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Back 1729 Cherokee Drive
Off Market

1729 Cherokee Drive

Sarasota FL 34239

4
5
3
5995 sq. ft.
20000 sq. ft.
Single-Family
Last sold for $3,881,000
Kim OgilvieKim Ogilvie, last sold this property on 28 April 2026 after 74 days on market.

Overview

Priced to sell. 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.

Features

4 bedrooms
5 bathrooms
3 carspaces
3 garage spaces
5995 sq. ft. floor area
20000 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Sarasota over the last 12 months, the estimated median property value of 1729 Cherokee Drive is $1.67m.

Median value
$1.67m
Estimated value range
$300k - $9.5m
Median days on market
58
Estimated value trend
-19%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Sarasota. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1729 Cherokee Drive

2026
Sold
$3,881,000
28 Apr 2026 by Kim Ogilvie, of MICHAEL SAUNDERS & COMPANY
2010
Sold
$1,800,000
19 Feb 2010 by Nora Johnson, of MICHAEL SAUNDERS & COMPANY
2004
Sold
$1,299,000
01 Sep 2004 by Phyllis Garfinkel, of MICHAEL SAUNDERS & COMPANY

Happy sellers in Sarasota

90%
90% of sellers in Sarasota reported that their sale price either exceeded or met their price expectations.

Sarasota stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 10 reviews in Sarasota over the last 12 months.

Local market activity for 4 bedroom single-family properties in Sarasota

In the last 12 months, 68 four-bedroom single-family properties similar to 1729 Cherokee Drive, have been sold.

This represents a 25% decrease in four-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

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Roberta Tengerdy PA and Carolyn Barker Collins PA

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Angela Adams

Angela Adams is a recommended agent for Sarasota.  They have 2 local sales and collected 2 local reviews across the last 12 months.

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Monika White

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Kerry Langman

Sellers who recommend Kerry Langman have praised them for being local expert, reliable, responsive, clear communication, trustworthy, easy to work with, and pleasant

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