Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
4 Beds
3 Baths
3,092 sqft

$1,850,000

1 Overlook Way, Winchester MA, 01890

Price per sqft$598.32
Built in1941
Property size3,092 sqft
Property typeResidential

Overview

Active

Listed Sep 23, 2026

Updated 6h ago

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.

$12,308/mo

Est. mortgage payment based on a $1,850,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
73581571

Interior Features

Bedrooms
4
Bathrooms
3
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.36 Acres

Other Property Details

Taxes
$17,650
Tax Frequency
Annually
Garage
Yes
55+/Senior Community
No

This listing is provided by Lynne Russo with Better Homes and Gardens Real Estate - The Shanahan Group

The property listing data and images displayed herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors, and public records, and compiled by MLS Property Information Network, Inc. This information is intended solely for the personal, non-commercial use of consumers who have a genuine interest in purchasing or leasing listed properties. It may not be used for any purpose other than to identify prospective properties of interest.

MLS Property Information Network, Inc. and its subscribers make no representations or warranties regarding the accuracy of the listing data or images presented.

©2026 MLS Property Information Network, Inc. All rights reserved.

Data last updated 4:27 PM UTC, 9/29/2026

Powered by Luxury Presence