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1729 CHEROKEE DRIVE SARASOTA FL 34239

$4,450,000
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1729 CHEROKEE DRIVE, SARASOTA, FL 34239 - MLS#MFRA4682051 1729 CHEROKEE DRIVE, SARASOTA, FL 34239 - MLS#MFRA4682051 1729 CHEROKEE DRIVE, SARASOTA, FL 34239 - MLS#MFRA4682051 1729 CHEROKEE DRIVE, SARASOTA, FL 34239 - MLS#MFRA4682051

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 1729 Cherokee Dr

4 Bedrooms
4/1 Bathrooms
3 Car Garage
5,995 Square Feet
4,353SF Living Area
Pool:
Yes
Water: None
Year Built 2008
Listed For 1 Days

Don't miss this home for sale in Cherokee Park! 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.

This luxury single family home was built in 2008 and features 4 bedrooms, and 4 full bathrooms plus 1 half bath. This home for sale is 5,995 square feet, with 4,353 sq ft being air conditioned living space. The home has a 3 car garage and has a private swimming pool.

Directions to this property are as follows: From S Osprey Ave, Turn Onto Cherokee Dr And House Will Be On The Right Side.

Please contact your ZFC agent for more information about MLS# MFRA4682051 or any other homes for sale in Sarasota or elsewhere in the Sarasota County area.

Features & Amenities

Appliances

Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer, Water Purifier, Water Softener

Other Equipment

Irrigation Equipment, Private Entrance, Private Yard, Generator

Architecture

Custom

Cooling

Central Air, Mini-Split Unit(s)

Heating

Central, Electric, Zoned

Flooring

Ceramic Tile, Hardwood, Other

Parking

Driveway, Garage Door Opener, Oversized

Lot Size

20000

View

Trees/Woods view

Construction Materials

Block, Stucco

Security Features

Security System, Smoke Detector(s)

Interior Features

Built-in Features, Ceiling Fans(s), High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments

Furnished

Unfurnished

Exterior Features

Balcony, Courtyard, French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Yard, Rain Gutters

Lot Features

City Limits, Landscaped, Near Public Transit, Oversized Lot, Private, Sidewalk, Paved

Property Condition

Completed

Patio And Porch Features

Covered, Patio, Porch, Screened

Pool Features

Heated, In Ground, Lighting, Tile

Roof

Concrete, Tile

Window Features

Window Treatments

Utilities

Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sprinkler Well, Water Connected

Laundry

Inside, Laundry Room

Fencing

Fenced

Fireplace

Gas, Living Room, Outside, Wood Burning

Spa Features

Heated, In Ground

Zoning

R S F1

Year Built

2008

Pets Allowed

Yes

Annual Real Estate Taxes

$24,981 (2025)

Legal Description

W 1/2 Of Lot 4, Blk F, Cherokee Park

Property Type

Single Family Home

Community Features

Street Lights

Direction Faces

South

MLS Number

MFRA4682051

Universal Property Id

U S-12115-N-2039020033-R-N

Days On Market

1

Community Name

Cherokee Park 2

1729 Cherokee Dr Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 1729 Cherokee Dr should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $24,981 but will likely change when this home sells. These estimations are calculated from a list price of $4,450,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 1729 Cherokee Dr

Address Sale Price Bed Bth Size Location Sale Date
No comps found for this property

MLS# MFRA4682051 Listing History

02/10/2026 Listed for sale by MICHAEL SAUNDERS & COMPANY with MLS# MFRA4682051 with a list price of $4,450,000.

Sarasota County Schools

Elementary School

Middle School

High School

Public Transportation

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

Breeze Transit:

Sarasota/US-41/Venice

Breeze Transit:

Sarasota/US-41/Venice

Breeze Transit:

77 Siesta Islander

This listing of 1729 Cherokee Dr Sarasota FL 34239 was last updated on 2026-02-25 06:33:27. Listing courtesy of MICHAEL SAUNDERS & COMPANY.
MLS

Map of 1729 Cherokee Dr Sarasota FL 34239

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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