Winchester, VA Homes for Sale with Acreage

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  /11

  $1,499,000

  • Land
  • 2.45 Acres
  • $611,837 per Acre

  821,829,839, and 851 Fox Dr, Winchester, VA 22603

  Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

  

  Jim Shebest

  Coldwell Banker Realty

  (540) 530-3068

  821,829,839, and 851 Fox Dr, Winchester, VA 22603
• Explore Winchester

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  /9

  $1,300,000

  • Land
  • 64.91 Acres
  • $20,028 per Acre

  Lot 7 Cedar Creek Grade, Winchester, VA

  Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 7 Cedar Creek Grade, Winchester, VA
• 

  

  /2

  $195,000

  • 3 Beds
  • 1 Bath
  • 932 Sq Ft

  150 Cedar Grove Rd, Winchester, VA 22603

  This property is being sold strictly as-is, where-is. The mobile home on the property is believed to date back to the 1960s and is in need of significant renovation. Previous occupants began updating the home but did not complete the work. The property also features a garage-style building with a work bay and office space equipped with air conditioning, offering excellent potential for storage,

  

  Frank Armstrong, IV

  Colony Realty

  (540) 405-8678

  150 Cedar Grove Rd, Winchester, VA 22603
• 

  

  

  /65

  $799,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,331 Sq Ft

  123 Stetson St, Winchester, VA 22603

  Don’t miss this incredible opportunity to own a brand-new ranch home set on 2.66 beautiful acres, conveniently located near shopping and commuter routes to Winchester, Martinsburg, and Northern Virginia and approximately 10 minutes from the Winchester Medical Center. This thoughtfully designed home features an open-concept layout with a desirable split-bedroom design, offering both comfort and

  

  Brett Sowder

  RE/MAX Roots

  (540) 619-5465

  123 Stetson St, Winchester, VA 22603
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  /60

  $879,000

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  122 Broomsedge, Winchester, VA 22602

  Another quality home crafted by KEE Construction, located just off Cedar Creek Grade in the Shenandoah Valley and just minutes from Winchester City.Situated on 5.11 picturesque acres in a peaceful rural setting in the heart of the Shenandoah Valley, this modern farmhouse-style home with craftsman influences offers the perfect blend of refined craftsmanship and comfortable country living.

  Meridee Powars Link Realty Services LLC

  122 Broomsedge, Winchester, VA 22602
• 

  

  /73

  $799,000

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,256 Sq Ft

  201 Nathaniel Dr, Winchester, VA 22603

  Stunning new construction modern contemporary home situated on nearly 6 private wooded acres, offering the perfect balance of privacy and convenience. This thoughtfully designed home features an open-concept layout filled with abundant natural sunlight and beautiful wooded views throughout.The main living area showcases engineered hardwood flooring, a spacious living room and dining area, and

  Renee Waymire Samson Properties

  201 Nathaniel Dr, Winchester, VA 22603
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  /12

  $99,500

  • Land
  • 5.5 Acres
  • $18,091 per Acre

  0 Hodges Ln Unit LotWP012, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home, including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate

  0 Hodges Ln Unit LotWP012, Winchester, VA 22603
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  /14

  $104,500

  • Land
  • 5.5 Acres
  • $19,000 per Acre

  0 Hodges Ln Unit LotWP013, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home, including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate

  0 Hodges Ln Unit LotWP013, Winchester, VA 22603
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  /20

  $154,650

  • Land
  • 12.9 Acres
  • $11,988 per Acre

  0 Hodges Ln Unit LotWP011, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home, including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate

  0 Hodges Ln Unit LotWP011, Winchester, VA 22603
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  /44

  $315,000

  • Land
  • 20.96 Acres
  • $15,029 per Acre

  0 N Frederick Pike Unit LotWP001, Winchester, VA 22603

  Own a piece of beautiful Bloomingdale Farms, which hasnt been on the market since 1995. This land has been family-owned and operated for decades. Located just minutes northwest of Winchester near Lake Holiday. Featuring 800 ft +/- of road frontage on US-522 - North Frederick Pike securing the access. Also accessed by a 50 ft wide deeded access easement off US-522 - North Frederick Pike. The

  Chad Pangle Whitetail Properties Real Estate

  0 N Frederick Pike Unit LotWP001, Winchester, VA 22603
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  /45

  $528,575

  • Land
  • 84.57 Acres
  • $6,250 per Acre

  0 Brush Creek Rd Unit LotWP001, Winchester, VA 22603

  This land is located north of Winchester in the Cross Junction area of the county. Part of what was once a much larger family farm, and on the market for the first time since the 1950s. Access is secured via road frontage of nearly 2000 ft on paved and state-maintained Brush Creek Road, a terrific location for your next country home estate or recreational retreat. An electricity service line is

  Chad Pangle Whitetail Properties Real Estate

  0 Brush Creek Rd Unit LotWP001, Winchester, VA 22603
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  /19

  $141,500

  • Land
  • 11.1 Acres
  • $12,748 per Acre

  0 Hodges Ln Unit LotWP014, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home, including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate

  0 Hodges Ln Unit LotWP014, Winchester, VA 22603
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  /97

  $935,000

  • 4 Beds
  • 4 Baths
  • 4,545 Sq Ft

  620 Lake Serene Dr, Winchester, VA 22603

  Classic waterfront home, diligently updated and modernized with quality improvements and thoughtful design from well and septic and new floating dock on the outside, to totally renovated kitchen and primary bedroom suite and baths on the inside. Continue the seller's active lifestyle with the conveyance of a variety of boats and an indoor lap pool. Enjoy the seller's efforts to maintain this

  Dallas Croft Samson Properties

  620 Lake Serene Dr, Winchester, VA 22603
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  /91

  $1,195,000

  $55K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,188 Sq Ft

  1015 Redbud Rd, Winchester, VA 22603

  Set on over 10 private acres in the quiet Locust Level Estates community, this beautifully designed 4-bedroom, 4.5-bath ranch-style home offers the rare combination of peaceful country living without feeling isolated from everyday conveniences. Thoughtfully designed for comfortable main-level living, the home blends manageable luxury, functionality, and scenic countryside beauty, creating an

  Ryan Rice Keller Williams Capital Properties

  1015 Redbud Rd, Winchester, VA 22603
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  /79

  $1,130,000

  New Construction $70K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,211 Sq Ft

  00 Light Rd, Winchester, VA 22603

  Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning new construction nestled on twenty wooded and open acres with pleasant peaceful views. This thoughtfully designed home features spacious living areas, modern finishes, and a classic exterior that blends beautifully with its natural

  Melissa Johnston ERA Oakcrest Realty, Inc.

  00 Light Rd, Winchester, VA 22603
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  /109

  $1,150,000

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,880 Sq Ft

  199 Laurel Grove Rd, Winchester, VA 22602

  Nestled in the scenic countryside of Winchester, this impressive custom built home offers space, privacy, and beautiful Shenandoah Valley surroundings. Located in Frederick County, the property combines peaceful rural living with convenient access to shopping, dining, and commuter routes.Custom built in 2020, this spacious residence offers approximately 4,800+ square feet of living space on

  RoxAnn Grimes RE/MAX Roots

  199 Laurel Grove Rd, Winchester, VA 22602
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  /26

  $799,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  169 Cather Ln, Winchester, VA 22602

  Estimated completion August 2026. Photos shown are of a similar home previously constructed by the builder. Finishes and features may vary. Welcome to 169 Cather Lane, a spacious rancher situated on 5 beautiful pastoral acres with stunning views and an unbeatable location just minutes from town. Built by local builder Scott & Scott Construction, this home offers the perfect blend of quality

  Kaitlyn Behr Samson Properties

  169 Cather Ln, Winchester, VA 22602
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  /47

  $875,000

  • 4 Beds
  • 5.5 Baths
  • 5,054 Sq Ft

  125 Skyjes Ln, Winchester, VA 22602

  BACK ON THE MARKET! Custom-built modern farmhouse designed with comfort, flexibility, and multigenerational living in mind! This thoughtfully designed home, on 2 acres, welcomes you with an oversized family room featuring soaring 12-foot ceilings and an electric fireplace with a gas line already in place. A separate formal dining room with a stunning wall of windows creates the perfect setting

  Angie Bresnahan Pearson Smith Realty, LLC

  125 Skyjes Ln, Winchester, VA 22602
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  /42

  $780,000

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,476 Sq Ft

  230 Tranquil Wood Ln, Winchester, VA 22602

  Tucked away on over 3 private acres in the scenic countryside of Frederick County, this newly completed modern farmhouse offers peaceful country living with the convenience of nearby Winchester ammenities and major commuter routes. Custom built by Water Creek Homes, the home showcases quality craftsmanship, elevated finishes, and carefully curated details throughout. Designed to stand apart from

  Brittney Hunt Pearson Smith Realty LLC

  230 Tranquil Wood Ln, Winchester, VA 22602
• 

  

  /94

  $795,000

  • 5 Beds
  • 4 Baths
  • 4,075 Sq Ft

  274 Woodside Ln, Winchester, VA 22603

  Welcome to 274 Woodside - a secluded house on 5.06 acres with tons of storage! This 4,310 SF rambler style home has 2 masters (one up and one down), 4 bathrooms (2 on the main floor have heated floors), a huge kitchen with tons of cabinets, a large island with a 5 burner propane cooktop, and a pantry cabinet with pull-out shelves for storage, two fireplaces - one propane and one wood-burning

  Cindy Butler Virginia Property Group, Inc.

  274 Woodside Ln, Winchester, VA 22603
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  /8

  $760,000

  New Construction $15K PRICE INCREASE

  • 3 Beds
  • 3.5 Baths
  • 2,550 Sq Ft

  0 Tumble Leaf Ln, Winchester, VA 22602

  CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Dogwood model ( One Story Living ) with standard 10' main level ceilings and 13' ceilings in the Family Room. Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

  Daniel Boris Pearson Smith Realty, LLC

  0 Tumble Leaf Ln, Winchester, VA 22602
• 

  

  /79

  $850,000

  • 5 Beds
  • 5.5 Baths
  • 6,256 Sq Ft

  150 Ewell Dr, Winchester, VA 22602

  Welcome to Equestrian Estates, a highly sought-after Winchester community with no HOA, where space, style, and flexibility come together beautifully. This stately 5-bedroom, 6-bath Colonial offers over 6,700 square feet of finished living space on nearly 3 private acres, creating the perfect setting for both everyday living and entertaining. The home was not available for showings over the past

  Sherry Santmyer Hunt Country Sotheby's International Realty

  150 Ewell Dr, Winchester, VA 22602
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  /49

  $850,000

  New Construction

  • 5 Beds
  • 3 Baths
  • 3,057 Sq Ft

  Lot 5 Keval Gyan Way, Winchester, VA 22603

  Model available to see! Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of a large family

  Jim Thomson Realty ONE Group Old Towne

  Lot 5 Keval Gyan Way, Winchester, VA 22603
• 

  

  /42

  $749,900

  • 3 Beds
  • 3 Baths
  • 2,112 Sq Ft

  1049 Laurel Grove Rd, Winchester, VA 22602

  Discover the perfect blend of privacy, comfort, and natural beauty in this custom-built 3-bedroom, 3-bath retreat, set on a private, wooded lot with expansive mountain views. From the moment you arrive, the property feels like a peaceful getaway—quiet, scenic, and surrounded by nature—yet still just minutes from everyday conveniences. The main-level primary suite offers a true escape with its

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
• 

  

  /7

  $775,000

  New Construction $10K PRICE INCREASE

  • 4 Beds
  • 2.5 Baths
  • 3,150 Sq Ft

  0 Tumble Leaf Ln, Winchester, VA 22602

  CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Chestnut model with standard 10' Main Level Ceilings Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

  Daniel Boris Pearson Smith Realty, LLC

  0 Tumble Leaf Ln, Winchester, VA 22602
• 

  

  /7

  $135,000

  • Land
  • 5.06 Acres
  • $26,680 per Acre

  0 Back Mountain Rd Unit VAFV2041888, Winchester, VA 22602

  Discover a rare opportunity to own a stunning 5.06-acre parcel of land nestled in the serene embrace of the mountains. This exceptional lot offers a harmonious blend of natural beauty and convenience, making it the perfect canvas for your dream home or getaway retreat. Imagine waking up each morning to breathtaking mountain views that inspire tranquility and peace. The property is partly wooded,

  Laurie Hailey Charis Realty Group

  0 Back Mountain Rd Unit VAFV2041888, Winchester, VA 22602
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  /45

  $528,575

  • Land
  • 84.57 Acres
  • $6,250 per Acre

  0 Brush Creek Rd Unit VAFV2040676, Winchester, VA 22603

  This land is located north of Winchester in the Cross Junction area of the county. Part of what was once a much larger family farm and on the market for the first time since the 1950’s. Access is secured via road frontage of nearly 2000 ft on paved and state maintained Brush Creek Road. Terrific location for your next country home estate or recreational retreat. An electricity service line is

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Brush Creek Rd Unit VAFV2040676, Winchester, VA 22603
• 

  

  /58

  $589,900

  • 6 Beds
  • 4 Baths
  • 2,672 Sq Ft

  220 Snappy Ln, Winchester, VA 22602

  Stunning two-level home sits on a flat, picturesque 5-acres, with spacious 6-bedroom, 4-bathroom This single-family home offering about 2,672 sq ft of living space. The main level features a bright living room, a well-equipped kitchen with ample counter space, multiple dining areas, and generously sized bedrooms. A large deck provides easy outdoor access and is perfect for entertaining.The

  Mauricio Argandona Fairfax Realty Select

  220 Snappy Ln, Winchester, VA 22602
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  /6

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot B Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr Samson Properties

  Lot B Cather Ln, Winchester, VA 22602
• 

  

  /12

  $99,500

  • Land
  • 5.5 Acres
  • $18,091 per Acre

  0 Ln, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Ln, Winchester, VA 22603
• 

  

  /11

  $4,000,000

  • Land
  • 19 Acres
  • $210,526 per Acre

  368 Victory Rd, Winchester, VA 22602

  19 Acres, Prime Commercial or FLEX Development Opportunity! Zoned B2, General Commercial. Major commuter corridor to Northern VA, adjacent to Airport Business Park, FBI Records Center, Navy Federal Credit Union headquarters, and new One Logistics Park. Also #1 commuter route to Northern VA! Excellent visibility, flat topo, and dual access on Victory Lane and Independence! Sale includes 14.06

  Gillian Greenfield Coldwell Banker Premier

  368 Victory Rd, Winchester, VA 22602
• 

  

  /14

  $104,500

  • Land
  • 5.5 Acres
  • $19,000 per Acre

  0 Hodges Lot 13 Ln, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Hodges Lot 13 Ln, Winchester, VA 22603
• 

  

  /79

  $569,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,949 Sq Ft

  447 Plow Run Ln, Winchester, VA 22602

  Hello there... I’m going to be patiently waiting for the perfect new owners to call me home. Sitting on 2.73 beautiful acres, I’m a lovingly cared-for, like-new rancher with a warm heart, inviting spaces, and plenty of room to make memories for years to come. I’m still young and feel like I was just built yesterday.From the moment you step inside, I think you’ll notice how loved I’ve been. My

  Denise Bishop Long & Foster Real Estate, Inc.

  447 Plow Run Ln, Winchester, VA 22602
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  /27

  $239,900

  $40K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  111 Genesee Trail, Winchester, VA 22602

  Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painted with new luxury vinyl planking throughout the entire house. Brand new bathroom with tub /shower. Open floor plan with bedrooms on each end of the house for privacy. 2 sheds that convey to store whatever your heart desires. Come out and and enjoy all the open space! Go fishing ,play on the playground, kick

  Jacquelyn Rizzari MarketPlace REALTY

  111 Genesee Trail, Winchester, VA 22602
• 

  

  /51

  $1,595,000

  • Land
  • 158.44 Acres
  • $10,067 per Acre

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602

  Incredible opportunity to own 158.443 acres of pristine, private land in an exclusive 3-lot, 440-acre subdivision. This is the most secluded parcel of the three, offering unmatched 360-degree panoramic views and a level of privacy that’s increasingly rare—yet just 15 minutes from town. Tucked away from the lights and sounds of civilization, this property provides a peaceful, off-the-beaten-path

  Nadeem Helfer Samson Properties

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602
• 

  /2

  $42,500

  • Land
  • 5 Acres
  • $8,500 per Acre

  0 Winding Ridge Ln, Winchester, VA 22603

  5 acres beautiful wooded lot, with a hand-built stone building located just 30 minutes from downtown Winchester. See attached deed and plat. Property located close to 620 Winding Ridge Ln . See video andVirginia Department of Health records attached.

  Sheila Pack RE/MAX Roots

  0 Winding Ridge Ln, Winchester, VA 22603
• 

  

  /82

  $525,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,793 Sq Ft

  1239 Cedar Grove Rd, Winchester, VA 22603

  HUGE price improvement on this property! Sellers have found home of choice and are ready to move. Experience the perfect blend of historic artistry and modern convenience in this stunning 3-bedroom, 2-bath Craftsman-style retreat. Set on 3.27 sprawling, unrestricted acres, this property offers the rare freedom to create your own homestead, workshop, or private escape.The iconic front porch,

  Cynthia Lee RE/MAX Roots

  1239 Cedar Grove Rd, Winchester, VA 22603
• 

  

  /7

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot A Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr Samson Properties

  Lot A Cather Ln, Winchester, VA 22602
• 

  

  /53

  $650,000

  • 3 Beds
  • 4 Baths
  • 3,352 Sq Ft

  350 Plow Run Ln, Winchester, VA 22602

  Nestled on 2 beautiful acres in Frederick County, Virginia, this stunning ranch-style home offers the rare combination of peaceful country living with Comcast/Xfinity high-speed internet and cable TV — all just minutes from downtown Winchester! Custom built by a respected local builder and meticulously maintained, this home is loaded with quality finishes, functional space, and exceptional charm

  Leah Clowser RE/MAX Roots

  350 Plow Run Ln, Winchester, VA 22602
• 

  

  /52

  $525,000

  • 3 Beds
  • 1 Bath
  • 1,370 Sq Ft

  1310 Siler Rd, Winchester, VA 22603

  Come and see this serene, wooded, hilltop retreat, just minutes west of Winchester. This fully updated 3 BR, 1 BA Brick Rambler is situated on a private, unrestricted 10-acre wooded lot with great views. This home has a covered front porch and an 18-by-30-foot concrete patio in the back, perfect for entertaining. The brick Fireplace has a wood-burning stove insert. This home has been fully

  Marcia Coss Weichert, REALTORS

  1310 Siler Rd, Winchester, VA 22603

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