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$4,499,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,538 Sq. Ft.
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Under contract-accepting backup offers. Nestled along Cherokee Drive in the prestigious Cherokee Park neighborhood, this residence enjoys a premier setting on one of Sarasota's most sought-after streets, renowned for its graceful oak canopy and classic west-of-the-trail charm. This residence embodies the perfect balance of modern architecture, natural materials, and tranquil privacy. Designed by award-winning architect Guy Peterson and constructed by master builder Pat Ball, the home delivers a rare combination of architectural pedigree and enduring craftsmanship. Positioned on a gracious, estate-sized parcel surrounded by lush greenery, the home's U-shaped floor plan wraps around its showpiece, a 45-foot crystal-clear pool with integrated spa, creating a seamless indoor-outdoor living experience that defines the Sarasota lifestyle. Outside, the stone pathway leading to the custom mahogany front door sets a striking geometric tone. Inside, board-on-board architectural molded concrete accent walls, Santos Mahogany wood floors, and cypress-accent ceilings strike a natural harmony with the home's sleek, modern lines. Floor-to-ceiling impact-rated Marvin windows flood the interior with light, framing tranquil views of the pool and landscape from nearly every room. The wide-open living and dining area, anchored by a wood-burning fireplace, sets the tone for elegant yet effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, extensive custom maple cabinetry, and a seamless connection to both indoor and outdoor dining spaces. In the west wing, the expansive primary suite serves as a private retreat with walls of glass overlooking the grounds, complemented by an adjacent executive office for work-from-home convenience. The east wing hosts two en-suite guest bedrooms, each with sliding glass doors opening directly to the pool. A detached guest cabana offers a complete living area, kitchenette, and en-suite bedroom that is ideal for visitors, extended stays, or use as a private art studio or executive home office. Located within Cherokee Park, one of Sarasota's most established and beloved neighborhoods, this home offers walking distance to Southside Elementary, minutes to Southside Village and downtown Sarasota, and easy access to Siesta Key Beach, just five streets away. The community is known for its family-friendly gatherings, tree-lined streets, and timeless Sarasota character.

Full Property Details for 1739 Cherokee Dr

General

  • Price: $4,499,000
  • Taxes: $48,813 (2024)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4670822
  • Updated: 2/13/2026
  • Added to Site: 144 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 5
  • Interior Features: Built-in Features, Ceiling Fan(s), Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Thermostat, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Wood Burning
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Water Filtration System
  • Furnishings: Unfurnished
  • Flooring: Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Heated, In Ground, Lighting
  • Spa: Yes
  • Spa Description: Heated
  • Security/Safety: Security System, Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System, Lighting, Private Mailbox, Sliding Doors, Storage
  • Deck/Patio: Covered, Deck, Patio
  • Porch/Patio/Deck: Covered, Deck, Patio

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: From Downtown Sarasota, head south on Osprey Avenue. Turn right onto Cherokee Drive, 1739 Cherokee Drive is located midway down the street on the right-hand side.
  • Direction Faces: South

School Information

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

Community

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

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Custom
  • Architectural Style: Custom
  • Builder: Pat Ball
  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Metal
  • Windows: Storm Window(s), Shutters, Wood Frames
  • Stories/Levels: One
  • Square Feet: 4,538
  • Sq. Ft. Source: Public Records
  • Year Built: 2009

Additional Structures

  • Other Structures: Guest House

Lot Features

  • Property View: Pool
  • Lot Size (Acres): 0.46
  • Lot Size (Sq. Ft.): 20,000
  • Lot Size: 20000
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Financial Considerations

  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Optional
  • Tax Amount: $48,813
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: E 1/2 OF LOT 4, BLK F, CHEROKEE PARK
  • Flood Zone Info: X
  • APN: 2039020031
  • Property ID: 2039020031
  • Block/Lot/Section: F
Buyer's Brokerage Compensation: Contact Listing Agent
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— 1739 Cherokee Dr —

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NMLS#: 1598647

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Schools serving 1739 Cherokee Dr

School District:Sarasota County School District
NameGradesDistance
Southside Elementary School, Sarasota, FL
1901 Webber Street, Sarasota, FL 34239
PK-50.2 mi
Brookside Middle School
3636 South Shade Avenue, Sarasota, FL 34239
6-80.8 mi
Sarasota High School
2155 Bahia Vista Street, Sarasota, FL 34239
9-121.2 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 1739 Cherokee Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/05/2025
Listed
$4,499,000
7.41%
MLS
9/13/2023
Sold
$4,188,500
—
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 1739 Cherokee Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$37,401
-23%
$2,553,400
-22%
2024
$48,813
180%
$3,279,500
180%
2023
$17,413
3%
$1,170,260
3%
2022
$16,979
—
$1,136,175
3%
2021
$17,030
—
$1,103,083
1%
2021
$17,030
1%
$1,087,853
2%
2019
$16,796
2%
$1,063,395
2%
2018
$16,530
1%
$1,043,567
2%
2017
$16,344
—
$1,022,103
2%
2016
$16,307
3%
$1,001,080
5%
2015
$15,899
—
$955,124
1%
2014
$15,887
—
$947,544
1%
2013
$15,859
—
$933,541
—
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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1739 Cherokee Drive, Sarasota, FL 34239 (MLS# A4670822) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 1739 Cherokee Drive is currently listed for $4,499,000 and was received on November 05, 2025. This property is listed by Cole Collins from our Siesta Key Office.Want to learn more about 1739 Cherokee 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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