Winchester County VA Homes for Sale

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  $1,250,000

  • 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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  /71

  $1,250,000

  • 7 Beds
  • 7 Baths
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! You have to see this $1M renovation by an architect out of NYC. 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

  

  Lori Bales

  Keller Williams Realty

  (540) 660-3543

  202 S Washington St, Winchester, VA 22601
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  /104

  $869,500

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

  1517 Brookdale Ct, Winchester, VA 22601

  Welcome to this stunning and spacious brick Colonial, perfectly situated on one of the best lots in Morlyn Hills, nestled on a quiet cul-de-sac and overlooking a 45-acre protected wetland preserve. Impeccably maintained and offering over 6,500 + of finished square feet of elegant living space, this home features 4 bedrooms, 4.5 baths, and an impressive array of upgrades throughout.From the moment

  

  Brock Harris

  Samson Properties

  (540) 596-5570

  1517 Brookdale Ct, Winchester, VA 22601
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  $349,900

  • Studio
  • 2,124 Sq Ft

  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

  (540) 351-9661

  619 S Cameron St, Winchester, VA 22601
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  /63

  $554,900

  • 4 Beds
  • 3 Baths
  • 3,118 Sq Ft

  303 Walker St, Winchester, VA 22601

  Welcome to this beautifully maintained 4-bedroom, 3-bathroom home on a prime corner lot in Whittier Acres! Located on a quiet cul-de-sac and just a short stroll to Whittier Park and the Museum of the Shenandoah Valley, this home offers both convenience and charm. The meticulously landscaped yard sets the tone for the care found throughout the property. Inside, you'll find refinished hardwood

  

  Frank Armstrong, IV

  Colony Realty

  (540) 501-6918

  303 Walker St, Winchester, VA 22601
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  /14

  $500,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 1,881 Sq Ft

  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

  (540) 253-4577

  331 Ridge Ave, Winchester, VA 22601
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  /48

  $679,900

  • 5 Beds
  • 4.5 Baths
  • 4,270 Sq Ft

  503 S Washington St, Winchester, VA 22601

  Discover unparalleled charm and historic elegance in this circa 1900 Victorian residence, ideally situated in Winchester's downtown Historic District and on the Apple Blossom parade route. Stunning 5-bedroom,4.5 bathroom home, boasting approximately 4270 sq ft of living space, invites you to experience the grandeur of a bygone era. Off-street parking.Key features include:Historic Charm: Original

  John Schroth Colony Realty

  503 S Washington St, Winchester, VA 22601
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  /50

  $470,000

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft

  350 Lanny Dr, Winchester, VA 22601

  This beautifully remodeled 3-bedroom, 2-bathroom all-brick rancher is perfectly situated in the heart of Winchester, providing easy access to schools, downtown, Winchester Medical Center, shopping, dining, entertainment, and parks. With its thoughtful remodel, this home blends timeless charm with modern updates. The eat-in kitchen boasts stainless steel appliances (2023), making it perfect for

  Sheila Pack RE/MAX Roots

  350 Lanny Dr, Winchester, VA 22601
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  $639,000 Open Sat 12PM - 2PM

  • 5 Beds
  • 4 Baths
  • 2,639 Sq Ft

  800 Kennedy Dr, Winchester, VA 22601

  Welcome to 800 Kennedy Drive, a spacious Colonial by Richmond American Homes located in the desirable Rolling Hills Estates. This home offers three finished levels with a smart, open layout—perfect for everyday living and entertaining. The main level flows seamlessly from room to room, featuring beautiful hardwood floors and fresh new carpet throughout. The large family room, featuring a stone

  Cindy Greenya Keller Williams Realty

  800 Kennedy Dr, Winchester, VA 22601
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  $545,000

  • 3 Beds
  • 2.5 Baths
  • 1,865 Sq Ft

  336 Miller St, Winchester, VA 22601

  This beautiful cottage, nestled on the very sought after Miller St, supplies the utmost convenience for what Winchester has to offer. From walking distance to eateries and Old Town entertainment, a quick drive to supermarkets all around and Handley High School just one street away! Supplying 3 bedrooms 2 1/2 bathrooms across three levels you can appreciate the character of an older home with

  Julie Teets Long & Foster Real Estate, Inc.

  336 Miller St, Winchester, VA 22601
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  $640,000

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

  320 Linden Dr, Winchester, VA 22601

  Experience 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 spacious gourmet kitchen with upgraded quartz countertops, and a gas

  Kimberly Schroeder Long & Foster Real Estate, Inc.

  320 Linden Dr, Winchester, VA 22601
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  $525,000 Open Sun 2PM - 3PM

  • 5 Beds
  • 2 Baths
  • 2,364 Sq Ft

  707 S Braddock St, Winchester, VA 22601

  Don’t miss your chance to own a Winchester classic in the heart of downtown! This beautifully renovated home boasts a brand-new kitchen with granite counters, stainless steel appliances, and white shaker cabinets. Enjoy modern bathrooms, stylish LVP flooring, and fresh paint throughout. The open-concept layout offers great flow for entertaining. Upstairs features spacious bedrooms and access to a

  Tolga Alper Real Broker, LLC

  707 S Braddock St, Winchester, VA 22601
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  $450,000 Open Fri 4PM - 6PM

  • 3 Beds
  • 2 Baths

  2824 Broadview St, Winchester, VA 22601

  Welcome to this stunningly new built 3-bedroom beautiful home located in the heart of Winchester. Enjoy the unbeatable convenience of being just moments from shopping Centers, playgrounds, theatres, and more.Step inside to experience the fresh scent of new construction and move-in-ready living, complete with brand new-flooring, modern appliances, and a thoughtfully designed layout perfect for

  Elizabeth Flood Keller Williams Realty

  2824 Broadview St, Winchester, VA 22601
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  /55

  $450,000

  • 5 Beds
  • 3.5 Baths
  • 3,333 Sq Ft

  1503 Valley Ave, Winchester, VA 22601

  Active again, Buyer's loan fell through. Charming Colonial located in the heart of Winchester. Only a few minutes walk to the Old Town Mall. This home features 5 bedrooms and 3 1/2 baths with 4 levels. There's a Primary Bedroom and Bathroom located on the main level with doors that open onto the back deck. The family room boasts hardwood floors and a wood burning fireplace. The kitchen is

  Julie Teets Long & Foster Real Estate, Inc.

  1503 Valley Ave, Winchester, VA 22601
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  $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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  /22

  $399,480 Open Sat 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,989 Sq Ft

  117 Boone Ct, Winchester, VA 22602

  Rossum Crossing is Winchester's newest and most popular townhome community, conveniently located near shopping and dining options.The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a pantry closet, and a

  Dick Bryan New Home Star Virginia, LLC

  117 Boone Ct, Winchester, VA 22602
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  /22

  $395,985 Open Sat 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,989 Sq Ft

  105 Boone Ct, Winchester, VA 22602

  Rossum Crossing is Winchester's newest and most popular townhome community, conveniently located near shopping and dining options.The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a pantry closet, and a

  Dick Bryan New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
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  /2

  $399,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft

  Bedford II, 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. 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

  Bedford II, Winchester, VA 22601
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  /2

  $452,539 New Construction

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

  Homesite 20 Monteith Dr, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage & Gourmet Kitchen! 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 for extra lighting located in the kitchen. You are

  DRB Homes

  Bedford II, Winchester, VA 22601
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  /2

  $429,340 New Construction

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

  Homesite 114 Monteith Dr, Winchester, VA 22601

  3 Level Townhome With Over 1,600 Finished Sq Ft & 1 Car Garage! Bedford II, 3 level townhome features a partial stone front with 1 car garage. This home features 3 Bedrooms and 3.5 Baths. It is fully finished top to bottom. The front door leads directly into the spacious lower level including 9 ft. ceilings, foyer with a double coat closet, access to the garage with a garage door opener.

  DRB Homes

  Bedford II, Winchester, VA 22601
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  /2

  $433,880 New Construction

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

  Homesite 117 Monteith Dr, Winchester, VA 22601

  3 Level End of Row Townhome With 1 Car Garage! 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 home. Separate pantry and LVP throughout the main level. The

  DRB Homes

  Bedford II, Winchester, VA 22601
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  $499,900 Open Sat 11AM - 1PM

  • 6 Beds
  • 3 Baths
  • 2,793 Sq Ft

  811 Berryville Ave, Winchester, VA 22601

  DO YOU HAVE A LARGE FAMILY AND NEED YOUR OWN SPACE. HERE IS 6 BEDROOMS 3 BATHROOMS WITH 3 FULL KITCHENS. ALMOST 2800 SQ. FT FINISHED. OFF STREET PARKING FOR 6 CARS. SHED AND STILL ROOM TO RELAX OUTBACK. MORE PICS COMING SOON.

  Richard Kozlowski Long & Foster Real Estate, Inc.

  811 Berryville Ave, Winchester, VA 22601
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  $379,900

  • 5 Beds
  • 2.5 Baths
  • 1,050 Sq Ft

  625 Butler Ave, Winchester, VA 22601

  This house has been remodeled and offers five bedrooms and 2.5 bathrooms. The open concept is evident in the easy-flowing floor plan. Beautiful kitchen quartz countertops, 42-inch cabinets and stainless steel appliances. Freshly painted, tastefully renovated bathrooms, new floors throughout, recess lighting, newer windows, driveway, and garage. Walkout basement with two big bedrooms and a

  Aracely Rivera First Decision Realty LLC

  625 Butler Ave, Winchester, VA 22601
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  /3

  $338,000

  • 3 Beds
  • 1.5 Baths
  • 1,197 Sq Ft

  421 Superior Ave, Winchester, VA 22601

  This home is part of an Estate and is being sold as is. Needs a little TLC. Great starter home.Perfectly situated just minutes from shopping, restaurants, and I-81, this property offers convenience without sacrificing its quaint charm. Don't miss out on this genuinely affordable opportunity. Give me a call today to make it yours!

  Cathy Caniford Crossroads, Realtors

  421 Superior Ave, Winchester, VA 22601
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  /5

  $150,000

  • Land
  • 0.16 Acre
  • $937,500 per Acre

  1415 Ramseur Ln, Winchester, VA 22601

  This 0.16-acre lot is a rare opportunity to own a homesite in the desirable Early’s Green at Meadowbranch subdivision, located in the heart of Winchester. Nestled within a beautifully maintained community, this property offers access to fantastic amenities including common grounds, a swimming pool, and tennis courts—perfect for enjoying an active and social lifestyle. Conveniently located near

  Sheila Pack RE/MAX Roots

  1415 Ramseur Ln, Winchester, VA 22601
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  $369,900

  • 3 Beds
  • 2.5 Baths
  • 2,132 Sq Ft

  211 Wood Ave, Winchester, VA 22601

  Charming Ranch-Style Home Near Winchester HospitalThis inviting ranch-style home is ready for you to make it your own! Ideally located near the hospital in the city of Winchester, it offers convenient main-level living with the added bonus of a fully finished basement. The spacious basement includes a full bathroom, a large recreation room, and a versatile bonus room—perfect for a home office or

  Paul Gallagher Colony Realty

  211 Wood Ave, Winchester, VA 22601
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  /4

  $399,000

  • 3 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  31 W Whitlock Ave, Winchester, VA 22601

  Wonderful location near Handley High School. Home has been updated and is ready for new owners! Professional photos will be done next week. Garage has been converted into studio. Large back yard that is fenced,. New deck!

  Meridee Powars Link Realty Services LLC

  31 W Whitlock Ave, Winchester, VA 22601
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  $739,000

  • 4 Beds
  • 3 Baths
  • 3,482 Sq Ft

  1419 Ramseur Ln, Winchester, VA 22601

  This beautifully maintained brick front rancher offers a spacious layout with 4 bedrooms and 3 full baths, situated in the desirable Early's Green at Meadowbranch community. Lot next door for sale $150K. Enjoy the comfort of single-level living with the added bonus of a finished basement with a professionally built bar—perfect for entertaining, hobbies, or extra living space. Hardwood flooring

  Sheila Pack RE/MAX Roots

  1419 Ramseur Ln, Winchester, VA 22601
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  $750,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 6 Baths
  • 3,824 Sq Ft

  504 Old Fort Rd, Winchester, VA 22601

  Handsome Colonial loaded with possibilities, from a multigenerational home to spacious entertaining venues. It features a Main Floor ensuite Bedroom and expansive finished basement with kitchenette and outside entrance for possible in-law suite. Inviting lot with large pool and covered and open decks in large privacy fenced back yard. Conveniently located in lovely, well-maintained

  Dallas Croft Samson Properties

  504 Old Fort Rd, Winchester, VA 22601
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  $399,900

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  509 W Cork St, Winchester, VA 22601

  Location, Location, Location! Nestled in the heart of Winchester on the sought-after west side, this recently renovated 3-bedroom, 1-bath home offers modern comforts with a touch of classic charm. Step inside to discover a brand-new kitchen featuring gleaming white cabinets and exquisite granite countertops, perfect for culinary enthusiasts. The updated bathroom boasts a stylish tiled tub,

  Dan Whitacre Colony Realty

  509 W Cork St, Winchester, VA 22601
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  /22

  $379,900

  • 2 Beds
  • 2 Baths
  • 1,442 Sq Ft

  1806 Kershaw Ln, Winchester, VA 22601

  Welcome to easy living at 1806 Kershaw Lane! This charming one-level home is perfectly situated in Winchester's desirable 55+ senior community of Willow Lawn Cottages, offering comfort, convenience, and a vibrant lifestyle. Step inside this meticulously maintained residence featuring two spacious bedrooms, two full bathrooms, hardwood floors & vaulted ceilings. The open and inviting floor plan

  Dan Whitacre Colony Realty

  1806 Kershaw Ln, Winchester, VA 22601
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  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  12 Montague Cir, Winchester, VA 22601

  Welcome to 12 Montague Circle — a recently updated 3-bedroom, 1.5-bath home tucked away in a quiet cul-de-sac in downtown Winchester. Enjoy the best of both worlds with a peaceful, private setting and immediate access to restaurants, shops, grocery stores, and all the charm the city has to offer. This recently renovated gem features a new roof and HVAC system, durable and modern LVP flooring, and

  Jon Fleming Weichert Realtors - Blue Ribbon

  12 Montague Cir, Winchester, VA 22601
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  $314,900

  • 4 Beds
  • 1 Bath
  • 1,340 Sq Ft

  21 W Pall Mall St, Winchester, VA 22601

  "Bring Your Vision To W Pall Mall" This 4 bedroom, 1 full bath home is perfect if you're looking for a renovation! Right in the heart of Winchester City within walking distance to the Old Town Walking Mall where you can enjoy excellent food, shopping and more! The first floor has a great sized living room, dining room and kitchen. 4 bedrooms on the upper level, full bathroom, walk-up attic and an

  Matt Kilmer EXP Realty, LLC

  21 W Pall Mall St, Winchester, VA 22601
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  /41

  $364,900

  • 3 Beds
  • 2 Baths
  • 1,727 Sq Ft

  512 Dunlap St, Winchester, VA 22601

  Conveniently located near Route 7 and I-81, this beautiful all-brick home offers easy access to everything Winchester has to offer. Situated in the heart of the city, you're just minutes from downtown, schools, shopping, Jim Barnett Park, and a variety of entertainment options. Inside, the main level features classic hardwood floors, a full bathroom, and a cozy wood-burning fireplace — perfect

  Sheila Pack RE/MAX Roots

  512 Dunlap St, Winchester, VA 22601
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  /34

  $595,995

  • 4 Beds
  • 3.5 Baths
  • 2,571 Sq Ft

  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 countertops,

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  720 Beehive Way, Winchester, VA 22601
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  /30

  $559,900

  • 3 Beds
  • 2 Baths
  • 2,154 Sq Ft

  1412 Magruder Ct, Winchester, VA 22601

  This peaceful property is within minutes of the Old Town Walking Mall, the arts of Shenandoah University , Winchester Little Theater, Museum of the Shenandoah Valley, Winchester Medical Center and shopping.Spacious living room/dining room with gas fireplace joins a sunroom opening to deck surrounded by lush landscaping. The kitchen features an inviting light filled breakfast area that looks

  Kathryn Hallett Long & Foster Real Estate, Inc.

  1412 Magruder Ct, Winchester, VA 22601
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  /13

  $235,000

  • Land
  • 0.36 Acre
  • $652,778 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  Introducing a newly configured Winchester City lot ready for you to build your dream home! The heavy lifting has already been done. The current owner worked with the neighbors and the City to widen the lot to accommodate a sizable home. With a width of approximately 100 feet you will have plenty of space to spread out. Located on a storied street in downtown Winchester, you will enjoy the perks

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  /20

  $233,000

  • 1 Bed
  • 1 Bath
  • 496 Sq Ft

  537 Hillman Dr, Winchester, VA 22601

  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 fixtures, and paint. Then I thought maybe I needed to dig deeper, so I installed an entirely new

  Kristin Crosby Samson Properties

  537 Hillman Dr, Winchester, VA 22601
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  /43

  $310,000

  • 3 Beds
  • 1.5 Baths
  • 1,299 Sq Ft

  341 Opequon Ave, Winchester, VA 22601

  Welcome home to this charming 3-bedroom, 1.5-bath gem perfectly located for easy access to I-81, Route 50, and Route 7—ideal for commuters. SEE VIDEO attached :)Enjoy the convenience of a main-level laundry room and peace of mind with a new roof installed in 2021. Step outside to your fully fenced backyard, complete with a screened-in porch and storage shed, perfect for relaxing or extra

  Sheila Pack RE/MAX Roots

  341 Opequon Ave, Winchester, VA 22601
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  /6

  $4,500,000

  • Land
  • 11 Acres
  • $393,701 per Acre

  801 Fairmont Ave, Winchester, VA 22601

  Unprecedented Development Opportunity, City of Winchester, 10.34 acres plus 3 SFH fronting Fairmont Ave (additional 1.09 acres). Gateway to downtown Old Town Winchester. Prime location for high density multifamily and mixed use commercial. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1 Main Street and Places

  Gillian Greenfield Coldwell Banker Premier

  801 Fairmont Ave, Winchester, VA 22601

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