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.


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Winchester Market Info

Average Price $1.5M
Lowest Price $310K
Highest Price $4.2M
Total Listings 40
Avg. Price/SQFT $512

Property Types (active listings)

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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

17 Brooks Street, Winchester

$2,995,000

17 Brooks Street, Winchester

6 Beds 4 Baths 5,265 SqFt Single Family MLS® # 73033237

Michaela Pixie Mahtani Leading Edge Real Estate

16 Chestnut Street, Winchester

$2,849,000

↓ $150,000

16 Chestnut Street, Winchester

6 Beds 5 Baths 6,100 SqFt Single Family MLS® # 73033839

Kim Covino & Co. Team Compass

14 Nassau Dr, Winchester

$2,499,000

14 Nassau Dr, Winchester

6 Beds 7 Baths 5,268 SqFt Single Family MLS® # 73032962

Weidong Li WINN Real Estate & Consulting

4 Davey Ln, Winchester

$2,450,000

4 Davey Ln, Winchester

5 Beds 5 Baths 5,402 SqFt Single Family MLS® # 73022155

Dave White OwnerEntry.com

1 Aricia Lane, Winchester

$2,399,888

↓ $99,112

1 Aricia Lane, Winchester

4 Beds 5 Baths 6,165 SqFt Single Family MLS® # 73010137

Vita Realty Group Compass

39 Everett Avenue, Winchester

$2,300,000

39 Everett Avenue, Winchester

5 Beds 4 Baths 3,769 SqFt Single Family MLS® # 73037552

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

2 Reservoir Street, Winchester

$2,180,000

2 Reservoir Street, Winchester

5 Beds 4 Baths 4,267 SqFt Single Family MLS® # 73027354

Pirani & Wile Group Leading Edge Real Estate

6 Cambridge Street, Winchester

$2,000,000

↓ $195,000

6 Cambridge Street, Winchester

4 Beds 4 Baths 4,374 SqFt Single Family MLS® # 73021604

Karen Bernier Churchill Properties

195 Cambridge St, Winchester

$1,999,900

195 Cambridge St, Winchester

4 Beds 4 Baths 3,528 SqFt Single Family MLS® # 73015208

Jonathan Dasilva EVO Real Estate Group, LLC

6 Gershon Way #6, Winchester

$1,999,000

↓ $101,000

6 Gershon Way #6, Winchester

3 Beds 4 Baths 3,995 SqFt Condominium MLS® # 73018402

The Marrocco Group Coldwell Banker Realty - Winchester

17 Lochwan St, Winchester

$1,988,000

17 Lochwan St, Winchester

4 Beds 3 Baths 3,293 SqFt Single Family MLS® # 73029533

Yan Rong United Real Estate, LLC

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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.