Winchester, VA Homes for Sale with Acreage

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  $579,900

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

  157 Oak Dr, Winchester, VA 22603

  Welcome home to 157 Oak Dr. in Winchester, VA—an inviting property offering comfort, thoughtful updates, and a peaceful setting. This home has been refreshed with luxury vinyl plank flooring throughout most of the home and fresh paint, creating a clean, move-in-ready feel. Be Sure to Watch The Video to Experience Even More of This Home!The primary suite has been remodeled, including an

  Phyllis Guthrie Keller Williams Realty

  157 Oak Dr, Winchester, VA 22603
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  $1,400,000

  • Land
  • 5.73 Acres
  • $244,328 per Acre

  1667 N Frederick Pike, Winchester, VA 22603

  Great highway exposure exposure to state route 37 the bypass around the West side of Winchester and and 5222 north or North Frederick Pike entrance at a signalized intersection

  John Scully Colony Realty

  1667 N Frederick Pike, Winchester, VA 22603
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  $2,525,100

  • Land
  • 8.86 Acres
  • $285,000 per Acre

  0 Kavanaugh Dr Unit VAFV2017570, Winchester, VA 22602

  8.86 Acres of undeveloped commercial land zoned B-2 with excellent US 37 future signage visibility, exposure, and location. All utilities available for connection. Approved uses include self-storage warehouses, distribution warehouses, car washes, new car dealerships, hotels and restaurants.

  Marie DiLorenzo Oakcrest Commercial LLC.

  0 Kavanaugh Dr Unit VAFV2017570, Winchester, VA 22602
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  $3,200,000

  • Land
  • 451 Acres
  • $7,095 per Acre

  472 Mccubbin, Winchester, VA 22601

  Adrian Small TTR Sotheby's International Realty

  472 Mccubbin, Winchester, VA 22601
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  $3,200,000

  • Land
  • 13.05 Acres
  • $245,211 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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  $850,000 New Construction

  • 5 Beds
  • 3 Baths
  • 3,057 Sq Ft

  Lot 5 Keval Gyan Way, Winchester, VA 22603

  Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of a large family living in this

  Jim Thomson Realty ONE Group Old Towne

  Lot 5 Keval Gyan Way, Winchester, VA 22603
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  $999,999 New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,100 Sq Ft

  Lot 52A Keval Gyan Way, Winchester, VA 22603

  2-20-26 house is ruffed in and insulated. Going to drywall next week. Delivery 4-6-26.At front of Keplinger Estates near the Apple Pie Ridge area.Seize a truly unique opportunity to own a brand-new, luxury estate set on over 7 acres of private, wooded land. While this stunning property sits at the entrance to the prestigious, upper-scale 15-lot Keplinger Estates community, it does not

  Jim Thomson Realty ONE Group Old Towne

  Lot 52A Keval Gyan Way, Winchester, VA 22603
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  $179,000

  • 2 Beds
  • 1 Bath

  777 McDonald Rd, Winchester, VA 22602

  1.22 Acres with Move-In Ready Mobile Home & Approved 3BR Build – Utilities Installed! Stop searching for land and start building! This is the ultimate "hook-up" property located on a quiet 1.22-acre lot, just minutes from downtown and shopping. Whether you want to move in immediately while you plan or start construction right away, this property has everything in place. The Land & Utilities:

  Kandi McKenzie Realty ONE Group Old Towne

  777 McDonald Rd, Winchester, VA 22602
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  $37,100

  • Land
  • 3.57 Acres
  • $10,392 per Acre

  0 Remington & Bluebird, Winchester, VA 22602

  John Holsinger JOHN S HOLSINGER REAL ESTATE BROKER LLC

  0 Remington & Bluebird, Winchester, VA 22602
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  $767,900

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

  1049 Laurel Grove Rd, Winchester, VA 22602

  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 the amin floor are large with great

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
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  $135,000

  • Land
  • 5.1 Acres
  • $26,471 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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  $1,500,000

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

  153 Welltown Rd, Winchester, VA 22603

  5.26 Acres of Interstate/Commercial Land SALE OR 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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  $834,900

  • 5 Beds
  • 4.5 Baths
  • 3,767 Sq Ft

  199 Meeting House Dr, Winchester, VA 22602

  Legendary Living on 3.46 Acres — 5BR Estate With Mountain Views, Luxe Updates & Iconic History Welcome to a truly one-of-a-kind estate offering over 3,700 sq. ft. of finished living space on nearly 3.46 acres, complete with mountain views, extensive updates, and a legendary past. This 5-bedroom, 4.5-bath home has been thoughtfully renovated throughout. The main level features a primary suite with

  Katie Deskins Century 21 Redwood Realty

  199 Meeting House Dr, Winchester, VA 22602
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  /2

  $250,000

  • Land
  • 5 Acres
  • $50,000 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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  $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 for a

  Jocelyn Tweedie Hunt Country Sotheby's International Realty

  0 Dr, Winchester, VA 22603
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  $929,900

  • 6 Beds
  • 5 Baths
  • 4,891 Sq Ft

  161 Skylar Lanes Way, Winchester, VA 22603

  STUNNING HOME WITH ACREAGE! Imagine having nearly 5,000 square feet of finished living space on two acres with no HOA - just 20 minutes from downtown Winchester!! This house is special - and you'll feel it as soon as you see it! 161 Skylar Lanes Way has been lovingly maintained, updated, and renovated. Absolutely no detail has been overlooked over the past few years!! This home features SIX

  Kristin Crosby Samson Properties

  161 Skylar Lanes Way, Winchester, VA 22603
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  $1,485,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,484 Sq Ft

  Lot 18 Honeycrisp Way, Winchester, VA 22603

  Remarkable and new to the market Anderson subdivision lots. Located 5 minutes from downtown Winchester and Valley Health Medical Center (2 minutes from James Wood High School) off Apple Pie Ridge. These lots feature panoramic views of the entire Shenandoah Valley from Harper's Ferry to Strasburg to the Western Mountains, providing stunning views from an elevated, very private environment. These 5

  JP Carr Merrifield Realty, LLC

  Lot 18 Honeycrisp Way, Winchester, VA 22603
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  $1,099,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 5,800 Sq Ft

  Lot 1 Keval Gyan Way, Winchester, VA 22603

  Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA.Experience the pinnacle of single-level living in this

  Jim Thomson Realty ONE Group Old Towne

  Lot 1 Keval Gyan Way, Winchester, VA 22603
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  $275,000

  • Land
  • 5.79 Acres
  • $47,496 per Acre

  LOT 1 - Handley Dr, Winchester, VA 22603

  Spring Valley Estates. A rare opportunity to find a 5-Acre lots within 5 minutes of downtown Winchester and the Valley Health Medical Center. James Wood High School and Apple Pie Elementary within a mile of this lot. Fully built lot with approved perc on file. Buyer can buy the lot and build their dream house or for future investment purposes. This corner lot is cleared with existing road

  JP Carr Merrifield Realty, LLC

  LOT 1 - Handley Dr, Winchester, VA 22603
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  $599,000

  • Land
  • 15.5 Acres
  • $38,645 per Acre

  0 Cedar Creek Grade Unit VAFV2036934, Winchester, VA 22602

  This exceptional 15.5-acre buildable lot on Cedar Creek Grade in Winchester, VA offers the perfect canvas for your dream home. With a premier location that balances peaceful seclusion with urban convenience, this property is just minutes away from shopping, restaurants, schools, and more. Its close proximity to Winchester Medical Center also makes it an ideal location for medical professionals or

  Dan Whitacre Colony Realty

  0 Cedar Creek Grade Unit VAFV2036934, Winchester, VA 22602
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  $3,025,000

  • Land
  • 27.09 Acres
  • $111,665 per Acre

  0 Renaissance Dr, Winchester, VA 22602

  27.09 +/- acres in the direct path of Light Industrial-Zoned land. The subject property is in the comprehensive plan to be zoned Light Industrial for warehousing, distribution, self-storage warehousing or light manufacturing. The 27.09 +/- acre site has excellent proximity and access to US 11, Route 37. and I-81. The property provides location, visibility, and exposure. All utilities are

  H. Paige Manuel Oakcrest Commercial LLC.

  0 Renaissance Dr, Winchester, VA 22602
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  $950,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 3,100 Sq Ft

  Lot 12 Keval Gyan Way, Winchester, VA 22603

  Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living in this immaculate,

  Jim Thomson Realty ONE Group Old Towne

  Lot 12 Keval Gyan Way, Winchester, VA 22603
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  $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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  $39,000

  • Land
  • 1.53 Acres
  • $25,490 per Acre

  Lot 10,11,12-13 A 60 Fox Trail, Winchester, VA 22602

  Attention Builders! 4 Pack of contiguous building lots in Wilde Acres -Mountain Falls Park, you have the opportunity to construct your very own mountain top retreat. Mountain Falls Park is conveniently located, just a short drive away from Stephens City or downtown Winchester, VA, providing an easy commute while still offering the seclusion and serenity of the mountains. Immerse yourself in

  Nadeem Helfer Corcoran McEnearney

  Lot 10,11,12-13 A 60 Fox Trail, Winchester, VA 22602
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  $369,900

  • Land
  • 11.49 Acres
  • $32,193 per Acre

  Lot 1 Tavistock Dr, Winchester, VA 22602

  Beautiful 11.49 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 1 Tavistock Dr, Winchester, VA 22602
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  /2

  $1,800,000

  • Land
  • 4.93 Acres
  • $365,112 per Acre

  0 Sulky Dr, Winchester, VA 22602

  4.93 acres with great interstate exposure. End of cul de sac. Owners have proposed platt showing parcel subdivided into 4 parcels

  Jeff Webber Long & Foster Real Estate, Inc.

  0 Sulky Dr, Winchester, VA 22602
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  /2

  $250,000

  • Land
  • 5.01 Acres
  • $49,900 per Acre

  Lot 7 Oak, Winchester, VA 22603

  Build Your Vision at the End of the LaneDiscover 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.

  Jim Thomson Realty ONE Group Old Towne

  Lot 7 Oak, Winchester, VA 22603
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  $1,550,000

  • Land
  • 152.44 Acres
  • $10,168 per Acre

  152.44 Acres Lot 2 Laurel Grove Rd, Winchester, VA 22602

  An unparalleled opportunity to own one of the most accessible yet private properties near the city of Winchester. Just under an hour and half from Dulles International Airport it is the perfect weekend escape in the countryside or full time residence. As you meander through the forest on the beautiful drive to the property you will become enchanted with your surroundings. This is one of 3

  Nadeem Helfer Corcoran McEnearney

  152.44 Acres Lot 2 Laurel Grove Rd, Winchester, VA 22602
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  $4,125,000

  • Land
  • 439.43 Acres
  • $9,387 per Acre

  439 Acres Laurel Grove Rd, Winchester, VA 22602

  Seize this extraordinary opportunity to own an impressive 439+ contiguous acres in the scenic heart of Winchester, VA—a once-in-a-lifetime investment beckoning those with grand visions. A minor rural subdivision of three magnificent estate lots approved. Each parcel will offer a tranquil escape, seamlessly accessible via a professionally engineered 50' right of way. These beautifully crafted

  Nadeem Helfer Corcoran McEnearney

  439 Acres Laurel Grove Rd, Winchester, VA 22602
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  /5

  $849,999 New Construction

  • 3 Beds
  • 2 Baths
  • 2,488 Sq Ft

  Lot 11 Keval Gyan Way, Winchester, VA 22603

  Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house (new PIN OAK model); it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of an HOA. Experience the pinnacle of single-level living

  Jim Thomson Realty ONE Group Old Towne

  Lot 11 Keval Gyan Way, Winchester, VA 22603

Showing Results 41 - 70, Page 2 of 2