216 Highland Avenue Winchester, MA ^$ 2,299,000

216 Highland Avenue

^$ 2,299,000

Back to search

Recently Listed

Open House 5/1 4pm - 5pm

216 Highland Avenue

Winchester, MA, 01890

^$ 2,299,000

Bedrooms5 Baths3.1 Sq 4,822

Monthly Estimate*

^$ 14,155

216 Highland Avenue, Winchester, MA 01890 - Image 1

216 Highland Avenue, Winchester, MA 01890 - Image 2

216 Highland Avenue, Winchester, MA 01890 - Image 3

216 Highland Avenue, Winchester, MA 01890 - Image 4

216 Highland Avenue, Winchester, MA 01890 - Image 5

216 Highland Avenue, Winchester, MA 01890 - Image 6

216 Highland Avenue, Winchester, MA 01890 - Image 7

216 Highland Avenue, Winchester, MA 01890 - Image 8

216 Highland Avenue, Winchester, MA 01890 - Image 9

216 Highland Avenue, Winchester, MA 01890 - Image 10

216 Highland Avenue, Winchester, MA 01890 - Image 11

216 Highland Avenue, Winchester, MA 01890 - Image 12

216 Highland Avenue, Winchester, MA 01890 - Image 13

216 Highland Avenue, Winchester, MA 01890 - Image 14

216 Highland Avenue, Winchester, MA 01890 - Image 15

216 Highland Avenue, Winchester, MA 01890 - Image 16

216 Highland Avenue, Winchester, MA 01890 - Image 17

216 Highland Avenue, Winchester, MA 01890 - Image 18

216 Highland Avenue, Winchester, MA 01890 - Image 19

216 Highland Avenue, Winchester, MA 01890 - Image 20

216 Highland Avenue, Winchester, MA 01890 - Image 21

216 Highland Avenue, Winchester, MA 01890 - Image 22

216 Highland Avenue, Winchester, MA 01890 - Image 23

216 Highland Avenue, Winchester, MA 01890 - Image 24

216 Highland Avenue, Winchester, MA 01890 - Image 25

216 Highland Avenue, Winchester, MA 01890 - Image 26

216 Highland Avenue, Winchester, MA 01890 - Image 27

216 Highland Avenue, Winchester, MA 01890 - Image 28

216 Highland Avenue, Winchester, MA 01890 - Image 29

216 Highland Avenue, Winchester, MA 01890 - Image 30

216 Highland Avenue, Winchester, MA 01890 - Image 31

216 Highland Avenue, Winchester, MA 01890 - Image 32

216 Highland Avenue, Winchester, MA 01890 - Image 33

216 Highland Avenue, Winchester, MA 01890 - Image 34

216 Highland Avenue, Winchester, MA 01890 - Image 35

216 Highland Avenue, Winchester, MA 01890 - Image 36

216 Highland Avenue, Winchester, MA 01890 - Image 37

216 Highland Avenue, Winchester, MA 01890 - Image 38

216 Highland Avenue, Winchester, MA 01890 - Image 39

216 Highland Avenue, Winchester, MA 01890 - Image 40

216 Highland Avenue, Winchester, MA 01890 - Image 41

216 Highland Avenue, Winchester, MA 01890 - Image 42

Single Family Home for sale in Winchester, MA

for $2,299,000 with 5 bedrooms and 3 full baths, 1 half bath. This 4,822 square foot home was built in 1902 on a lot size of 0.26.

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.

Open House

5/1/2026 4:00 PM - 5:00 PM

5/2/2026 11:00 AM - 12:30 PM

5/3/2026 1:00 PM - 2:30 PM

216 Highland Avenue Winchester, MA

* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

^$ 2,299,000

Bedrooms

Full Bath

Half Bath

Property Type

Single Family

Taxes

^$ 22,931

Style

Victorian

Lot Size

0.26

Year Built

1902

Town/City

Winchester

County/Region

Middlesex

MLS | Web ID

73511014

List By

Paula R. Sughrue

Listing Agent

Better Homes And Gardens Real Estate - The Shanahan Group

Broker

Affordability Calculator

$16,066

Per Month

Monthly Principal & Interest: $14,155
Monthly Property Taxes: $1,911
Monthly Home Insurance: --

Set your offer price

Down Payment

Loan Term

Interest Rate

Yearly Property Taxes

Yearly Home Insurance

Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

THE TIME TO SELL IS NOW! What's my home worth?

Nearby

Trends

Single family listings in Winchester, MA

Average List Price ^$2,434,547

Percent of Sale Price 6%

About Winchester, MA

22,228 Population

7% Since 2002

^$152,119 Median Income

45.68 Median Age

42% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

Neighborhood & Schools

MLS Property Information Network, Inc rules require that you sign in here to see more detail on this property.

Pricing History

Date	Price	Price Change	Description
5/1/2026	$2,299,000		Listed Price

Map

More homes like this one

homes for you

See all

216 Highland Avenue, Winchester, MA, 01890 is a Single Family Home for sale at $2,299,000 with 4,822 sqft and a lot size of 0.26. 216 Highland Avenue has 5 bedrooms, 3.1 baths, and was built in 1902. The property's zip code is 01890 which is in Winchester, MA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Data is updated as of 5/1/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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 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 or leasing 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 or leasing. 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.

*Full Name

*Email

*Phone

I am interested in financing options

Get more info

By submitting the form, you agree that Weichert^® may contact you via phone or text about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our privacy policy.

Get more info

Looking for an Associate?

Already Working with an Associate?

216 Highland Avenue

Single Family Home for sale in Winchester, MA

Open House

Affordability Calculator

Neighborhood & Schools

Map

More homes like this one

Get more info about this home