Winchester County VA Homes for Sale

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  /57

  $630,000

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft

  716 S Washington St, Winchester, VA 22601

  Well-maintained and full of charm, this 2,774 sq ft, 4-bedroom, 3.5-bath home sits on a 1/3-acre lot in the heart of Old Town Winchester—just one block from Handley High School and a short distance to the vibrant Winchester Walking Mall. Built over 150 years ago, this home features original pine floors, a formal living and dining room, a grand marble-tiled foyer, and a dedicated office with

  Lisa Alberti Roberts Realty Group, LLC

  716 S Washington St, Winchester, VA 22601
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  /25

  $529,999

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  609 Quartzite Cir, Winchester, VA 22601

  Welcome to 609 Quartzite Circle, a meticulously maintained 4-bedroom, 3-bathroom home nestled in the desirable Limestone Terrace subdivision of Winchester, VA. This spacious residence offers 2,312 square feet of comfortable living space, featuring an open floor plan with cathedral ceilings, recessed lighting, and gleaming hardwood floors that enhance its bright and inviting atmosphere.

  Berta Vasquez Samson Properties

  609 Quartzite Cir, Winchester, VA 22601
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  /35

  $665,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  112 W Germain St, Winchester, VA 22601

  100-Year-Old Downtown Winchester Charmer – Brought Back to Life in 2025!This beautifully restored century-old home has been completely reimagined from the ground up, blending timeless character with top-tier modern upgrades. Located in the heart of historic downtown Winchester, this home underwent a full-gut renovation in 2025—everything is new. From the all-new electrical wiring and replaced

  Amanda Magana RE/MAX Roots

  112 W Germain St, Winchester, VA 22601
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  /71

  $1,199,997

  • 5 Beds
  • 6 Baths
  • 6,517 Sq Ft

  331 N Braddock St, Winchester, VA 22601

  This circa 1863 Italianate home is located in the heart of Winchester's historic district within a short walk to Handley Library and downtown. The home has been elegantly restored, blending timeless charm with modern comforts. The interior is restored to its original grandeur with high ceilings, hardwood floors, decorative moldings, and fireplaces in every room. Fully updated gourmet kitchen with

  John Schroth Colony Realty

  331 N Braddock St, Winchester, VA 22601
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  /40

  $429,900

  • 3 Beds
  • 3.5 Baths
  • 2,721 Sq Ft

  1324 Ramseur Ln, Winchester, VA 22601

  Elegant Main-Level Condo in The Mews at MeadowbranchWelcome to effortless luxury living in one of Meadowbranch’s most sought-after communities! This stunning main-level condo combines the space and comfort of a single-family home with the convenience and ease of condo living. Bright, open, and beautifully finished, this rare gem in The Mews at Meadowbranch can be yours! Inside, you'll find three

  Jeanne Mezzatesta Colony Realty

  1324 Ramseur Ln, Winchester, VA 22601
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  /22

  $360,000

  • 3 Beds
  • 2 Baths
  • 1,060 Sq Ft

  601 Fairview Ave, Winchester, VA 22601

  Fully Renovated Gem in the Heart of Winchester! Welcome to 601 Fairview Ave, where modern upgrades meet timeless charm! This beautifully remodeled 3-bedroom, 2-bathroom rambler offers the perfect blend of comfort and convenience in one of Winchester’s most desirable locations.Step inside to discover a brand-new kitchen featuring stylish finishes, sleek countertops, and modern cabinetry—ready for

  Jorge Najarro Samson Properties

  601 Fairview Ave, Winchester, VA 22601
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  /67

  $625,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

  Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers convenience,

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
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  /42

  $359,000

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

  107 E Monmouth St, Winchester, VA 22601

  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 feel right at home. Warm wood

  Jeanne Mezzatesta Colony Realty

  107 E Monmouth St, Winchester, VA 22601
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  /34

  $294,900

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  2301 Tower Ave, Winchester, VA 22601

  Welcome to this charming and cozy budget friendly home. With 3 bedrooms on the main level and a full basement below with tons of room for future expansion that walks out to a large off-street parking area this home is bursting with potential! The big ticket items are already there with newer high-end appliances, heat pump and central air, 200 amp service, etc this home is ready for your cosmetic

  Clint Pierpoint NextHome Realty Select

  2301 Tower Ave, Winchester, VA 22601
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  /57

  $365,000

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft

  1005 Pennsylvania Ave, Winchester, VA 22601

  This charming classic brick ranch in Winchester, VA, features 3 bedrooms and 2 full bathrooms, with easy access to downtown Winchester. As you approach, the covered front porch sets a welcoming tone. The basement has a separate entrance and additional space for bedrooms, a laundry area, and a full bathroom. Recent updates include an HVAC system, a washer and dryer, and complete renovations of

  Nathalie Acosta Spring Hill Real Estate, LLC.

  1005 Pennsylvania Ave, Winchester, VA 22601
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  /24

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  16 W Clifford St, Winchester, VA 22601

  Wooden construction, Alley side home ready for construction. Boarders Downton Winchester, blocks form Historic Old town, Walking Mall and restaurant Alley. 5 minutes drive to Shenandoah University. Winchester has been named fastest growing place in all of VA. Best place to retire by FORBS magazine. 15 hour outside of Washington DC excellent location for rental. City approved plans to

  Carlos Beamon Samson Properties

  16 W Clifford St, Winchester, VA 22601
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  /34

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,313 Sq Ft

  320 Highland Ave, Winchester, VA 22601

  Welcome to this centrally located home in the heart of Winchester. With easy access to I-81, this home is in a great commuter's location. Just a quick walk or drive away are the charming shops and restaurants of Historic Old Town Winchester. The main level features hardwood floors, a living room with wood-burning brick fireplace and a formal dining room, featuring a charming a built in China

  Heloisa Amar Samson Properties

  320 Highland Ave, Winchester, VA 22601
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  /2

  $300,000

  • 8 Beds
  • 5 Baths
  • 12,127 Sq Ft

  910 Franklin St, Winchester, VA 22601

  PRICE RARE UNIQUE OPPORTUNITY KNOCKS!PRICE DROP!Warehouse and all 4 units cleaned, and junk removed - Ready for new investor.Do not miss this rare opportunity to own this rare, unique mixed-use property in Winchester. Work with the city of Winchester and turn this into your dream project!Excellent rate of return with existing units. Two residential apartments upstairs and two

  Pakeeza Akhtar The KOR Group, Inc.

  910 Franklin St, Winchester, VA 22601
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  /27

  $279,000

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft

  1309 Commerce St, Winchester, VA 22601

  This charming all-brick ranch is making its first appearance on the market since the 1970s! It's a fantastic opportunity for first-time homebuyers or investors looking to add their personal touch. The home features three bedrooms, with hardwood floors, carpet, and a full bath on the main level. The cozy family room and kitchen complete the main floor, with hardwood flooring said to be beneath

  Jeff Boppe Long & Foster Real Estate, Inc.

  1309 Commerce St, Winchester, VA 22601
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  /43

  $349,900

  • 3 Beds
  • 2.5 Baths
  • 1,008 Sq Ft

  205 Parkway St, Winchester, VA 22601

  WELCOME to this charming, conveniently-located, two-level brick rambler home!! This spacious, well-maintained property has comfortable living spaces inside and out. This cozy home features two finished levels with hardwood floors on the main level and flooring on the basement level as well. The main level features three bedrooms and a nice-sized kitchen. Your outdoor retreat awaits just beyond

  Agustin Martinez Spring Hill Real Estate, LLC.

  205 Parkway St, Winchester, VA 22601
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  /61

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  1380 Magruder Ct, Winchester, VA 22601

  $10,000 PRICE REDUCTION!! SELLER OFFERING 5 YEAR SWIMMING POOL AND TENNIS/PICKLEBALL COURT MEMBERSHIP!!!Rare opportunity in a fabulous location...walk to John Kerr Elementary and Handley High Schools, the Museum of the Shenandoah Valley and Winchester Medical Center!! Close to Old Town Winchester. Well maintained colonial style home in highly desirable Downs at Meadow Branch community. Bright

  Stuart Wolk ERA Oakcrest Realty, Inc.

  1380 Magruder Ct, Winchester, VA 22601
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  /56

  $2,098,000

  • Studio
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  In town location for this completely remodeled multi unit property. This property contains 4 homes and 2 apartments that have been completely refinished. The main home is currently lived in by the owner and is attached to a indoor swimming pool. The other 3 homes and 2 apartments are leased and are bringing over$10,500 monthly. If you choose rent the main house income would be much higher. .

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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  /34

  $429,900

  • 4 Beds
  • 2 Baths
  • 1,762 Sq Ft

  2320 Tower Ave, Winchester, VA 22601

  HUGE PRICE CUT!!!Don't drag your feet before this one disappear!!! Welcome to 2320 Tower Ave , Two Car garages ,4 legal bedrooms , 2 full bathrooms single family in quiet cul-de-sac is what you are waiting for is finally here to make it yours, the entire house just came out of renovations from freshly painted , Master Bathroom/Quartz, High Ceiling Family room, New Carpet, New

  Alex Adomako-Acheampong Samson Properties

  2320 Tower Ave, Winchester, VA 22601
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  /44

  $329,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  127 S Euclid Ave, Winchester, VA 22601

  REDUCE PRICE!!!!! BEATIFULL HOME!!! Fully Renovated Gem in the Heart of Winchester! Welcome to 127 Euclid , where modern upgrades meet timeless charm! This beautifully remodeled 3-bedroom, 2-bathroom rambler offers the perfect blend of comfort and convenience in one of Winchester’s most desirable locations. Step inside to discover a brand-new kitchen featuring stylish finishes, quartz

  Carolina Mosquera Weichert, REALTORS

  127 S Euclid Ave, Winchester, VA 22601
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  /56

  $2,098,000

  • 4 Beds
  • 2.5 Baths
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  Opportunity meets elegance in this fully remodeled multi-unit gem, perfectly situated in a prime in-town location. This unique property features four beautifully refinished homes and two modern apartments, offering both luxury and income potential in one impressive package.The main residence—currently owner-occupied—is a standout, seamlessly connected to a private indoor swimming pool, creating a

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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  /26

  $315,000

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

  806 Appleseed Ct, Winchester, VA 22601

  Newly painted interior. This 3 bedroom, 1.5 bath townhouse with a large rec room in the lower level is located just where you want to be. Great community and so convenient to shopping and everyday life necessities.

  Joan Donald MarketPlace REALTY

  806 Appleseed Ct, Winchester, VA 22601
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  /13

  $275,000

  • Land
  • 0.97 Acre
  • $283,505 per Acre

  823 Armistead St, Winchester, VA 22601

  An amazing opportunity to acquire a prime lot in the City of Winchester, Virginia, perfect for your dream home!Nestled in the established Meadows Branch neighborhood, one of Winchester’s most upscale developments of beautifully crafted homes, this spacious 0.97 acre lot backs to the protected Abrams Creek Wetlands Preserve and Winchester’s Green Circle Trail.This ready-to-build homesite

  Janet Flaherty Keller Williams Realty

  823 Armistead St, Winchester, VA 22601
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  /9

  $119,900

  • Land
  • 0.12 Acre
  • $999,167 per Acre

  116-118 W Leicester St, Winchester, VA 22601

  Unique opportunity to own a piece of land in Historic Downtown Winchester. Located between Braddock and Washington Streets South of the Old Town Walking Mall. The property is within steps to Washington Street and the Apple Blossom Festival Parade route. The lots are located within the Historic District of Winchester. Two parcels are included in this listing. Previously, the lots were

  Kim Hurst MarketPlace REALTY

  116-118 W Leicester St, Winchester, VA 22601
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  /7

  $53,500

  • Land
  • 0.06 Acre
  • $891,667 per Acre

  118 W Leicester St, Winchester, VA 22601

  Unique opportunity to own a piece of land in Historic Downtown Winchester. Located between Braddock and Washington Streets South of the Old Town Walking Mall. The property is within steps to Washington Street and the Apple Blossom Festival Parade route. The lot is located within the Historic District of Winchester. One parcels is included in this listing. Two lots are available for

  Kim Hurst MarketPlace REALTY

  118 W Leicester St, Winchester, VA 22601
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  /8

  $66,500

  • Land
  • 0.06 Acre
  • $1,108,333 per Acre

  116 W Leicester St, Winchester, VA 22601

  Unique opportunity to own a piece of land in Historic Downtown Winchester. Located between Braddock and Washington Streets South of the Old Town Walking Mall. The property is within steps to Washington Street and the Apple Blossom Festival Parade route. The lot is located within the Historic District of Winchester. One parcels is included in this listing. This lot includes a water and sewer

  Kim Hurst MarketPlace REALTY

  116 W Leicester St, Winchester, VA 22601
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  /10

  $599,000

  • Land
  • 0.09 Acre
  • $6,655,556 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
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  /11

  $1,100,000

  • Land
  • 2.48 Acres
  • $443,548 per Acre

  2725 S Pleasant Valley Rd, Winchester, VA 22601

  Location, location, location. Here is your chance to own one of the few commercial/industrial lots located in the highly desirable Winchester City. This cleared, blank slate is ready for your next business endeavor. Currently zoned as CM-1 (Commercial/Industrial), the property offers roughly 465 ft of prime road frontage, perfect for displaying your establishment.Current use regulations

  Kaitlyn Behr RE/MAX Roots

  2725 S Pleasant Valley Rd, Winchester, VA 22601
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  /73

  $970,800

  • 3 Beds
  • 3.5 Baths
  • 3,793 Sq Ft

  1321 Vanceright Cir, Winchester, VA 22601

  Rare and unique opportunity! Be just the second owner of this modern, custom, architect designed, home unlike any other! This one-of a kind contemporary home sits on the slope of one of the highest points in Winchester. It was designed by renowned local architects, Reader and Swartz, and built in 2006 by Ritter Construction. The Handley Heights location, next to an old Winchester neighborhood,

  John Scully Colony Realty

  1321 Vanceright Cir, Winchester, VA 22601
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  /8

  $299,000

  • Land
  • 0.60 Acre
  • $498,333 per Acre

  229 S Pleasant Valley Rd, Winchester, VA 22601

  FOR SALE+PAD SITE APPROVED* (!) Pad site approved for 2000 SF professional office building on Pleasant Valley Road, Winchester City. Very rare opportunity! Will have direct access from Pleasant Valley Road. Excellent visibility and traffic count! Ideal for professional medical office building. Asking $299K. Contact Agent for more details!

  Gillian Greenfield Coldwell Banker Premier

  229 S Pleasant Valley Rd, Winchester, VA 22601
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  /3

  $470,335

  • Land
  • 1.37 Acres
  • $343,310 per Acre

  0 Senseny Rd Unit VAFV2009062, Winchester, VA 22602

  PRICE REDUCED!! Owners are looking for reasonable offers. Lot fronts on Senseny road but can be accessed from the shopping center parking lot. Also can be purchased jointly with Lot H. Lot is flat and ready for development. The house adjoining the lot may also be available for purchase.

  John Coontz Commercial Specialists

  0 Senseny Rd Unit VAFV2009062, Winchester, VA 22602
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  /2

  $500,000

  • Studio
  • 1,175 Sq Ft

  513 and 525 Monticello St, Winchester, VA 22601

  For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

  Brett Haynes Oakcrest Commercial LLC.

  513 and 525 Monticello St, Winchester, VA 22601
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  /2

  $360,000

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft

  2940 Grace St, Winchester, VA 22601

  Welcome to your charming Cape Cod retreat! This delightful 3-bedroom, 1-bathroom home seamlessly blends classic character with modern comfort. Built in 1955, it offers a warm and inviting atmosphere—perfect for anyone looking for a cozy and welcoming place to call home. --- Step inside to a thoughtfully designed layout that makes the most of the 936 square feet of finished living space.

  Lauren Smith-Washbourne Coldwell Banker Premier

  2940 Grace St, Winchester, VA 22601
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  /2

  $120,000

  • Land
  • 0.12 Acre
  • $1,000,000 per Acre

  520 Highland Ave, Winchester, VA 22601

  Ready to build your dream home or investment property in the City of Winchester? Now is your opportunity to purhcase a parcel in the heart of Winchester. HR1 Zoning-High density Residential. No water, sewer or electric to property.

  Dana Cloud Realty ONE Group Old Towne

  520 Highland Ave, Winchester, VA 22601
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  /32

  $539,900

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft

  201 Parkway St, Winchester, VA 22601

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
• 

  

  /25

  $300,000

  • 4 Beds
  • 2.5 Baths
  • 1,810 Sq Ft

  342 Fairview Ave, Winchester, VA 22601

  Derek Greene The Greene Realty Group

  342 Fairview Ave, Winchester, VA 22601
• 

  

  /20

  $249,000

  • 2 Beds
  • 1 Bath
  • 1,542 Sq Ft

  413 S Braddock St, Winchester, VA 22601

  Roger Walker Crum Realty, Inc.

  413 S Braddock St, Winchester, VA 22601
• 

  

  /10

  $1,200,000 New Construction

  • 3 Beds
  • 3 Baths

  823 Armistead St, Winchester, VA 22601

  **This is a To Be Built Home in the Meadow Branch Section of Winchester City*** Experience the perfect blend of timeless farmhouse charm and modern luxury in this beautiful new construction home built by respected local custom builder Dave Hepler. With 3 bedrooms and 3 full bathrooms, this thoughtfully designed residence offers quality craftsmanship, stylish finishes, and a layout ideal for both

  Janet Flaherty Keller Williams Realty

  823 Armistead St, Winchester, VA 22601
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  /6

  $452,539 New Construction

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

  HOMESITE 20 Monteith Dr, Winchester, VA 22601

  *OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF PREFERRED LENDER AND TITLE.*This home has a Gourmet Kitchen: cooktop with chimney style hood, wall microwave, wall oven, upgraded gourmet Energy Star stainless steel appliances, Refrigerator is a French 2 door style, the kitchen island is extended to comfortably seat 4, and a box bay window in the rear of the home

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 20 Monteith Dr, Winchester, VA 22601
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  /6

  $433,880 New Construction

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

  HOMESITE 117 Monteith Dr, Winchester, VA 22601

  *OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF PREFERRED LENDER AND TITLE.*Beautiful open concept living 3 level town home built on concrete slab with a walk-out basement. Finished Rec Room - 13'1" x 11'1" with a door to the outside/backyard. The living room area is15'3" x 17', open kitchen layout with an extended island, and a box bay window in the rear of

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 117 Monteith Dr, Winchester, VA 22601
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  /6

  $429,340 New Construction

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

  HOMESITE 114 Monteith Dr, Winchester, VA 22601

  *OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF PREFERRED LENDER AND TITLE. CONTACT CO LISTING AGENT/CONSULTANT FOR DETAILS* Late Summer Delivery in Winchester featuring walking trails, lush landscaping multi sport court for basketball and pickleball a welcoming pavilion and tot lot. Bedford II, 3 level townhome features a partial stone front with 1 car garage.

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 114 Monteith Dr, Winchester, VA 22601

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