1585 South Dr

Off Market

1585 South Dr

Sarasota FL 34239

3678 sq. ft.

16433 sq. ft.

Single-Family

Last sold for $2,200,000

Kelly Quigley, last sold this property on 16 October 2026 after 41 days on market.

Overview

Set on a beautiful corner lot in the highly sought-after Cherokee Park neighborhood, this charming two-story residence offers three bedrooms, three-and-a-half baths, and a rare opportunity to create a home tailored to your vision. Surrounded by a lush, expansive yard with ample room for a pool, the property offers exceptional flexibility for its next owner. Enjoy the home's timeless character as it is, or take advantage of the opportunity to create your dream home in one of Sarasota's most established neighborhoods. Inside, a light-filled, open floor plan is complemented by beautiful wood floors and an inviting sense of warmth throughout. The main level features a comfortable guest bedroom with an adjacent full bath, as well as a spacious en-suite primary bedroom, offering the ease and convenience of first-floor living. Upstairs, a private en-suite retreat is filled with character, featuring charming dormer windows, built-in window seats, and extensive storage. Adding to the property's remarkable potential is a recently approved variance along the side of the lot, providing an additional 10 feet of buildable envelope and expanding the possibilities for a future renovation, addition, or new residence. Ideally situated West of the Trail, this exceptional property places you close to top-rated schools, Sarasota Memorial Hospital, the shops and dining of Southside Village, the world-renowned beaches of Siesta Key, and vibrant downtown Sarasota. With its coveted location, generous homesite, and unique development potential, this Cherokee Park property presents an extraordinary opportunity to create something truly special.

Features

3 bedrooms

4 bathrooms

2 carspaces

2 garage spaces

3678 sq. ft. floor area

16433 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Sarasota over the last 12 months, the estimated median property value of 1585 South Dr is $595k.

Median value

$595k

Estimated value range

$187.5k - $3.7m

Median days on market

Estimated value trend

-5%

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 1585 South Dr

2026

Sold

$2,200,000

16 Oct 2026 by Kelly Quigley, of MICHAEL SAUNDERS & COMPANY

2025

Sold

$2,300,000

02 Dec 2025 by Nick Gard, of COLDWELL BANKER REALTY

2022

Sold

$2,100,000

25 Oct 2022 by Peter Laughlin, of PREMIER SOTHEBYS INTL REALTY

Happy sellers in Sarasota

86%

86% 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 7 reviews in Sarasota over the last 12 months.

Local market activity for 3 bedroom single-family properties in Sarasota

In the last 12 months, 143 three-bedroom single-family properties similar to 1585 South Dr, have been sold.

This represents a 2% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Sarasota for a market analysis.

Roberta Tengerdy PA and Carolyn Barker Collins PA

at Premier Sotheby's International Realty

(167 reviews)

Get a market analysis

Angela Adams

at MICHAEL SAUNDERS & COMPANY

(52 reviews)

Get a market analysis

Monika White

at Dalton Wade | Florida

(18 reviews)

Get a market analysis

Kerry Langman

at Coldwell Banker Realty - Lakewood Ranch

(60 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Sarasota

Roberta Tengerdy PA and Carolyn Barker Collins PA

Sellers who recommend Roberta Tengerdy PA and Carolyn Barker Collins PA have praised them for being local expert, responsive, clear communication, supportive, friendly, reliable, and detail-oriented

5 (167 reviews)
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Angela Adams

Sellers who recommend Angela Adams have praised them for being local expert, clear communication, supportive, detail-oriented, reliable, dedicated, and empathetic

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Monika White

Sellers who recommend Monika White have praised them for being local expert, clear communication, great negotiation, and reliable

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Kerry Langman

Sellers who recommend Kerry Langman have praised them for being local expert, reliable, clear communication, responsive, dedicated, well-prepared, and honest