Winchester County, VA Homes

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  /43

  $549,900 Open Sat 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 2,614 Sq Ft

  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

  (540) 698-5892

  1729 Handley Ave, Winchester, VA 22601
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  /11

  $1,700 per month

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

  44 S Loudoun St Unit 12, Winchester, VA 22601

  Discover the pinnacle of urban living in this charming 1-bedroom, 1-bathroom apartment located in the heart of the historic Winchester downtown walking mall. This comfortably spacious apartment merges the charm of its historic surroundings with the convenience of modern amenities, creating an exceptional rental choice. Perfectly positioned on the bustling Winchester walking mall, the apartment is

  

  Brock Harris

  Samson Properties

  (540) 584-1912

  44 S Loudoun St Unit 12, Winchester, VA 22601
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  /30

  $380,000 Sold Sep 04, 2025

  • 1,431 Sq Ft
  • $266/SF
  • 31 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2004

  1826 Kershaw Ln, Winchester, VA 22601

  This charming one-level home is perfectly situated in one of Winchester's desirable 55+ senior communities, Willow Lawn Cottages. Great home....first time on the market,featuring two spacious bedrooms, two full bathrooms, hardwood floors & vaulted ceilings. The open and inviting floor plan will make your new home ideal for both daily living and entertaining. The large primary suite offers

  Jeff Webber Long & Foster Real Estate, Inc.

  1826 Kershaw Ln, Winchester, VA 22601
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  /37

  Est $427,003 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
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  /9

  $225,000

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

  Lot 3 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

  (540) 974-1542

  Lot 3 Cedar Creek Grade, Winchester, VA
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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
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  /32

  $400,000 Sold Sep 02, 2025

  • 1,548 Sq Ft
  • $258/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  423 Crescent Dr, Winchester, VA 22601

  This charming one-level ranch is tucked away on a quiet cul-de-sac in the City of Winchester, just minutes from shopping, dining, and all the conveniences of town.Inside, updated hickory hardwood flooring flows throughout the home. The kitchen shines with updates, including new fixtures, quartzite countertops, and a fresh kitchen floor. The bathroom features an ADA-compliant shower, and

  Sharon Farinholt Realty ONE Group Old Towne

  423 Crescent Dr, Winchester, VA 22601
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  /20

  Est $445,348 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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  /99

  $869,500

  • 4 Beds
  • 4.5 Baths
  • 6,368 Sq Ft

  1517 Brookdale Ct, Winchester, VA 22601

  A rare opportunity to own the largest model in the Morlyn Hills neighborhood--more than 6500 square feet when including the fully finished basement. Situated on a premier lot and in immaculate, move-in-ready condition, this home is competitively priced and an exceptional value. This home features 4 bedrooms, 4.5 baths, and an impressive array of upgrades throughout.From the moment you enter

  

  Brock Harris

  Samson Properties

  (540) 596-5570

  1517 Brookdale Ct, 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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  /14

  $338,955 Sold Aug 29, 2025

  • 1,442 Sq Ft
  • $235/SF

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  629 Laurelwood Cir, Winchester, VA 22601

  Fall Move-In Poplar Available at Laurelwood Commons!This home features 3 bedrooms, 2.5 baths, 1,442 sq. ft., upgraded kitchen with white cabinets, quartz counters, island, LVP throughout the main level & more! Plus, enjoy all closing costs paid with use of NVR Mortgage!*. Learn more!

  Ryan Homes

  629 Laurelwood Cir, Winchester, VA 22601
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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
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  /53

  $633,000

  • 4 Beds
  • 3 Baths
  • 3,959 Sq Ft

  320 Linden Dr, Winchester, VA 22601

  *2-1 Buydown being offered. Contact Agent for Details!* Experience generational refined living in this stunning luxury home just minutes from Winchester Medical Center. Designed for both elegance and comfort, this residence boasts exquisite crown moldings, rich wood floors, wainscoting, and cathedral ceilings throughout. The main level offers one-level living with an entry-level bedroom, a

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-0212

  320 Linden Dr, Winchester, VA 22601
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  /74

  $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 areas 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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  /2

  $150,000 Sold Aug 29, 2025

  • 1,678 Sq Ft
  • $89/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1910

  315 National Ave, Winchester, VA 22601

  Colonial with separate lower and upper living units located blocks from downtown Winchester & the local library. Upper level is a 1 Bed/1 Bath with living room & kitchen and laundry hook-ups. Lower level is a 1 Bed/1 Bath with living room & kitchen and no laundry hook-ups.Property sold AS IS.Access from Jolley Lane and parking in rear of property.

  Sheila Pack RE/MAX Roots

  315 National Ave, Winchester, VA 22601
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  /17

  Est $281,035 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 734 Sq Ft

  228 Weems Ln, Winchester, VA 22601

  228 Weems Ln, Winchester, VA 22601
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  /50

  $749,000 Pending

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

  1205 Caroline St, Winchester, VA 22601

  **Do Not Miss This One!** Don’t miss this rare opportunity in the heart of Winchester! Offered for the first time since it was custom built in 2001, this stunning all-brick ranch sits on a beautifully landscaped and private 0.94-acre lot that feels like your own personal park complete with a stand of walnut trees. With nearly 3,000 square feet of thoughtfully designed space on the main level,

  

  Jim Shebest

  Coldwell Banker Realty

  (540) 802-5378

  1205 Caroline St, Winchester, VA 22601
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  /7

  $1,050 per month

  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  522 N Loudoun St Unit 6, 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 term. Utilities included, electric with $100/per month limit and tenant pays anything over that 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 6, Winchester, VA 22601
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  /45

  $410,000 Sold Aug 29, 2025

  • 2,250 Sq Ft
  • $182/SF
  • 3 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2018

  149 Biscane Ct, Winchester, VA 22602

  149 Biscane Ct, where fresh design feels effortlessly like home.. This beautifully maintained 2018 townhome shows like new construction! This spacious, light-filled townhome offers three levels of privacy and is ideal for today’s lifestyle. Let me walk you through your new home! When you pull into the garage, the front facing one-car garage features epoxy floors and wall shelving, ideal

  Kara Koonce Weichert, REALTORS

  149 Biscane Ct, Winchester, VA 22602
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  /36

  Not Listed For Sale

  • Studio
  • 3,790 Sq Ft

  912 S Braddock St, Winchester, VA 22601

  912 S Braddock St, Winchester, VA 22601
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  /2

  $279,000 Open Sat 10AM - 12PM

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  423 Highland Ave, Winchester, VA 22601

  Charming Winchester Home –Don't let this property slip away!This freshly updated home in the heart of Winchester offers incredible potential and versatility. Featuring off-street parking from the rear alley, a fresh coat of paint, and newly installed vinyl flooring downstairs, this property is move-in ready while leaving room for your personal touches.Highlights include:3

  

  Carlos Soares

  Samson Properties

  (540) 584-8746

  423 Highland Ave, Winchester, VA 22601
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  /73

  $2,099 - $2,733 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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  /20

  $219,000 Sold Aug 29, 2025

  • 496 Sq Ft
  • $442/SF
  • 62 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1927

  537 Hillman Dr, Winchester, VA 22601

  Update! Mandy is having more work done and will soon be connected to the city sewer system!! TIRED OF DATING? Hi, my name is Amanda. Some friends call me Mandy - and some call me 537 Hillman Drive. I have been working really hard on myself lately, and I think I’m ready for a long-term relationship. I started by covering the basics, like new Luxury Vinyl Plank flooring, ceiling fans, light

  Kristin Crosby Samson Properties

  537 Hillman Dr, Winchester, VA 22601
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  /49

  Est $413,968 Not Listed For Sale

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

  110 W Monmouth St, Winchester, VA 22601

  110 W Monmouth St, Winchester, VA 22601
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  /8

  $225,000 Under Contract

  • Land
  • 6 Acres
  • $40,761 per Acre

  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

  (540) 974-1542

  Lot 6 Cedar Creek Grade, Winchester, VA
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  /8

  $1,300 per month

  • 1 Bath
  • 1,100 Sq Ft
  • Condo for Rent

  4 W Cork St Unit 5, Winchester, VA 22601

  Welcome to Apartment 5 at 4 W Cork St., a rare opportunity to live in the heart of historic Old Town Winchester. This spacious studio residence offers a living space with one full bath, blending modern convenience with historic character in a beautifully preserved 1827 mixed-use building.Step inside and enjoy the open-concept layout, highlighted by refinished hardwood floors, exposed

  Patrick Slate Keller Williams Realty

  4 W Cork St Unit 5, Winchester, VA 22601
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  /44

  $420,000 Sold Aug 28, 2025

  • 1,324 Sq Ft
  • $317/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1945

  567 York Ave, Winchester, VA 22601

  Step into contemporary comfort with this top-to-bottom revamped gem in the heart of Winchester! A welcoming front porch invites you inside to discover sleek matte-black fixtures, new floors, and clean white finishes throughout. The open floor plan effortlessly blends the living room—anchored by a modern built-in fireplace—with a chef-ready kitchen boasting fresh cabinetry, lighting, and stainless

  Mike Webber EXP Realty, LLC

  567 York Ave, Winchester, VA 22601
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  /66

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  703 S Loudoun St, Winchester, VA 22601

  703 S Loudoun St, Winchester, VA 22601
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  /42

  $344,900

  • 3 Beds
  • 1.5 Baths
  • 1,178 Sq Ft

  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

  (540) 619-5037

  107 E Monmouth St, Winchester, VA 22601
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  /22

  $1,749 - $2,489 per month

  Meadow Branch Luxury Apartments

  1 - 3 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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  /13

  $190,000 Sold Aug 28, 2025

  • Land
  • 5 Acres
  • $35,185 per Acre

  • 34 Days On Market

  LOT B 4661 Middle Rd, Winchester, VA 22602

  Prime level 5.4- acre lot approved for a 4-bedroom standard septic system and well. Gently rolling and surrounded by nature, it the perfect canvas for your custom built-home. Don't miss this rare opportunity to own a piece of the country side just minutes from downtown Winchester. Call listing Agent to see property.

  Maureen Cunningham Century 21 Redwood Realty

  LOT B 4661 Middle Rd, Winchester, VA 22602
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  /2

  Est $298,793 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  127 S Euclid Ave, Winchester, VA 22601

  127 S Euclid Ave, Winchester, VA 22601
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  /2

  $399,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  Bedford II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

  Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Box bay rear window and 10' x 14' deck. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  

  DRB Homes

  Builder

  0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
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  /24

  $1,699 per month

  • 3 Beds
  • 1.5 Baths
  • 1,134 Sq Ft
  • Townhouse for Rent

  1111 Allen Dr Unit B, Winchester, VA 22601

  Beautiful 2 level Townhome, Concrete Driveway, Reasonable Rental price for 3 bedroom 1.5 baths , Completely Renovated, close to I-81 exit 315 Rt.7 , walking distance from shopping ctr and downtown 1 mile,HURRY UP, Call Lisa for showing arrangement.No Pets.No smoking.

  Ram Beladia First American Real Estate

  1111 Allen Dr Unit B, Winchester, VA 22601
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  /81

  $315,000 Sold Aug 27, 2025

  • 1,317 Sq Ft
  • $239/SF
  • 5 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1936

  709 N Braddock St, Winchester, VA 22601

  Welcome to this charming two-story in-town home offering 3 bedrooms, 2 baths, and an oversized yard with a true backyard oasis. A detached garage, wired for electric, provides ample space for parking, storage, or outdoor entertaining. The covered front porch offers a peaceful spot to sit, sip, and rejuvenate.Inside, the main level showcases a traditional layout with many restored original

  Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

  709 N Braddock St, Winchester, VA 22601
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  /19

  Est $439,568 Not Listed For Sale

  • 2 Beds
  • 4 Baths
  • 2,052 Sq Ft

  204 N Kent St, Winchester, VA 22601

  204 N Kent St, Winchester, VA 22601
• 

  

  /13

  $499,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,451 Sq Ft

  3131 Eton Place, Winchester, VA 22601

  End of Group, 4 Level Townhome with Deck and 4 ft. Rear Extension! Stunning Fully Upgraded Model Home – Don’t Miss Out! This gorgeous end of group model home at The Lofts at Creekside is a must-see! The Upton II features a gourmet kitchen with stainless steel appliances, quartz countertops, upgraded cabinets, and lighting. Oak staircases, a spacious fourth-level loft, and nine-foot ceilings add

  

  DRB Homes

  Builder

  3131 Eton Place, Winchester, VA 22601
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  /46

  $1,820 - $2,760 per month

  Stuart Hill

  1 - 3 Beds

  1981 Randolph Place, Winchester, VA 22601

  Nestled in the picturesque Shenandoah Valley in historic Winchester, Virginia, Stuart Hill Apartments combines convenience, a quality lifestyle, and warm, personalized service. Ideally situated just minutes from Historic Downtown Winchester, local shopping and dining, Shenandoah University, and the top-rated Winchester Medical Center, our community offers unparalleled access to everything you

  1981 Randolph Place, Winchester, VA 22601
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  /74

  $794,000 Sold Aug 27, 2025

  • 4,295 Sq Ft
  • $185/SF
  • 4 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2005

  1001 Armistead St, Winchester, VA 22601

  Spacious & Elegant 5-Bedroom Colonial in the Heart of Winchester!This beautifully maintained 5-bedroom, 4-bath Colonial offers over 4,000 sq. ft. of comfortable living in the City of Winchester. Hardwood flooring flows throughout the home, creating a warm and inviting atmosphere. The main level includes a convenient bedroom, a sunroom filled with natural light, and access to a large

  Sheila Pack RE/MAX Roots

  1001 Armistead St, Winchester, VA 22601
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  /37

  Not Listed For Sale

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

  216 E Piccadilly St, Winchester, VA 22601

  216 E Piccadilly St, Winchester, VA 22601

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