Winchester, VA Homes for Sale

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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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  /9

  $135,000

  • 1 Bed
  • 1 Bath

  1114 Cedar Grove Rd, Winchester, VA 22603

  Property has a great location but is probably a tear down. Health Documents available showing location of well/septic.

  Dave Spence RE/MAX Roots

  1114 Cedar Grove Rd, Winchester, VA 22603
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  /24

  $99,900

  • Land
  • 0.50 Acre
  • $199,800 per Acre

  336 Old Bethel Church Rd, Winchester, VA 22603

  Real value is in the well and septic. 1964 Mobile home (original) is in poor condition and most likely needs replaced. The 1/2 acre lot should be grandfathered in but a Variance will be required through Frederick County to adjust setbacks in order to build, replace with a mobile or potentially a doublewide. (3BD septic installed in 1966). Pretty area of the County; only minutes to Winchester

  Edward Beightol Cedar Creek Real Estate

  336 Old Bethel Church Rd, Winchester, VA 22603
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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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  /34

  $307,000 Open Sat 2PM - 4PM

  • 3 Beds
  • 1.5 Baths
  • 1,488 Sq Ft

  104 Seabreeze Ln, Winchester, VA 22602

  Spacious three level townhome. Property backs to wooded area for privacy. Minutes to Rt. 7 & I-81 corridor. Community swimming pool. Nice deck for grilling out, or take in the sounds of nature. Basement can be improved with another bath and bedroom and family room. Room to add square footage. All rooms are very spacious. Primary suite has a walk-in closet. Owner has painted the home. Move in

  Wanda Himes The Himes Group, LLC

  104 Seabreeze Ln, Winchester, VA 22602
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  /42

  $200,000

  • 3 Beds
  • 1 Bath
  • 775 Sq Ft

  117 Miller Rd, Winchester, VA 22602

  Welcome to 117 Miller Rd—your chance to own a hidden gem in one of Frederick County’s most historic and picturesque settings. Nestled on a beautiful, flat, and cleared 1-acre lot, this property is just minutes from downtown Winchester and less than 4 miles down Cedar Creek Grade. Tucked beside the Opequon Historic District—home to some of the area’s earliest settlements—you’ll be surrounded by

  Kaitlyn Behr RE/MAX Roots

  117 Miller Rd, Winchester, VA 22602
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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
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  /4

  $229,000

  • 2 Beds
  • 1 Bath
  • 894 Sq Ft

  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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  /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

  $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
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  /51

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  545 Deer Run Dr, Winchester, VA 22602

  BACK ON THE MARKET AT NO FAULT OF THE SELLER! BUYER'S FINANCING FELL THROUGH! Peaceful Country Living on Three Secluded Acres – Just Minutes from Downtown WinchesterWelcome to 545 Deer Run, where privacy, charm, and convenience come together. Nestled on three acres, this warm and welcoming home offers a serene escape from the everyday—yet it’s only minutes from the restaurants, shops, and

  Kaaren Lofgren Corcoran McEnearney

  545 Deer Run Dr, Winchester, VA 22602
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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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  /22

  $369,900

  • 4 Beds
  • 2 Baths
  • 1,607 Sq Ft

  148 Amoco Ln, Winchester, VA 22603

  RENOVATIONS JUST COMPLETED ON 06/01/25! Frederick County B2 zoning on over 1/2 acre. Located just off Interstate 81 and Rt 11, Martinsburg Pike. Main level is 1,142 sq ft with two bedrooms and a walk-in shower in bathroom. Upper level has 465 sq ft with 2 bedrooms and a full bath = 1,607 total sq ft of living area. Plus a full basement. One car carport with additional storage area. NO HOA.

  Leo Smith CENTURY 21 New Millennium

  148 Amoco Ln, Winchester, VA 22603
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  /60

  $660,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,165 Sq Ft

  109 Aulee Ct, Winchester, VA 22602

  If you’re looking for a home that truly checks all the boxes—space, setting, style, and room to grow—this is the one you’ve been waiting for. Perfectly perched on a quiet cul-de-sac in the sought-after Twin Lakes Overlook neighborhood, this Toll Brothers built beauty offers more than just curb appeal. It boasts a premium lot backing to the lake, with tranquil views that might just make you forget

  Kim Spear Keller Williams Realty

  109 Aulee Ct, Winchester, VA 22602
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  /23

  $99,900

  • Land
  • 16 Acres
  • $6,283 per Acre

  LOT 11-HOOVER MTN Pack Horse Rd, Winchester, VA 22603

  Unique property, great for recreation. Land is all wooded, tall hardwoods, mostly mountainside. There is about 1.5 acres where Little Mountain Run (creek) runs through the property for over 300' so that you have a very flat, wooded area on the other side of the creek which is perfect for hiking, camping, hunting. You will have to visit the property to really appreciate what it has to offer.

  Edward Beightol Cedar Creek Real Estate

  LOT 11-HOOVER MTN Pack Horse Rd, Winchester, VA 22603
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  /42

  $349,000

  • 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

  $292,500

  • 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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  /94

  $1,125,000

  • 4 Beds
  • 4 Baths
  • 4,949 Sq Ft

  1460 Pitcock Ln, Winchester, VA 22602

  This beauty includes three lots totaling 27.65 acres and only 10 minutes from Winchester City! This home exudes character from the moment you step in!Located in a secluded area with towering trees and a pond. This charming log cabin was moved to its current site in circa 1960, with a three-story addition built in 1994. The main cabin features exposed wooden beams and a cozy fireplace, offering

  Sheila Pack RE/MAX Roots

  1460 Pitcock Ln, Winchester, VA 22602
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  /58

  $364,990

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

  1005 Pennsylvania Ave, Winchester, VA 22601

  The price has just been reduced! 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

  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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  /49

  $615,000

  • 4 Beds
  • 2.5 Baths
  • 3,106 Sq Ft

  135 Oak Ridge Ln, Winchester, VA 22602

  Welcome to Fairway Estates Living! Tucked away on a quiet cul-de-sac in one of Winchester’s most coveted (and HOA-free!) neighborhoods, this stately 4-bedroom, 2.5-bath Colonial is ready for owners who will love it as much as the last ones did! This location is just around the corner from Winchester Country Club, commuter routes via Senseny Rd, and everything in town—groceries, shops,

  Sarah Abderrazzaq Realty ONE Group Old Towne

  135 Oak Ridge Ln, Winchester, VA 22602
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  /104

  $1,115,000

  • 5 Beds
  • 7 Baths
  • 5,058 Sq Ft

  700 Miller Rd, Winchester, VA 22602

  Nestled in a highly desirable area, this stunning Colonial home offers timeless elegance on 2.5 private acres. Thoughtfully designed with both a main-level primary suite and an upper-level primary suite, this home provides flexible living options for modern convenience. Spacious and filled with natural light, the home features a welcoming foyer, a beautiful kitchen, and multiple living and

  Lilly Triplett Colony Realty

  700 Miller Rd, Winchester, VA 22602
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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

  $250,000

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

  910 Franklin St, Winchester, VA 22601

  PRICE RARE UNIQUE OPPORTUNITY KNOCKS!50K 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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  /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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  /75

  $599,999

  • 4 Beds
  • 3.5 Baths
  • 3,084 Sq Ft

  1425 Cedar Grove Rd, Winchester, VA 22603

  Welcome to this spacious colonial situated on 4.75 acres in Winchester. With 4 bedrooms and 3.5 bathrooms, this home offers plenty of room and modern comforts. Key Updates:New Roof (2023) – Enjoy peace of mind with this recent upgrade.Brand New HVAC System – Featuring highly efficient heat pumps with a 90% efficiency rating.New Bosch Dishwasher – It's so quiet - no disruption while you're taking

  Katrina Smith RE/MAX Roots

  1425 Cedar Grove Rd, Winchester, VA 22603
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  /61

  $825,000

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  400 Great Mountain Ln, Winchester, VA 22602

  Please watch the Video! Escape to your own private mountain retreat with this stunning custom-built log home, offering breathtaking views of the Shenandoah Valley from an elevation of 1600 feet and 99+ acres of pristine land (elevation 2300+). Explore trails illuminated by solarlights—perfect for hiking,riding, and outdoor adventures. For shooting enthusiasts, a private range awaits, while an

  Leah Clowser RE/MAX Roots

  400 Great Mountain Ln, Winchester, VA 22602
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  /53

  $394,900

  • 3 Beds
  • 2 Baths
  • 1,953 Sq Ft

  123 Meadowbrooke Place, Winchester, VA 22602

  This charming rambler is the one you've been looking for! Located at the end of a cul-de-sac on a tree-lined street, this property offers plenty of privacy. Inside you are greeted by a spacious open floor plan, featuring hardwood floors in all of the rooms except the kitchen and bathrooms. The kitchen features an abundance of wood cabinetry, newer SS dishwasher, stove and refrigerator and new

  Heloisa Amar Samson Properties

  123 Meadowbrooke Place, Winchester, VA 22602
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  /76

  $624,500

  • 5 Beds
  • 4 Baths
  • 3,086 Sq Ft

  121 Carnmore Dr, Winchester, VA 22602

  Welcome to 121 Carnmore Drive located in Ravenwing Subdivision on Winchester's ultra-convenient east side. This 5 bedroom/4 full bath home will check everything on your MUST HAVE list. Feel welcomed into the gracious entryway with soaring ceilings and generous living & dining rooms to greet you. Sunny windows stream natural light. Gleaming wood floors move from entry to heart of the home.

  Angela Duncan MarketPlace REALTY

  121 Carnmore Dr, Winchester, VA 22602
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  /74

  $679,000

  • 4 Beds
  • 3.5 Baths
  • 3,008 Sq Ft

  355 Fishel Rd, Winchester, VA 22602

  Experience the epitome of homeownership with this stunning colonial home property perfectly set on 2.5+ acres of serene land just moments from all the conveniences of town. Offering the perfect blend of classic charm and modern amenities, this home is ideal for those seeking privacy without sacrificing accessibility. Thoughtfully designed with generous living spaces. Upon entering, you're greeted

  Daniel Brereton RE/MAX Roots

  355 Fishel Rd, Winchester, VA 22602
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  /38

  $455,000

  • 4 Beds
  • 3.5 Baths
  • 2,892 Sq Ft

  112 Hites St, Winchester, VA 22602

  A Cape Cod like no other! This home boasts over 2800 sq.ft (addition in 2011), which includes two primary suites! The spacious main level features hardwood floors in the entryway, living room and dining room and is adorned by beautiful crown molding throughout. The kitchen features white cabinetry and SS appliances. A main level primary suite features hardwood floors and an attached bathroom,

  Heloisa Amar Samson Properties

  112 Hites St, Winchester, VA 22602
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  /9

  $186,000

  • Land
  • 60 Acres
  • $3,104 per Acre

  0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602

  UNIQUE 60 ACRE WOODED TRACT within the Great North Mountain Wilderness Area enhanced by County maintained hard surfaced road access and available electricity. The Offering also includes a contiguous half acre building Lot (Shawneeland - Tax ID 49-A05-1-W-1) which is located adjacent to the main tracts access point at the intersection of Tomahawk and Jalapa. Potential forty plus mile views

  Wayne Wilson Thomas and Talbot Estate Properties, Inc.

  0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602
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  /40

  $415,000

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft

  128 Pioneers Rd, Winchester, VA 22602

  The previous contract was released through no fault of the seller. Great house in an excellent location just minutes from commuter routes and downtown Winchester. There are many recent improvements and upgrades to the kitchen and bathrooms. The bedrooms and living areas are nicely proportioned for comfortable living. Wonderful gas fireplace in the living room makes a beautiful focal point. This

  Erika De Azagra ERA Oakcrest Realty, Inc.

  128 Pioneers Rd, Winchester, VA 22602
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  /63

  $349,900

  • 3 Beds
  • 2.5 Baths
  • 1,362 Sq Ft

  525 Pheasant Dr, Winchester, VA 22602

  Absolutely beautiful home. When you walk into this lovely home, with its many upgraded fixtures, and freshly painted walls you will realize there is nothing you need to do but relax and enjoy your new home. Three bedrooms, 2 1/2 bathrooms and a gourmet kitchen with stainless steel appliances. Primary bedroom has two closets, one is a walk-in, and a private bathroom. French doors leading to a

  Jimmy Biedrzycki CENTURY 21 New Millennium

  525 Pheasant Dr, Winchester, VA 22602
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  /23

  $168,000

  • Land
  • 10 Acres
  • $16,800 per Acre

  0 Gough Rd Unit VAFV2033030, Winchester, VA 22602

  Enjoy rural living and fun on this building lot in the Long Ridge Estates community. This prime building lot is located off of Gough Road in the High View Manor area of the county. This parcel has a septic certification letter on record with the county health department for a 4 bedroom septic system. Access is secured via a 50 ft deeded access easement which has already been installed and

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Gough Rd Unit VAFV2033030, Winchester, VA 22602
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  /12

  $22,500

  • Land
  • 0.29 Acre
  • $77,586 per Acre

  155 Hawk Trail, Winchester, VA 22602

  Lot 155 on Hawk Trail , is located in the mountainous residential community of Shawneeland, just 12 miles from Winchester, VA. Enjoy the fresh mountain air, hiking, fishing and swimming in Lake Cherokee in this idyllic setting. Know, however, that you are close to Winchester Medical Center, the Museum of the Shenandoah Valley, and an abundance of restaurants and shopping opportunities. Build a

  Rebecca McTavish Long & Foster Real Estate, Inc.

  155 Hawk Trail, Winchester, VA 22602
• 

  

  /40

  $379,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  112 Fairway Dr, Winchester, VA 22602

  New roof just installed!This beautiful ranch-style home is located in a quiet cul-de-sac just minutes from downtown Winchester, Jim Barnett Park, and Shenandoah University. Ideal for commuters, with easy access to Route 7 and I-81.The home features 3 bedrooms and 1 bathroom, with a full, partially finished basement adding 600 sq ft of finished space. A convenient basement kitchenette is perfect

  Daniel Brereton RE/MAX Roots

  112 Fairway Dr, Winchester, VA 22602
• 

  

  /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
• 

  

  /72

  $674,900

  • 4 Beds
  • 4.5 Baths
  • 4,395 Sq Ft

  113 Pangborne Ct, Winchester, VA 22602

  INCREDIBLE VALUE AND NEW PRICE! Space, space and more space! With nearly 4,400 finished square feet, this home can accommodate the needs of any buyer! Sitting on a quiet cul de sac on the desirable east side of Winchester, the location is ideal for commuters to NOVA as well as provides easy access to I-81. The spacious main floor offers a living room, formal dining room, study, family room,

  Stephanie Ryall Realty ONE Group Old Towne

  113 Pangborne Ct, Winchester, VA 22602
• 

  

  /50

  $429,000

  • 4 Beds
  • 3 Baths
  • 1,617 Sq Ft

  126 Armstrong Place, Winchester, VA 22602

  All brick ranch home with 4 bedrooms close to town and a short walk to the golf course! Main level large living Room and dinning room, 2 bedrooms and 2 bathrooms, an eat in kitchen, has gleaming hardwood flooring. Lower Level large area for pool table 2 more bedrooms, 1 bathroom and a family room equipped with a brick fireplace and space for a pool table. There is a sliding glass door that leads

  John Scully Colony Realty

  126 Armstrong Place, Winchester, VA 22602

Showing Results 121 - 160, Page 4 of 8