Winchester, VA Homes for Sale with Acreage

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  /20

  $299,900

  • Land
  • 7.82 Acres
  • $38,350 per Acre

  TBD Gough Rd, Winchester, VA 22602

  Premium lot, ready to build on! This 8 acre parcel offers a rare combination of views, usable acreage, and convenience. Set approximately 800 feet off Cedar Creek Grade with frontage on Gough Road, the elevated homesite captures exceptional, wide-open mountain views and a peaceful, bucolic setting. Surrounded by farmland and in an area with attractive and newer, custom homes, this property feels

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 348-3423

  TBD Gough Rd, Winchester, VA 22602
• Explore Winchester

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  /9

  $1,300,000

  • Land
  • 64.91 Acres
  • $20,028 per Acre

  Lot 7 Cedar Creek Grade, Winchester, VA

  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

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 7 Cedar Creek Grade, Winchester, VA
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  /3

  $999,000 Coming Soon

  • 6 Beds
  • 3.5 Baths
  • 3,848 Sq Ft

  240 Glendobbin Rd, Winchester, VA 22603

  Nestled on a picturesque 7-acre lot, this Farmette is just minutes from downtown Winchester, offering the perfect blend of privacy, space, and convenience. Opportunities like this are rare—enjoy the tranquility of country living while remaining in one of the area’s most desirable and accessible locations.Inside, hardwood floors flow throughout the home, beginning with a grand entrance and

  

  Lori Bales

  Keller Williams Realty

  (540) 515-5065

  240 Glendobbin Rd, Winchester, VA 22603
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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
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  /50

  $1,200,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,284 Sq Ft

  80 Gough Rd, Winchester, VA 22602

  Dreaming of your own farmette, private estate, or peaceful country retreat?This is a rare opportunity to create what you're searching for on a premium 8-acre lot offering gorgeous mountain views, usable acreage, and a truly scenic setting. The elevated homesite sits approximately 800 feet off Cedar Creek Grade with frontage on Gough Road, providing privacy while still offering easy access to

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 781-0968

  80 Gough Rd, Winchester, VA 22602
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  /55

  $925,000

  • 4 Beds
  • 2.5 Baths
  • 2,894 Sq Ft

  247 Mcguire Rd, Winchester, VA 22603

  Extensively renovated in 2024 and privately situated on a peaceful 2.7-acre cul-de-sac lot, this stunning brick home offers a rare opportunity to own acreage, privacy, and high-end upgrades just minutes from Winchester amenities. Surrounded by mature trees and free from HOA restrictions, the property delivers an estate-like setting with modern finishes throughout. The entire home has been

  Jon Fleming Weichert Realtors - Blue Ribbon

  247 Mcguire Rd, Winchester, VA 22603
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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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  /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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  /8

  $785,000 New Construction

  • 3 Beds
  • 3 Baths
  • 2,548 Sq Ft

  0 Apple Pie Ridge Rd Unit VAFV2039276, Winchester, VA 22603

  Dogwood - One Story Living Carrington Homes Western Loudoun’sPremiere Home builder introduces its newWinchester Collection of single familyHomes on a private 2 acre lot.Custom style homes designedBy James McDonald Architects One story and two story plans withFirst floor multi generational options available DECORATED MODELS located at 156 Covey Lane Winchester

  Daniel Boris Pearson Smith Realty, LLC

  0 Apple Pie Ridge Rd Unit VAFV2039276, 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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  /25

  $279,900

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  111 Genesee Trail, Winchester, VA 22602

  Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painted with new luxury vinyl planking throughout the entire house. Brand new bathroom with tub /shower. Open floor plan with bedrooms on each end of the house for privacy. 2 sheds that convey to store whatever your heart desires. Front deck to be stained as soon as weather permits. Shawnee Land is in a sanitary

  Jacquelyn Rizzari MarketPlace REALTY

  111 Genesee 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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  /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
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  /98

  $679,900

  • 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
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  /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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  /7

  $1,100,000

  • Land
  • 2.3 Acres
  • $478,261 per Acre

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

  2.3 Acre Outparcel on Pleasant Valley Road for Sale Neighbors include Walmart, Ross, Target, Panera Bread, Olive Garden, Petco, and the list goes on! Zoned CM1, ideal for auto sales, offices, retail, and flex development. All utilities to site. Outstanding proximity to massive commercial and multifamily growth. VA's fastest growing City in it's fastest growing commercial district. Almost 500'

  Gillian Greenfield Coldwell Banker Premier

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601
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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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  /40

  $699,900

  • 4 Beds
  • 3.5 Baths
  • 2,110 Sq Ft

  188 Marquis Ct, Winchester, VA 22603

  This spacious 4 bedroom ranch style home situated on 8.72 acres has a GREAT location convenient to schools, parks, shopping , major highways and at a GREAT price consisting of 1,910 sq. ft. of living space on the main level, offering a full partially finished basement with a full bath, window(s) and a french door leading to the rear yard. The home offers loads of storage, handicapped access on

  Sue Carpenter Long & Foster Real Estate, Inc.

  188 Marquis Ct, 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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  /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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  /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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  /140

  $329,000

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

  129 Jalapa Trail, Winchester, VA 22602

  Beautiful Mountain Views, from the left you see Maryland Mountains and the right you see the Sky Meadow Mountain in Paris Virginia Buyer Credit - This beautifully traditional home in Winchester, it 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

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
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  /2

  $514,900 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 3,152 Sq Ft

  407 Tamarack Cir, Winchester, VA 22602

  Beautiful colonial located on a quiet cul-de-sac. The formal living and dining rooms feature hardwood floors, crown molding, and chair rail. The light-filled, spacious kitchen offers an island and an eat-in area, perfect for everyday living and entertaining. A half bath completes the main level.Upstairs, enjoy a relaxing primary suite with a walk-in closet and attached bath with dual sinks,

  Heloisa Amar Samson Properties

  407 Tamarack Cir, Winchester, VA 22602
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  /21

  $780,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 3,476 Sq Ft

  230 Tranquil Wood Ln, Winchester, VA 22602

  NO HOA! UNDER CONSTRUCTION! Are you in search of a spacious, one-level living home that combines privacy and the freedom of no HOA restrictions? Your search ends here—introducing 230 Tranquil Wood Ln, Winchester, VA 22602, showcasing the exquisite Dogwood Model! Inspired by the tree it draws its name from, this charming residence is a true masterpiece, reflecting the superior craftsmanship of the

  Monique Rodriguez Pearson Smith Realty LLC

  230 Tranquil Wood Ln, Winchester, VA 22602
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  /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
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  /16

  $2,124,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,801 Sq Ft

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

  This is a rare opportunity to build a fully custom home tailored to your vision, crafted by Winchester’s award-winning builder, Hepler Homes. The home shown is a representative example of what can be built on this exceptional property. List price reflects the included options outlined in the documents section and is subject to change based on custom selections.The featured model offers a

  Nadeem Helfer Corcoran McEnearney

  152.44 Acres Lot 2 Laurel Grove 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
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  /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
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  /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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  /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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  /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
• 

  

  /64

  $415,000

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  4403 Back Mountain Rd, Winchester, VA 22602

  New Price! Nestled on two private wooded acres. New Roof 2023 - A peaceful country retreat with no HOA or restrictions. Colonial-style home features approximately 2,012 square feet of comfortable finished living space plus an unfinished basement. Includes 3 bedrooms and 2.5 baths. The walk-out basement provides excellent storage and potential for future expansion. The main level includes a

  RoxAnn Grimes RE/MAX Roots

  4403 Back Mountain Rd, Winchester, VA 22602
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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
• 

  

  /35

  $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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