1. Connecticut
2. Stamford
3. 143 Overbrook Drive

143 Overbrook Drive, Stamford, CT 06906

• 4 beds |
• 4 baths |
• 2,744 sqft

Property Description

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.

Listing Status:

Coming Soon

Date Added:

October 10, 2025 at 10:49PM

Listing Office:

Compass Connecticut, LLC : (203) 309-6712

Listing Agent:

Jonathan Makovsky : (203) 548-7339

MLS ID:

24132263

Interior

• General: Security System
• Appliances: Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
• Laundry: Main Level
• Basement: FullUnfinished
• A/C: Central AirZoned
• Heating: Hot WaterOil
• Fireplace: Fireplaces: 2

Exterior

• General: ShedPorchDeckGutters
• Style: Cape Cod

Construction

• Roofing: Asphalt Shingle

Location

• HOA Amenities: Road Maintenance150.0Monthly
• County: Fairfield

Lot

• Zoning: R20315661

Utilities

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

This listing courtesy of Jonathan Makovsky, Compass Connecticut, LLC