Winchester County VA Homes for Sale

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  $299,900

  • 3 Beds
  • 1 Bath
  • 1,204 Sq Ft

  625 Watson Ave, Winchester, VA 22601

  Nestled in Orchard Terrace, this beautifully updated Colonial home is ideally located within Winchester city limits, just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen features new cabinets, granite countertops, stainless steel appliances, a new sink and faucet, and vinyl plank flooring. The bathroom includes a new vanity, vanity

  Jennifer Sacco RE/MAX Roots

  625 Watson Ave, Winchester, VA 22601
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  /35

  $419,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,939 Sq Ft

  1817 Harvest Dr, Winchester, VA 22601

  1817 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for February move-in. Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel appliances. The

  D.R. Horton Builder

  1817 Harvest Dr, Winchester, VA 22601
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  /3

  $150,000

  • 3 Beds
  • 1 Bath
  • 882 Sq Ft

  222 Liberty Ave, Winchester, VA 22601

  Calling all investors, contractors, and savvy home buyers! Seize this incredible opportunity to own a 3-bedroom, 1-bath home in an up-and-coming Winchester neighborhood. This property is the definition of "sweat equity," and the heavy lifting has already been started for you. Property has had a recently survey and property lines are marked. The current owner has completed the two hardest parts of

  Kandi McKenzie Realty ONE Group Old Towne

  222 Liberty Ave, Winchester, VA 22601
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  /7

  $499,000

  • Land
  • 5.02 Acres
  • $99,402 per Acre

  LOT 136 Senseny Rd, Winchester, VA 22602

  Unlock the potential of this prime 5-acre lot situated at the intersection of Senseny Road and Oak Ridge Lane. Zoned RP, this expansive parcel represents a rare development opportunity on Winchester’s highly desirable east side. The property provides a versatile and buildable canvas for a variety of residential projects. Its strategic location offers the perfect balance of high visibility for

  Dan Whitacre Colony Realty

  LOT 136 Senseny Rd, Winchester, VA 22602
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  /68

  $759,000

  • 6 Beds
  • 3 Baths
  • 4,260 Sq Ft

  705 Treys Dr, Winchester, VA 22601

  Over 4,300 square feet of above-grade living space with a flexible six-bedroom layout, located near the Green Circle Trail, Winchester Medical Center, and downtown Winchester. Welcome to Williamsburg Heights — a well-established neighborhood of attractive homes with no HOA. A welcoming wraparound porch spans the front and side of the home, with a door leading directly into the dining room—perfect

  Natalie Langford ERA Oakcrest Realty, Inc.

  705 Treys Dr, Winchester, VA 22601
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  /56

  $439,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  743 Berryville Ave, Winchester, VA 22601

  Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot.The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to

  Sineenat Sirimas Pearson Smith Realty, LLC

  743 Berryville Ave, Winchester, VA 22601
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  /28

  $429,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
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  /46

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,837 Sq Ft

  1317 Caroline St, Winchester, VA 22601

  Welcome to 1317 Caroline Street, a well-appointed brick rancher in a fantastic Winchester location that perfectly balances professional convenience with residential comfort. Situated just minutes from Winchester Medical Center and major commuter routes, this home offers an effortless transition from a busy day to a relaxing evening. This sense of ease begins the moment you step inside the main

  Dan Whitacre Colony Realty

  1317 Caroline St, Winchester, VA 22601
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  /30

  $409,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  221 Monteith Dr, Winchester, VA 22601

  END OF ROW Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level end unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended

  DRB Homes Builder

  221 Monteith Dr, Winchester, VA 22601
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  /20

  $384,990 Open Sat 12PM - 4PM

  • 3 Beds
  • 4 Baths
  • 1,910 Sq Ft

  105 Boone Ct, Winchester, VA 22602

  Move in ready at Rossum Crossing townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two full and two half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a pantry closet, and a breakfast nook.

  Dorelba Estrada New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
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  /2

  $399,900 Open House 3/21

  • 2 Beds
  • 2 Baths
  • 1,405 Sq Ft

  1851 Melvor Ln, Winchester, VA 22601

  Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to

  RoxAnn Grimes RE/MAX Roots

  1851 Melvor Ln, Winchester, VA 22601
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  /17

  $215,000

  • Land
  • 0.36 Acre
  • $597,222 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  /32

  $399,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  3138 Eton Place, Winchester, VA 22601

  Beautiful, just like brand new, 3 bedroom 2.5 bath end unit townhome located in The Lofts at Creekside! Walking distance to local restaurants and shopping here in Creekside. Home features large kitchen island, stainless steel appliances, and luxury vinyl plank flooring, private balcony, surrounded by open floor plan which provides for great entertainment. Nice upgrades all throughout the house!

  Christopher Hild Realty FC, LLC

  3138 Eton Place, Winchester, VA 22601
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  /4

  $360,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  101 Molden Dr, Winchester, VA 22601

  This 1963 brick ranch is conveniently located off Pleasant Valley Road in Eastview Subdivision and has been the home to one family. Beautiful hardwood floors throughout the main level, and two fireplaces, one on the main level and one in the finished recreation room on the lower level. Most of the windows throughout the home have also been replaced. Oversized two car garage. Roof was replaced in

  Elizabeth Page Boxwell MarketPlace REALTY

  101 Molden Dr, Winchester, VA 22601
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  /3

  $95,000 Coming Soon

  • Land
  • 0.2 Acre
  • $475,000 per Acre

  816 Allen Dr, Winchester, VA 22601

  Rare opportunity to buy a level building lot conveniently located off Pleasant Valley Road in Eastview Subdivision. This lot is being sold with a 24x24 two bay garage. The garage presently has electric service from the adjoining property, which is also being sold by the same owners. If this lot w/ garage are purchased separately, new owner must obtain their own electric service. Adjoining

  Elizabeth Page Boxwell MarketPlace REALTY

  816 Allen Dr, Winchester, VA 22601
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  /2

  $499,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,068 Sq Ft

  2510 Windwood Dr, Winchester, VA 22601

  Professional photos coming. Welcome home to this spacious four bedroom, two and a half bath home in the Westridge subdivision. The traditional main level floor plan offers the perfect separation of spaces which include a formal dining room or potential home office/den, a kitchen that opens into a living area perfect for a casual breakfast table and a cozy sofa in front of the fireplace and a

  Dana Cloud Realty ONE Group Old Towne

  2510 Windwood Dr, Winchester, VA 22601
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  /3

  $319,900 Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,130 Sq Ft

  126 S Euclid Ave, Winchester, VA 22601

  This 3-bedroom, 1 full bath home is ready for you to move right in! Entire inside has been freshly painted. As you enter, you'll see the spacious living room with LVP flooring. Kitchen with new LVP flooring, new stainless-steel stove, new stainless-steel hood vent, new stainless-steel refrigerator and an eating area. Beautiful full bath with tile shower. 3 great sized bedrooms with vinyl

  Matt Kilmer Samson Properties

  126 S Euclid Ave, Winchester, VA 22601
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  /2

  $250,000 Coming Soon

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  523 Monticello St, Winchester, VA 22601

  Sold "As-IS" Nice investment or starter property. Needs a little updating. Hardwoods throughout upstairs and living room downstairs. This price includes 525 Monticello lot. Tax ID #330-02-19. If any questions call listing agent. Agent related to seller.

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 305-3611

  523 Monticello St, Winchester, VA 22601
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  /43

  $429,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft

  1332 Ramseur Ln, Winchester, VA 22601

  Welcome home to this rare find in the desirable Mews of Meadow Branch—an exceptional all-brick exterior condo offering 3 bedrooms and 2 full baths. This well-maintained home is in excellent condition and features rich hardwood floors flowing throughout, creating a warm and inviting atmosphere. The spacious primary bedroom includes a cozy fireplace, perfect for relaxing evenings at home. The

  James King RE/MAX Roots

  1332 Ramseur Ln, Winchester, VA 22601
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  /34

  $399,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,920 Sq Ft

  1821 Harvest Dr, Winchester, VA 22601

  1821 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA – ready to move in! Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, soft-close grey cabinets & drawers, and

  D.R. Horton Builder

  1821 Harvest Dr, Winchester, VA 22601
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  /34

  $419,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,920 Sq Ft

  1813 Harvest Dr, Winchester, VA 22601

  1813 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA – ready to move in! Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, soft-close grey cabinets & drawers, and

  D.R. Horton Builder

  1813 Harvest Dr, Winchester, VA 22601
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  /34

  $337,000

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  19 W Germain St, Winchester, VA 22601

  Life in Historic Winchester just got easier with this modern construction. Built in 2004, this Charming 3 Bedroom, 1.5 Bath home is the best of all worlds. This home has been completely & professionally remodeled in 2025 and the quality of construction shows. Fresh and bright you will find that practically everything is new. Enter to find newly finished gleaming hardwood floors (2025), crisp new

  Angela Duncan MarketPlace REALTY

  19 W Germain St, Winchester, VA 22601
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  /62

  $735,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 3,482 Sq Ft

  1419 Ramseur Ln, Winchester, VA 22601

  Spacious 4 bed / 3 bath brick-front rancher located in the City of Winchester, just minutes from Winchester Medical Center, the library, shopping, dining, and historic downtown. Enjoy community amenities at Early’s Green at Meadowbranch, including an outdoor pool and tennis courts. This home offers true one-level living with the added bonus of a fully finished basement featuring a custom-built

  Sheila Pack RE/MAX Roots

  1419 Ramseur Ln, Winchester, VA 22601
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  /45

  $519,900

  • 2 Beds
  • 2 Baths
  • 1,850 Sq Ft

  411 302 N Loudoun St, Winchester, VA 22601

  Just 3 blocks to the Winchester Walking Mall, Unit 302 at The Fort puts downtown coffee shops, cuisine, mom & pop shops, museums, art, & the grand library right at your fingertips—then brings you home to a penthouse retreat with the best views in the building of both sunrise and sunset. Kiss yard work bye bye & say hello to single level living with an elevator. Where off street parking is

  Sarah Abderrazzaq Realty ONE Group Old Towne

  411 302 N Loudoun St, Winchester, VA 22601
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  /40

  $640,000 Open Sat 12PM - 2PM

  • 6 Beds
  • 3.5 Baths
  • 3,192 Sq Ft

  162 Omps Dr, Winchester, VA 22601

  This exceptional residence is nestled in a popular neighborhood in Winchester, just moments from Winchester Medical Center. With almost 4,000 square feet of refined living space, this 6-bedroom, 3.5-bath home delivers the scale, comfort, and location today’s discerning buyer expects.Designed for both elegant entertaining and everyday ease, the home features expansive living areas filled with

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-1014

  162 Omps Dr, Winchester, VA 22601
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  /2

  $459,000 Coming Soon

  • 6 Beds
  • 3 Baths
  • 1,552 Sq Ft

  2250 Roosevelt Blvd, Winchester, VA 22601

  Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

  Heloisa Amar Samson Properties

  2250 Roosevelt Blvd, Winchester, VA 22601
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  /58

  $549,900

  • 4 Beds
  • 2.5 Baths
  • 2,234 Sq Ft

  1917 Harvest Dr, Winchester, VA 22601

  Beautiful Colonial set in a quiet neighborhood with convenient access to town and I-81. The main level features gleaming hardwood floors and classic oak plantation shutters, creating a warm and inviting feel throughout. Enjoy a formal living room with built-in shelving and a formal dining room accented by a chair rail, perfect for gatherings and entertaining. The kitchen offers granite

  

  Brock Harris

  Samson Properties

  (540) 712-8133

  1917 Harvest Dr, Winchester, VA 22601
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  /22

  $949,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,546 Sq Ft

  0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602

  TO BE BUILT: Fauver and Browning Homes proudly presents The Tremont House—a masterfully designed modern residence that blurs the line between architecture and nature. Thoughtfully crafted to harmonize with its surroundings, this home offers a calm, refined living experience. Tucked at the end of a private cul-de-sac in desirable Fairway Estates, overlooking Winchester Country Club, the design

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 698-4119

  0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602
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  /45

  $500,000 Open Sun 12PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,524 Sq Ft

  2643 Middle Rd, Winchester, VA 22601

  Location Location Location! NO HOA!!! Hardwood floors on the main level. Formal living and dining room leads to the Family room with stone fireplace, breakfast nook and kitchen. Step out on to the deck to enjoy the views. Large fenced level backyard. Large Primary suite with sitting room and luxury bath. Good sized bedrooms, one with an attached bath. Lower level leads to a patio and backyard.

  Lorraine Arora Berkshire Hathaway HomeServices PenFed Realty

  2643 Middle Rd, Winchester, VA 22601
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  /65

  $479,900

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  620 Crystal Ct, Winchester, VA 22601

  Rare Cul-de-Sac Gem in the Heart of Winchester Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready for you to call home. Main Level Elegance & Modern UpgradesFrom the moment you step onto the

  VAIBHAV AGARWAL Realty FC, LLC

  620 Crystal Ct, Winchester, VA 22601
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  /47

  $279,000

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  106 W Southwerk St, Winchester, VA 22601

  This charming 3-bedroom, 1.5-bath Colonial is perfectly located just minutes from Old Town Winchester and steps from Handley High School, giving you easy access to local restaurants, shops, and community events. Enjoy slow mornings on the covered front porch with your coffee, or gather with friends and family on the spacious back deck. Inside, you’ll find warm, comfortable living spaces filled

  Laura White ERA Oakcrest Realty, Inc.

  106 W Southwerk St, Winchester, VA 22601
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  /31

  $454,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  1025 S Loudoun St, Winchester, VA 22601

  Prepare to be wowed by this stunning renovation in downtown Winchester! This charming Colonial has been fully remodeled and is ready for new owners. No detail was spared—original features were thoughtfully preserved to maintain the home’s historic charm, while modern conveniences were added throughout for everyday living. The original hardwood floors were refinished and run throughout the house,

  Heloisa Amar Samson Properties

  1025 S Loudoun St, Winchester, VA 22601
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  /7

  $1,100,000

  • Land
  • 2.3 Acres
  • $478,261 per Acre

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

  2.3 Acre Outparcel on Pleasant Valley Road for Sale Neighbors include Walmart, Ross, Target, Panera Bread, Olive Garden, Petco, and the list goes on! Zoned CM1, ideal for auto sales, offices, retail, and flex development. All utilities to site. Outstanding proximity to massive commercial and multifamily growth. VA's fastest growing City in it's fastest growing commercial district. Almost 500'

  Gillian Greenfield Coldwell Banker Premier

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601
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  /69

  $605,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

  Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
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  /21

  $389,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  218 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: 3/14 Saturday - 3/15 Sunday 12pm - 3pm End of Row Townhome With All Three Finished Levels! This three level end of row townhome features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height. The first level

  DRB Homes Builder

  218 Monteith Dr, Winchester, VA 22601
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  /35

  $285,000

  • 2 Beds
  • 2 Baths
  • 780 Sq Ft

  2519 Hockman Ave, Winchester, VA 22601

  Nestled in the charming Hillcrest neighborhood, this delightful Craftsman-style home, built in 1950 and set to shine with major renovations in 2024, offers a perfect blend of classic character and modern convenience. With two spacious bedrooms and two full bathrooms, this residence is designed for comfort and functionality. The heart of the home features a well-appointed kitchen equipped with

  Channing Sherfey Hoffman Realty

  2519 Hockman Ave, Winchester, VA 22601
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  /62

  $884,000

  • 5 Beds
  • 4.5 Baths
  • 4,438 Sq Ft

  769 Seldon Dr, Winchester, VA 22601

  Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along

  Amanda Slate Keller Williams Realty

  769 Seldon Dr, Winchester, VA 22601
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  /12

  $290,000

  • 2 Beds
  • 1 Bath
  • 817 Sq Ft

  580 York Ave, Winchester, VA 22601

  Charming and completely updated! This beautiful home features a brand-new kitchen with new appliances, an updated bathroom, newly installed HVAC system, and a new water heater. Truly move-in ready and waiting for its next owner!

  Yoselin Mejia The Vasquez Group LLC

  580 York Ave, Winchester, VA 22601
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  /45

  $449,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  25 W Southwerk St, Winchester, VA 22601

  Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers the perfect balance of neighborhood tranquility and

  Dan Whitacre Colony Realty

  25 W Southwerk St, Winchester, VA 22601
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  /73

  $650,000

  • 4 Beds
  • 3.5 Baths
  • 3,474 Sq Ft

  132 Amherst St, Winchester, VA 22601

  Charming Victorian home in the Heart of Historic downtown Winchester and located just off of the Apple Blossom Parade route with a fabulous large yard, great for entertaining and gardening. Loaded with the charm of the era, plus many updates for comfort and convenience. The foyer, front staircase , living, dining , family and main level bedrooms have beautiful wood flooring reminiscent of years

  Darcy Amburn Colony Realty

  132 Amherst St, Winchester, VA 22601

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