143 Overbrook Drive Stamford, CT $ 995,000
143 Overbrook Drive
$ 995,000
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143 Overbrook Drive

Stamford, CT, 06906
$ 995,000
Bedrooms4 Baths3.1 Sq 2,744

Monthly Estimate*

$ 6,208

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Single Family Home for sale in Stamford, CT

for $995,000 with 4 bedrooms and 3 full baths, 1 half bath. This 2,744 square foot home was built in 1924 on a lot size of 0.6.

***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. ***FINAL OFFERS by 10/20 @8p***

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Single Family Contingent

Price

$ 995,000

Bedrooms

4

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 12,925

Style

Lot Size

0.6

Year Built

1924

Town/City

Stamford

MLS | Web ID

24132263

Features
General
Zoning R20
Neighborhood Glenbrook
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Under Contract
Acres 0.6
Directions Toms road to Overbrook drive house at end of street on right
High School Stamford
City Stamford
Elementary School Toquam Magnet
Sq Ft Total 2744
DOM 13
Year Built 1924
Style Cape Cod
Year Built Source Public Records
Association Fee Includes Road Maintenance
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Interior
Cooling System Central Air Zoned
Total Rooms 9
Basement Description Full Unfinished
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Exterior
Water Source Public Water Connected
Lot Description Level Lot
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* Excluded Features
List By
Jonathan Makovsky

Listing Agent

Compass Connecticut, Llc

Broker

jonathan.makovsky@compass.com

Email

Affordability Calculator

$7,285
Per Month
85%
15%
0%
Monthly Principal & Interest
$6,208
Monthly Property Taxes
$1,077
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3041891 Elementary School
4780598 Middle School
Stamford High School High School
Pricing History
DatePricePrice ChangeDescription
10/10/2025$995,000 Listed Price

Map


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143 Overbrook Drive, Stamford, CT, 06906 is a Single Family Home for sale at $995,000 with 2,744 sqft and a lot size of 0.6. 143 Overbrook Drive has 4 bedrooms, 3.1 baths, and was built in 1924. The property's zip code is 06906 which is in Stamford, CT