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Welcome to Winning Farm, an award-winning 55+ community in Winchester, just 8 miles North of Boston. This stunning 3 bedroom, 2.5 bath home offers thoughtful design and exceptional attention to detail throughout. Step inside to soaring ceilings, hardwood floors, and an inviting open floor plan perfect for entertaining or relaxing by the fire. The first-floor primary suite provides comfort and convenience, while a private home office with coffered ceilings and a versatile loft area make working from home effortless. Enjoy seamless indoor-outdoor living with a screened-in porch, patio, and sun-drenched rooms that fill the home with natural light. The finished lower level offers abundant space for extended living as well as generous storage options. This custom townhome combines elegance and functionality in a premier, private end unit location, surrounded by the serenity and peacefulness of Winning Farm.
Current real estate data for Condo in Winchester as of Oct 07, 2025
17
Condo Listed
42
Avg DOM
600
Avg $ / SqFt
$987,482
Avg List Price

Property Details

Price:
$2,299,000
MLS #:
73436924
Status:
Active
Beds:
3
Baths:
2.5
Type:
Condo
Subtype:
Condominium
Listed Date:
Sep 30, 2025
Finished Sq Ft:
3,959
Total Sq Ft:
3,959
Year Built:
2020
Community 55 PlusWinning Farm Of WinchesterYes W/ Restrictions

Schools

Interior

Appliances
Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
1
Flooring
Tile, Vinyl, Hardwood
Heating
Forced Air, Propane
Laundry Features
First Floor, In Unit

Exterior

Association Amenities
Trail(s)
Community
55+
Community Features
Public Transportation, Shopping, Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, Adult Community
Construction Materials
Frame
Exterior Features
Porch – Enclosed, Patio, Professional Landscaping, Sprinkler System
Parking Features
Attached, Deeded, Off Street
Parking Spots
2
Roof
Shingle

Financial

HOA Fee
$975
HOA Frequency
Monthly
HOA Includes
Water, Sewer, Insurance, Maintenance Grounds, Snow Removal, Trash, Reserve Funds
Tax Year
2025
Taxes
$18,130

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Property Summary

    19 Gershon Way # 19 Winchester MA is a Condo for sale in Winchester, MA, 01890. It is listed for $2,299,000 and features 3 beds, 3 baths, and has approximately 3,959 square feet of living space, and was originally constructed in 2020. The current price per square foot is $581. The average price per square foot for Condo listings in Winchester is $600. The average listing price for Condo in Winchester is $987,482. To schedule a showing of MLS#73436924 at 19 Gershon Way # 19 in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.

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CRP: Certified Relocation Professional
CRS: Certified Residential Specialist
GRI: Graduate of Realtors Institute
CBR: Certified Buyers Representative
BSBA: Bachelor of Science in Business Administration. Babson College 1979
MBA: Master of Business Administration. Babson College 2002

James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…

More About James
19 Gershon Way # 19
Winchester, MA