Winning Farm

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Welcome to Winning Farm of Winchester -an award-winning 55+ community and one of Winchester's most sought-after addresses for effortless, elevated living. This meticulously maintained and lightly lived-in 3-bedroom, 2.5-bath townhome offers 2,306 sq ft of thoughtfully designed living, showcasing fine craftsmanship & timeless finishes throughout. Sun-drenched interiors highlight gorgeous hardwood floors, soaring ceilings, & an open-concept first floor ideal for both everyday living & entertaining. The main-level primary suite provides convenience & privacy, creating a seamless single-level living option, while additional bedrooms and flexible spaces upstairs offer room for guests, a home office, or hobbies. The home's inviting layout is complemented by abundant natural light and a warm, welcoming feel in every room. Set within a beautifully maintained community known for its charm and lifestyle, residents enjoy a peaceful setting with close proximity to shops, dining, and major routes.

More Info

Basic Information

  • Bedrooms3
  • Mls StatusUnder Agreement
  • Bathroom3
  • Contingency Inspection
  • Parcel Number M:028 B:0359 L:0,5121083
  • Senior Community YN Yes
  • Unit Number2

Tax Information

  • Tax Assessed Value $1,703,300
  • Tax Year 2025
  • Taxes$18,890

School Information

  • High School Winchester High
  • High SchoolWinchester
  • Junior HighMccall

Parking

  • Parking Spaces4
  • Covered Spaces 2
  • Garage YN Yes
  • Open Parking YN Yes
  • Parking Features Attached, Garage Door Opener, Off Street, Paved

Rooms

  • Bathroom 1 First,9 x 12
  • Bathroom 2 First,5 x 6
  • Bathroom 3 Second,9 x 16
  • Bathrooms Total Decimal 2.5
  • Bedroom 2 Second,12 x 23
  • Bedroom 3 Second,12 x 17
  • Dining Room Main, First,11 x 11
  • Family Room Second,11 x 30
  • Full Bath2
  • Half Baths1
  • Kitchen Main, First,13 x 15
  • Living Room Main, First,12 x 15
  • Main Level Bedrooms 1
  • Master Bedroom Main, First,12
  • Office Main,12 x 11

Basic Information

  • List Price$1,899,000
  • MLS Number73496895
  • Modification Date05/03/2026
  • Property SubTypeCondominium
  • Purchase Contract Date04/14/2026
  • Virtual TourView Tour

Location

  • SubdivisionWinning Farm
  • Address2 Gershon Way
  • Building Number2
  • CountyMiddlesex
  • StateMA
  • StreetGershon Way
  • TownWinchester
  • Zip01890

Building

  • Attached Garage YN Yes
  • BasementY
  • Building Area Units Square Feet
  • Common Walls End Unit, Corner
  • Construction Materials Frame
  • Door Features Insulated Doors
  • Entry Level 1
  • FireplaceYes
  • Fireplace Features Living Room
  • Fireplaces Total 1
  • Garage Spaces2
  • Patio And Porch Features Porch
  • Property NameWinning Farm
  • Rooms9
  • Stories2
  • Utilities For Gas Range, Washer Hookup
  • Window Features Insulated Windows
  • Year Built2019
  • Year Built Details Actual
  • Year Built Source Public Records

Interior

  • Flooring Wood, Tile, Flooring - Hardwood
  • Interior Features Cable Hookup, Office, Internet Available - Unknown

Exterior

  • Exterior Features Porch
  • RoofShingle

Utilities

  • Cooling Central Air
  • Cooling YN Yes
  • Electric Circuit Breakers
  • Heat SystemYes
  • Heating Central, Forced Air, Propane
  • Sewer Other
  • Water Source Public

Property Information

  • Square Feet2,306
  • Building Area Source Public Records
  • Living Area 2,306
  • Lot Size Units Acres
  • Structure Type Townhouse

Amenities

  • Adult CommunityYes
  • Amenities
    • Adult Community
    • Conservation Area
    • House of Worship
    • Park
    • Public School
    • Public Transportation
    • Shopping
    • T-Station
    • Walk/Jog Trails
  • Appliances IncludedRange, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
  • Other AmenitiesFireplace
  • PetsYes w/ Restrictions

Other

  • Association Fee $975
  • Association Fee Frequency Monthly
  • Association Fee Includes
    • Insurance
    • Maintenance Grounds
    • Maintenance Structure
    • Reserve Funds
    • Road Maintenance
    • Sewer
    • Snow Removal
    • Trash
    • Water
  • Date Listed04/07/2026
  • Farm Land Area Units Square Feet
  • View Count5

Map Location

Driving Directions

Listed by The Marrocco Group of Coldwell Banker Realty - Lexington

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