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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 Dec 08, 2025
49
Single Family Listed
75
Avg DOM
559
Avg $ / SqFt
$1,975,447
Avg List Price

Property Details

Price:
$1,549,000
MLS #:
73449320
Status:
Pending
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Winter pond area
Listed Date:
Oct 29, 2025
Finished Sq Ft:
2,587
Total Sq Ft:
2,587
Lot Size:
18,117 sqft / 0.42 acres (approx)
Year Built:
1933
WaterfrontPoolTennisWinter Pond AreaLynchMccallWhs

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

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Community

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 $559. The average listing price for Single Family in Winchester is $1,975,447. 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 James
32 Woodside Road
Winchester, MA