143 Overbrook Drive, Stamford, Connecticut

$995,000

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4

Beds

4

Baths

2,744

Square feet

0.60

Acres

About 143 Overbrook Drive

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.

Features of 143 Overbrook Drive

MLS® # 24132263
Price $995,000
Bedrooms 4
Bathrooms 4.00
Full Baths 3
Half Baths 1
Square Footage 2,744
Acres 0.60
Type Single Family For Sale
Style Cape Cod
Status Active

Community Information

Address 143 Overbrook Drive
Area Glenbrook
City Stamford
County Fairfield
State Connecticut
Zip Code 06906

Amenities

Parking None
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Interior Features Security System
Appliances Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Water, Oil
Cooling Central Air, Zoned
Fireplace Yes
# of Fireplaces 2
Has Basement Yes
Basement Full, Unfinished

Exterior

Exterior Clapboard, Wood
Exterior Features Shed, Porch, Deck, Gutters
Lot Description Level Lot
Roof Asphalt Shingle
Foundation Block, Concrete

School Information

Elementary Toquam Magnet
High Stamford

Additional Information

Date Listed October 10th, 2025
Days on Market 1
Zoning R20
RE / Bank Owned No
HOA Fees 500
HOA Fees Freq. Annually

Listing Details

OfficeCompass Connecticut, LLC

Listing Map

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Listing information last updated on October 18th, 2025 at 10:04am EDT.