$1,850,000

Monthly Est:$9,208

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon3,092sqft

1 Overlook Way, Winchester, MA 01890

$9,208/moEst:

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  • 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 MLS Property Information Network-MA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Middlesex County

  • City

    Winchester

  • 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

DateEventPrice

09/23/2026

Listed for Sale

$1,850,000

$598/sqft

Source: mls_logoMLS Property Information Network-MA #73581571

Getting Around 1 Overlook Way

Bike Score®

Bike Score

Somewhat Bikeable

27/100

Walk Score®

Walk Score

Car-Dependent

16/100

Data provided by Redfin

Nearby Homes

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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