$1,899,000
2 Gershon Way
Winchester, MA, 01890
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.
Property Details
Price:
$1,899,000
MLS #:
73496897
Status:
Pending
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Winning Farm
Listed Date:
Apr 7, 2026
Finished Sq Ft:
2,306
Total Sq Ft:
2,306
Year Built:
2019
Schools
Interior
Above Grade Finished Area
2306
Appliances
Water Heater, Range, Dishwasher, Disposal, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
1
Flooring
Tile, Hardwood, Flooring – Hardwood
Heating
Central, Forced Air, Propane
Interior Features
Cable Hookup, Office, Internet Available – Unknown
Laundry Features
Main Level, First Floor, Washer Hookup
Main Level Bathrooms
2
Main Level Bedrooms
1
Exterior
Architectural Style
Cottage
Attached Garage YN
1
Community
55+
Community Features
Public Transportation, Shopping, Walk/Jog Trails, Highway Access, House of Worship, Public School, T-Station
Construction Materials
Frame
Covered Spaces
2
Exterior Features
Porch, Professional Landscaping
Garage Spaces
2
Lot Features
Cul-De-Sac, Corner Lot
Open Parking Spaces
2
Open Parking YN
1
Parking Features
Attached, Garage Door Opener, Off Street, Paved
Parking Spots
4
Parking Total
4
Patio And Porch Features
Porch
Roof
Shingle
Senior Community YN
1
Window Features
Insulated Windows
Financial
HOA Fee
$975
HOA Fee Frequency
Monthly
Tax Year
2025
Taxes
$18,890
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Winchester as of Jun 20, 2026
77
Single Family Listed
52
Avg DOM
550
Avg $ / SqFt
$2,163,397
Avg List Price
Community
- Address2 Gershon Way Winchester MA
- SubdivisionWinning Farm
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- Located in the Winning Farm subdivision, 2 Gershon Way Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,899,000 and features 3 beds, 3 baths, and has approximately 2,306 square feet of living space, and was originally constructed in 2019. The current price per square foot is $824. The average price per square foot for Single Family listings in Winchester is $550. The average listing price for Single Family in Winchester is $2,163,397. To schedule a showing of MLS#73496897 at 2 Gershon Way in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of Coldwell Banker Realty – Winchester. The property listing data and information 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 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 set forth herein.
2 Gershon Way
Winchester, MA