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 $2.1M
Lowest Price $679K
Highest Price $6.5M
Total Listings 50
Avg. Price/SQFT $539

Property Types (active listings)

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15&lot227 Vinson Circle, Winchester

$6,500,000

15&lot227 Vinson Circle, Winchester

6 Beds 6.5 Baths 8,805 SqFt Residential MLS® # 73134071

Anthony Marino The Marino Group Collection

25 Ledgewood Rd, Winchester

$5,800,000

25 Ledgewood Rd, Winchester

7 Beds 4.5 Baths 4,231 SqFt Residential MLS® # 73159196

Karen S. Garrett Better Homes and Gardens Real Estate - The Shanahan Group

8 Niles Lane, Winchester

$5,200,000

↓ $399,000

8 Niles Lane, Winchester

8 Beds 7.5 Baths 7,497 SqFt Residential MLS® # 73083677

Kim Covino & Co. Team Compass

19 Socrates Way, Winchester

$3,299,000

19 Socrates Way, Winchester

5 Beds 5 Baths 5,678 SqFt Residential MLS® # 73156754

Lucille Murray Compass

11 Brooks St., Winchester

$3,099,000

11 Brooks St., Winchester

5 Beds 4.5 Baths 5,208 SqFt Residential MLS® # 73158209

Michaela Pixie Mahtani Leading Edge Real Estate

30 Wedgemere Avenue, Winchester

$2,975,000

↓ $225,000

30 Wedgemere Avenue, Winchester

5 Beds 4.5 Baths 4,263 SqFt Residential MLS® # 73120584

Kim Covino & Co. Team Compass

319 Main St, Winchester

$2,899,900

↓ $99,100

319 Main St, Winchester

8 Beds 6 Baths 6,484 SqFt Residential MLS® # 73112247

Leeman & Gately Compass

10 North Gateway, Winchester

$2,899,000

10 North Gateway, Winchester

5 Beds 5.5 Baths 6,067 SqFt Residential MLS® # 73158946

Vita Realty Group Compass

1 Alice Lane, Winchester

$2,799,000

1 Alice Lane, Winchester

5 Beds 5 Baths 5,000 SqFt Residential MLS® # 73107072

Kim Covino & Co. Team Compass

228 Ridge St, Winchester

$2,725,000

228 Ridge St, Winchester

5 Beds 5.5 Baths 6,265 SqFt Residential MLS® # 73152537

Pirani & Wile Group Leading Edge Real Estate

20 Bellevue Avenue, Winchester

$2,699,000

20 Bellevue Avenue, Winchester

6 Beds 6.5 Baths 6,300 SqFt Residential MLS® # 73160636

Kim Covino & Co. Team Compass

18 Middlesex St, Winchester

$2,650,000

18 Middlesex St, Winchester

4 Beds 4.5 Baths 5,233 SqFt Residential MLS® # 73147332

Candice Macoul Luxury Living Real Estate

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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.