5 bedroom homes for sale in Winchester, MA

22 hours on Rocket

$10,000 Closing Credit¹

$1,775,000

5 beds • 3.5 baths • 3,150 sqft

19 Pilgrim Dr, Winchester, MA 01890

#73389326, Gorfinkle Group, Listing office: eXp Realty

23 hours on Rocket

$10,000 Closing Credit¹

$2,250,000

5 beds • 5 baths • 5,000 sqft

1 Fox Hunt Ln, Winchester, MA 01890

#73389227, Leigh Ventura, Listing office: Compass

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5 days on Rocket

$10,000 Closing Credit¹

$1,389,000

5 beds • 2 baths • 1,706 sqft

35 Harvard St, Winchester, MA 01890

#73387036, Joanne Mulkerin, Listing office: J. Mulkerin Realty

7 days on Rocket

$3,175,000

5 beds • 4.5 baths • 5,386 sqft

21 Fernway, Winchester, MA 01890

#73385326, Kim Covino & Co. Team, Listing office: Compass

19 Laurel Hill Ln, Winchester, MA 01890 - view of front facade with a garage and brick siding

$2,550,000

5 beds • 4.5 baths • 3,800 sqft

19 Laurel Hill Ln, Winchester, MA 01890

#73385211, Mark Donnellan, Listing office: Advisors Living - Winchester

$10,000 Closing Credit¹

$2,050,000

5 beds • 3.5 baths • 3,874 sqft

4 Worthen Rd, Winchester, MA 01890

#73380697, Kim Covino & Co. Team, Listing office: Compass

Backup offers

$10,000 Closing Credit¹

$2,349,900

5 beds • 5 baths • 3,940 sqft

17 Wagon Wheel Rd, Winchester, MA 01890

#73380423, Dream Team, Listing office: Dreamega International Realty LLC

Room to negotiate?

Median Sold Price

$1.5M

Avg. Sale Time

27 Days

Based on our May 2025 Market Report.

$3,475,000

5 beds • 3.5 baths • 5,632 sqft

80 Arlington St, Winchester, MA 01890

#73372872, Carolyn Vernaglia, Listing office: Better Homes and Gardens Real Estate - The Shanahan Group

$2,899,000

5 beds • 4.5 baths • 6,904 sqft

11 Fieldstone Dr, Winchester, MA 01890

#73366222, Andersen Group Realty, Listing office: Keller Williams Realty Boston Northwest

$10,000 Closing Credit¹

$1,769,000

5 beds • 3.5 baths • 3,478 sqft

10 Olde Lyme Rd, Winchester, MA 01890

#73362881, Darryl Brian, Listing office: RE/MAX Bentley's

$10,000 Closing Credit¹

$1,449,900

5 beds • 2 baths • 3,033 sqft

7 Thornberry Rd, Winchester, MA 01890

#73362481, Salim Chowdhury, Listing office: TAJ Mahal Realty LLC

$2,899,000

5 beds • 5.5 baths • 4,627 sqft

11 Taft Dr, Winchester, MA 01890

#73359733, The Marrocco Group, Listing office: Coldwell Banker Realty - Lexington

$10,000 Closing Credit¹

$2,399,000

5 beds • 3.5 baths • 5,077 sqft

276 High St, Winchester, MA 01890

#73349101, Andersen Group Realty, Listing office: Keller Williams Realty Boston Northwest

$2,890,000

5 beds • 5 baths • 5,354 sqft

8 Chestnut St, Winchester, MA 01890

#73342518, The McLaren Team, Listing office: Compass

Winchester, MA Real Estate Market Overview

There are 14 5-bedroom homes for sale in Winchester, MA. The following market insights reflect all property types in the Winchester, MA real estate market. The number of homes in Winchester, MA increased by 23.8% between April 2025 and May 2025. While the average time on the market in May 2025 was 27 days, the median list price was $1,564,000. In May 2025 more than 6 listings in Winchester, MA were sold above the asking price. During the same period more than 5 listings were sold at asking price, while more than 7 were sold below.

From Rocket Homes Real Estate and based on county public records data

What is it like to live in Winchester, MA

Overview

Winchester is located in Middlesex County, Massachusetts. There are roughly 21,740 residents, living in 7,763 households. The average temperature for Winchester this time of the year is low of 56F and high of 77F. On average, Winchester gets about 3.72 inches of precipitation in June. Most residents are home owners (82%), have a post secondary degree (54%) and are married, with kids (36%).

Data provided by Home Junction

Schools near Winchester, MA

Elementary Schools

Muraco Elementary School
33 Bates Rd
Public District KG-5
Lincoln Elementary School
161 Mystic Valley Pkwy
Public District KG-5
Reeves Elementary School
240 Lexington St
Public District KG-5

Middle Schools

McCall Middle School
458 Main St
Public District 6-8

High Schools

Winchester High School
80 Skillings Rd
Public District 9-12

Data provided by Great Schools

5 bedroom homes for sale in Winchester, MA

Winchester, MA Real Estate Market Overview

What is it like to live in Winchester, MA

Overview

Schools near Winchester, MA

Housing market reports in Middlesex County

Homes for sale near Winchester, MA

Top real estate cities in Massachusetts