Winchester County VA Homes for Sale

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  $1,390,000

  • Studio
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an additional 2 bedrooms, full bathroom and could laundry room that

  

  Lori Bales

  Keller Williams Realty

  (540) 917-5619

  202 S Washington St, Winchester, VA 22601
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  /71

  $1,390,000

  • 7 Beds
  • 7 Baths
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! You have to see this $1M renovation by an architect out of NYC. Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an

  

  Lori Bales

  Keller Williams Realty

  (540) 660-3543

  202 S Washington St, Winchester, VA 22601
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  /63

  $564,000

  • 4 Beds
  • 3 Baths
  • 3,118 Sq Ft

  303 Walker St, Winchester, VA 22601

  Welcome to this beautifully maintained 4-bedroom, 3-bathroom home on a prime corner lot in Whittier Acres! Located on a quiet cul-de-sac and just a short stroll to Whittier Park and the Museum of the Shenandoah Valley, this home offers both convenience and charm. The meticulously landscaped yard sets the tone for the care found throughout the property. Inside, you'll find refinished hardwood

  

  Frank Armstrong, IV

  Colony Realty

  (540) 501-6918

  303 Walker St, Winchester, VA 22601
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  /18

  $399,000

  • 4 Beds
  • 1.5 Baths
  • 1,824 Sq Ft

  675 National Ave, Winchester, VA 22601

  Charming & Move-In Ready Home Near Shopping, I-81, Route 7 & Old Town Winchester! Welcome to this beautifully maintained home featuring freshly refinished hardwood floors and a bright, inviting layout. Enjoy a dedicated home office, a cozy breakfast nook, a sun-filled sunroom, and fresh paint throughout. The spacious, fenced-in backyard is perfect for relaxing or entertaining and includes a handy

  

  Frank Armstrong, IV

  Colony Realty

  (540) 696-5072

  675 National Ave, Winchester, VA 22601
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  /80

  $439,900

  • 4 Beds
  • 2 Baths
  • 1,564 Sq Ft

  2820 Baldwin St, Winchester, VA 22601

  CHARMING SPLIT FOYER HOME WITH 4 BEDROOMS AND 3 FULL BATHROOMS IN WINCHESTER!!!!!THIS WELL-MAINTAINED SPLIT FOYER HOME IN WINCHESTER OFFERS A FUNCTIONAL LAYOUT AND PLENTY OF SPACE. THE MAIN LEVEL FEATURES 3 BEDROOMS AND 2 FULL BATHROOMS, INCLUDING A SEPARATE LIVING ROOM AND DINING AREA, EACH OFFERING A CONFORTABLE SPACE FOR FAMILY TIME AND ENTERTAINING. THE KITCHEN IS READY FOR YOUR

  Carolina Mosquera Weichert, REALTORS

  2820 Baldwin St, Winchester, VA 22601
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  /50

  $784,900

  • 5 Beds
  • 4.5 Baths
  • 5,793 Sq Ft

  1013 Armistead St, Winchester, VA 22601

  Stunning Custom Colonial in the Coveted Meadow Branch NeighborhoodThis beautifully maintained colonial home offers the perfect combination of timeless elegance, modern comfort, and exceptional convenience. Boasting 5 bedrooms, 4.5 baths, and a first-floor office, this home features a thoughtfully designed open floor plan that blends sophistication with functionality. The custom gourmet

  AmyAnne Re Compass West Realty, LLC

  1013 Armistead St, Winchester, VA 22601
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  $445,000 Open Sat 1PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  803 Berryville Ave, Winchester, VA 22601

  **Welcome to Timeless Beauty—an exquisitely restored 1928 American Four Square, just minutes from Winchester’s Historic District and a commuter’s dream with easy access to Leesburg, Tysons Corner, and the DC Metro area.**This timeless beauty has been *renovated from top to bottom*, blending historic charm with modern luxury. Step through the generous foyer and take in the warmth of the

  Tanya Spotts Long & Foster Real Estate, Inc.

  803 Berryville Ave, Winchester, VA 22601
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  /57

  $566,500

  • 3 Beds
  • 2 Baths
  • 2,551 Sq Ft

  529 N Braddock St, Winchester, VA 22601

  Welcome home to this charming, light filled Dutch Colonial in the heart of downtown Winchester. With four livable levels, this three bedroom, 2 bath home has been lovingly updated and renovated over the years embracing the charm of a bygone era and offering modern conveniences. Updates include the addition of a dual zone heat pump system (2019) providing cooling and heating to all four levels of

  Dana Cloud Realty ONE Group Old Towne

  529 N Braddock St, Winchester, VA 22601
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  /57

  $589,900 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,125 Sq Ft

  220 Wolfe St, Winchester, VA 22601

  Classic craftsman style bungalow featuring a covered front porch supported by Tuscan columns located in the historic district. Super location between Washington and Stewart streets, convenient to everything in Old Town and within feet of the parade route! Other features include tons of storage in three floors of living space with three or four bedrooms, one of which can be used as a library or

  Kathrin Donovan Keller Williams Realty

  220 Wolfe St, Winchester, VA 22601
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  $550,000

  • 4 Beds
  • 4 Baths
  • 1,976 Sq Ft

  2008 Taylor Grace Ct, Winchester, VA 22601

  Wonderful location in Park Place subdivision near city park. Finished basement that includes a large recreation room and possible 5th bedroom with full bath. Bring the pets! Fenced back yard. Lots of upgrades to include, crown molding, chair rail and shadowboxes. Eat in kitchen opens to family room and large deck. Gas cooking with double oven and all stainless steel appliances. Shows

  Kent Mull Link Realty Services LLC

  2008 Taylor Grace Ct, Winchester, VA 22601
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  /27

  $439,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  127 Latane St, Winchester, VA 22601

  ?? LOCATION, LOCATION, LOCATION! Charming Brick Bungalow in Prime Downtown Winchester!?? This delightful three-bedroom, two-bath brick one level home is brimming with charm and ideally located within walking distance of downtown Winchester, Handley High School, the Patsy Cline House, 2-blocks from the parade route, and the historic district. With gorgeous hardwood floors, fresh modern

  Vanessa Couture ERA Oakcrest Realty, Inc.

  127 Latane St, Winchester, VA 22601
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  $525,000

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

  1921 Harvest Dr, Winchester, VA 22601

  Stunning Colonial in Meadow Branch South – Winchester, VA ** This home is in Move In Condition and can settle quickly!Welcome home to this meticulously maintained Colonial in the sought-after Meadow Branch South community! This 4-bedroom, 2.5-bath home is filled with thoughtful updates and timeless charm.Step inside to gleaming hardwood floors throughout the main level, where the

  Sue Smith Compass

  1921 Harvest Dr, Winchester, VA 22601
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  $550,000

  • 4 Beds
  • 3.5 Baths
  • 3,408 Sq Ft

  2717 Middle Rd, Winchester, VA 22601

  Welcome to 2717 Middle Road, a beautifully updated home that blends modern upgrades with timeless charm. Boasting 9-foot ceilings, oversized windows, and gleaming hardwood floors on the main level, this home offers a bright and spacious feel. The eat-in kitchen has been tastefully updated with new countertops and all-new appliances (2021), creating a stylish and functional space for

  Ben Barnes Jim Barb Realty Inc.

  2717 Middle Rd, Winchester, VA 22601
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  $839,900

  • 5 Beds
  • 4 Baths
  • 4,242 Sq Ft

  501 Princess Ct, Winchester, VA 22601

  It's all about spectacular mountain views! Built on one of the highest lots in Winchester by the area's premiere builder, Rhodes Brothers. Wake every morning to the fantastic views from the primary bedroom or enjoy your coffee while gazing at Great North Mountain. But this classic colonial home has a lot more to offer, including remodeled baths and kitchen, comfortable sunroom, five bedrooms, and

  John Schroth Colony Realty

  501 Princess Ct, Winchester, VA 22601
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  $446,000

  • 4 Beds
  • 2 Baths
  • 1,762 Sq Ft

  2320 Tower Ave, Winchester, VA 22601

  HUGE PRICE CUT!!!Don't drag your feet before this one disappear!!! Welcome to 2320 Tower Ave , Two Car garages ,4 legal bedrooms , 2 full bathrooms single family in quiet cul-de-sac is what you are waiting for is finally here to make it yours, the entire house just came out of renovations from freshly painted , Master Bathroom/Quartz, High Ceiling Family room, New Carpet, New

  Alex Adomako-Acheampong Samson Properties

  2320 Tower Ave, Winchester, VA 22601
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  $795,000

  • 7,650 Sq Ft

  230 W Boscawen St, Winchester, VA 22601

  Multifamily, Professional Office, Historical Residence, or a combination of any of these opportunities! Even potential bed and breakfast or events center! Located in Historical Old Town Winchester, Holly House offers three floors, totaling over 7650 +/- SF, PLUS a HUGE outdoor English courtyard, ideal for urban gardening, building expansion, additional parking or pool! Iconic Federal Style

  Gillian Greenfield Coldwell Banker Premier

  230 W Boscawen St, Winchester, VA 22601
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  $539,900

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft

  201 Parkway St, Winchester, VA 22601

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
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  /2

  $399,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft

  Bedford II, Winchester, VA 22601

  Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  DRB Homes

  Bedford II, Winchester, VA 22601
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  $475,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,309 Sq Ft

  319 Walker St, Winchester, VA 22601

  Coming Soon in Desirable Whittier Acres!This charming 4-bedroom, 2.5-bath Colonial is located just a few blocks from thriving downtown Winchester. Featuring a fantastic floorplan, a bright and inviting sunroom, and a beautifully landscaped yard, this home offers great curb appeal and endless potential. While it awaits your personal updates, its solid layout and prime location in a

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  319 Walker St, Winchester, VA 22601
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  /22

  $369,999

  • 3 Beds
  • 2 Baths
  • 1,060 Sq Ft

  601 Fairview Ave, Winchester, VA 22601

  Fully Renovated Gem in the Heart of Winchester! Welcome to 601 Fairview Ave, where modern upgrades meet timeless charm! This beautifully remodeled 3-bedroom, 2-bathroom rambler offers the perfect blend of comfort and convenience in one of Winchester’s most desirable locations.Step inside to discover a brand-new kitchen featuring stylish finishes, sleek countertops, and modern cabinetry—ready for

  Jorge Najarro Samson Properties

  601 Fairview Ave, Winchester, VA 22601
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  /2

  $252,372

  • 3 Beds
  • 1.5 Baths
  • 1,341 Sq Ft

  372 Gray Ave, Winchester, VA 22601

  Enjoy the charm of this all-brick traditional home with lovely hardwood floors throughout. Nice size primary bedroom, all bedrooms have closets, and several recent updates in 2024 make this home absolutely move-in ready! You can decide if you prefer relaxing on your front or back porch or enjoying coffee on your rear balcony. There is also a back patio area if you want to grill your favorite

  Pamela Foltz Realty ONE Group Old Towne

  372 Gray Ave, Winchester, VA 22601
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  $625,000

  • 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 convenience,

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
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  /12

  $90,000

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft

  222 Liberty Ave, Winchester, VA 22601

  **OFFER DEADLINE MONDAY APRIL 21ST AT 2PM**Investor, builder, or renovation enthusiast—this is the opportunity you’ve been waiting for!This 2-bedroom, 1-bath home is a true fixer-upper with serious potential. Whether you’re looking to take on a full gut renovation or tear it down and start from scratch, this property is a blank canvas ready for your vision. With 882 square feet of

  Chris Craddock EXP Realty, LLC

  222 Liberty Ave, Winchester, VA 22601
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  $379,000

  • 3 Beds
  • 1.5 Baths
  • 1,178 Sq Ft

  107 E Monmouth St, Winchester, VA 22601

  Charming Historic Home in Downtown Winchester – Move-In Ready!If you love timeless craftsmanship—think original wood floors, custom built-ins, and vintage doors—but still want the ease of modern living, this beautifully updated downtown Winchester home is calling your name!From the moment you step onto the inviting covered porch and through the front door, you’ll feel right at

  Jeanne Mezzatesta Colony Realty

  107 E Monmouth St, Winchester, VA 22601
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  $299,900

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  2301 Tower Ave, Winchester, VA 22601

  Welcome to this charming and cozy budget friendly home. With 3 bedrooms on the main level and a full basement below with tons of room for future expansion that walks out to a large off-street parking area this home is bursting with potential! The big ticket items are already there with newer high-end appliances, heat pump and central air, 200 amp service, etc this home is ready for your cosmetic

  Clint Pierpoint NextHome Realty Select

  2301 Tower Ave, Winchester, VA 22601
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  /25

  $369,000

  • 3 Beds
  • 1.5 Baths
  • 1,457 Sq Ft

  200 Shawnee Ave, Winchester, VA 22601

  Charming Cape Cod in the Heart of Downtown Winchester! This beautifully maintained 3-bedroom home seamlessly blends timeless character with luxurious modern updates. Hardwood floors grace the main level, complementing a fully renovated kitchen featuring high-end finishes and ample table space. The bathrooms have been thoughtfully remodeled with upscale materials, new flooring and elegant touches

  Holly Wilson Samson Properties

  200 Shawnee Ave, Winchester, VA 22601
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  $429,000

  • 4 Beds
  • 2 Baths
  • 2,134 Sq Ft

  320 S Cameron St, Winchester, VA 22601

  Historic Charm? Check!Modern Amenities? Check!Location? Check!Welcome to 320 S. Cameron Street! Built in 1773, this property will transport you back in time as soon as you arrive! The outside is host to 3 shops/outbuildings; some with power, an English garden, and original horse hitching posts! From the side porch, you will enter a newly renovated kitchen featuring stainless steel appliances and

  Matt Leiva Keller Williams Realty

  320 S Cameron St, Winchester, VA 22601
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  $399,000

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft

  1005 Pennsylvania Ave, Winchester, VA 22601

  This charming classic brick ranch in Winchester, VA, features 3 bedrooms and 2 full bathrooms, with easy access to downtown Winchester. As you approach, the large covered front porch sets a welcoming tone. The basement, with a separate entrance and extra bedrooms, is large and very clean. It has a laundry area and one full bathroom, and the family room can be converted into a bedroom. Recent

  Nathalie Acosta Spring Hill Real Estate, LLC.

  1005 Pennsylvania Ave, Winchester, VA 22601
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  /24

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  16 W Clifford St, Winchester, VA 22601

  Wooden construction, Alley side home ready for construction. Boarders Downton Winchester, blocks form Historic Old town, Walking Mall and restaurant Alley. 5 minutes drive to Shenandoah University. Winchester has been named fastest growing place in all of VA. Best place to retire by FORBS magazine. 15 hour outside of Washington DC excellent location for rental. Approved plans for

  Carlos Beamon Samson Properties

  16 W Clifford St, Winchester, VA 22601
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  /34

  $309,000

  • 3 Beds
  • 2 Baths
  • 1,313 Sq Ft

  320 Highland Ave, Winchester, VA 22601

  Welcome to this centrally located home in the heart of Winchester. With easy access to I-81, this home is in a great commuter's location. Just a quick walk or drive away are the charming shops and restaurants of Historic Old Town Winchester. The main level features hardwood floors, a living room with wood-burning brick fireplace and a formal dining room, featuring a charming a built in China

  Heloisa Amar Samson Properties

  320 Highland Ave, Winchester, VA 22601
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  /2

  $325,000

  • 8 Beds
  • 5 Baths
  • 12,127 Sq Ft

  910 Franklin St, Winchester, VA 22601

  RARE UNIQUE OPPORTUNITY KNOCKS!Warehouse and all 4 units cleaned, and junk removed - Ready for new investor.Do not miss this rare opportunity to own this rare, unique mixed-use property in Winchester. Work with the city of Winchester and turn this into your dream project!Excellent rate of return with existing units. Two residential apartments upstairs and two

  Pakeeza Akhtar The KOR Group, Inc.

  910 Franklin St, Winchester, VA 22601
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  /26

  $295,000

  • 3 Beds
  • 1 Bath
  • 963 Sq Ft

  701 Watson Ave, Winchester, VA 22601

  Immaculate Renovation of 3 Bedroom and 1 Bath Single Family Home*New Kitchen Includes: New White Cabinets, New Quartz Countertop, New Stainless Steel Appliances, New Ceramic Tile Flooring*Refinished Hardwood Floors*New Windows*New HVAC*All New Bathroom*Newer Roof, Gutters and Downspouts*New Side Porch and Decking*New Exterior Doors*New Recessed Lights*New Washer and Dryer*Full Unfinished

  Gary Green Samson Properties

  701 Watson Ave, Winchester, VA 22601
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  /27

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft

  1309 Commerce St, Winchester, VA 22601

  This charming all-brick ranch is making its first appearance on the market since the 1970s! It's a fantastic opportunity for first-time homebuyers or investors looking to add their personal touch. The home features three bedrooms, with hardwood floors, carpet, and a full bath on the main level. The cozy family room and kitchen complete the main floor, with hardwood flooring said to be beneath

  Jeff Boppe Long & Foster Real Estate, Inc.

  1309 Commerce St, Winchester, VA 22601
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  /56

  $324,900

  • 3 Beds
  • 2.5 Baths
  • 1,839 Sq Ft

  304 Virginia Ave, Winchester, VA 22601

  Experience everything Winchester, VA has to offer from your quaint renovated home with full front porch, private deck, original flooring upon entry, fully improved kitchen, and so much more. Home is larger than it appears and offers a wonderful playroom/music room on main level, separate dining room, family room, large kitchen and three larger bedrooms upstairs. The primary bathroom took the

  Adam Shively Samson Properties

  304 Virginia Ave, Winchester, VA 22601
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  $329,900

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  629 National Ave, Winchester, VA 22601

  Welcome to this newly updated home in a prime Winchester City location, where modern style meets everyday convenience. Featuring an open floor plan on the main level, this 2-bedroom, 1-bath home offers spacious bedrooms and a sleek, modern bathroom with bright finishes. The kitchen is designed for both style and function, complete with granite countertops, soft-close cabinetry, and stunning

  Elizabeth Carroll ERA Oakcrest Realty, Inc.

  629 National Ave, Winchester, VA 22601
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  $899,900

  • 3 Beds
  • 3.5 Baths
  • 4,987 Sq Ft

  707 Kennedy Dr, Winchester, VA 22601

  Custom built home by Owner. This spacious home will fill all of your entertaining needs both inside and outside, Open Kitchen and family room, built in wet bar, sunroom and a Florida room to take you outside to a beautiful inground pool.. Covered area for your pool equipment and entertain at your tiki bar with a full bath. Want to entertain inside , you can do it in the formal dinning

  Diane Walter Crum Realty, Inc.

  707 Kennedy Dr, Winchester, VA 22601
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  $2,150,000

  • Studio
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  In town location for this completely remodeled multi unit property. This property contains 4 homes and 2 apartments that have been completely refinished. The main home is currently lived in by the owner and is attached to a indoor swimming pool. The other 3 homes and 2 apartments are leased and are bringing over$10,500 monthly. If you choose rent the main house income would be much higher. .

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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  /67

  $899,990

  • 5 Beds
  • 4.5 Baths
  • 6,122 Sq Ft

  939 Buckner Dr, Winchester, VA 22601

  Listed Well Below Its True Worth! This fully brick home was built in 2000 in Meadow Branch and has been through extensive renovations and updates in 2023 & 2024. The main level bedroom includes a generous, newly updated ensuite with an oversized marble tiled shower & dual vanities. The ensuite also features a grand walk-in closet crafted by ClosetsByDesign. The heart of the home, the kitchen, has

  Kiran K. Morzaria Parekh Redfin Corporation

  939 Buckner Dr, Winchester, VA 22601
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  /42

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  127 S Euclid Ave, Winchester, VA 22601

  REDUCE PRICE!!!!! BEATIFULL HOME!!!

  Carolina Mosquera Weichert, REALTORS

  127 S Euclid Ave, Winchester, VA 22601
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  /56

  $2,150,000

  • 4 Beds
  • 2.5 Baths
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  Opportunity meets elegance in this fully remodeled multi-unit gem, perfectly situated in a prime in-town location. This unique property features four beautifully refinished homes and two modern apartments, offering both luxury and income potential in one impressive package.The main residence—currently owner-occupied—is a standout, seamlessly connected to a private indoor swimming pool,

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601

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