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$2,299,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,822 Sq. Ft.
  • 0.26 Acres
  • Updated 2 hours ago

Next open house:

Open House: 4:00 PM - 5:00 PM

Friday 5/1 4:00 PM - 5:00 PM

216 Highland Avenue,Winchester, MA 01890

216 Highland AvenueWinchesterMA01890

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Join us at 216 Highland Avenue on:

  • Open House: 11:00 AM - 12:30 PM

    Saturday 5/2 11:00 AM - 12:30 PM

    216 Highland Avenue,Winchester, MA 01890
    216 Highland AvenueWinchesterMA01890
  • Open House: 1:00 PM - 2:30 PM

    Sunday 5/3 1:00 PM - 2:30 PM

    216 Highland Avenue,Winchester, MA 01890
    216 Highland AvenueWinchesterMA01890
See This Home
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See This Home
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Welcome to this fully updated 5 BR, 3.5 BA Victorian showcasing elegant period detail throughout, including intricate woodwork, moldings, high ceilings & hardwood floors. The main level features a gourmet eat-in kitchen w/ quartz island & high-end stainless appliances, opening to a custom butler's pantry w/ additional oven, sink & wine chiller. A sun-filled family room w/French doors leads to the patio, along w/ a fireplaced living room w/ built-ins, & formal dining room. Home includes 2 primary bedroom options, one on the 2nd floor & a private 3rd-floor primary suite w/ fireplace & full bath. The 2nd level also has 3 additional spacious bedrooms & two full baths, while the 3rd floor features a dramatic great room w/ beamed ceiling.Additional highlights include partially finished basement & newer heat & AC. Enjoy a wrap-around porch, patio & large fenced yard. Ideally located near town center, Middlesex Fells Reservation, Commuter Rail, Lincoln Elementary, Middle School, & Highschool.

Full Property Details for 216 Highland Ave

General

  • Price: $2,299,000
  • Taxes: $22,931 (2026)
  • Status: Active
  • Type: Single Family
  • MLS ID: 73511014
  • Updated: Today (5/1/2026)
  • Added to Site: Today

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Bathroom 1: First
  • Bathroom 2: Second
  • Bathroom 3: Second

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Third
  • Bedroom 2: Second
  • Bedroom 3: Second
  • Bedroom 4: Second

Other Rooms

  • Living Room: First
  • Family Room: First
  • Kitchen: First
  • Dining Room: First

Parking

  • Parking Features: Off Street

Location

  • County: Middlesex

Structural Information

  • Architectural Style: Victorian
  • Basement: Yes
  • Square Feet: 4,822
  • Year Built: 1902

Lot Features

  • Lot Size (Acres): 0.26

Financial Considerations

  • Tax Amount: $22,931
  • Tax Year: 2026

Disclosures and Reports

  • Disclosures/Rstr.: No AC in basement. Basement and mudroom are heated by electric baseboard. Mudroom also features radiant heated flooring. Washer & Dryer are gifts to the buyers.
  • Property ID: 895385

Listed by Better Homes and Gardens Real Estate - The Shanahan Group, Paula R. Sughrue

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Listing agent

— 216 Highland Ave —

  • Paula R. Sughrue

    Better Homes and Gardens Real Estate - The Shanahan Group

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 216 Highland Ave

School District:Winchester School District, Winchester, MA
NameGradesDistance
Lincoln Elementary School, Winchester, MA
161 Mystic Valley Parkway, Winchester, MA 01890
K-50.4 mi
Mccall Middle School
458 Main Street, Winchester, MA 01890
6-80.5 mi
Winchester High School
80 Skillings Road, Winchester, MA 01890
9-120.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 216 Highland Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/01/2026
Listed
$2,299,000
109%
MLS
4/01/2002
Sold
$1,100,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 216 Highland Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$220
-99%
$1,984,300
—
2024
$22,429
4%
$1,979,600
8%
2023
$21,593
3%
$1,829,900
9%
2022
$20,957
5%
$1,675,200
8%
2021
$19,974
4%
$1,556,800
—
2020
$19,289
5%
$1,556,800
2%
2019
$18,444
2%
$1,523,000
3%
2018
$18,074
7%
$1,482,700
8%
2017
$16,871
11%
$1,373,900
5%
2016
$15,213
1%
$1,302,500
5%
2015
$15,020
3%
$1,237,200
8%
2014
$14,564
—
$1,150,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Better Homes and Gardens Real Estate - The Shanahan Group, Paula R. Sughrue

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216 Highland Avenue, Winchester, MA 01890 (MLS# 73511014) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 216 Highland Avenue is currently listed for $2,299,000 and was received on May 01, 2026. Want to learn more about 216 Highland Avenue? Do you have questions about finding other Single Family real estate for sale in Winchester Highlands? You can browse all Winchester Highlands real estate or contact a Coldwell Banker agent to request more information.

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