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Sold for $1,510,000 on 09/02/25
  • $1,510,000

    155 Highland Ave, Winchester, MA 01890

    5beds
    1,965sqft
    Single Family Residence
    Built in 1900
    5,001 Square Feet Lot
    $1,395,100 Zestimate®
    $768/sqft
    $5,055 Estimated rent

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    $9,267/mo

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    What's special

    Charming turn-of-the-century 5-bedroom Gambrel-style home in move-in condition, blending classic character with modern updates. This spacious residence features a beautifully updated interior with central air, a stunning primary suite with private bath, custom closet system, and generous living spaces throughout. The detached 2-car garage adds convenience, while the location offers unbeatable lifestyle perks—just a short stroll to the 2,600-acre Middlesex Fells Reservation. Enjoy easy access to Winchester Center’s shops, restaurants, top-rated schools, and public transportation, including the commuter rail to Boston. Quick access to Rt. 93 puts downtown Boston just minutes away. Basement features small home office with direct access to Beacon Hill style back yard.

    Zillow last checked: 7 hours ago

    Listing updated: August 19, 2025 at 02:52pm

    Listed by:

    Pirani & Wile Group,

    Advisors Living - Winchester,

    Peter Pirani

    Bought with:

    Pirani & Wile Group

    Advisors Living - Winchester

    Source: MLS PIN,MLS#: 73416499

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 5
    • Bathrooms: 3
    • Full bathrooms: 2
    • 1/2 bathrooms: 1
    Primary bedroom
    • Features: Bathroom - Full, Flooring - Hardwood
    • Level: Second
    • Area: 190.48
    • Dimensions: 14.11 x 13.5
    Bedroom 2
    • Features: Flooring - Hardwood
    • Level: Second
    • Area: 184.95
    • Dimensions: 13.7 x 13.5
    Bedroom 3
    • Features: Flooring - Hardwood
    • Level: Second
    • Area: 102.19
    • Dimensions: 12.6 x 8.11
    Bedroom 4
    • Features: Flooring - Hardwood
    • Level: Third
    • Area: 128.76
    • Dimensions: 11.6 x 11.1
    Bedroom 5
    • Features: Flooring - Hardwood
    • Level: Third
    • Area: 93.74
    • Dimensions: 10.9 x 8.6
    Primary bathroom
    • Features: Yes
    Bathroom 1
    • Features: Bathroom - Half, Flooring - Stone/Ceramic Tile
    • Level: First
    • Area: 17.1
    • Dimensions: 5.7 x 3
    Bathroom 2
    • Features: Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile
    • Level: Second
    • Area: 61.41
    • Dimensions: 8.9 x 6.9
    Bathroom 3
    • Features: Bathroom - Full, Bathroom - Tiled With Shower Stall
    • Level: Second
    • Area: 95.76
    • Dimensions: 12.6 x 7.6
    Dining room
    • Features: Flooring - Hardwood, Crown Molding
    • Level: First
    • Area: 189.54
    • Dimensions: 16.2 x 11.7
    Kitchen
    • Features: Flooring - Hardwood, Countertops - Stone/Granite/Solid
    • Level: First
    • Area: 152.59
    • Dimensions: 12.6 x 12.11
    Living room
    • Features: Flooring - Hardwood, Crown Molding
    • Level: First
    • Area: 166.4
    • Dimensions: 13 x 12.8
    Office
    • Features: Flooring - Laminate, Exterior Access
    • Level: Basement
    • Area: 192.91
    • Dimensions: 19.1 x 10.1
    Heating
    • Forced Air, Natural Gas
    Cooling
    • Central Air, Window Unit(s)
    Appliances
    • Laundry: In Basement
    Features
    • Office, Mud Room, Entry Hall
    • Flooring: Hardwood, Laminate, Flooring - Stone/Ceramic Tile, Flooring - Hardwood
    • Windows: Insulated Windows
    • Basement: Partially Finished,Walk-Out Access
    • Number of fireplaces: 1
    • Fireplace features: Living Room
    Interior area
    • Total structure area: 1,965
    • Total interior livable area: 1,965 sqft
    • Finished area above ground: 1,965

    Property

    Parking
    • Total spaces: 2
    • Parking features: Detached, Paved Drive
    • Garage spaces: 2
    • Has uncovered spaces: Yes
    Accessibility
    • Accessibility features: No
    Features
    • Patio & porch: Porch, Patio
    • Exterior features: Porch, Patio, Sprinkler System
    Lot
    • Size: 5,001 sqft
    Details
    • Parcel number: M:003 B:0104 L:0,894889
    • Zoning: RDB

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Colonial
    • Property subtype: Single Family Residence
    Materials
    • Frame
    • Foundation: Stone
    • Roof: Shingle
    Condition
    • Year built: 1900

    Utilities & green energy

    • Electric: Circuit Breakers
    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: for Gas Range, for Electric Oven

    Community & neighborhood

    Community
    • Community features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Highway Access, Public School, T-Station
    Location
    • Region: Winchester
    Services availability
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    Estimated market value
    $1,395,100