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1 Overlook WayWinchester, MA 01890

For Sale

$1,750,000

Smart Buyer Rebate $8,750

NEW Photos! Welcome to One Overlook Way in Winchester. This home is located on a 1/3 acre corner lot on a short cul-de-sac off High Street- a premier location close to Ambrose Elementary School and the Winchester Country Club. Don't miss this spacious 4+ bedroom center-entrance Colonial. with a thoughtfully designed circular 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 with room to add an island or large table also opens naturally into the comfortable family room - with gas fireplace, custom built-ins, a new split AC and access to the back and side yard! 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 split AC, 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 second home office, hangout zone or storage. The finished lower level adds another playroom, 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 storage 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.

Listed by Lynne Russo

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Better Homes and Gardens Real Estate - The Shanahan Group

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6173062043

Last updated October 30, 2026

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Source: MLSPin #73581571

Listing Facts

  • TypeSingle-family
  • NeighborhoodWedgemere
  • Bedrooms4
  • Bathrooms3
  • Days on Prevu38
  • Taxes$17,650/year
  • Size3,604 sqft
  • Price per sqft$486

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Parking

Location

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Listing History

10/26/2026
Price Decreased
$1,750,000
09/23/2026
Listed by Better Homes and Gardens Real Estate - The Shanahan Group
$1,850,000
  1. 10/26/2026$1,750,000
    Price Decreased
  2. 09/23/2026$1,850,000
    Listed by Better Homes and Gardens Real Estate - The Shanahan Group

Property Details for 1 Overlook Way

Association

Amenities

  • Community Features: Park, Golf

Exterior

Construction

  • Roof: Shingle
  • Window Features: Skylight(s), Screens
  • Year Built: 1941
  • Year Built Details: Actual
  • Architectural Style: Colonial
  • Construction Materials: Frame
  • Exterior Features: Rain Gutters

Features

  • Fencing: Stone
  • Patio And Porch Features: Patio

Measurements

  • Building Area Total: 3,604
  • Building Area Units: Square Feet
  • Frontage Length: 127
  • Lot Features: Corner Lot, Wooded, Level
  • Lot Size Acres: 0.36
  • Lot Size Area: 0
  • Lot Size Square Feet: 15,680
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: 20 152 0,900071
  • Tax Annual Amount: $17,650.00
  • Tax Assessed Value: $1,593,000.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Trash Compactor, Gas Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
  • Fireplace Features: Family Room, Living Room
  • Fireplace: Yes
  • Fireplaces Total: 3
  • Flooring: Tile, Hardwood, Laminate
  • Interior Features: Walk-In Closet(s), Cedar Closet(s), Storage, Open Floorplan, Recessed Lighting

Measurements

  • Living Area: 3,604

Rooms

  • Basement: Full, Partially Finished, Interior Entry, Sump Pump, Concrete
  • Has Basement: Yes
  • Bathrooms Full: 2
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 4
  • Main Level Bathrooms: 1
  • Rooms Total: 11

Other

Location

  • Tax Block: 152

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 2
  • Garage Spaces: 2
  • Garage: Yes
  • Open Parking Spaces: 4
  • Open Parking: Yes
  • Parking Features: Paved, Attached, Garage Door Opener, Off Street, Garage
  • Parking Total: 6

Schools

Elementary School

  • Elementary School: Ambrose

High School

  • High School: Whs

Middle or Junior School

  • Middle Or Junior School: Mccall

Utilities

Equipment

  • Cooling: Ductless, Zoned
  • Has Cooling: Yes
  • Electric: Circuit Breakers
  • Heating: Natural Gas, Central, Baseboard, Ductless, Zoned
  • Has Heating: Yes
  • Laundry Features: Gas Dryer Hookup, Washer Hookup, In Basement
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 3 bathrooms in this single-family home at 1 Overlook Way.

What schools are nearby to 1 Overlook Way?

Nearby schools include the Ambrose Elementary School, Mccall Middle School, and Whs High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 1 Overlook Way.

What are the annual taxes for 1 Overlook Way?

Annual taxes for this single-family home are estimated at $17,650.

How does 1 Overlook Way compare to other single-family homes in Wedgemere?

This single-family home is listed 20% below the average price for single-family homes in Wedgemere and has been on the market for 24 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 3,604 sqft.

1 Overlook Way is a 4-bedroom, 3-bath single-family home for sale in Winchester MA 01890. On Prevu for 38 days at $1,750,000. This includes a recent price decrease of $100,000. This home features 3,604 square feet of living space, located in Wedgemere. The median listing price for single-family homes in this area is $1,974,000. Nearby schools include Ambrose Elementary School, Mccall Middle School, and Whs High School. The home offers private outdoor space, dishwasher, parking, and washer/dryer. View other single-family home listings in Middlesex County.

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, landlords 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, leasing or renting 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, leasing or renting. 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.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.