Winning Farm
2 Gershon Way, Winchester, MA
Never miss a listing at Winning Farm
Sign in or create a free account to get the fastest available alerts—usually within about five minutes—for new listings and important updates.
Independent brokerage page. Steve Novak Real Estate compiles public MLS listing and sales data for Winning Farm; it is not the building's management company, leasing office, or HOA. Contact Winning Farm directly for management, rental, or maintenance questions.
About Winning Farm
Winning Farm is a located at 2 Gershon Way in Winchester, MA . The building features 3-bedroom residences ranging from 2,306 to 4,087 square feet , with prices from $1.9M to $2.3M . 3 units have sold in the last two years at an average price of $2.1M .
Monthly HOA fees at Winning Farm are typically $975 per month and commonly include Water, Sewer, Insurance . Parking is typically attached, garage door opener, paved, averaging 4.0 spaces per unit.
Figures summarize MLS listing records. Repeat listings can refer to the same residence; records tracked are not the building's total number of units.
Last updated: 2026-09-25
Unit Types at Winning Farm
| Unit Type | Beds | Baths | Sq Ft | Price Range | Available |
|---|---|---|---|---|---|
| 3 Bedroom | 3 | 3 | 2,306 - 3,953 sqft | $1.9M - $2.2M | None listed |
| 3 Bedroom | 3 | 4 | 4,087 sqft | $2.3M | None listed |
Recently Sold at Winning Farm
| Address | Beds/Baths | Sq Ft | List Price | Sold Price | Change | Sold Date |
|---|---|---|---|---|---|---|
| 2 Gershon Way # 2, Winchester MA 01890 | 3bd / 2.5ba | 2,306 | $1.9M | $1.9M | +1.9% | Jun 22, 2026 |
| 15 Gershon Way # 15, Winchester MA 01890 | 3bd / 3.5ba | 4,087 | $2.4M | $2.3M | -2.9% | Jun 17, 2026 |
| 19 Gershon Way # 1, Winchester MA 01890 | 3bd / 2.5ba | 3,953 | $2.3M | $2.2M | -5.4% | Jan 15, 2026 |
Frequently Asked Questions About Winning Farm
Is Steve Novak Real Estate the management company or leasing office for Winning Farm?
No. Steve Novak Real Estate is an independent real estate brokerage. We compile public MLS listing and recent-sales data for Winning Farm to help buyers and sellers make informed decisions. We do not manage the building, lease units on behalf of the owner, or handle HOA matters. For management, leasing, or maintenance inquiries, please contact Winning Farm directly.
Are there any units for sale at Winning Farm?
There are currently no units listed for sale at Winning Farm in Winchester, MA. Check back regularly as new listings are added daily.
What is the price range at Winning Farm?
Prices at Winning Farm range from $1.9M to $2.3M based on recent listings and sales. Prices vary by unit size, floor, and finishes.
What are the unit sizes at Winning Farm?
Units at Winning Farm range from 2,306 to 4,087 square feet, with 3 to 3 bedroom configurations.
How much do condos sell for at Winning Farm?
3 units have sold at Winning Farm in the last two years at an average price of $2.1M. The average time on market was 75 days.
What are the HOA fees at Winning Farm?
Monthly HOA fees at Winning Farm $975 per month. Based on 3 listings with HOA data on file. Fees commonly include Water, Sewer, Insurance. Actual fees vary by unit; confirm with the listing agent.
Is parking available at Winning Farm?
Parking at Winning Farm is typically described as attached, garage door opener, paved. On average, listings include 4.0 parking spaces. Specific arrangements (deeded, assigned, garage vs. surface) vary by unit.
More Buildings & Communities in Winchester, MA
See all homes for sale in Winchester, MA → View all 41 buildings in Winchester →
Looking to Buy or Tour at Winning Farm?
Steve Novak Real Estate is a real estate brokerage that tracks every MLS listing at Winning Farm. Schedule a tour, ask about a specific unit, or get instant alerts when new listings hit the market — download the app or browse all listings below.
Trying to reach the building's management or leasing office? Search "Winning Farm Winchester management" — we are not affiliated with the building's management.

