Winchester, VA Homes for Sale with Acreage

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  /15

  $55,000

  • Land
  • 1.3 Acres
  • $42,308 per Acre

  LOT 152 Bobcat Trail, Winchester, VA 22602

  This lot is your perfect building spot if you are looking for the best views! Overlooking the mountain and plenty of semi cleared softly, sloped land, this lot is already perked for a 3 bedroom home and well site located. Originally three separate lots, it has been combined into a 1.3acre lot and is waiting for you to build your mountain retreat on.

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 782-3211

  LOT 152 Bobcat Trail, Winchester, VA 22602
• Explore Winchester

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  /34

  $449,900

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

  1420 Fishel Rd, Winchester, VA 22602

  ***Offering $11k towards Buyer's closing costs with ratified contract by 1.24.26*** Set back on a quiet, wooded lot, this move-in ready home offers comfortable one-level living in a private setting. The layout includes 3 bedrooms, 2 updated full baths, a bright eat-in kitchen, a spacious sitting area, and both a covered front porch and enclosed rear porch for added living space. You’ll appreciate

  

  Katherine (Kat) Wetzel

  Century 21 Redwood Realty

  (540) 551-7114

  1420 Fishel Rd, Winchester, VA 22602
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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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  /66

  $1,200,000

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

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603

  Heres a piece of pristine land on the market for the first time since the late 70s 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 of North

  Chad Pangle Whitetail Properties Real Estate

  0 Frog Hollow Rd Unit LotWP001, Winchester, VA 22603
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  /61

  $799,999

  • 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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  /9

  $730,000

  • 3 Beds
  • 2 Baths
  • 2,139 Sq Ft

  1491 Pitcock Ln, Winchester, VA 22602

  New house for the New Year! Welcome to 1491 Pitcock Lane, a spacious rancher set on 2 flat, partially wooded acres built by local builder Scott and Scott Construction. Walking in the front door, you are greeted by an open floor plan with luxury vinyl plank flooring throughout. Just off the entry, a dedicated office provides the perfect work-from-home or flex space. The kitchen features timeless

  Kaitlyn Behr Samson Properties

  1491 Pitcock Ln, Winchester, VA 22602
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  /6

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot B Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr Samson Properties

  Lot B Cather Ln, Winchester, VA 22602
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  /11

  $4,000,000

  • Land
  • 19 Acres
  • $210,526 per Acre

  368 Victory Rd, Winchester, VA 22602

  19 Acres, Prime Commercial or FLEX Development Opportunity! Zoned B2, General Commercial. Major commuter corridor to Northern VA, adjacent to Airport Business Park, FBI Records Center, Navy Federal Credit Union headquarters, and new One Logistics Park. Also #1 commuter route to Northern VA! Excellent visibility, flat topo, and dual access on Victory Lane and Independence! Sale includes 14.06

  Gillian Greenfield Coldwell Banker Premier

  368 Victory Rd, Winchester, VA 22602
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  /80

  $599,000

  • 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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  /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, Stainless

  Brett Sowder RE/MAX Roots

  6 Dicks Hollow Rd, Winchester, VA 22603
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  /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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  /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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  /9

  $166,000

  • Land
  • 59.93 Acres
  • $2,770 per Acre

  0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602

  UNIQUE 60 ACRE WOODED TRACT within the Great North Mountain Wilderness Area enhanced by County maintained hard surfaced road access and available electricity. The Offering also includes a contiguous half acre building Lot (Shawneeland - Tax ID 49-A05-1-W-1) which is located adjacent to the main tracts access point at the intersection of Tomahawk and Jalapa. Potential forty plus mile views

  Wayne Wilson Thomas and Talbot Estate Properties, Inc.

  0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602
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  /24

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  129 Jalapa Trail, Winchester, VA 22602

  Mountain Views & Modern Perfection: Your Turnkey Retreat Awaits!Seller offering buyer credit Welcome to your completely renovated sanctuary at 129 Jalapa Trail, where breathtaking Virginia mountain vistas meet the peace of mind of brand-new everything. Nestled on a private 1.35-acre lot, this charming home is the perfect blend of rustic tranquility and modern convenience—just 7 miles from the

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
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  /98

  $419,000

  • 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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  /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
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  /44

  $319,000

  • 1 Bed
  • 1 Bath
  • 1,348 Sq Ft

  242 Footstone Ln, Winchester, VA 22603

  Peaceful Country Retreat on 4.7 Acres – Minutes from WinchesterThis private country home combines solid craftsmanship with serene mountain views. Located on a quiet gravel lane with a road maintenance agreement, the property features a durable stone-and-brick exterior and hardwood floors throughout. Inside, two stone fireplaces—including one in the primary bedroom—add warmth and character.

  Kristina Towns Weichert Realtors - Blue Ribbon

  242 Footstone Ln, Winchester, VA 22603
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  /7

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot A Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr Samson Properties

  Lot A Cather Ln, Winchester, VA 22602
• 

  

  /98

  $699,900

  • 6 Beds
  • 4.5 Baths
  • 4,124 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, with just minutes from downtown Winchester! This spacious residence offers 6 bedrooms, 4.5 bathrooms, finished basement and a 3-car side load garage with a circular paved driveway, providing plenty of room for family, guests, and entertaining. Step inside the

  Michele Gibson Samson Properties

  461 Skylar Lanes Way, Winchester, VA 22603
• 

  /2

  $500,000

  • Studio
  • 1,175 Sq Ft

  513 and 525 Monticello St, Winchester, VA 22601

  For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

  Brett Haynes Oakcrest Commercial LLC.

  513 and 525 Monticello St, Winchester, VA 22601
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  /17

  $169,900

  • Land
  • 49.61 Acres
  • $3,425 per Acre

  0 Rockwood Trail Unit 49.61 ACRES, Winchester, VA 22602

  A great many buyers are looking for decent acreage, views, the ability to hunt and shoot, the opportunity to get away on the weekends with privacy and with potential for a family retreat and maybe even future retirement. This listing clicks all the boxes. This one is on top the mountain with hard surfaced roads all the way to the top. The name of the subdivision is Great Mountain Wilderness.

  Edward Beightol Cedar Creek Real Estate

  0 Rockwood Trail Unit 49.61 ACRES, Winchester, VA 22602
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  /16

  $450,000

  • Land
  • 77 Acres
  • $5,844 per Acre

  92 Bobcat Trail, Winchester, VA 22602

  Calling all hunters or just someone who wants seclusion! This property has amazing views and already has a structure perfect to finish your way! Perfect for getting away from it all or long hunting trips. No septic or power to structure yet. Gate to enter property. Property has 2 pink flags at the beginning of property and runs all the way to the power lines.

  Daryl Stout RE/MAX Real Estate Connections

  92 Bobcat Trail, Winchester, VA 22602
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  /6

  $40,000

  • 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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  /23

  $99,900

  • Land
  • 15.9 Acres
  • $6,283 per Acre

  LOT 11-HOOVER MTN Pack Horse Rd, Winchester, VA 22603

  Unique property, great for recreation. Land is all wooded, tall hardwoods, mostly mountainside. There is about 1.5 acres where Little Mountain Run (creek) runs through the property for over 300' so that you have a very flat, wooded area on the other side of the creek which is perfect for hiking, camping, hunting. You will have to visit the property to really appreciate what it has to offer.

  Edward Beightol Cedar Creek Real Estate

  LOT 11-HOOVER MTN Pack Horse Rd, Winchester, VA 22603
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  /12

  $1,500,000

  • Land
  • 5.26 Acres
  • $285,171 per Acre

  153 Welltown Rd, Winchester, VA 22603

  5.26 Acres of Interstate/Commercial Land Lease Available, Frederick County, VA, Exit 317. Besides Taco Bell, across from new hotel, surrounded by commercial, connects to Crown Lane for traffic light access! Excellent visibility on Martinsburg Pike (39,000 AADT VDOT '17). Ideal for restaurant, fast food, grocery, auto parts retailer, auto repair. Strong potential for rezoning for increased

  Gillian Greenfield Coldwell Banker Premier

  153 Welltown Rd, Winchester, VA 22603
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  /7

  $499,000

  • Land
  • 17.98 Acres
  • $27,753 per Acre

  Lot 13 Tavistock Dr, Winchester, VA 22602

  Beautiful 17.98 acre Lot, approved for 3 bedroom perk, Tavistock Estates, one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

  Gillian Greenfield Coldwell Banker Premier

  Lot 13 Tavistock Dr, Winchester, VA 22602
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  /2

  $2,250,000

  • Land
  • 9 Acres
  • $250,000 per Acre

  280 Costello, Winchester, VA 22601

  Nine acres of B2 land near Costco, Army Corp of Engineers, Frederick Country Public Safety Building, and the new One Logistics Park commercial center. Perfect for a large-scale commercial development.

  Jason Aikens RE/MAX Roots

  280 Costello, Winchester, VA 22601
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  /13

  $649,900

  • Land
  • 1.75 Acres
  • $371,371 per Acre

  115 Dairy Corner Place, Winchester, VA 22602

  3 parcels of land to total 1.75 acres zoned B-2 in a great location right off I-81 and on Route 7 resulting in lots of exposure/high traffic area. Right next door to Walgreens. Approved for 10,000 sq ft of commercial space! Can easily be rezoned for apartments! Great opportunity. Currently has an income producing residential home on the lot. Will consider owner financing. Tax Map IDs: 54-9-2,

  Elizabeth Carroll ERA Oakcrest Realty, Inc.

  115 Dairy Corner Place, Winchester, VA 22602
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  /14

  $1,499,000

  • Land
  • 2 Acres
  • $749,500 per Acre

  1625 Amherst St, Winchester, VA 22601

  Introducing a fantastic development opportunity! This parcel features 2 flat acres of commercial land in a prime location. Located on a major thoroughfare into downtown Winchester and a half mile from Winchester Medical Center, this lot is ideal for your commercial venture. The lot offers excellent road frontage and good topography. Ideal for medical/dental office, office space, restaurant, or

  Dan Whitacre Colony Realty

  1625 Amherst St, Winchester, VA 22601
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  /12

  $165,000

  • Land
  • 7.4 Acres
  • $22,297 per Acre

  0 Back Mountain Road Lot 11, Winchester, VA 22602

  Enjoy beautiful views of the valley from this 7.4-acre private lot! Located just 15-20 minutes from downtown Winchester. Build a weekend getaway or the dream home you have always wanted. Easement to property from Back Mountain Road. See property docs attached.

  Sheila Pack RE/MAX Roots

  0 Back Mountain Road Lot 11, Winchester, VA 22602
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  /8

  $2,286,000

  • Land
  • 5.08 Acres
  • $450,000 per Acre

  0 Market St Unit VAFV2004914, Winchester, VA 22602

  5.08 Acres zoned B-2 in Rutherford Crossing shopping center. Owner will consider subdivision of the property. Directly across from Lowes and Target and next to Spring Hill Marriot Hotel and Suites and FEMA call center. Ideal for hotels, restaurants, office buildings, retail, etc... John Schroth and John Scully, owners are licensed Realtors in the state of Virginia.

  John Schroth Colony Realty

  0 Market St Unit VAFV2004914, 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 5 acre acre lot, offering endless possibilities for the right buyer.Adding the two lots together is 7.44 acres.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

  Mauricio Argandona Fairfax Realty Select

  220 Snappy Ln, Winchester, VA 22602
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  /22

  $399,000

  • 3 Beds
  • 2 Baths
  • 2,075 Sq Ft

  129 Jalapa Trail, Winchester, VA 22602

  Buyer Credit - This beautifully renovated traditional home in Shawnee Land offers a perfect blend of comfort and modern living. With 3 spacious bedrooms and 2 full bathrooms, the layout is designed for both relaxation and functionality. The interior features a breakfast area and a traditional floor plan, complemented by wood flooring throughout. The full daylight basement provides ample space for

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
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  /7

  $235,000

  • Land
  • 17.8 Acres
  • $13,202 per Acre

  0 Dr, Winchester, VA 22603

  Outstanding Opportunity – 17.80 Acres in Winchester, VAEmbrace the beauty and serenity of Virginia’s countryside with this expansive 17.80-acre parcel, ideally boarder's both sides of Snake Drive. The property showcases rolling topography and walkable terrain, offering a picturesque setting for your future home, weekend retreat, or recreational getaway.This parcel has an approved perk

  Jocelyn Tweedie Coldwell Banker Premier

  0 Dr, Winchester, VA 22603
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  /56

  $1,899,000

  • Studio
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  In town location for this completely remodeled multi unit property. This property contains 4 homes and 2 apartments that have been completely refinished. The main home is currently lived in by the owner and is attached to a indoor swimming pool. The other 3 homes and 2 apartments are leased and are bringing over$10,500 monthly. If you choose rent the main house income would be much higher. .

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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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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  /7

  $129,000

  • Land
  • 8.3 Acres
  • $15,542 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
• 

  

  /3

  $2,300,000

  • Land
  • 3.51 Acres
  • $655,271 per Acre

  1721 Amherst St, Winchester, VA 22601

  3.51 AC of premier commercial land. Directly across the street from the main hospital campus on one of Winchester's main commercial corridors. Ideal for banks, medical offices, retail or restaurants.

  Marie DiLorenzo Oakcrest Commercial LLC.

  1721 Amherst St, Winchester, VA 22601
• 

  

  /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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  /56

  $266,000

  • Land
  • 25.16 Acres
  • $10,572 per Acre

  0 Easter Ridge Lot 7a Ln, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Easter Ridge Lane. Features a fully functional hunting cabin wired for a generator hook up with propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters in an attached

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Easter Ridge Lot 7a Ln, Winchester, VA 22603

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