1 Overlook Way, WedgemereWinchester, MA 01890MLS Number 73581571

  • Price: $1,850,000
  • Est. Mortgage of $/month
  • 1 Day on Market
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$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Sep 17, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
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Open House
1 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 018901 Overlook Way Winchester MA 01890
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  • 4Bedrooms
  • 0.36Acreage
  • 3Bathrooms
  • 1941Year Built

Driving Directions

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.

Open Houses

September 24th
Starts: 5:00pm
Ends: 6:30pm
Comments: Don't miss this gem - nestled in between Ambrose Elementary School neighborhoods and the rolling hills of the Winchester Country Club.
September 25th
Starts: 12:00pm
Ends: 1:30pm
September 26th
Starts: 11:00am
Ends: 12:30pm
September 27th
Starts: 12:00pm
Ends: 1:30pm
Listed by Lynne Russo of Better Homes and Gardens Real Estate - The Shanahan Group

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More Info

Basic Information

  • Bedrooms4
  • Mls StatusNew
  • Bathroom3
  • Listing Terms Contract
  • Lot Features Corner Lot, Wooded, Level
  • Parcel Number 20 152 0,900071
  • Road Frontage DescriptionPaved

Basic Information

  • List Price$1,850,000
  • MLS Number73581571
  • Modification Date09/23/2026
  • Property SubTypeSingle Family Residence

Building

  • Attached Garage YN Yes
  • Basement
    • Bulkhead
    • Concrete
    • Full
    • Interior Entry
    • Partially Finished
    • Sump Pump
  • Building Area Units Square Feet
  • Construction Materials Frame
  • FireplaceYes
  • Fireplace Features Family Room, Living Room
  • Fireplaces Total 3
  • FoundationConcrete Perimeter
  • Garage Spaces2
  • Patio And Porch Features Patio
  • Property StyleColonial
  • Rooms11
  • Window Features Skylight, Screens
  • Year Built1941
  • Year Built Details Actual
  • Year Built Source Public Records

Amenities

  • Amenities
    • Conservation Area
    • Golf
    • Highway Access
    • Park
    • Public School
    • Public Transportation
    • Shopping
    • Walk/Jog Trails
  • Appliances IncludedGas Water Heater, Range, Dishwasher, Trash Compactor, Microwave, Refrigerator, Washer, Dryer
  • Security Features Security System

Tax Information

  • Tax Assessed Value $1,593,000
  • Tax Year 2026
  • Taxes$17,650

Parking

  • Parking Spaces6
  • Covered Spaces 2
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features Attached, Garage Door Opener, Paved Drive, Off Street, Paved

Location

  • NeighborhoodWedgemere
  • SubdivisionWedgemere
  • Address1 Overlook Way
  • Building Number1
  • CountyMiddlesex
  • StateMA
  • StreetOverlook Way
  • TownWinchester
  • Zip01890

Property

  • Acreage0.36
  • Frontage Length 127

Exterior

  • Exterior Features Patio, Rain Gutters, Sprinkler System, Screens, Stone Wall
  • RoofShingle

Utilities

  • Cooling Ductless
  • Cooling YN Yes
  • Electric Circuit Breakers
  • Heat SystemYes
  • Heating
    • Baseboard
    • Central
    • Ductless
    • Electric
    • Fireplace
    • Natural Gas
  • Sewer Public Sewer
  • Water Source Public

Other

  • Date Listed09/23/2026
  • Farm Land Area Units Square Feet

School Information

  • High School Winchester
  • Elementary SchoolAmbrose
  • High SchoolWinchester
  • Junior HighMccall

Rooms

  • Bathroom 1 Main, First,6 x 4
  • Bathroom 2 Second,13 x 5
  • Bathroom 3 Second,9 x 5
  • Bathrooms Total Decimal 2.5
  • Bedroom 2 Second,16 x 13
  • Bedroom 3 Second,19 x 12
  • Bedroom 4 Second,12 x 12
  • Dining Room Main, First,13 x 12
  • Family Room First,20 x 15
  • Full Bath2
  • Half Baths1
  • Kitchen Main, First,17 x 13
  • Living Room Main, First,18 x 13
  • Main Level Bathrooms 1
  • Master Bedroom Second,19

Interior

  • Flooring
    • Engineered Hardwood
    • Flooring - Wall to Wall Carpet
    • Flooring - Wood
    • Hardwood
    • Laminate
    • Tile
  • Interior Features
    • Bonus Room
    • Cedar Closet(s)
    • Closet/Cabinets - Custom Built
    • Library
    • Play Room
    • Storage
    • Walk-In Closet(s)
    • Walk-up Attic

Property Information

  • Square Feet3,092
  • Building Area Source Measured
  • Living Area 3,092
  • Lot Size Square Feet 15,705
  • Lot Size Units Acres
  • Road Responsibility Public Maintained Road

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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. MLSPIN 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.

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