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Winchester

Winchester

Winchester, Massachusetts, is a charming suburban town located about eight miles north of downtown Boston, known for its scenic beauty and close-knit community. The town offers a variety of housing options, from historic Victorian homes to newer constructions, all set amidst tree-lined streets and expansive yards. The town’s natural beauty is on full display at the Mystic Lakes, where residents enjoy boating, fishing, and hiking, while its proximity to major highways and the MBTA commuter rail makes it an ideal choice for those commuting to Boston. In addition to its natural attractions and educational system, Winchester boasts a vibrant downtown area with an assortment of local shops, restaurants, and cafes. The town’s rich history is reflected in landmarks like the Winchester Town Hall and the James Hayden House, while Middlesex Fells offers additional outdoor recreation with scenic paths and bird-watching opportunities. Winchester's sense of community, combined with its easy access to Boston, makes it an appealing option for those seeking suburban living with a strong connection to the city. Whether enjoying outdoor activities, browsing local shops, or attending town events, Winchester provides a welcoming and peaceful environment for its residents.

Living in Winchester

Start your day with a stroll around Mystic Lakes, where the scenic views of the water and surrounding trees provide a calm and refreshing atmosphere. After your morning exercise, head to The Bagel Bar in downtown Winchester for a delicious breakfast. Enjoy a cup of freshly brewed coffee and a bagel, while soaking in the cozy, small-town vibe of this local favorite. Afterward, take a leisurely stroll through the downtown area, browsing the charming local shops, galleries, and boutiques that line the streets.


In the afternoon, you can enjoy more of Winchester’s natural beauty. Head over to Horn Pond for a relaxing walk along the trail, or perhaps even try a bit of birdwatching. If you’re looking for some cultural enrichment, explore the Winchester Town Hall or the Winchester Historical Society, where you can learn more about the town’s rich history. For lunch, visit one of the town’s casual dining spots like The Winchester Café, known for its fresh and healthy fare. The afternoon is the perfect time to enjoy Winchester’s blend of nature and community, whether you’re outdoors or enjoying the town’s local culture.


As the evening approaches, treat yourself to a quiet dinner at Ristorante Serena an upscale yet cozy spot offering Italian meals and a welcoming atmosphere. Afterward, catch a performance at the Winchester Community Theatre or enjoy a peaceful stroll through the tree-lined streets of the town, taking in the historic homes and serene surroundings. Living in Winchester provides a rare combination of peaceful suburban living, outdoor adventure, and a strong sense of community that makes every day feel connected and fulfilling.

The Real Estate Market

The real estate market in Winchester, Massachusetts, is highly desirable, known for its beautiful homes and proximity to Boston. Homes for sale in Winchester typically feature a mix of historic properties, charming Colonial-style homes, and more modern constructions, often set on spacious, tree-lined lots. Many properties offer expansive yards, manicured gardens, and picturesque surroundings, making the town an attractive choice for those looking for a more suburban lifestyle with easy access to the city. The town’s natural beauty and vibrant community continue to drive demand in this competitive market.

The market also sees interest in condos for sale in Winchester, as some buyers are drawn to the low-maintenance lifestyle these properties offer without compromising on space or location. With a mix of single-family homes, townhouses, and condos, Winchester provides a range of housing options to suit different needs and preferences. The combination of excellent amenities and proximity to Boston ensures that Winchester remains a sought-after destination for homebuyers looking to enjoy both suburban tranquility and city accessibility.

Overview for Winchester, MA

22,875 people live in Winchester, where the median age is 42.4 and the average individual income is $90,356. Data provided by the U.S. Census Bureau.

22,875

Total Population

42.4 years

Median Age

High

Population Density Population Density This is the number of people per square mile in a neighborhood.

$90,356

Average individual Income

Schools in Winchester, MA

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Primary Schools ()
Middle Schools ()
High Schools ()
Mixed Schools ()
The following schools are within or nearby Winchester. The rating and statistics can serve as a starting point to make baseline comparisons on the right schools for your family. Data provided by the U.S. Census Bureau.
Type
Name
Category
Grades
School rating

Homes in Allston/ Brighton Listings

Pending
MLS® 73341968

$4,799,000

19 Rangeley Rd, Winchester, MA 01890
5 Beds 7 Baths 7,779 Sq.Ft.
For Sale
MLS® 73344473

$4,399,000

26 Swan Road, Winchester, MA 01890
6 Beds 7 Baths 8,463 Sq.Ft.
Pending
MLS® 73334088

$4,200,000

3 Foxcroft Road, Winchester, MA 01890
6 Beds 6 Baths 5,208 Sq.Ft.
For Sale
MLS® 73328916

$4,199,000

6 Vinson Cir, Winchester, MA 01890
6 Beds 8 Baths 7,500 Sq.Ft.
For Sale
MLS® 73335471

$3,999,000

54 Johnson Road, Winchester, MA 01890
7 Beds 8 Baths 7,982 Sq.Ft.
For Sale
MLS® 73348642

$3,898,000

20 Amberwood Dr, Winchester, MA 01890
6 Beds 7 Baths 8,866 Sq.Ft.
For Sale
MLS® 73324581

$3,699,000

27 Everett Ave, Winchester, MA 01890
6 Beds 6 Baths 7,431 Sq.Ft.
For Sale
MLS® 73333668

$3,599,000

2 Chestnut St, Winchester, MA 01890
6 Beds 5 Baths 5,500 Sq.Ft.
For Sale
MLS® 73333712

$3,499,000

4 Norwood St, Winchester, MA 01890
5 Beds 5 Baths 5,250 Sq.Ft.

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399 Boylston St #200

Boston, MA 02116

Collin Fishman

(617) 982-3705

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