Old Town
VA,Winchester
Average Sales Price
$559,900
Median Sales Price
$559,900
Population
4,601
Total Listings
1
Discover Life in Old Town with Barton Chasler
Local Perspective
If I were walking a client through Old Town, I’d tell you right away—this is the historic heart of Winchester, and it’s where the city’s story comes alive on every block. Having grown up just a short stroll from here, I know how Old Town’s blend of preserved character and evolving energy makes it a standout in our local market. I often recommend Old Town to clients who want more than just a place to live—they want to be connected to the community, to walkable streets, and to a sense of place you can’t replicate in newer developments. Whether you’re drawn to the architecture, the local businesses, or the parade routes that have shaped so many memories, Old Town is where Winchester’s past and present meet in the most personal way.
Neighborhood Highlights
Old Town exudes an unmistakable charm—think brick sidewalks, mature trees, and a rhythm that feels both lively and neighborly. The area buzzes with the activity of local shops, restaurants, and regular community events, yet there’s a peacefulness on the side streets that makes it feel like home. Unlike the newer subdivisions on the outskirts, Old Town offers a walkable lifestyle, with everything from morning coffee to evening concerts just steps away. The atmosphere is welcoming and diverse, appealing to everyone from young professionals to longtime residents who’ve watched the town evolve.
Homes & Architecture
Here, you’ll find a rich mix of historic homes—Victorian, Colonial, and Craftsman styles are common, with many properties dating back to the late 1800s and early 1900s. These homes often feature original hardwood floors, wide front porches, and unique architectural details that simply aren’t built today. While some houses have been lovingly restored, others offer opportunities for renovation and personalization. There are also a handful of converted lofts and smaller cottages tucked among the stately residences, giving buyers a range of options in size and character.
Demographics
Data provided by Attom Data
Population
Employment
Population
4.6K
4.6K in 2020
Density
9.2K
per square mile
Households
2.5K
16 With Children
Gender
47% / 53%
Men Vs Women
Occupancy
60% / 40%
Owned Vs Rented
Age Median: -- Years
No Data
Education Level
No Data
Educational Environment
Elementary Schools (3)Middle Schools (1)
Name
Category
Grades
Library
Ratio
7/10
Lyles-Crouch Elementary School
530 S Saint Asaph St, Alexandria, VA 22314
Public
KG - 5
No
15:1 STUDENTS/TEACHERS
0/10
St Mary's Elementary School
400 Green St, Alexandria, VA 22314
Private
PK - 8
Yes
9:1 STUDENTS/TEACHERS
0/10
St Pauls Nursery & Day School
228 S Pitt St, Alexandria, VA 22314
Private
PK - KG
Yes
4:1 STUDENTS/TEACHERS
Amenities & Attractions
Featured Listings
For Sale (1)
For Sold (7)
Active2 Beds3 Baths2,031 SqFt411-U105 N LOUDOUN ST #105, Winchester, VA 22601
MLS# VAWI2010920
Listed by MarketPlace REALTY
Old Town Living: Your Local FAQ Guide
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
What types of homes are found in Old Town?
Old Town is known for its historic charm, with a mix of lovingly preserved single-family homes, rowhouses, and some unique condos. Many properties date back decades, offering character you just don’t find in newer builds. If you appreciate architecture with a story, you’ll feel right at home here.
How is the commute and connectivity from Old Town?
What’s the lifestyle and walkability like in Old Town?
How quickly do homes sell in Old Town?
What should I know about schools in Old Town?
Are there HOA fees or special considerations?