Winchester, VA Homes

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  /71

  $1,250,000 Under Contract

  • 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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  /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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  /33

  $390,000 Sold Aug 08, 2025

  • 1,930 Sq Ft
  • $202/SF
  • 14 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2003

  658 Sherlock Trace, Winchester, VA 22601

  Welcome to 658 Sherlock Trace in Winchester, VA – a spacious and energy-efficient home with no HOA! Conveniently located near the intersection of Routes 11, 37, 7, and I-81, this property offers easy access for commuting, shopping, and daily essentials.This well-maintained residence features 5 generously sized bedrooms and 3 full bathrooms, perfect for families or guests. The thoughtfully

  Elcy Pereira Elcy & Co. Realty, LLC.

  658 Sherlock Trace, Winchester, VA 22601
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  /43

  Est $434,835 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft

  512 Lanny Dr, Winchester, VA 22601

  512 Lanny Dr, Winchester, VA 22601
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  /46

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 2,859 Sq Ft

  247 Mcguire Rd, Winchester, VA 22603

  Tucked away on a private 2.7-acre wooded lot, this stunning all-brick colonial has been fully renovated from top to bottom. Inside, 3/4" solid ash, 5"wide herringbone flooring flows throughout, accented by designer lighting, crown molding, and elegant chair rail trim. The chef’s kitchen is a true showstopper—featuring a massive island, striking white and gold appliances, and custom finishes. The

  

  Lori Bales

  Keller Williams Realty

  (540) 701-5541

  247 Mcguire Rd, Winchester, VA 22603
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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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  /40

  $380,000 Sold Aug 08, 2025

  • 1,584 Sq Ft
  • $240/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 2000

  115 Tanglewood Ln, Winchester, VA 22602

  Welcome to 115 Tanglewood Lane - Located on a quiet, no-through street in one of Winchester’s incredible 55+ communities, this charming home offers the perfect blend of comfort, convenience, and low-maintenance living. Just minutes from historic downtown Winchester and walking distance to Creekside Station, you'll love having shops, restaurants, and local businesses right at your

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  115 Tanglewood Ln, Winchester, VA 22602
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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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  /46

  $415,000

  • 3 Beds
  • 3 Baths
  • 1,806 Sq Ft

  133 Woodrow Rd, Winchester, VA 22602

  Welcome home to this charming split foyer in Carlisle Heights, ideally located on the east side of Winchester—just off Route 7 for an easy commute!Step inside to a light-filled interior featuring low-maintenance flooring throughout the main living areas and bedrooms, offering both comfort and practicality. The spacious, updated kitchen showcases white cabinetry, stainless steel

  

  Angie Ordonez

  NextHome Realty Select

  (540) 384-4063

  133 Woodrow Rd, Winchester, VA 22602
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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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  /89

  $595,000 Sold Aug 08, 2025

  • 3,086 Sq Ft
  • $193/SF
  • 103 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2005

  121 Carnmore Dr, Winchester, VA 22602

  Set on a quiet street in an established neighborhood is this lovely traditional home. Experience peace and tranquility on this large cul-de-sac lot. Front, side and back yards are large offering .28 private acres. Start the day with coffee on the wraparound porch and celebrate summer evenings by dining on the expansive Trex Deck. Community sidewalks and street-lights offer more enjoyment for

  Angela Duncan MarketPlace REALTY

  121 Carnmore Dr, Winchester, VA 22602
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  /14

  Not Listed For Sale

  0 Susquehanna Trail, Winchester, VA 22602

  0 Susquehanna Trail, Winchester, VA 22602
• 

  

  /39

  $450,000 Under Contract

  • 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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  /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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  /43

  $275,000 Sold Aug 07, 2025

  • 1,288 Sq Ft
  • $214/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2001

  1000 Hickory Trail, Winchester, VA 22602

  Hickory Trail... WHAT A FIND!!! This home shows nicely and simply needs a little TLC, whether an investor, a DIY Enthusiast, or whatever your goals may be, this home has so many possibilities without a ton of work, so much so, there's simply not enough space to list them all! Inside you'll find spacious living, high ceilings in the living room and dine in kitchen, sizeable bedrooms and lovely

  Nicole Lewis Coldwell Banker Premier

  1000 Hickory Trail, Winchester, VA 22602
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  /43

  Est $693,455 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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  /45

  $475,000 Under Contract

  • 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 Housing the Farmhouse sink and quiet Dishwasher. An Spacious, Open Concept Main Level Featuring An Electric Fireplace. This Home Offers A Main Level Bedroom

  

  Adrian Blakeney

  EXP Realty, LLC

  (540) 805-8133

  106 Poe Dr, Winchester, VA 22602
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  /31

  $2,100 per month

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

  290 Sage Cir, Winchester, VA 22603

  **PLEASE SEE DOCUMENTS FOR RENTAL APPLICATION INSTRUCTIONS**

  Rachel Olsen Keller Williams Realty

  290 Sage Cir, Winchester, VA 22603
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  /67

  $620,000 Sold Aug 07, 2025

  • 2,760 Sq Ft
  • $225/SF
  • 19 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2002

  162 Darby Dr, Winchester, VA 22602

  Nestled in the sought-after Ravenwing community, this stunning colonial home offers a perfect blend of comfort and style. Built in 2002, this well-maintained residence boasts nearly 3,000 finished square feet of thoughtfully designed living space, ideal for creating lasting memories. Step inside to discover a warm and inviting atmosphere, highlighted by a fully finished basement that provides

  Michael Elias Century 21 Redwood Realty

  162 Darby Dr, Winchester, VA 22602
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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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  /51

  $699,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  881 Adams Rd, Winchester, VA 22603

  *Price Adjustment on this beautiful property!*Welcome to this exquisite 3-bedroom, 2-bath rancher nestled on nearly 9 private acres, offering 2,250 square feet of refined living space and unmatched serenity. From the moment you enter, you'll be captivated by the elegance of rich wood floors, 9-foot ceilings, and exquisite crown molding with wide baseboards throughout. The great room is a true

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 402-9684

  881 Adams Rd, Winchester, VA 22603
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  /22

  $1,799 - $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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  /36

  $375,000 Sold Aug 07, 2025

  • 1,800 Sq Ft
  • $208/SF
  • 4 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1900

  511 S Kent St, Winchester, VA 22601

  Live in downtown in this recently renovated turn of the century charmer. A short walk to the historic walking mall with all of its activities and amenities. Enjoy the original high main floor ceilings, spacious living/family room, open floor plan with the original staircase. The 2022 renovations included all new kitchen with closet pantry, bathrooms, electrical, HVAC (and service ducts),

  Lawrence Lessin Homes By Owner, Inc.

  511 S Kent St, 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
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  /21

  $156,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,093 Sq Ft

  154 Ashton Dr, Winchester, VA 22603

  NOTE: THIS PROPERTY IS UNAVAILABLE TO SEE BEFORE THE AUCTION. THE HIGH BIDDER WILL BE ALLOWED A HOME INSPECTION CONTINGENCY AND INSPECTION OF THE PROPERTY WITH RIGHT TO VOID THE CONTRACT IF NOT SATISFIED.****See Documents for Purchase Contract and Disclosure Documents****This Winchester home is one of a portfolio of 12 investment properties being sold at auction online ending on

  Alex Sharp

  Thornton River. LLC

  (540) 660-7206

  154 Ashton Dr, Winchester, VA 22603
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  /7

  $1,750 per month

  • 3 Beds
  • 3 Baths
  • 2,224 Sq Ft
  • House for Rent

  201 Cochise Trail, Winchester, VA 22602

  3 Bed/3 Bath log rancher with a finished basement apporximately six miles from Winchester Medical Center and downtown Winchester. Over 2,200 sq ft of living space! Spacious yard & driveway. Enjoy Cherokee Lake where residents can enjoy amenities like Cherokee Beach, playgrounds, and a 4-hole golf course in addition to the lake activities. Rent Spree application link attached to listing. **670+

  Sheila Pack RE/MAX Roots

  201 Cochise Trail, Winchester, VA 22602
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  /14

  $460,000 Sold Aug 07, 2025

  • 2,974 Sq Ft
  • $155/SF
  • 10 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1995

  2620 Stonegate Dr, Winchester, VA 22601

  Contemporary 5-Bedroom Rancher - Prime Winchester LocationDiscover one of Winchester's most coveted addresses – where urban convenience meets serene privacy in this meticulously maintained contemporary rancher. This exceptional 5-bedroom, 3-full-bath home sits on a premium lot backing to Frederick Douglass Elementary School and beautiful parkland, offering privacy with breathtaking sunrise

  Anthony Adamovich Key Move Properties, LLC.

  2620 Stonegate Dr, Winchester, VA 22601
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  /43

  Est $632,902 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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  /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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  /73

  $1,902 - $2,580 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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  /34

  $585,000 Sold Aug 07, 2025

  • 2,571 Sq Ft
  • $228/SF
  • 53 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2006

  720 Beehive Way, Winchester, VA 22601

  Welcome to Your Dream Home!Step into this beautifully updated 4-bedroom, 3.5-bath Colonial, ideally situated in one of the most sought-after neighborhoods off Cedar Creek Grade. With spacious living areas, thoughtful updates, and timeless charm, this home offers the perfect blend of comfort and style.At the heart of the home is a stunning open-concept kitchen, complete with brand-new

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  720 Beehive Way, 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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  /50

  $749,000 Open Sun 1PM - 4PM

  • 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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  /24

  $2,250 per month

  • 3 Beds
  • 2.5 Baths
  • Townhouse for Rent

  119 Nootka Way, Winchester, VA 22602

  Welcome to your brand-new rental home, at the Retreat at Winding Creek. This spacious 2-story townhome offers 1,509 sq. ft. of stylish and low-maintenance living, complete with 3 bedrooms, 2.5 baths, and a private rear-entry 1-car garage. The main floor features a bright, open layout with a modern kitchen, large pantry, and center island that flows into the dining and living areas, perfect for

  Harman Singh Samson Properties

  119 Nootka Way, Winchester, VA 22602
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  /12

  $389,900 Sold Aug 07, 2025

  • 1,850 Sq Ft
  • $211/SF
  • 197 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2025

  124 Powhatan Trail, Winchester, VA 22602

  Large 1/2 acre lot low in community with Comcast access. Brand new 3 bed, 1,850 sq ft, 3 full baths, 2 car garage, open floor plan, family rm and kitchen with vault. HW floors entire main floor and stairs, tile floors in all baths, upgraded cabinets. BUILDER BONUS HARDWOOD IN BEDROOMS, BUILDER BONUS GRANITE IN KITCHEN, BUILDER BONUS KITCHEN ISLAND, FINISHED REC ROOM (1,850 SQ FT-BIGGEST BANG

  Jim Thomson Realty ONE Group Old Towne

  124 Powhatan Trail, Winchester, VA 22602
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  /29

  Est $524,480 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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  /54

  $517,000 Open Sat 11AM - 12:30PM

  • 3 Beds
  • 2 Baths
  • 2,302 Sq Ft

  101 Delaware Trail, Winchester, VA 22602

  Open House Saturday! Outdoor activities are everywhere you turn at this completely renovated home in Winchester. Hiking, swimming, biking, and kayaking are all close by. As you sit on the beautiful deck, you can listen to the birds while you have your coffee. There are stunning views out of every window of this open concept home. Come see this home for yourself and fall in love.

  

  Kimberly Pace

  EXP Realty, LLC

  (540) 240-9877

  101 Delaware Trail, Winchester, VA 22602
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  /46

  $1,755 - $2,360 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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  /51

  $825,000 Sold Aug 06, 2025

  • 3,612 Sq Ft
  • $228/SF
  • 35 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1981

  373 Greenfield Dr, Winchester, VA 22603

  PRICE IMPROVEMENT! Remodeled & renovated 4 bedroom, 4 full bath rambler, on 8+ manicured acres, has a fully finished lower level apartment with a separate entrance, an 1800 sq ft detached garage with a new propane HVAC system, a hydro pool, and charging station for your electric cars. This property checks all the boxes! The remodeled home features new plumbing and wiring throughout, including

  Jackie Douglass CENTURY 21 New Millennium

  373 Greenfield Dr, Winchester, VA 22603
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  /60

  Est $407,579 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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