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$4,450,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,353 Sq. Ft.
  • Updated 20 hours ago
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Recipient of eleven awards, including Residential Design and Build Design Excellence and Home of the Year by SRQ Magazine, this exceptional residence is the result of a thoughtful collaboration between Jonathan Parks Architect and Michael A. Gilkey Inc landscape designer. Located in one of Sarasota's oldest and most established neighborhoods, the home seamlessly blends a traditional 1920s architectural vocabulary with a modern appreciation for simplicity and precision. The result is a sophisticated four-bedroom residence with a British Colonial sensibility-elegant, timeless, and thoughtfully designed for today's lifestyle. Set on an unusually large 20,000-square-foot lot and located outside of any flood zone, the property offers a rare sense of space and privacy. An artistic pool and a series of designated outdoor living areas, framed by curated garden vignettes, complete this tranquil retreat. The striking foyer welcomes you with understated elegance, gleaming wood floors, and an immediate sense of refinement. Walls of glass define the main living spaces, filling the interior with natural light and highlighting the fireplace as a focal point. While the classic elements of a traditional home remain-stucco exterior, white roof, and ironwork details-the overall aesthetic is contemporary and quietly confident. Large windows and an open floor plan are designed to maximize light and create a seamless connection to the outdoors. A spacious screened patio offers an inviting setting for both relaxation and al fresco dining. Mature Mahoe trees, native to South Africa, line the exterior and rise gracefully to the level of the home's high windows, enhancing privacy and serenity. The primary suite occupies its own private wing on the first floor, complete with a secluded courtyard, while an ensuite guest bedroom and office balance the opposite wing. Upstairs, two additional ensuite bedrooms each enjoy private balconies overlooking the lush grounds. Throughout the home, a Zen-like sense of peace and tranquility prevails-a true sanctuary of thoughtful design and quiet luxury.

Full Property Details for 1729 Cherokee Dr

General

  • Price: $4,450,000
  • Taxes: $24,980 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4682051
  • Updated: 2/13/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: 1 Month

Interior

  • Number of Rooms: 11
  • Interior Features: Built-in Features, Ceiling Fan(s), High Ceilings, Kitchen and Family Room Combination, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Gas, Living Room, Outside, Wood Burning
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer, Water Purifier, Water Softener
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Engineered Hardwood, Other

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

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

Exterior

  • Exterior Features: Balcony, Courtyard, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Yard, Rain Gutters
  • Deck/Patio: Covered, Patio, Porch, Screened
  • Porch/Patio/Deck: Covered, Patio, Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: Driveway, Garage Door Opener, Oversized

Location

  • Area: 34239 - Sarasota/Pinecraft
  • County: Sarasota
  • Development Name: 34239 - Sarasota/Pinecraft
  • Subdivision: CHEROKEE PARK 2
  • Driving Directions: From S Osprey Ave, turn onto Cherokee Dr and house will be on the right side.
  • Direction Faces: South

School Information

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

Community

  • Community Name: 34239 - Sarasota/Pinecraft
  • Number of Pets: 10

Heating & Cooling

  • Cooling Type: Central Air, Mini-Split Unit(s)
  • Heating Type: Central, Electric, Zoned

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sprinkler Well, Street Lights, Water Connected

Structural Information

  • Architectural Info: Custom
  • Architectural Style: Custom
  • Exterior Const.: Block, Stucco
  • Roof: Concrete, Tile
  • Windows: Window Treatments
  • Stories/Levels: Two
  • Square Feet: 4,353
  • Sq. Ft. Source: Public Records
  • Year Built: 2008

Lot Features

  • Property View: Trees/Woods
  • Lot Size (Acres): 0.46
  • Lot Size (Sq. Ft.): 20,000
  • Lot Size: 20000
  • Frontage: Street Paved
  • Street/Road Desc.: Paved
  • Fencing (Description): Fenced

Financial Considerations

  • Tax Amount: $24,980.69
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: W 1/2 OF LOT 4, BLK F, CHEROKEE PARK
  • Flood Zone Info: X
  • APN: 2039020033
  • Property ID: 2039020033
  • Block/Lot/Section: F

Listed by Michael Saunders & Company

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Listing agents

— 1729 Cherokee Dr —

  • Michael Saunders & Company

  • 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 1729 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 Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1729 Cherokee Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/12/2026
Listed
$4,450,000
147.22%
MLS
2/19/2010
Sold
$1,800,000
—
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 1729 Cherokee Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$24,172
1%
$1,664,391
3%
2024
$23,890
3%
$1,617,484
3%
2023
$23,262
2%
$1,570,373
3%
2022
$22,713
-1%
$1,524,634
3%
2021
$22,835
—
$1,476,441
1%
2021
$22,835
1%
$1,456,056
2%
2019
$22,530
2%
$1,423,320
2%
2018
$22,175
1%
$1,396,781
2%
2017
$21,927
—
$1,368,052
2%
2016
$21,864
-1%
$1,339,914
1%
2015
$22,196
-1%
$1,330,600
—
2014
$22,350
—
$1,330,056
2%
2013
$22,314
—
$1,310,400
—
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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Listed by Michael Saunders & Company

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1729 Cherokee Drive, Sarasota, FL 34239 (MLS# A4682051) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 1729 Cherokee Drive is currently listed for $4,450,000 and was received on February 12, 2026. Want to learn more about 1729 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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