Winchester, VA Homes

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  /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
• 

  

  

  /10

  $1,550 per month

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

  3 Brookland Ct, Winchester, VA 22602

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  3 Brookland Ct, Winchester, VA 22602
• 

  

  

  /31

  $380,000 Sold Oct 16, 2025

  • 1,686 Sq Ft
  • $225/SF
  • 37 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2002

  109 Cranberry Ct, Winchester, VA 22602

  Beautiful 2 bedroom, 2 full bath home in one of Winchester's most sought after 55+ communities, Cross Creek! Open and spacious, with a cozy fireplace in the living room, bright and sunny eat-in kitchen has plenty of cabinets and ample room for table and chairs. Dining area is open to the large living room, with a bonus fully enclosed sunroom overlooking the fenced backyard! Amenities include

  Meghan Pachas Realty ONE Group Old Towne

  109 Cranberry Ct, Winchester, VA 22602
• 

  

  

  /55

  Est $453,958 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,630 Sq Ft

  313 W Tevis St, Winchester, VA 22601

  313 W Tevis St, Winchester, VA 22601
• 

  

  

  /42

  $419,000

  • 3 Beds
  • 2 Baths
  • 2,325 Sq Ft

  1133 Tomahawk Trail, Winchester, VA 22602

  Nestled in the serene Shawneeland community, this exquisite chalet-style residence offers a perfect blend of rustic charm and modern comfort. Set against a backdrop of breathtaking mountain views and scenic vistas, this home is a sanctuary for those seeking tranquility and an exclusive lifestyle. As you approach the property, the warm cedar exterior invites you in, exuding a sense of timeless

  Sue Goodwin Long & Foster Real Estate, Inc.

  1133 Tomahawk Trail, Winchester, VA 22602
• 

  

  /56

  $525,000 Sold Oct 16, 2025

  • 3,982 Sq Ft
  • $132/SF
  • 2 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1997

  202 Senseny Glen Dr, Winchester, VA 22602

  Located in the sought after neighborhood of Senseny Glen, this meticulously cared for rancher has been thoughtfully maintained by the current owners, going above and beyond to ensure it’s in outstanding condition. Offering over 3,700 square feet of finished living space on a quiet corner lot, it’s also conveniently located near restaurants, shopping, local schools, Route 7, and I-81. Inside,

  Liz Owings RE/MAX Roots

  202 Senseny Glen Dr, Winchester, VA 22602
• 

  

  /24

  Est $267,484 Not Listed For Sale

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

  2651 Limestone Ct, Winchester, VA 22601

  2651 Limestone Ct, Winchester, VA 22601
• 

  

  /62

  $569,990

  • 4 Beds
  • 3.5 Baths
  • 3,132 Sq Ft

  308 Lehigh Dr, Winchester, VA 22602

  PRICE REDUCED + SELLER OFFERING $10K TOWARD CLOSING OR PURCHASERS RATE BUY DOWN for contract before end of year!! Welcome to 308 Lehigh Drive, a beautifully updated and move-in ready home offering the perfect blend of space, style, and comfort. Built in 2023 - this modern, open-concept floor plan is filled with natural light and designed for effortless everyday living and impressive entertaining.

  Sean Smith Real Broker, LLC

  308 Lehigh Dr, Winchester, VA 22602
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  /6

  $12,000 Sold Oct 16, 2025

  • Land
  • 0.26 Acre
  • $46,154 per Acre

  • 546 Days On Market

  0 12 Elk Trail Unit VAFV2018238, Winchester, VA 22602

  Approved building lot under 20 minutes to Winchester Medical Center I 81 or I 66 in Mountain Falls Park. A quiet rural community, known for its close proximity to town, waterfalls, and mountain views for miles. This lot is very buildable, it is level, has a current survey, recorded plat and a recorded AOSE certification letter for a 3 bedroom house. Covenants and restrictions are in the

  Nadeem Helfer Corcoran McEnearney

  0 12 Elk Trail Unit VAFV2018238, Winchester, VA 22602
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  /25

  Est $286,396 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,145 Sq Ft

  2668 Limestone Ct, Winchester, VA 22601

  2668 Limestone Ct, Winchester, VA 22601
• 

  

  /38

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  405 1/2 Elm St, Winchester, VA 22601

  Seller prefers to close with FD Title.This adorable home sits on in a prime location very close to the downtown Winchester City! This renovated house features 3 bedrooms and 2 full bathrooms in a peaceful and vibrant setting. Property is vacant. You will find a renovated kitchen connected to the dining area. The hardwood floors flow through the rest of the home and the 3 bedrooms are spacious

  CATO ZEGARRA First Decision Realty LLC

  405 1/2 Elm St, Winchester, VA 22601
• 

  

  /40

  $340,000 Sold Oct 15, 2025

  • 1,376 Sq Ft
  • $247/SF
  • 3 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1988

  101 Maloy Dr, Winchester, VA 22602

  101 Maloy Dr, Winchester, VAWelcome to 101 Maloy Drive, a well-maintained single-family home on a 0.43-acre lot in Winchester. Built in 1988, this property offers 2 bedrooms, 2.5 baths, and approximately 1,376 finished square feet with a practical layout. The main level includes a spacious living area, functional kitchen, and primary suite with a walk-in closet. A bonus room provides

  Steve Bingham Realty ONE Group Capital

  101 Maloy Dr, Winchester, VA 22602
• 

  

  /11

  Est $263,211 Not Listed For Sale

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

  2639 Limestone Ct, Winchester, VA 22601

  2639 Limestone Ct, Winchester, VA 22601
• 

  

  /35

  $299,000

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft

  239 Chestnut St, Winchester, VA 22601

  ******Seller is offering up to $9K for closing costs with a full offer******239 Chestnut Street is a charming rancher in the heart of Winchester. 2 bedrooms, 1 bath, a large rear deck, eat in kitchen, laundry room could be converted into a third bedroom. Building in the back yard could be used as storage or a 1 car garage. This is a solid starter or downsizing home convenient to

  William Wertz Wildhawks Realty LLC

  239 Chestnut St, Winchester, VA 22601
• 

  

  /25

  $289,000 Sold Oct 15, 2025

  • 1,296 Sq Ft
  • $223/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1996

  505 Emily Ln, Winchester, VA 22602

  Charming Townhouse in the Beautiful Countryside of Winchester, VAMove-in ready! This spacious upper-level townhouse features:Three large bedroomsTwo full bathroomsGleaming hardwood floors throughoutFreshly painted interiorModern kitchen with stainless steel appliancesLarge backyard — perfect for relaxing or entertainingTwo reserved parking spacesEnjoy

  Trancito Laureano RE/MAX Gateway

  505 Emily Ln, Winchester, VA 22602
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  /30

  Est $345,093 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,264 Sq Ft

  2626 Cornerstone Cir, Winchester, VA 22601

  2626 Cornerstone Cir, Winchester, VA 22601
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  /62

  $575,000

  • 5 Beds
  • 3.5 Baths
  • 5,298 Sq Ft

  212 Fairfield Dr, Winchester, VA 22602

  Welcome to 212 Fairfield Drive, a sprawling, all-brick rancher offering an incredible amount of space and comfort in a highly sought-after Winchester location. This home is a commuter's dream, providing easy access to I-81 and other major commuter routes all while offering a peaceful, private retreat. The main level is designed for both entertaining and daily living, featuring a formal dining

  Dan Whitacre Colony Realty

  212 Fairfield Dr, Winchester, VA 22602
• 

  

  /11

  $12,000 Sold Oct 14, 2025

  • Land
  • 0.27 Acre
  • $44,444 per Acre

  • 2 Days On Market

  0 Graywolf Trail, Winchester, VA 22602

  This lovely lot in the quiet neighborhood of Shawneeland is nestled against the backdrop of Great North Mountain in western Frederick County, Virginia. Build a weekend getaway, or enjoy year-round living. Immerse yourself in nature as you witness a variety of birds, the occasional flock of wild turkeys, and deer foraging among the trees. This community offers a spring-fed lake where residents

  Rebecca McTavish Long & Foster Real Estate, Inc.

  0 Graywolf Trail, Winchester, VA 22602
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  /35

  Est $388,657 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,922 Sq Ft

  2627 Cornerstone Cir, Winchester, VA 22601

  2627 Cornerstone Cir, Winchester, VA 22601
• 

  

  /48

  $349,900

  • 5 Beds
  • 3.5 Baths
  • 2,440 Sq Ft

  119 Buffalo Trail, Winchester, VA 22602

  2020 built home sitting on a half acre of land in the lake community of Shawneeland!! Gleaming hardwood floors on the entire main and upper levels! Open Concept layout with a formal living room to your right as you enter. Spaious family room to your left as you enter with a large window letting in an abundance of natural light. The family room opens up into the combination kitchen/dining room

  Paul Sneeringer Keller Williams Realty

  119 Buffalo Trail, Winchester, VA 22602
• 

  /2

  $346,900 Sold Oct 14, 2025

  • 1,422 Sq Ft
  • $244/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  111 Comanche Trail, Winchester, VA 22602

  Well-built home in a quiet, private neighborhood on a 40,000 square foot lot. Split-level with a partially finished basement. Electric baseboard heat. Wooded area with small deck on rear.

  George Glaize George W. Glaize, Jr., Inc. REALTOR

  111 Comanche Trail, Winchester, VA 22602
• 

  

  /39

  Est $489,224 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,986 Sq Ft

  434 Crescent Dr, Winchester, VA 22601

  434 Crescent Dr, Winchester, VA 22601
• 

  

  /59

  $635,000

  • 4 Beds
  • 3.5 Baths
  • 4,632 Sq Ft

  930 Wayne Dr, Winchester, VA 22601

  Beautiful brick-front Colonial in a prime location! Nestled in a quiet neighborhood yet just minutes from I-81 and local amenities, this stunning home offers the perfect blend of convenience and tranquility.Step into the grand two-story foyer, flanked by a formal living room and dining room accented with elegant columns and a cozy fireplace. To the right, you’ll find a spectacular

  Elizabeth Flood Keller Williams Realty

  930 Wayne Dr, Winchester, VA 22601
• 

  

  /33

  $350,000 Sold Oct 14, 2025

  • 1,568 Sq Ft
  • $223/SF
  • 110 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  115 Mountain Lodge Dr, Winchester, VA 22602

  Welcome to your brand-new retreat in Mountain Falls! This thoughtfully designed three-story home offers the perfect mix of modern comfort and functional living. The main level features an open-concept layout with a spacious kitchen, dining area, family room, main-level laundry, and a convenient half bath—ideal for everyday ease and flow.Upstairs, you’ll find a generous private suite with

  Abby Walters Preslee Real Estate

  115 Mountain Lodge Dr, Winchester, VA 22602
• 

  

  /34

  Est $395,689 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,501 Sq Ft

  431 Crescent Dr, Winchester, VA 22601

  431 Crescent Dr, Winchester, VA 22601
• 

  

  /63

  $695,000

  • 5 Beds
  • 5 Baths
  • 5,398 Sq Ft

  112 Heath Ct, Winchester, VA 22602

  Nestled in the tranquil community of Twin Lakes Overlook, this stately home offers 5500 square feet of finished living space, with 5 bedrooms and 5 bathrooms. Walk up to the front door and enjoy the beauty of the professionally landscaped entryway. Open the front door and step into the grand 2 story foyer with a solid oak staircase. To the right of the foyer, walk through the doors to the first

  Dave Spence RE/MAX Roots

  112 Heath Ct, Winchester, VA 22602
• 

  

  /18

  $290,000 Sold Oct 14, 2025

  • 1,029 Sq Ft
  • $282/SF
  • 2 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  111 Dakota Trail, Winchester, VA 22602

  Welcome to 111 Dakota Trail nestled in the Shawneeland community! This charming 3-bedroom, 1-bath home offers the ease of one-level living and has been thoughtfully refreshed with modern updates while maintaining its rustic appeal. Recent renovations include a brand-new HVAC system, new windows, new roof, fresh paint, and nice deck to enjoy the outdoors.Step inside to a beautifully

  Mrs. Grace Bellows Samson Properties

  111 Dakota Trail, Winchester, VA 22602
• 

  

  /39

  Est $375,055 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,769 Sq Ft

  2642 Daniel Terrace, Winchester, VA 22601

  2642 Daniel Terrace, Winchester, VA 22601
• 

  

  /50

  $414,999

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft

  204 Ridge Rd, Winchester, VA 22602

  Well maintained brick Rancher(upgraded vinyl clad tilt windows,newer architectural roof) on a full basement on the east side of Winchester featuring over 2100 sqft of finished living space that offers true hardwood flooring on the main level with 3 bedrooms and 1 full bath. Spacious living room that features a gas log fireplace that has a woodstove insert included. Basement is 90% finished with a

  James Amick RE/MAX Roots

  204 Ridge Rd, Winchester, VA 22602
• 

  

  /43

  $559,900 Sold Oct 10, 2025

  • 2,614 Sq Ft
  • $214/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1987

  1729 Handley Ave, Winchester, VA 22601

  This immaculate 4-bedroom, 3-bath Cape Cod in sought-after Meadow Branch is move-in ready and full of thoughtful updates! From the welcoming foyer, the home flows seamlessly into a bright living room, spacious kitchen, and dedicated dining room. On the main level you'll also find two bedrooms and a full bath, perfect for guests or convenient one-level living.From the kitchen, step outside

  Jeanne Mezzatesta Colony Realty

  1729 Handley Ave, Winchester, VA 22601
• 

  

  /49

  Est $606,061 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,433 Sq Ft

  808 Lake Dr, Winchester, VA 22601

  808 Lake Dr, Winchester, VA 22601
• 

  

  /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
• 

  

  /25

  $232,000 Sold Oct 10, 2025

  • 720 Sq Ft
  • $322/SF
  • 74 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  132 Erie Trail, Winchester, VA 22602

  **Back on the market at no fault of the seller**This charming move-in ready home in the sought-after Shawneeland community offers the perfect blend of modern comfort and natural beauty. Featuring a newer roof, newer washer and dryer, updated lighting and fixtures, and a beautifully renovated bathroom and kitchen, this home has everything done for you. The primary bedroom currently holds a queen

  Ember Crow Pearson Smith Realty LLC

  132 Erie Trail, Winchester, VA 22602
• 

  

  /61

  Est $641,837 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,802 Sq Ft

  708 Lake Dr, Winchester, VA 22601

  708 Lake Dr, Winchester, VA 22601
• 

  

  /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
• 

  

  /42

  $324,500 Sold Oct 10, 2025

  • 1,178 Sq Ft
  • $275/SF
  • 141 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1930

  107 E Monmouth St, Winchester, VA 22601

  Price Reduction!! 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

  Jeanne Mezzatesta Colony Realty

  107 E Monmouth St, Winchester, VA 22601
• 

  

  /67

  Est $669,081 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,887 Sq Ft

  937 Kennedy Dr, Winchester, VA 22601

  937 Kennedy Dr, Winchester, VA 22601
• 

  

  /37

  $259,900

  • 3 Beds
  • 2 Baths
  • 931 Sq Ft

  309 Raccoon Dr, Winchester, VA 22602

  Move in ready 3 bedroom 2 full baths home nestled in the woods that comes with additional lots(2) that can be built on or kept as a privacy buffer and equates to an acre or so. House features hardwood flooring and lots of knotty pine for that rustic look. Living room features a wood burning fireplace that is capable of heating the entire house and there is plenty of free down wood on the lot

  James Amick RE/MAX Roots

  309 Raccoon Dr, Winchester, VA 22602
• 

  

  /39

  $320,000 Sold Oct 10, 2025

  • 2,369 Sq Ft
  • $135/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2007

  102 Elk Trail, Winchester, VA 22602

  Split Foyer with plenty of space and a heck of a view in the private community of Wilde Acres. From your breakfast room you will pan out to see the Shenandoah valley and your private backyard is set with a wooded backdrop. this 4 bedroom abode adopts the sense of open space along with traditional bedroom layout on the main floor with your entertaining room both off the kitchen and in the

  Dave Spence RE/MAX Roots

  102 Elk Trail, Winchester, VA 22602
• 

  

  /69

  Est $661,575 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,677 Sq Ft

  920 Kennedy Dr, Winchester, VA 22601

  920 Kennedy Dr, Winchester, VA 22601

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