Winchester, VA Homes

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  /25

  $279,999

  • 2 Beds
  • 1 Bath
  • 856 Sq Ft

  621 Panther Dr, Winchester, VA 22602

  Wilde Acres offers peaceful country living just 15–20 minutes from Winchester City. The property spans three lots, for a total of approximately .75 acres, and features multiple outbuildings with power and heat. It's ideal for outdoor enthusiasts, nature lovers, and gardeners. The various outdoor spaces provide perfect areas for a workshop, recreation room, or extensive storage. This

  

  Lori Bales

  Keller Williams Realty

  (540) 779-1824

  621 Panther Dr, Winchester, VA 22602
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  /33

  $1,400 - $1,800 per month

  Madison Village Apartments (Winchester)

  1 - 2 Beds

  110 Bulmer Loop, Winchester, VA 22602

  Our community is perfect for those who enjoy spending time outside living a healthy, lively lifestyle by using the walking trails, outdoor common areas, and dog park, as well as for those who appreciate a home that is a retreat from the business of everyday life. We are conveniently located a few short miles from Shenandoah University, I-81, Rt. 8 and Rt. 50 in Winchester, VA. Our apartments

  110 Bulmer Loop, Winchester, VA 22602
• 

  

  

  /20

  $131,500 Sold Jul 30, 2025

  • 384 Sq Ft
  • $342/SF
  • 24 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1969

  305 Raccoon Dr, Winchester, VA 22602

  Escape to this cozy 1-bedroom cottage, nestled on a level wooded lot—a perfect blend of comfort and rustic charm. Inside, you'll find knotty pine walls and hardwood floors that create a warm and welcoming atmosphere.Unwind on the screened-in porch, ideal for sipping your morning coffee or watching wildlife in the peaceful, natural surroundings. Whether you're looking for a weekend

  Amy Longerbeam RE/MAX Roots

  305 Raccoon Dr, Winchester, VA 22602
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  /27

  Est $362,755 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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  /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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  /14

  $1,700 per month

  • 2 Beds
  • 1 Bath
  • 1,028 Sq Ft
  • House for Rent

  419 Shenandoah Place, Winchester, VA 22601

  A completely renovated ranch style home Upgraded appliances, new HVAC, fenced rear yard Quiet cul de sac Minutes from Old Town Winchester and Rt 7 Owner is requesting strong income and credit score Pets will be considered Cats are ok $ 42 app fee. Cash or money order made out to Crum Realty Inc

  Carolyn Waymack Crum Realty, Inc.

  419 Shenandoah Place, Winchester, VA 22601
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  /32

  $390,000 Sold Jul 30, 2025

  • 2,124 Sq Ft
  • $184/SF
  • 27 Days On Market

  • Studio
  • Built 1930

  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

  619 S Cameron St, Winchester, VA 22601
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  /49

  Est $637,784 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  117 Thompson Ct, Winchester, VA 22602

  117 Thompson Ct, Winchester, VA 22602
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  /49

  $649,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,591 Sq Ft

  101 Morgan St, Winchester, VA 22601

  Downtown Winchester - 2 blocks from the walking mall with in-law suite or lower level rental potential! From the moment you arrive, you’ll be drawn in by this home’s timeless symmetry, classic brick exterior, and welcoming front porch. Thoughtful landscaping and charming details set the stage for what’s inside. With 5 bedrooms and 3 full baths, there’s plenty of space for everyone. The

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 858-1339

  101 Morgan St, Winchester, VA 22601
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  /17

  $500 - $2,000 per month

  Brookfield Corporate Apartments

  1 - 2 Beds

  548 Brookfield Dr, Winchester, VA 22601

  We are excited to share that we are under new ownership and management, and we're eager to welcome new guests to our community.Located at 500 Brookfield Drive, Winchester, VA 22601, Brookfield Corporate Apartments offers spacious, fully furnished one and two-bedroom apartments. Each apartment is designed with your comfort in mind and comes equipped with linens, kitchenware, two TVs with

  548 Brookfield Dr, Winchester, VA 22601
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  /40

  $520,000 Sold Jul 30, 2025

  • 2,489 Sq Ft
  • $209/SF
  • 34 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2022

  116 Lenore Ln, Winchester, VA 22602

  Stunning home in the heart of Raven Oaks, this residence is a testament to both beauty and functionality. Thoughtful upgrades and features enhance the overall appeal and convenience of this beautiful home. The kitchen, the heart of this home, has been upgraded to perfection, there is also a bedroom and one full bathroom on the main level too and a gourmet kitchen with a large center island. On

  Christian Davis RE/MAX Executives

  116 Lenore Ln, Winchester, VA 22602
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  /36

  Est $431,051 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,522 Sq Ft

  151 Doonbeg Ct, Winchester, VA 22602

  151 Doonbeg Ct, Winchester, VA 22602
• 

  

  /13

  $749,000 Coming Soon

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

  1205 Caroline St, Winchester, VA 22601

  **Do Not Miss This One!**Professional Photos Coming Soon** 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. With nearly 3,000 square feet of thoughtfully designed space on the main level, this

  

  Jim Shebest

  Coldwell Banker Realty

  (540) 802-5378

  1205 Caroline St, Winchester, VA 22601
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  /22

  $1,495 per month

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

  7 W Piccadilly St Unit F, Winchester, VA 22601

  Live, work and play in historic downtown Winchester! Presenting this beautiful 1 bedroom, 1 bathroom apartment conveniently located on Piccadilly Street right next to the pedestrian mall. The apartment offers beautiful hardwood floors, tall ceilings, washer and dryer in the unit and more. You will also receive an assigned parking space next to the building. A literal stone's throw from shops and

  Chris Roszko Colony Realty

  7 W Piccadilly St Unit F, Winchester, VA 22601
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  /45

  $515,000 Sold Jul 29, 2025

  • 1,881 Sq Ft
  • $274/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1965

  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

  331 Ridge Ave, Winchester, VA 22601
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  /38

  Est $711,568 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,095 Sq Ft

  216 Taggart Dr, Winchester, VA 22602

  216 Taggart Dr, Winchester, VA 22602
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  /9

  $225,000 Under Contract

  • 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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  /37

  $1,029 - $1,630 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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  /19

  $510,000 Sold Jul 29, 2025

  • 2,264 Sq Ft
  • $225/SF
  • 10 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2025

  134 Webster Ct, Winchester, VA 22603

  Now under construction and will be Ready for Summer move in!! Welcome home to your new two level Fitzgerald located within Hiatt Pointe, the active adult section of Snowden Bridge for those 55 or better!!This exceptional garden home, situated on a premium lot within a vibrant community, offers streamlined main-level living. The kitchen, a focal point of the residence, features Carrara Mist

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  134 Webster Ct, Winchester, VA 22603
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  /17

  Est $269,581 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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  /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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  /19

  $3,100 per month

  • 3 Beds
  • 1.5 Baths
  • 1,696 Sq Ft
  • House for Rent

  1315 Handley Ave, Winchester, VA 22601

  1 block away from Handley High School! This all brick 2 story home features 3 bedroom 1 1/2 baths with hardwood floors throughout the first and 2nd floors, freshly painted throughout, all new windows, and new flooring in the kitchen. Large family room with built in shelving and fireplace with woodstove insert. Full unfinished attic and basement. Beautifully landscaped rear lawn with patio and

  Misty Miller OliveTree Property Group, LLC

  1315 Handley Ave, Winchester, VA 22601
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  /24

  $482,990 Sold Jul 29, 2025

  • 1,953 Sq Ft
  • $247/SF
  • 29 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  110 Manasquan Way, Winchester, VA 22602

  The Pine is a popular floorplan for all the right reasons! 4 bedrooms, 2.5 bathrooms, and a 2-car garage. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for seating, an impressive corner pantry, plenty of cabinet space and stainless-steel appliances that

  Brooks Sears D R Horton Realty of Virginia LLC

  110 Manasquan Way, Winchester, VA 22602
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  /83

  Est $893,947 Not Listed For Sale

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

  420 N Hayfield Rd, Winchester, VA 22603

  420 N Hayfield Rd, Winchester, VA 22603
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  /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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  /26

  $1,695 - $1,702 per month

  Fort Collier Terrace

  1 - 3 Beds

  900-1024 N Braddock St, Winchester, VA 22601

  Welcome to Fort Collier Terrace, an inviting community you'll love being part of. Our apartments in Winchester, VA, come in one, two, and three-bedroom layouts that range from 800 to 1,000 square feet. Aside from the generous living quarters, you'll find everything you need to feel right at home.Located near N Cameron Street and Martinsburg Pike, you're a stone's throw away from the top dining,

  900-1024 N Braddock St, Winchester, VA 22601
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  /37

  $350,000 Sold Jul 29, 2025

  • 1,509 Sq Ft
  • $232/SF
  • 51 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  119 Nootka Way, Winchester, VA 22602

  This rear-load, two-level townhome offers 1,509 square feet of well-designed living space, perfect for modern comfort and convenience. With three spacious bedrooms and 2.5 baths, it’s ideal for those seeking a low-maintenance lifestyle. The open layout includes a welcoming main level with plenty of room for entertaining, while the second floor hosts the bedrooms for added privacy. The home also

  Brooks Sears D R Horton Realty of Virginia LLC

  119 Nootka Way, Winchester, VA 22602
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  /3

  Est $251,500 Not Listed For Sale

  403 Panther Dr, Winchester, VA 22602

  403 Panther Dr, 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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  /23

  $1,650 per month

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Townhouse for Rent

  215 Banbury Terrace, Winchester, VA 22601

  AFFORDABLE TOWNHOUSE. COMMUTER CONVENIENT to Rt 7 and I-81 and close to shopping and services. Lovely, well-maintained 2-bedroom townhouse. Hardwood floor in living room. Spacious kitchen with dining area and large pantry. Appliances include washer and dryer. Storage room off rear. Near playground and common area. Landlord pays HOA fees. Pets considered case-by-case. No smoking. Minimum one-year

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  215 Banbury Terrace, Winchester, VA 22601
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  /15

  $159,900 Sold Jul 29, 2025

  • 861 Sq Ft
  • $186/SF
  • 222 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1971

  236 Doe Trail, Winchester, VA 22602

  This private property on a nice quarter-acre corner lot has a new roof, kitchen cabinets, and counter tops, new drywall where needed with insulation in walls. New electric baseboard heat, lights updated and electric brought to code. New laminate flooring throughout. Plumbing has been repaired as needed and winterized. Existing stove, refrigerator, and stackable washer and dryer stay.

  Liz McDonald Dandridge Realty Group, LLC

  236 Doe Trail, 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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  /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

  $1,490 - $1,745 per month

  Blue Ridge Apartments

  2 - 4 Beds

  2260 Wilson Blvd, Winchester, VA 22601

  Discover the perfect blend of comfort and convenience at Blue Ridge Apartments in Winchester, VA. Our recently updated homes feature a variety of floor plans. Nestled in a pet-friendly community, you're just minutes away from Winchester's scenic spots, historic downtown, Apple Blossom Mall, and major employers. With easy access to I-81 and Route 7, the best of Winchester is always within reach.

  2260 Wilson Blvd, Winchester, VA 22601
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  /18

  $330,000 Sold Jul 28, 2025

  • 1,202 Sq Ft
  • $275/SF
  • 0 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1830

  411 N Loudoun St Unit 104, Winchester, VA 22601

  Just minutes from the walking mall and the charming shops and restaurants of downtown Winchester, this fantastic two-story condo offers the perfect blend of historic character and modern comfort.Step inside to find beautiful hardwood floors and stylish finishes throughout. The fully equipped kitchen features rich dark cabinetry, granite countertops, gas cooking, and a spacious peninsula that

  Lori Bales Keller Williams Realty

  411 N Loudoun St Unit 104, Winchester, VA 22601
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  /49

  Est $413,147 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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  /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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  /34

  $2,500 per month

  • 4 Beds
  • 3 Baths
  • 2,105 Sq Ft
  • House for Rent

  301 Wood Ave, Winchester, VA 22601

  Welcome to this beautifully maintained home located in the heart of Winchester! Nestled on a quiet street, this residence offers both comfort and convenience—just minutes from Winchester Medical Center, Shenandoah University, and Old Town Winchester.Step inside to find a bright and inviting living space, complemented by hardwood floors and large windows that let in abundant natural

  Bailey Cooper RE/MAX Gateway

  301 Wood Ave, Winchester, VA 22601
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  /47

  $309,000 Sold Jul 28, 2025

  • 2,348 Sq Ft
  • $132/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1950

  233 Molden Dr, Winchester, VA 22601

  Charming All-Brick Ranch with Endless Potential in Established Neighborhood! Don't miss this solid 3+ bedroom, 1.5 bath all-brick ranch offering timeless appeal and the opportunity to make it your own. Nestled in a well-established neighborhood, this home features original hardwood floors, a cozy fireplace for chilly evenings, and radiant ceiling heat for comfortable, energy-efficient warmth

  Kevin Smith Sager Real Estate

  233 Molden Dr, 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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