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Space to grow, room to gather, and a location that feels like home. Just blocks from Winchester’s town center, commuter rail, and nearby schools, this warm and distinctive home offers four levels of flexible living. A vaulted-ceiling living room sets the tone, while the custom kitchen features blue cabinetry, copper accents, and bold designer touches. One bedroom opens to a composite deck overlooking the fenced backyard—perfect for coffee while enjoying the view. The finished lower level adds space to work, host, or unwind. Updated systems and an attached two-car garage offer everyday ease. The sale is subject to a license to sell from the Probate and Family Court. Not an estate sale. Seller prefers up to two months of use and occupancy after closing. Property sold as is.
Current real estate data for Single Family in Winchester as of Oct 08, 2025
63
Single Family Listed
65
Avg DOM
550
Avg $ / SqFt
$2,267,389
Avg List Price

Property Details

Price:
$1,990,000
MLS #:
73396909
Status:
Active
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Jun 26, 2025
Finished Sq Ft:
4,474
Total Sq Ft:
4,474
Lot Size:
13,016 sqft / 0.30 acres (approx)
Year Built:
1959

Schools

Interior

Appliances
Gas Water Heater, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer, Range Hood
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Wall Unit(s), Heat Pump
Fireplaces Total
2
Flooring
Wood, Tile, Laminate, Flooring – Hardwood
Heating
Forced Air, Baseboard, Heat Pump, Natural Gas
Laundry Features
Flooring – Laminate, In Basement

Exterior

Architectural Style
Split Entry
Community Features
Public Transportation, Shopping, Public School
Exterior Features
Deck – Composite, Patio
Parking Features
Attached, Off Street
Parking Spots
2
Roof
Shingle

Financial

Tax Year
2025
Taxes
$19,392

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Property Summary

    4 Chestnut St Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,990,000 and features 4 beds, 5 baths, and has approximately 4,474 square feet of living space, and was originally constructed in 1959. The current price per square foot is $445. The average price per square foot for Single Family listings in Winchester is $550. The average listing price for Single Family in Winchester is $2,267,389. To schedule a showing of MLS#73396909 at 4 Chestnut St in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.

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CRP: Certified Relocation Professional
CRS: Certified Residential Specialist
GRI: Graduate of Realtors Institute
CBR: Certified Buyers Representative
BSBA: Bachelor of Science in Business Administration. Babson College 1979
MBA: Master of Business Administration. Babson College 2002

James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…

More About James
4 Chestnut St
Winchester, MA