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Exceptional Victorian era gem, steps from Town Center, schools, commuter rail, and the Fells! This spacious period home seamlessly blends modern elegance with timeless charm. It’s special features include: an inviting farmer’s porch, generous living and dining rooms well-suited for entertaining, first floor family room, covered porch for al fresco dining, primary suite with ensuite bath, home office, sun room, central AC (8 mini-splits), Lochinvar heating sys (2025), hardwood floors, 3 fireplaces, and more. The stunning kitchen combines function, design, and quality showcasing custom cabinets, granite countertops, stainless appliances, and tasteful lighting. Bring your design ideas for the third floor and personalize the space for your needs. The lower level, with an outside entrance and a half bath, is well suited for an in-law suite, or au pair accommodations. The lovely backyard with its Zen Garden includes many thoughtfully organized plantings and flowering trees. Welcome home!
Current real estate data for Single Family in Winchester as of Dec 17, 2025
42
Single Family Listed
74
Avg DOM
581
Avg $ / SqFt
$1,850,236
Avg List Price

Property Details

Price:
$1,699,000
MLS #:
73461480
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Dec 10, 2025
Finished Sq Ft:
3,343
Total Sq Ft:
3,343
Lot Size:
5,724 sqft / 0.13 acres (approx)
Year Built:
1894
Lincoln ElementaryMccall MiddleWinchester High

Schools

Elementary School:
Lincoln Elementary
Middle School:
Mccall Middle
High School:
Winchester High

Interior

Appliances
Gas Water Heater, Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms, 2 Half Bathrooms
Cooling
Ductless
Fireplaces Total
3
Flooring
Wood, Tile, Carpet, Flooring – Hardwood, Flooring – Stone/Ceramic Tile
Heating
Hot Water, Natural Gas
Laundry Features
First Floor

Exterior

Architectural Style
Victorian, Colonial Revival
Community Features
Public Transportation, Shopping, Walk/Jog Trails, Conservation Area, Highway Access, Public School, T-Station
Exterior Features
Porch, Porch – Screened, Deck, Fenced Yard, Garden
Parking Features
Detached, Paved Drive, Off Street, Paved
Parking Spots
3
Roof
Shingle

Financial

Tax Year
2025
Taxes
$18,383

Map

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Community

Property Summary

    263 Highland Ave Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,699,000 and features 4 beds, 3 baths, and has approximately 3,343 square feet of living space, and was originally constructed in 1894. The current price per square foot is $508. The average price per square foot for Single Family listings in Winchester is $581. The average listing price for Single Family in Winchester is $1,850,236. To schedule a showing of MLS#73461480 at 263 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 James
263 Highland Ave
Winchester, MA