1 Overlook Way Winchester, MA $ 1,850,000
1 Overlook Way
$ 1,850,000
Recently Listed
Open House 10/2 12pm - 1:30pm
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1 Overlook Way

Winchester, MA, 01890
$ 1,850,000
Bedrooms4 Baths2.1 Sq 3,092

Monthly Estimate*

$ 11,681

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Single Family Home for sale in Winchester, MA

for $1,850,000 with 4 bedrooms and 2 full baths, 1 half bath. This 3,092 square foot home was built in 1941 on a lot size of 0.36.

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.

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Open House

10/2/2026 12:00 PM - 1:30 PM
10/3/2026 12:00 PM - 1:30 PM
10/4/2026 12:00 PM - 1:30 PM
1 Overlook Way Winchester, MA
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 1,850,000

Bedrooms

4

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 17,650

Style

Colonial

Lot Size

0.36

Year Built

1941

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73581571

List By
Lynne Russo

Listing Agent

Better Homes And Gardens Real Estate - The Shanahan Group

Broker

Affordability Calculator

$13,152
Per Month
89%
11%
0%
Monthly Principal & Interest
$11,681
Monthly Property Taxes
$1,471
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Pricing History
DatePricePrice ChangeDescription
9/23/2026$1,850,000 Listed Price

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1 Overlook Way, Winchester, MA, 01890 is a Single Family Home for sale at $1,850,000 with 3,092 sqft and a lot size of 0.36. 1 Overlook Way has 4 bedrooms, 2.1 baths, and was built in 1941. The property's zip code is 01890 which is in Winchester, MA