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$2,300,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,764 Sq. Ft.
  • Updated 13 days ago
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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.

Full Property Details for 1585 South Dr

General

  • Price: $2,300,000
  • Taxes: $25,958 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4704763
  • Updated: 9/4/2026
  • Added to Site: 14 day(s) ago

Rental Information

  • Min. Lease: 1 Month

Interior

  • Number of Rooms: 7
  • Interior Features: Ceiling Fan(s), Living Room/Dining Room Combo, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s), Window Treatments
  • Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Microwave, Tankless Water Heater, Washer
  • Furnishings: Unfurnished
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Room

Exterior

  • Exterior Features: French Doors, Irrigation System
  • Deck/Patio: Deck, Front Porch, Rear Porch, Screened
  • Porch/Patio/Deck: Deck, Front Porch, Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener

Location

  • Area: 34239 - Sarasota/Pinecraft
  • County: Sarasota
  • Development Name: 34239 - Sarasota/Pinecraft
  • Subdivision: CHEROKEE PARK
  • Driving Directions: Osprey Avenue to West on South Drive. Home is on the right.
  • Direction Faces: South

School Information

  • Elementary School: Southside Elementary
  • Middle School: Sarasota Middle
  • High School: Sarasota High

Community

  • Community Name: 34239 - Sarasota/Pinecraft
  • Association: Yes

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Natural Gas Connected, Water Connected

Structural Information

  • Exterior Const.: Wood Siding
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 2,764
  • Sq. Ft. Source: Public Records
  • Year Built: 1964

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.38
  • Lot Size (Sq. Ft.): 16,433
  • Lot Size: 16433
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt

Financial Considerations

  • Assoc Fee Desc.: Optional
  • Tax Amount: $25,958.18
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • 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
  • Flood Zone Info: X
  • APN: 2039030009
  • Property ID: 2039030009
  • Block/Lot/Section: C

Listed by Michael Saunders & Company

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Listing agent

— 1585 South Dr —

  • Michael Saunders & Company

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1585 South Dr

School District:Sarasota County School District
NameGradesDistance
Southside Elementary School, Sarasota, FL
1901 Webber Street, Sarasota, FL 34239
PK-50.4 mi
Brookside Middle School
3636 South Shade Avenue, Sarasota, FL 34239
6-81 mi
Sarasota High School
2155 Bahia Vista Street, Sarasota, FL 34239
9-121.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1585 South Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/04/2026
Listed
$2,300,000
—
MLS
12/02/2025
Sold
$2,300,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1585 South Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$25,958
1%
$1,707,800
-1%
2024
$25,811
2%
$1,728,000
3%
2023
$25,279
120%
$1,684,300
115%
2022
$11,482
-1%
$783,987
3%
2021
$11,610
—
$761,152
6%
2021
$11,610
-8%
$719,600
-7%
2019
$12,655
138%
$771,600
122%
2018
$5,308
3%
$347,591
6%
2017
$5,158
1%
$328,915
2%
2016
$5,125
-1%
$322,150
1%
2015
$5,197
—
$319,911
1%
2014
$5,189
1%
$317,372
1%
2013
$5,162
—
$312,682
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Michael Saunders & Company

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1585 South Drive, Sarasota, FL 34239 (MLS# A4704763) is a Single Family property with 3 bedrooms, 3 full bathrooms and 1 partial bathroom. 1585 South Drive is currently listed for $2,300,000 and was received on September 04, 2026. Want to learn more about 1585 South Drive? Do you have questions about finding other Single Family real estate for sale in Sarasota? You can browse all Sarasota real estate or contact a Coldwell Banker agent to request more information.

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