143 Overbrook Drive

Stamford CT 06906

2744 sq. ft.

0.6 ac.

Single-Family

Last sold for $1,100,000

Jonathan Makovsky, last sold this property on 11 December 2025 after 56 days on market.

Overview

***FINAL OFFERS by 10/20 @8p*** Living in another time with all the modern features of 2025, 143 Overbrook Drive is an expanded 1920s cape on one of Stamford's most special hidden streets, an oasis near Glenbrook Station, downtown, and both I-95 and the Merritt Parkway. You can walk to coffee shops, gyms, and more yet feel worlds away once you turn down this quiet, dead-end enclave at the end of the street. The home's front porch feels like a snapshot from another era, setting the tone for a home that honors its history yet feels entirely today. Inside, you'll find a living room with vintage charm, a formal dining room, updated kitchen, family room, first-floor en-suite bedroom, powder room, and practical modern must-haves like a mudroom and laundry room. Upstairs, the primary suite includes a changing room, the second bedroom has its own fireplace, and the third bedroom offers flexible space for guests or office. The flat half-acre yard is open, private, and beautifully maintained, with a detached garage completing the picture. Modern living is fully built in with city water, sewer, and gas, ductless air conditioning, and a waterproofed basement by CT Basement Systems. With nothing left to do but move in, 143 Overbrook Drive is the best of Stamford's past and present, offering timeless character with today's convenience.

Features

4 bedrooms

4 bathrooms

2744 sq. ft. floor area

0.6 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Stamford over the last 12 months, the estimated median property value of 143 Overbrook Drive is $750k.

Median value

$750k

Estimated value range

$580k - $1.1m

Median days on market

Estimated value trend

-12%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Stamford. 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 143 Overbrook Drive

2025

Sold

$1,100,000

11 Dec 2025 by Jonathan Makovsky, of Compass Connecticut, LLC

2016

Sold

$700,000

26 Feb 2016 by Peter Joyce, of Sotheby's International Realty

Happy sellers in Stamford

We have insufficient information to provide an overview of customer satisfaction for Stamford. Viewing the agent profiles, reviews and sales for Stamford can provide insights for this location.