1585 SOUTH DRIVE Sarasota, FL $ 2,300,000
1585 SOUTH DRIVE
$ 2,300,000
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1585 SOUTH DRIVE

Sarasota, FL, 34239
$ 2,300,000
Bedrooms3 Baths3.1 Sq 2,764

Monthly Estimate*

$ 15,886

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Single Family Home for sale in Sarasota, FL

for $2,300,000 with 3 bedrooms and 3 full baths, 1 half bath. This 2,764 square foot home was built in 1964 on a lot size of 0.38.

Under contract-accepting backup offers. 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.

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Single Family Contingent

Price

$ 2,300,000

Bedrooms

3

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 25,958

Style

Single Family Residence

Lot Size

0.38

Year Built

1964

Town/City

Sarasota

County/Region

Sarasota

MLS | Web ID

A4704763

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities Electricity Connected Natural Gas Connected Water Connected
Roof Shingle
Appliances Bar Fridge Built-In Oven Dishwasher Disposal Dryer Microwave Tankless Water Heater Washer
Zoning RSF1
Garage Spaces 2
Patio/Porch Features Deck Front Porch Rear Porch Screened
Construction Materials Wood Siding
Pets Allowed Yes
Year Built 1964
View Trees/Woods
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Sarasota
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name CHEROKEE PARK
Facing Direction South
Garage Y/N true
Total Rooms 7
Full Baths 3
Status Pending
Directions Osprey Avenue to West on South Drive. Home is on the right.
High School Sarasota High
City SARASOTA
Senior Community Y/N false
MLS Area 34239 - Sarasota/Pinecraft
Lot Size Units Square Feet
Lot Size Square Feet 16433
Carport Y/N false
Listing Terms Cash Conventional
Elementary School Southside Elementary
Land Lease Y/N false
Tax Annual Amount 25958.18
Middle/Junior High School Sarasota Middle
Property Condition Completed
Additional Parcels Y/N false
Lease Considered Y/N true
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active Under Contract
Occupancy Type Vacant
Tax Lot 1
Legal Description BEG NE COR LOT 1 BLK C TH S 150 FT TH W 100 FT TH N 150 FT TH W 42 FT TH N 42 FT TH S 56-19 50.47 FT TH W 68-45 E 38.62 FT TH S 89-58 E 63.99 FT TO POB BEING PART OF REPLAT OF CHEROKEE PARK
Minimum Lease 1 Month
Water Access Y/N false
Additional Rooms Family Room Inside Utility
Water View Y/N false
Flood Zone Code X
In Law Suite YN false
Flood Zone Code X Y
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Interior
Interior Amenities Ceiling Fan(s) Living Room/Dining Room Combo Primary Bedroom Main Floor Stone Counters Walk-In Closet(s) Window Treatments
Flooring Tile Hardwood
Furnished Y/N Unfurnished
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 1
Laundry Features Inside Laundry Room
Total Bedrooms 3
Total Baths 4
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Exterior
Exterior Amenities French Doors Irrigation System
Vegetation Trees/Landscaped
Parking Features Driveway Garage Door Opener
Lot Features Corner Lot City Lot Sidewalk
Water Source Public
Lot Size Area 16433
Foundation Details Crawlspace
Spa false
Building Area Total 3678
Lot Size Acres 0.38
Road Surface Type Paved Asphalt
Private Pool false
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Street Paved
Road Responsibility Public Maintained Road
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* Excluded Features
List By
Michael Saunders & Company

Broker

kellyquigley@michaelsaunders.com

Email

Affordability Calculator

$18,049
Per Month
88%
12%
0%
Monthly Principal & Interest
$15,886
Monthly Property Taxes
$2,163
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Sarasota High High School High School
Pricing History
DatePricePrice ChangeDescription
9/4/2026$2,300,000 Listed Price

Map


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1585 SOUTH DRIVE, Sarasota, FL, 34239 is a Single Family Home for sale at $2,300,000 with 2,764 sqft and a lot size of 0.38. 1585 SOUTH DRIVE has 3 bedrooms, 3.1 baths, and was built in 1964. The property's zip code is 34239 which is in Sarasota, FL