Winchester, VA Homes for Sale under $300,000

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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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  /10

  $255,000

  $10K PRICE INCREASE

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2967 Sorrell Ct, Winchester, VA 22601

  This diamond in the rough has solid bones and plenty of potential for the right buyer. The HVAC system is only two years old, the water heater is brand new, and both full bathrooms have already been updated. The home could use some fresh paint, and the dishwasher is currently not working, but the major systems are in great shape—making this an excellent opportunity for a starter home or

  Jamie Cook Treck Realty LLC

  2967 Sorrell Ct, Winchester, VA 22601
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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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  /2

  $275,000

  • Land
  • 5 Acres
  • $55,000 per Acre

  341 Laurel Grove Rd, Winchester, VA 22602

  THERE ARE 2 -5 ACRE BUILDING LOTS W/4 BR CONVENTIONAL PERKS APPROVED. LOTS 3 AND 4. THESE LOTS ARE CREATED FROM A LARGER PARCEL BY WAY OF A BOUNDRY LINE ADJUSTMENT. NEW DEEDS WILL BE ISSUED AT CLOSING. SEPERATE TAX ASSESSMENTS ARE UNAVAILABLE BUT APPRAISALS ARE AVAILABLE FOR BOTH LOTS. LISTING PRICE IS PER LOT. WILL BUILD TO SUIT.

  Barbara Singhas Crum Realty, Inc.

  341 Laurel Grove Rd, Winchester, VA 22602
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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
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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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  /45

  $260,000

  • 2 Beds
  • 1 Bath
  • 997 Sq Ft

  108 Martin Dr, Winchester, VA 22602

  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 windows that let in plenty

  Heloisa Amar Samson Properties

  108 Martin Dr, Winchester, VA 22602
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  /19

  $141,500

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

  0 Hodges Lot 14 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 14 Ln, Winchester, VA 22603
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  /2

  $200,000

  • 1 Bed
  • 1 Bath

  5737 N Frederick Pike, Winchester, VA 22603

  4.2 Acres, Sold As-Is, Flat Usable Lot, Partially Wooded, Well and Septic Exists, Just Outside of Winchester VA, No HOA, Unrestricted. Well and septic on property . Well is located in back of old mobile home at water pump. Septic located further back behind old mobile home marked wirh red sparay paint. Health department docs are in bright. Neither house nor mobile home livable.Sold As Is With

  Tracy Link Coldwell Banker Premier

  5737 N Frederick Pike, Winchester, VA 22603
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  /7

  $125,000

  • Land
  • 8.3 Acres
  • $15,060 per Acre

  0 Light Rd, Winchester, VA 22603

  Large lot available! WELL ON SITE! Over 8 acres for sale in Northern Frederick County, VA at the top of The Shenandoah Valley! Perfect for building or recreation/hunting. Turkey, deer and other wildlife abound. Only 20 minutes from Winchester! 20 minutes from Berkeley Springs, WV! Looking for that perfect get-a-way spot to enjoy wildlife and nature? This may be it! Lot is fully wooded. Ideal

  Jennifer Watt Century 21 Redwood Realty

  0 Light Rd, 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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  /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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  /52

  $240,000

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  127 8 Brookland Terrace Unit 8, Winchester, VA 22602

  Fantastic location! This spacious second-floor condo offers vaulted ceilings, generously sized rooms, and a bright, open feel throughout. Enjoy relaxing on the private deck overlooking the common area and mature trees. The floor plan features a large living room, separate dining room, two spacious bedrooms, and two full bathrooms. The primary suite includes a private bath, a large closet, and

  Meghan Pachas Realty ONE Group Old Towne

  127 8 Brookland Terrace Unit 8, 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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  /8

  $250,000

  • Land
  • 15.63 Acres
  • $15,995 per Acre

  15.63 Acres 52-2-b, Winchester, VA 22603

  15.63 +/- acres, located at the top of Round Hill, call for information about access, the property will be sold with deed restrictions against building at the top of the hill.

  John Scully Colony Realty

  15.63 Acres 52-2-b, Winchester, VA 22603
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  /21

  $269,000

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  321 N Kent St, Winchester, VA 22601

  Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall restaurants, shopping, the library and more. Easy access to Rt. 7 and 81. The main level has a nice open floor plan, consisting of kitchen, dining and living areas. The main level also features a half bath and bonus room, perfect for an office or den. Upstairs you will find three bedrooms, full bathroom and

  Amy Capitano MarketPlace REALTY

  321 N Kent St, Winchester, VA 22601
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  /35

  $295,000

  $5K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 1,028 Sq Ft

  902 Enfield Dr, Winchester, VA 22602

  Will Walraven Realty One Group Key Properties

  902 Enfield Dr, 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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  /40

  $299,900

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  110 Brookland Ct Unit 10, Winchester, VA 22602

  Welcome home to this one-of-a-kind, fully renovated penthouse condo that has been transformed right down to the studs! Offering luxury finishes rarely found at this price point, this stunning residence is unlike anything else available in Frederick County under $300,000. Every detail has been thoughtfully updated, including a new gas furnace, new HVAC system, new flooring throughout, neutral

  Traci Shoberg Samson Properties

  110 Brookland Ct Unit 10, Winchester, VA 22602
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  /20

  $154,650

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

  0 Hodges Lot 11 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 11 Ln, Winchester, VA 22603
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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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  /25

  $275,000

  $45K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  317 Fairview Ave, Winchester, VA 22601

  Price improvement - bring offers! Fully Renovated SFH in Historic Winchester! Prime location. Just minutes from charming Historic Downtown Winchester featuring local shops, restaurants, entertainment, and more! Beautifully Updated throughout. This charming home offers bright, inviting living spaces with modern finishes and thoughtfully updates designed for comfortable everyday living. w Just Move

  Donna Lutkins Real Broker, LLC

  317 Fairview Ave, Winchester, VA 22601
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  /20

  $274,900

  • Land
  • 6.84 Acres
  • $40,190 per Acre

  202 Cedar Grove Rd, Winchester, VA 22603

  Calling investors and outdoors enthusiasts: This property is close to town with a large shop, and a potential small home after renovations! The vacant home is in need of love and repairs, but has electric, water from a private well, and a permitted septic rated for 2 bedrooms. The large shop has electric and an adjacent H2O hydrant, as well as a loft for extra space. Backing up to quiet

  Ryan Foster Keller Williams Realty

  202 Cedar Grove Rd, Winchester, VA 22603
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  /52

  $290,000

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  700 Tomahawk Trail, Winchester, VA 22602

  Welcome to this charming ranch-style home situated on a spacious .44-acre corner lot in the desirable Shawneeland community. Thoughtfully updated and well maintained, this home offers comfort, functionality, and modern touches throughout. The kitchen has been enhanced with a newly added pantry (2026) making everyday living and entertaining effortless. The primary bedroom features French doors

  Lindsey Gomes Real Broker, LLC

  700 Tomahawk Trail, Winchester, VA 22602
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  /38

  $139,900

  • Land
  • 20 Acres
  • $6,995 per Acre

  TWO LOTS ON Siler Rd, Winchester, VA 22603

  In the Gainesboro area of Frederick County, VA, offered here are (2) 10 acre lots with unique characteristics. The land is within the Rhine Forest Estates "subdivision" with NO COVENANTS or RESTRICTIONS. First thought is for recreation. The first lot borders Siler Road (hard surfaced state road) and also extends over Bucksaw Ln, running to the banks of Isaac Creek. The 2nd lot is right next door,

  Edward Beightol Cedar Creek Real Estate

  TWO LOTS ON Siler Rd, Winchester, VA 22603
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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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  /15

  $189,000

  $11K PRICE DROP

  • Land
  • 7.4 Acres
  • $25,541 per Acre

  0 7 4 Ac Mountain Falls Rd, Winchester, VA 22602

  Enjoy stunning mountain views from this exceptional property, featuring approximately 60% open land and 40% wooded acreage. The building site is already cleared, making it ready for your dream home.Conveniently located just 25 minutes west of Winchester city limits, this property offers the perfect blend of accessibility and peaceful rural living. It checks all the boxes—Mountain Views,

  Jeff Boppe Long & Foster Real Estate, Inc.

  0 7 4 Ac Mountain Falls Rd, Winchester, VA 22602
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  /2

  $199,900

  $50K PRICE DROP

  • Land
  • 5 Acres
  • $39,980 per Acre

  181 Oak Dr, Winchester, VA 22603

  Build Your Vision at the End of the Lane Discover a rare opportunity to create a custom estate in an established community of luxury homes (up to 4,000 sq. ft.). Located at the quiet end of the street, this lot offers the perfect blend of privacy and prestige. Enjoy the peace of a secluded setting without sacrificing convenience—you are minutes from town with effortless access to Route 50. With a

  Jim Thomson Realty ONE Group Old Towne

  181 Oak Dr, Winchester, VA 22603
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  /21

  $213,000

  $22K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 970 Sq Ft

  127 Geronimo Trail, Winchester, VA 22602

  Nestled in the serene Shawneeland community, this charming ranch-style home offers a perfect blend of comfort and tranquility. Set on a generous 1.92-acre lot, the property features a gently sloping landscape adorned with mature trees, creating a peaceful retreat from the hustle and bustle of everyday life. This 3-bedroom, 1-bathroom home invites you to unwind and make lasting memories. The

  Steve DuBrueler Coldwell Banker Premier

  127 Geronimo Trail, Winchester, VA 22602
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  /16

  $249,900

  • Land
  • 1 Acre
  • $249,900 per Acre

  Lot 36 Lake Serene Dr, Winchester, VA 22603

  Lake Serene Winchester Va. Don’t miss this rare opportunity to own the last available build-able lot in peaceful, secluded Lake Serene, a private, established lake community quietly tucked away, yet only 10 minutes from Old Town Winchester! You will never find an opportunity like this to enjoy the peace and tranquility of waterfront living with the added bonus of being only a few miles from

  Mark Jenkins Rappahannock Real Estate, LLC.

  Lot 36 Lake Serene Dr, Winchester, VA 22603
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  /7

  $179,900

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  108 Comanche Trail, Winchester, VA 22602

  *Short Sale* SOLD AS IS* Discover the potential of this ranch-style home tucked away in Shawneeland! Offering 3 bedrooms and 2 full baths, this property features an open floor plan with a bright living room, kitchen with plenty of cabinet space, and spacious dining area. The primary suite includes a private bath and ample closet space. Enjoy peaceful mountain living with a large deck overlooking

  Waleed Abuzar RE/MAX Galaxy

  108 Comanche Trail, Winchester, VA 22602
• 

  

  /10

  $280,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 817 Sq Ft

  580 York Ave, Winchester, VA 22601

  This charming bungalow in the heart of the City of Winchester has already been beautifully renovated, offering the perfect blend of classic charm and modern living. Featuring 2 cozy bedrooms and a full bathroom, the home is designed with comfort and functionality in mind. Enjoy an updated kitchen and bathrooms, new appliances, and central A/C for a fresh, modern feel. The newly added front deck

  Yoselin Mejia The Vasquez Group LLC

  580 York Ave, Winchester, VA 22601
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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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  /24

  $150,000

  • Land
  • 10 Acres
  • $15,000 per Acre

  0 Fall Run Ln Unit 15 ACRES TOTAL, Winchester, VA 22602

  Private access (gated) to get to the 10 acre and 5 acre lots. Take the gravel lane (gate is not locked) for about the length of 2 football fields to where the land begins. This private lane ends at the land. There are 2 nice utility sheds and an outhouse facility!, next to a campsite. (The firewood stays) The land is nicely wooded with tall hardwoods. There is an ATV trail along the left edge of

  Edward Beightol Cedar Creek Real Estate

  0 Fall Run Ln Unit 15 ACRES TOTAL, Winchester, VA 22602
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  /26

  $295,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft

  110 Duwamish Trail, Winchester, VA 22602

  Charming and Move-In Ready Ranch in a Peaceful Setting!Welcome home to this beautifully refreshed single-level ranch nestled on a spacious, tree-lined lot. This inviting home features a bright and functional layout with updated finishes throughout. The kitchen offers grey cabinetry, granite countertops, and stainless steel appliances, creating a clean and modern space perfect for everyday

  Tina Jacobin Main Street Realty

  110 Duwamish Trail, Winchester, VA 22602
• 

  

  /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

Showing Results 41 - 80, Page 2 of 3