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$1,100,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,744 Sq. Ft.
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***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.

Full Property Details for 143 Overbrook Dr

General

  • Sold For: $1,100,000
  • HOA FEE: $42/month
  • HOA FEE FREQ.: Annually
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24132263
  • Added to Site: 98 day(s) ago

Interior

  • Number of Rooms: 9
  • Interior Features: Security System
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Dressing Room, Full Bath, Hardwood Floor, Wide Board Floor, Upper
  • Bedroom 1: Bedroom - Full Bath, Wide Board Floor, Main
  • Bedroom 2: Bedroom - Wide Board Floor, Upper
  • Bedroom 3: Bedroom - Wide Board Floor, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, Wide Board Floor, Main
  • Dining Room: Dining Room - Hardwood Floor, Wide Board Floor, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Shed, Porch, Deck, Gutters
  • Color: White

Parking

  • Parking: None

Location

  • County: Fairfield
  • Neighborhood: Glenbrook
  • Driving Directions: Toms road to Overbrook drive, house at end of street on right

School Information

  • Elementary School: Toquam Magnet
  • High School: Stamford

Community

  • Community Name: Glenbrook
  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Road Maintenance

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Tank Size Unknown

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Cape Cod
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Wood
  • Basement Desc.: Full, Unfinished
  • Roof: Asphalt Shingle
  • Square Feet: 2,744
  • Above Ground: 2,744 Sq. Ft.
  • Year Built: 1924

Lot Features

  • Lot Size (Acres): 0.6
  • Zoning: R20
  • Lot Description: Level Lot

Financial Considerations

  • Association Fee: $500
  • Assoc Fee Freq.: Annually
  • Assessment Amount: $546,270
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 315661

Listed by Compass Connecticut, LLC, JMX TEAM AT COMPASS, Jonathan Makovsky
Sold by Keller Williams Prestige Prop., Dober Team at Keller Williams Realty, Brian Barran

Listing agent

— 143 Overbrook Dr —

  • Jonathan Makovsky

    Compass Connecticut, LLC

Agent Contact: (203) 548-7339 Office Contact: (203) 309-6712

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 143 Overbrook Dr

School District:Stamford School District
NameGradesDistance
Toquam Magnet School
123 Ridgewood Ave., Stamford, CT 06907
K-50.2 mi
Dolan School
51 Toms Road, Stamford, CT 06906
6-80.3 mi
Stamford High School
55 Strawberry Hill Avenue, Stamford, CT 06902
9-121.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 143 Overbrook Dr

Date
Details
Price
Change
Source
12/11/2025
Sold
$1,100,000
10.55%
MLS
10/16/2025
Listed
$995,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Compass Connecticut, LLC, JMX TEAM AT COMPASS, Jonathan Makovsky
Sold by Keller Williams Prestige Prop., Dober Team at Keller Williams Realty, Brian Barran

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143 Overbrook Drive, Stamford, CT 06906 (MLS# 24132263) is a Single Family property that was sold at $1,100,000 on December 11, 2025. Want to learn more about 143 Overbrook Drive? Do you have questions about finding other Single Family real estate for sale in Stamford? You can browse all Stamford real estate or contact a Coldwell Banker agent to request more information.