Winchester, VA Homes for Sale with Acreage

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  /79

  $860,000

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

  150 Ewell Dr, Winchester, VA 22602

  Price Reduction- Welcome to Equestrian Estates, a highly sought-after Winchester community with no HOA, where space, style, and flexibility come together beautifully. This stately 5-bedroom, 6-bath Colonial offers over 6,700 square feet of finished living space on nearly 3 private acres, creating the perfect setting for both everyday living and entertaining. Originally built in 2007 and

  Sherry Santmyer Hunt Country Sotheby's International Realty

  150 Ewell Dr, 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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  /30

  $232,750

  • Land
  • 23.44 Acres
  • $9,930 per Acre

  0 Easter Ridge Lot 7 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. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. There are potential building sites located throughout the

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Easter Ridge Lot 7 Ln, Winchester, VA 22603
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  /11

  $1,100,000

  • Land
  • 2.83 Acres
  • $388,693 per Acre

  2725 S Pleasant Valley Rd, Winchester, VA 22601

  Location, location, location. Here is your chance to own one of the few commercial/industrial lots located in the highly desirable Winchester City. This cleared, blank slate is ready for your next business endeavor. Currently zoned as CM-1 (Commercial/Industrial), the property offers roughly 465 ft of prime road frontage, perfect for displaying your establishment.Current use regulations

  Kaitlyn Behr Samson Properties

  2725 S Pleasant Valley Rd, Winchester, VA 22601
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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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  /14

  $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 it’s ideal for building a custom home, a

  Kristina Towns Weichert Realtors - Blue Ribbon

  0 N Frederick Pike Unit VAFV2038096, Winchester, VA 22603
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  /8

  $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

  $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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  $1,095,000

  • 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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  /2

  $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

  $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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  /48

  $850,000

  • 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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  /48

  $999,999 New Construction

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

  2225 Cedar Grove Rd, Winchester, VA 22603

  12-17-25 foundation getting ready to be installed. A Private, Unrestricted Sanctuary 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 remains entirely

  Jim Thomson Realty ONE Group Old Towne

  2225 Cedar Grove Rd, Winchester, VA 22603
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  /3

  $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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  /42

  $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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  /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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  /73

  $849,900

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

  199 Meeting House Dr, Winchester, VA 22602

  Welcome to this spacious 5-bedroom, 4.5-bath home offering over 3,700 sq. ft. of finished living space seated on almost 3 and 1/2 acres . This property has been thoughtfully updated throughout, with new bathrooms, updated kitchen, new carpet, fresh paint, and numerous additional improvements—too many to list. The main-level primary suite features an en-suite bath with a soaking tub, dual vanity,

  Katie Deskins Century 21 Redwood Realty

  199 Meeting House Dr, Winchester, VA 22602
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  /57

  $300,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  124 Arrowhead Trail, Winchester, VA 22602

  Welcome home to 124 Arrowhead Tr., Winchester, VA, a charming retreat nestled on 1.25 acres in the sought-after Shawnee Land community. This inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort, character, and space to enjoy the outdoors.Step inside to an open-concept living and kitchen area designed for both everyday living and entertaining. The living room is filled with

  Lindsay Barnhart NextHome Realty Select

  124 Arrowhead Trail, Winchester, VA 22602
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  /2

  $209,900

  • Land
  • 5.06 Acres
  • $41,482 per Acre

  3900 Hunting Ridge Rd, Winchester, VA 22603

  Discover the perfect blend of seclusion and convenience on this 5.06-acre lot, already equipped with electric access, a well, and septic—ready for your dream home or recreational getaway. Tucked away in a serene and private setting, this lot offers easy access to nearby amenities and is ideal for those seeking tranquility without sacrificing convenience. Whether you’re planning to build your

  Natalie Dalecky ERA Oakcrest Realty, Inc.

  3900 Hunting Ridge Rd, Winchester, VA 22603
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  /16

  $329,000

  • 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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  /63

  $949,000 Open Sat 2:30PM - 4:30PM

  • 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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  $1,335,000

  • Land
  • 140.54 Acres
  • $9,499 per Acre

  0 Wardensville Grade Unit VAFV2023748, Winchester, VA 22602

  Dreaming of your own private escape in the mountains? This incredible 140+ acre property on Wardensville Grade offers the kind of peace and privacy that’s hard to find anymore. Whether you’re looking for a quiet retreat, a place to build your dream home, or land to explore and enjoy, this property gives you all of that — and more. Imagine waking up to nothing but the sound of birds and the breeze

  Kristi Cooper Realty ONE Group Old Towne

  0 Wardensville Grade Unit VAFV2023748, Winchester, VA 22602
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  /34

  $1,485,000

  • 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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  /47

  $1,099,900

  • 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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  /58

  $327,750

  • Land
  • 40.2 Acres
  • $8,153 per Acre

  0 Easter Ridge Lot 8 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 with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters via a loft. Experience exciting

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Easter Ridge Lot 8 Ln, Winchester, VA 22603
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  /11

  $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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  /36

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  372 Bethel Grange Rd, Winchester, VA 22603

  Spacious doublewide home offering endless potential, situated on 2.47 unrestricted acres in a prime Frederick County area. This 3-bedroom, 2 full bath home features a full unfinished basement, providing abundant space for storage, a workshop, or future expansion as some rooms are already framed in. The basement also includes a one-car garage, adding convenience and functionality. The home boasts

  Andrew Fultz Samson Properties

  372 Bethel Grange Rd, Winchester, VA 22603
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  /3

  $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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  /45

  $950,000

  • 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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  /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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  /15

  $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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  /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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  /7

  $200,000

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

  Lot C 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 C Cather Ln, Winchester, VA 22602
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  /12

  $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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  /73

  $444,900

  • 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 2.5 bathrooms. 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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  /17

  $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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  /62

  $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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  /4

  $849,999

  • 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
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  /77

  $559,000

  • 3 Beds
  • 2 Baths
  • 1,895 Sq Ft

  3904 N Frederick Pike, Winchester, VA 22603

  It's not often you find a home off of a public roadway on 10+ acres with its own pond and no subdivision to worry about. Bring your animals, and remember your fishing pole. There have been some nice fish caught over the years. This home is located close to town, but just rural enough to have land and privacy. 2 car front load garage is a great size and there's a garage at the rear of the house at

  Natalie Langford ERA Oakcrest Realty, Inc.

  3904 N Frederick Pike, Winchester, VA 22603

Showing Results 41 - 80, Page 2 of 2