Winchester, VA Homes for Sale

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  /67

  $399,999

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

  707 E Cork St, Winchester, VA 22601

  Don't let this location fool you - Plenty of parking on the side and back of the home and a large turn around space to exit onto Cork St easily! Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access to Jim Barnett Park just down the street, downtown walking mall and commuter roads, and even views

  Misty Weaver Samson Properties

  707 E Cork St, Winchester, VA 22601
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  /36

  $410,000

  • 4 Beds
  • 3.5 Baths
  • 2,261 Sq Ft

  125 Cheshire Ct, Winchester, VA 22602

  Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-sac on the east side of Winchester. Conveniently located to Rt 7 and I-81 and historic downtown Winchester. The 3-level townhouse backs to a wooded tree area and has a fenced rear yard. New luxury vinyl floor installed in majority of the home. As you enter, you will be welcomed into a large foyer with

  Eric Kronenwetter RE/MAX Roots

  125 Cheshire Ct, Winchester, VA 22602
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  /64

  $583,300

  • Studio
  • 2,600 Sq Ft

  10-12 W Cecil St, Winchester, VA 22601

  Income-Producing Duplex in Prime Winchester Location – Unique Investment Opportunity!Just two blocks south of Old Town Winchester’s Walking Mall, this charming duplex sits on a quiet residential street—offering the best of both location and lifestyle. With a strong rental history and over $54,000 in rental income in 2024, this property delivers a solid 6% cap rate, making it an ideal

  Alex Hodges Cottage Street Realty LLC

  10-12 W Cecil St, Winchester, VA 22601
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  /32

  $379,000

  • 2 Beds
  • 2 Baths
  • 1,384 Sq Ft

  221 Crestwood Ln, Winchester, VA 22602

  PRICE REDUCED OVER $10,000!!! Charming well maintained corner lot unit in desirable Woodbrook Village 55 and over community. 2 bedroom, 2 bath home with spacious living/dining room...almost 1400 square feet. Nice sized kitchen with newer appliances, breakfast area and adjoining utility room/office nook and laundry. One car garage with plenty of storage space. Large covered front AND back

  Stuart Wolk ERA Oakcrest Realty, Inc.

  221 Crestwood Ln, Winchester, VA 22602
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  /40

  $299,900

  • 2 Beds
  • 1 Bath
  • 863 Sq Ft

  1666 Apple Pie Ridge Rd, Winchester, VA 22603

  "A Slice Of Apple Pie" This 2-bedroom, 1 full bath ranch style home is ready for it's next owner! With modern updates the open style floorplan is perfect for everyday living. Beautiful kitchen with new quartz countertops, new cabinets and stainless-steel appliances. Updated bathroom with a new toilet, new vanity and tile surrounding the new tub/shower. Loft area with new carpet! Home has been

  Matt Kilmer Samson Properties

  1666 Apple Pie Ridge Rd, Winchester, VA 22603
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  /75

  $749,900

  • 4 Beds
  • 4 Baths
  • 3,783 Sq Ft

  137 Stonebrook Rd, Winchester, VA 22602

  Perched on an elevated lot, this handsome Colonial provides panoramic views from the spacious wrap-around porch and privacy for the fully-fenced back yard with composite deck. Lower level with front entrance includes office with full bath and large rec room. Main level has bedroom with full bath complemented by Primary with ensuite bath and two additional bedrooms and full bath on upper level,

  Dallas Croft Samson Properties

  137 Stonebrook Rd, Winchester, VA 22602
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  /46

  $399,900 Open Sat 2PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,450 Sq Ft

  461 Imperial St, Winchester, VA 22601

  Charming Rancher In Winchester, VA!Beautifully updated 4-bedroom, 2 full bath home offers both comfort and functionality. Fully finished basement ALSO includes a spacious 12x28 workshop with walk-out level to fenced rear yard—yard extends beyond the fence line! NEW gas furnace and NEW gas water heater just installed for new homeowner. Gorgeous hardwood floors throughout main level, newer

  Kara Burnett Samson Properties

  461 Imperial St, Winchester, VA 22601
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  /38

  $77,699

  • Land
  • 6.09 Acres
  • $12,758 per Acre

  440 Iris Ln, Winchester, VA 22602

  Enjoy breathtaking, unrivaled views of the Shenandoah Valley below from this ridgetop property on Little North Mountain.-Gorgeous Sunset Valley Views-Two Lots in One – Build on Both or Split Off!-Extensive Road Frontage-Power along Road-Very Buildable, No Floodplain or Wetlands-“Goldilocks” Location – countryside serenity, yet just 15 mins from downtown

  Ralph Harvey ListWithFreedom.com

  440 Iris Ln, Winchester, VA 22602
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  /50

  $569,000

  • 4 Beds
  • 4.5 Baths
  • 3,076 Sq Ft

  107 Okeefe Dr, Winchester, VA 22602

  Carpeting has been replaced with rich hardwood flooring on main level. 2020 New HVAC & Roof & Hot Water Heater & Foyer Pladian Window. This amazing home features a newly renovated kitchen (2023) that you will fall in love with. Talk about gourmet, It's a chef's dream come true featuring a gas cooking range, Silestone counters, a coffee bar, (featuring a butcher block), a huge island, built

  Cynthia Butler Samson Properties

  107 Okeefe Dr, Winchester, VA 22602
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  /9

  $29,900

  • Land
  • 1.28 Acres
  • $23,359 per Acre

  Lot 15, 16, 17, 18 Gatling Dr, Winchester, VA 22602

  Talk about location! Situated in beautiful Mountain Falls (Wild Acres) enjoy scenic mountain views coming going. It's beautiful & peaceful. Enjoy the amenities of the community. Short distance to Rt 50, shopping, hospital & downtown Winchester or short drive to Stephens City. 4 Lots Total of 1.28 acres beginning at the corner of Quail fronts on Gatling & wraps at corner of Bluebird with a gentle

  Gina Griffith MarketPlace REALTY

  Lot 15, 16, 17, 18 Gatling Dr, Winchester, VA 22602
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  /29

  $289,900

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East

  Jodi Costello ERA Oakcrest Realty, Inc.

  1125 Conway St, Winchester, VA 22601
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  /20

  $334,000

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  MOTIVATED SELLER - OFFERING SUBSIDY TO BUYER FOR CLOSING COSTS OR MORTGAGE RATE BUY DOWN One Way street = quiet Gorgeous Rehab - you have to see it! Secure Parking off the alley Efficient HVAC mini splits installed Washer and Dryer included

  Teri Domanski Corcoran McEnearney

  553 Highland Ave, Winchester, VA 22601
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  /29

  $599,900

  • 5 Beds
  • 3 Baths
  • 4,047 Sq Ft

  103 Sharon Dr, Winchester, VA 22602

  Classic Brick Cape Cod in Stonebrook Farms offering over 4,000 sq. ft. of finished living space on a beautifully landscaped 3⁄4-acre lot. This home blends timeless character with a spacious, traditional layout.Step inside to find a formal living room and dining room that flow seamlessly into the kitchen and family room—perfect for gathering and entertaining. The main level also features a

  Leah Marabella Realty ONE Group Old Towne

  103 Sharon Dr, Winchester, VA 22602
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  /20

  $289,999

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  608 Green St, Winchester, VA 22601

  Welcome to 608 Green Street. Come make this your own space. 3-Bedroom, 1 full bath. Hardwood floors, no carpet! Attached carport. Brand new shed in the backyard. Backs to common area. Deck off the back of the home. Newer windows. New Roof. Large kitchen. Laundry room off the kitchen. This home is within the city limits of Winchester City School System. Within walking distance to school and

  Linda DeFelice Samson Properties

  608 Green St, Winchester, VA 22601
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  /55

  $699,999

  • 4 Beds
  • 4.5 Baths
  • 5,183 Sq Ft

  1877 Clayton Ridge Dr, Winchester, VA 22601

  From the moment you arrive, this home welcomes you in. A spacious covered front porch—perfect for rocking chairs and quiet mornings—sets the stage for the warmth and comfort that await inside. Step through the front door into an open foyer, where a formal living room sits to the left and a stately office with French doors lies to the right. At the heart of the home, the kitchen features granite

  Leah Marabella Realty ONE Group Old Towne

  1877 Clayton Ridge Dr, Winchester, VA 22601
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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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  /55

  $685,000

  • 5 Beds
  • 4 Baths
  • 4,576 Sq Ft

  800 Lake Dr, Winchester, VA 22601

  Location Location Location! Welcome to 800 Lake Dr. Winchester VA 22601, Located in the highly sought-after Rolling Hills community and situated on a 0.37 acre lot, This expansive home offers 4,500+ sqft. of living space, featuring 5 bedrooms, 4 Full baths, finished basement, and 2 car garage! Step inside to find gleaming hardwood floors in the formal living and dining rooms. The unique

  Lisa Behr Coldwell Banker Premier

  800 Lake Dr, Winchester, VA 22601
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  /45

  $575,000

  • 5 Beds
  • 3.5 Baths
  • 4,235 Sq Ft

  428 Westside Station Dr, Winchester, VA 22601

  Buyer credit $10,000 at settlement with ratified contract by Nov 3, 2025, Beautiful, stately 5 BR 3.5 BA, 4000sq ft, colonial situated on a quiet cul de sac in a community located across from Winchester Medical Center, close to Old Town Winchester and convenient commuter routes! Who could ask for more! From the very first look, you're greeted by the lovely front porch, elegant columns, new

  Donna Raczynski Long & Foster Real Estate, Inc.

  428 Westside Station Dr, Winchester, VA 22601
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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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  /39

  $650,000

  • 4 Beds
  • 4.5 Baths
  • 4,658 Sq Ft

  104 Heath Ct, Winchester, VA 22602

  This is the home you've been looking for! A lovely Colonial with room to spread out. A beautiful open floor plan with both elegance and comfort. Gorgeous hardwood floors on most of the main floor. Formal living and dining rooms, large gourmet kitchen with granite countertops, stainless steel appliances, stunning backsplash and an eating area. Also a main level den for added space and a cozy

  Kathryn Symenow CENTURY 21 New Millennium

  104 Heath Ct, Winchester, VA 22602
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  /74

  $699,000

  • 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 home offering 4,100+ 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 entertaining and

  RoxAnn Grimes RE/MAX Roots

  140 Plow Run Ln, Winchester, VA 22602
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  /45

  $340,000

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft

  191 Chapman Ln, Winchester, VA 22603

  Cute as a button Cape Cod on over 2 acres and don't miss the contemporary (pretty cool) converted run in shed which can have multiple uses. Refinished hardwood floors, plenty of quaint spaces, massive decking, central ac, country kitchen with butcher block island, and move in ready. Land/lot is unrestricted.

  Dave Spence RE/MAX Roots

  191 Chapman Ln, Winchester, VA 22603
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  /60

  $1,999,999

  • 5 Beds
  • 6 Baths
  • 5,590 Sq Ft

  821 Apple Pie Ridge Rd, Winchester, VA 22603

  This extraordinary 5-bedroom, 6-bathroom estate sits on 14.44 acres across two parcels—5.0 acres on the front lot and 9.44 acres with the residence—just minutes from Winchester, Virginia. Designed for both everyday living and elegant entertaining, this home combines timeless style with modern luxury. Inside, hardwood floors and soaring ceilings enhance open, light-filled spaces. The recently

  Jason Saphire HomeZu.com of Virginia

  821 Apple Pie Ridge Rd, Winchester, VA 22603
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  /41

  $355,000

  • 4 Beds
  • 2.5 Baths
  • 2,804 Sq Ft

  513 van Fossen St, Winchester, VA 22601

  Welcome to 513 Van Fossen St, a beautifully updated 4-bedroom, 2.5-bathroom brick ranch conveniently located just minutes from downtown Winchester. Step inside to discover freshly refinished original red oak hardwood floors (locally sourced from Plumly Lumber) in a warm Golden Pecan finish (2025). The home boasts fresh paint inside and out, a brand-new roof (2025), and newer HVAC. The living room

  Amy Longerbeam RE/MAX Roots

  513 van Fossen St, Winchester, VA 22601
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  /42

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft

  715 Berryville Ave, Winchester, VA 22601

  This renovated jewel on the east side of Winchester is ready for you! Enjoy the new modern kitchen, new tile bathrooms, updated HVAC and electrical, fresh paint, refinished floors, and more! Plus, this home is full of character you don't find in new homes. Look close! From unique windows to original molding and solid interior doors, you'll find unexpected charm everywhere. Between the unfinished

  William Steinmetz RE/MAX Roots

  715 Berryville Ave, Winchester, VA 22601
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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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  /58

  $370,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  133 Erie Trail, Winchester, VA 22602

  Motivated Seller! Discover this charming ranch-style home nestled in the desirable Shawneeland community, offering a perfect blend of comfort and outdoor enjoyment. This well-maintained 3-bedroom, 2-bathroom residence spans 1,456 sq ft and features a thoughtful layout with an entry-level bedroom, ideal for convenience. Step inside to find a welcoming combination kitchen/living area, complemented

  Tracy Link Coldwell Banker Premier

  133 Erie Trail, Winchester, VA 22602
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  /42

  $459,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft

  1332 Ramseur Ln, Winchester, VA 22601

  Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exterior condo offering 3 bedrooms and 2 full baths. Rich hardwood floors flow throughout the home. The primary bedroom includes a cozy fireplace perfect for relaxing evenings. Updated appliances, such as washer, dryer, refrigerator, stove and microwave. Enjoy the ease of your own private elevator within the

  James King RE/MAX Roots

  1332 Ramseur Ln, Winchester, VA 22601
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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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  /43

  $415,000

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft

  128 Pioneers Rd, Winchester, VA 22602

  Previous buyers financing fell through! Back on Market! This one went under contract right away. Second Chance can be your blessing! Charming Colonial-Cape Cod Home in Prime Winchester Location Close To Old Town. Welcome home to comfort, style, and convenience all wrapped into one! This beautifully upgraded 4-bedroom, 2-bathroom colonial-cape cod residence is ideally situated just minutes from

  Kevin Richards Keller Williams Realty

  128 Pioneers Rd, Winchester, VA 22602
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  /60

  $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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  /60

  $425,000

  • 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 Rt 50, Rt 37 and I 81— and less than 20 minutes to Winchester Medical Center! 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

  Kira Grubb Realty ONE Group Old Towne

  3634 Wardensville Grade, 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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  /14

  $448,700

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  421 Superior Ave, Winchester, VA 22601

  Renovated and move in ready! Let's start with the new mailbox, new 16' wide asphalt driveway, new 8'x13' concrete patio for you to enjoy watching the sun sets overlooking the large back yard., The carport even has bolts in ceiling for you to install a swing. Then inside, new heat pump and central a/c system, new appliances with fingerprint resistant stainless-steel exterior, stainless steel liner

  Leo Smith CENTURY 21 New Millennium

  421 Superior Ave, Winchester, VA 22601
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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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  /21

  $99,900

  • Land
  • 0.65 Acre
  • $153,692 per Acre

  222 Siler Ln, Winchester, VA 22603

  UPDATE--NEW PRICE. Seller says SELL...UNRESTRICTED LAND and a BRAND NEW WELL installed by SHIRLEY WELL DRILLING - 11 GPM. SELLING AT ASSESSED VALUE for 2025 ($83,000.00) plus cost of well ($ 16,900) Engineering report complete for drain field and all conveys $1,450.00 value- conveys. New Survey done -$800,00 Value-The lot has been leveled for a beautiful home site (cost $ 16,000.,00).

  Erick Erdal Long & Foster Real Estate, Inc.

  222 Siler Ln, 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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  /17

  $435,000

  • 5 Beds
  • 4 Baths
  • 2,014 Sq Ft

  122 Cherry Hill Cir, Winchester, VA 22602

  Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

  Jen Moore ERA Oakcrest Realty, Inc.

  122 Cherry Hill Cir, Winchester, VA 22602
• 

  

  /65

  $799,900

  • 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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