19 Gershon Way
Winchester, MA, 01890
$2,299,000
Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in sunroom and enjoy the peaceful wooded backdrop—your own private oasis. The luxurious first-floor primary retreat offers an oversized spa-like bathroom, a large walk-in closet, and direct access to the convenient first-floor laundry. Upstairs, you’ll find two generous bedrooms, a full bath, and a cozy loft ready to be tailored to your needs. The finished lower level provides a spacious family room and ample storage. With a two-car garage and maintenance-free living, this exceptional home offers comfort, elegance, and ease in one perfect package.
Current real estate data for Single Family in Winchester as of Nov 17, 2025
63
Single Family Listed
69
Avg DOM
554
Avg $ / SqFt
$2,056,473
Avg List Price
Property Details
Price:
$2,299,000
MLS #:
73452677
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Nov 7, 2025
Finished Sq Ft:
3,953
Total Sq Ft:
3,953
Year Built:
2020
Schools
Middle School:
Mccall
High School:
Winchester
Interior
Appliances
Electric Water Heater, Water Heater, Range, Dishwasher, Disposal, Trash Compactor, Refrigerator, Washer, Dryer, Vacuum System – Rough-in, Range Hood, Plumbed For Ice Maker
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
1
Flooring
Tile, Hardwood, Wood Laminate, Flooring – Hardwood
Heating
Forced Air, Propane
Laundry Features
Electric Dryer Hookup, Washer Hookup, First Floor
Exterior
Architectural Style
Craftsman
Community
55+
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-Station
Construction Materials
Frame
Exterior Features
Patio, Covered Patio/Deck, Rain Gutters, Sprinkler System, Screens, Stone Wall, ET Irrigation Controller, Outdoor Gas Grill Hookup
Parking Features
Attached, Paved Drive, Paved
Parking Spots
2
Roof
Shingle
Security Features
Security System
Financial
HOA Fee
$975
HOA Frequency
Monthly
Tax Year
2025
Taxes
$18,130
Map
Contact Us
Mortgage Calculator
Community
- Address19 Gershon Way Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Close to Wright Locke Farm
- Cox Road / High St Extension neighborhood
- East SIde near town forest!!
- Everett/ Stratford
- Flats location
- FLATS location Across from Wedgemere/Oxford
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Ledgewood Estates
- Middlesex
- Myopia Hill/ Winchester Country Club Area
- Near VO school
- old village/ West side
- The Flats
- Top neighborhood near town center
- West side
Property Summary
- 19 Gershon Way Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $2,299,000 and features 3 beds, 3 baths, and has approximately 3,953 square feet of living space, and was originally constructed in 2020. The current price per square foot is $582. The average price per square foot for Single Family listings in Winchester is $554. The average listing price for Single Family in Winchester is $2,056,473. To schedule a showing of MLS#73452677 at 19 Gershon Way 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 JamesCourtesy of Compass. 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.
19 Gershon Way
Winchester, MA












































