Winchester, VA Homes for Sale with Acreage

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  /50

  $425,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  220 Chestnut Grove Rd, Winchester, VA 22603

  Experience the best of country living with this charming 2-Bedroom, 1-Bath Rancher nestled on 15 unrestricted acres in beautiful Frederick County, VA. Perfect as a full-time residence, weekend retreat, or potential farm, this property offers the peace and privacy of rural life while still being within easy reach of town conveniences.Step inside to find a cozy and move-in ready Home featuring

  

  Laura King

  MarketPlace REALTY

  (540) 351-9580

  220 Chestnut Grove Rd, Winchester, VA 22603
• Explore Winchester

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  /13

  $200,000

  • 3 Beds
  • 2 Baths
  • 2,430 Sq Ft

  163 Cabin Ln, Winchester, VA 22603

  Discover the potential in this 3 bedroom, 2 bath home on 6.10 unrestricted acres, the perfect opportunity for buyers looking to create their own country retreat. The home is in need of significant work and is being sold AS IS. Outside, you’ll find a detached garage with an apartment above, ideal for guests, rental income, or multi-generational living. Multiple sheds provide ample storage for

  

  Kerry Wysong

  Long & Foster Real Estate, Inc.

  (540) 709-8545

  163 Cabin Ln, Winchester, VA 22603
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  /6

  $55,000

  • Land
  • 5.23 Acres
  • $10,516 per Acre

  0 0 Shockeysville Rd, Winchester, VA 22603

  Embrace the serenity of nature on this 5.23-acre wooded lot, offering the perfect blend of privacy, beauty, and possibility. Tucked away in a peaceful setting, this property features a picturesque pond, creating an ideal backdrop for your future home, weekend getaway, or recreational escape. Whether you're dreaming of building a custom home, setting up a private retreat, or simply investing in

  

  Kerry Wysong

  Long & Foster Real Estate, Inc.

  (540) 329-2751

  0 0 Shockeysville Rd, Winchester, VA 22603
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  /12

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  2718 Welltown Rd, Winchester, VA 22603

  Beautiful and buildable lots on Welltown Road. Build your dream house and an extended family suite/ guest house. Build two, live in one, sell one! There are so many option on this unrestricted parcel. The mobile home on the property has electric, well and septic. The mobile home is not where the value is and is a tear down. The second parcel has been perc previously and is suitable for building.

  

  Tracey Scott

  Path Realty

  (540) 453-8745

  2718 Welltown Rd, Winchester, VA 22603
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  /54

  $609,900

  • 3 Beds
  • 2.5 Baths
  • 2,618 Sq Ft

  281 Light Rd, Winchester, VA 22603

  NO HOA/NO RESTRICTIONS! Motivated Sellers! Bring your offers! Main Level Living! POOL! 5 GARAGE SPACES, POLE BARN & MORE! Appraised for $646,000! Ranch-Style Retreat on almost 8.5 Acres in Frederick County, VA, 20 mins. from Winchester! Calling all Homesteaders - your Farmette awaits! This property offers endless possibilities, any type of hobby, gardening, farmette, horses, workshop, mechanic's

  Jennifer Watt Century 21 Redwood Realty

  281 Light Rd, Winchester, VA 22603
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  /61

  $395,000

  • 3 Beds
  • 1 Bath
  • 1,582 Sq Ft

  859 Brush Creek Rd, Winchester, VA 22603

  This rustic home on acreage is located north of Winchester in the Cross Junction area of the county. On the market for the first time since the 1950’s the home features 3 bedrooms, 1 bathroom, and nearly 1600 +/- square feet of living space. Access is secured via extensive road frontage on paved and state-maintained Brush Creek Road. Electricity, well, and septic are already installed,

  Chad Pangle Whitetail Properties Real Estate

  859 Brush Creek Rd, Winchester, VA 22603
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  /37

  $215,000

  • Land
  • 10.77 Acres
  • $19,963 per Acre

  0 Brush Creek Rd Unit LotWP002, Winchester, VA 22603

  This land is located north of Winchester in the Cross Junction area of the county. Part of what was once a much larger family farm, and on the market for the first time since the 1950's. Access is secured via extensive road frontage on paved and state-maintained Brush Creek Road. A terrific location for your next country home. An electricity service line is already running on the property, making

  Chad Pangle Whitetail Properties Real Estate

  0 Brush Creek Rd Unit LotWP002, Winchester, VA 22603
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  /66

  $1,200,000

  • Land
  • 124 Acres
  • $9,677 per Acre

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603

  Here’s a piece of pristine land on the market for the first time since the late 70’s with nearly endless possibilities for the next owner(s). This property is located north of Winchester and very near the West Virginia line. This prime piece of real estate has been family-owned and operated for decades. It is a mix of mostly flat hay ground and wooded acreage that stretches to the top

  Chad Pangle Whitetail Properties Real Estate

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603
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  /41

  $77,700

  • Land
  • 6.09 Acres
  • $12,759 per Acre

  440 Iris Ln, Winchester, VA 22602

  Owner Financing Available! (see details below)Enjoy breathtaking, unrivaled views of the Shenandoah Valley below from this ridgetop property on Little North Mountain.Property Overview:Address: 440 Iris Lane, Winchester, VA 22602Size: 6.09 AcresKey Features:Gorgeous Sunset Valley ViewsTwo Lots in One Build on Both or Split Off!Extensive Road

  Robert Scott AcreTown.com

  440 Iris Ln, Winchester, VA 22602
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  /51

  $1,115,000

  • 7 Beds
  • 4.5 Baths
  • 4,180 Sq Ft

  207 Westview Dr, Winchester, VA 22603

  Welcome to 207 Westview Drive, a secluded sanctuary nestled on just over six wooded acres in the heart of the Shenandoah Valley—mere minutes from the charm of Historic Old Town Winchester. With over 6,600 square feet of beautifully finished living space, this one-of-a-kind property offers the perfect blend of luxury, comfort, and natural beauty. Tucked deep into the trees, yet close to shops,

  Carolyn Young Samson Properties

  207 Westview Dr, Winchester, VA 22603
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  /60

  $815,000

  • 4 Beds
  • 3.5 Baths
  • 4,461 Sq Ft

  162 Janes Way, Winchester, VA 22602

  Discover this beautifully updated home on 5 private acres in the sought-after Brookneill Subdivision—just minutes from Winchester! The home includes numerous updates, including new hardwood floors through the living room, and stairs, new kitchen cabinets, countertops, sink, and appliances. Upstairs features two huge bedrooms with new carpet, the finished basement offers new luxury vinyl plank

  Tanner Pack RE/MAX Roots

  162 Janes Way, Winchester, VA 22602
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  /58

  $635,000

  • 6 Beds
  • 4 Baths
  • 2,672 Sq Ft

  220 Snappy Ln, Winchester, VA 22602

  This stunning two-level home sits on a flat, picturesque 7.44-acre lot, offering endless possibilities for the right buyer.The basement was completely remodeled in 2025, featuring a brand-new kitchen, a full bathroom, and plenty of open living space—perfect for guests, recreation, or rental potential. A property with this much land and potential is truly a must-see!

  Mauricio Argandona Fairfax Realty Select

  220 Snappy Ln, Winchester, VA 22602
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  /75

  $749,900

  • 4 Beds
  • 4 Baths
  • 3,783 Sq Ft

  137 Stonebrook Rd, Winchester, VA 22602

  Perched on an elevated lot, this handsome Colonial provides panoramic views from the spacious wrap-around porch and privacy for the fully-fenced back yard with composite deck. Lower level with front entrance includes office with full bath and large rec room. Main level has bedroom with full bath complemented by Primary with ensuite bath and two additional bedrooms and full bath on upper level,

  Dallas Croft Samson Properties

  137 Stonebrook Rd, Winchester, VA 22602
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  /42

  $767,900

  • 3 Beds
  • 3 Baths
  • 2,112 Sq Ft

  1049 Laurel Grove Rd, Winchester, VA 22602

  Tucked away on a quiet cul-de-sac, this custom 3-bedroom, 3-bath home is sited on a private, wooded lot offering stunning mountain views and a true sense of seclusion. The property provides a serene, park-like setting that feels worlds away, yet is conveniently located. The main-level primary suite features an elegant bathroom with a walk-in shower and soaking tub. The additional Two bedrooms on

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
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  /65

  $799,900

  • 4 Beds
  • 3.5 Baths
  • 5,040 Sq Ft

  2411 Hunting Ridge Rd, Winchester, VA 22603

  This is the one you've been waiting for! Welcome to 2411 Hunting Ridge Rd. This large and private classic colonial is ready for you. With over 5000 sq ft and more than 5 acres of property, this beautiful home has it all. The winding tree-lined (and paved!) driveway invites you in. Enter into the welcoming two story foyer, which is flanked by lovely formal dining and sitting rooms. Exploring

  Amanda White Nova Home Hunters Realty

  2411 Hunting Ridge Rd, Winchester, VA 22603
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  /148

  $960,000

  • 5 Beds
  • 5.5 Baths
  • 6,256 Sq Ft

  150 Ewell Dr, Winchester, VA 22602

  Welcome to Equestrian Estates, a sought-after Winchester community with no HOA, where this stately 5-bedroom, 6-bath Colonial offers over 6,700 square feet of beautifully finished living space on nearly 3 acres. Originally built in 2007 and extensively updated in 2020, the home showcases high-end finishes throughout, including fully renovated bathrooms with luxury details such as smart toilets,

  Reed Jimenez Hunt Country Sotheby's International Realty

  150 Ewell Dr, Winchester, VA 22602
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  /74

  $659,000

  • 3 Beds
  • 2.5 Baths
  • 2,348 Sq Ft

  280 Plow Run Ln, Winchester, VA 22602

  Now available: a custom-built, one-level home situated on 3.02 peaceful acres. This property boasts a highly convenient country location, less than nine miles from Winchester Medical Center. Constructed in 2017, this elegant home offers a functional floor plan with a contemporary flair. Entryway leads into an open living area featuring nine-foot ceilings and gorgeous hardwood floors, seamlessly

  Angela Duncan MarketPlace REALTY

  280 Plow Run Ln, Winchester, VA 22602
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  /75

  $644,900

  • 5 Beds
  • 4 Baths
  • 3,432 Sq Ft

  3782 Wardensville Grade, Winchester, VA 22602

  Second chance on this Spacious Ranch-Style Retreat on 5+ Acres with Mountain Views Welcome to this beautifully updated ranch-style home offering over 5 acres of privacy, modern comforts, and sweeping mountain views. From the inviting covered front porch, step inside to a bright, open living room featuring durable LVP flooring and sliding glass doors that lead to an expansive deck—the perfect spot

  Amanda Gulla Preslee Real Estate

  3782 Wardensville Grade, Winchester, VA 22602
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  /93

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 3,532 Sq Ft

  430 Saddleback Ln, Winchester, VA 22602

  Welcome to 430 Saddleback Lane in Sheridan's Miss. Located minutes to downtown Winchester, VA. This 8.51 acre lot features lush landscaping and mature trees, with just the right amount of open space. The in ground salt water pool is the perfect spot for these hot summer days! This home has been well maintained and it shows. Enjoy morning coffee on your covered wrap around deck on the front of the

  Jim Stafford ERA Oakcrest Realty, Inc.

  430 Saddleback Ln, Winchester, VA 22602
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  /129

  $1,129,000

  • 5 Beds
  • 4.5 Baths
  • 5,426 Sq Ft

  410 Valley View Dr, Winchester, VA 22603

  Fresh to market is this unexpected property that offers the sense of home combined with the amenities of a full-time retreat. This country escape is located within minutes of town with NO HOA. Markets, restaurants, stores, shopping are handy for a quick errand and allows you to get back fast and enjoy a lazy day at the pool. Additional offerings include 9.83 private acres, a fully outfitted

  Angela Duncan MarketPlace REALTY

  410 Valley View Dr, Winchester, VA 22603
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  /86

  $643,999

  • 4 Beds
  • 3 Baths
  • 3,442 Sq Ft

  121 Sweetbriar Ln, Winchester, VA 22603

  "Private haven Rancher" on 13 plus acres with 4 Bedrooms and 3 full baths. Hardwood floors throughout home. See-thru Fireplace between Dining room and Living room. Recent upgraded kitchen with new flooring ,counter tops and fresh paint. Owners' Suite has bathroom w/whirlpool tub, separate shower, double sinks and French door access to the rear deck. Finished basement with full bath, bedroom,

  Andrew Hensley Samson Properties

  121 Sweetbriar Ln, Winchester, VA 22603
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  /74

  $669,000

  • 3 Beds
  • 3.5 Baths
  • 3,008 Sq Ft

  355 Fishel Rd, Winchester, VA 22602

  Experience the epitome of homeownership with this stunning colonial home property perfectly set on 2.5+ acres of serene land just moments from all the conveniences of town. Offering the perfect blend of classic charm and modern amenities, this home is ideal for those seeking privacy without sacrificing accessibility. Thoughtfully designed with generous living spaces. Upon entering, you're greeted

  Daniel Brereton RE/MAX Roots

  355 Fishel Rd, Winchester, VA 22602
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  /36

  $799,900 New Construction

  • 3 Beds
  • 2.5 Baths

  6 Dicks Hollow Rd, Winchester, VA 22603

  Great Opportunity on this Brand-New Ranch Home Sitting on 2.82 Acres, Convent to Shopping and Commuter Routes to Winchester, Martinsburg and Northern Virginia. Open Concept with Split Bedroom Design. Front Board and Batten siding for a unique look. Large Primary Suite with spacious walk-in closet and 6' Shower. Main Level Private Office. Chief's Kitchen with Quarts Countertops, Island,

  Brett Sowder RE/MAX Roots

  6 Dicks Hollow Rd, Winchester, VA 22603
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  /31

  $699,900 Coming Soon

  • 6 Beds
  • 4.5 Baths
  • 3,664 Sq Ft

  461 Skylar Lanes Way, Winchester, VA 22603

  Welcome to 461 Skylar Lanes Way, a stunning home nestled on over 2 acres in the upscale & sought after Walnut Springs Estates community, just minutes from downtown Winchester! This spacious residence offers 6 bedrooms, 4.5 bathrooms, and a 3-car side load garage with a circular paved driveway, providing plenty of room for family, guests, and entertaining. Step inside the foyer where you will find

  Michele Gibson Samson Properties

  461 Skylar Lanes Way, Winchester, VA 22603
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  /6

  $225,000

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

  0 N Frederick Pike Unit VAFV2038096, Winchester, VA 22603

  Just 7 miles/minutes from Winchester Medical Center and 10 miles from downtown Winchester, this 15-acre parcel offers privacy and convenience in one. The land features rolling hills, unlogged mature hardwood forest, and mountain views, with a gravel driveway crossing a private bridge into a secluded, untouched setting. Zoned residential, agricultural, and potentially commercial, it’s ideal for

  Kristina Towns Weichert Realtors - Blue Ribbon

  0 N Frederick Pike Unit VAFV2038096, Winchester, VA 22603
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  /3

  $3,200,000

  • Land
  • 8.65 Acres
  • $369,942 per Acre

  0 0 Northwestern Pike, Winchester, VA 22602

  Prime opportunity on 13.05 acres in an unbeatable high-visibility location along Route 50 in Winchester, VA. Positioned directly across from major retailers and conveniences—including Walmart, Sheetz, Tractor Supply, Applebee’s, Dunkin’, Bojangles, and the Winchester Medical Center campus—this property offers exceptional exposure and accessibility. Zoned for multiple development possibilities,

  Sarah Reynolds Keller Williams Realty

  0 0 Northwestern Pike, Winchester, VA 22602
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  /21

  $80,000

  • Land
  • 1 Acre
  • $80,000 per Acre

  852 Cedar Grove Rd, Winchester, VA 22603

  NEW LISTING Wooded 1 Acre lot on Cedar Grove Rd. Winchester, VA. Mature hardwoods on a gently sloping lot. Well is located on the front of the parcel, with no known septic letter. Old travel trailer on the lot.

  Wendy Conner Coldwell Banker Premier

  852 Cedar Grove Rd, Winchester, VA 22603
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  /16

  $349,999

  • 5 Beds
  • 2 Baths
  • 3,378 Sq Ft

  3339 N Frederick Pike, Winchester, VA 22603

  5 Wooded Acres with a pond – 7 miles/minutes from Winchester Medical CenterLarge 5-bedroom, 2-bath brick home on 5 wooded acres features its own pond, and a creek with bridge and asphalt driveway. Property offers fishing, wildlife, and privacy just minutes from Winchester Medical Center and downtown.Home requires major renovation and is being sold strictly as-is. Cash or renovation

  Kristina Towns Weichert Realtors - Blue Ribbon

  3339 N Frederick Pike, Winchester, VA 22603
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  /28

  $150,000

  • Land
  • 5.1 Acres
  • $29,412 per Acre

  0 Hedrick Ln, Winchester, VA 22602

  5.10 Unrestricted Private Acres with Electric, Septic, and Foundation – Ready to Build! Opportunities like this don’t come along often, this beautiful 5.10 acre lot features mature hardwoods and valuable improvements already in place, offering a jump start on your dream build. The property includes an installed 24' x 50' foundation w/ a walk-out basement, an installed three-bedroom septic system,

  Erik Thorpe ERA Valley Realty

  0 Hedrick Ln, Winchester, VA 22602
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  /71

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  4403 Back Mountain Rd, Winchester, VA 22602

  Nestled on two private wooded acres, 4403 Back Mountain Road in Winchester, VA offers a peaceful country retreat with no HOA or restrictions. Built in 2001, this traditional Colonial-style home features approximately 2,012 square feet of comfortable finished living space, including three bedrooms and two and a half baths . The walk-out basement provides excellent storage and potential for future

  RoxAnn Grimes RE/MAX Roots

  4403 Back Mountain Rd, Winchester, VA 22602
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  /46

  $599,900

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  289 Westview Dr, Winchester, VA 22603

  Welcome to your private contemporary retreat at 289 Westview Drive in Winchester, VA! This truly exceptional property offers the ultimate escape, situated on over 13 magnificent acres with gorgeous mature trees, stunning views, and unparalleled peace and quiet. Step inside the sun-filled main level, featuring an open layout that seamlessly connects the living room, dining room, and kitchen.

  Dan Whitacre Colony Realty

  289 Westview Dr, Winchester, VA 22603
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  /42

  $439,000

  • 3 Beds
  • 2 Baths
  • 2,325 Sq Ft

  1133 Tomahawk Trail, Winchester, VA 22602

  Nestled in the serene Shawneeland community, this exquisite chalet-style residence offers a perfect blend of rustic charm and modern comfort. Set against a backdrop of breathtaking mountain views and scenic vistas, this home is a sanctuary for those seeking tranquility and an exclusive lifestyle. As you approach the property, the warm cedar exterior invites you in, exuding a sense of timeless

  Sue Goodwin Long & Foster Real Estate, Inc.

  1133 Tomahawk Trail, Winchester, VA 22602
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  /37

  $259,900

  • 3 Beds
  • 2 Baths
  • 931 Sq Ft

  309 Raccoon Dr, Winchester, VA 22602

  Move in ready 3 bedroom 2 full baths home nestled in the woods that comes with additional lots(2) that can be built on or kept as a privacy buffer and equates to an acre or so. House features hardwood flooring and lots of knotty pine for that rustic look. Living room features a wood burning fireplace that is capable of heating the entire house and there is plenty of free down wood on the lot

  James Amick RE/MAX Roots

  309 Raccoon Dr, Winchester, VA 22602
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  /86

  $2,125,000

  • 5 Beds
  • 4 Baths
  • 4,166 Sq Ft

  1631 Back Mountain Rd, Winchester, VA 22602

  This unique property is the definition of an oasis in the woods. Surrounded by 180 glorious private acres, this home dazzles with grandeur while blending natural elements that mesh with the environment. The handsome hunter green standing seam metal roof with matching accents against wood siding is the ideal look for this 4,166 square foot architectural marvel. Indoors, there’s a thoughtful

  Dan Whitacre Colony Realty

  1631 Back Mountain Rd, Winchester, VA 22602
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  /3

  $1,200,000

  • Land
  • 2.38 Acres
  • $504,202 per Acre

  0 Prosperity Dr, Winchester, VA 22602

  2.38 Acres at the intersection of Valley Pike and Prosperity Drive. Located in the Kernstown area of Frederick County/Winchester. Property is located across from the street from CMA Honda, Aldi Supermarket, Outback Steakhouse, and Carrabba's Italian Grill & Restaurant. Located in close proximity to the intersection of I-81, US Route 37, and US Route 11. Excellent signage opportunities,

  H. Paige Manuel Oakcrest Commercial LLC.

  0 Prosperity Dr, Winchester, VA 22602
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  /62

  $1,200,000

  • Land
  • 124 Acres
  • $9,677 per Acre

  0 Frog Hollow Rd, Winchester, VA 22603

  Here’s a piece of pristine land on the market for the first time since the late 70’s with nearly endless possibilities for the next owner(s). This property is located north of Winchester and very near the West Virginia line. This prime piece of real estate has been family owned and operated for decades. Mix of mostly flat hay ground and wooded acreage that stretches to the top of North Mountain.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Frog Hollow Rd, Winchester, VA 22603
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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 Corcoran McEnearney

  LOT 5A Fox Trail, Winchester, VA 22602
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  /38

  $77,699

  • Land
  • 6.09 Acres
  • $12,758 per Acre

  440 Iris Ln, Winchester, VA 22602

  Enjoy breathtaking, unrivaled views of the Shenandoah Valley below from this ridgetop property on Little North Mountain.-Gorgeous Sunset Valley Views-Two Lots in One – Build on Both or Split Off!-Extensive Road Frontage-Power along Road-Very Buildable, No Floodplain or Wetlands-“Goldilocks” Location – countryside serenity, yet just 15 mins from downtown

  Ralph Harvey ListWithFreedom.com

  440 Iris Ln, Winchester, VA 22602
• 

  

  /51

  $1,595,000

  • Land
  • 158.44 Acres
  • $10,067 per Acre

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602

  Incredible opportunity to own 158.443 acres of pristine, private land in an exclusive 3-lot, 440-acre subdivision. This is the most secluded parcel of the three, offering unmatched 360-degree panoramic views and a level of privacy that’s increasingly rare—yet just 15 minutes from town. Tucked away from the lights and sounds of civilization, this property provides a peaceful, off-the-beaten-path

  Nadeem Helfer Corcoran McEnearney

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602
• 

  

  /42

  $1,550,000

  • Land
  • 128.56 Acres
  • $12,057 per Acre

  Lot 1 (128.556 Acres Laurel Grove Rd, Winchester, VA 22602

  Welcome to a truly rare offering — a first-time release of an extraordinary 128+ acre estate parcel, perfectly suited for the discerning buyer seeking privacy, natural beauty, and limitless potential. This is one of only three exclusive lots masterfully curated from a 439-acre legacy estate, designed with elegance, intention, and long-term value in mind.Tucked behind private, impeccably

  Nadeem Helfer Corcoran McEnearney

  Lot 1 (128.556 Acres Laurel Grove Rd, Winchester, VA 22602

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