Winchester, VA Homes

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  /71

  $1,250,000

  • 7 Beds
  • 7 Baths
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! You have to see this $1M renovation by an architect out of NYC. Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an

  

  Lori Bales

  Keller Williams Realty

  (540) 660-3543

  202 S Washington St, Winchester, VA 22601
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• 

  

  

  /8

  $1,150 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  2259 Papermill Rd Unit 4, Winchester, VA 22601

  This lower level apartment is an end unit. 1 bedroom,1 bath apartment is in a great location close to shopping and restaurants. NO Smoking, NO pets, NO Vaping. $30 application fee to cover credit and background check. Landlord is looking for around 700 credit score.

  

  Frank Armstrong, IV

  Colony Realty

  (540) 701-4871

  2259 Papermill Rd Unit 4, Winchester, VA 22601
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  /43

  $630,000 Sold Jun 18, 2025

  • 1,940 Sq Ft
  • $325/SF
  • 40 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1920

  4661 Middle Rd, Winchester, VA 22602

  Don’t miss a rare opportunity to own this countryside farmette located justfive minutes from downtown Winchester. The completely renovatedfarmhouse shines on 5.9 picturesque acres with sweeping lawns, maturetrees and ample acreage for livestock, gardens and pets. When you stepinside this thoughtfully restored home, you are welcomed by light-filledspaces featuring all-new windows, doors, HVAC

  Maureen Cunningham Century 21 Redwood Realty

  4661 Middle Rd, Winchester, VA 22602
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  /37

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  222 E Piccadilly St, Winchester, VA 22601

  222 E Piccadilly St, Winchester, VA 22601
• 

  

  

  /71

  $1,250,000

  • Studio
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an additional 2 bedrooms, full bathroom and could laundry room that

  

  Lori Bales

  Keller Williams Realty

  (540) 917-5619

  202 S Washington St, Winchester, VA 22601
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  /12

  $2,400 per month

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  21 S Stewart St Unit 4, Winchester, VA 22601

  Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

  

  Frank Armstrong, IV

  Colony Realty

  (540) 781-1596

  21 S Stewart St Unit 4, Winchester, VA 22601
• 

  

  /40

  $475,000 Sold Jun 17, 2025

  • 2,376 Sq Ft
  • $200/SF
  • 6 Days On Market

  • 2 Beds
  • 3 Baths
  • Built 1989

  125 Premier Place, Winchester, VA 22602

  Welcome to 125 Premier Place! A beautifully maintained 2 Bedroom/3 Bathroom property located in a prime area of Winchester, VA and could easily be transformed back into a 4 bedroom home. With 2,376 square feet of flexible space and B-2 zoning, this unique opportunity is ideal for both residential or commercial use.Renovated in 2016, Major upgrades included a roof, vinyl siding, HVAC, water

  Erin Kavanagh EXP Realty, LLC

  125 Premier Place, Winchester, VA 22602
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  /14

  Not Listed For Sale

  0 Susquehanna Trail, Winchester, VA 22602

  0 Susquehanna Trail, Winchester, VA 22602
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  /83

  $649,900

  • 4 Beds
  • 3.5 Baths
  • 2,923 Sq Ft

  114 Nassau Dr, Winchester, VA 22602

  Discover Your Dream Home on Nassau Drive. Welcome to this stunning Colonial home, nestled on a beautifully landscaped, lot within the highly sought-after Fieldstone community. Conveniently located just off Route 7, this spacious property offers the perfect blend of commuter-friendly access and the privacy and tranquility of a large, fully fenced backyard. This impressive home features four

  

  Brock Harris

  Samson Properties

  (540) 781-1173

  114 Nassau Dr, Winchester, VA 22602
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  /13

  $1,700 - $2,400 per month

  The Local

  1-4 Beds

  230 Spring St, Winchester, VA 22601

  Modern designs, elegant finishes, and the most desirable amenities await you at the area’s newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

  230 Spring St, Winchester, VA 22601
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  /49

  $481,000 Sold Jun 17, 2025

  • 1,994 Sq Ft
  • $241/SF
  • 27 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1973

  562 Valley View Dr, Winchester, VA 22603

  A rare find in 22603! This property is nestled on a mostly wooded, 3 acre lot, offering a private setting. This is a one owner, one level, solid, brick home with a full walk-out basement. Cozy up to the fireplace or relax in the sunroom and take in the peacefulness and wildlife the forest brings. The main level has mostly hardwood floors, 3 bedrooms and 2 full bathrooms, sunroom and gas fireplace

  Cara Wilkins MarketPlace REALTY

  562 Valley View Dr, Winchester, VA 22603
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  /43

  Est $685,929 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,569 Sq Ft

  121 Wales Ct, Winchester, VA 22602

  121 Wales Ct, Winchester, VA 22602
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  /65

  $1,295,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,880 Sq Ft

  2277 Indian Hollow Rd, Winchester, VA 22603

  **An absolute Unicorn** This one of a kind property is like owning your own private State Park! This spectacular gated custom Brick and Cedar Ranch built in 2012 on 30 acres just outside Winchester was specifically designed as an off the grid family compound. The attention to detail is unmatched. It's endless list of unique features includes handmade bricks, custom Amish made kitchen cabinets

  

  Jim Shebest

  Coldwell Banker Realty

  (540) 917-5294

  2277 Indian Hollow Rd, Winchester, VA 22603
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  /15

  $1,150 per month

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

  116 N Indian Alley Unit 203, Winchester, VA 22601

  One bedroom apartment in the heart of Old Town Winchester. Stainless steel appliances in kitchen, gas stove, newly painted. Great location, walking distance to breweries, shops and dining. Forced air HVAC heat pump. Tenant pays electric and cable. Coin op Washer/Dryer for building adjacent to apartment. Landlord pays water, sewer, trash, gas and hot water. Secuirty deposit $1,150.

  Kim Hurst MarketPlace REALTY

  116 N Indian Alley Unit 203, Winchester, VA 22601
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  /26

  $235,000 Sold Jun 16, 2025

  • 1,173 Sq Ft
  • $200/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2003

  164 Brookland Ct Unit 10, Winchester, VA 22602

  Fantastic third floor condo available with no footsteps to be heard from above! The living room and dining area feature newer luxury vinal plank flooring, vaulted ceiling with skylights and a gas fireplace. Boasting two generously sized bedrooms and two full bathrooms this is a fantastic opportunity to own a piece of the east side of Winchester. Ideal commuter location near Route 7 and Interstate

  Stephanie Ryall Realty ONE Group Old Towne

  164 Brookland Ct Unit 10, Winchester, VA 22602
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  /20

  Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,160 Sq Ft

  206 N Kent St, Winchester, VA 22601

  206 N Kent St, Winchester, VA 22601
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  /9

  $450,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 3,190 Sq Ft

  102 Shockey Cir, Winchester, VA 22602

  What a fantastic opportunity for 1-level living in a very desirable neighborhood within 3 minutes to downtown Winchester. This beautiful, all-brick home is located in Fairway Estates, also adjacent to the Winchester Country Club and golf course. It’s been very well-maintained of the years - move in ready and also happy to receive your updated touches. The full, large basement offers a guest

  

  Lori Bales

  Keller Williams Realty

  (540) 215-8959

  102 Shockey Cir, Winchester, VA 22602
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  /22

  $1,749 - $2,231 per month

  Meadow Branch Luxury Apartments

  1-2 Beds

  424 Ridgewood Ln, Winchester, VA 22601

  Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We are conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

  424 Ridgewood Ln, Winchester, VA 22601
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  /68

  $825,000 Sold Jun 16, 2025

  • 4,242 Sq Ft
  • $194/SF
  • 49 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1975

  501 Princess Ct, Winchester, VA 22601

  It's all about spectacular mountain views! Built on one of the highest lots in Winchester by the area's premiere builder, Rhodes Brothers. Wake every morning to the fantastic views from the primary bedroom or enjoy your coffee while gazing at Great North Mountain. But this classic colonial home has a lot more to offer, including remodeled baths and kitchen, comfortable sunroom, five bedrooms, and

  John Schroth Colony Realty

  501 Princess Ct, Winchester, VA 22601
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  /30

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,442 Sq Ft

  4255 Middle Rd, Winchester, VA 22602

  4255 Middle Rd, Winchester, VA 22602
• 

  /2

  $695,000 Coming Soon

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

  1950 Melvor Ln, Winchester, VA 22601

  Coming Soon Offered to Investor - Currently Rented NO DRIVEBY SHOWINGS

  

  Kim Kroner

  Washington Dulles Real Estate Group

  (540) 453-8579

  1950 Melvor Ln, Winchester, VA 22601
• 

  

  /15

  $1,148 per month

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

  1816 Valley Ave Unit 1, Winchester, VA 22601

  Freshly Remodeled 1 BR Apartment available. Centered in the heart of Winchester, walking distance to shops, restaurants, and entertainment. Utilities and WIFI are included at no charge. No pets allowed. Come and enjoy all of what Winchester has to offer. On-site Laundromat, WIFI and Camera Monitoring.

  Raj Patel Ikon Realty - Ashburn

  1816 Valley Ave Unit 1, Winchester, VA 22601
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  /53

  $848,400 Sold Jun 16, 2025

  • 4,056 Sq Ft
  • $209/SF
  • 410 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2024

  279 Fishel Rd, Winchester, VA 22602

  10-7-24 Foundation Installed. Getting Ready to Frame! Impressive Home. Very private community (3 lots) can not be seen from road. Close to town with wooded lots setting off of main road with private lane (TO BE PAVED UPON COMPLETION OF HOMES). This home boosts two level living with 3,056 sq. ft. of floor plan with so many features others would call them upgrades! Brick front with cement siding

  Jim Thomson Realty ONE Group Old Towne

  279 Fishel Rd, Winchester, VA 22602
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  /43

  Est $634,907 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,729 Sq Ft

  405 Lynnehaven Dr, Winchester, VA 22602

  405 Lynnehaven Dr, Winchester, VA 22602
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  /32

  $349,900 Under Contract

  • Studio
  • 2,124 Sq Ft

  619 S Cameron St, Winchester, VA 22601

  **Attention Investors** Located on Historic Cameron Street just 5 blocks from from the Winchester Walking Mall with all of its restaurants, shops, and entertainment, this quaint 1930's home has been converted to two income producing apartments. Both apartments are currently leased on a month to month basis with tenants that would be interested in staying on. Each unit is one bedroom and one

  

  Jim Shebest

  Coldwell Banker Realty

  (540) 351-9661

  619 S Cameron St, Winchester, VA 22601
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  /50

  $1,785 - $3,144 per month

  The Lofts at Jubal Square

  1-3 Beds

  1864 Old Jube Square, Winchester, VA 22601

  Weve got it all at the Lofts at Jubal Square, the newest addition to the charming andhistoric Winchester cityscape. We offer a total commitment to better living, boasting largeapartments with loft and garage options, as well as amenities ideal for all those seeking anexceptional apartment lifestyle. Discover the Lofts at Jubal Square and discover what itmeans to live the good life.

  1864 Old Jube Square, Winchester, VA 22601
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  /40

  $600,000 Sold Jun 13, 2025

  • 2,531 Sq Ft
  • $237/SF
  • 1 Day On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  115 Oak Ridge Ln, Winchester, VA 22602

  Beautiful and move-in ready all-brick rancher featuring 3 large bedrooms, 2.5 baths, and 2,531 finished square feet, located just outside Winchester, VA in a well-desired community. Situated on a spacious lot, this home offers a cozy gas fireplace and generous room sizes throughout. The interior has been recently remodeled with luxury vinyl plank flooring, tile in the bathrooms and primary

  Amanda Magana RE/MAX Roots

  115 Oak Ridge Ln, Winchester, VA 22602
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  /6

  Not Listed For Sale

  • Studio
  • 1,710 Sq Ft

  13 E North Ave, Winchester, VA 22601

  13 E North Ave, Winchester, VA 22601
• 

  

  /43

  $500,000

  • 4 Beds
  • 3 Baths
  • 1,881 Sq Ft

  331 Ridge Ave, Winchester, VA 22601

  Assessed at $491K and only asking $500K. One level living on a beautiful corner lot in Whittier Acres - a very desirable neighborhood in Winchester City! Take advantage of the convenience of everything Winchester in this location - Winchester Medical Center, Downtown Winchester, the Museum of the Shenandoah Valley, and all of the popular restaurants. With 3 bedrooms and 2 bathrooms on the

  

  Lori Bales

  Keller Williams Realty

  (540) 253-4577

  331 Ridge Ave, Winchester, VA 22601
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  /15

  $1,976 per month

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • House for Rent

  106 Green Park Ct, Winchester, VA 22602

  Entire house with hardwood . Central HVAC. No carpet. Great Fenced yard with 2 sheds. 3 Bedrooms and 1 Bath Rancher. Great Commuter location close to Rt. 7/81/Sensury Road.

  Raj Patel Ikon Realty - Ashburn

  106 Green Park Ct, Winchester, VA 22602
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  /39

  $320,000 Sold Jun 13, 2025

  • 1,376 Sq Ft
  • $233/SF
  • 3 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1960

  2938 S Pleasant Valley Rd, Winchester, VA 22601

  Welcome to this well-maintained ranch-style home that offers comfort, character, and plenty of room to grow. Built in 1960, this charming 3-bedroom, 1.5-bath property features hardwood floors throughout and a spacious living room complete with a large picture window and a cozy fireplace. Thoughtful built-ins and a dedicated dining area add both charm and functionality.The kitchen is well-equipped

  Danielle Snapp Coldwell Banker Premier

  2938 S Pleasant Valley Rd, Winchester, VA 22601
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  /29

  Est $522,553 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,151 Sq Ft

  442 Canyon Rd, Winchester, VA 22602

  442 Canyon Rd, Winchester, VA 22602
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  /23

  $285,000

  • 3 Beds
  • 2 Baths

  332 Caldwell Ln, Winchester, VA 22602

  Here is your opportunity to own over 2.5 acres within minutes of Downtown Winchester. This property is located at the very end of a street with no cut through. The land is relatively flat and the septic system was recently inspected and fully repaired. This manufactured home is deeded as real estate and completely move-in ready. Neighboring properties also have large yards so there is plenty

  

  Lori Bales

  Keller Williams Realty

  (540) 274-5148

  332 Caldwell Ln, Winchester, VA 22602
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  /37

  $1,129 - $1,730 per month

  Fay Street Apartments

  1-3 Beds

  121 Fay St, Winchester, VA 22602

  NEW MANAGEMENT, NEW LOOK! Live on your own terms with Fay Street Apartments. Find thecomfort and convenience you crave among our one- and two-bedroom apartments, and three-bedroom townhomes, on our well-kept premises, and in the nearby, quaint town ofWinchester, VA. Our community opens doors to a myriad of opportunitieswill youreach out and seize them all?Start an exciting

  121 Fay St, Winchester, VA 22602
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  /26

  $270,000 Sold Jun 13, 2025

  • 990 Sq Ft
  • $273/SF
  • 3 Days On Market

  • 1 Bed
  • 1.5 Baths
  • Built 1900

  129 E Cork St, Winchester, VA 22601

  Location-Location-Location. This home offers a 1 bedroom Suite, Sitting Room, Walk-in Closet and Full Bath.Main Level: Offers Large Living Room with Built-in Book Shelves and TV Nook. Dining Room with Built-In China Closet. Kitchen offers Stainless Steel Appliances approximate 2 Years old. Gas Furnace/ Central A/C approximately 2 years old. Covered front porch. Rear yard offers Two stone

  George Johnson Jim Barb Realty Inc.

  129 E Cork St, Winchester, VA 22601
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  /60

  Est $410,291 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft

  152 Solara Dr, Winchester, VA 22602

  152 Solara Dr, Winchester, VA 22602
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  /45

  $515,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,466 Sq Ft

  106 Poe Dr, Winchester, VA 22602

  Welcome to This Lovely Richmond American Homes, Pearl Model. A Beautiful Single Family Home Located On An Oversized Corner Lot. 4 Bedroom, 3 Full Bathrooms. Gourmet Kitchen Boasts Quartz Counters, Stainless Steel Appliances, A Grand Island For Quick Bites, And An Spacious, Open Concept Main Level. This Home Offers A Main Level Bedroom With A Full Bathroom and An Upstairs Bonus Room/ Loft. Raven

  

  Adrian Blakeney

  EXP Realty, LLC

  (540) 805-8133

  106 Poe Dr, Winchester, VA 22602
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  /28

  $1,850 per month

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Townhouse for Rent

  331 E Piccadilly St, Winchester, VA 22601

  Super charming 1930's 3 bedroom 1 bathroom duplex just blocks from Old Town Winchester! This unit has been recently remodeled with an updated bathroom, carpet and light fixtures. You'll find the original wood floors, a large front porch, a fenced in backyard and spacious garage. Pets allowed on a case by case basis, tenant pays all utilities, washer and dryer in basement, updated heating and

  Holly Graham Realty ONE Group Old Towne

  331 E Piccadilly St, Winchester, VA 22601
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  /51

  $415,000 Sold Jun 13, 2025

  • 1,409 Sq Ft
  • $295/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2015

  315 E Piccadilly St, Winchester, VA 22601

  2015 home nestled in with vintage properties in one of Old Town's up and coming areas...convenient and walkable to restaurants, music venues, boutique shops and the Handley Library!! Open main floor plan, with 9 foot ceilings... very bright and airy. Enjoy remodeled kitchen which includes quartz countertops, white cabinets and stainless steel appliances, plus so much more. Whole house plantation

  Stuart Wolk ERA Oakcrest Realty, Inc.

  315 E Piccadilly St, Winchester, VA 22601
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  /27

  Est $368,612 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  427 Washout Ln, Winchester, VA 22603

  427 Washout Ln, Winchester, VA 22603

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