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143 Overbrook DriveStamford, CT 06906

For Sale

$995,000

Smart Buyer Rebate $9,950

***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.

Listed by Jonathan Makovsky

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Compass Connecticut, LLC

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(203) 548-7339

Last updated October 20, 2025

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Source: SmartMLS #24132263

Listing Facts

  • TypeSingle-family
  • NeighborhoodSpringdale
  • Bedrooms4
  • Bathrooms4
  • Days on Prevu11
  • HOA/Maint. Fees$500/annual
  • Taxes$12,925/year
  • Size2,744 sqft
  • Price per sqft$363

Location

Mortgage Calculator

Listing History

10/17/2025
Status changed to Active
$995,000
10/16/2025
Status changed to Removed from Feed
$995,000
10/10/2025
Listed by Compass Connecticut, LLC
$995,000

Property Details for 143 Overbrook Drive

Association

Fees

  • Association Fee Includes: Road Maintenance

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1924
  • Year Built Details: Public Records
  • Architectural Style: Cape Cod
  • Construction Materials: Frame
  • Exterior Features: Shed, Porch, Deck, Gutters

Features

  • Waterfront Features: Not Applicable

Measurements

  • Lot Features: Level Lot
  • Lot Size Acres: 0.60

Financial

Taxes

  • Parcel Number: 315661
  • Tax Annual Amount: $12,925.00
  • Tax Year: 25

Interior

Features

  • Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Fireplaces Total: 2
  • Interior Features: SECURESY

Measurements

  • Living Area: 2,744

Rooms

  • Basement: Full, Unfinished
  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 4
  • Rooms Total: 9

Schools

Elementary School

  • Elementary School: Toquam Magnet

High School

  • High School: Stamford

Utilities

Equipment

  • Cooling: Central Air, Zoned
  • Heating: Hot Water
  • Laundry Features: Main Level
  • Sewer: Public Sewer Connected
  • Water Source: Public Water Connected

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Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.