Stamford, CT / SOLD

143 Overbrook DriveStamford, CT 06906

The buyer could have saved $8,250 in brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

See how the commission rebate works ↗

*Estimate assumes a 2.5% buyer-agent commission and a 30% rebate. Actual savings depend on final purchase price and commission received. Based on the recorded closed price; this is a hypothetical estimate, not a statement of actual commission or rebate paid.

Sale Price$1,100,000ClosedDecember 10, 2025

Our Take

143 Overbrook Drive is an expanded 1920s Cape with a front porch, living room with vintage charm, formal dining room, updated kitchen, and family room. The first floor includes an en-suite bedroom, powder room, mudroom, and laundry room. Upstairs are a primary suite with changing room, a bedroom with its own fireplace, and a third bedroom with flexible guest or office use. Outside, the flat half-acre yard is open and private, with a detached garage. City water, sewer, gas, ductless air conditioning, and a waterproofed basement add practical infrastructure.

143 Overbrook Drive — exterior photo
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Estimated buyer rebate

The buyer could have saved $8,250 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

See how the commission rebate works ↗

*Estimate assumes a 2.5% buyer-agent commission and a 30% rebate. Actual savings depend on final purchase price and commission received. Based on the recorded closed price; this is a hypothetical estimate, not a statement of actual commission or rebate paid.

At a glance

Closed · MLS #24132263
Bedrooms
4
BathroomsBaths
3 full / 1 half
Square feet
2,744
Year built
1924
Acres
0.6
Property taxes
$12,925

July 2025-June 2026

What stands out

  • Front porch honoring the home’s history
  • First-floor en-suite bedroom
  • Primary suite with changing room
  • Second bedroom with its own fireplace
  • Flat, open, private half-acre yard
  • Detached garage
  • Ductless air conditioning
  • Waterproofed basement by CT Basement Systems
Read the full listing description

***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.

Schools

Elementary
Toquam Magnet
Middle
Not provided
High
Stamford

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

Price history

DateEventPrice
Closed price$1,100,000
Original list price$995,000

Intermediate price changes and previous listings may not be included.

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Nearby sold homes

Closest recorded sales

*Estimate: $1,100,000 closed price × assumed 2.5% buyer-agent commission × 30% rebate = $8,250. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered or actual compensation. This is a hypothetical estimate, not a rebate paid on this sale.

Listed by Compass Connecticut, LLC · (203) 309-6712

Jonathan Makovsky

SmartMLS · Listing #24132263 · Closed

Listing data checked: Sep 26, 2026, 11:54 AM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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