Winchester is one of the fastest-growing cities in Frederick County, known for its apple-themed events, historic downtown and accessibility to larger nearby cities. Famous country singer Patsy Cline was born and raised in Winchester, and her voice graced the local radio waves before her career took off. Though the city has changed since Patsy walked its streets, people continue to move in from neighboring Loudoun County and Washington D.C. for the small-town atmosphere, walkable streets and more affordable housing prices.
“There’s a lot of overflow from Loudoun County to Winchester for the affordability,” says Sherry Santmyer, an experienced Realtor with Hunt Country Sotheby's International Realty. “Also, a lot of retirees are moving there to settle down in retirement communities that are being built. Some people work in Winchester, but I’d say about 60% commute east toward the city. A lot of people work in Loudoun County, Fairfax County or D.C.”
The Apple Blossom Festival has been a tradition for 98 years.
Explore the home where Patsy’s journey began and celebrate her timeless legacy at The Patsy Cline House Museum in Winchester.
1/2
Working in Winchester or commuting to D.C.
Health care, retail and manufacturing jobs lead Winchester’s economy. Valley Health is one of the largest employers for the city and county, and the Winchester Medical Center is uniquely fitted to offer neonatal care and advanced surgeries.
Many commuters heading toward Northern Virginia and D.C. use Interstate 81 to connect onto Interstate 66 for the 75-mile trip east. U.S. Route 50 also guides drivers to Northern Virginia cities. Winchester Transit buses run on a fixed route, with stops at destinations like the Winchester Station shopping mall and Valley Health Winchester Medical Center. The Dulles International Airport is 50 miles east of the city and has connecting and direct flights.
Most places of worship in town are churches, but there are also a few synagogues close to downtown. Heavy rainfall can lead to minor flooding, primarily along roads throughout town. Otherwise, Winchester often sees humid summers and mild winters with some snow.
Valley Health is one of the largest employers for the city and county in Winchester.
The Dulles International Airport is a major hub convenient to Winchester.
1/2
Cheaper housing options than surrounding counties
Winchester’s median price is $419,900 while Leesburg in Loudoun County has a $1,020,000 median. Santmyer says people move to Winchester to get more for their money. Winchester’s median price is slightly above the $406,100 national median reported by the National Association of Realtors.
Historic homes near downtown Winchester can sell in the high $800,000s. Most homes have Craftsman or Colonial Revival designs and range between $400,000 and $600,000. “A lot of the homes I sell are in more rural areas on the outskirts of Winchester,” Santmyer says. “People want a little more land and more space. A lot of people like the Apple Pie Ridge area.”
Winchester Police releases five-year trend reports every month on their website. As of November 2024, the department has seen a decrease in nonviolent crimes and an increase in violent crimes. FBI data shows Winchester’s crime rates in 2023 were higher than state and national averages.
A cozy brick craftsman home adds character to the Winchester community.
Traditional charming brick colonial revival is inviting to the Winchester neigborhood.
1/2
Winchester goes all out for the Apple Blossom Festival
The biggest event of the year is the 10-day Shenandoah Apple Blossom Festival, which draws around 250,000 visitors to events all over town. “They have parades, and they bring in celebrities to be a part of the parades. The event has been going on forever, and it’s Winchester’s biggest festivity. We just had a house sell on the Apple Blossom route, and everyone wants to live on that route. People want to live there so they can sit on their front lawn and see the parade.”
On the weekends, locals can catch performances at several small theaters around town, from live music at the Bright Box Theater to plays organized by Shenandoah University students at the Ohrstrom-Bryant Theatre.
The Apple Blossom Festival draws very large crowds from around the region in Winchester.
Street food is abundant at the Apple Blossom Festival in Winchester.
1/2
Historic downtown and Apple Blossom Mall
Winchester residents have multiple choices when it comes to shopping and dining out. The Apple Blossom Mall has more than 60 stores, and Old Town Winchester is considered a walking mall because of its spread-out layout and walkable streets. “Downtown has shops and a lot of restaurants on the strip,” Santmyer says. “If you want to go to a really nice restaurant, you go downtown.” The downtown scene also has historic buildings that have been standing almost since the city was founded. Other shopping centers line Pleasant Valley Road.
The Winchester Farmers Market is open year-round on Tuesdays and Saturdays, and participating vendors all live within an hour of the city. Residents can support local farmers by picking up plants, produce and premium homemade goods.
Enjoy the finest artisan pizza in Winchester, made with fresh ingredients and bold flavors.
Apple Blossom Mall is the go-to destination in Winchester for fashion, fun, and family-friendly entertainment.
1/2
Living among the beauty of the Shenandoah National Park
Winchester is within the Shenandoah Valley, and that means residents are close to stunning outdoor destinations. Jim Barnett Park is the largest park in town, with paved walking trails, athletic fields and a lake stocked for fishing. Winchester also has the Museum of the Shenandoah Valley, where visitors can take self-guided tours around the historic grounds or explore the Glen Burnie House to learn about life in the valley. The Blue Ridge Mountains and the Shenandoah River State Park are about 25 miles south.
For a small town, Winchester offers a lot by way of history. Because of the city’s deep historical roots — six major Civil War battles took place in Winchester and the surrounding county — there are several museums and historical sites around town, including George Washington's Office and Stonewall Jackson’s Headquarters. The Patsy Cline Historic House is open seasonally to give visitors a glimpse into the star’s early home life and memorabilia from her career.
Enjoy a friendly game of Pickleball at Jim Barnett Park, largest park in Winchester.
Discover art, history, and breathtaking gardens at the Museum of the Shenandoah Valley in Winchester.
1/2
Public schools and Shenandoah University
Over 4,000 students attend Winchester City Public Schools, which Niche awards a B-plus. The district also runs the Emil & Grace Shihadeh Innovation Center, which partners with the Laurel Ridge Community College to teach students of any age the skills they need to enter the workforce. Shenandoah University is a private college that earns a B and is known for its liberal arts program and performing arts.
Shenandoah University is a hub of innovation, creativity, and academic excellence in the heart of Winchester.
John Handley High School stands as a historic symbol of learning and community pride in Winchester.
1/2
Written By
Rylee Doyle
Photography Contributed By
Joseph Furio
Video By
EB Fox
Interested in learning more about homes in this area?
Reach out to
Maija-Liisa Jano,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Winchester, VA sell after 40 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, VA over the last 12 months is $415,000, up 4% from the median home sale price over the previous 12 months.
Welcome to 435 Mikey Court, a beautifully appointed home tucked within the highly desirable Village at Harvest Ridge, a premier 55+ community offering comfort, quality, and ease of living. Designed for effortless main-level living, this home features a well-thought-out open floorplan that connects the living, dining, and kitchen spaces, creating a warm and inviting atmosphere with generous room
Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available!***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*MOVE-IN READY! The Bedford II 3 level interior town home
END UNIT Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available!***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*MOVE-IN READY! Explore Winchester’s new luxury
Charming 3-Bedroom Home in Historic Winchester, Virginia Discover this beautifully located 3-bedroom, 2-full bath home nestled in the heart of Historic Winchester. This residence boasts an exceptional location, just a short stroll away from the Old Town Mall, allowing you to enjoy local shops and dining. Positioned along the scenic Apple Blossom parade route, this home is perfect for anyone
Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for
Price improvement!! Experience Effortless 55+ Living at Winchester Landing – The Sapphire by Ryan Homes Discover the perfect blend of comfort and convenience in the Sapphire model, a spacious single-level condo offering over 1,500 sq. ft. of thoughtfully designed living space. The open-concept layout seamlessly connects a modern kitchen, large island, and bright great room, creating an inviting
Premium lot, ready to build on! This 8 acre parcel offers a rare combination of views, usable acreage, and convenience. Set approximately 800 feet off Cedar Creek Grade with frontage on Gough Road, the elevated homesite captures exceptional, wide-open mountain views and a peaceful, bucolic setting. Surrounded by farmland and in an area with attractive and newer, custom homes, this property feels
Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for
Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved
Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for
Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have some space between neighbors. Lots 7 & 8 are being sold
Welcome to 435 Mikey Court, a beautifully appointed home tucked within the highly desirable Village at Harvest Ridge, a premier 55+ community offering comfort, quality, and ease of living. Designed for effortless main-level living, this home features a well-thought-out open floorplan that connects the living, dining, and kitchen spaces, creating a warm and inviting atmosphere with generous room
The Rockford home design offers a thoughtful blend of modern functionality and classic comfort, perfect for homeowners who value both style and efficiency. With 4 bedrooms, 2 to 3 bathrooms, and 2,533 square feet of living space, the Rockford is an ideal choice for first-time buyers, growing families, or anyone looking to right-size their lifestyle.Step inside to find an inviting open-concept
Vacant Lot in Rolling HillsOne of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer
452 N Loudoun St Unit 102 is a 1 bed, 1 bath first floor apartment in Downtown Winchester just 4 blocks from the Walking Mall. Limited off street parking is available. The property has central heat and air. One pet is considered on a case-by-case basis. Pet deposit is $300. Monthly pet rent is $50 Landlord pays water, sewer, trash.Qualified tenants will have no previous evictions, no
**Showings to start Tuesday January 20th.**Welcome to 157-10 Brookland Terrace! This charming third-floor condo offers an open and airy living space with vaulted ceilings, skylights, and a cozy fireplace—perfect for relaxing. The updated kitchen features freshly painted cabinetry and newer appliances, including a refrigerator, built-in microwave, stove, dishwasher, and garbage disposal. Both
Charming Old Town location! Nestled in the heart of historic Old Town, this refreshed two-bedroom apartment offers an ideal urban living experience. The spacious layout is filled with natural light, with large windows creating a bright and airy atmosphere throughout. Conveniently located near shops, dining, and entertainment. Lease Requirements:Good credit and clean background check required.
Large 1-bedroom, 1-bathroom apartment located in the heart of Downtown Winchester, just steps from the Old Town Mall. This unit has been newly refreshed and is move-in ready. Convenient walkable location near shopping, dining, and entertainment. Rental Requirements:Tenant must have good credit and pass a clean background check. Restrictions:No smoking. No pets. No vaping.
Brand new and move-in ready, this attractive three-level end-unit townhome at 1801 Harvest Drive offers modern living in a fantastic Winchester location. Featuring a full brick front and additional sound insulation, this end unit provides both style and comfort. The entry level includes a one-car garage, a private bedroom, and a full bathroom, perfect for guests, a home office, or flexible living
About 2500 sqft. of completely updated DOWNSTAIRS apartment space in Downtown Winchester. All newer appliances, repainted, refinished wood floors. Sun Room, Porch, Dining room, Living room. even has some cedar closets! What more could you ask for in the heart of downtown Winchester. Landlord pays water, sewer, and all landscaping. Tenants must have minimum 650 Credit score. NO SMOKING.. NO PETS..
Charming Brand-New 4-Bedroom Home in Premier Winchester Community – Available for RentBedrooms: 4 | Bathrooms: 2.5 | Approx. 1,953 sq ft Welcome to your ideal rental home! Nestled in the desirable Retreat at Winding Creek community, this recently built (2025) single-family residence offers modern comfort, thoughtful design and excellent location. Interior HighlightsBright and open main
Charming 2-Bedroom Apartment – Prime Location Near Shenandoah University! This well-maintained 1-level apartment features 2 bedrooms and 1 full bathroom. Enjoy the convenience of a great location—just minutes from Shenandoah University, shopping, dining, and more! WASHER and Dryer in the unit!
Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage
Charming Furnished Historic 2-Bedroom Rental Just Two Blocks from the Loudoun Street Walking Mall! Live steps from downtown in this beautifully appointed duplex featuring 2-bedrooms and an additional small office/den upstairs. The home is full of historic character and modern comfort, boasting original hardwood floors, soaring ceilings, and timeless architectural charm throughout. Home can be
Welcome to this charming single-family home featuring 3 bedrooms and 1.5 baths in a prime Winchester location. The home offers durable LVP flooring throughout and a modern kitchen equipped with stainless steel appliances. Enjoy the convenience of both rear parking and ample street parking. Ideally located with easy access to Routes 7 and 81 and just minutes from downtown Winchester, shopping,
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
