Winchester, VA Homes for Sale under $300,000

• 

  

  /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

  150 Cedar Grove Rd, Winchester, VA 22603
• Explore Winchester

• 

  

  /2

  $175,000

  • Land
  • 16,117 Sq Ft
  • $472,973 per Acre

  719 Kennedy Dr, Winchester, VA 22601

  Vacant Lot in Rolling HillsOne of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer

  

  Frank Armstrong, IV

  Colony Realty

  719 Kennedy Dr, Winchester, VA 22601
• 

  

  

  /17

  $125,000

  • 1 Bed
  • 1 Bath
  • 624 Sq Ft

  415 Puma Trail, Winchester, VA 22602

  Ranch cabin-style home nestled in the woods on a private 1⁄2-acre lot. Featuring 1-bedroom, additional room but not technically a bedroom, and 1 full bath, this property offers endless potential as a full-time residence, weekend retreat, or investment opportunity. Enjoy the tranquility of the wooded surroundings while remaining conveniently located just 25 minutes from Winchester. The home is

  

  Ken Evans

  RE/MAX Real Estate Connections

  415 Puma Trail, Winchester, VA 22602
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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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  /23

  $127,750

  • Land
  • 8.11 Acres
  • $15,752 per Acre

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602

  Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by, making for easy

  Chad Pangle Whitetail Properties Real Estate

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602
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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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  /22

  $269,000

  • Land
  • 42,253 Sq Ft
  • $277,320 per Acre

  823 Armistead St, Winchester, VA 22601

  *** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

  Janet Flaherty Keller Williams Realty

  823 Armistead St, Winchester, VA 22601
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  /2

  $215,000

  • Land
  • 26,571 Sq Ft
  • $352,459 per Acre

  40 Huntersridge Rd, Winchester, VA 22602

  A rare offering in the established Oakdale Crossing Community. This 0.61 acre-lot boasts a flat topography, tucked on a quiet cul-de-sac, and framed with large lush trees. Enjoy the perfect blend of seclusion and proximity with a short drive to the Winchester Country Club, Jim Barnett Park, Major shopping & dining, and the downtown walking mall. + prime location for commuters with easy access to

  Jocelyn Tweedie Hunt Country Sotheby's International Realty

  40 Huntersridge Rd, 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
• 

  

  /17

  $240,000

  • 2 Beds
  • 1 Bath
  • 997 Sq Ft

  187 Valley Mill Rd, Winchester, VA 22602

  Great investment opportunity for this centrally located rambler! Just minutes from Route 7 and I-81, this property offers convenient access to shopping, restaurants, and everyday amenities.The current tenant is under lease through 11/13/26, providing immediate rental income for an investor. With some sweat equity and a few updates, there is potential to increase the rental income

  Heloisa Amar Samson Properties

  187 Valley Mill Rd, Winchester, VA 22602
• 

  

  /15

  $89,000

  • Land
  • 6.11 Acres
  • $14,566 per Acre

  0 Pack Horse Road Lot A Unit VAFV2042702, Winchester, VA 22603

  The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 6.11 lot A is wooded, has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a homestead, simple get away to enjoy quiet and tranquility, and/or the new

  Dave Spence RE/MAX Roots

  0 Pack Horse Road Lot A Unit VAFV2042702, Winchester, VA 22603
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  /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
• 

  

  /15

  $110,000

  • Land
  • 6.42 Acres
  • $17,134 per Acre

  0 Pack Horse Road Lot C Unit VAFV2042708, Winchester, VA 22603

  The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 6.42 lot C is wooded, has septic already installed, has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a homestead, simple get away to enjoy quiet

  Dave Spence RE/MAX Roots

  0 Pack Horse Road Lot C Unit VAFV2042708, Winchester, VA 22603
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  /32

  $279,000

  • 2 Beds
  • 1.5 Baths
  • 1,590 Sq Ft

  261 Waterford Ln, Winchester, VA 22602

  Move-in ready and well maintained! This charming 2-bedroom, 1.5-bath townhome offers comfortable living with a spacious main-level living area, eat-in kitchen, and convenient laundry. The partially finished basement adds a large family room and plenty of storage, with walk-out access to a shaded patio and large, private fenced backyard. Relax on the back deck surrounded by mature trees, offering

  Liz Rutherford ERA Oakcrest Realty, Inc.

  261 Waterford Ln, Winchester, VA 22602
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  /6

  $20,000

  • Land
  • 20,037 Sq Ft
  • $43,478 per Acre

  Lot 102 Bow Wood Trail, Winchester, VA 22602

  A Hidden Gem Waiting for YouNestled in the serene countryside of Winchester, Virginia, lies a great treed building lot on the lower side of Shawneeland. This picturesque piece of land offers the perfect blend of seclusion and convenience, making it an ideal location for building your dream home.Enjoy the tranquility and natural beauty of Shawneeland's private parks, perfect for relaxing

  Rick Guthrie Keller Williams Realty

  Lot 102 Bow Wood Trail, Winchester, VA 22602
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  /5

  $295,000

  Coming Soon Sep 12

  • 3 Beds
  • 1 Bath
  • 913 Sq Ft

  405 Shenandoah Ave, Winchester, VA 22601

  Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality.The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and

  Heloisa Amar Samson Properties

  405 Shenandoah Ave, Winchester, VA 22601
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  /5

  $89,000

  • Land
  • 40,075 Sq Ft
  • $96,739 per Acre

  Lot 14A Timber Ridge Trail, Winchester, VA 22602

  Enjoy Stunning Sunsets and Endless Sky on This Nearly One-Acre Lot! Imagine unwinding every evening with spectacular sunsets glowing across the valley—the back of this beautiful lot faces northwest, perfect for soaking in nature’s spectacular evening show. Located just 30 minutes from downtown Winchester, this serene oasis offers the ideal blend of peaceful country living and convenient city

  Kristin Crosby Samson Properties

  Lot 14A Timber Ridge Trail, Winchester, VA 22602
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  /9

  $30,000

  • Land
  • 1.03 Acres
  • $29,126 per Acre

  440 Mountain Falls, Winchester, VA 22602

  Here's your chance to own a little over 1 ACRE(1.03) of Peaceful Land in WILDE ACRES! This LOT is ready for your Dream Home! Situated close to the entrance of the community, You will be delighted to see that the land has been partially cleared, a widened entrance, trees added in front for added privacy, and an Approved 3 bedroom septic perc. Enjoy the quiet space, wild life, and room to spread

  Jodi Costello ERA Oakcrest Realty, Inc.

  440 Mountain Falls, Winchester, VA 22602
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  /15

  $49,900

  • Land
  • 3 Acres
  • $16,633 per Acre

  0 0 Henry Dr, Winchester, VA 22602

  "Build Your Home On Henry" This beautiful 3-Acre lot is located in Mountain Falls Park. With mature trees you can enjoy your privacy. Enjoy the community lake, common area, playground and picnic area! Has a 3-bedroom perc. Bring your vision to life!

  Matt Kilmer Samson Properties

  0 0 Henry Dr, Winchester, VA 22602
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  /6

  $40,000

  $10K PRICE DROP

  • Land
  • 1.38 Acres
  • $28,986 per Acre

  105 Arum Trail, Winchester, VA 22602

  Welcome to your buildable, oversized 1.38 acre lot in Duck Run. Ready for your forever home? Come check this property out! No utilities on property. Blank slate ready for all your design ideas.

  Cat Haines Cedar Creek Real Estate

  105 Arum Trail, Winchester, VA 22602
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  /33

  $300,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018.

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /21

  $210,000

  • Land
  • 5 Acres
  • $42,000 per Acre

  0 Off of Mount Olive Rd Unit VAFV2044302, Winchester, VA 22603

  Prime building lot conveniently located less than 10 minutes west of Winchester with immediate access to US-50 - Northwestern Pike. Part of what was once the well known Rotz Farm and now part of the brand new Ridgeview Glen community. This land is ideally positioned between scenic Flint Ridge and flowing Hogue Creek. This tract features a 4 bedroom septic certification letter which is already on

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Off of Mount Olive Rd Unit VAFV2044302, Winchester, VA 22603
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  /4

  $74,000

  • Land
  • 40,510 Sq Ft
  • $79,570 per Acre

  Lot 315A Timber Ridge Trail, Winchester, VA 22602

  Rare Double Lot – Nearly One Acre of Prime Ridge Top Privacy in Shawneeland! This exceptional, nearly one-acre, double lot offers a perfect blend of privacy and potential - and is ready for you to build the home of your dreams! Nestled atop the ridge in Shawneeland, this wooded parcel has been perc’d and approved for a three-bedroom septic system, with a certification letter on file with the

  Kristin Crosby Samson Properties

  Lot 315A Timber Ridge Trail, Winchester, VA 22602
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  /17

  $199,900

  $15K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $555,278 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  /42

  $175,000

  • 1 Bed
  • 1 Bath
  • 384 Sq Ft

  305 Raccoon Dr, Winchester, VA 22602

  Cozy 1-bedroom, 1-bathroom cabin located on a level, nicely shaded lot, ready for your enjoyment. Offering the perfect combination of rustic character, comfort, and natural beauty. Step outside onto the screened-in porch and enjoy your morning coffee, unwind with a good book, or simply take in the sights and sounds of the surrounding woods. This peaceful setting offers a wonderful opportunity to

  Bill Dixon Dandridge Realty Group, LLC

  305 Raccoon Dr, Winchester, VA 22602
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  /22

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  452 Valley Mill Rd, Winchester, VA 22602

  SOLD AS IS, CASH ONLY! Investor special on this great home that is on .55 Acre lot (2 lots make this up). Outbuildings, wood floors, fireplace, 3 generous size bedrooms, laundry room, eat in kitchen and dining room. Home needs to be hooked up to county water, current well not working properly. Call for details.

  Deborah Matthews ERA Oakcrest Realty, Inc.

  452 Valley Mill Rd, Winchester, VA 22602
• 

  

  /18

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  132 Geronimo Trail, Winchester, VA 22602

  Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet and highly desirable neighborhood, this charming single-family home is perfect for first-time buyers, downsizers, or anyone seeking a peaceful retreat. This 1,232 square-foot rancher features 3 bedrooms, 2 full bathrooms, eat-in kitchen, living room, a brick fireplace with highly a efficient wood-burning

  Shane Price Long & Foster Real Estate, Inc.

  132 Geronimo Trail, Winchester, VA 22602
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  /2

  $139,900

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  130 Wollaston Dr Unit A34, Winchester, VA 22603

  COMING SOON! Currently under construction. Welcome to Regency Lakes, an all age active and vibrant community, where your dream home is coming to life. We are excited to offer a brand new, 2026 3 bed, 2 bath home for sale, featuring approximately 1564.80 sq ft of thoughtfully designed living space. Located in Winchester, this soon-to-be-completed property will offer the perfect blend of modern

  Kristina Kelly Regency Lakes

  130 Wollaston Dr Unit A34, Winchester, VA 22603
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  /12

  $17,000

  • Land
  • 16,552 Sq Ft
  • $44,737 per Acre

  Lot 231 Timber Ridge, Winchester, VA 22602

  This lot is located in the Shawneeland community of northwestern Frederick County, Virginia on the western-facing slope of Great North Mountain. Level and partially treed, it's a spectacular place to build your weekend getaway cabin or year-round home. Swim in Shawneeland's spring-fed lake, fish, hike, and picnic, or simply enjoy the quiet beauty of nature. Located just 12 miles from

  Rebecca McTavish Long & Foster Real Estate, Inc.

  Lot 231 Timber Ridge, Winchester, VA 22602
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  /5

  $22,500

  • Land
  • 21,344 Sq Ft
  • $45,918 per Acre

  Lot 181 Rockwood Trail, Winchester, VA 22602

  It's time to MAKE YOUR DREAMS A REALITY with this beautiful, nearly HALF-ACRE building lot on the PREMIUM VIEW-SIDE of Rockwood Trail - just 30 minutes from downtown Winchester! Picture a cozy, custom-built home nestled atop quiet Shawneeland, with a gentle breeze carrying whispers of nature and potential stunning valley vistas stretching as far as the eye can see. Approved for a two-bedroom

  Kristin Crosby Samson Properties

  Lot 181 Rockwood Trail, Winchester, VA 22602
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  /11

  $189,900

  • Land
  • 5 Acres
  • $37,980 per Acre

  0 0 Perry Rd, Winchester, VA 22602

  10 min or less into Winchester City, discover the possibilities on this beautiful 5-acre parcel, offering a peaceful mix of mature woods, open clearing areas, a creek, and a small pond that sits partially on the property. With 4-bedroom septic approval and no restrictions, this property provides the flexibility to create a private country retreat, recreational getaway, or secluded

  Lorie Crabill Sager Real Estate

  0 0 Perry Rd, Winchester, VA 22602
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  /2

  $250,000

  • Land
  • 5 Acres
  • $50,000 per Acre

  341 Laurel Grove Rd, Winchester, VA 22602

  THERE ARE 2 -5 ACRE BUILDING LOTS W/4 BR CONVENTIONAL PERKS APPROVED. LOT 3 IS UP ON THE HILL AND LOT 4 FRONTS THE ROAD. THESE LOTS ARE CREATED FROM A LARGER PARCEL BY WAY OF A BOUNDRY LINE ADJUSTMENT. NEW PLATS AND BOUNDRY LINE ADJUSTMENTS INCLUDED IN DOCUMENTS. NEW DEEDS WILL BE ISSUED AT CLOSING. TAX ASSESSMENTS AND TAXES ARE BASED ON THE ENTIRE PROPERTY PRIOR TO BOUNDRY LINE ADJUSTMENT. NEW

  Barbara Singhas Crum Realty, Inc.

  341 Laurel Grove Rd, Winchester, VA 22602
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  /2

  $24,900

  • Land
  • 20,473 Sq Ft
  • $52,979 per Acre

  Lot 162 Bobcat Trail, Winchester, VA 22602

  Imagine creating your own mountain getaway atop Great North Mountain. Tucked among the trees in Shawneeland, this just-under-half-acre lot offers a peaceful wooded setting, privacy, and the potential for beautiful westerly mountain views.The property includes a relatively level area that may offer possibilities for a future homesite. With thoughtful planning and clearing, envision a cozy

  Natasha Roberts Realty ONE Group Old Towne

  Lot 162 Bobcat Trail, Winchester, VA 22602
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  /78

  $260,000

  • 2 Beds
  • 1.5 Baths
  • 1,068 Sq Ft

  103 E Germain St, Winchester, VA 22601

  Roof replaced in 2020.Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a

  RoxAnn Grimes RE/MAX Roots

  103 E Germain St, Winchester, VA 22601
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  /2

  $199,900

  • Land
  • 6,969 Sq Ft
  • $1,249,375 per Acre

  1415 Ramseur Ln, Winchester, VA 22601

  Steve DuBrueler Coldwell Banker Premier

  1415 Ramseur Ln, Winchester, VA 22601
• 

  

  /12

  $8,900

  • Land
  • 12,632 Sq Ft
  • $30,690 per Acre

  155 Hawk Trail, Winchester, VA 22602

  Looking for affordable land in Shawneeland? Inventory is moving quickly in several sections, making this a rare opportunity to secure a lower‑mountain lot with easy access—ideal for those seeking both convenience and a peaceful, natural setting.This raw land parcel is on a hard surface road in a scenic, mountainous residential community just 12 miles from Winchester, Virginia. Enjoy the fresh

  Rebecca McTavish Long & Foster Real Estate, Inc.

  155 Hawk Trail, Winchester, VA 22602
• 

  /2

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  111 Haven Terrace, Winchester, VA 22602

  Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This single-level home offers a practical layout with comfortable living spaces and plenty of potential to make it your own.The main-level living design provides easy access throughout the home, making this property a great fit

  Erin Kavanagh EXP Realty, LLC

  111 Haven Terrace, Winchester, VA 22602
• 

  

  /45

  $260,000

  • 2 Beds
  • 1 Bath
  • 997 Sq Ft

  108 Martin Dr, Winchester, VA 22602

  Attention investors! Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large

  Heloisa Amar Samson Properties

  108 Martin Dr, Winchester, VA 22602

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