216 Highland Ave, Winchester, MA 01890
Home value
$2,525,900
$2.30M - $2.78M
$7,815/mo
Owner options
$7,815/mo
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$7,815/mo
Rent Zestimate®
$15,091/mo
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$15,091/mo
Est. payment
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Zillow last checked:
Listing updated:
Paula R. Sughrue 781-526-7079,
Better Homes and Gardens Real Estate - The Shanahan Group 781-729-9030
Elizabeth Damon
Donnelly + Co.
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: Ceiling Fan(s), Walk-In Closet(s), Flooring - Hardwood, Lighting - Sconce, Lighting - Overhead, Crown Molding, Decorative Molding
- Level: Third
Bedroom 2
- Features: Closet, Flooring - Hardwood, Lighting - Overhead, Crown Molding, Decorative Molding, Tray Ceiling(s)
- Level: Second
Bedroom 3
- Features: Closet, Flooring - Hardwood, Lighting - Overhead, Crown Molding, Decorative Molding
- Level: Second
Bedroom 4
- Features: Closet, Flooring - Hardwood, Lighting - Overhead, Crown Molding, Decorative Molding
- Level: Second
Bedroom 5
- Features: Closet, Lighting - Overhead, Crown Molding, Decorative Molding
- Level: Second
Primary bathroom
- Features: Yes
Bathroom 1
- Features: Bathroom - Half, Flooring - Stone/Ceramic Tile, Remodeled, Lighting - Sconce, Crown Molding
- Level: First
Bathroom 2
- Features: Bathroom - Full, Flooring - Marble, Countertops - Stone/Granite/Solid
- Level: Second
Bathroom 3
- Features: Bathroom - Full, Flooring - Stone/Ceramic Tile
- Level: Second
Dining room
- Features: Closet/Cabinets - Custom Built, Flooring - Hardwood, Lighting - Overhead, Crown Molding, Pocket Door
- Level: First
Family room
- Features: Flooring - Hardwood, Window(s) - Picture, French Doors, Chair Rail, Exterior Access, Recessed Lighting, Crown Molding
- Level: First
Kitchen
- Features: Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Dining Area, Countertops - Stone/Granite/Solid, Countertops - Upgraded, Kitchen Island, Exterior Access, Recessed Lighting, Stainless Steel Appliances, Wine Chiller, Gas Stove, Lighting - Pendant, Crown Molding
- Level: First
Living room
- Features: Closet/Cabinets - Custom Built, Flooring - Hardwood, French Doors, Exterior Access, Lighting - Overhead, Crown Molding, Pocket Door
- Level: First
Heating
- Forced Air, Electric Baseboard, Radiant, Natural Gas
Cooling
- Central Air
Appliances
- Included: Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer, Wine Refrigerator
- Laundry: Sink, In Basement
Features
- Bathroom - Full, Bathroom - Double Vanity/Sink, Countertops - Stone/Granite/Solid, Soaking Tub, Closet, Closet/Cabinets - Custom Built, Countertops - Upgraded, Recessed Lighting, Peninsula, Beamed Ceilings, Lighting - Overhead, Bathroom, Play Room, Great Room, Wet Bar
- Flooring: Tile, Carpet, Laminate, Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
- Doors: Pocket Door, French Doors
- Windows: Picture
- Basement: Full,Partially Finished,Bulkhead
- Number of fireplaces: 2
- Fireplace features: Living Room, Master Bedroom
Interior area
- Total structure area: 4,822
- Total interior livable area: 4,822 sqft
- Finished area above ground: 3,395
- Finished area below ground: 1,427
Property
Parking
- Total spaces: 5
- Parking features: Off Street
- Uncovered spaces: 5
Features
- Patio & porch: Porch, Patio
- Exterior features: Porch, Patio, Rain Gutters, Professional Landscaping, Sprinkler System, Fenced Yard
- Fencing: Fenced/Enclosed,Fenced
Lot
- Size: 0.26 Acres
Details
- Parcel number: 895385
- Zoning: RDB
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Victorian
- Property subtype: Single Family Residence
Materials
- Foundation: Stone
- Roof: Slate
Condition
- Year built: 1902
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Public Transportation, Shopping, Park, Medical Facility, Conservation Area, Highway Access, Public School, T-Station
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $498/sqft
- Tax assessed value: $2,015,000
- Annual tax amount: $22,931
- Date on market: 6/17/2026
Price history
| Date | Event | Price |
|---|---|---|
| 6/30/2026 | Sold | $2,400,000+4.4%$498/sqft |
Source: MLS PIN #73511014 Report a problem | ||
| 6/28/2026 | Pending sale | $2,299,000$477/sqft |
Source: MLS PIN #73511014 Report a problem | ||
| 5/7/2026 | Contingent | $2,299,000$477/sqft |
Source: MLS PIN #73511014 Report a problem | ||
| 5/1/2026 | Listed for sale | $2,299,000+109%$477/sqft |
Source: MLS PIN #73511014 Report a problem | ||
| 4/1/2002 | Sold | $1,100,000+69.2%$228/sqft |
Source: Public Record Report a problem | ||
| 4/13/2000 | Sold | $650,000$135/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $22,006 -1.9% | $1,984,300 +0.2% |
| 2024 | $22,429 +3.9% | $1,979,600 +8.2% |
| 2023 | $21,593 +3% | $1,829,900 +9.2% |
| 2022 | $20,957 +4.9% | $1,675,200 +7.6% |
| 2021 | $19,974 +3.6% | $1,556,800 |
| 2020 | $19,289 +4.6% | $1,556,800 +2.2% |
| 2019 | $18,444 +2% | $1,523,000 +2.7% |
| 2018 | $18,074 +7.1% | $1,482,700 +7.9% |
| 2017 | $16,871 +10.9% | $1,373,900 +5.5% |
| 2016 | $15,213 +1.3% | $1,302,500 +5.3% |
| 2015 | $15,020 +3.1% | $1,237,200 +7.5% |
| 2014 | $14,564 +9.9% | $1,150,400 +10.8% |
| 2013 | $13,254 +1.8% | $1,037,900 |
| 2012 | $13,026 +4.8% | $1,037,900 +1% |
| 2011 | $12,432 -1.5% | $1,027,400 -6.3% |
| 2010 | $12,625 +2.1% | $1,096,900 |
| 2009 | $12,362 +4.8% | $1,096,900 -1.7% |
| 2008 | $11,791 +5.8% | $1,115,500 +3.4% |
| 2007 | $11,144 +1.2% | $1,078,800 +1.6% |
| 2006 | $11,009 +2.1% | $1,061,600 +2.6% |
| 2005 | $10,781 -3% | $1,034,600 +6% |
| 2004 | $11,109 +2.5% | $976,200 +2.5% |
| 2003 | $10,836 +22.1% | $952,200 +18.7% |
| 2002 | $8,876 +80% | $802,500 +65.1% |
| 2000 | $4,931 -5.6% | $486,100 +36.2% |
| 1999 | $5,224 | $356,800 |
Neighborhood: 01890
Nearby homes
- $2,072,1003 bd3 ba3.9k sqft208 Highland Ave, Winchester, MA 01890Off Market
- $2,303,4004 bd3 ba3.9k sqft6 Wolcott Rd, Winchester, MA 01890Off Market
- $1,470,9004 bd1 ba2.8k sqft220 Highland Ave, Winchester, MA 01890Off Market
- $2,362,1004 bd3 ba3.9k sqft12 Wolcott Rd, Winchester, MA 01890Off Market

- $1,808,6008 bd4 ba3.7k sqft217 Highland Ave, Winchester, MA 01890Off Market
- $1,623,8004 bd1 ba1.9k sqft2 Wolcott Rd, Winchester, MA 01890Off Market
- $1,955,3005 bd4 ba4.5k sqft211 Highland Ave, Winchester, MA 01890Off Market
- $2,203,9004 bd4 ba3.5k sqft10 Wolcott Rd, Winchester, MA 01890Off Market
Nearby schools
GreatSchools rating
- 9/10Lincoln Elementary SchoolGrades: K-5Distance: 0.4 mi
- 9/10McCall Middle SchoolGrades: 6-8Distance: 0.5 mi
- 10/10Winchester High SchoolGrades: 9-12Distance: 0.3 mi
Schools provided by the listing agent
- Elementary: Lincoln
- Middle: Mccall
- High: Winchester High
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Massachusetts
- Middlesex County
- Winchester
- 01890
- 216 Highland Ave