Winchester, VA Homes for Sale under $300,000

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  /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
• Explore Winchester

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  /18

  $1,550

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  550 N Loudoun St Unit 1, Winchester, VA 22601

  Beautifully renovated in 2022, this charming 1 bedroom, 1 bathroom apartment is located in historic Winchester and offers updated living with classic character. The apartment features access to a shared coin-operated laundry room located next door at 548 N. Loudoun St. Tenant is responsible for all utilities. Available approximately Jon or before August 14, 2026. Pets are considered on a

  

  Robert Adams

  Weichert Realtors - Blue Ribbon

  550 N Loudoun St Unit 1, Winchester, VA 22601
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  /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

  $1,275

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  545 N Loudoun St Unit 3, Winchester, VA 22601

  Conveniently located 1 BDRM 1 Bath apartment near the Downtown Walking Mall in Winchester.Secured with a coded entry, is located just a few feet from the apartment. Rent is $1200 + 75 Utility Fee totaling only $1275 a month including utilities. Internet is tenants' responsibility. Security Deposit is $1200 On-site shared laundry is available in the basement (coin and app operated). Off Street

  

  Robert Adams

  Weichert Realtors - Blue Ribbon

  545 N Loudoun St Unit 3, Winchester, VA 22601
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  /45

  $84,500

  $26K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,495 Sq Ft

  135 Gregory Place, Winchester, VA 22603

  This 2018-built double wide manufactured ranch-style home is move-in ready and well maintained for its new owner! The home offers an open floor plan featuring a spacious kitchen with abundant countertop space, a large pantry, and a dining area that flows into the main living space. The living room provides plenty of open space for comfortable everyday living, and the home also includes a

  

  Diego Abregu

  Keller Williams Realty

  135 Gregory Place, Winchester, VA 22603
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  /12

  $220,000

  • 3 Beds
  • 1 Bath
  • 1,020 Sq Ft

  1000 Opequon Ave, Winchester, VA 22601

  Opportunity on Opequon! Flip, rental potential or primary occupancy for the right buyer. Ranch style home on an unfinished basement in an established community just across the street from Jim Barnett Park and Shenandoah University. A very walkable Winchester City location. Could likely add a half bath in one of the existing closets in the primary bedroom with little hassle. Potential for 4th

  

  Anna Fox

  NextHome Realty Select

  1000 Opequon Ave, Winchester, VA 22601
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  /42

  $289,900

  Coming Soon

  • 2 Beds
  • 1 Bath
  • 1,458 Sq Ft

  102 N Purcell Ave, Winchester, VA 22601

  Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  102 N Purcell Ave, Winchester, VA 22601
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  /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
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  /13

  $274,999

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft

  206 Kimberly Way, Winchester, VA 22601

  Beautifully remodeled 2-bedroom, 2.5-bath townhouse that's ready for you to move right in! This home features a stunning updated kitchen with granite countertops and stainless steel appliances, along with modern finishes throughout. Major improvements include a new roof and heat pump installed in 2023, providing added comfort and peace of mind. Spacious living areas, updated bathrooms, and

  

  Frank Armstrong, IV

  Colony Realty

  206 Kimberly Way, Winchester, VA 22601
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  /4

  $94,999

  • Land
  • 21,780 Sq Ft
  • $189,998 per Acre

  1184 N Frederick Pike, Winchester, VA 22603

  Great location on busy N. Frederick Pike with good road frontage, Zoned B-2, down from Sunnyside and Martin's Shopping Center, minutes from VA Bypass 37 & Winchester Medical Center. Site is ideal for any retail or services business.

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  1184 N Frederick Pike, 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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  /24

  $141,500

  • Land
  • 11.8 Acres
  • $11,992 per Acre

  0 Hodges Ln Unit LotWP016, 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 is the

  Chad Pangle Whitetail Properties Real Estate

  0 Hodges Ln Unit LotWP016, 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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  /7

  $133,000

  $2K PRICE DROP

  • Land
  • 5.06 Acres
  • $26,285 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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  $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
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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
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  /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
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  /21

  $285,000

  • 3 Beds
  • 1 Bath
  • 1,094 Sq Ft

  143 Dowell J Cir, Winchester, VA 22602

  Charming Rancher with Prime Location and Endless Potential! This well-built, single-level rancher offers 3 bedrooms and 1 full bath across 1,000 square feet of smartly designed living space. Nestled on a quiet street just outside Winchester city limits, this home falls within the Frederick County school district and combines peaceful surroundings with unbeatable convenience—just one minute to Rt.

  Sarah Hott Realty ONE Group Old Towne

  143 Dowell J Cir, Winchester, VA 22602
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  /5

  $10,000

  • Land
  • 11,325 Sq Ft
  • $38,462 per Acre

  Lot 11 Pheasant Dr, Winchester, VA 22602

  Discover a serene 0.26-acre lot nestled in Winchester's Wilde Acres / Mountain Falls Subdivision, where nature meets tranquility. This beautifully wooded parcel offers a perfect canvas for your dream home, surrounded by lush trees that provide both privacy and a picturesque backdrop. With convenient road frontage, access to your future home or cozy weekend retreat is effortless.

  Bridget Aikens Colony Realty

  Lot 11 Pheasant Dr, Winchester, VA 22602
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  /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
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  /15

  $77,500

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,680 Sq Ft

  166 Fiddler Ave Unit 391, Winchester, VA 22603

  A very motivated seller has reduced the price for a quick sale. Don't let this exceptional value slip through your fingers. We have a 2006 2+bed, 2 bath home for sale featuring 1680.00 sq ft of beautifully designed living space. This stunning home offers the perfect blend of modern amenities and timeless charm. Step inside to find a designer's touch throughout, featuring a beautiful stone

  Kristina Kelly Regency Lakes

  166 Fiddler Ave Unit 391, Winchester, VA 22603
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  /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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  /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

  • 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 a

  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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  /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
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  /18

  $70,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  105 Chamberlain Ct, Winchester, VA 22603

  Charming 2016 Double‐Wide Manufactured Home in a Nicely Established Park This well‐maintained 2016 manufactured double‐wide offers comfort, convenience, and plenty of space in one of the community’s most desirable locations. Situated near the entrance for easy access, this home is perfectly placed within a nicely established park known for its peaceful setting and welcoming atmosphere. Enjoy the

  Steve DuBrueler Coldwell Banker Premier

  105 Chamberlain Ct, Winchester, VA 22603
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  /2

  $59,900

  $20K PRICE DROP

  • Land
  • 8,276 Sq Ft
  • $315,263 per Acre

  Lot 84 Purcell Ln, Winchester, VA 22603

  Great for investment, air B&B or sale. Build Your Vision Near Winchester City LimitsPrime buildable lot offering the perfect balance of convenience and freedom. Located just minutes from Winchester City but still in county, shopping, the hospital, and Route 37, this property is ready for your project with public water and sewer hookups available. Freedom to Build: No HOA or restrictive

  Jim Thomson Realty ONE Group Old Towne

  Lot 84 Purcell Ln, Winchester, VA 22603
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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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  /3

  $6,500

  • Land
  • 11,325 Sq Ft
  • $25,000 per Acre

  0 Fox Trail Unit VAFV2040348, Winchester, VA 22602

  Vacant lot on Fox Trail in Wilde Acres! This is raw land, no perc test has been done. Affordable and at the top, for lots of views of North Mountain. Private - not many homes around this lot. Sign on Property

  Traci Shoberg Samson Properties

  0 Fox Trail Unit VAFV2040348, Winchester, VA 22602
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  /19

  $165,000

  • 2 Beds
  • 1 Bath
  • 652 Sq Ft

  616 Opossum Trail, Winchester, VA 22602

  Escape to the peace and privacy of Wilde Acres with this charming 2-bedroom, 1-bath cabin situated on four lots for a total of 1 acre, offering extra space and the possibility of potential expansion. This property is being sold As-Is and is in need of some cosmetic work. It presents a great opportunity for a weekend retreat, investment property, or full-time residence with a little TLC. Recent

  Dona Shiley ERA Oakcrest Realty, Inc.

  616 Opossum Trail, 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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  /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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  /45

  $220,000

  • 1 Bed
  • 1 Bath
  • 637 Sq Ft

  106 Blackfeet Trail, Winchester, VA 22602

  Charming mountain retreat nestled on a full acre in Shawneeland! This cozy 1-bedroom, 1-bath cabin offers the perfect blend of privacy, nature, and modern comfort. Situated on two combined lots totaling approximately 1 acre, the property provides plenty of space to enjoy the peaceful wooded setting.Recent improvements include a newer architectural shingle roof, gutter, vinyl clad double

  Tiffany Feathers-Brown MarketPlace REALTY

  106 Blackfeet Trail, Winchester, VA 22602
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  /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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