Winchester County VA Homes for Sale

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  $1,899,000

  • 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. . Update, main house is now rented and income is over $15,000 per month. This property is also improved with large block garage and a separate 4 car garage with over 18' ceilings. Perfect for the automotive enthusiast or you can continue to

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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  /21

  $384,990 Open Thu 12PM - 3PM

  • 3 Beds
  • 4 Baths
  • 1,989 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 and a 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. This

  Holly Horne Poole New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
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  /47

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  712 Frederick Ave, Winchester, VA 22601

  Charming Cape Cod in a highly desirable Winchester location! This sweet home offers a rare bonus—plenty of off-street parking from the alley plus a one-car garage (24x20), making everyday living (and entertaining) a breeze. INTERIOR: You’ll find a main-level primary bedroom along with cozy living spaces including a separate dining area, inviting living room, and a warm, comfortable den. Upstairs

  Jennifer Avery Crum Realty, Inc.

  712 Frederick Ave, Winchester, VA 22601
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  /47

  $479,900

  • 4 Beds
  • 2.5 Baths
  • 1,960 Sq Ft

  418 Circle Dr, Winchester, VA 22601

  New construction without the wait! This two-year-young home is like new and ready for its next owners. Enjoy a spacious open floor plan featuring LVP flooring throughout the main level, a modern kitchen with stainless steel appliances and a large center island. The main level also offers a private home office and a convenient half bath. Upstairs, retreat to a spacious primary suite complete with

  Heloisa Amar Samson Properties

  418 Circle Dr, Winchester, VA 22601
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  /20

  $455,000

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

  2250 Roosevelt Blvd, Winchester, VA 22601

  Sellers are highly motivated and ready to make a deal!Beautifully Renovated Single-Family Home with a little Pool, Workshop, and Detached GaragesWelcome to this stunning fully renovated 4-bedroom, 3-bathroom single-family home that perfectly blends comfort, style, and functionality. Step inside to find an open-concept layout filled with natural light, ideal for both everyday living and

  Silvana Rojas Spring Hill Real Estate, LLC.

  2250 Roosevelt Blvd, Winchester, VA 22601
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  /3

  $2,300,000

  • Land
  • 3.51 Acres
  • $655,271 per Acre

  1721 Amherst St, Winchester, VA 22601

  3.51 AC of premier commercial land. Directly across the street from the main hospital campus on one of Winchester's main commercial corridors. Ideal for banks, medical offices, retail or restaurants.

  Marie DiLorenzo Oakcrest Commercial LLC.

  1721 Amherst St, Winchester, VA 22601
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  /20

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  Don't miss taking a LOOK at this property with the new low price of $319K. One Way street = quiet Gorgeous Rehab - you have to see it! Secure Parking off the alley Efficient HVAC mini splits installed Washer and Dryer included

  Teri Domanski Corcoran McEnearney

  553 Highland Ave, Winchester, VA 22601
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  $449,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  1819 Reese Ct, Winchester, VA 22601

  1819 Reese Court is a move-in ready 3-level townhome with full brick front in Winchester, VA. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP flooring. The kitchen is equipped with beautiful quartz countertops, sasparilla cabinets, and stainless-steel appliances. The upper

  D.R. Horton Builder

  1819 Reese Ct, Winchester, VA 22601
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  /58

  $985,000

  • 7 Beds
  • 5.5 Baths
  • 6,540 Sq Ft

  1020 Breckinridge Ln, Winchester, VA 22601

  Approximately 6,500 finished square feet of living space! A place to grow, gather, and stay awhile! A brick-paved, rocking chair-worthy, front porch sets the tone, and the charming side porch with composite decking is both stylish and maintenance-free. This spacious 6+ bedroom/5.5 bath residence features a main-level bedroom and full bath—ideal for an in-law suite. Just off the kitchen, the

  Sheila Pack RE/MAX Roots

  1020 Breckinridge Ln, Winchester, VA 22601
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  /36

  $438,140 New Construction

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

  1805 Harvest Dr, Winchester, VA 22601

  1805 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

  1805 Harvest Dr, Winchester, VA 22601
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  /20

  $439,900

  • Studio
  • 2,376 Sq Ft

  510 N Loudoun St, Winchester, VA 22601

  All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD/1BA with unfinished attic, main floor is 1BR/1BA (Both have rear balcony) and basement unit has access to storage area and includes1BD/1BA. All units have washer/dryer (Basement unit washer/dryer belongs to tenant). Owner/Agent and home inspection report available upon request.

  Dave Spence RE/MAX Roots

  510 N Loudoun St, Winchester, VA 22601
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  $469,900

  • 3 Beds
  • 4 Baths
  • 3,359 Sq Ft

  227 Miller St, Winchester, VA 22601

  BE SURE TO WATCH THE VIDEO TOUR! Welcome to 227 Miller Street — a home that instantly feels inviting. Recent improvements include new flooring in both upstairs and downstairs bathrooms (2025), new toilets in all bathrooms (2024), refreshed hardwood floors (2025), a professionally cleaned chimney (2025). The back deck was replaced in 2024, and the home offers multiple outdoor spaces, including a

  Leah Marabella Realty ONE Group Old Towne

  227 Miller St, Winchester, VA 22601
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  /14

  $285,000 Coming Soon

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  2519 Hockman Ave, Winchester, VA 22601

  Channing Sherfey Hoffman Realty

  2519 Hockman Ave, Winchester, VA 22601
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  /40

  $358,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft

  323 Russelcroft Rd, Winchester, VA 22601

  Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living space. Beautiful cared for by the homeowners. 3 bedrooms 2 full baths detached home.Beautiful Detached home with 3 bedrooms and 2 full baths + bonus room on the basement isfull finished with a family room. Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living

  Alexandra Brown Spring Hill Real Estate, LLC.

  323 Russelcroft Rd, Winchester, VA 22601
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  /23

  $279,000

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft

  208 Shenandoah Ave, Winchester, VA 22601

  Welcome home to 208 Shenandoah Ave in Winchester, VA! This updated ranch home offers the coveted simplicity of easy, one-level living and is perfectly situated in a prime, convenient Winchester location. Featuring 3 bedrooms and 1 full bath, the interior is turn-key with newer flooring and fresh paint throughout. The living spaces are bright and inviting with lots of natural light, creating a

  Dan Whitacre Colony Realty

  208 Shenandoah Ave, Winchester, VA 22601
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  $409,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  Adams Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams I townhome offers 1,889 sq. ft. of thoughtfully designed living space, featuring 4 bedrooms, 3.5 bathrooms, and a convenient 1-car front-load garage. The modern kitchen showcases quartz countertops, stainless steel appliances, a spacious island, recessed lighting, and upgraded cabinets. Enjoy the flexibility of a finished lower-level bonus space—perfect for a rec room, home office, or

  D.R. Horton Builder

  1831 Reese Ct Unit 37025140, Winchester, VA 22601
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  $435,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,408 Sq Ft

  519 Whitacre St, Winchester, VA 22601

  Ideally located within one of Winchester’s most desirable neighborhoods, Whittier Acres, and next to Winchester Medical Center, this spacious split-level home offers exceptional convenience paired with a rare sense of privacy in a quiet, established setting. Backing to mature trees, the backyard is a peaceful retreat where birds visit regularly and an established butterfly garden awaits its

  Katie Landi Jordan Samson Properties

  519 Whitacre St, Winchester, VA 22601
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  /25

  $265,000

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft

  204 Shenandoah Ave, Winchester, VA 22601

  Great opportunity to own this 2-bed, 1-bath Winchester City charmer that sits just minutes from Shenandoah University and the Old Town walking mall. Main level living with a bright comfortable living area, an eat-in kitchen home that includes a bonus room providing flexible space for an office, playroom, fitness area, or guest room, central air and the convenience of an in-home washer & dryer

  Janet Flaherty Keller Williams Realty

  204 Shenandoah Ave, Winchester, VA 22601
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  /35

  $459,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,905 Sq Ft

  Adams II Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams II townhome features 1,905 sq. ft. of stylish and flexible living space, including 4 bedrooms, 3.5 bathrooms, and a 1-car rear-load garage. The gourmet kitchen is equipped with quartz countertops, stainless steel appliances, recessed lighting, a generous island, and sleek Duraform cabinetry. The lower-level bonus room offers endless possibilities—use it as a rec room, home office, or an

  D.R. Horton Builder

  1831 Reese Ct Unit 37025141, Winchester, VA 22601
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  $654,000

  • Studio
  • 3,511 Sq Ft

  1400 Valley Ave, Winchester, VA 22601

  Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both

  Danielle Spriggs Real Broker LLC

  1400 Valley Ave, Winchester, VA 22601
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  /17

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  369 Charles St, Winchester, VA 22601

  This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two

  Marisa Varley ERA Oakcrest Realty, Inc.

  369 Charles 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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  $340,000

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  1004 S Cameron St, Winchester, VA 22601

  Why squeeze your life into a shoebox condo or townhouse when you could actually stretch out, breathe, and live in this renovated 3-bedroom detached home for just $340,000?- -Tucked away on a private 7,840 sq. ft. lot in Winchester, this 1920s charmer gives you the one thing condos and townhouses can’t: freedom. No shared walls, no stairs, and absolutely no HOA telling you what

  Patricia Salgado Metas Realty Group, LLC

  1004 S Cameron St, Winchester, VA 22601
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  $569,900

  • 3 Beds
  • 2 Baths
  • 2,154 Sq Ft

  1412 Magruder Ct, Winchester, VA 22601

  Finally, an all-brick, very well-maintained home in The Downs of Meadow Branch. Just shut the door and go on vacation or away for the winter- the downs mows your lawn, cuts your grass, and shovels the snow.

  John Schroth Colony Realty

  1412 Magruder Ct, Winchester, VA 22601
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  $294,990

  • 3 Beds
  • 1 Bath
  • 1,205 Sq Ft

  627 Watson Ave, Winchester, VA 22601

  CLASSIC CHARM MEETS CONTEMPORARY COMFORT IN THIS FANTASTIC DUPLEX UNIT! This charming Winchester duplex unit seamlessly blends timeless character with modern conveniences, offering the perfect balance of historic flair and contemporary living. Nestled just minutes from the vibrant heart of downtown Winchester, this inviting property combines an unbeatable location with a thoughtfully-updated

  Kristin Crosby Samson Properties

  627 Watson Ave, Winchester, VA 22601
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  /35

  $448,140 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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  /36

  $428,140 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  1822 Blythe Way, Winchester, VA 22601

  1822 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA for February move-in. Our modern Adams floorplan features a 1-car garage, and along with 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

  D.R. Horton Builder

  1822 Blythe Way, Winchester, VA 22601
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  /45

  $489,900 Open Sun 3PM - 5PM

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  703 S Loudoun St, Winchester, VA 22601

  Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Check. Endless possibilities? Check!!! This amazing property, located within the Historic Winchester District, presents a one-of-a-kind opportunity to own a piece of history - all just minutes from the Old Town mall. The front of the main home dates back to 1856! You will surely fall in love with the wood

  Kristin Crosby Samson Properties

  703 S Loudoun St, Winchester, VA 22601
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  /17

  $330,000

  • 3 Beds
  • 1 Bath
  • 1,237 Sq Ft

  117 W Oates Ave, Winchester, VA 22601

  This charming bungalow, nestled in the heart of the Arthur C Oates Estate, offers a delightful blend of comfort and community. Built in 1953, this home features 3 cozy bedrooms, 1 full bathrooms, and an upstairs loft perfect for relaxation. The inviting kitchen is equipped with essential appliances, including a single oven and refrigerator, making meal preparation a breeze. The unfinished

  Jeffrey Konrady Realty ONE Group Old Towne

  117 W Oates Ave, Winchester, VA 22601
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  /29

  $279,900

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of

  Jodi Costello ERA Oakcrest Realty, Inc.

  1125 Conway St, Winchester, VA 22601
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  /16

  $339,000

  • Studio
  • 1,249 Sq Ft

  45 and 45 1/2 Race St, Winchester, VA 22601

  Investors Dream - $36,000 rental income, low maintenance, long term tenants in place. This is a great starter property for those looking to build a real estate portfolio or add to an existing one. Both apartments were completely rehabbed last year - new wiring and plumbing, new appliances, including washer and dryer, new carpet and vinyl plank flooring installed and fenced backyards. Situated

  Teri Domanski Corcoran McEnearney

  45 and 45 1/2 Race St, Winchester, VA 22601
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  /26

  $349,900

  • 3 Beds
  • 1 Bath
  • 1,196 Sq Ft

  249 West St, Winchester, VA 22601

  Great opportunity for income producing property in city limits. Property consists of 249 and 249 1/2 West Street on one lot with one w & S connection. 249 and 249 1/2 are separated by a fence . 249 1/2 consists on a block cottage that is accessed off of alley on rear of property off of National Ave. Cottage has basement, one bedroom, living room, bath and kitchen. New furnace in cottage in

  Jeff Webber Long & Foster Real Estate, Inc.

  249 West St, Winchester, VA 22601
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  /16

  $465,000

  • 4 Beds
  • 2.5 Baths
  • 1,634 Sq Ft

  21 W Pall Mall St, Winchester, VA 22601

  This inviting Winchester home offers a comfortable blend of character, functionality, and everyday convenience. The welcoming front porch creates a warm first impression and provides an ideal place to relax, unwind, or enjoy time outdoors. The fenced-in backyard offers added privacy and flexibility, making it well suited for entertaining, gardening, or simply enjoying open-air living. A private

  Sarah Reynolds Keller Williams Realty

  21 W Pall Mall St, Winchester, VA 22601
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  $685,000

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft

  1950 Melvor Ln, Winchester, VA 22601

  Step into this meticulously maintained colonial home, a testament to quality craftsmanship and thoughtful design by Richmond American Homes. Situated in the desirable Meadow Branch South neighborhood, this residence offers an exceptional living experience with a perfect balance of formal and casual spaces This home is situated in a vibrant community with easy access to major roads, shopping, and

  Kim Kroner Washington Dulles Real Estate Group

  1950 Melvor Ln, Winchester, VA 22601

Showing Results 41 - 74, Page 2 of 2