Map location of 1739 CHEROKEE DRIVE, SARASOTA, FL 34239
$4,499,000
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1739 Cherokee Drive, Sarasota, FL 34239

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4 Beds
5 Baths
4,538 Sq Ft

Nestled along Cherokee Drive in the prestigious Cherokee Park neighborhood, this residence enjoys a premier setting on one of Sarasotas 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 homes U-shaped floor plan wraps around its showpiece, a 45-foot crystal-clear pool with integrated spa, creating a seamless indooroutdoor 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 homes 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 chefs 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 Sarasotas 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.

Listing By: Cole Collins - COLDWELL BANKER REALTY flmfr Realty.com
  • MLS# A4670822
  • Date Listed11/05/2025
  • Days on Realty 5 Days
  • Bedrooms 4
  • Bathrooms 4 Full baths, 1 Half baths
  • Lot Size 0.46 acres (20,000 sq. ft)
  • Sewer Public Sewer
  • Subdivision CHEROKEE PARK
  • Property Type Single Family
  • County Sarasota
  • Year Built 2009
  • Water Public
  • Square Feet 4,538 sq. ft
  • Price Per Sq. Ft $991.41

Interior Features

  • Appliances Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer
  • Flooring Tile, Wood
  • Cooling Central Air
  • Heating Electric

Exterior / Lot Features

  • Exterior Lighting, Storage, Guest House
  • Roof Metal
  • Lot Size Acres 0.46
  • Lot Size SQFT 20,000.00
  • Lot Features Paved

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.

Financial Considerations

  • Tax Amount $48,813
  • Terms Cash, Conventional, FHA, VA Loan

Nearby Schools

Source: School Digger

Ese Special Programs

Public • PK - 12 • Serves this home

2.84 mi

Distance

Wilkinson Elementary School

Public • PK - 5

3.62 mi

Distance

Children First

Public • PK - PK

4.23 mi

Distance

Gulf Gate Elementary School

Public • PK - 5

5.31 mi

Distance

Emma E. Booker Elementary School

Public • PK - 5

5.38 mi

Distance

Brentwood Elementary School

Public • PK - 5

5.81 mi

Distance

Gocio Elementary School

Public • PK - 5

6.08 mi

Distance

The Florida Center For Child And Family Development

Public • PK - PK

6.47 mi

Distance

Imagine School At Palmer Ranch

Public • PK - 8

6.88 mi

Distance

Fruitville Elementary School

Public • PK - 5

7.05 mi

Distance

Brookside Middle School

Public • 6 - 8 • Serves this home

1.58 mi

Distance

Sarasota School Of Arts/sciences

Public • 6 - 8

3.23 mi

Distance

Triad

Public • 6 - 12

3.62 mi

Distance

Suncoast School For Innovative Studies

Public • 6 - 8

5.24 mi

Distance

Mcintosh Middle School

Public • 6 - 8

5.39 mi

Distance

Booker Middle School

Public • 6 - 8

6.36 mi

Distance

Sarasota Middle School

Public • 6 - 8

6.45 mi

Distance

Sarasota High School

Public • 9 - 12 • Serves this home

1.29 mi

Distance

Riverview High School

Public • 9 - 12

3.12 mi

Distance

Sarasota Military Academy

Public • 9 - 12

3.23 mi

Distance

Suncoast Polytechnical High School

Public • 9 - 12

3.62 mi

Distance

Sarasota County Acceleration Academies

Public • 9 - 12

4.49 mi

Distance

Booker High School

Public • 9 - 12

5.23 mi

Distance

Elevation Preparatory Academy

Private • 06 - 12

1.81 mi

Distance

Brickhouse Academy

Private • 05 - 12

3.14 mi

Distance

West Coast School For Human Dev

Private • KG - 12

3.24 mi

Distance

Palm Grove Mennonite School

Private • KG - 12

3.36 mi

Distance

Agape Christian School Of Sarasota

Private • KG - 12

3.48 mi

Distance

Saltmeadow School

Private • 01 - 12

4.83 mi

Distance

Liberty Baptist Academy

Private • PK - 12

5.06 mi

Distance

Cardinal Mooney Catholic High School

Private • 09 - 12

5.15 mi

Distance

Shepherds Hill Christian School

Private • KG - 12

5.25 mi

Distance

Achievement Center

Private • 06 - 12

5.25 mi

Distance

Sales & Tax History

Source: Public Records

Population & Environment

Source: Sperling's Best Places

Walkability in FL / 34239

Source: Walkscore

12/100

Car-Dependent

Walk Score ®

39/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 37/100, Transit Score: 10/100, Bike Score: 51/100.

Points of Interest near 1739 CHEROKEE DRIVE, SARASOTA, FL 34239

Frequently Asked Questions for 1739 CHEROKEE DRIVE

Source: Realty.com

1739 CHEROKEE DRIVE, SARASOTA, FL 34239 is a Single Family 4,538 sq. ft. home listed for sale. Realty.com has 78 photos available of this 4 bed, 5 bath house, listed at $4,499,000. View sales and tax history, use our mortgage calculator and more on Realty.com

Realty.com has 78 photos of 1739 CHEROKEE DRIVE.

Our records indicate that 1739 CHEROKEE DRIVE was built in 2009.

The full address for this home is 1739 CHEROKEE DRIVE, SARASOTA, FL 34239.

1739 CHEROKEE DRIVE has been listed on Realty.com since Wed November 05, 2025

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 37/100, Transit Score: 10/100, Bike Score: 51/100.

There are 3 schools assigned to this home. Check out the schools near 1739 CHEROKEE DRIVE. Ese Special Programs (Grades: PK - 12), Brookside Middle School (Grades: 6 - 8), Sarasota High School (Grades: 9 - 12)

Listing provided courtesy of: Coldwell Banker Realty (tel: 941-366-8070)
Listing agent: Cole Collins (#281528140)

This content last refreshed on 2025-11-10 13:36:54. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Export listing data of 1739 CHEROKEE DRIVE, SARASOTA, FL 34239 : MLS# A4670822

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