Winchester, VA Homes for Sale under $100,000

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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
• 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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  /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

  $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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  /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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  /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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  /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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  /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

  $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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  /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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  /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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  /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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  /2

  $24,900

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

  Lot 162 Bobcat Trail, Winchester, VA 22602

  Perched atop Great North Mountain, this wooded lot offers the potential for stunning westerly mountain views. Just under half an acre, the property offers a small driveway already cut in and a level homesite area, an ideal setting for your future mountain retreat, whether a chalet, cabin, or full-time residence. Surrounded by nature, this peaceful lot provides elevated views while still being

  Natasha Roberts Realty ONE Group Old Towne

  Lot 162 Bobcat Trail, Winchester, VA 22602
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  /12

  $9,995

  • Land
  • 12,632 Sq Ft
  • $34,466 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
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  /5

  $10,000

  • Land
  • 0 Sq Ft

  Lot 13 Tomahawk Trai 0, Winchester, VA 22602

  Welcome to Shawneeland! This mountain community is tucked away in a rural setting and a short distance to shopping, restaurants and Winchester's Historic Downtown. Utilize this 0.48 acre lot as a potential building lot, recreational space or enjoy the amenities such as Lake Cherokee with a beach area, fishing and picnic areas. Purchaser to verify location of boundary lines.

  Kim Hurst MarketPlace REALTY

  Lot 13 Tomahawk Trai 0, Winchester, VA 22602
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  /2

  $3,500

  • Land
  • 10,890 Sq Ft
  • $14,000 per Acre

  107 Fox Trail, Winchester, VA 22602

  Babak Taghavi Venture Realty

  107 Fox Trail, Winchester, VA 22602
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  /24

  $25,000

  • Land
  • 1.43 Acres
  • $17,483 per Acre

  LOT 5A Fox Trail, Winchester, VA 22602

  Beautiful building lot located in Mountain Falls Park – Wilde Acres. This is the last lot on the right on Fox Trail, offering excellent privacy and seclusion. The property backs to permanent open space, providing a peaceful setting with mountain views and abundant wildlife. Approved for a 3-bedroom septic system with a certification letter on file. A current survey is also available. This is an

  Nadeem Helfer Samson Properties

  LOT 5A Fox Trail, Winchester, VA 22602
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  /5

  $4,000

  • Land
  • 13,503 Sq Ft
  • $12,903 per Acre

  0 Fox Trail Unit VAFV2042734, Winchester, VA 22602

  .31 acre wooded lot on an incline. No septic or well tests have been done. Seller doesn't know if it's buildable. Drive by any time to show.

  Tanner Pack RE/MAX Roots

  0 Fox Trail Unit VAFV2042734, Winchester, VA 22602
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  /9

  $17,000

  • Land
  • 21,780 Sq Ft
  • $34,000 per Acre

  Lot 111 Cub Trail, Winchester, VA 22602

  Tired of the bustle of city life? Visit Shawneeland in northwestern Frederick County, Virginia. Visit for a day and stay for a lifetime. This mountaintop lot on the western slope is just the place to build a home. Enjoy Shawneeland's amenities: a spring-fed lake perfect for swimming and fishing, a playground for the children, and hiking trails for the entire family.Love the country but want

  Rebecca McTavish Long & Foster Real Estate, Inc.

  Lot 111 Cub Trail, Winchester, VA 22602
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  /9

  $17,000

  • Land
  • 18,295 Sq Ft
  • $40,476 per Acre

  Lot 76 Bear Trail, Winchester, VA 22602

  Looking for a lot in a quiet, rural development where you can enjoy the beauty of nature, listen to the birds, and view an occasional wild turkey or deer? This undeveloped lot in Shawneeland may be just the place for you. With its spring-fed lake, great for fishing or swimming, and mountain trails, Shawneeland is the perfect place to build a getaway retreat or a full-time residence. Located

  Rebecca McTavish Long & Foster Real Estate, Inc.

  Lot 76 Bear Trail, Winchester, VA 22602
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  /9

  $9,500

  • Land
  • 23,958 Sq Ft
  • $17,273 per Acre

  LOTS 8 & 9 Elk Trail, Winchester, VA 22602

  Great opportunity to own two beautiful wooded lots full of mature trees and plenty of privacy! These adjoining parcels offer a wonderful chance to connect with nature and enjoy peaceful surroundings. Located just about 30 minutes from downtown Winchester, you get the perfect mix of country calm and town convenience. Whether you’re thinking about outdoor fun, future plans, or simply an investment,

  Kristin Crosby Samson Properties

  LOTS 8 & 9 Elk Trail, Winchester, VA 22602
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  /2

  $39,900

  $10K PRICE INCREASE

  • Land
  • 19,602 Sq Ft
  • $88,667 per Acre

  Lot 205 Rockwood Trail, Winchester, VA 22602

  Offers the best views of the valley. Beautiful lot (almost 1/2 acre) with valley views of Shenandoah waiting for your clients to build your new home on or buy and hold. Perfect for those who want privacy and view. Great for primary home or weekend retreat. Cert Letter 3 bedroom perk..

  Jim Thomson Realty ONE Group Old Towne

  Lot 205 Rockwood Trail, Winchester, VA 22602
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  /2

  $8,500

  • Land
  • 0 Sq Ft

  0 0 Unit VAFV2036674, Winchester, VA 22602

  Kelly Hayes Samson Properties

  0 0 Unit VAFV2036674, Winchester, VA 22602
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  /15

  $89,000

  • Land
  • 5.02 Acres
  • $17,729 per Acre

  0 Pack Horse Road Lot B Unit VAFV2042704, 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 5 acre lot B is wooded, has an old cabin (do not enter and at one time had electric), 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

  Dave Spence RE/MAX Roots

  0 Pack Horse Road Lot B Unit VAFV2042704, Winchester, VA 22603
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  /2

  $12,800

  • Land
  • 17,424 Sq Ft
  • $32,000 per Acre

  0 Budwood Trail Unit 11620368, Winchester, VA 22602

  Nice level corner wooded lot. Corner of Budwood and Rockwood Follow your GPS to the corner point. All measurements are taken from government sources. Such as the actual .4. acres is actually .398 acres rounded up.

  John Holsinger JOHN S HOLSINGER REAL ESTATE BROKER LLC

  0 Budwood Trail Unit 11620368, Winchester, VA 22602
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  /6

  $12,900

  • Land
  • 10,890 Sq Ft
  • $51,600 per Acre

  Lot 17 Fox Trail, Winchester, VA 22602

  Are you looking for an affordable approved building lot under 20 minutes to Winchester Medical Center I 81 or I 66 and an overwhelming sense of nature with unparalleled mountain views? Look no further! Mountain Falls Park is known for its close proximity to town, waterfalls, views for miles and a quiet community. This lot is very buildable it is level, has a current survey, recorded plat and a

  Nadeem Helfer Samson Properties

  Lot 17 Fox Trail, Winchester, VA 22602
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  /11

  $90,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  107 Cutshaws Ct Unit C345, Winchester, VA 22603

  Welcome to Regency Lakes a all age active and vibrant community, where you can find yourself close to all the action, while maintaining that country feel. We have a 2002 3 bed, 2 bath home for sale featuring 1568.00 sq ft of beautifully designed living space. Located in/near Winchester, this property offers the perfect blend of modern amenities and timeless charm. Step inside to find a large

  Kristina Kelly Regency Lakes

  107 Cutshaws Ct Unit C345, Winchester, VA 22603
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  /16

  $85,000

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  140 Fiddler Ave, Winchester, VA 22603

  Welcome to this impeccably updated, 2013-built manufactured home offering 1,000 sq. ft. of move-in-ready living space. Featuring a desirable floor plan with a nice flow from the kitchen to the living room, this home offers 2 bedrooms and 2 full, totally renovated bathrooms. The modern interior boasts recessed lighting throughout and new flooring. Outside, you'll find a brand-new walkway, a

  Jeremiah Wilson Realty ONE Group Old Towne

  140 Fiddler Ave, Winchester, VA 22603
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  /23

  $49,000

  • Land
  • 1.49 Acres
  • $32,886 per Acre

  Lot 37 Poplar Trail, Winchester, VA 22602

  Build your dream home on this spacious 1.49-acre corner lot located in the desirable Shawneeland community. Offering ample space and flexibility for your future home, this property is ready for its next owner to bring their vision to life. With a reasonable offer, the seller will provide two sets of architectural plans to help jumpstart the building process: Plan #1: Approximately 1,541 square

  Jennifer Forsch Pearson Smith Realty, LLC

  Lot 37 Poplar Trail, Winchester, VA 22602
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  /15

  $30,000

  • Land
  • 1.53 Acres
  • $19,608 per Acre

  Lot 10,11,12-13 A 60 Fox Trail, Winchester, VA 22602

  Attention Builders! 4 Pack of contiguous building lots in Wilde Acres -Mountain Falls Park, you have the opportunity to construct your very own mountain top retreat. Mountain Falls Park is conveniently located, just a short drive away from Stephens City or downtown Winchester, VA, providing an easy commute while still offering the seclusion and serenity of the mountains. Immerse yourself in

  Nadeem Helfer Samson Properties

  Lot 10,11,12-13 A 60 Fox Trail, Winchester, VA 22602
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  /2

  $25,000

  • Land
  • 16,552 Sq Ft
  • $65,789 per Acre

  0 Trail Unit VAFV2043224, Winchester, VA 22602

  Nestled in the serene Shawneeland community, this exceptional corner lot offers a unique opportunity to create your dream home amidst nature's beauty. Spanning 0.38 acres, this parcel is not just a piece of land; it's a canvas for your vision of luxury living.

  Tessa Matthews NextHome Realty Select

  0 Trail Unit VAFV2043224, Winchester, VA 22602
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  /23

  $94,500

  $5K PRICE DROP

  • Land
  • 5.49 Acres
  • $17,213 per Acre

  0 Whispering Knolls Dr, Winchester, VA 22603

  *Price Improvement* Discover the perfect blend of privacy and natural beauty with this 5.49-acre parcel on Whispering Knolls Dr in Winchester, VA. Nestled among scenic country roads, this property offers a peaceful setting to build your dream home. Located approximately 6 miles from I-81, it provides a manageable commute while still offering the charm of rural living. Winchester Medical Center is

  Theresa Marshall Samson Properties

  0 Whispering Knolls Dr, Winchester, VA 22603
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  /3

  $79,900

  • Land
  • 6.06 Acres
  • $13,185 per Acre

  0 Four Wheel Dr Unit VAFV2041542, Winchester, VA 22602

  All wooded in private area with other nice homes. About 30 minutes south west of hospital, Wal-Mart. No HOA that allows you to do anything with your property. Older 3BR Perc expired. You could potentially renew it. Ideal to build a dream home and unlimited options. Last mile is a deeded dirt road. Listing agent has interest in the property

  Ravinder Avala Premium Realty, LLC

  0 Four Wheel Dr Unit VAFV2041542, Winchester, VA 22602

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