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$24,900
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 approximately 20 minutes from Winchester. Road access is well maintained, with hard surface roads most of the way. A previous septic approval for a 4-bedroom Puraflo system (2006) is available in the documents; however, buyers should verify current requirements and updates with the county. Don’t miss the opportunity to own a mountaintop homesite in Shawneeland with incredible potential.

Lot 162 Bobcat Trl, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

$925,000
PLEASE NOTE THAT THERE IS AN ELECTRIC FENCE. PLEASE MAKE SURE IT'S CLOSED BEHIND YOU WHEN ENTERING AND EXITING PROPERTY. MUST HAVE AN APPOINTMENT AND BE ACCOMPANIED BY AN AGENT TO SEE THIS PROPERTY. A truly rare opportunity to own over 150 acres in Frederick Co., VA , just a few miles west of the scenic Shenandoah Valley—where rolling pasture, privacy, and possibility come together. 950 Stony Hill Rd. offers a stunning blend of open farmland and natural beauty. With significant portions of the land farmable, this property is perfectly suited for agricultural use, equestrian pursuits, or creating a remarkable private estate or multi-generational retreat. Development may be possible. Any Purchaser needs to do their own research for their desired use(s). Existing features include available electric and a former tenant house (not livable). This property is 15 minutes from Historic Old Town Winchester, featuring a wide array of shopping, dining and entertainment options. Year-round outdoor activity pursuits are possible on property or nearby, including, golfing, hiking, fishing, kayaking and even skiing within 2 to 2.5 hours. Must be accompanied by Agent and have appointment to tour property. Livestock on property. D0 NOT ENTER OLD TENANT HOUSE. IT'S NOT SAFE. ENTRY TO STUCTURE IS STRICTLY FORBIDDEN. Private property. No drive-bys.

950 Stony Hill Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$1,175,000
If you’ve been searching for space to breathe, this is it. Spanning 140.54 acres of wide-open and wooded land, this incredible property on Wardensville Grade offers the kind of peace, privacy, and freedom that’s getting harder to find. The moment you step onto the land, you’ll feel it, room to breathe, space to roam, and endless possibilities in every direction. There’s a beautiful homesite just waiting for you, perfectly positioned to overlook a peaceful pond. Imagine your future front porch here-morning coffee with mountain air, evenings filled with quiet sunsets, and nothing but the sounds of nature around you. Whether you’re looking to build your dream home, create a family compound, or design the ultimate weekend retreat, this land gives you the flexibility to do it your way. With NO HOA and NO restrictions, you have the freedom to build, farm, hunt, ride UTVs and four-wheelers, or even create your own private shooting range. No one telling you what to do, just land that works for your vision. Spend your days exploring your own trails, watching wildlife, or simply unplugging from the noise of everyday life. With a mix of open fields and wooded acreage, you get both stunning views and natural privacy, ideal for a homestead, hunting property, or long-term investment. And while it feels like a true getaway, you’re still conveniently located within reach of Winchester and major routes like 522, I-81, and I-66, making commuting or weekend trips easy. This is more than just land, it’s a chance to build something lasting. A place to gather, grow, and create a legacy for generations to come. Big land. Big sky. Endless potential.

Wardensville Grade, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

$410,000
Gentle stretches of open meadow roll into quiet, wooded groves where sunlight filters through the trees. Hidden among them, peaceful little ponds shimmer like jewels, inviting you to pause and simply breathe. Imagine sundrenched mornings, afternoons exploring your own private trails, and evenings watching the sky glow across wide open fields. Whether you long to build a cozy retreat, a forever home, or simply claim a sanctuary all your own, this land is more than just property—it’s a feeling, a place where serenity and possibility meet.” With plenty of space to roam, relax, and breathe freely, it’s the perfect backdrop for the lifestyle you’ve been waiting for.” Escape to a serene retreat of rolling meadows, shady woodlands, and sparkling little ponds. Here, the land is alive—deer wander gracefully through the trees, wild turkeys stride across the fields, and songbirds fill the air with music. Bring your horses, cows, goats, or sheep to graze the open pastures, or simply enjoy the peace of living alongside nature. This is more than just land—it’s a private sanctuary where farm life, wildlife, and natural beauty come together in perfect harmony.” In the summer, kids might toss in a line, pulling out a perch or even a fat catfish. Families might watch dragonflies skimming the water’s edge. At night, fireflies light up the grasses around the pond, adding to the magic.

000 Light Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: (540) 665-0360

$20,000
Tucked into the scenic mountains of Wilde Acres subdivision, this 0.81-acre offering combines three wooded lots into one unique opportunity for your future homesite or getaway retreat. Surrounded by mature trees and natural beauty, the property offers privacy, flexibility, and the potential to build in a peaceful setting away from the noise of town. Whether you're looking to create a full-time residence, weekend escape, or long-term investment, this property delivers. Located just 30 minutes from Winchester, you’ll enjoy convenient access to shopping, dining, and everyday amenities while still feeling tucked away in the mountains. Outdoor enthusiasts will appreciate the close proximity to George Washington National Forest, offering endless options for hiking, camping, and exploring. With three lots combined, you have added flexibility for building, layout, and future use - making this a rare find in a growing area. If you’ve been searching for a private, wooded setting with access to both nature and convenience, this is your opportunity.

Lot 9, 11, 13 Cougar Trail, Winchester

Listing courtesy of Connexa Real Estate. Contact:

$99,900
Unbelievable opportunity to own one of the few remaining buildable waterfront lots in this highly sought-after 24/7 gated lake community! Enjoy endless amenities including boating, water skiing, a fishing pier, sports courts, dog parks, a clubhouse with fitness room, and three sandy beaches. Conveniently located just 20 minutes from Winchester and 90 minutes from DC, this community is truly the area’s hidden paradise.Don’t miss your chance to secure an affordable piece of lakefront living—opportunities like this are rare! Buyers may apply for a personal-use dock through the HOA, subject to approval and guidelines. Marina boat slips are available separately and assigned by lease. Water and sewer hookups are available through Aqua for a current total cost of $5,000.

1235 Lakeview Dr, Cross Junction

Listing courtesy of Colony Realty. Contact:

$49,900
Rare opportunity to own a waterfront buildable lot at the end of a peaceful cove—at an unbelievable price! Whether you’re dreaming of a weekend retreat or your forever home, this property offers the perfect setting to enjoy everything Lake Holiday has to offer. This sought-after 240-acre gated lake community features boating, water skiing, fishing, a fishing pier, sports courts, 3 beaches, a clubhouse with fitness room, and scenic walking and hiking trails. Just 20 minutes from Winchester and 90 minutes from DC, Lake Holiday Estates is the area’s only 24/7 gated community. Don’t miss your chance to own a slice of paradise! No private dock currently exists on the property. Buyers may apply for a personal-use dock through the HOA, subject to approval and guidelines. Marina boat slips are available separately and assigned by lease. Water/sewer utility costs are presently available for hookup with Aqua at a total cost of 5k.

1231 Lakeview Dr, Cross Junction

Listing courtesy of Colony Realty. Contact:

$165,000
More Pictures On The Way! Now Offering This Beautiful Lot In Shawneeland VA, Just West Of Winchester! Mountain Top Lot With Great View! Lot Is Cleared, and Neighbors Lot Is Also! Clear View Of The Winchester City Area And Beyond! This .44 Acre Lot Has A Cleared Area With A Standing Shed, A 3 Bedroom Septic Perk, And Power Is Already Run On This Road. Mountain Top Living Includes The Frederick County Sanitary District To Take Care and Maintain The Roads Year Around. Its Not In An HOA) All Rules And Regulations Are Set By Fredererick County VA. Sanitary District Means That Frederick County Employs People To Keep Roads Clear In All Seasons, Mow The Common Areas, Keep Playground And Lake Beach Areas Clean, Keep Mailbox Areas Clean And Repaired and More! Internet Is Available At The Top Of The Mountain From Several Resources: Plenty Of People Work From Home In The Subdivision. Make Appointment Today

Lot 115 Rockwood Trl, Winchester

Listing courtesy of Coldwell Banker Premier. Contact: 990007.lead@leads.leadrouter.com

$140,000
Price Improvement! Tucked at the end of a quiet cul-de-sac, this 5.52 acre wooded lot offers the kind of setting many buyers hope to find but rarely do. The property sits slightly elevated above surrounding lots, creating a natural homesite with views and a peaceful sense of privacy. Mature trees provide a beautiful wooded backdrop without heavy underbrush, making it easy to walk and envision where your home could be built. One standout feature is a large, established oak tree that would sit perfectly alongside a future homesite, if desired. It would be a great natural focal point for the property and also add shade and character. With a gentle slope and multiple building locations, the lot offers flexibility for designing your home while taking advantage of the views and the surrounding landscape. Paved roads lead all the way to the property, and there is no HOA! This means you can enjoy the freedome of a rural setting while still being part of an established neighborhood. The location is within easy reach of some of the area's most popular outdoor destinations. Spend the day hiking, golfing, swimming, or relaxing at Cacapon Resort State Park, explore the shops and spas at Berkeley Springs, or enjoy the restaurants, shopping and historic charm of Winchester. For those commuting or seeking a weekend retreat from the city, the property is within a manageable drive of Northern virginia, making it a great option for a full-time residence or a peaceful getaway home. The property covenants require a minimum home size of 1,600 square feet for a one-story home or 1,800 square feet for a two-story home (excluding porches, garages, and basements). A well and septic system will be needed. If you've been searching for land that combines privacy, natural beauty, and convenience to nearby towns and outdoor recreation, this property is well worth exploring! Plat and full set of covenants and restrictions available.

LOT 18 - Loop Court, Cross Junction

Listing courtesy of Real Broker, LLC. Contact: 8504500442

$20,000
What a Great Find in Shawneeland! .46 Almost 1/2 acre Corner Lot, with most of the road frontage on Maple Trail, with a nice stream that runs along the back end of the property, if facing Maple Trail. If you enjoy mountain views, and amenities with No HOA, this would be a perfect location to build your potential full or part time home. Amenities include Cherokee lake w/ boat ramp (no gas motors) Beach Area, Large recreational Park Areas with streams and 2 fishing ponds, playground, pavilion, golf pads, basketball hoop, baseball field, streams, Larger fishing pond on Tecumseh & a smaller park area on Maple. Covered lighted mailbox buildings. Sheltered school bus stops. Live rural yet still a close distance (about 20 minutes) to Schools, shopping, Hospital and downtown Winchester.

LOT 245 Inca Trl, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

$50,000
WATER FRONT LOT with EXPOSURE to the WIDE OPEN part of the LAKE with views of the MAIN BEACH and CLUB HOUSE diagonally to the west across the lake. A quiet and peaceful setting for all your outdoor and lake activities. A unique opportunity to enjoy the elevated view of beautiful Lake Holiday - a pristine 240 Acre Lake only 15 minutes NW of Winchester Va,. This lot takes in the wide lake views and to the left you can see Beach 1. This is a membership parcel and not buildable, used for recreation and accessed via a solid gravel road. You will travel only 1 mile on gravel to reach this elevated parcel with a gentle slope about 2/3's into the lot before the topography gets a little steeper down to the lake. Set up your picnic table and grill here to take in the hot summer day cookouts under the shade trees, and enjoy jumping into the lake - or bring your kayak paddle around the many unique lake coves with an abundance of wildlife. There lake is also great for fishing, waterskiing and any other water activities. Lots of shade trees, and the lot could be improved by some light clearing to bring in more of the lake views. We have a local crew available for this sort of work should you be interested.

Southwood Dr-Lake Front, Cross Junction

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (540) 662-3484

$450,000
Unique lake front double lot with water and sewer availability. Both lots are on quiet waterfront on a finger of Lake Holiday. These are sheltered water front lot which avoid weather created waves and wake from main lake and recreational boat traffic. One lot has a natural docking area and the other has enough open water for a dock. Water is quiet area is safe for docking a motor boat, swimming, canoeing, kayaking. Unlike so many the lots that have steep inclines adjacent to the water; these lots have level land adjacent to the water which is a safer environment for children. Other steep lots with precipitous drops with as many as 100 steps to climb to the road. These two lots have a combined water frontage of 150 feet on the water. These lots are the only available waterfront property with road access to the water level. The road/driveway gives added value. Other homes recently built on the waterfront on steep lots have had to spend considerable amount of money (50K-100K) to excavate a driveway, provide drainage, and build expensive retaining wall between the house and the water. The lots are wooded with mature trees. Lake Holiday is a gated environmentally conscious community with security, club house, beach, marina, tennis and basketball courts, recently open family activity area with horseshoe pits, bocce ball court, frisbee golf course and hiking trails. The 240-acre lake has recreational boating for power boats under 21 feet on one half and a not wake area on the other half for canoeing, kayaking, crewing anchoring and fishing. The lake is stocked with bass, and wall eye. In mid-June the water temperature warms up quickly to 70 degrees and at most 80 degrees in August and returns to 70 by mid-September when days are shorter. Air temperature area runs 5-10 degrees cooler than Winchester and the Washington area. Summer days are 70-90 degrees. The summer nights are cooler 60-80 degrees. Lake Holiday is 2 hours from the Washington beltway. One has to drive 4 hours to get to Deep Creek Lake where the water tends to be cold most of the summer. Mount Storm is also 4 hours from the Washington Beltway. Lake Holiday is your closest lake for recreational boating west of Washington DC. Call today for a private showing.

Lakeview, Cross Junction

Listing courtesy of Realty ONE Group Old Towne. Contact: 5407738475

$141,500
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 is the next to last lot on Hodges Lane. Stellar views of the surrounding countryside are attainable with some tree clearing. This property features mildly sloping topography and a wet weather stream. Remote, fully wooded, and zoned Rural Areas (RA). Enjoy hiking, camping, and recreation of all types on this land. A short drive from all the amenities and attractions Winchester has to offer. ***Additional adjoining acreage available for purchase. See aerials for details.***

Lot 16 Hodges Ln, Winchester

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact: 2172859000

$549,000
Rare opportunity in the heart of Middletown! Discover the perfect blend of small-town charm, open space, and future potential on this beautiful 8-acre property surrounded by scenic pastureland and mountain views. Currently used for cattle and hay production, the land is partially fenced and includes a shed, making it ready for agricultural use or the ideal setting for your own private farmette—bring your animals and start living the country lifestyle. Imagine building your dream home while enjoying the peace and wide-open space this property provides. With town water and sewer hookups available or you could do well & septic - depending on costs . you’ll have the convenience of municipal services while still enjoying the feel of rural living. Zoned RA, the parcel may offer up to three homesites (buyer to verify)—perfect for a family compound, custom home sites, or a long-term investment opportunity. Located just a short walk to historic Main Street, you can easily enjoy local restaurants, shops, and community events. Plus, I-81 is only minutes away, making commuting simple while you return home each day to your peaceful countryside retreat. Opportunities like this are hard to find in Middletown. Schedule your showing today and explore the possibilities this special property offers. Property sold as-is. Buyer to verify subdivision potential, utilities, and zoning. Property is currently in land use; rollback taxes may apply if removed. Livestock on property—showings by appointment with agent accompaniment only. The purchaser could choose to do well & septic instead of hooking up to the public utilities Q: Where is Middletown, Virginia located? A: Middletown is located in the scenic Shenandoah Valley of Virginia, just south of Winchester and minutes from Interstate 81. Q: What makes Middletown a desirable place to live? A: Middletown offers small-town charm, historic character, and beautiful mountain views while still being close to shopping, dining, and commuter routes. Q: What outdoor activities are nearby? A: Residents enjoy easy access to hiking, fishing, and exploring the Shenandoah Valley, as well as nearby parks, rivers, and scenic mountain drives. Q: Is Middletown convenient for commuters? A: Yes. With quick access to I-81 and nearby Route 11, Middletown provides a convenient commute to Winchester and surrounding Shenandoah Valley communities. Q: What is the lifestyle like in Middletown? A: The town is known for its welcoming community, historic Main Street, seasonal events, and peaceful rural surroundings that make it a great place to enjoy the Shenandoah Valley lifestyle.

Veterans - Lot 12 Rd, Middletown

Listing courtesy of Sager Real Estate. Contact:

$725,000
Options galore! Purchase or ground lease with potential seller financing for a qualified purchaser. I-81 Exit #302 is the Gateway entrance into the Historic Town of Middletown, Virginia. This is the last remaining lot at the corner of Reliance Road and Valley Ave (Rt #11). We have 3.84 acres zoned B2 highway commercial. You are surrounded by The Village at Middletown by Ryan Homes. Richmond American Homes are building 90 additional single family homes on the south end of town. Middletown is home to Historic Wayside Inn, circa 1797, Laurel Ridge Community College with 3,500 students and staff. Immediate neighbors include; Comfort Inn, McDonalds, Dollar General, 7-11, Liberty C-store with fuel depot, Sheetz C-store with fuel depot has recently opened on the east side of the interstate. Locate your successful business venture where the growth is happening.

Reliance, Middletown

Listing courtesy of Commercial Specialists. Contact:

$209,000
Zoned B2 (General Business) | 0.64 Acres (27,788 sq. ft) Prime Commercial Development Opportunity (Dealership Approved) ​The Opportunity ​Position your business at the heart of the Valley’s growth. This high-visibility lot is strategically located along the bustling Route 11 (Valley Pike) corridor, serving as a primary artery for Stephens City and Frederick County. With hundreds of new homes completed in the last 36 months and hundreds more currently under construction within a 3-mile radius, this site offers a massive, built-in customer base ready for new services. ​Key Property Features ​Total Size: Paved 27,788 sq. ft. (approx. 0.64 acres). ​Zoning: B2 (General Business) – One of the most flexible commercial designations in Frederick County. ​Ideal Uses: For due diligence defer to zoning link below. ​Automotive Dealership / Sales ​Fast Food or Sit-down Restaurant ​Retail Strip Center or Showroom ​Medical Office or Professional Services ​Bank or Financial Institution ​Strategic Location: Direct frontage on Valley Pike with easy access to I-81 and the regional retail hub. ​Growth Context ​This isn’t just a lot; it’s a gateway to an expanding community. The surrounding "busy corridor" has seen a surge in residential density, creating high demand for local retail, dining, and automotive dealerships. Capture the traffic of today and the growth of tomorrow. ​Zoning & Regulatory Information ​The B2 General Business District is intended to provide for a wide variety of business, office, and service uses that require frequent and direct access by the general public. ​ Permitted Uses (Partial List): ​Motor Vehicle and Parts Dealers (Car Dealerships) ​Food Services and Restaurants (including Fast Food) ​Retail Trade (General Merchandising) ​Convenience Stores ​Personal Care Services (Salons/Barbers) ​Offices (Real Estate, Finance, Insurance) ​Official Links ​Frederick County Zoning Ordinance (B2 Section): View Section 165-603 ​ Full Frederick County Code of Ordinances: https://ecode360.com/13804443?hl=en-US

4937 Valley Pike, Stephens City

Listing courtesy of EXP Realty, LLC. Contact: 8883977352

$1,300,000
Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved Conditional Use Permit. Surrounded by nearby vineyards, farmers markets, and a wedding venue within a half mile, the location offers strong agritourism appeal. Enjoy gorgeous views and a peaceful rural setting, all while being just 10–15 minutes from downtown Winchester, grocery stores, and Winchester Medical Center. An exceptional opportunity for agricultural use, a private estate, or a thoughtfully planned preservation property in one of the Shenandoah Valley’s most sought-after locations.

Lot 7 Cedar Creek Grade, Winchester

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$165,000
Build your dream home on this beautiful waterfront lot in the private gated community of Lake Holiday Estates. This buildable parcel offers serene lake views and direct water access, creating the perfect setting for a full-time residence or weekend retreat. Enjoy lakeside living while taking advantage of Lake Holiday’s amenities, including the 240 acre recreational lake, beaches, boating, fishing, dog park, basketball courts, tennis courts, volleyball courts, and disc golf course. With paved roads, established utilities, and an easy drive to Winchester and surrounding commuter routes, this property combines natural beauty with everyday convenience. Lake Holiday is gated. Visitors must be accompanied by a realtor in order to see the property.

1065 Lakeview Dr, Cross Junction

Listing courtesy of Samson Properties. Contact: (540) 348-4911