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

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
Ask us about this home
Tell us when you could see it. We will confirm it is still available, book the viewing and go with you.























