Winchester, VA Homes

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  /48

  $550,000

  • 3 Beds
  • 1.5 Baths
  • 2,177 Sq Ft

  216 Fairmont Ave, Winchester, VA 22601

  Classy colonial on the stately Fairmont Avenue with million dollar homes nearby, walking mall in close proximity with a plethora of boutique shops and eateries. The 2000 square feet is designed for comfort and coziness accented by 9ft ceilings, sunlit formal rooms, a well appointed kitchen, spacious bedrooms, adorable loft on 3rd level for a playroom/den/office, and the best part is entering your

  Dave Spence RE/MAX Roots

  216 Fairmont Ave, Winchester, VA 22601
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  /19

  $1,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft
  • Townhouse for Rent

  127 Lighthouse Ln, Winchester, VA 22602

  Location, Location, Location!!! This 3 level townhome features 3 bedrooms, 2 1/2 baths, large eat-in country kitchen with pantry, living room, office and garage with auto-opener. All appliances included. There is a deck off the dining area. Primary bedroom has full bath and walk-in closet. Community amenities include fenced pool and mowing. Landlord pays the HOA Fee. Non smoking. No

  Barbara Gaul Jim Barb Realty, Inc.

  127 Lighthouse Ln, Winchester, VA 22602
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  /14

  $364,990 Sold Oct 17, 2025

  • 1,442 Sq Ft
  • $253/SF

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  627 Laurelwood Cir, Winchester, VA 22601

  Move-In Ready Poplar Available at Laurelwood Commons in Winchester, VA! This end unit home features 3 bedrooms, 2.5 baths, 1-car garage, 1,442 square feet, October delivery, kitchen island, stainless steel appliances, powder room, LVP flooring throughout the main level and all closing costs paid with use of NVR Mortgage!* Click here to learn more about this home.

  Ryan Homes

  627 Laurelwood Cir, Winchester, VA 22601
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  /34

  Est $384,622 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,847 Sq Ft

  523 Applecroft Rd, Winchester, VA 22601

  523 Applecroft Rd, Winchester, VA 22601
• 

  

  

  /51

  $430,000

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

  133 Cardinal Ln, Winchester, VA 22602

  Welcome to this well maintained and fully remodeled split foyer, tucked away in a private cul-de-sac setting. Located just minutes from route 7 and I-81, commuting will be a breeze. Brand new LVP flooring flow seamlessly across both levels, as does the neutral colors throughout. The spacious eat-in kitchen is the heart of the home-with white cabinetry, granite countertops, tile backsplash and

  Heloisa Amar Samson Properties

  133 Cardinal Ln, Winchester, VA 22602
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  /31

  $2,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,220 Sq Ft
  • Townhouse for Rent

  290 Sage Cir, Winchester, VA 22603

  Welcome Home! This move-in ready end-unit townhome in Regents Crest sits on a desirable corner lot with a larger yard that backs to a wooded nature path and walking trail for extra privacy. Offering 3 bedrooms, 2.5 baths, and a 1-car garage, this bright and open home is designed for comfort and convenience.The entry level includes a welcoming foyer with a large coat closet, garage access,

  Rachel Olsen Keller Williams Realty

  290 Sage Cir, Winchester, VA 22603
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  /20

  $193,000 Sold Oct 17, 2025

  • Land
  • 10 Acres
  • $19,300 per Acre

  • 29 Days On Market

  0 Adams Rd Unit VAFV2034928, Winchester, VA 22603

  Two building lots! These two lots totaling 10-acres are absolutely pristine and just minutes from downtown Winchester. The property features large frontage along quiet and paved Adams Road and Dry Creek Lane. The land features four separate fields surrounded by ample hardwoods. A wet-weather stream bisects the easily walkable property. Wildlife is abundant, including numerous deer and

  Jeffrey Konrady Realty ONE Group Old Towne

  0 Adams Rd Unit VAFV2034928, Winchester, VA 22603
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  /54

  Est $532,009 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  604 Kernstown Ct, Winchester, VA 22601

  604 Kernstown Ct, Winchester, VA 22601
• 

  

  /25

  $384,000

  • 3 Beds
  • 1 Bath
  • 1,918 Sq Ft

  1327 Front Royal Pike, Winchester, VA 22602

  Don't miss this opportunity to own this wonderful, well maintained home. Just minutes from town, this home has hardwood floors throughout and a bright, sunny sunroom facing the spacious back yard. There is a huge shop in the back that would be prefect for the car enthusiast or for additional garage space. The woodstove in the basement rec room would save on heating costs and includes a cute art

  Katherine Solenberger Colony Realty

  1327 Front Royal Pike, Winchester, VA 22602
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  /21

  $2,400 per month

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Townhouse for Rent

  172 Munsee Cir, Winchester, VA 22602

  Brand New Luxury End Unit Townhome!! Excellent Location!! Be the first to live in this stunning, brand-new three-level townhome at The Retreat at Winding Creek! This Adams design offers 1,889 sq. ft. of stylish and spacious living, perfect for modern families and professionals alike. Features You'll Love: 4 Bedrooms & 3.5 Bathrooms: Enjoy ample space and privacy for everyone. Modern Kitchen:

  venkateswararao nekkalapudi Alluri Realty, Inc.

  172 Munsee Cir, Winchester, VA 22602
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  /48

  $574,900 Sold Oct 17, 2025

  • 2,602 Sq Ft
  • $221/SF
  • 83 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1995

  1629 Pondview Dr, Winchester, VA 22601

  Discover tranquility and spacious living in this exceptional 4-bedroom, 3.5-bath home, with a main-level primary suite, ideally situated on one half of an acre backing to picturesque trees and wide-open fields. From the moment you step inside, you'll appreciate the meticulously maintained interior and inviting open floor plan. The living room features a cathedral ceiling and a cozy gas fireplace,

  Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

  1629 Pondview Dr, Winchester, VA 22601
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  /90

  Est $541,978 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,632 Sq Ft

  627 Pritchards Hill Ct, Winchester, VA 22601

  627 Pritchards Hill Ct, Winchester, VA 22601
• 

  

  /46

  $599,900

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  289 Westview Dr, Winchester, VA 22603

  Welcome to your private contemporary retreat at 289 Westview Drive in Winchester, VA! This truly exceptional property offers the ultimate escape, situated on over 13 magnificent acres with gorgeous mature trees, stunning views, and unparalleled peace and quiet. Step inside the sun-filled main level, featuring an open layout that seamlessly connects the living room, dining room, and kitchen.

  Dan Whitacre Colony Realty

  289 Westview Dr, Winchester, VA 22603
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  /10

  $1,630 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  129 8 Brookland Terrace Unit 8, Winchester, VA 22602

  Open Tuesday Nov. 4, 12:00-1:15. Freshly painted and new flooring, clean and move-in ready for immediate occupancy. New LVP flooring throughout, new flooring in the bathrooms and new toilets. Light-filled unit with outdoor balcony. New stove and dishwasher just installed. Dogs case-by-case, no cats. Great location just off Rt. 7. Two bedrooms, two full baths, balcony. Credit 680+, 3X income, and

  Leslie Carpenter Compass

  129 8 Brookland Terrace Unit 8, Winchester, VA 22602
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  /8

  $225,000 Sold Oct 17, 2025

  • Land
  • 5.99 Acres
  • $37,563 per Acre

  • 40 Days On Market

  Lot 6 Cedar Creek Grade, Winchester, VA

  Beautiful lot in a small neighborhood on the very desirable west side of Winchester off Cedar Creek Grade! Lot is already perked for an alternative septic system. This opportunity doesn’t come along often! Rolling hills with beautiful surroundings and views. The location is less than 10 minutes to grocery stores, downtown Winchester, or Winchester Medical Center. It’s also located within 2

  Lori Bales Keller Williams Realty

  Lot 6 Cedar Creek Grade, Winchester, VA
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  /49

  Est $547,085 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft

  2833 Saratoga Dr, Winchester, VA 22601

  2833 Saratoga Dr, Winchester, VA 22601
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  /61

  $799,999

  • 4 Beds
  • 3.5 Baths
  • 4,461 Sq Ft

  162 Janes Way, Winchester, VA 22602

  Discover this beautifully updated home on 5 private acres in the sought-after Brookneill Subdivision—just minutes from Winchester! The home includes numerous updates, including new hardwood floors through the living room, and stairs, new kitchen cabinets, countertops, sink, and appliances. Upstairs features two huge bedrooms with new carpet, the finished basement offers new luxury vinyl plank

  Tanner Pack RE/MAX Roots

  162 Janes Way, Winchester, VA 22602
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  /58

  $3,000 per month

  • 4 Beds
  • 3 Baths
  • 3,060 Sq Ft
  • House for Rent

  209 N Washington St, Winchester, VA 22601

  Live in the heart of historic Winchester! This beautifully maintained 1853 home on Washington Street offers more than just a place to live—it’s a lifestyle. With over 3,000 square feet of finished space, this one-of-a-kind rental blends timeless character with modern updates just blocks from the Old Town Walking Mall and steps from the Apple Blossom Parade Route. Inside, you’ll find 10-foot

  Chris Roszko Colony Realty

  209 N Washington St, Winchester, VA 22601
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  /34

  $450,000 Sold Oct 17, 2025

  • 2,052 Sq Ft
  • $219/SF
  • 7 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2016

  711 S Braddock St, Winchester, VA 22601

  This well-maintained 3-bedroom, 3.5-bath home offers bright, open living spaces with plenty of natural light. The main level features a spacious living room, an updated kitchen with stainless steel appliances, and a dining area. The back patio features an open area and green space with a fenced backyard—great for relaxing or entertaining. Upstairs, you’ll find a generous primary suite with a full

  Dave Spence RE/MAX Roots

  711 S Braddock St, Winchester, VA 22601
• 

  

  /55

  Est $550,629 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,742 Sq Ft

  2821 Saratoga Dr, Winchester, VA 22601

  2821 Saratoga Dr, Winchester, VA 22601
• 

  

  /46

  $569,000

  • 4 Beds
  • 2.5 Baths
  • 2,275 Sq Ft

  326 Lehigh Dr, Winchester, VA 22602

  Welcome to 326 Lehigh Drive, a stunning, like-new home in a prime Winchester location—a pristine, only 2-year-old residence that feels brand new! This beautiful 4-bedroom, 2.5-bathroom home boasts exceptional high-end finishes and a modern, desirable design throughout. The interior showcases an airy open-concept layout and a stylish neutral color palette that allows any decorating style to

  Dan Whitacre Colony Realty

  326 Lehigh Dr, Winchester, VA 22602
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  /15

  $1,750 per month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  307 Willowbrook Ct, Winchester, VA 22602

  Located in the highly sought-after East End of Winchester, this exceptional all-brick end-unit townhome is just minutes from Rt. 7 and I-81, offering an unbeatable commuter location. Close to shopping and only a short drive to the charming downtown Winchester walking mall, this home is perfectly positioned for convenience and comfort.Meticulously maintained by the owners, this move-in ready

  Jeff Boppe Long & Foster Real Estate, Inc.

  307 Willowbrook Ct, Winchester, VA 22602
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  /63

  $805,000 Sold Oct 17, 2025

  • 3,942 Sq Ft
  • $204/SF
  • 59 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1981

  756 Brookneil Dr, Winchester, VA 22602

  Some homes are lived in. Others are lived for. This one? It's the kind of place you wait for—the kind you watch for, and when it finally hits the market, you clear your calendar to see it.Set deep into over 9 private wooded acres, at the very end of a quiet cul-de-sac, this completely rebuilt ranch-style home in Winchester offers something you rarely find anymore: total privacy, modern

  Alexander Bracke Real Broker, LLC

  756 Brookneil Dr, Winchester, VA 22602
• 

  

  /53

  Est $509,623 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,596 Sq Ft

  2832 Saratoga Dr, Winchester, VA 22601

  2832 Saratoga Dr, Winchester, VA 22601
• 

  

  /45

  $400,000

  • 4 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  100 Winns Cir, Winchester, VA 22602

  Welcome home to Winns Circle! This lovely home is well maintained and ideally located on a corner lot near all that Winchester has to offer. With an open first floor floorplan and lots of room for entertaining, from the large eat in kitchen, to the spacious living room and walkout decking, this home is has so many possibilities! Upstairs hosts four large rooms, ready for hobby spaces, bedrooms,

  Nicole Lewis Coldwell Banker Premier

  100 Winns Cir, Winchester, VA 22602
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  /50

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • House for Rent

  709 Dicks Hollow Rd, Winchester, VA 22603

  Welcome to this private gem nestled on a corner lot in beautiful Winchester, VA! This stunning 3-bedroom, 2-bath home offers the perfect balance of modern upgrades, comfort, and peace of mind. Step inside to find a fully remodeled primary bathroom featuring a luxurious walk-in shower — a spa-like retreat in the comfort of your own home. The entire house benefits from a state-of-the-art water

  Fehiber Rosario NBI Realty, LLC

  709 Dicks Hollow Rd, Winchester, VA 22603
• 

  

  /65

  $445,000 Sold Oct 17, 2025

  • 1,950 Sq Ft
  • $228/SF
  • 3 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1999

  113 Whipp Dr, Winchester, VA 22602

  This Is It! This sweet 4 bed, 2.5 bath home is ready for You! The moment you enter this charming single-family property you will feel right at home! From the full length front porch step into the open entry and join us in the living area, overlooking the front yard. Beyond that the family room expands right into your eat-in kitchen, all looking out onto your great deck and expansive backyard! The

  Cindy Greenya Keller Williams Realty

  113 Whipp Dr, Winchester, VA 22602
• 

  

  /50

  Est $463,805 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,968 Sq Ft

  2612 Stonegate Dr, Winchester, VA 22601

  2612 Stonegate Dr, Winchester, VA 22601
• 

  

  /9

  $269,900

  • 2 Beds
  • 1.5 Baths
  • 1,251 Sq Ft

  2918 Sorrell Ct, Winchester, VA 22601

  Welcome to your new home! This beautifully maintained 2 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half bath. Upstairs you will find two generously sized bedrooms with large

  Amber Jenkins Century 21 Redwood Realty

  2918 Sorrell Ct, Winchester, VA 22601
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  /27

  $2,100 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 203, Winchester, VA 22601

  This one bedroom and one bath apartment overlooks the roof onto Vibrissa's beautiful courtyard and mural. You will have a front row seat to live music and super quick access to tons of Apple Blossom events! Easy to clean and maintain LVP flooring has been installed throughout. The kitchen features a beautiful island, tons of cabinet space, with plenty of drawers for easy organizing, and stainless

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 203, Winchester, VA 22601
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  /49

  $667,000 Sold Oct 17, 2025

  • 2,998 Sq Ft
  • $222/SF
  • 25 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  441 Fair Ln, Winchester, VA 22603

  Discover your perfect retreat at 441 Fair Ln, Winchester, VA 22603, in the peaceful Fairway Estates neighborhood! This stunning 4-bedroom, 2.5-bathroom single-family home spans 2,998 square feet on a sprawling 5.54-acre lot, offering a blend of modern luxury and serene country living. Built in 2000, this meticulously updated residence is just minutes from Historic Downtown Winchester and major

  Caleb Fowler Samson Properties

  441 Fair Ln, Winchester, VA 22603
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  /46

  Est $432,888 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,961 Sq Ft

  2641 Stonegate Dr, Winchester, VA 22601

  2641 Stonegate Dr, Winchester, VA 22601
• 

  

  /22

  $235,000

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  157 Brookland Terrace Unit 11, Winchester, VA 22602

  Top-Floor Gem with Vaulted Ceilings & Modern Upgrades! Welcome home to this bright and airy 2-bedroom, 2-bath top-level condo that perfectly blends comfort, style, and convenience. Step inside and be greeted by soaring vaulted ceilings and abundant natural light streaming through multiple skylights, creating an inviting and open atmosphere.The spacious kitchen is a chef’s delight, featuring sleek

  Becky Green Samson Properties

  157 Brookland Terrace Unit 11, Winchester, VA 22602
• 

  

  /13

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  5 Brookland Ct, Winchester, VA 22602

  Well maintained 2 bedroom 2 bath unit on 2nd floor. Gas fireplace and private balcony. Ready for move in. Landlord requires Minimum credit score of 700 and income of 3X the rent. Pets are welcome case by case. No prior evictions. Apply online using RentSpree link. All adults over 18 must apply $35 application fee per applicant.

  Hushai Mesfin Samson Properties

  5 Brookland Ct, Winchester, VA 22602
• 

  

  /39

  $513,579 Sold Oct 17, 2025

  • 2,181 Sq Ft
  • $235/SF
  • 28 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  115 Wagtail Ln, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1030 at Hiatt Pointe—a two-car, front-load garage END UNIT VILLA with three bedrooms, two full bathrooms, and one half bathroom is ready for move-in IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this

  Shannon L Bray Pearson Smith Realty, LLC

  115 Wagtail Ln, Winchester, VA 22603
• 

  

  /21

  Est $393,729 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  2627 Stonegate Dr, Winchester, VA 22601

  2627 Stonegate Dr, Winchester, VA 22601
• 

  

  /25

  $284,500

  • 2 Beds
  • 1 Bath
  • 572 Sq Ft

  177 Dicks Hollow Rd, Winchester, VA 22603

  Adorable and fully renovated 2-bedroom, 1-bath bungalow just minutes from Winchester Medical Center! You’ll love the spacious open layout that connects the living room and kitchen, complete with brand-new stainless steel appliances and beautiful LVP flooring throughout. The large bedrooms offer plenty of space to relax, and the laundry/mudroom adds extra convenience. The bright bathroom features

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  177 Dicks Hollow Rd, Winchester, VA 22603
• 

  /2

  $3,000 per month

  • 4 Beds
  • 3 Baths
  • 2,658 Sq Ft
  • House for Rent

  557 Bellview Ave, Winchester, VA 22601

  Welcome to 557 Bellview Ave. A beautifully remodeled split-level home featuring 4 bedrooms, 3 bathrooms, 2 sunrooms, a deck and new patio with built-in firepit, overlooking Abram's creek. Back yard is equipped with an invisible fence, and landlord will consider pets on a case by case basis. Professional photos to come.

  Matthew Berry MarketPlace REALTY

  557 Bellview Ave, Winchester, VA 22601
• 

  

  /29

  $519,990 Sold Oct 16, 2025

  • 2,415 Sq Ft
  • $215/SF

  • 5 Beds
  • 3 Baths
  • Built 2025

  100 Manasquan Way, Winchester, VA 22602

  This new home in Winchester is situated on a corner homesite and is move-in ready! Discover the perfect blend of space, function, and style in the Elm—a thoughtfully designed 2,415 sq. ft. two-story home featuring 5 bedrooms, 3 full bathrooms, a versatile loft, and a 2-car garage. Step into a welcoming foyer that opens to a bright, open-concept living area. The heart of the home is the spacious

  D.R. Horton

  100 Manasquan Way, Winchester, VA 22602
• 

  

  /28

  Est $450,435 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,580 Sq Ft

  314 Stonehenge Rd, Winchester, VA 22601

  314 Stonehenge Rd, Winchester, VA 22601

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