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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

812 Appleseed Ct, Winchester image
812 Appleseed Ct, Winchester $359,000

Nestled on a quiet cul-de-sac surrounded by mature trees in the highly desirable Orchard Hills Subdivision with no HOA fees or restrictions, this traditional all-brick ho...

  • 3 Beds
  • 2 Baths
  • VAWI2011584 MLS
1847 Melvor Ln, Winchester image
1847 Melvor Ln, Winchester $355,000

Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, funct...

  • 2 Beds
  • 2 Baths
  • VAWI2011574 MLS
322 E Piccadilly, Winchester image
322 E Piccadilly, Winchester $409,000

Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless ch...

  • 4 Beds
  • 1 Baths
  • VAWI2011520 MLS
1957 Cidermill Ln, Winchester image
1957 Cidermill Ln, Winchester $374,900

"Come On Down To Cidermill" Beautiful 3 bedroom, 2 1/2 bath duplex style townhome at end of street! All 3 bedrooms on upper level. Spacious family room, large eat in kitc...

  • 3 Beds
  • 3 Baths
  • VAWI2011570 MLS
2700 Loyalty Ct, Winchester image
2700 Loyalty Ct, Winchester $699,000

Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted l...

  • 7 Beds
  • 5 Baths
  • VAWI2011542 MLS
214 Molden Dr, Winchester image
214 Molden Dr, Winchester $230,000

Investor opportunity in Winchester! This 2-bedroom, 1-bath home offers 1,112 finished square feet above grade, plus a full unfinished basement with additional space for s...

  • 2 Beds
  • 1 Baths
  • VAWI2011526 MLS
1048 Woodland Ave, Winchester image
1048 Woodland Ave, Winchester $350,000

Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless a...

  • 3 Beds
  • 2 Baths
  • VAWI2010942 MLS
1412 S Loudoun St, Winchester image
1412 S Loudoun St, Winchester $429,000

Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths...

  • 3 Beds
  • 2 Baths
  • VAWI2011442 MLS
2519 Hockman Ave, Winchester image
2519 Hockman Ave, Winchester $308,000

This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detache...

  • 2 Beds
  • 2 Baths
  • VAWI2011408 MLS
1414 S Braddock St, Winchester image
1414 S Braddock St, Winchester $379,900

This charming Cape Cod home in Winchester City, built in 1950 and beautifully renovated in 2026, offers a perfect blend of classic character and modern convenience. With ...

  • 2 Beds
  • 2 Baths
  • VAWI2011510 MLS
1125 Conway St, Winchester image
1125 Conway St, Winchester $250,000

Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwoo...

  • 2 Beds
  • 1 Baths
  • VAWI2011448 MLS
229 Monteith Dr, Winchester image
229 Monteith Dr, Winchester $369,990

The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or f...

  • 3 Beds
  • 4 Baths
  • VAWI2011454 MLS
237 Monteith Dr, Winchester image
237 Monteith Dr, Winchester $359,990

The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added...

  • 3 Beds
  • 4 Baths
  • VAWI2011458 MLS
700 Green St, Winchester image
700 Green St, Winchester $359,000

You've been dreaming of main-level living, and this is IT! Check all your boxes: ✅ 3 bedrooms ✅ 2 full bathrooms ✅ Open-concept family room ✅ Beautifully updated kitchen...

  • 3 Beds
  • 2 Baths
  • VAWI2011450 MLS
63 Riflemen Ln, Winchester image
63 Riflemen Ln, Winchester $394,900 ▼

Nestled in the charming Morganside community, this delightful split-level home offers a perfect blend of comfort and functionality. Built in 1997, this well-maintained re...

  • 3 Beds
  • 2 Baths
  • VAWI2011452 MLS
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