Charming Spanish-style home in desirable Winchester! This unique property features a beautiful terracotta roof and timeless architectural details. The first floor welcomes you with a foyer which leads to an astounding great room, perfect for entertaining or hosting family gatherings. The kitchen opens seamlessly to the dining area. Additionally an inviting enclosed patio provides space to relax or enjoy morning coffee. A cozy sitting area and convenient half bath complete the main level. Upstairs, you’ll find two comfortable bedrooms and a renovated full bathroom with modern finishes. The lower level offers an unfinished basement ideal for storage or future expansion, plus an attached garage for added convenience. Whether you’re an investor seeking potential or an end user looking for a fixer-upper, this home presents an incredible opportunity in one of Winchester’s most sought-after neighborhoods.
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:
$999,000
MLS #:
73449918
Status:
Active Under Contract
Beds:
2
Baths:
1.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Oct 31, 2025
Finished Sq Ft:
2,033
Total Sq Ft:
2,033
Lot Size:
12,336 sqft / 0.28 acres (approx)
Year Built:
1926
Schools
Interior
Appliances
Water Heater, Range, Disposal, Microwave, Refrigerator, Dryer, Vacuum System, Plumbed For Ice Maker
Bathrooms
1 Full Bathroom, 1 Half Bathroom
Cooling
Central Air, Whole House Fan
Fireplaces Total
1
Flooring
Tile, Hardwood
Heating
Steam, Oil
Laundry Features
Electric Dryer Hookup, Washer Hookup
Exterior
Architectural Style
Spanish Colonial
Community Features
Shopping, Walk/Jog Trails
Construction Materials
Frame
Exterior Features
Porch – Enclosed, Rain Gutters
Parking Features
Attached, Paved Drive, Paved
Parking Spots
2
Roof
Clay
Financial
Tax Year
2025
Taxes
$13,500
Map
Contact Us
Mortgage Calculator
Community
- Address446 Highland Ave 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
- 446 Highland Ave Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $999,000 and features 2 beds, 2 baths, and has approximately 2,033 square feet of living space, and was originally constructed in 1926. The current price per square foot is $491. 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#73449918 at 446 Highland Ave 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 Keller Williams Realty Boston Northwest. 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.
446 Highland Ave
Winchester, MA