Winchester is the heart of the Shenandoah Valley — a city where history, charm, and growth all come together. Known for its vibrant downtown, famous apple blossoms, and mountain views in every direction, Winchester blends small-city energy with the friendliness of a close-knit community. Its location along I-81 and Route 7 makes it a favorite for commuters to Northern Virginia and D.C., while still offering the slower, scenic pace of Valley living.
The housing market here is as diverse as the city itself:
Historic homes downtown with timeless architecture and character.
Modern subdivisions with single-family homes and townhomes designed for today’s lifestyles.
Established neighborhoods with tree-lined streets and generous yards.
Rural properties and estates on the outskirts for those who crave wide-open space.
Winchester appeals to first-time buyers, families, and professionals alike, with affordable home values compared to Northern Virginia and a wide range of styles and price points.
Downtown Winchester is the city’s crown jewel. The Old Town Walking Mall is a pedestrian-friendly hub filled with restaurants, breweries, boutiques, and cultural venues like the Shenandoah Valley Discovery Museum and Bright Box Theater. Every spring, the city bursts into celebration with the world-famous Apple Blossom Festival, drawing visitors from near and far for parades, concerts, and community pride.
When it’s time to slow down, Winchester offers quick access to Shenandoah National Park, local vineyards, orchards, and farm markets. Outdoor lovers can hike, bike, or simply enjoy the breathtaking mountain backdrop.
Winchester is the oldest city west of the Blue Ridge Mountains, dating back to 1744.
The city changed hands over 70 times during the Civil War — more than any other town in America.
Country music legend Patsy Cline grew up in Winchester, and her childhood home is now a museum.
Winchester proudly holds the title of “Apple Capital of the World,” thanks to its deep roots in apple orchards and processing.
The historic Handley Library, built in 1913, is considered one of the most beautiful libraries in the country.
Winchester offers the perfect balance: rich history, a lively downtown, and a housing market that works for a wide range of buyers. It’s a city where neighbors gather for festivals, history lives on every corner, and the Shenandoah Valley’s natural beauty is always within reach. For homebuyers, Winchester isn’t just a place to live — it’s a place to belong.
29,385 people live in Winchester, where the median age is 36.8 and the average individual income is $36,256. Data provided by the U.S. Census Bureau.
Total Population
Median Age
Population Density Population Density This is the number of people per square mile in a neighborhood.
Average individual Income
There's plenty to do around Winchester, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.
Explore popular things to do in the area, including Matties Soft Serve Frozen Custard, Old Town Cidery, and Taqueria Los 7 Hermanos.
| Name | Category | Distance | Reviews |
Ratings by
Yelp
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|---|---|---|---|---|
| Dining | 1.29 miles | 5 reviews | 5/5 stars | |
| Dining | 1.07 miles | 5 reviews | 5/5 stars | |
| Dining | 2.75 miles | 8 reviews | 5/5 stars | |
| Dining · $$ | 0.25 miles | 14 reviews | 4.9/5 stars | |
| Shopping | 0.92 miles | 18 reviews | 4.9/5 stars | |
| Active | 2.07 miles | 5 reviews | 5/5 stars | |
| Active | 0.75 miles | 5 reviews | 5/5 stars | |
| Beauty | 0.75 miles | 11 reviews | 5/5 stars | |
| Beauty | 1.56 miles | 9 reviews | 5/5 stars | |
| Beauty | 2.33 miles | 7 reviews | 5/5 stars | |
| Beauty | 1.22 miles | 6 reviews | 5/5 stars | |
| Beauty | 0.8 miles | 5 reviews | 5/5 stars | |
| Beauty | 1.02 miles | 5 reviews | 5/5 stars | |
| Beauty | 0.99 miles | 5 reviews | 5/5 stars | |
| Beauty | 2.97 miles | 7 reviews | 5/5 stars | |
| Beauty | 0.46 miles | 11 reviews | 5/5 stars | |
| Beauty | 0.9 miles | 5 reviews | 5/5 stars | |
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Winchester has 11,843 households, with an average household size of 2.38. 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. 29,385 people call Winchester home. The population density is 3,006.21 and the largest age group is Data provided by the U.S. Census Bureau.
Total Population
Population Density Population Density This is the number of people per square mile in a neighborhood.
Median Age
Men vs Women
Population by Age Group
0-9 Years
10-17 Years
18-24 Years
25-64 Years
65-74 Years
75+ Years
Education Level
Total Households
Average Household Size
Average individual Income
Households with Children
With Children:
Without Children:
Marital Status
Blue vs White Collar Workers
Blue Collar:
White Collar:
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