Winchester, VA Homes for Sale with Acreage

• 

  

  

  /8

  $250,000

  • Land
  • 15.63 Acres
  • $15,995 per Acre

  15.63 Acres 52-2-b, Winchester, VA 22603

  15.63 +/- acres, located at the top of Round Hill, call for information about access, the property will be sold with deed restrictions against building at the top of the hill.

  John Scully Colony Realty

  15.63 Acres 52-2-b, Winchester, VA 22603
• 

  

  

  /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 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
• 

  

  

  /3

  $275,000

  • Land
  • 6.41 Acres
  • $42,902 per Acre

  LOT 27A - 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 road to the lot. No cert letter on file. Buyer can buy the lot and build their dream house or for future investment purposes.

  JP Carr Merrifield Realty, LLC

  LOT 27A - Handley Dr, Winchester, VA 22603
• 

  

  

  /3

  $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
• 

  

  

  /35

  $525,000

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

  157 Oak Dr, Winchester, VA 22603

  STOP THE PRESSES!! This PRICE ADJUSTMENT is not a typo! The weather is warmer and Spring is in the air.... This home is ready for YOU! 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,

  Phyllis Guthrie Keller Williams Realty

  157 Oak Dr, Winchester, VA 22603
• 

  

  /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 Samson Properties

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

  

  /80

  $795,000

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /3

  $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
• 

  

  /46

  $550,000

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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 Samson Properties

  LOT 5A Fox Trail, Winchester, VA 22602
• 

  

  /51

  $1,595,000

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

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

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

  Nadeem Helfer Samson Properties

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

  

  /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
• 

  

  /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
• 

  

  /42

  $767,900

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

  1049 Laurel Grove Rd, Winchester, VA 22602

  This custom-built 3-bedroom, 3-bath home is perfectly positioned on a private, wooded lot with sweeping mountain views and a sense of seclusion. The setting feels like a peaceful retreat, offering a serene, park-like atmosphere while still providing convenient access to everyday amenities. The main-level primary suite is a standout, featuring an elegant bathroom with a walk-in shower and a

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /56

  $1,850,000

  • 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. . Update, main house is now rented and income is over $15,000 per month. This property is also improved with large block garage and a separate 4 car garage with over 18' ceilings. Perfect for the automotive enthusiast or you can continue to

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
• 

  

  /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 Samson Properties

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

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /2

  $420,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  775 Pack Horse Rd, Winchester, VA 22603

  Completely remodeled and move-in ready, this charming property at 775 Pack Horse Road in Frederick County, VA offers the perfect blend of modern updates and peaceful country living. Situated on a picturesque setting, the home has been thoughtfully renovated throughout, featuring updated finishes, refreshed interiors, and attention to detail in every room. Enjoy the convenience of a detached

  Amanda Slate Keller Williams Realty

  775 Pack Horse Rd, Winchester, VA 22603
• 

  /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
• 

  /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
• 

  /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
• 

  

  /24

  $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
• 

  /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
• 

  /2

  $679,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  0 Tumble Leaf Ln, Winchester, VA 22602

  CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Main Level Living Evergreene model with standard 13' Family Rm Ceilings Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

  Daniel Boris Pearson Smith Realty, LLC

  0 Tumble Leaf Ln, Winchester, VA 22602
• 

  

  /26

  $799,900 New Construction

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

  169 Cather Ln, Winchester, VA 22602

  Estimated completion August 2026. Photos shown are of a similar home previously constructed by the builder. Finishes and features may vary. Welcome to 169 Cather Lane, a spacious rancher situated on 5 beautiful pastoral acres with stunning views and an unbeatable location just minutes from town. Built by local builder Scott & Scott Construction, this home offers the perfect blend of quality

  Kaitlyn Behr Samson Properties

  169 Cather Ln, Winchester, VA 22602
• 

  

  /38

  $849,900 New Construction

  • 3 Beds
  • 2 Baths
  • 2,512 Sq Ft

  Lot 13 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 (ASPEN 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 in

  Jim Thomson Realty ONE Group Old Towne

  Lot 13 Keval Gyan Way, Winchester, VA 22603

Showing Results 41 - 80, Page 2 of 3