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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
WoodedPoolTennisCommunity 55 PlusMccallWinchester

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

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Community

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 James
19 Gershon Way
Winchester, MA