32 Woodside Road
Winchester, MA, 01890
$1,549,000
Must see! Nestled along Winchesters beloved Winter Pond, this beautiful home offers a rare opportunity to live the waterfront dream just 7 miles from Boston! Featuring an oversized lot with breathtaking panoramic water views & offering a lifestyle that could include kayaking, paddle boarding, ice skating, fishing etc..along with serenity and privacy so hard to find. This home offers ample living space that flows nicely between the formal living room, dining room, kitchen, office and family room, all of which have picturesque views. Many recent updates including kitchen, baths, roof, heating & de-leading; making this lovely home move in ready! 3 to 4 bedrooms, 2 1/2 baths w/ a finished walk out basement w/ mud room, laundry, rec. room, storage and gym area. The setting is simply gorgeous with expansive rolling green lawn offering plenty of room for future expansion.Enjoy your morning coffee from deck appreciating all that nature offers, plus spectacular sunsets in the western skies!
Current real estate data for Single Family in Winchester as of Oct 31, 2025
61
Single Family Listed
67
Avg DOM
543
Avg $ / SqFt
$2,122,797
Avg List Price
Property Details
Price:
$1,549,000
MLS #:
73449320
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Winter pond area
Listed Date:
Oct 30, 2025
Finished Sq Ft:
2,587
Total Sq Ft:
2,587
Lot Size:
18,117 sqft / 0.42 acres (approx)
Year Built:
1933
Schools
Elementary School:
Lynch
Middle School:
Mccall
High School:
Whs
Interior
Appliances
Range, Dishwasher, Disposal, Refrigerator, Freezer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Window Unit(s)
Fireplaces Total
1
Flooring
Wood, Tile, Flooring – Hardwood
Heating
Baseboard, Natural Gas
Laundry Features
In Basement
Exterior
Architectural Style
Colonial
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, Bike Path, Conservation Area, Highway Access, House of Worship, Marina, Private School, Public School, T-Station
Construction Materials
Brick
Exterior Features
Deck, Deck – Wood, Rain Gutters, Storage, Professional Landscaping, Screens, Fenced Yard
Parking Features
Paved Drive, Off Street
Parking Spots
4
Roof
Shingle
Financial
Tax Year
2025
Taxes
$14,917
Map
Contact Us
Mortgage Calculator
Community
- Address32 Woodside Road Winchester MA
- SubdivisionWinter pond area
- 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
- Located in the Winter pond area subdivision, 32 Woodside Road Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,549,000 and features 3 beds, 3 baths, and has approximately 2,587 square feet of living space, and was originally constructed in 1933. The current price per square foot is $599. The average price per square foot for Single Family listings in Winchester is $543. The average listing price for Single Family in Winchester is $2,122,797. To schedule a showing of MLS#73449320 at 32 Woodside Road 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.
32 Woodside Road
Winchester, MA