Winning Farm

Listing Tools

Picture Perfect! The crown jewel of Winning Farm, a 55+ community ideally situated in the heart of Winchester. Step inside to find a bright, open-concept living space. Soaring ceilings, gleaming hardwood floors and refined architectural details create an airy, elevated atmosphere. Beautiful private office. Gourmet kitchen with premium appliances, stone countertops and oversized island for casual dining and entertaining. Dining area with coffered ceilings, fireplaced living room, and bonus screened porch to enjoy the view of the lush conservation land and walking trails. The luxurious primary retreat offering a spa-like bath with double vanities .Laundry room and 1/2 bath round out the main level. Upper level boasts 2 additional bedrooms, a full bath and flexible, cozy loft space. Amazing, walk out lower level includes a full gym, patio for grilling, built in cabinets, full bath and spectacular, custom built wine cellar Two car garage. This opportunity is not to be missed!

More Info

Basic Information

  • Bedrooms3
  • Mls StatusUnder Agreement
  • Bathroom4
  • Contingency Pending P&S
  • Parcel Number 5121094
  • Senior Community YN Yes
  • Unit Number15

Tax Information

  • Tax Assessed Value $1,860,400
  • Tax Year 2026
  • Taxes$20,632

Parking

  • Parking Spaces4
  • Covered Spaces 2
  • Garage YN Yes
  • Parking Features Attached, Garage Door Opener

Rooms

  • Bathroom 1 First,6.4 x 5.2
  • Bathroom 2 First,12.2 x 10.6
  • Bathroom 3 Second,8.2 x 9.2
  • Bathrooms Total Decimal 3.5
  • Bedroom 2 Second,18.5 x 12.1
  • Bedroom 3 Second,17.2 x 12.1
  • Dining Room First,12.7 x 11.7
  • Family Room First
  • Full Bath3
  • Half Baths1
  • Kitchen First,13.9 x 7.1
  • Living Room First,14.8 x 16.9
  • Master Bedroom First,16.1
  • Office First,11.1 x 11.1

Basic Information

  • List Price$2,395,000
  • MLS Number73495315
  • Modification Date04/28/2026
  • Property SubTypeCondominium
  • Purchase Contract Date04/15/2026

Location

  • SubdivisionWinning Farm
  • Address15 Gershon Way
  • Building Number15
  • CountyMiddlesex
  • StateMA
  • StreetGershon Way
  • TownWinchester
  • Zip01890

Building

  • Attached Garage YN Yes
  • BasementY
  • Building Area Units Square Feet
  • Door Features French Doors, Pocket Door
  • Entry Level 1
  • FireplaceYes
  • Fireplace Features Living Room
  • Fireplaces Total 1
  • Garage Spaces2
  • Patio And Porch Features Screened, Covered
  • Property NameWinning Farm
  • Rooms11
  • Stories3
  • Year Built2020
  • Year Built Details Actual
  • Year Built Source Public Records

Interior

  • Flooring Hardwood, Flooring - Hardwood
  • Interior Features
    • Bathroom
    • Bathroom - Full
    • Bathroom - Tiled With Shower Stall
    • Ceiling Fan(s)
    • Exercise Room
    • Home Office
    • Lighting - Overhead
    • Loft

Exterior

  • Exterior Features Porch - Screened, Covered Patio/Deck
  • RoofShingle

Utilities

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

Property Information

  • Square Feet4,087
  • Building Area Source Public Records
  • Living Area 4,087
  • Lot Size Units Acres
  • Property Attached YN Yes
  • Structure Type Townhouse, Attached

Amenities

  • Adult CommunityYes
  • AmenitiesAdult Community
  • Appliances IncludedRange, Dishwasher, Disposal, Microwave, Refrigerator, Freezer
  • 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 Listed04/02/2026
  • Farm Land Area Units Square Feet
  • View Count5

Map Location

Driving Directions

Listed by Moira Lown of Coldwell Banker Realty - Wellesley

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