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Winchester City Real Estate Search

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Winchester City Homes and Condos for Sale

Winchester City, Virginia is the county seat of Frederick County. Old Town Winchester is at the heart of the National Register Historic District and has been an important marketplace for over 250 years. This historic section of Winchester not only cherishes its heritage but welcomes people with grace and style to enjoy the Loudoun Street Pedestrian Mall, outdoor cafes, shops and historical attractions. A genuine main street community, Old Town Winchester offers access to a variety of restaurants, shops, and public services. Day to day living exists within walking distance or by public transportation. Winchester City is dedicated to providing a vibrant, sustainable community with constant improvements for its citizens.

Celebrating history in Old Town Winchester can be accomplished through the many museums located in the historic district. One of those is the Old Courthouse Civil War Museum. Many of these museums can be found within walking distance of each other. Find a parking spot and spend the day walking through the historic district to learn about Winchester City’s history. You will find equal importance given to arts and entertainment. Many annual activities are held in Old Town Winchester which gives people the opportunity to experience the arts. Some of these include the First Fridays Celebration of the Arts, a summer series of outdoor movies, the Bluemont Summer Concert Series, Christmas and New Year’s Eve celebrations, and Winchester Little Theatre. Recognizing the impact of farming is also found in Winchester. From May to September, the Old Town Farmers Market gives vendors the opportunity to sell seasonal fruits and vegetables, baked goods, cheeses, beef, condiments, eggs and other items.

Winchester City real estate offers a combination of traditional homes in Old Town, ranches, Cape Cod, Federal, and Victorian homes as well as newer homes in Winchester neighborhoods. The lawns are well-maintained and mature trees are plentiful. Many of the newer homes have been designed to fit into the traditional style of the area. The students are served by the Winchester Public Schools, providing high-quality education in four elementary schools, one middle school, and one high school. The restaurants and bars are favorites for Winchester nightlife. With the natural beauty of the area, the rich history, and the many unique shops and family-oriented activities, this becomes a must-see destination for homebuyers searching in northern Virginia. If you would like more information regarding homes for sale in Winchester City, please contact us today and allow us to assist you.

Newest Winchester City Homes and Condos for Sale

1 W Hart St, Winchester image
1 W Hart St, Winchester $240,000

Excellent starter home OR investor property that is turn key MOVE-IN READY! Numerous extensive updates in 2021 including all new luxury vinyl flooring throughout, all new...

  • 3 Beds
  • 1 Baths
  • VAWI2002070 MLS
708 Frederick Ave, Winchester image
708 Frederick Ave, Winchester $249,000

PROFESSIONAL PHOTOS BEING TAKEN ON 7-6-22. Wonderful cape cod home located in a convenient location just off Berryville Avenue in the City of Winchester. This property h...

  • 2 Beds
  • 1 Baths
  • VAWI2001832 MLS
649 Hillman Drive, Winchester image
649 Hillman Drive, Winchester $525,000

This house Welcomes you Home with a front porch and a Craftsman style exterior. Enter the foyer and head to the heart of the home perfect for family gatherings and entert...

  • 4 Beds
  • 3 Baths
  • VAWI2002072 MLS
605 Lake Dr, Winchester image
605 Lake Dr, Winchester $459,000

Looks brand new! Original owner has taken meticulous care of this adorable home in popular Rolling Hills Estates. The front covered entry welcomes you home and into the...

  • 3 Beds
  • 3 Baths
  • VAWI2001976 MLS
1318 S Kent St, Winchester image
1318 S Kent St, Winchester $290,000

This beautifully updated almost new Townhome is one to see today! Two Primary suites, bonus space for those working from home or a daybed for a guest. Open updated kitche...

  • 2 Beds
  • 3 Baths
  • VAWI2002060 MLS
946 Wayne Dr, Winchester image
946 Wayne Dr, Winchester $645,000

What a great opportunity to own a beautiful customed home in Meadow Branch South. This home features 4,669 sqft. (3,889 sqft. finished) with 4 bedrooms, three full bathro...

  • 4 Beds
  • 4 Baths
  • VAWI2001966 MLS
11 E Leicester St, Winchester image
11 E Leicester St, Winchester $375,000

INVESTOR'S SPECIAL! This property has 2 units up and down. Each unit has 2 bed and 1 bath. The location is fabulous! Old Town Winchester on a quiet cross street betwe...

  • 3 Beds
  • 2 Baths
  • VAWI2002050 MLS
814 Winder Ct, Winchester image
814 Winder Ct, Winchester $469,900

This spacious home offers it all! One level living at it's best in a community of quality constructed homes having a great convenient location and being situated on a cul...

  • 3 Beds
  • 2 Baths
  • VAWI2002030 MLS
1012 Woodland Ave, Winchester image
1012 Woodland Ave, Winchester $309,000

3 Bedroom, 2 Bathroom Colonial split-level home that is minutes from Old Town Winchester and has multiple updates done in the past two years. Step inside past the split-f...

  • 3 Beds
  • 2 Baths
  • VAWI2002002 MLS
810 Amherst St, Winchester image
810 Amherst St, Winchester $429,000

This Dutch Colonial is perfectly located: blocks from Downtown Winchester, across the street from the Museum of the Shenandoah Valley (trails) and a short distance from t...

  • 4 Beds
  • 3 Baths
  • VAWI2001944 MLS
636 Watson Ave, Winchester image
636 Watson Ave, Winchester $275,000

Completely renovated and beautiful Cape Cod style home is move-in ready! House was rebuilt in 2019 with all new HVAC system, beautiful luxury plank flooring, fresh paint,...

  • 3 Beds
  • 2 Baths
  • VAWI2002012 MLS
439 N Braddock St, Winchester image
439 N Braddock St, Winchester $585,000

This magnificent solid built Brownstone is made for exquisite living and entertaining on a grand scale. Let's start with the beautiful walkway leading up to the enormous ...

  • 4 Beds
  • 2 Baths
  • VAWI2001928 MLS
312 Shenandoah Ave, Winchester image
312 Shenandoah Ave, Winchester $339,999 ▼

Charming home in the heart of Winchester! Large 3 bedroom 1.5 bath, with a spacious fully fenced back yard sits only minutes from shopping, restaurants and entertainment....

  • 3 Beds
  • 2 Baths
  • VAWI2001934 MLS
407 Jefferson St, Winchester image
407 Jefferson St, Winchester $399,900 ▼

Charming brick home in fantastic location adjacent to Handley High School and close to shopping and restaurants. This 3 bed, 1.5 bath home boasts gleaming hardwood floors...

  • 3 Beds
  • 2 Baths
  • VAWI2001990 MLS
651 Smithfield Ave, Winchester image
651 Smithfield Ave, Winchester $349,900

VERY WELL MAINTAINED SPLIT LEVEL HOME WITH 4 BEDROOMS AND 2 FULL BATHROOMS. FULLY FINISHED WALK OUT BASEMENT LEADING TO LARGE FENCED BACKYARD. PROPERTY HAS ONE CAR GARAGE...

  • 4 Beds
  • 2 Baths
  • VAWI2001964 MLS
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Purcellville, Virginia 20132

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