155 Highland Ave, Winchester, MA 01890

Local realty services provided by:Better Homes and Gardens Real Estate The Masiello Group
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155 Highland Ave,Winchester, MA 01890
$1,339,000
  • 5 Beds
  • 3 Baths
  • 1,965 sq. ft.
  • Single family
  • Active
Upcoming open houses
  • Sat, Aug 16
    11:00 am - 12:30 pm
  • Sun, Aug 17
    11:00 am - 12:30 pm
Listed by:pirani & wile group
Office:advisors living - winchester
MLS#:73416499
Source:MLSPIN

Price summary

  • Price:$1,339,000
  • Price per sq. ft.:$681.42

About this home

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.

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Home facts

  • Year built:1900
  • Listing Id #:73416499
  • Updated:August 15, 2025 at 10:29 AM

Rooms and interior

  • Bedrooms:5
  • Total bathrooms:3
  • Full bathrooms:2
  • Half bathrooms:1
  • Living area:1,965 sq. ft.

Heating and cooling

  • Cooling:Central Air, Window Unit(s)
  • Heating:Forced Air, Natural Gas

Structure and exterior

  • Roof:Shingle
  • Year built:1900
  • Building area:1,965 sq. ft.
  • Lot area:0.11 Acres

Schools

  • High school:Whs
  • Middle school:Mccall
  • Elementary school:Muraco

Utilities

  • Water:Public
  • Sewer:Public Sewer

Finances and disclosures

  • Price:$1,339,000
  • Price per sq. ft.:$681.42
  • Tax amount:$14,404 (2025)
The property listing data and information, or the Images, 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, and the Images, 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, or as to the accuracy of any of the Images, set forth herein.

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