Winchester, VA Homes for Sale under $100,000

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  /10

  $61,900

  • Land
  • 30,056 Sq Ft
  • $89,710 per Acre

  Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602

  Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 402-9785

  Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602
• Explore Winchester

• 

  

  

  /11

  $61,900

  • Land
  • 30,056 Sq Ft
  • $89,710 per Acre

  Lots 11 & 12 Glen Ridge Rd, Winchester, VA 22602

  Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 698-4594

  Lots 11 & 12 Glen Ridge Rd, Winchester, VA 22602
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  /45

  $99,000

  $11K PRICE DROP

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

  135 Gregory Place, Winchester, VA 22603

  This 2018-built 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 dedicated laundry

  

  Diego Abregu

  Keller Williams Realty

  (540) 329-2535

  135 Gregory Place, Winchester, VA 22603
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  /11

  $61,900

  • Land
  • 30,056 Sq Ft
  • $89,710 per Acre

  Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602

  Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 712-6303

  Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602
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  /11

  $51,900

  • Land
  • 14,810 Sq Ft
  • $152,647 per Acre

  Lot 10 Glen Ridge Rd, Winchester, VA 22602

  Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 732-7734

  Lot 10 Glen Ridge Rd, 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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  /12

  $16,000

  • Land
  • 11,325 Sq Ft
  • $61,538 per Acre

  Lot 23 Panther Dr, Winchester, VA 22602

  Nestled in the tranquil community of Wilde Acres, this partially cleared, .26 acre lot offers endless potential for your dream home. Enjoy the serenity of nature while still being just a short drive from local amenities, the perfect balance of peace and convenience. Whether you’re looking for a weekend retreat or a full-time residence, this property provides the ideal setting to make your vision

  Amanda Toothman Dandridge Realty Group, LLC

  Lot 23 Panther Dr, Winchester, VA 22602
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  /12

  $80,000

  • Land
  • 5,662 Sq Ft
  • $615,385 per Acre

  520 Highland Ave, Winchester, VA 22601

  Empty lot ready to build a home one. The lot is fully fenced with front and rear gates. The front of the lot meets the sidewalks and road of Highland Ave. The rear of the lot meets a gravel alley way that could give access to off street parking on this lot. Homes in the city are in demand, so don't miss this opportunity. Zoned HR-1Can only be used for single family dwellingsFront setback:

  Michael Sprague Samson Properties

  520 Highland Ave, Winchester, VA 22601
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  /11

  $80,000

  • Land
  • 3,484 Sq Ft
  • $1,000,000 per Acre

  24 N Pleasant Valley Rd, Winchester, VA 22601

  Ready for building! Clear open lot that is ready for a home to be built. Winchester City is the fastest growing city in the state and homes are in high demand. Don't miss your opportunity. Property has road front access as well as a gravel alley in the rear that could be used for access to off street parking.Zoned MR - medium density residential districtCan only be used for single family

  Michael Sprague Samson Properties

  24 N Pleasant Valley Rd, Winchester, VA 22601
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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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  /11

  $100,000

  $30K PRICE DROP

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

  107 Lisa's Dr Unit A172, Winchester, VA 22603

  Welcome to Regency Lakes a vibrant all-age community, where you can find yourself in your dream home. We 1995 3 bed, 2 bath home, completely renovated in 2024 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 everything has been completely renovated.

  Kristina Kelly Regency Lakes

  107 Lisa's Dr Unit A172, Winchester, VA 22603
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  /14

  $59,999

  $10K PRICE DROP

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

  121 Smith Dr, Winchester, VA 22603

  JUST REDUCE....Beautifully updated 3-bedroom, 2-bath single-wide home located in the desirable Regency Lakes community on leased land. This home was fully refreshed in 2023, featuring a new roof, HVAC system, and water heater, offering peace of mind and modern efficiency for years to come. Inside, you’ll find a bright, contemporary design with tasteful finishes and a comfortable layout perfect

  Julissa Rodriguez Vaze Realty

  121 Smith Dr, 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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  /2

  $42,500

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

  0 Winding Ridge Ln, Winchester, VA 22603

  5 acres with a hand-built stone cabin located just 30 minutes from downtown Winchester. See attached deed and plat.

  Sheila Pack RE/MAX Roots

  0 Winding Ridge Ln, Winchester, VA 22603
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  /13

  $99,900

  • Land
  • 9,583 Sq Ft
  • $454,091 per Acre

  Lot 13 Route 1288, Winchester, VA 22602

  Build your dream home on Lot 13, Camden Drive in the desirable Asbury Terrace Subdivision of Winchester. This prime buildable lot offers an excellent location just off Valley Mill Road and Route 7, providing easy access for commuters while remaining close to everyday conveniences. Public utilities are available, including electricity, public water, and public sewer hookups, helping simplify the

  RoxAnn Grimes RE/MAX Roots

  Lot 13 Route 1288, Winchester, VA 22602
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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

  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 covenants—ideal for a custom small home or a

  Jim Thomson Realty ONE Group Old Towne

  Lot 84 Purcell Ln, Winchester, VA 22603
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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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  /21

  $99,900

  • Land
  • 28,314 Sq Ft
  • $153,692 per Acre

  222 Siler Ln, Winchester, VA 22603

  UPDATE--NEW PRICE. Seller says SELL...UNRESTRICTED LAND and a BRAND NEW WELL installed by SHIRLEY WELL DRILLING - 11 GPM. SELLING AT ASSESSED VALUE for 2025 ($83,000.00) plus cost of well ($ 16,900) Engineering report complete for drain field and all conveys $1,450.00 value- conveys. New Survey done -$800,00 Value-The lot has been leveled for a beautiful home site (cost $ 16,000.,00).

  Erick Erdal Long & Foster Real Estate, Inc.

  222 Siler Ln, 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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  /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 beautiful 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

  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

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

  Rebecca McTavish Long & Foster Real Estate, Inc.

  155 Hawk Trail, Winchester, VA 22602
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  /15

  $99,000

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

  208 Artifact Ave Unit 427, Winchester, VA 22603

  Kristina Kelly Regency Lakes

  208 Artifact Ave Unit 427, Winchester, VA 22603
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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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  /11

  $75,000

  $15K PRICE DROP

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

  152 Fiddler Ave Unit C318, Winchester, VA 22603

  Welcome to Regency Lakes a all age active and vibrant community, where you can find yourself in your dream home. We have updated 2001 3 bed, 2 bath home featuring a large open floor plan. Step inside to find a bright and airy open floor plan, stone wood burning fireplace and updated bathrooms. The spacious kitchen boasts a multi level center island and a pass through, perfect for both everyday

  Kristina Kelly Regency Lakes

  152 Fiddler Ave Unit C318, Winchester, VA 22603
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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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  /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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  /2

  $29,900

  • Land
  • 0 Sq Ft

  0 Pheasant Dr Unit VAFV2041958, Winchester, VA 22602

  BUILDERS DREAM! 4 adjoining vacant lots (Lots 3, 4, 5 & 6) located on Pheasant Dr in Wilde Acres in Winchester, VA. Nestled within a peaceful mountain community, these 4 partially wooded parcels provide a wonderful opportunity for future development, a private retreat, or investment potential. Enjoy the natural surroundings, privacy, and serene atmosphere while still maintaining convenient access

  Michele Gibson Samson Properties

  0 Pheasant Dr Unit VAFV2041958, 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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  /8

  $18,000

  • Land
  • 14,810 Sq Ft
  • $52,941 per Acre

  0 Tonto Trail Unit VAFV2041946, Winchester, VA 22602

  Very nice flat lot on the corner of Killbuck and Tonto Trl. This property is located om hard surface roads Potential Building lot on .34 acres located on corner of Tonto Tr. See the Beautiful mountain views coming & going. Located in Shawneeland, a beautiful mountain community with many amenities, Large Park, playground, Picnic Pavilion area, Ball field, Beach area, fishing Ponds with streams,

  Sue Fincham Samson Properties

  0 Tonto Trail Unit VAFV2041946, 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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  /11

  $98,500

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

  103 Draper Ave Unit 473, Winchester, VA 22603

  Welcome to Regency Lakes an active and vibrant community, where you can find yourself in your dream home. We have a 2017 3 bed, 2 bath home for sale featuring 1568.00 sq ft of living space. Located in Winchester, this property offers the perfect blend of modern amenities and timeless charm. Step inside to find a beautiful large eat in kitchen with tons of cabinet space and the large dining space

  Kristina Kelly Regency Lakes

  103 Draper Ave Unit 473, Winchester, VA 22603
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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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  /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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