Save
Ask
Tour
Hide
Share
$1,339,000
14 Days On Site

155 Highland Ave
Winchester, MA 01890

For Sale|Single Family Residence|Pending
5
Beds
3
Total Baths
2
Full Baths
1
Partial Bath
1,965
SqFt
$681
/SqFt
1900
Built
County:
Middlesex

Due to the health concerns created by Coronavirus we are offering personal 1-1 online video walkthough tours where possible.

155 Highland Ave155 Highland Ave155 Highland Ave155 Highland Ave
Save
Ask
Tour
Hide
Share

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.

Save
Ask
Tour
Hide
Share
Listing Snapshot
Price 
$1,339,000
Days On Site 
14 Days
Bedrooms 
5
Inside Area (SqFt) 
1,965 sqft
Total Baths 
3
Full Baths 
2
Partial Baths 
1
Lot Size 
0.11 Acres
Year Built 
1900
MLS® Number 
73416499
Status 
Pending
Property Tax 
$14,404
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
5 days agoListing updated with changes from the MLS®
7 days agoStatus changed to Pending
2 weeks agoListing first seen on site
General Features
Acres 
0.11
Disclosures 
Non working fireplace,radiant heat in mudroom
Foundation 
Stone
Garage 
Yes
Garage Spaces 
2
Parking 
PavedDetached
Parking Spaces 
2
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Above 
1965
SqFt Total 
1965
Style 
Colonial
Water Source 
Public
Zoning 
RDB
Interior Features
Appliances 
Gas Water HeaterRangeDishwasherDisposalRefrigeratorWasherDryer
Basement 
Partially FinishedWalk-Out Access
Cooling 
Central AirWindow Unit(s)
Electric 
Circuit Breakers
Fireplace 
Yes
Fireplace Features 
Living Room
Fireplaces 
1
Flooring 
HardwoodLaminate
Heating 
Natural GasForced Air
Laundry Features 
In Basement
Window Features 
Insulated Windows
Bathroom 1 
Dimensions - 5.7x3Level - FirstArea - 17
Bathroom 2 
Dimensions - 8.9x6.9Level - SecondArea - 61
Bathroom 3 
Dimensions - 12.6x7.6Level - SecondArea - 95
Bedroom 2 
Dimensions - 13.7x13.5Level - SecondArea - 184
Bedroom 3 
Dimensions - 12.6x8.11Level - SecondArea - 102
Bedroom 4 
Dimensions - 11.6x11.1Level - ThirdArea - 128
Bedroom 5 
Dimensions - 10.9x8.6Level - ThirdArea - 93
Dining Room 
Dimensions - 16.2x11.7Level - FirstArea - 189
Kitchen 
Dimensions - 12.6x12.11Level - FirstArea - 152
Living Room 
Dimensions - 13x12.8Level - FirstArea - 166
Master Bedroom 
Dimensions - 14.11x13.5Level - SecondArea - 190
Office 
Dimensions - 19.1x10.1Level - BasementArea - 192
Save
Ask
Tour
Hide
Share
Exterior Features
Construction Details 
Frame
Patio And Porch 
PorchPatio
Roof 
Shingle
Windows/Doors 
Insulated Windows
Community Features
Community Features 
Tennis Court(s)Park
Schools
School District
Unknown
Elementary School
Muraco
Middle School
Mccall
High School
Whs
Listing courtesy of Pirani & Wile Group of Advisors Living - Winchester



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, landlords, 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, leasing or renting 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, leasing or renting. 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.

Last checked 2025-08-26 09:35 PM UTC

Neighborhood & Commute
Source: Walkscore
Save
Ask
Tour
Hide
Share