Winchester County VA Homes for Sale

• 

  

  

  /10

  $399,000

  • Land
  • 3,920 Sq Ft
  • $4,433,333 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
• 

  

  

  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  540 Bellview Ave, Winchester, VA 22601

  Attention investors! Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
• 

  

  

  /31

  $499,900

  $60K PRICE DROP

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

  110 Russelcroft Rd, Winchester, VA 22601

  Welcome to 110 Russellcroft Road, a beautifully updated 4-bedroom, 3-full-bath ranch-style home in the established Cedarmeade community of Winchester, VA. Offering approximately 3,000 square feet of finished living space including the finished lower level, this home combines comfortable everyday living with the flexibility today's buyers are looking for.The main level features warm

  Grace Mooney Coldwell Banker Premier

  110 Russelcroft Rd, Winchester, VA 22601
• 

  

  

  /142

  $760,000

  • 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. Create wealth with this income producing opportunity.The main level features a generously sized

  Amanda Slate Keller Williams Realty

  769 Seldon Dr, Winchester, VA 22601
• 

  

  

  /10

  $750,000

  • Studio
  • 3,484 Sq Ft

  224 Sharp St, Winchester, VA 22601

  Rare Historical Winchester Investment Opportunity – Three Properties in One LocationAn outstanding investment opportunity awaits in the heart of Winchester City. This unique portfolio comprises three properties positioned along the same street, offering exceptional potential for developers, investors, or those seeking a landmark project for multi-unit rentals or commercial development. Both

  Stacey Rowe Real Broker LLC

  224 Sharp St, Winchester, VA 22601
• 

  

  /78

  $245,000

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,068 Sq Ft

  103 E Germain St, Winchester, VA 22601

  Roof replaced in 2020. NEW PRICE!Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area,

  RoxAnn Grimes RE/MAX Roots

  103 E Germain St, Winchester, VA 22601
• 

  

  /95

  $355,000

  • 2 Beds
  • 2 Baths
  • 1,234 Sq Ft

  1847 Melvor Ln, Winchester, VA 22601

  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, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer

  Lisette Turner Century 21 Redwood Realty

  1847 Melvor Ln, Winchester, VA 22601
• 

  

  /26

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,844 Sq Ft

  1310 Whittier Ave, Winchester, VA 22601

  Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a

  Sarah Hott Realty ONE Group Old Towne

  1310 Whittier Ave, Winchester, VA 22601
• 

  

  /64

  $349,000

  $26K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,474 Sq Ft

  805 Pennsylvania Ave, Winchester, VA 22601

  Classic brick ranch just minutes from Old Town Winchester, offering one-level living, original hardwood floors, a detached garage, private backyard and a full basement with room to expand. Nearly a third-acre lot, this home offers an opportunity to personalize a solid Winchester home in a convenient location.The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen,

  Sherry Santmyer Hunt Country Sotheby's International Realty

  805 Pennsylvania Ave, Winchester, VA 22601
• 

  

  /45

  $315,000

  $35K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  913 Orchard Hill Dr, Winchester, VA 22601

  New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter

  Dallas Croft Samson Properties

  913 Orchard Hill Dr, Winchester, VA 22601
• 

  /2

  $199,900

  • Land
  • 6,969 Sq Ft
  • $1,249,375 per Acre

  1415 Ramseur Ln, Winchester, VA 22601

  Steve DuBrueler Coldwell Banker Premier

  1415 Ramseur Ln, Winchester, VA 22601
• 

  /2

  $625,000

  Coming Soon Oct 2

  • Studio
  • 4,146 Sq Ft

  25 W Boscawen St, Winchester, VA 22601

  Awesome income-producing multi-unit property in the heart of downtown Winchester. This stately red brick building delivers immediate cash flow with a great documented CAP rate and all three units currently occupied with tenants paying all utilities. High ceilings and abundant natural light create desirable living spaces. Located just a half-block from the Winchester walking mall, residents enjoy

  Teri Domanski Your Home Sold Guaranteed Realty - East LLC

  25 W Boscawen St, Winchester, VA 22601
• 

  

  /17

  $279,000

  $16K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1314 S Braddock St, Winchester, VA 22601

  1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room

  Jacqueline Moore Open Door Brokerage, LLC

  1314 S Braddock St, Winchester, VA 22601
• 

  /2

  $305,500

  Open House 10/17 Coming Soon Sep 30

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft

  3 S Euclid Ave, Winchester, VA 22601

  Charming 1955 home offering timeless character, inviting curb appeal, and a versatile floor plan! This 3-bedroom, 2-full-bath home features one bedroom conveniently located on the main level, along with a dedicated office that provides a great space for working from home, hobbies, or additional flex space. One of the two full bathrooms is brand new, adding a fresh modern touch to this classic

  Tina Jacobin Main Street Realty

  3 S Euclid Ave, Winchester, VA 22601
• 

  

  /52

  $369,990

  New Construction Open Sun 1PM - 4PM

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  229 Monteith Dr, Winchester, VA 22601

  ***OFFERING UP TO $12,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*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 flex space in the finished lower

  Brittany Newman DRB Group Realty, LLC

  229 Monteith Dr, Winchester, VA 22601
• 

  

  /23

  $127,750

  • Land
  • 8.11 Acres
  • $15,752 per Acre

  0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602

  Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by making for easy and

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602
• 

  

  /29

  $299,500

  • 3 Beds
  • 1.5 Baths
  • 1,138 Sq Ft

  621 Watson Ave, Winchester, VA 22601

  Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas.The updated kitchen features new cabinetry and stainless steel

  Caleb Fowler Samson Properties

  621 Watson Ave, Winchester, VA 22601
• 

  

  /52

  $569,000

  • 4 Beds
  • 4 Baths
  • 2,489 Sq Ft

  687 Woodland Ave, Winchester, VA 22601

  ONE-OF-A-KIND HOME WITH INCREDIBLE FLEXIBILITY! This custom all-brick Winchester home offers a layout you simply don't find every day—4 bedrooms, 4 full baths, two main-level bedrooms, flexible private living spaces, a detached 2-car garage and NO HOA!Step inside to a bright, welcoming floor plan featuring beautiful hardwood floors, abundant natural light, custom built-ins and a cozy gas

  Katy Donovan Keller Williams Realty

  687 Woodland Ave, Winchester, VA 22601
• 

  

  /33

  $348,000

  $12K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  302 Wentworth Dr, Winchester, VA 22601

  Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on

  Heloisa Amar Samson Properties

  302 Wentworth Dr, Winchester, VA 22601
• 

  

  /35

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  112 W Germain St, Winchester, VA 22601

  100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025!This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic

  Amanda Magana RE/MAX Roots

  112 W Germain St, Winchester, VA 22601
• 

  

  /32

  $399,900

  $29K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,419 Sq Ft

  118 1/2 E Cork St, Winchester, VA 22601

  Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural

  Janet Flaherty Keller Williams Realty

  118 1/2 E Cork St, Winchester, VA 22601
• 

  

  /33

  $299,900

  • 3 Beds
  • 1.5 Baths
  • 1,648 Sq Ft

  1013 Orchard Hill Dr, Winchester, VA 22601

  Updated, move-in ready, and waiting for you to make it your own! Welcome to 1013 Orchard Hill Dr. Tucked away in a charming, established Winchester neighborhood with no HOA, this inviting townhome combines a clean, comfortable style with many of the big-ticket improvements already taken care of. Outside, you'll find a brand-new roof and vinyl siding, fresh landscaping, and an updated rear deck

  Josh Feltner Realty ONE Group Old Towne

  1013 Orchard Hill Dr, Winchester, VA 22601
• 

  

  /33

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft

  1412 S Loudoun St, Winchester, VA 22601

  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, this property blends classic charm with thoughtful updates throughout. The main level features a bright, welcoming layout perfect for everyday living, while the lower level opens the door to exceptional flexibility — complete

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1412 S Loudoun St, Winchester, VA 22601
• 

  

  /19

  $393,495

  New Construction

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

  652 Arden Ct, Winchester, VA 22601

  652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  652 Arden Ct, Winchester, VA 22601
• 

  

  /88

  $639,900

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,179 Sq Ft

  1529 Dalton Place, Winchester, VA 22601

  Roof 2017 - Water Heater 2017 - HVAC 2023. Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the

  RoxAnn Grimes RE/MAX Roots

  1529 Dalton Place, Winchester, VA 22601
• 

  

  /51

  $415,000

  $5K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,004 Sq Ft

  109 Marlow Ct, Winchester, VA 22602

  Don't miss this nearly new townhouse in Rossum Crossing! With 4 bedrooms, 3.5 bathrooms, over 2,000 square feet of finished space, and a one-car garage, this home offers plenty of room and a great layout for everyday living. The lower level features a private bedroom with its own full bathroom, including a tiled walk-in shower, along with direct access to the rear yard. Upstairs, you'll find a

  Crystal Dudurich ERA Liberty Realty

  109 Marlow Ct, Winchester, VA 22602
• 

  

  /37

  $349,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,219 Sq Ft

  1856 Melvor Ln, Winchester, VA 22601

  Low-maintenance, one-level living in Winchester! Located on a corner lot in an established 55+ community, 1856 Melvor Lane offers 2 bedrooms, 2 full baths, an open floor plan, and thoughtful updates throughout.Cathedral ceilings and natural light give the main living area an open, airy feel, while luxury vinyl plank flooring extends through most of the home. Fresh interior paint and

  Natasha Roberts Realty ONE Group Old Towne

  1856 Melvor Ln, Winchester, VA 22601
• 

  

  /40

  $439,900

  • 3 Beds
  • 2 Baths
  • 1,307 Sq Ft

  153 Fox Dr, Winchester, VA 22601

  Welcome home to this beautifully maintained 3-bedroom, 2-bath home offering comfort, convenience, and exceptional outdoor living. Ideally located just minutes from shopping, schools, the hospital, and other everyday amenities, this home combines a prime location with thoughtful updates.Inside, you'll find two recently remodeled bathrooms featuring modern finished and stylish upgrades. The

  Amber Jenkins Century 21 Redwood Realty

  153 Fox Dr, Winchester, VA 22601
• 

  

  /38

  $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
• 

  

  /8

  $289,900

  • 2 Beds
  • 1.5 Baths
  • 1,024 Sq Ft

  2640 Limestone Ct, Winchester, VA 22601

  Nestled in the charming City of Winchester, this exquisite end-of-row townhouse has undergone a remarkable transformation, with major renovations completed in 2026 that elevate it to a new standard of luxury living. The timeless Colonial architectural style, complemented by a classic brick exterior, exudes elegance and warmth, inviting you to experience a lifestyle of comfort and sophistication.

  Meridee Powars Link Realty Services LLC

  2640 Limestone Ct, Winchester, VA 22601
• 

  

  /31

  $295,000

  $64K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  608 Dunlap St, Winchester, VA 22601

  Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort.

  Richard Butcher Coldwell Banker Premier

  608 Dunlap St, Winchester, VA 22601
• 

  

  /6

  $70,000

  • Land
  • 3,049 Sq Ft
  • $1,000,000 per Acre

  548 Fremont St, Winchester, VA 22601

  Build-ready lot in Winchester — a true blank canvas with water and sewer hookups already in place. Minutes to Old Town and I-81. Bring your builder and your vision!

  RoxAnn Grimes RE/MAX Roots

  548 Fremont St, Winchester, VA 22601
• 

  

  /87

  $1,239,000

  • 4 Beds
  • 7.5 Baths
  • 5,662 Sq Ft

  1022 Heth Place, Winchester, VA 22601

  This amazing property is ready for you! Located close to Winchester Medical Center, Churches, Shopping, Historic Downtown Winchester, John Kerr Elementary School, and John Handley High School. This property is beautifully landscaped with plush gardens, a koi pond, waterfalls, a large pool, pool room, large deck overlooking the property, and a fenced backyard lined with mature trees for privacy.

  Cynthia Butler Samson Properties

  1022 Heth Place, Winchester, VA 22601
• 

  

  /73

  $615,000

  Open Sun 12PM - 2PM

  • 5 Beds
  • 3.5 Baths
  • 3,626 Sq Ft

  922 Wayne Dr, Winchester, VA 22601

  Welcome home to this beautifully updated brick-front residence in the City of Winchester, where a thoughtful floor plan, generous living spaces with 9' ceilings on the main and upper levels, and meaningful improvements come together across three finished levels.The main level is designed for connection and comfort, beginning with a two-story foyer that opens into an airy, open-concept layout.

  Katrina Smith Samson Properties

  922 Wayne Dr, Winchester, VA 22601
• 

  

  /40

  $359,990

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  237 Monteith Dr, Winchester, VA 22601

  ***OFFERING UP TO $12,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*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 privacy and peaceful views.

  Brittany Newman DRB Group Realty, LLC

  237 Monteith Dr, Winchester, VA 22601
• 

  

  /13

  $274,000

  $25K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft

  519 Virginia Ave, Winchester, VA 22601

  This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great "Handyman's Delight" as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water

  Katherine Solenberger Colony Realty

  519 Virginia Ave, Winchester, VA 22601
• 

  

  /23

  $424,990

  New Construction $5K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 2,094 Sq Ft

  126 Swansong Place, Winchester, VA 22603

  BUILDER OFFERING BELOW MARKET RATE FINANCING ON THIS MOVE IN READY HOME!!Exceptional value for a 4‑bedroom END‑UNIT townhome is ready for move‑in! Brand‑new construction offers modern style and comfort with oak stairs with upgraded railings and durable LVP flooring throughout the main level. Backing to open space in the newest section of Snowden Bridge, this spacious home includes a flexible

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  126 Swansong Place, Winchester, VA 22603
• 

  

  /30

  $379,900

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
• 

  

  /69

  $605,000

  • 9 Beds
  • 4 Baths
  • 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
• 

  

  /22

  $599,950

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,948 Sq Ft

  446 N Loudoun St, Winchester, VA 22601

  Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking

  Lawrence Lessin Homes By Owner, Inc.

  446 N Loudoun St, Winchester, VA 22601

Showing Results 41 - 80, Page 2 of 3