Winchester, VA Homes

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  /14

  $225,000

  • Land
  • 15 Acres
  • $15,000 per Acre

  0 N Frederick Pike Unit VAFV2038096, Winchester, VA 22603

  Just 7 miles/minutes from Winchester Medical Center and 10 miles from downtown Winchester, this 15-acre parcel offers privacy and convenience in one. The land features rolling hills, unlogged mature hardwood forest, and mountain views, with a gravel driveway crossing a private bridge into a secluded, untouched setting. Zoned residential, agricultural, and potentially commercial, it’s ideal for

  Kristina Towns Weichert Realtors - Blue Ribbon

  0 N Frederick Pike Unit VAFV2038096, Winchester, VA 22603
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  /24

  $1,700 per month

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft
  • Townhouse for Rent

  235 1/2 Millwood Ave, Winchester, VA 22601

  Beautiful apt right in Old Town - grab your coffee across the street each morning, and relax on your patio each evening! This 2 bedroom 1.5 bath duplex is well cared for, with a welcoming front porch that leads into the open living room and kitchen with bar seating area. The kitchen is fully stocked with stainless appliances and tons of cabinetry and counter space. There is even storage space

  Misty Weaver Samson Properties

  235 1/2 Millwood Ave, Winchester, VA 22601
• 

  

  

  /34

  $289,000 Sold Oct 28, 2025

  • 1,186 Sq Ft
  • $244/SF
  • 111 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  711 E Cork St, Winchester, VA 22601

  Welcome home to 711 E. Cork Street! Centrally located in Winchester, VA. This is a wonderful home for first time buyer, someone looking to downsize and would make a great single family rental for your portfolio. Enjoy the ease of access to downtown Winchester, Jim Barnett Park, Shenandoah University, shopping, and commuter routes. This 2 bedroom 1 1/2 bath detached home with brand new exterior

  Jim Stafford ERA Oakcrest Realty, Inc.

  711 E Cork St, Winchester, VA 22601
• 

  

  

  /21

  Est $346,188 Not Listed For Sale

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

  2915 S Pleasant Valley Rd, Winchester, VA 22601

  2915 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  

  /51

  $1,115,000

  • 7 Beds
  • 4.5 Baths
  • 4,180 Sq Ft

  207 Westview Dr, Winchester, VA 22603

  Welcome to 207 Westview Drive, a secluded sanctuary nestled on just over six wooded acres in the heart of the Shenandoah Valley—mere minutes from the charm of Historic Old Town Winchester. With over 6,300 square feet of beautifully finished living space, this one-of-a-kind property offers the perfect blend of luxury, comfort, and natural beauty. Tucked deep into the trees, yet close to shops,

  Carolyn Young Samson Properties

  207 Westview Dr, Winchester, VA 22603
• 

  

  /17

  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • House for Rent

  347 Shenandoah Ave, Winchester, VA 22601

  Recently completely updated. Great condition, requires first lease 18 months, additional leases will be 12 month terms.Owner licensed Real Estate Broker in State of VA.

  Jeff Webber Long & Foster Real Estate, Inc.

  347 Shenandoah Ave, Winchester, VA 22601
• 

  

  /46

  $430,000 Sold Oct 27, 2025

  • 1,714 Sq Ft
  • $251/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1978

  301 Yale Dr, Winchester, VA 22602

  Situated on a lovely corner lot with thoughtful landscaping, lovely trees, and a circular driveway providing ample parking, this move-in-ready home offers both charm and functionality. Inside, the main level features a cozy family room with wood stove, a spacious living room with fireplace, and an updated kitchen with eat-in area. From the kitchen, step into the enclosed sun porch, complete with

  Bradley Comstock ERA Oakcrest Realty, Inc.

  301 Yale Dr, Winchester, VA 22602
• 

  

  /23

  Est $271,550 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,252 Sq Ft

  2905 Sorrell Ct, Winchester, VA 22601

  2905 Sorrell Ct, Winchester, VA 22601
• 

  

  /40

  $315,000

  • 2 Beds
  • 1.5 Baths
  • 1,214 Sq Ft

  305 Sutton Ct, Winchester, VA 22601

  Whether you are looking for the perfect Investment Property or Your New Home...This Move-in-Ready Home feels Like-New and it's just what you've been waiting for! Offering a beautifully updated Townhouse in sought-after Huntington Meadows, located just off Berryville Ave & minutes from Rt7, close to shopping, dining and all the amenities you need! Great Location! This townhouse is one of the

  Nancy Shiley Samson Properties

  305 Sutton Ct, Winchester, VA 22601
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  /34

  $3,500 per month

  • 6 Beds
  • 4.5 Baths
  • 3,331 Sq Ft
  • House for Rent

  117 Manasquan Way, Winchester, VA 22602

  Welcome to Your Dream Rental – Brand New 6-Bedroom Home! Be the first to live in this stunning new construction single-family home, designed with modern living in mind. With 6 spacious bedrooms, 4 full bathrooms, a main floor office, and a fully finished walkout basement, this home offers the perfect blend of comfort, flexibility, and style. Bright, open-concept layout with abundant natural

  Thambi Gangadhar Gaja Associates Inc.

  117 Manasquan Way, Winchester, VA 22602
• 

  

  /22

  $265,000 Sold Oct 27, 2025

  • 1,332 Sq Ft
  • $199/SF
  • 18 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2001

  2949 Sorrell Ct, Winchester, VA 22601

  Charming Townhouse in Winchester City Limits Welcome to this well-maintained townhouse offering three spacious bedrooms and one and a half baths, perfectly located within the desirable Winchester city limits. This interior unit boasts a spacious living room, ideal for both relaxation and entertaining. The primary bedroom is particularly noteworthy, featuring generous space and a walk-in closet

  Shanon Levi RE/MAX Roots

  2949 Sorrell Ct, Winchester, VA 22601
• 

  

  /38

  Est $269,712 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2945 Sorrell Ct, Winchester, VA 22601

  2945 Sorrell Ct, Winchester, VA 22601
• 

  

  /3

  $3,200,000

  • Land
  • 8.65 Acres
  • $369,942 per Acre

  0 0 Northwestern Pike, Winchester, VA 22602

  Prime opportunity on 13.05 acres in an unbeatable high-visibility location along Route 50 in Winchester, VA. Positioned directly across from major retailers and conveniences—including Walmart, Sheetz, Tractor Supply, Applebee’s, Dunkin’, Bojangles, and the Winchester Medical Center campus—this property offers exceptional exposure and accessibility. Zoned for multiple development possibilities,

  Sarah Reynolds Keller Williams Realty

  0 0 Northwestern Pike, Winchester, VA 22602
• 

  

  /13

  $1,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,752 Sq Ft
  • Townhouse for Rent

  1970 Cidermill Ln, Winchester, VA 22601

  Welcome to 1970 Cidermill in the Orchard Hill subdivision of Winchester! This updated two-story townhome offers three bedrooms, 2.5 bathrooms, and a recently updated kitchen and bathrooms. The main level features an open living and dining area with a cozy gas fireplace, while the upper level includes a primary suite with a private bathroom, two additional bedrooms, and laundry facilities. Enjoy a

  Marisa Varley ERA Oakcrest Realty, Inc.

  1970 Cidermill Ln, Winchester, VA 22601
• 

  

  /18

  $444,990 Sold Oct 24, 2025

  • 1,657 Sq Ft
  • $269/SF

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  216 Munsee Cir, Winchester, VA 22602

  The Cabral offers 1,657 square feet of thoughtfully designed living space, featuring 3 spacious bedrooms, 2.5 bathrooms, and a versatile loft on the bedroom level—perfect for a home office, playroom, or additional lounge area. This home features a beautiful cypress green exterior with stone accents, and inside, you’ll find stylish white kitchen and bathroom cabinets paired with modern finishes

  D.R. Horton

  216 Munsee Cir, Winchester, VA 22602
• 

  

  /18

  Est $279,253 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2947 Sorrell Ct, Winchester, VA 22601

  2947 Sorrell Ct, Winchester, VA 22601
• 

  

  /26

  $299,990

  • 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
• 

  

  /23

  $1,775 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  321 N Braddock St, Winchester, VA 22601

  Gorgeously remodeled 2 Bedroom 1 Bath two-story apartment located in Charming Historic Downtown Winchester. This apartment has been freshly painted and updated with Brand New Appliances to include Refrigerator, stove, rangehood, washer and dryer. Additional updates include new kitchen sink, countertops, light fixtures, blinds, and ceramic tub surround. Light and Bright this apartment has two

  Angela Duncan MarketPlace REALTY

  321 N Braddock St, Winchester, VA 22601
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  /28

  $580,000 Sold Oct 24, 2025

  • 7,650 Sq Ft
  • $76/SF
  • 284 Days On Market

  • Built 1891

  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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  /30

  Est $284,309 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2955 Sorrell Ct, Winchester, VA 22601

  2955 Sorrell Ct, Winchester, VA 22601
• 

  

  /21

  $80,000

  • Land
  • 1 Acre
  • $80,000 per Acre

  852 Cedar Grove Rd, Winchester, VA 22603

  NEW LISTING Wooded 1 Acre lot on Cedar Grove Rd. Winchester, VA. Mature hardwoods on a gently sloping lot. Well is located on the front of the parcel, with no known septic letter. Old travel trailer on the lot.

  Wendy Conner Coldwell Banker Premier

  852 Cedar Grove Rd, Winchester, VA 22603
• 

  

  /22

  $1,499 per month

  • 2 Beds
  • 1.5 Baths
  • 1,148 Sq Ft
  • Townhouse for Rent

  1016 Franklin St Unit 2, Winchester, VA 22601

  Renovated Beautiful 2 level Townhome, Renovated/Reasonable Rental price , Completely Renovated, close to I-81 exit 315 Rt.7 , walking distance from shopping ctr and downtown 1 mile,HURRY UP, Minimum combined occupants Income 54k/year required, clear background.

  Ram Beladia First American Real Estate

  1016 Franklin St Unit 2, Winchester, VA 22601
• 

  

  /65

  $435,000 Sold Oct 24, 2025

  • 1,919 Sq Ft
  • $227/SF
  • 6 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2002

  101 Calico Ct, Winchester, VA 22602

  Welcome to this former model home in the sought-after 55+ community of Cross Creek Village! Sitting on a premium corner lot, this 2-bedroom, 2-bath beauty offers just over 1,900 sq. ft. of comfortable main-level living. You’ll love the open layout with luxury vinyl plank flooring throughout, a cozy gas fireplace in the living/dining area, and a spacious primary suite with an oversized bath,

  Jeanne Mezzatesta Colony Realty

  101 Calico Ct, Winchester, VA 22602
• 

  

  /10

  Est $282,936 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2963 Sorrell Ct, Winchester, VA 22601

  2963 Sorrell Ct, Winchester, VA 22601
• 

  

  /44

  $374,900

  • 4 Beds
  • 3 Baths
  • 1,840 Sq Ft

  166 Graywolf Trail, Winchester, VA 22602

  Welcome to 166 Graywolf Trail, a stunningly renovated 4-bedroom, 3-bath home nestled on nearly a half acre of peaceful woodland in beautiful Winchester, VA. This move-in ready retreat blends modern comfort with a cozy family feel — the kind of home where memories are made. Step inside and discover an entirely new interior from top to bottom. Every inch has been thoughtfully updated: brand-new

  Mike Webber EXP Realty, LLC

  166 Graywolf Trail, Winchester, VA 22602
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  /8

  $1,100 per month

  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  522 N Loudoun St Unit 1, Winchester, VA 22601

  Furnished efficiency ready for occupancy in downtown historic Winchester VA. Just a few blocks away from the downtown walking mall. 3 month minimum lease terms. Utilities included, electric with $100/per month limit and tenant pays anything over the amount. Coin op washer/dryer and off street parking. No animals, no smoking. VAR or NVAR rental application with $50/per person application fee paid

  Mandie Gladwell OliveTree Property Group, LLC

  522 N Loudoun St Unit 1, Winchester, VA 22601
• 

  

  /50

  $339,000 Sold Oct 24, 2025

  • 1,288 Sq Ft
  • $263/SF
  • 39 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  416 Bluebird Trail, Winchester, VA 22602

  Just Listed – Beautifully Remodeled 3 Bedroom, 2 Bath Rambler! Step into comfort and style with this newly remodeled rambler featuring 3 spacious bedrooms and 2 modern bathrooms. Every inch of this home has been updated – including brand-new appliances, luxury flooring throughout, and fresh finishes that make it move-in ready. Enjoy peaceful wooded views from your private back deck, perfect for

  Lisa Blansett Mountains Edge Realty LLC

  416 Bluebird Trail, Winchester, VA 22602
• 

  

  /27

  Est $286,281 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2967 Sorrell Ct, Winchester, VA 22601

  2967 Sorrell Ct, Winchester, VA 22601
• 

  

  /19

  $325,000

  • 4 Beds
  • 1.5 Baths
  • 1,659 Sq Ft

  728 Green St, Winchester, VA 22601

  This spacious rancher is ideal for someone looking to add their personal touch on a home! With some updates needed, the canvas is ready for you to add some fresh paint and new flooring to bring new life into this home! It does feature a charming brick fireplace, oversized living room, formal dining area, and spacious bedrooms. You'll also notice upgrades to the kitchen along with a newer roof.

  Gavin Washington Weichert Realtors - Blue Ribbon

  728 Green St, Winchester, VA 22601
• 

  

  /9

  $1,100 per month

  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  522 N Loudoun St Unit 2, Winchester, VA 22601

  Furnished efficiency ready for occupancy in downtown historic Winchester VA. Just a few blocks away from the downtown walking mall. 3 month minimum lease terms. Utilities included, electric with $100/per month limit and tenant pays anything over the amount. Coin op washer/dryer and off street parking. No animals, no smoking. VAR or NVAR rental application with $50/per person application fee paid

  Mandie Gladwell OliveTree Property Group, LLC

  522 N Loudoun St Unit 2, Winchester, VA 22601
• 

  

  /96

  $1,200,000 Sold Oct 24, 2025

  • 4,994 Sq Ft
  • $240/SF
  • 22 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2006

  291 Lake Serene Dr, Winchester, VA 22603

  This captivating property on Lake Serene offers a truly grand living experience— a private oasis meticulously crafted for your enjoyment. Four artfully created levels. Almost 5,000 square feet. Gorgeous waterfront views flanked by lush woods. And the backyard of your dreams. The handsome stone façade with brick features hints at the architectural details that continue inside with an arched brick

  Dan Whitacre Colony Realty

  291 Lake Serene Dr, Winchester, VA 22603
• 

  

  /16

  Est $291,954 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  2975 Sorrell Ct, Winchester, VA 22601

  2975 Sorrell Ct, Winchester, VA 22601
• 

  

  /50

  $350,000

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

  163 Denny Ln, Winchester, VA 22603

  Open House, Sunday, November 23rd 11:00am - 1:00pm. Excellent outdoor workspace and storage on the east side of Winchester. NO HOA - This property offers a detached two-car carport, a wired shed/workshop, and a wrap-around paved driveway, providing ideal space for vehicles, tools, hobbies, and additional parking. Inside, this one-level ranch home features several recent updates, including new

  Robin Gebhardt EXP Realty, LLC

  163 Denny Ln, Winchester, VA 22603
• 

  

  /27

  $2,100 per month

  • 3 Beds
  • 2.5 Baths
  • 1,442 Sq Ft
  • Townhouse for Rent

  623 Laurelwood Cir, Winchester, VA 22601

  Experience the best of contemporary living in the new Laurelwood Commons community, a serene enclave of just 34 newly constructed townhomes in the heart of Winchester. This community is designed for convenience and a tranquil lifestyle, with townhomes situated on a single, U-shaped street, creating a cozy and private feel. This new construction townhouse, completed in 2025, offers the perfect

  Jody Elson Dream Real Estate

  623 Laurelwood Cir, Winchester, VA 22601
• 

  

  /10

  $189,900 Sold Oct 24, 2025

  • 917 Sq Ft
  • $207/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1956

  11 S Euclid Ave, Winchester, VA 22601

  Priced To Sell Fast! Renovate & Resell, Buy & Hold, or Move-In and Build Some Sweat Equity. Desirable Brick Rambler, Spacious Kitchen, Spacious Bedrooms, Hardwood Floors, .25 Acre Lot, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sold As-Is.

  Matthew Altizer ANR Realty, LLC

  11 S Euclid Ave, Winchester, VA 22601
• 

  

  /23

  Est $289,522 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,280 Sq Ft

  2950 Sorrell Ct, Winchester, VA 22601

  2950 Sorrell Ct, Winchester, VA 22601
• 

  

  /42

  $849,990

  • 5 Beds
  • 4.5 Baths
  • 5,254 Sq Ft

  1504 Brookdale Ct, Winchester, VA 22601

  This home generates income from solar energy sales averaging over $2k a year! The Solar panels and system are OWNED by the homeowner NOT leased. There are no monthly fees or payments for the system. System is “Grandfathered” with a licensing agreement that allows homeowner to sell excess electricity produced. Lower your energy costs and receive cash earnings! Recent updates over $40k in this

  Julie Shiley Coldwell Banker Realty

  1504 Brookdale Ct, Winchester, VA 22601
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  /26

  $1,850 per month

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • House for Rent

  105 E Pall Mall St, Winchester, VA 22601

  SO AFFORDABLE! Spacious 3-bedroom house with 2 full baths, wood floors, fenced back yard. Near historic Old Town Winchester, Shenandoah University, shopping, services, museums and commuter routes 50, 7 and I-81. Laundry room with washer and dryer. Main-level bath has shower. Upstairs bath has tub. Eat-in kitchen with pantry. Kitchen appliances, washer and dryer included. 13 X 7 walk-in closet and

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  105 E Pall Mall St, Winchester, VA 22601
• 

  

  /71

  $400,000 Sold Oct 24, 2025

  • 1,721 Sq Ft
  • $232/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1931

  1576 Old Bethel Church Rd, Winchester, VA 22603

  Step back in time with this 1931 farmhouse set on 5 acres, blending historic character with thoughtful modern updates—all just minutes from Winchester. This property offers convenient access to main roads while maintaining the space and feel of country living.The home features 3 bedrooms, 2 updated baths, hardwood floors, and an oversized two-car garage with workshop space. Recent

  Natasha Roberts Realty ONE Group Old Towne

  1576 Old Bethel Church Rd, Winchester, VA 22603
• 

  

  /13

  Est $240,676 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,116 Sq Ft

  422 Cornwallis Ct, Winchester, VA 22601

  422 Cornwallis Ct, Winchester, VA 22601

Showing Results 401 - 440, Page 11 of 18