Winchester, VA Homes for Sale

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  $6,500

  • Land
  • 11,325 Sq Ft
  • $25,000 per Acre

  0 Fox Trail Unit VAFV2040348, Winchester, VA 22602

  Vacant lot on Fox Trail in Wilde Acres! This is raw land, no perc test has been done. Affordable and at the top, for lots of views of North Mountain. Private - not many homes around this lot. Sign on Property

  Traci Shoberg Samson Properties

  0 Fox Trail Unit VAFV2040348, Winchester, VA 22602
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  $525,000

  • 3 Beds
  • 1 Bath
  • 1,370 Sq Ft

  1310 Siler Rd, Winchester, VA 22603

  Come and see this serene, wooded, hilltop retreat, just minutes west of Winchester. This fully updated 3 BR, 1 BA Brick Rambler is situated on a private, unrestricted 10-acre wooded lot with great views. This home has a covered front porch and an 18-by-30-foot concrete patio in the back, perfect for entertaining. The brick Fireplace has a wood-burning stove insert. This home has been fully

  Marcia Coss Weichert, REALTORS

  1310 Siler Rd, Winchester, VA 22603
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  /46

  $1,150,000

  • 5 Beds
  • 5 Baths
  • 5,695 Sq Ft

  801 Armistead St, Winchester, VA 22601

  There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been working so hard to create. Nestled in one of Winchester's most beloved neighborhoods, this stately residence blends timeless elegance with the confidence that comes from knowing the important work has already been done. Over the past

  Donna Chong Samson Properties

  801 Armistead St, Winchester, VA 22601
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  /19

  $165,000

  • 2 Beds
  • 1 Bath
  • 652 Sq Ft

  616 Opossum Trail, Winchester, VA 22602

  Escape to the peace and privacy of Wilde Acres with this charming 2-bedroom, 1-bath cabin situated on four lots for a total of 1 acre, offering extra space and the possibility of potential expansion. This property is being sold As-Is and is in need of some cosmetic work. It presents a great opportunity for a weekend retreat, investment property, or full-time residence with a little TLC. Recent

  Dona Shiley ERA Oakcrest Realty, Inc.

  616 Opossum Trail, Winchester, VA 22602
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  /17

  $619,000

  $6K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 2,967 Sq Ft

  219 Lehigh Dr, Winchester, VA 22602

  This nearly new Lennar home offers the advantages of modern construction combined with thoughtful upgrades and future expansion potential in a location that keeps you connected to everything Winchester has to offer. Built just two years ago, the home provides the confidence of newer systems and energy efficiency, enhanced by a complete security system and water softener for added comfort and

  Sarah Reynolds Keller Williams Realty

  219 Lehigh Dr, Winchester, VA 22602
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  /43

  $425,000

  • 4 Beds
  • 3 Baths
  • 2,157 Sq Ft

  1709 Brandon Dr, Winchester, VA 22601

  Spacious Home in a Prime Location! Discover the potential of this well-built Cape Cod offering generous living spaces and timeless charm. The welcoming living and dining area features a cozy fireplace, creating the perfect setting for gatherings and everyday living. The main level includes a desirable primary suite with a private full bath, an additional bedroom, and a hall bath for added

  Darcy Amburn Colony Realty

  1709 Brandon Dr, Winchester, VA 22601
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  $640,990

  New Construction $13K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,031 Sq Ft

  232 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Azalea floorplan is a thoughtfully designed 1,888 sq. ft. ranch home blending style and functionality in a single-level open layout. The moment you step inside the home, you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen,

  D.R. Horton Builder

  232 Hydrangea Way, Winchester, VA 22602
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  /52

  $559,000

  • 5 Beds
  • 3.5 Baths
  • 2,794 Sq Ft

  222 Cavalry Dr, Winchester, VA 22602

  Welcome to 222 Cavalry Drive — a beautifully maintained brick-front colonial offering timeless style, functional living, and exceptional versatility throughout. Situated on a 0.28-acre lot in the established Pioneer Heights community, this home features 5 Bedrooms, 3.5 baths 2 car garage and over 2,800 Sqft of living space. Step inside to gleaming hardwood floors across the main level, which

  Lisa Behr Hunt Country Sotheby's International Realty

  222 Cavalry Dr, Winchester, VA 22602
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  /6

  $40,000

  $10K PRICE DROP

  • 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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  /55

  $299,990

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft

  406 Highland Ave, Winchester, VA 22601

  HERE IS YOUR CHANCE! BACK ON THE MARKET DUE TO NO FAULT OF THE SELLERS!!DIRECTIONS FOR PARKING; FROM NAT AVE TAKE RIGHT ON ATHEY ALLY TO 4 CAR PARKING AREA ON LEFT - LOOK FOR 406 MARKER. Located in The Historic Old Town Winchester area with private parking right off of Athey Alley, we are happy to list this nicely remodeled 2 story circa 1930s, center hall home.. Since the purchase of this

  Lisette Turner Century 21 Redwood Realty

  406 Highland Ave, Winchester, VA 22601
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  $325,000

  Open Sun 11AM - 1PM $125K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,585 Sq Ft

  139 Bryarly Rd, Winchester, VA 22603

  Your chance at a beautiful home has arrived—bringing you instant equity on day one! Back on the market at no fault of the seller and priced well below its recent appraisal, this home is a rare financial win. With an out-of-state relocation already calling them away, the sellers are incredibly eager to pass the keys to the next owner and are offering $5,000 in closing cost assistance. From the

  Hailey Mooney Real Broker, LLC

  139 Bryarly Rd, Winchester, VA 22603
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  /2

  $409,900

  Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,228 Sq Ft

  117 Old Dominion Dr, Winchester, VA 22603

  Well-maintained split foyer in a spectacular commuter location, just minutes from I-81 and a short drive to Old Town Winchester. This inviting home features hardwood floors throughout the main living areas, an open-concept floor plan, a cozy fireplace in the living room, and a spacious kitchen with a center island.The main level offers new carpet in the bedrooms, including a generous primary

  Heloisa Amar Samson Properties

  117 Old Dominion Dr, Winchester, VA 22603
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  $459,990

  New Construction $8K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,461 Sq Ft

  125 Trellis View Ln, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa, blending style and functionality in a single-level open layout and finished loft, complete with a 2-car garage. This stunning 1,492 sq. ft. residence features three bedrooms and two baths on the main level, with the finished loft offering an additional 676 sq ft of

  D.R. Horton Builder

  125 Trellis View Ln, Winchester, VA 22602
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  /40

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,180 Sq Ft

  104 Lenore Ln, Winchester, VA 22602

  Like New -Welcome to this beautiful home in the desirable Raven Oaks. This thoughtfully designed home features an open-concept floor plan perfect for both everyday living and entertaining. The spacious kitchen offers a large island, ample cabinetry, and flows seamlessly into the dining area and Great Room with a cozy fireplace, creating a warm and inviting gathering space. Upstairs, a versatile

  RoxAnn Grimes RE/MAX Roots

  104 Lenore Ln, Winchester, VA 22602
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  /25

  $397,990

  New Construction

  • 3 Beds
  • 2.5 - 3.5 Baths
  • 1,966+ Sq Ft

  St Paul Plan at Winchester Ridge Townhomes, Winchester, VA 22602

  Introducing the St. Paul, one of Maronda’s latest townhome designs.The St. Paul offers a range of 1,966 to 1,989 square feet of living space, including 3 to 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious 1-car garage. This new design offers plenty of personalization opportunities to fit your family’s unique needs.On the first floor of the home, you will find a spacious, open-concept floor plan.

  Maronda Homes Builder

  161 Williamson Rd Unit 37409245, Winchester, VA 22602
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  /18

  $382,990

  New Construction $25K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  112 Sioux Loop, Winchester, VA 22602

  This Adams interior unit features 4 bedrooms, 3.5 baths, and a 1-car garage. With a total of 1,889 sq ft, there is plenty of space to entertain and live comfortably. Enjoy 9' ceilings and luxury vinyl plank flooring on the main level. The kitchen features white cabinets with quartz countertops along with stainless steel appliances by Whirlpool. Relax on your 8'x14' rear deck and take advantage of

  D.R. Horton Builder

  112 Sioux Loop, Winchester, VA 22602
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  /34

  $799,000

  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
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  /4

  $74,000

  • Land
  • 40,510 Sq Ft
  • $79,570 per Acre

  Lot 315A Timber Ridge Trail, Winchester, VA 22602

  Rare Double Lot – Nearly One Acre of Prime Ridge Top Privacy in Shawneeland! This exceptional, nearly one-acre, double lot offers a perfect blend of privacy and potential - and is ready for you to build the home of your dreams! Nestled atop the ridge in Shawneeland, this wooded parcel has been perc’d and approved for a three-bedroom septic system, with a certification letter on file with the

  Kristin Crosby Samson Properties

  Lot 315A Timber Ridge Trail, Winchester, VA 22602
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  /17

  $199,900

  $15K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $555,278 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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  $3,175,000

  • 6 Beds
  • 7 Baths
  • 8,593 Sq Ft

  730 Merrimans Ln, Winchester, VA 22601

  A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm

  Justin Mistretta Berkshire Hathaway HomeServices PenFed Realty

  730 Merrimans Ln, Winchester, VA 22601
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  /39

  $449,900

  • 2 Beds
  • 2 Baths
  • 2,370 Sq Ft

  443 Fairmont Ave, Winchester, VA 22601

  So much potential !!! Great location, private yard, lots of square feet. Lot is 3/4 acre !Needs TLC. Listed $120,000 under tax assessment to allow room for updating. Kitchen has Corion counter tops , great cabinets. Very large room with beautiful book case built in, has fantastic screened in porch, Very large ( 24 X 24 ) family room with fireplace .

  Jeff Webber Long & Foster Real Estate, Inc.

  443 Fairmont Ave, Winchester, VA 22601
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  /22

  $459,990

  New Construction

  • 2 - 3 Beds
  • 1 Bath
  • 1,670+ Sq Ft

  Fitzgerald Plan at Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection, Winchester, VA 22603

  Welcome to your dream one-level villa, the Fitzgerald! This beautifully designed home features a central kitchen that serves as the heart of the house, perfect for both everyday living and entertaining. The main level includes two spacious bedrooms, including a luxurious primary suite with an expansive walk-in closet and an en suite bathroom for your comfort and privacy. Additionally, you'll find

  Brookfield Residential Builder

  105 Wagtail Ln Unit 36578849, Winchester, VA 22603
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  $215,000

  $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 637 Sq Ft

  106 Blackfeet Trail, Winchester, VA 22602

  Charming mountain retreat nestled on a full acre in Shawneeland! This cozy 1-bedroom, 1-bath cabin offers the perfect blend of privacy, nature, and modern comfort. Situated on two combined lots totaling approximately 1 acre, the property provides plenty of space to enjoy the peaceful wooded setting.Recent improvements include a newer architectural shingle roof, gutter, vinyl clad double

  Tiffany Feathers-Brown MarketPlace REALTY

  106 Blackfeet Trail, Winchester, VA 22602
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  /15

  $374,990

  New Construction $17K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,752 Sq Ft

  105 Heirloom Way, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  105 Heirloom Way, Winchester, VA 22603
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  /14

  $509,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,216 Sq Ft

  101 Seminole Dr, Winchester, VA 22602

  The Glendale is a 2,216 square foot corner homesite, open concept two-story home with a finished basement that offers four bedrooms, three and a half bathrooms with a two-car garage. You will immediately feel at home as you enter the foyer and make your way into the spacious family room. This living space flows nicely into the eat-in kitchen with plenty of cabinets and island overlooking the

  D.R. Horton Builder

  101 Seminole Dr, Winchester, VA 22602
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  /22

  $549,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,476 Sq Ft

  206 Williamson Rd, Winchester, VA 22602

  The to be built Avalon is a stunning 3‐bedroom, 2‐bath home offering up to 2,538 square feet of thoughtfully designed living space. This single‐family layout emphasizes main‐level living with an open floor plan that brings together a spacious great room, a bright, airy kitchen, and a welcoming breakfast area. The main level includes three bedrooms and two full baths, with the option to transform

  Greta Fernandez New Home Star Virginia, LLC

  206 Williamson Rd, Winchester, VA 22602
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  /16

  $390,790

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,094 Sq Ft

  2435 Coriander Dr, Winchester, VA 22603

  Brand-New 4-Bedroom End Unit—Late Summer Move-In!Step into modern living with this stylish new-construction end-unit townhome, ideally located just steps from Snowden Bridge’s newest amenities. An entry-level bedroom with full bath offers the perfect setup for guests, multigenerational living, or added flexibility.Upstairs, light-filled open-concept living shines, with a sleek kitchen

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  2435 Coriander Dr, 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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  /96

  $459,999

  $30K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 1,887 Sq Ft

  419 Summit Ave, Winchester, VA 22601

  Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
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  /58

  $565,000

  Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 3,829 Sq Ft

  114 Nassau Dr, Winchester, VA 22602

  4 bed/ 3.5 bath colonial in a prime commuter location just minutes from I-81 and Route 7. Enjoy outdoor living with a fenced backyard, low-maintenance composite decking, brick patio, outdoor fireplace, and a storage shed! The spacious primary suite includes a large walk-in closet and sitting room. The finished basement is ideal for entertaining, featuring a full bath and wet bar. Recent upgrades

  Sheila Pack RE/MAX Roots

  114 Nassau Dr, Winchester, VA 22602
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  $539,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,279 Sq Ft

  104 Wagtail Ln, Winchester, VA 22603

  *****LENDER CREDIT WITH AN OFFER AND USE OF LENDER!!!*****Welcome to the Vale at Hiatt Pointe—THIS IS ONE OF A KIND WITH THIS VIEW! a brand-new 2025 end-unit villa that is ready for immediate move-in. This beautifully upgraded two-car front-load garage home features three bedrooms, two full baths, and one half bath, offering the perfect blend of style, comfort, and convenience.Enjoy peace

  Katy Donovan Keller Williams Realty

  104 Wagtail Ln, Winchester, VA 22603
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  /18

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  132 Geronimo Trail, Winchester, VA 22602

  Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet and highly desirable neighborhood, this charming single-family home is perfect for first-time buyers, downsizers, or anyone seeking a peaceful retreat. This 1,232 square-foot rancher features 3 bedrooms, 2 full bathrooms, eat-in kitchen, living room, a brick fireplace with highly a efficient wood-burning

  Shane Price Long & Foster Real Estate, Inc.

  132 Geronimo Trail, Winchester, VA 22602
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  /24

  $324,900

  New Construction $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,152 Sq Ft

  212 Falcon Trail, Winchester, VA 22602

  Nearing completion! 1/3 Acre – No Carpet!This affordable 2-bed, 2.5-bath home offers high-end finishes and incredible growth potential.Premium Finishes: Hardwood floors throughout (including all bedrooms), tile in all baths, and granite kitchen countertops.Open Layout: Bright family room and a spacious kitchen/dining area perfect for entertaining.Owner’s Suite: Large master

  Jim Thomson Realty ONE Group Old Towne

  212 Falcon Trail, Winchester, VA 22602
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  /2

  $139,900

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  130 Wollaston Dr Unit A34, Winchester, VA 22603

  COMING SOON! Currently under construction. Welcome to Regency Lakes, an all age active and vibrant community, where your dream home is coming to life. We are excited to offer a brand new, 2026 3 bed, 2 bath home for sale, featuring approximately 1564.80 sq ft of thoughtfully designed living space. Located in Winchester, this soon-to-be-completed property will offer the perfect blend of modern

  Kristina Kelly Regency Lakes

  130 Wollaston Dr Unit A34, Winchester, VA 22603
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  $2,200,000

  • 5 Beds
  • 4.5 Baths
  • 5,884 Sq Ft

  2230 Jones Rd, Winchester, VA 22602

  Set on 21.5 acres just minutes from downtown Winchester, this 5-bedroom home offers over 5,800 finished square feet with a blend of space, functionality, and outdoor living in a highly convenient location. Combining usable land, thoughtful improvements, and indoor and outdoor entertaining spaces, this property offers a rare opportunity close to town amenities. While a neighboring property's drive

  Jennifer Sacco RE/MAX Roots

  2230 Jones Rd, Winchester, VA 22602
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  /12

  $17,000

  • Land
  • 16,552 Sq Ft
  • $44,737 per Acre

  Lot 231 Timber Ridge, Winchester, VA 22602

  This lot is located in the Shawneeland community of northwestern Frederick County, Virginia on the western-facing slope of Great North Mountain. Level and partially treed, it's a spectacular place to build your weekend getaway cabin or year-round home. Swim in Shawneeland's spring-fed lake, fish, hike, and picnic, or simply enjoy the quiet beauty of nature. Located just 12 miles from

  Rebecca McTavish Long & Foster Real Estate, Inc.

  Lot 231 Timber Ridge, Winchester, VA 22602
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  /40

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft

  167 Falcon Trail, Winchester, VA 22602

  Discover the perfect blend of comfort and charm of this contemporary home nestled on a large 0.69-acre lot in Shawneeland! Built in 2007, this inviting residence features 1,470 finished square feet of thoughtfully designed living space, plus a spacious unfinished walk-out basement ready for your imagination and finishing touches! Step inside to find a warm and welcoming atmosphere within this

  Bridget Aikens Colony Realty

  167 Falcon Trail, Winchester, VA 22602
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  /28

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
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  /33

  $399,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  1025 S Loudoun St, Winchester, VA 22601

  TONS OF UPGRADES! This home has been updated top to bottom. From the roof, windows, kitchen, bathrooms, light fixtures, HVAC, and so on. Located just 1 block from Handley High School, this home and all of its high end improvements make it a treasure waiting to be discovered. As you walk through this home you'll notice that a ton of care and thoughtfulness was put into what it is today. The

  Michael Sprague Samson Properties

  1025 S Loudoun St, Winchester, VA 22601
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  /5

  $22,500

  • Land
  • 21,344 Sq Ft
  • $45,918 per Acre

  Lot 181 Rockwood Trail, Winchester, VA 22602

  It's time to MAKE YOUR DREAMS A REALITY with this beautiful, nearly HALF-ACRE building lot on the PREMIUM VIEW-SIDE of Rockwood Trail - just 30 minutes from downtown Winchester! Picture a cozy, custom-built home nestled atop quiet Shawneeland, with a gentle breeze carrying whispers of nature and potential stunning valley vistas stretching as far as the eye can see. Approved for a two-bedroom

  Kristin Crosby Samson Properties

  Lot 181 Rockwood Trail, Winchester, VA 22602

Showing Results 121 - 160, Page 4 of 11