The Local
230 Spring St,
Winchester, VA 22601
$1,700 - $2,400 | 1-4 Beds
Downtown Winchester
Winchester, VA
Downtown Winchester - Winchester, VA
Area Guide
Live where greatness reigns
Walkable
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Historic
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Nightlife
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Festivals
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Events
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University
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Museums
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Art
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Culture
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With a history dating back to the first Quaker settlers arriving around 1729, historic Downtown Winchester provides more than 40 block of history. Also called Old Town, the narrow cobblestone roads and colonial architecture lead past elegant boutiques and cafes. The pedestrian mall along Loudoun Street provides charming sidewalk cafes and shops in a beautiful setting. Downtown Winchester is very walkable and the destinations are plentiful.
Fort Loudoun Historic Site served as George Washington's headquarters during the French and Indian War, George Washington's Office Museum dates back to 1755, and Stonewall Jackson's Headquarters Museum was used by the general during the winter of 1861. Other historic landmarks include the Patsy Cline Historic House, the Francis Barton Event Center, the Museum of the Shenandoah Valley, and the Shenandoah Valley Civil War Museum.
Living in Downtown Winchester isn't just about the history. This neighborhood is home to the Old Town Farmers Market, terrific restaurants, nightlife, and a variety of festivals and events including the Shenandoah Apple Blossom Festival, the Bluemont Summer Concert Series, and the First Fridays Celebration of the Arts. Downtown Winchester is convenient to the Apple Blossom Mall, Shenandoah University, and the Winchester Regional Airport.
Rent Trends
As of April 2025, the average apartment rent in Downtown Winchester is $1,474 for one bedroom, $1,656 for two bedrooms, and $1,917 for three bedrooms. Apartment rent in Downtown Winchester has increased by 1.8% in the past year.
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1 BR
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682 sq ft
Average Sq Ft
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$1,474/month
Average Rent
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2 BR
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1,115 sq ft
Average Sq Ft
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$1,656/month
Average Rent
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3 BR
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1,219 sq ft
Average Sq Ft
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$1,917/month
Average Rent
Transportation
79
Very Walkable
out of 100 WalkScore® Rating
If you enjoy walking, you’ll enjoy renting in this area! It’s a very walkable neighborhood.
49
Bikeable
out of 100 BikeScore® Rating
While there’s some bike infrastructure in this area, you’ll still need a car for many errands.
Points of Interest
Shopping Centers
Parks and Recreation
- Shenandoah Valley Discovery Museum
- Museum of the Shenandoah Valley
- Hedgebrook Farms
Commuter Rail
Military Bases
Colleges
Top Apartments in Downtown Winchester
Houses for Rent in Downtown Winchester
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Methodology
† Our analysis of utilities, groceries, transportation, healthcare, home prices, and other goods and services is sourced from the Cost of Living Index, a respected benchmark published by the Council for Community and Economic Research (C2ER) that provides a thorough overview of living expenses across different regions.
Rent data is provided by CoStar Group’s Market Trend reports. As the industry leader in commercial real estate information, analytics, and news, CoStar conducts extensive research to produce and maintain a comprehensive database of commercial real estate information. We combine this data with public record to provide the most up-to-date rental information available.
Consumer goods, services, and home prices are sourced from the Cost of Living Index published by the Council for Community and Economic Research (C2ER). The data on this page is updated quarterly. It was last published in February 2025.