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For Sale

1 Overlook Way

Winchester, MA

$1,850,000

4 bd/2.5 ba/3,092 sf

Courtesy of Better Homes and Gardens Real Estate - The Shanahan Group

This home is listed by another brokerage. We can arrange a viewing, and we can represent you as the buyer.

The listing brokerage last updated this record on October 5, 2026.

Photographs

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41 photographs from the listing brokerage, shown as they published them.

About this home

Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen also opens naturally into the cozy family room - with gas fireplace, custom built-ins and access to the back and side yard, the family room will be well utilized! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a home office or storage. The finished lower level adds even more usable space, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

The details

Property type
Single family
Bedrooms
4
Bathrooms
2.5
Interior
3,092 sq ft
Lot
0.36 acres
Year built
1941
Price per sq ft
$598
County
Middlesex
Taxes
$17,650 (2026)
Heating
Central · Baseboard · Natural Gas · Ductless · Fireplace
Cooling
Ductless
Basement
Full · Partially Finished · Interior Entry · Bulkhead · Sump Pump · Concrete
Parking
6 (2 garage)
Fireplaces
3
Roof
Shingle
Sewer
Public Sewer
Water
Public
Zoning
RDA
Elementary school
Ambrose
Middle school
Mccall
High school
Whs
Days on market
12
MLS #
73581571

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