Welcome to this charming 4-bedroom, 2-bath home in desirable Winchester. Ideally located in one of the town’s most sought-after neighborhoods, this well-maintained residence offers the perfect blend of classic character and everyday comfort. The home features a bright and inviting layout with generous living spaces, hardwood floors, bookshelves and windows seats. The kitchen flows seamlessly into the dining and living areas, making it ideal for both daily living and entertaining. Four well-proportioned bedrooms provide flexibility for family, guests, or home office needs, while two full baths add convenience and functionality. Outside, enjoy a private yard perfect for relaxing, gardening, or outdoor gatherings with tons of sunlight. Additional highlights include ample storage, garage with plenty of off-street parking, and a location that truly can’t be beat—just minutes to Winchester Center, commuter rail, parks, and top-rated schools. Showing start at Open Houses 12/14 & 12/15 12-2PM
Current real estate data for Single Family in Winchester as of Feb 16, 2026
36
Single Family Listed
64
Avg DOM
539
Avg $ / SqFt
$2,084,964
Avg List Price
Property Details
Price:
$999,000
MLS #:
73476558
Status:
Active Under Contract
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Feb 11, 2026
Finished Sq Ft:
1,552
Total Sq Ft:
1,552
Lot Size:
6,582 sqft / 0.15 acres (approx)
Year Built:
1920
Schools
Elementary School:
Lynch
Middle School:
Mccall
High School:
Winchester
Interior
Appliances
Range, Oven, Dishwasher, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms
Cooling
None
Fireplaces Total
1
Flooring
Hardwood
Heating
Steam
Laundry Features
Electric Dryer Hookup
Exterior
Architectural Style
Colonial
Community Features
Tennis Court(s), Park, Walk/Jog Trails, Bike Path, Conservation Area, Highway Access, Private School, Public School
Construction Materials
Frame
Exterior Features
Porch – Screened, Deck – Wood
Parking Features
Detached, Off Street, Paved
Parking Spots
4
Roof
Shingle
Financial
Tax Year
2026
Taxes
$12,561
Map
Contact Us
Mortgage Calculator
Community
- Address76 Woodside Road 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
- 76 Woodside Road Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $999,000 and features 4 beds, 2 baths, and has approximately 1,552 square feet of living space, and was originally constructed in 1920. The current price per square foot is $644. The average price per square foot for Single Family listings in Winchester is $539. The average listing price for Single Family in Winchester is $2,084,964. To schedule a showing of MLS#73476558 at 76 Woodside Road in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.
Similar Listings Nearby
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 Pierce Properties Real Estate. 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.
76 Woodside Road
Winchester, MA