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Winchester

If you’re looking at Winchester, you’re looking at the "Gold Standard" of the North Shore. It’s the ultimate blue-chip investment for buyers who want that high-end "garden city" vibe with a 15-minute commute into North Station.

Property Listings

Price

Living Area

For Sale

MLS® 73482952

Courtesy of The Pallotta Group with Gibson Sotheby's International Realty

The Academic Powerhouse: This is the #1 driver for the town’s massive property values. The school system is a perennial top-tier performer in the state. When you buy here, you’re essentially buying into a "recession-proof" school district that keeps your equity rock-solid and demand through the roof.
A "Real" Walkable Downtown: Unlike suburbs that are just a collection of cul-de-sacs, Winchester has a stunning, polished center. It feels like a movie set with the Wedgemere and Winchester Center train stops, local boutiques, and high-end dining. It’s that rare "commuter’s dream" where you can actually walk to the train and grab a coffee on the way.
The "Prestige" Aesthetic: People move here for the Victorian and Colonial architecture. It’s a town of tree-lined streets and historic estates that give it a sophisticated, "old money" charm. It has a similar "arrival" status to Wellesley but with a closer proximity to the city.
Outdoor Luxury: You’ve got the Middlesex Fells on one side and the Mystic Lakes on the other. Whether you’re into rowing, hiking, or just wanting that "green belt" feel, you get an elite outdoor lifestyle without sacrificing your urban access.
The "Town of Homes" Vibe: It’s a low-turnover, tight-knit community. People move here to put down roots for 20+ years. That scarcity of inventory means when a good house hits the market, it’s a feeding frenzy for high-net-worth buyers.

Winchester is a premier asset. You’re paying a premium to get in, but the ROI—both in lifestyle and long-term appreciation—is among the strongest in Greater Boston. It’s for the buyer who wants the best of everything: the schools, the commute, and the prestige.

Overview for Winchester, MA

22,862 people live in Winchester, where the median age is 43 and the average individual income is $104,586. Data provided by the U.S. Census Bureau.

22,862

Total Population

43 years

Median Age

High

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

$104,586

Average individual Income

Around Winchester, MA

There's plenty to do around Winchester, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.

65

Somewhat Walkable

Walking Score

54

Bikeable

Bike Score

Points of Interest

Explore popular things to do in the area, including Hodgkin's Spa, Alta Coffee Roasters, and Alta Coffee Roasters.

Name	Category	Distance	Reviews	Ratings by Yelp
Visit the Hodgkin's Spa page on Yelp Search 99 Holland St on Google Maps	Dining · $	3.81 miles	6 reviews	5/5 stars
Visit the Alta Coffee Roasters page on Yelp Search 805 Massachusetts Ave on Google Maps	Dining	2.51 miles	7 reviews	5/5 stars
Visit the Feet of a Dancer page on Yelp	Active	2.24 miles	12 reviews	5/5 stars
Visit the Mountain Strength Fitness page on Yelp Search 70 Cross St on Google Maps	Active	1.32 miles	11 reviews	5/5 stars
Visit the Radiant Beauty Aesthetics page on Yelp Search 21 Cummings Park Dr on Google Maps	Beauty	3.43 miles	7 reviews	5/5 stars
Visit the Eye Adore Threading page on Yelp Search 675 Mass Ave on Google Maps	Beauty	2.49 miles	5 reviews	5/5 stars

Demographics and Employment Data for Winchester, MA

Population Households Employment

Winchester has 8,054 households, with an average household size of 2.8. Data provided by the U.S. Census Bureau. Here’s what the people living in Winchester do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 22,862 people call Winchester home. The population density is 3,790.31 and the largest age group is Data provided by the U.S. Census Bureau.

22,862

Total Population

High

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

43

Median Age

47.53 / 52.47%

Men vs Women

Population by Age Group

0-9:

0-9 Years

10-17:

10-17 Years

18-24:

18-24 Years

25-64:

25-64 Years

65-74:

65-74 Years

75+:

75+ Years

Education Level

Less Than 9th Grade
High School Degree
Associate Degree
Bachelor Degree
Graduate Degree

8,054

Total Households

2.8

Average Household Size

$104,586

Average individual Income

Households with Children

With Children:

Without Children:

Marital Status

Married

Single

Divorced

Separated

Blue vs White Collar Workers

Blue Collar:

White Collar:

Commute Time

0 to 14 Minutes

15 to 29 Minutes

30 to 59 Minutes

60+ Minutes

Schools in Winchester, MA

All ()

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

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Winchester

Property Listings

$4,699,000

$3,750,000

$3,747,000

$3,650,000

$3,600,000

$3,499,000

$3,400,000

$3,399,000

$3,390,000

Overview for Winchester, MA

22,862

43 years

High

$104,586

Around Winchester, MA

65

Somewhat Walkable

54

Bikeable

Points of Interest

Demographics and Employment Data for Winchester, MA

22,862

High

43

47.53 / 52.47%

8,054

2.8

$104,586

Schools in Winchester, MA

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