158 Highland Ave
Winchester, MA 01890
5 bd 4 ba 4,400 sqft Built 1900 Lot 24,394 sqft single_family
No recorded sales
Location
Timeline: Sale, Listing & Tax History
Recorded events
No recorded events
No sale or listing events are on file for this property.
Tax assessment history
| Year | Building | Land | Total assessed | Tax paid |
|---|---|---|---|---|
| 2025 | $923,200 | $1,082,700 | $2,005,900 | $22,245 |
| 2023 | $920,800 | $1,082,700 | $2,003,500 | $21,642 |
| 2022 | $833,500 | $842,500 | $1,676,000 | $20,967 |
| 2021 | $833,500 | $702,500 | $1,536,000 | $19,707 |
| 2020 | $826,800 | $702,500 | $1,529,300 | $18,948 |
| 2019 | $812,800 | $662,500 | $1,475,300 | $17,866 |
| 2018 | $793,500 | $640,500 | $1,434,000 | $17,480 |
| 2016 | $666,100 | $640,500 | $1,306,600 | $15,261 |
| 2015 | $610,100 | $582,500 | $1,192,600 | $14,478 |
| 2014 | $610,000 | $487,500 | $1,097,500 | $13,894 |
| 2006 | $633,300 | $391,000 | $1,024,300 | $10,622 |
| 2005 | $633,300 | $359,000 | $992,300 | $10,340 |
| 2004 | $610,200 | $327,000 | $937,200 | $10,665 |
| 2003 | $594,900 | $317,400 | $912,300 | $10,382 |
Property facts
Year built
1900
Property type
single_family
Stories
1
Beds
5
Baths
4
Living area
4,400 sqft
Lot size
24,394 sqft
ZIP code
01890
City
Winchester
Street
Highland Ave
Coordinates
42.45858, -71.12568
Comparable properties nearby
Block-level micro-comps
Same street, ±3 house numbers, sold in the last 24 monthsFrequently asked questions
When did 158 Highland Ave last sell?
No public-record sale is on file for 158 Highland Ave.
What is the current tax assessment for 158 Highland Ave?
The most recent total assessment for 158 Highland Ave (year 2025) is $2,005,900 with $22,245 in property tax.
When was 158 Highland Ave built?
158 Highland Ave was built in 1900.
How does 158 Highland Ave compare to others on Highland Ave?
We track 8 other properties on Highland Ave. Browse the list under "Other properties on Highland Ave" to compare beds, baths, and sale history.
What are the property facts for 158 Highland Ave?
158 Highland Ave is a 5 bed, 4 bath, 4,400 sqft, 24,394 sqft lot single_family.
Is 158 Highland Ave a flip candidate?
No — 158 Highland Ave does not appear in our flips dataset.
Is 158 Highland Ave a tax-appeal candidate?
No — 158 Highland Ave is not currently flagged as a tax-appeal candidate.
Forecast for this area
ZIP-area linear projection — not a per-property automated valuationQuarterly trend
+1.1%
Implied 1-yr
+4.5%
2026 Q2
$1.94M
2026 Q3
$1.96M
ZIP 01890 — Median Price History + Forecast
Explore nearby
Geography
Other properties on Highland Ave