Winchester, VA Homes

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  $61,900

  • Land
  • 0.69 Acre
  • $89,710 per Acre

  Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602

  Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 402-9785

  Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602
• Explore Winchester

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  /38

  $2,700 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  218 Munsee Cir, Winchester, VA 22602

  Charming Brand-New 4-Bedroom Home in Premier Winchester Community – Available for RentBedrooms: 4 | Bathrooms: 2.5 | Approx. 1,953 sq ft Welcome to your ideal rental home! Nestled in the desirable Retreat at Winding Creek community, this recently built (2025) single-family residence offers modern comfort, thoughtful design and excellent location. Interior HighlightsBright and open main

  

  Sreedhar Maram

  Maram Realty, LLC

  (540) 870-0736

  218 Munsee Cir, Winchester, VA 22602
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  /49

  $260,000 Sold Nov 26, 2025

  • 2,795 Sq Ft
  • $93/SF
  • 79 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1956

  159 Ashton Dr, Winchester, VA 22603

  Cash only -Sold "AS IS" Great Location! 2-Bedroom, 2-Bath Ranch with Great Potential! Ranch-style home featuring 2 bedrooms and 2 full bathrooms. A large living room with a wood-burning fireplace. Kitchen and separate dining room. Hardwood flooring under carpet. The full basement offers a full bath, ample space for storage, a workshop, or future finished living areas. Outside, you'll find a

  RoxAnn Grimes RE/MAX Roots

  159 Ashton Dr, Winchester, VA 22603
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  /37

  Est $410,102 Not Listed For Sale

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

  204 E Piccadilly St, Winchester, VA 22601

  204 E Piccadilly St, Winchester, VA 22601
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  /12

  $54,900

  • Land
  • 0.73 Acre
  • $75,205 per Acre

  LOTS 7 & 8 Manor Dr, Winchester, VA 22602

  Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have some space between neighbors. Lots 7 & 8 are being sold

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 565-5562

  LOTS 7 & 8 Manor Dr, Winchester, VA 22602
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  /7

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 3,150 Sq Ft
  • Townhouse for Rent

  121 Taft Ave, Winchester, VA 22601

  Charming 2-Bedroom Apartment – Prime Location Near Shenandoah University! This well-maintained 1-level apartment features 2 bedrooms and 1 full bathroom. Enjoy the convenience of a great location—just minutes from Shenandoah University, shopping, dining, and more! WASHER and Dryer in the unit!

  

  Frank Armstrong, IV

  Colony Realty

  (540) 755-3946

  121 Taft Ave, Winchester, VA 22601
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  /4

  $190,000 Sold Nov 25, 2025

  • 894 Sq Ft
  • $213/SF
  • 86 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1994

  303 Barrington Ln, Winchester, VA 22601

  Cute townhome in Huntington Meadows! This home provides a wonderful location to commuter routes and near downtown walking mall in Winchester, VA. Located on the east side of Winchester, VA. This is the ideal home for first time homebuyer or investor. Enough space that the property is easily maintained without feeling cramped. All measurements are approximate.

  Jim Stafford ERA Oakcrest Realty, Inc.

  303 Barrington Ln, Winchester, VA 22601
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  /33

  Est $289,227 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,254 Sq Ft

  116 Windstone Dr, Winchester, VA 22602

  116 Windstone Dr, Winchester, VA 22602
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  $674,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,954 Sq Ft

  Lot 23 Williamson, Winchester, VA 22602

  The Drexel home design is a spacious and versatile single-family home designed to suit a variety of lifestyles. With 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features main-level living with three bedrooms, including a private master suite with a walk-in closet and en-suite bathroom, along with two full bathrooms and a 2-car

  

  Maronda Homes

  Builder

  Lot 23 Williamson, Winchester, VA 22602
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  /12

  $2,200 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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  /35

  $334,900 Sold Nov 25, 2025

  • 1,300 Sq Ft
  • $258/SF
  • 42 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  2225 Harrison St, Winchester, VA 22601

  2225 Harrison Street located in Winchester, VA. One level living in a home remodeled in the fall of 2023. This property is well suited for any living situation. Perfect for a first time home buyer or someone looking to downsize. Granite countertops and stainless steel appliances complement the kitchen. The primary bedroom with an en suite is the perfect getaway. Call today for your private

  Jim Stafford ERA Oakcrest Realty, Inc.

  2225 Harrison St, Winchester, VA 22601
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  /41

  Est $252,435 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,210 Sq Ft

  344 Valley Mill Rd, Winchester, VA 22602

  344 Valley Mill Rd, Winchester, VA 22602
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  /10

  $619,880 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,191 Sq Ft

  107 Malbec Rd, Winchester, VA 22602

  The Rockford home design offers a thoughtful blend of modern functionality and classic comfort, perfect for homeowners who value both style and efficiency. With 4 bedrooms, 2 to 3 bathrooms, and 2,533 square feet of living space, the Rockford is an ideal choice for first-time buyers, growing families, or anyone looking to right-size their lifestyle.Step inside to find an inviting open-concept

  

  Maronda Homes

  Builder

  107 Malbec Rd, Winchester, VA 22602
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  /11

  $2,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Townhouse for Rent

  2047 Harvest Dr, Winchester, VA 22601

  Centrally located townhome available for rent! This home is conveniently situated just minutes from Route 11 with easy access to I-81, this home offers an ideal location for commuters. Nestled in a quiet residential neighborhood with no HOA, it features a one-car garage and a driveway with parking for up to three vehicles. The main level offers durable laminate flooring and a cozy living room

  

  Brock Harris

  Samson Properties

  (540) 417-9298

  2047 Harvest Dr, Winchester, VA 22601
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  /16

  $65,000 Sold Nov 25, 2025

  • Land
  • 5 Acres
  • $13,000 per Acre

  • 9 Days On Market

  Lot 6 Deer Run Dr, Winchester, VA 22602

  Discover the potential of this 5-acre lot located on Deer Run Drive. Property offers privacy and a natural setting with plenty of room to create your own retreat or recreational getaway. There is an existing in-ground pool on site that is not in working condition and will require removal or restoration. A well may have previously existed, but its current functionality is unknown. Property is

  Stephanie Leitao Dandridge Realty Group, LLC

  Lot 6 Deer Run Dr, Winchester, VA 22602
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  Est $469,275 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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  /11

  $624,880 New Construction

  • 2 Beds
  • 2 Baths
  • 2,658 Sq Ft

  159 Williamson Rd, Winchester, VA 22602

  

  Maronda Homes

  Builder

  159 Williamson Rd, Winchester, VA 22602
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  /11

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 2,500 Sq Ft
  • House for Rent

  23 S Stewart St, Winchester, VA 22601

  About 2500 sqft. of completely updated DOWNSTAIRS apartment space in Downtown Winchester. All newer appliances, repainted, refinished wood floors. Sun Room, Porch, Dining room, Living room. even has some cedar closets! What more could you ask for in the heart of downtown Winchester. Landlord pays water, sewer, and all landscaping. Tenants must have minimum 650 Credit score. NO SMOKING.. NO PETS..

  

  Frank Armstrong, IV

  Colony Realty

  (540) 698-5153

  23 S Stewart St, Winchester, VA 22601
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  /5

  $8,000 Sold Nov 25, 2025

  • Land
  • 0.24 Acre
  • $33,333 per Acre

  • 16 Days On Market

  0 Cardinal Dr Unit VAFV2037724, Winchester, VA 22602

  Affordable lot in Wilde Acres / Mountain Falls Park in Winchester, VA! This 0.24-acre lot is ready for your imagination — build a weekend getaway, future home, or simply enjoy your own slice of nature. Surrounded by beautiful mountain and wooded views, this peaceful lot offers the perfect retreat while still being just a short drive to downtown Winchester. New construction is happening throughout

  Chris Roszko Colony Realty

  0 Cardinal Dr Unit VAFV2037724, 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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  /13

  $200,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,430 Sq Ft

  163 Cabin Ln, Winchester, VA 22603

  Discover the potential in this 3 bedroom, 2 bath home on 6.10 unrestricted acres, the perfect opportunity for buyers looking to create their own country retreat. The home is in need of significant work and is being sold AS IS. Outside, you’ll find a detached garage with an apartment above, ideal for guests, rental income, or multi-generational living. Multiple sheds provide ample storage for

  

  Kerry Wysong

  Long & Foster Real Estate, Inc.

  (540) 709-8545

  163 Cabin Ln, Winchester, VA 22603
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  $2,100 per month

  • 2 Beds
  • 1.5 Baths
  • 1,369 Sq Ft
  • Condo for Rent

  6 E Cecil St, Winchester, VA 22601

  Charming Historic 2-Bedroom Rental Just Two Blocks from the Loudoun Street Walking Mall! Live steps from downtown in this beautifully appointed duplex featuring 2-bedrooms and an additional small office/den upstairs. The home is full of historic character and modern comfort, boasting original hardwood floors, soaring ceilings, and timeless architectural charm throughout. Home can be rented

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 452-9535

  6 E Cecil St, Winchester, VA 22601
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  $640,000 Sold Nov 24, 2025

  • 4,385 Sq Ft
  • $146/SF
  • 54 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2005

  150 Harvest Ridge Dr, Winchester, VA 22601

  If you missed your chance to check out this lovely and spacious home - here is your second chance!!! **Find comfort and elegance in this spacious and ready-to-move-in Craftsman-style home in The Village at Harvest Ridge.** Designed for a vibrant lifestyle in a welcoming community, this home showcases a harmonious blend of modern comfort and timeless craftsmanship, and offers nearly 4,500 square

  Bridget Aikens Colony Realty

  150 Harvest Ridge Dr, Winchester, VA 22601
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  /20

  Est $440,527 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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  /6

  $55,000 Pending

  • Land
  • 5.23 Acres
  • $10,516 per Acre

  0 0 Shockeysville Rd, Winchester, VA 22603

  Embrace the serenity of nature on this 5.23-acre wooded lot, offering the perfect blend of privacy, beauty, and possibility. Tucked away in a peaceful setting, this property features a picturesque pond, creating an ideal backdrop for your future home, weekend getaway, or recreational escape. Whether you're dreaming of building a custom home, setting up a private retreat, or simply investing in

  

  Kerry Wysong

  Long & Foster Real Estate, Inc.

  (540) 329-2751

  0 0 Shockeysville Rd, Winchester, VA 22603
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  $3,000 per month

  • 4 Beds
  • 2 Baths
  • 2,658 Sq Ft
  • House for Rent

  5452 Middle Rd, Winchester, VA 22602

  Welcome to 5452 Middle Road, a beautifully renovated farmhouse offering the perfect blend of historic charm and modern comfort, all set on a picturesque 10-acre property. Enjoy peaceful views of rolling pastures, barns, cows, and mountains, all without the upkeep of maintaining the land yourself. This thoughtfully updated home is filled with character, featuring beautiful trim work, hardwood

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 782-3894

  5452 Middle Rd, Winchester, VA 22602
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  /51

  $385,000 Sold Nov 24, 2025

  • 1,591 Sq Ft
  • $242/SF
  • 9 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2003

  1823 Kershaw Ln, Winchester, VA 22601

  This beautiful home in Willow Lawn Cottages has been freshly painted, professionally cleaned and lovingly prepared just for you. Step inside to find rich wooden floors, vaulted ceilings, and a cozy fireplace that immediately make you feel at home. Imagine arranging your favorite furniture in bright, airy rooms filled with natural light. One of the largest floor plans in the neighborhood, this

  Natalie Langford ERA Oakcrest Realty, Inc.

  1823 Kershaw Ln, Winchester, VA 22601
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  /43

  Est $651,963 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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  /2

  $365,000 Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  127 Shirley St, Winchester, VA 22601

  Comfortable living at this split-foyer home located in the heart of the City of Winchester. On the main level, you’ll find three bedrooms and a full bath. The lower level features a fourth bedroom plus a second full bath — ideal for guests, or a home office. Location is a standout. You’re just minutes from downtown dining, shopping, and community events, and enjoy easy access to schools, parks,

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 802-5087

  127 Shirley St, Winchester, VA 22601
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  $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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  /102

  $679,900 Sold Nov 24, 2025

  • 4,167 Sq Ft
  • $163/SF
  • 41 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  132 Cahille Dr, Winchester, VA 22602

  Prime Winchester location! 3-car garage and spacious driveway! This dream home is located minutes to commuter Routes 7, 50 and 81 and minutes from shopping, dining and entertainment in Old Town Winchester! Nestled in the prestigious Raven Pointe community, this exquisite Colonial home embodies luxury and sophistication. Built in 2005, this lovingly maintained home features a harmonious blend of

  Danielle Dojcak Century 21 Redwood Realty

  132 Cahille Dr, Winchester, VA 22602
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  /60

  Est $427,866 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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  $445,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 2,176 Sq Ft

  125 Alliance Ct, Winchester, VA 22602

  Welcome to this beautifully maintained home located in the highly sought-after Freedom Manor community in Winchester, VA! Ideally situated just minutes from shopping, dining, and everyday conveniences—with quick access to I-81—this home offers the perfect combination of comfort, functionality, and location.Inside, the main level features stylish and durable luxury vinyl plank (LVP)

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  (540) 730-2810

  125 Alliance Ct, Winchester, VA 22602
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  $2,175 per month

  • 4 Beds
  • 3.5 Baths
  • 1,925 Sq Ft
  • Townhouse for Rent

  156 Munsee Cir, Winchester, VA 22602

  BRAND NEW SMART HOME CONSTRUCTION! MOVE NOW! Almost End Unit Three Level Townhome. Entry Level with Roomy 4th Bedroom/Rec Room and Full Ensuite Bath! DRAMATIC OPEN FLOOR PLAN MAIN, WELCOME FAMILY AND FRIENDS! SUNDRENCHED KITCHEN, Glass 5 Burner Cooktop Range, Oversized Sink, Granite/Stainless/Center Isle, Double Door Fridge, and Access to Balcony! Living Room/Dining Room with High Ceilings and

  Helen Manning Premiere Property Management, LLC

  156 Munsee Cir, Winchester, VA 22602
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  /26

  $215,000 Sold Nov 24, 2025

  • 1,091 Sq Ft
  • $197/SF
  • 34 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1951

  1033 Sunnyside Dr, Winchester, VA 22603

  Price Reduced - Come check out this charming bungalow cottage, easy to show, freshly painted, located just off Rt. 522 North, outside the northern border of the City of Winchester. Spacious, fully equipped kitchen, with range, refrigerator, dishwasher, plenty of cabinets, counter space and table space. Offering two nice-sized bedrooms with good closet space, Full bath has laundry area with washer

  Gail Farrace Colony Realty

  1033 Sunnyside Dr, Winchester, VA 22603
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  /27

  Est $373,593 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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  /24

  $299,900 Under Contract

  • 2 Beds
  • 1 Bath
  • 858 Sq Ft

  525 E Cork St, Winchester, VA 22601

  Beautiful and affordable Gem in the middle of Winchester City.Private, fully fenced yard with extra parking and storage. Updated A/C and two year old roof.

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 900-1951

  525 E Cork St, Winchester, VA 22601
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  /22

  Call for Price

  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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  /2

  $430,000 Sold Nov 24, 2025

  • 2,499 Sq Ft
  • $172/SF
  • 5 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2014

  201 Cobble Stone Dr, Winchester, VA 22602

  Welcome to 201 Cobble Stone Drive! Beautifully maintained 3-bedroom, 3.5-bath, End-Unit townhome with a 2-car garage in the Fieldstone community. This home sits on one of the premium lots in the neighborhood, offering added space, privacy, and a peaceful setting. Inside, you’ll find an open and welcoming floor plan with hardwood floors throughout the main level, a bright kitchen with granite

  Natasha Roberts Realty ONE Group Old Towne

  201 Cobble Stone Dr, Winchester, VA 22602
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  /34

  Est $301,169 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  201 Fawn Dr, Winchester, VA 22602

  201 Fawn Dr, Winchester, VA 22602

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