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$1,850,000
Monthly Est:$9,208
4 Beds
- 3 Baths
2 full baths + 1 half bath
3,092sqft
1 Overlook Way, Winchester, MA 01890
$1,850,000
$9,208/moEst:
Get Pre-Approved
Single Family Residence
Built in 1941
$-- HOA
0.36 acre lot
$598/sq.ft
Description
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.
- Houzeo last checked: 12 hours ago
- Listing updated: October 5, 2026 at 5:51 pm
- Listing Provided by: Lynne Russo (617) 306-2043 | Better Homes and Gardens Real Estate - The Shanahan Group (781) 729-9030
- Source: MLS Property Information Network-MA | MLS#: 73581571

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1941
HOA Fees
-
Finished Area
3,092 sqft
Lot Size
0.36 acre lot
Basement Area
- sqft
MLS Name
MLS Property Information Network
MLS Number
73581571
MLS Status
Active
Days on Market
14

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 4
Bathrooms: 3
Interior
Window Features
Skylight, Screens
Appliances
Gas Water Heater, Range, Dishwasher, Trash Compactor, Microwave, Refrigerator, Washer, Dryer
Interior Features
Closet/cabinets Custom Built, Walk In Closet(s), Cedar Closet(s), Storage, Library, Bonus Room, Play Room, Walk Up Attic
Heating
Central, Baseboard, Natural Gas, Ductless, Fireplace
Sewer
Public Sewer
Exterior Features
Patio, Rain Gutters, Sprinkler System, Screens, Stone Wall
Flooring
Tile, Hardwood, Engineered Hardwood, Flooring Wood, Flooring Wall To Wall Carpet, Laminate
Cooling
Ductless
Construction
Year Built
Year Built: 1941
Home type
Single Family Residence
Architectural Style
Colonial
Construction Materials
Frame
Roof
Shingle
Foundation Details
Concrete Perimeter
Utilities & Energy
Fireplace Features
Family Room, Living Room
Water Source
Public
Parking Features
Attached, Garage Door Opener, Paved Drive, Off Street, Paved
Security Features
Security System
Laundry Features
Gas Dryer Hookup, Washer Hookup, In Basement
Basement
Full, Partially Finished, Interior Entry, Bulkhead, Sump Pump, Concrete
Electric
Circuit Breakers
Other Features
Disclosures
Driveway Located On High Street. Sump In Basement. Rear Door In Garage Has Broken Lock.
Community Features
Public Transportation, Shopping, Park, Walk/jog Trails, Golf, Conservation Area, Highway Access, Public School
Lot Features
Corner Lot, Wooded, Level
Patio And Porch Features
Patio
Price History
| Date | Event | Price |
|---|---|---|
09/23/2026 | Listed for Sale | $1,850,000 $598/sqft |
Source: | ||
Getting Around 1 Overlook Way
Bike Score®
Somewhat Bikeable
27/100
Walk Score®
Car-Dependent
16/100
Data provided by Redfin
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Based on information provided to and compiled by MLS Property Information Network, Inc. covering through Oct 07, 2026, 06:00AM. The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third-party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified. © 2026 MLS Property Information Network, Inc. All Rights Reserved.
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