Courtesy Of: Michael Saunders & Company
kellyquigley@michaelsaunders.com
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.
Property Details
Price: $2,300,000
Sq Ft: 2,764
($832 per
sqft)
Bedrooms: 3
Bathrooms: 3
Partial Baths: 1
City: Sarasota
County: Sarasota
Type: Single Family
Development: Cherokee Park
Acres: 0.3800
Year Built: 1964
Listing Number: A4704763
Status Code: A-Active
Taxes: $25,958.18
Tax Year: 2025
Garage:
2
/
Y
Furnishings: Unfurnished
Pets Allowed: Yes
Interior Features:
Ceiling Fans(s)
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Stone Counters
Walk-In Closet(s)
Window Treatments
Financial Information:
Taxes: $25,958.18
Tax Year: 2025
Equipment:
Bar Fridge
Built-In Oven
Dishwasher
Disposal
Dryer
Microwave
Tankless Water Heater
Washer
View:
Trees/Woods
School Information:
Elementary School: Southside Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Sarasota High
Additional Information:
MLS Area: 34239 - Sarasota/Pinecraft
Total Square Footage: 3,678
Price per Square Feet: $832.13
Total Floors: 2
Water: Public
Construction: Wood Siding
Date Listed: 2026-09-04 00:00:00
Furnished: Unfurnished
Parking: Driveway, Garage Door Opener
Garage Description: Y
Garage Spaces: 2
Attached Garage: Y
Flooring: Tile, Wood
Roof: Shingle
Heating: Central
Cooling: Central Air
Laundry: Inside, Laundry Room
Pets: Yes
Sewer: Public Sewer
Lot Desc.: Corner Lot, City Limits, Sidewalk, Paved
Parcel ID: 2039030009
Map of 1585 South Drive, Sarasota, FL 34239
Listing Courtesy Of: Michael Saunders & Company
kellyquigley@michaelsaunders.com