Homes for Sale near The Independent School of Winchester

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  /81

  $1,224,000

  • 5 Beds
  • 5 Baths
  • 5,695 Sq Ft

  801 Armistead St, Winchester, VA 22601

  Step into refined elegance and exceptional quality in this beautifully upgraded residence, located in one of Winchester’s most desirable and walkable neighborhoods. This stately home offers the perfect blend of timeless architecture, sophisticated updates, and a lifestyle of convenience—just minutes from charming downtown shops, acclaimed restaurants, picturesque parks, and Winchester Medical

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  801 Armistead St, Winchester, VA 22601
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  /28

  $499,000

  • Studio
  • 2,736 Sq Ft

  386 Round Hill Rd, Winchester, VA 22602

  ATTENTION INVESTORS!! *** You will want to check out this fantastic opportunity - with a history of POSITIVE CASH FLOW these two ADJACENT PROPERTIES on a combined total of 1.91-acres in Winchester, just minutes from Valley Health Campus, shopping, restaurants and Rt. 37, may be what you are looking for! *** These two parcels are to be sold TOGETHER; they are not offered separately, and all for

  Bridget Aikens Colony Realty

  386 Round Hill Rd, Winchester, VA 22602
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  /20

  $349,988

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  425 Beechcroft Rd, Winchester, VA 22601

  Looking for a one level living in a sturdy, large brick rancher close to all amenities? This is it; walking distance to Frederick Douglas Elementary School. Restaurants, stores and amenities all within a couple of miles. Easy access to major commuter routes. Relax on the huge front porch or rear covered patio in the private, fully fenced backyard. Semi-open floor plan in the main area bracket

  Laurel Murray Samson Properties

  425 Beechcroft Rd, Winchester, VA 22601
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  /60

  $359,990

  • 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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  /31

  $305,000

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  7 E Hart St, Winchester, VA 22601

  Beautifully Maintained and Ideally Located!Nestled within city limits and just minutes from shopping, local dining, and the vibrant downtown walking mall, this home offers the perfect blend of comfort and convenience. Recent updates include fresh paint on all interior levels (2025), new carpet (2025), upgraded granite countertops (2019), a 30-year Timberline American Harvest roof (2017), HVAC

  Jennifer Sacco RE/MAX Roots

  7 E Hart St, Winchester, VA 22601
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  /62

  $765,000 Open Sun 11AM - 12PM

  • 4 Beds
  • 4.5 Baths
  • 5,183 Sq Ft

  1877 Clayton Ridge Dr, Winchester, VA 22601

  Nestled at the end of a quiet cul-de-sac and backing to serene wetlands and a protected preserve, this expansive colonial offers over 5,000 square feet of refined living space on nearly half an acre—providing both privacy and picturesque views. Boasting 4 generously sized bedrooms and 4.5 bathrooms, this home features a comfortable and functional main level layout perfect for everyday living and

  Dave Spence RE/MAX Roots

  1877 Clayton Ridge Dr, Winchester, VA 22601
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  /49

  $599,000

  • 5 Beds
  • 3 Baths
  • 3,200 Sq Ft

  1019 Berryville Ave, Winchester, VA 22601

  1019 Berryville Avenue, Winchester, VA 22601 is a Fully-rented triplex located just minutes from Old Town Winchester and Shenandoah University. This approximately 3,000 sq. ft. property is configured as three fully independent residential and commercial units. All units have private entrances, full kitchens, and separate electric. Middle unit may be used for commercial space. Units have been

  Pamela Debnam Houwzer, LLC

  1019 Berryville Ave, Winchester, VA 22601
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  /18

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,360 Sq Ft

  221 Boyd Ave, Winchester, VA 22601

  CHARMING HOME LOCATED CLOSE TO I-81 AND RT.7 HOME HAS 3 BEDROOMS WITH FULL BATH ON SECOND FLOOR AND HALF BATH ON FIRST. ADD YOUR PERSONAL TOUCHES AND MAKE THISA CUTE AND INVITING HOME. FRONT PORCH HAS BEEN GLASSED IN. PERFECT SPOT FOR YOUR MORNING COFFEE. **HOME BEING SOLD AS IS**

  Mary Hammond Jim Barb Realty Inc.

  221 Boyd Ave, Winchester, VA 22601
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  /28

  $314,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  946 Franklin St, Winchester, VA 22601

  Relax on the back decks overlooking a treed canopy yard. Cape code with fresh paint, laminate flooring , large walk-in closets on upper lever with sitting room and 1 bedroom plus attic storage. Main level has 2 bedrooms, bathroom, living room and kitchen with door to back decks and yard. Unfinished basement with plenty of room to expand and for storage. Home has NEW windows 2024, NEW roof 2022

  Stan Dull The Wiley Companies, Inc.

  946 Franklin St, Winchester, VA 22601
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  /14

  $339,900

  • 3 Beds
  • 1.5 Baths
  • 1,704 Sq Ft

  10 Richards Ave, Winchester, VA 22601

  Back on the market with updated baths and brand-new flooring in the enclosed porch! Welcome to this charming classic home located in the City of Winchester. Built in 1940, this home offers timeless appeal and craftsmanship. Inside, you'll find 3 bedrooms, 1.5 baths, and a versatile fourth room—ideal for a home office, guest room, or creative space. The main level greets you with a welcoming

  Lindsey Richardson ERA Oakcrest Realty, Inc.

  10 Richards Ave, Winchester, VA 22601
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  /69

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,189 Sq Ft

  1793 N Hayfield Rd, Winchester, VA 22603

  Charming all-brick ranch home on a spacious .97-acre lot, featuring 3 bedrooms, 2.5 baths, and traditional style throughout. Enjoy a covered front porch, rear deck, living room with fireplace, separate dining room, and eat-in kitchen. Includes a 2-car garage and no HOA. Ideally located—peaceful setting just outside of town, yet only 10 minutes to shopping and Winchester Medical Center, and just

  RoxAnn Grimes RE/MAX Roots

  1793 N Hayfield Rd, Winchester, VA 22603
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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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  /47

  $450,000

  • 3 Beds
  • 1.5 Baths
  • 1,952 Sq Ft

  164 Bethel Grange Rd, Winchester, VA 22603

  Beautiful brick ranch in a lovely rural setting with mountain views and only minutes to town amenities. 3 bedrooms, 1 1/2 baths with a shower stall in mud room downstairs. Country kitchen with adjoining carport. Large living room front window with nice view of Round Hill. Extra closets. 4 ft hallway with ceiling fan. 5x16 covered front porch and 1 car side carport. Paved drive and walkways.

  Cathy Durbin Crum Realty, Inc.

  164 Bethel Grange Rd, Winchester, VA 22603
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  /28

  $359,900

  • 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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  /37

  $389,000

  • 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! Great d downtown location where it is an easy walk to all the downtown shops and restaurants. . Garage has been converted into studio. Large back yard that is fenced,. Lots of new featues to include, HVAC, how water tank and deck!

  Meridee Powars Link Realty Services LLC

  31 W Whitlock Ave, Winchester, VA 22601
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  /59

  $724,900

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

  1419 Ramseur Ln, Winchester, VA 22601

  (Not a 55 community)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

  Sheila Pack RE/MAX Roots

  1419 Ramseur Ln, Winchester, VA 22601
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  /87

  $750,000

  • 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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  /27

  $369,000

  • 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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  /51

  $839,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 4 Baths
  • 3,612 Sq Ft

  373 Greenfield Dr, Winchester, VA 22603

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

  Jackie Douglass CENTURY 21 New Millennium

  373 Greenfield Dr, Winchester, VA 22603
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  /51

  $354,999

  • 3 Beds
  • 1 Bath
  • 1,445 Sq Ft

  671 Fox Dr, Winchester, VA 22603

  ESTATE SALE..... "owner's pride" this cozy Ranch well taken care of, PROPERTY OFFERS....separate laundry room with back door entry, 13x13 family room, dining room with patio door going out onto a 10x19 covered deck, one bevel living, beautiful hardwood floors throughout, cozy brick fireplace in living room, pull down attic for extra storage, fenced backyard with dusk-to-dawn pole light, garage

  Wanda Garris Miller Century 21 Redwood Realty

  671 Fox Dr, Winchester, VA 22603
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  /35

  $329,900

  • 4 Beds
  • 2 Baths
  • 2,304 Sq Ft

  911 Martinsburg Pike, Winchester, VA 22601

  Charming 1931 Home with Timeless Appeal & New Metal Roof – 911 Martinsburg Pike, WinchesterStep into a piece of Winchester history with this stunning "four-square" home, offering a perfect blend of old-world charm and modern convenience. Boasting 4 spacious bedrooms (5 if you make the main level room into a bedroom) and 2 full baths, including a main-level en suite, this home is designed for

  Sarah Abderrazzaq Realty ONE Group Old Towne

  911 Martinsburg Pike, Winchester, VA 22601
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  /48

  $299,900

  • 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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  /56

  $569,900

  • 4 Beds
  • 3 Baths
  • 3,998 Sq Ft

  419 Westside Station Dr, Winchester, VA 22601

  “Classic and Contemporary” - Welcome to this beautifully maintained contemporary home nestled in one of Winchester's most hidden but premium neighborhoods. Offering nearly 4,000 square feet of finished living space across three thoughtfully designed levels, this 4-bedroom, 3-bath residence combines stylish updates with unique architectural details. Step inside to discover a warm and inviting

  Mark Francis ICON Real Estate, LLC

  419 Westside Station Dr, Winchester, VA 22601
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  /53

  $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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  /24

  $360,000

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft

  2940 Grace St, Winchester, VA 22601

  Welcome to your charming Cape Cod retreat! Built in 1955, this delightful 3-bedroom, 1-bath home 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. --- Home is equipped with energy-efficient solar panels to help reduce

  Lauren Smith-Washbourne Coldwell Banker Premier

  2940 Grace St, Winchester, VA 22601
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  /40

  $374,500

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

  124 Wilkins Dr, Winchester, VA 22602

  Welcome home to this newly remodeled and upgraded ranch style home. All the convenience of one level living, with the option of a basement full of possibilities. Step into the spacious living room, complete with fireplace, as you walk in the front door. Continue through the wonderful flow of the house into the dining room and open kitchen. Enjoy making your meals in the fully renovated kitchen

  Dave Spence RE/MAX Roots

  124 Wilkins Dr, Winchester, VA 22602
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  /34

  $585,999

  • 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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  /17

  $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

  $224,900

  • 1 Bed
  • 1 Bath
  • 496 Sq Ft

  537 Hillman Dr, Winchester, VA 22601

  Update! Mandy is having more work done and will soon be connected to the city sewer system!! 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

  Kristin Crosby Samson Properties

  537 Hillman Dr, Winchester, VA 22601
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  /43

  $304,900

  • 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

  $4,000,000

  • Land
  • 27 Acres
  • $147,059 per Acre

  0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603

  Unprecedented Development Opportunity, County of Frederick, 27.2 acres in land use plan for high density rezoning (RP) and development (currently zoned RA, will require rezoning). Ideal townhouse and apartment project. Gateway to downtown Old Town Winchester. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1

  Gillian Greenfield Coldwell Banker Premier

  0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603
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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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  /41

  $319,900

  • 5 Beds
  • 2 Baths
  • 1,152 Sq Ft

  601 Grove St, Winchester, VA 22601

  601 Grove Street, is a single-family home offering a blend of comfort and convenience. Built in 1980, this 1,152 sq ft ranch-style residence features 3 bedrooms and 1 full bath on the main level, complemented by a partially finished basement that includes an additional bathroom and laundry area. The basement also offers versatile spaces that can serve as extra bedrooms, an office, or a recreation

  Lilly Triplett Colony Realty

  601 Grove St, Winchester, VA 22601
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  /37

  $450,000

  • 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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  /29

  $439,000

  • 5 Beds
  • 2 Baths
  • 2,186 Sq Ft

  214 S Braddock St, Winchester, VA 22601

  This property is currently zoned as fully commercial but has the potential to be changed to: Mixed Use or Fully Residential with proper city approval. Additional information from city located in documents. This home will need a Kitchen.Situated in Downtown Winchester, 214 S Braddock is waiting for your ideas! Built in 1865, this home features historic charm including exposed brick walls,

  Matt Leiva Keller Williams Realty

  214 S Braddock St, 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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  /67

  $850,000

  • 5 Beds
  • 4.5 Baths
  • 6,122 Sq Ft

  939 Buckner Dr, Winchester, VA 22601

  ***Accepting backup offers!!*** Listed Well Below Its True Worth! This fully brick home was built in 2000 in Meadow Branch and has been through extensive renovations and updates in 2023 & 2024. The main level bedroom includes a generous, newly updated ensuite with an oversized marble tiled shower & dual vanities. The ensuite also features a grand walk-in closet crafted by ClosetsByDesign. The

  Kiran K. Morzaria Parekh Redfin Corporation

  939 Buckner Dr, Winchester, VA 22601
• 

  

  /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
• 

  

  /22

  $355,000

  • 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
• 

  

  /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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