Winchester


Located just north of Boston, the community of Winchester, Massachusetts is known for its great schools, vibrant downtown, excellent commuter rail access and outstanding neighborhoods. Like Lexington, its neighbor to the south, Winchester is an affluent bedroom community popular with professionals commuting to both Boston and Cambridge, and with families who desire to live within one of the state’s top educational systems.


Read More

Winchester Market Info

Average Price $1.5M
Lowest Price $500K
Highest Price $4.2M
Total Listings 37
Avg. Price/SQFT $528

Property Types (active listings)

Search Winchester Real Estate Listings for Sale

Click the links below to sort results by price range.

Sort by:
New
54 Johnson Rd, Winchester

$4,175,000

54 Johnson Rd, Winchester

7 Beds 8 Baths 7,982 SqFt Single Family MLS® # 72984802

Team Suzanne And Company Compass

10 Sheffield Rd, Winchester

$3,550,000

↓ $149,000

10 Sheffield Rd, Winchester

7 Beds 6 Baths 5,877 SqFt Single Family MLS® # 72978329

Andersen Group Realty Keller Williams Realty Boston Northwest

11 Niles Lane, Winchester

$3,299,000

↓ $100,000

11 Niles Lane, Winchester

5 Beds 6 Baths 7,103 SqFt Single Family MLS® # 72952069

Kim Covino & Co. Team Compass

17 Brooks Street, Winchester

$3,195,000

17 Brooks Street, Winchester

6 Beds 4 Baths 5,265 SqFt Single Family MLS® # 72974558

Michaela Pixie Mahtani Leading Edge Real Estate

New
3 Alice Lane, Winchester

$2,699,000

3 Alice Lane, Winchester

5 Beds 5 Baths 6,000 SqFt Single Family MLS® # 72986324

Kim Covino & Co. Team Compass

New
18 Olde Village Dr, Winchester

$2,500,000

18 Olde Village Dr, Winchester

5 Beds 6 Baths 5,370 SqFt Single Family MLS® # 72984717

Pauline Marino Berkshire Hathaway HomeServices Commonwealth Real Estate

22 Amberwood Drive, Winchester

$2,195,000

22 Amberwood Drive, Winchester

5 Beds 5 Baths 5,016 SqFt Single Family MLS® # 72984377

Beth Sager Group Keller Williams Realty Boston Northwest

11 Chesterford Road East, Winchester

$1,999,000

↓ $200,000

11 Chesterford Road East, Winchester

4 Beds 4 Baths 3,039 SqFt Single Family MLS® # 72981610

Kim Covino & Co. Team Compass

19 Edgehill Rd, Winchester

$1,999,000

19 Edgehill Rd, Winchester

5 Beds 3 Baths 3,624 SqFt Single Family MLS® # 72984295

Kim Covino & Co. Team Compass

8 Sachem Rd, Winchester

$1,499,000

8 Sachem Rd, Winchester

4 Beds 2 Baths 3,205 SqFt Single Family MLS® # 72983250

Matthew Winterle LAER Realty Partners/LAER LUX

15 Garfield Ave, Winchester

$1,349,900

↓ $25,100

15 Garfield Ave, Winchester

4 Beds 2 Baths 2,347 SqFt Single Family MLS® # 72975234

Kim Covino & Co. Team Compass

380 Highland Ave, Winchester

$1,329,000

380 Highland Ave, Winchester

4 Beds 3 Baths 2,633 SqFt Single Family MLS® # 72982187

Andersen Group Realty Keller Williams Realty Boston Northwest

Can't find the right listing for you? Register with the site to receive personalized Winchester real estate listings right in your mail box!

Winchester Community Information

During the most recent census of 2010, the population was approaching 22,000 residents.

<h2?More About Winchester Real Estate

Winchester has five elementary schools and one middle school. Considered one of Boston’s most elite public high schools, Winchester High School was founded in 1850 and continues to be a major draw to the community. Winchester public schools are consistently ranked by the Boston Magazine as one of the best systems in the state and the schools have achieved superior performances on the MCAS exams since their founding. Below is a list of the public schools that service Winchester’s youngest residents:

  • Ambrose Elementary
  • Lincoln Elementary
  • Lynch Elementary
  • Muraco Elementary
  • Vinson-Owen Elementary
  • McCall Middle School
  • Winchester High School

A predominantly Catholic community, as well as many of the communities that surround it, Winchester is also home to a number of parochial schools. St. Mary’s School, for example, was founded more than 134 years ago and is on the National Register of Historic Places. Similarly, the Children’s Own School is among the earliest surviving Montessori schools in the United States.

Winchester real estate presents a wealth of opportunities to today’s Boston homebuyers, and features everything from single-family homes to sprawling estate properties. Learn more and start your property search by connecting with the team at Terrier Real Estate today. They look forward to introducing you to Winchester and its excellent neighborhoods. Connect today!

With so much variety to offer, it’s easy to see why many homebuyers choose to make this lovely neighborhood their home. To start your real estate search in Winchester, contact Terrier Real Estate today! Their Boston REALTORS® are here to help.