Winchester, VA Homes for Sale with Acreage

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  /46

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,859 Sq Ft

  247 Mcguire Rd, Winchester, VA 22603

  Tucked away on a private 2.7-acre wooded lot, this stunning all-brick colonial was fully renovated from top to bottom last year. Inside, 3/4" solid ash, 5"wide herringbone flooring flows throughout, accented by designer lighting, crown molding, and elegant chair rail trim. The chef’s kitchen is a true showstopper—featuring a massive island, striking white and gold appliances, and custom finishes.

  

  Lori Bales

  Keller Williams Realty

  (540) 701-5541

  247 Mcguire Rd, Winchester, VA 22603
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  Explore Winchester

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  /12

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  2718 Welltown Rd, Winchester, VA 22603

  Beautiful and buildable lots on Welltown Road. Build your dream house and an extended family suite/ guest house. Build two, live in one, sell one! There are so many option on this unrestricted parcel. The mobile home on the property has electric, well and septic. The mobile home is not where the value is and is a tear down. The second parcel has been perc previously and is suitable for

  

  Tracey Scott

  Path Realty

  (540) 453-8745

  2718 Welltown Rd, Winchester, VA 22603
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  /9

  $225,000

  • Land
  • 5.99 Acres
  • $37,563 per Acre

  Lot 3 Cedar Creek Grade, Winchester, VA

  Beautiful lot in a small neighborhood on the very desirable west side of Winchester off Cedar Creek Grade! Lot is already perked for an alternative septic system. This opportunity doesn’t come along often! Rolling hills with beautiful surroundings and views. The location is less than 10 minutes to grocery stores, downtown Winchester, or Winchester Medical Center. It’s also located within 2

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 3 Cedar Creek Grade, Winchester, VA
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  /35

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  1420 Fishel Rd, Winchester, VA 22602

  Nestled away in the trees, this updated retreat on 2.67 acres offers the perfect blend of peace, privacy, and one-level living. Inside, you’ll find 3 bedrooms, 2 renovated baths, brand-new flooring, and fresh paint throughout. The bright eat-in kitchen with island and stainless appliances flows into a spacious sitting room, enclosed rear porch with A/C, and a covered front porch for year-round

  

  Katherine (Kat) Wetzel

  Century 21 Redwood Realty

  (540) 779-1383

  1420 Fishel Rd, Winchester, VA 22602
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  /35

  $819,950

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  601 Fall Run Ln, Winchester, VA 22602

  What better than a custom-built home on 20+ acres that can be subdivided if you so wish?$50k price drop! Prepare to be captivated by the beauty and tranquility of this exceptional custom-built home, nestled on 20.10 acres with breathtaking mountain views. Offering desirable one-level living, this nearly new (under 3 years old) home boasts a gorgeous covered porch and an expansive deck

  Theo Theologis Slones Real Estate

  601 Fall Run Ln, Winchester, VA 22602
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  /55

  $609,900 Open Sat 10AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,618 Sq Ft

  281 Light Rd, Winchester, VA 22603

  Price Improvement! Motivated Sellers! Bring your offers! Main Level Living! POOL! 5 GARAGE SPACES, POLE BARN & MORE! Appraised for $646,000! Ranch-Style Retreat on almost 8.5 Acres in Frederick County, VA, 20 mins. from Winchester! Calling all Homesteaders - your Farmette awaits! This property offers endless possibilities, any type of hobby, gardening, farmette, horses, workshop,

  Jennifer Watt Century 21 Redwood Realty

  281 Light Rd, Winchester, VA 22603
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  /23

  $168,000

  • Land
  • 10 Acres
  • $16,800 per Acre

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602

  Enjoy rural living and fun on this building lot in the Long Ridge Estates community. This prime building lot is located off of Gough Road in the High View Manor area of the county. This parcel has a septic certification letter on record with the county health department for a four-bedroom septic system. Access is secured via a 50 ft deeded access easement, which has already been installed and

  Chad Pangle Whitetail Properties Real Estate

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602
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  /56

  $760,000

  • 4 Beds
  • 2.5 Baths
  • 2,937 Sq Ft

  442 Frog Hollow Rd, Winchester, VA 22603

  Nestled in the serene Frog Hollow Estates, this charming Colonial home offers a perfect blend of comfort and functionality. With four spacious bedrooms and 2.5 bathrooms, the interior is designed for modern living. The traditional floor plan flows seamlessly into a family room off the kitchen, creating a warm atmosphere for entertaining. Step outside to discover 11 acres of picturesque land,

  Wendy Conner Coldwell Banker Premier

  442 Frog Hollow Rd, Winchester, VA 22603
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  /42

  $767,900

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

  1049 Laurel Grove Rd, Winchester, VA 22602

  Tucked away on a quiet cul-de-sac, 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

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
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  /65

  $825,000

  • 4 Beds
  • 3.5 Baths
  • 5,040 Sq Ft

  2411 Hunting Ridge Rd, Winchester, VA 22603

  This is the one you've been waiting for! Welcome to 2411 Hunting Ridge Rd. This large and private classic colonial is ready for you. With over 5000 sq ft and more than 5 acres of property, this beautiful home has it all. The winding tree-lined (and paved!) driveway invites you in. Enter into the welcoming two story foyer, which is flanked by lovely formal dining and sitting rooms. Exploring

  Amanda White Nova Home Hunters Realty

  2411 Hunting Ridge Rd, Winchester, VA 22603
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  /145

  $980,000

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

  150 Ewell Dr, Winchester, VA 22602

  Welcome to Equestrian Estates, a sought-after Winchester community with no HOA, where this stately 5 bedroom, 6 bath colonial offers over 6,700 square feet of finished living space on nearly 3 acres. Originally built in 2007 and extensively updated in 2020, the home showcases high-end finishes throughout, including fully renovated bathrooms with luxury details such as smart toilets, heated floors

  Reed Jimenez Hunt Country Sotheby's International Realty

  150 Ewell Dr, Winchester, VA 22602
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  /39

  $725,000

  • 4 Beds
  • 2 Baths
  • 1,946 Sq Ft

  289 Westview Dr, Winchester, VA 22603

  Coming soon because owner is finishing a few things to make this a full show stopper. Over 13 acres nestled at the end of Westview Dr. So quiet, peace and serenity. Blacktop parking area to accomidate 4 cars in front of home and plenty of driveway parking, plus a 2 car garage close by with work area in the back with long bench table. Really nice knotty pine floors on first floor, carpet on

  Harry Hamilton CENTURY 21 New Millennium

  289 Westview Dr, Winchester, VA 22603
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  /58

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,348 Sq Ft

  280 Plow Run Ln, Winchester, VA 22602

  Now available: a custom-built, one-level home situated on 3.02 peaceful acres. This property boasts a highly convenient country location, less than nine miles from Winchester Medical Center. Constructed in 2017, this elegant home offers a functional floor plan with a contemporary flair. Entryway leads into an open living area featuring nine-foot ceilings and gorgeous hardwood floors,

  Angela Duncan MarketPlace REALTY

  280 Plow Run Ln, Winchester, VA 22602
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  /51

  $935,000

  • 3 Beds
  • 2.5 Baths
  • 2,624 Sq Ft

  3328 Millwood Pike, Winchester, VA 22602

  Nestled on an expansive 20.54-acre lot, this stunning ranch-style home, built in 2023, offers a harmonious blend of luxury and comfort. The exterior showcases a sophisticated combination of HardiPlank, masonry, and stone, creating a timeless appeal that invites you to explore the beauty within. Step inside to discover an open floor plan that seamlessly connects the living, dining, and kitchen

  Erika De Azagra ERA Oakcrest Realty, Inc.

  3328 Millwood Pike, Winchester, VA 22602
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  /93

  $898,000

  • 4 Beds
  • 3.5 Baths
  • 3,532 Sq Ft

  430 Saddleback Ln, Winchester, VA 22602

  Welcome to 430 Saddleback Lane in Sheridan's Miss. Located minutes to downtown Winchester, VA. This 8.51 acre lot features lush landscaping and mature trees, with just the right amount of open space. The in ground salt water pool is the perfect spot for these hot summer days! This home has been well maintained and it shows. Enjoy morning coffee on your covered wrap around deck on the

  Jim Stafford ERA Oakcrest Realty, Inc.

  430 Saddleback Ln, Winchester, VA 22602
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  /58

  $699,999

  • 5 Beds
  • 3.5 Baths
  • 4,144 Sq Ft

  108 Katie Ln, Winchester, VA 22602

  Welcome to 108 Katie Lane in beautiful Stonebrook Farms. This classic brick home has space, charm, and a setting that feels like home the moment you pull up. With five large bedrooms, including a comfortable primary suite, there is room for everyone.The main level features an open floor plan with hardwood floors throughout, creating a warm and welcoming feel. A gas fireplace adds a cozy

  Sharon Farinholt Realty ONE Group Old Towne

  108 Katie Ln, Winchester, VA 22602
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  /40

  $899,000

  • 5 Beds
  • 6.5 Baths
  • 4,301 Sq Ft

  254 Whistlewood Ln, Winchester, VA 22602

  Situated in the picturesque countryside of Winchester Virginia boasting a modern aesthetic and elevation. Welcome home to 254 Whistlewood Ln! The home is beautifully positioned within the Royal Oaks community on a private 5 acre lot! It benefits from the serenity one would expect from a countryside home and the convenience of a short distance to town, commuter routes and just 15 minutes to

  Stuart Pollard Pearson Smith Realty, LLC

  254 Whistlewood Ln, Winchester, VA 22602
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  /72

  $695,000

  • 5 Beds
  • 4 Baths
  • 4,387 Sq Ft

  3949 N Frederick Pike, Winchester, VA 22603

  You will feel the peace and harmony the moment you come up the drive, this is your new home place. Almost 4 unrestricted acres for you to spread your wings. The sweet spots here will truly tug at your heart, the hammock area for lazy day reading, the fire pit with the most incredible mountain views in the fall and winter months, The four wheeler trails begging for fun and memories!! The

  Kristen Kerns Roberts Realty Group, LLC

  3949 N Frederick Pike, Winchester, VA 22603
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  /42

  $769,900

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

  1049 Laurel Grove Rd, Winchester, VA 22602

  Nestled at the end of a peaceful cul-de-sac, this stunning, property offers the perfect blend of seclusion and community living. This custom-designed home offers three bedrooms and three bathrooms, with the convenience of main-level living. Surrounded by lush woodlands and boasting breathtaking views of both trees and mountains, this property is ideal for those seeking a tranquil retreat that

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
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  /77

  $765,000

  • 4 Beds
  • 3.5 Baths
  • 3,504 Sq Ft

  3980 Middle Rd, Winchester, VA 22602

  Custom, all-brick white rambler with a French Country ambience, enjoys boundaries of a lovely brook and a berm of boulders and indigenous plantings that obscures property from the roadway. All rooms are generously sized with the main level suitable for one-level living with Primary bedroom and laundry. Bedrooms on upper level are large enough for additional sitting area or study furnishings.

  Dallas Croft Samson Properties

  3980 Middle Rd, Winchester, VA 22602
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  /48

  $799,900 New Construction

  • 5 Beds
  • 3 Baths
  • 3,056 Sq Ft

  181 Oak Dr, Winchester, VA 22603

  Very private community all paved road. Close to town with wooded lots 10 minutes to town. Make your selections. This home boosts two level living with 3,056 sq. ft. of floor plan with so many features others would call them upgrades! Brick front with cement siding on three sides. Large concrete front porch with concrete lead walk. No HOA. Builders upgrades: hardwood entire house (except baths

  Jim Thomson Realty ONE Group Old Towne

  181 Oak Dr, Winchester, VA 22603
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  /2

  $724,900 Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 4,113 Sq Ft

  140 Plow Run Ln, Winchester, VA 22602

  Craftsman-Style Home on 3.45 Private Acres – 140 Plow Run Ln, Winchester, VAWelcome to this beautiful craftsman-style home offering 4,423 finished sq ft of thoughtfully designed living space on 3.45 private acres. The main level features an open floor plan with a spacious kitchen, living room, and cozy fireplace, a dedicated office, formal dining room, and a large kitchen—perfect for

  RoxAnn Grimes RE/MAX Roots

  140 Plow Run Ln, 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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  /71

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft

  1576 Old Bethel Church Rd, Winchester, VA 22603

  Step back in time with this 1931 farmhouse set on 5 acres, blending historic character with thoughtful modern updates—all just minutes from Winchester. This property offers convenient access to main roads while maintaining the space and feel of country living.The home features 3 bedrooms, 2 updated baths, hardwood floors, and an oversized two-car garage with workshop space. Recent

  Natasha Roberts Realty ONE Group Old Towne

  1576 Old Bethel Church Rd, Winchester, VA 22603
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  /55

  $499,000

  • 3 Beds
  • 1 Bath
  • 2,050 Sq Ft

  3634 Wardensville Grade, Winchester, VA 22602

  Country charm meets convenience at 3634 Wardensville Grade—just minutes to Old Town Winchester, Rt 50, Rt 37 and I 81—set on just under 9 acres with 2,572 sq ft, 3 bedrooms, and 1 bath. This light-filled home offers an easy-flow layout with generous gathering spaces, a bright kitchen, and flexible rooms ideal for a home office or hobby area. Cozy warmth comes from two woodstoves and a pellet

  Kira Grubb Realty ONE Group Old Towne

  3634 Wardensville Grade, Winchester, VA 22602
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  /38

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,947 Sq Ft

  266 Pond View Ln, Winchester, VA 22603

  Discover peace and privacy at 266 Pond View Lane. Nestled on 5 scenic acres, this property offers the perfect retreat from the hustle and bustle— A wrap-around gravel driveway welcomes you home, providing plenty of space for parking and easy access to the attached garage! Step inside to find 3 spacious bedrooms, 1 full bathroom, formal dining & 3 spacious living areas! The kitchen offers

  Lisa Behr Coldwell Banker Premier

  266 Pond View Ln, 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 RE/MAX Roots

  Lot C Cather Ln, Winchester, VA 22602
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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 RE/MAX Roots

  Lot B Cather Ln, 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 RE/MAX Roots

  Lot A Cather Ln, Winchester, VA 22602
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  /59

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 3,296 Sq Ft

  478 Brookneil Dr, Winchester, VA 22602

  Welcome to 478 Brookneil Drive, a solidly built 4-bedroom, 3.5-bath home nestled on 5.16 acres in sought after Brookneil Subdivision. This property blends the best of rural living with the convenience of being just minutes from town, major commuter routes, schools, shopping, 7 minutes to Winchester Medical Center and all that Winchester has to offer.The home itself offers a timeless floor

  Katrina Smith RE/MAX Roots

  478 Brookneil Dr, Winchester, VA 22602
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  /92

  $1,175,000

  • 4 Beds
  • 3.5 Baths
  • 4,815 Sq Ft

  2321 Cedar Grove Rd, Winchester, VA 22603

  Escape to your own private retreat! This custom log home on 21 wooded acres offers space, comfort, and endless outdoor enjoyment—without the restrictions of an HOA. Featuring over 3,200 sq. ft. on the main level plus 1,600+ finished sq. ft. in the walkout basement, this home provides room for everyone.Inside, you’ll find 4 bedrooms, 3 1/2 baths, and 2 fireplaces, along with an outdoor

  Traci Shoberg RE/MAX Roots

  2321 Cedar Grove Rd, Winchester, VA 22603
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  /68

  $509,900

  • 4 Beds
  • 2.5 Baths
  • 2,414 Sq Ft

  438 Mountain Falls Blvd, Winchester, VA 22602

  A RARE Find in Wilde Acres for such a MAGNIFICENT Property! So Majestic with Incredible Curb Appeal! You will be SO Taken by the Beauty of this Very Well Maintained Home/LOT (1 AC) & Additional Lots (.25 AC EA) 2 additional LOTS (separate tax records: TAX ID: 58-A02-R-5-5 AND TAX ID: 58-A02-R-5-24). All together 1.5 ACRES! Sit on the new trex deck to view the small creek with a

  Jodi Costello ERA Oakcrest Realty, Inc.

  438 Mountain Falls Blvd, Winchester, VA 22602
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  /65

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 3,283 Sq Ft

  231 Gun Barrel Ln, Winchester, VA 22603

  Spectacular, move-in ready rancher on over 6 acres. Completely remodeled within the past 3 years with all appliances, HVAC systems, roof, flooring and more less than 3 years old. The home offers a beautiful new kitchen with upgraded cabinets and quartz countertops. All bathrooms have also been completely updated with top-of-the-line vanities, tile and flooring. The lower level is finished into

  Dennis Virts RE/MAX Distinctive Real Estate, Inc.

  231 Gun Barrel Ln, Winchester, VA 22603
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  /12

  $275,000

  • Land
  • 78.79 Acres
  • $3,490 per Acre

  LOT 13 Great Mountain Ln, Winchester, VA 22602

  Located In The Great North Mountain Wilderness Community! Don't Miss Out On This Amazing Opportunity To Own 78 Acres With Scenic Views! Whether You Are Looking For A Place To Build Your Dream Home Or A Get Away To Camp and Hunt With The Family, This Is The Perfect Location! As You Drive Up The Gravel Driveway There Is A Cleared Flat Area That Currently Has A Camper, Bunker, Out House, Solar

  Joseph Dedekind LPT Realty, LLC

  LOT 13 Great Mountain Ln, Winchester, VA 22602
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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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  /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 RE/MAX Roots

  2725 S Pleasant Valley Rd, Winchester, VA 22601
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  /44

  $359,000

  • 2 Beds
  • 1 Bath
  • 1,348 Sq Ft

  242 Footstone Ln, Winchester, VA 22603

  Peaceful Country Retreat on 4.7 Acres – Minutes from WinchesterDiscover the perfect blend of comfort, charm, and privacy in this unique country home, ideally situated just minutes from Winchester. Nestled on a quiet gravel lane with a road maintenance agreement in place, this beautifully maintained property features a timeless stone and brick exterior and rich hardwood floors throughout.

  Kristina Towns Weichert Realtors - Blue Ribbon

  242 Footstone Ln, Winchester, VA 22603
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  /47

  $325,000

  • Land
  • 15 Acres
  • $21,667 per Acre

  000 Light Rd, Winchester, VA 22603

  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

  Melissa Johnston ERA Oakcrest Realty, Inc.

  000 Light Rd, Winchester, VA 22603
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  /129

  $1,170,000

  • 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
• 

  

  /6

  $99,990

  • Land
  • 6.13 Acres
  • $16,312 per Acre

  0 Gun Barrel Ln Unit VAFV2036134, Winchester, VA 22603

  Nice building lot in a great location just a few minutes west of Winchester. This is an all wooded lot that offers privacy and seclusion with no restrictive covenants. There is a road maintenance agreement in place for this subdivision which keeps the access easement in good condition. The property was approved for a 4 bedroom drainfield via a certification letter from the health department.

  Dennis Virts RE/MAX Distinctive Real Estate, Inc.

  0 Gun Barrel Ln Unit VAFV2036134, Winchester, VA 22603

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