143 Overbrook Drive
Stamford, CT, 06906 $ 995,000
Bedrooms4 Baths3.1 Sq 2,744 Monthly Estimate*
$ 6,208
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***
See more
FeaturesGeneralZoning 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
See more
InteriorCooling System Central Air Zoned
Total Rooms 9
Basement Description Full Unfinished
See more
ExteriorWater Source Public Water Connected
Lot Description Level Lot
See more
* Excluded FeaturesList ByJonathan MakovskyListing Agent
Compass Connecticut, LlcBroker
jonathan.makovsky@compass.comEmail
Affordability Calculator
- 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.
Learn more about how to save NearbySingle family listings in Stamford, CT
Average List Price $1,169,512
Percent of Sale Price 18%
About Stamford, CT 133,887 Population
14% Since 2002
$ 87,025 Median Income
39.84 Median Age
29% Households with Children
Trends Information provided by ATTOM Data Solutions.
3041891 Elementary School
4780598 Middle School
Stamford High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 10/10/2025 | $995,000 | | Listed Price |