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.
Sold for $1,510,000
$1,510,000
155 Highland Ave, Winchester, MA 01890
5beds
1,965sqft
Single Family Residence
Built in 1900
5,001 Square Feet Lot
$1,968,800 Zestimate®
$768/sqft
$4,632 Estimated rent
Home value
$1,968,800
$1.77M - $2.22M
$4,632/mo
Zestimate® history
Owner options
List your home for rent
$4,632/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$4,632/mo
Rent Zestimate®
Refinance and save
$9,356/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$9,356/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Small home officeGenerous living spacesCustom closet system
Zillow last checked:
Listing updated:
Listed by:
Pirani & Wile Group 781-608-1805,
Advisors Living - Winchester 978-423-5235,
Peter Pirani 781-608-1805
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
- Included: Gas Water Heater, Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer
- 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: 4
- Parking features: Detached, Paved Drive
- Garage spaces: 2
- Uncovered spaces: 2
Accessibility
- Accessibility features: No
Features
- Patio & porch: Porch, Patio
- Exterior features: Porch, Patio, Sprinkler System
Lot
- Size: 5,001 Square Feet
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 & HOA
Community
- Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Medical Facility, Highway Access, Public School, T-Station
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $768/sqft
- Tax assessed value: $1,298,800
- Annual tax amount: $14,404
- Date on market: 1/18/2026
Price history
| Date | Event | Price |
|---|---|---|
| 9/2/2025 | Sold | $1,510,000+12.8%$768/sqft |
Source: MLS PIN #73416499 Report a problem | ||
| 8/11/2025 | Listed for sale | $1,339,000+391.4%$681/sqft |
Source: MLS PIN #73416499 Report a problem | ||
| 2/26/1996 | Sold | $272,500+28.5%$139/sqft |
Source: Public Record Report a problem | ||
| 2/17/1994 | Sold | $212,000$108/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $14,404 +0.4% | $1,298,800 +2.6% |
| 2024 | $14,343 +7.1% | $1,265,900 +11.5% |
| 2023 | $13,397 +1.4% | $1,135,300 +7.5% |
| 2022 | $13,217 +8.1% | $1,056,500 +10.8% |
| 2021 | $12,231 +3.6% | $953,300 |
| 2020 | $11,811 +5.6% | $953,300 +3.2% |
| 2019 | $11,187 +2.2% | $923,800 +2.9% |
| 2018 | $10,943 +1.5% | $897,700 +2.3% |
| 2017 | $10,781 +6.3% | $877,900 +1.1% |
| 2016 | $10,138 +2.7% | $868,000 +6.7% |
| 2015 | $9,876 +7.7% | $813,500 +12.3% |
| 2014 | $9,170 +11.1% | $724,300 +12.1% |
| 2013 | $8,253 +1.8% | $646,300 |
| 2012 | $8,111 +3.7% | $646,300 |
| 2011 | $7,820 +2.9% | $646,300 -2.1% |
| 2010 | $7,600 +2.1% | $660,300 |
| 2009 | $7,442 +4.1% | $660,300 -2.4% |
| 2008 | $7,151 +6% | $676,500 +3.6% |
| 2007 | $6,744 +6% | $652,900 +6.4% |
| 2006 | $6,363 +12.3% | $613,600 +12.9% |
| 2005 | $5,665 +10% | $543,700 +20.2% |
| 2004 | $5,149 +2.8% | $452,500 +2.8% |
| 2003 | $5,011 +12.2% | $440,300 +9% |
| 2002 | $4,468 +23.8% | $404,000 +34.5% |
| 2000 | $3,608 -5.6% | $300,300 +15% |
| 1999 | $3,823 | $261,100 |
Find assessor info on the county website
Neighborhood: 01890
Nearby homes
- $1,888,6006 bd4 ba3.2k sqft157 Highland Ave, Winchester, MA 01890Off Market
- $1,300,0003 bd2 ba2.2k sqft49 Lincoln St, Winchester, MA 01890Sold
- $1,604,5003 bd2 ba3k sqft149 Highland Ave, Winchester, MA 01890Off Market
- $1,150,0004 bd2 ba2k sqft50 Lincoln St, Winchester, MA 01890Sold
- $1,468,0003 bd2 ba1.9k sqft45 Lincoln St, Winchester, MA 01890Off Market
- $7,5006 bd3 ba3.8k sqft161 Highland Ave, Winchester, MA 01890For Rent
- $1,200,0003 bd2 ba1.8k sqft147 Highland Ave, Winchester, MA 01890Sold
- $1,799,6003 bd3 ba3.2k sqft154 Highland Ave, Winchester, MA 01890Off Market
Nearby schools
GreatSchools rating
- 9/10Muraco Elementary SchoolGrades: K-5Distance: 0.4 mi
- 9/10McCall Middle SchoolGrades: 6-8Distance: 0.8 mi
- 10/10Winchester High SchoolGrades: 9-12Distance: 0.4 mi
Schools provided by the listing agent
- Elementary: Muraco
- Middle: Mccall
- High: Whs
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,968,800
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,968,800
- Massachusetts
- Middlesex County
- Winchester
- 01890
- 155 Highland Ave
