Winchester, VA Homes for Sale

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  /16

  $364,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,966 Sq Ft

  105 Bonnings Dr, Winchester, VA 22603

  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

  105 Bonnings Dr, Winchester, VA 22603
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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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  /53

  $650,000

  • 3 Beds
  • 4 Baths
  • 3,352 Sq Ft

  350 Plow Run Ln, Winchester, VA 22602

  Nestled on 2 beautiful acres in Frederick County, Virginia, this stunning ranch-style home offers the rare combination of peaceful country living with Comcast/Xfinity high-speed internet and cable TV — all just minutes from downtown Winchester! Custom built by a respected local builder and meticulously maintained, this home is loaded with quality finishes, functional space, and exceptional charm

  Leah Clowser RE/MAX Roots

  350 Plow Run Ln, Winchester, VA 22602
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  /48

  $399,500

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  155 Royal Ave, Winchester, VA 22602

  Super location in Winchester, VA. This property is located just past Costco off of Rte. 522S. Situated on a quiet street this Cape Cod has a wonderful covered front porch with the addition of a rear closed in porch. The main and upstairs have hardwood flooring. The main floor consists of a bedroom, full bath, living room,dining room, and a large kitchen with plenty of room for a breakfast area.

  Jim Stafford ERA Oakcrest Realty, Inc.

  155 Royal Ave, Winchester, VA 22602
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  /67

  $569,900

  • 3 Beds
  • 2.5 Baths
  • 2,450 Sq Ft

  1930 Harvest Dr, Winchester, VA 22601

  Experience the perfect blend of traditional charm and modern scale in this meticulously maintained residence located in the highly sought-after and established community of Meadow Branch South. The striking exterior, framed by a beautifully manicured lawn and mature landscaping, welcomes you into a soaring two-story foyer anchored by gleaming hardwood floors. The main level is designed for

  Dan Whitacre Colony Realty

  1930 Harvest Dr, Winchester, VA 22601
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  /62

  $305,000

  $35K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  105 Buckskin Trail, Winchester, VA 22602

  Nestled in the charming Shawneeland community, you will enjoy the mountain views in this delightful ranch-style home which offers a perfect blend of comfort and modern living. With a major renovation completed in 2026, this residence boasts a fresh and inviting atmosphere, ideal for creating lasting memories. The exterior features low-maintenance vinyl siding, complemented exterior lighting that

  Bruce Elsey Long & Foster Real Estate, Inc.

  105 Buckskin Trail, Winchester, VA 22602
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  /2

  $59,900

  $20K PRICE DROP

  • Land
  • 8,276 Sq Ft
  • $315,263 per Acre

  Lot 84 Purcell Ln, Winchester, VA 22603

  Build Your Vision Near Winchester City LimitsPrime buildable lot offering the perfect balance of convenience and freedom. Located just minutes from Winchester City but still in county, shopping, the hospital, and Route 37, this property is ready for your project with public water and sewer hookups available. Freedom to Build: No HOA or restrictive covenants—ideal for a custom small home or a

  Jim Thomson Realty ONE Group Old Towne

  Lot 84 Purcell Ln, Winchester, VA 22603
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  /41

  $389,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,405 Sq Ft

  1851 Melvor Ln, Winchester, VA 22601

  Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to

  RoxAnn Grimes RE/MAX Roots

  1851 Melvor Ln, Winchester, VA 22601
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  /3

  $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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  /109

  $1,150,000

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,880 Sq Ft

  199 Laurel Grove Rd, Winchester, VA 22602

  Nestled in the scenic countryside of Winchester, this impressive custom built home offers space, privacy, and beautiful Shenandoah Valley surroundings. Located in Frederick County, the property combines peaceful rural living with convenient access to shopping, dining, and commuter routes.Custom built in 2020, this spacious residence offers approximately 4,800+ square feet of living space on

  RoxAnn Grimes RE/MAX Roots

  199 Laurel Grove Rd, Winchester, VA 22602
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  /36

  $579,000

  • 4 Beds
  • 2.5 Baths
  • 2,316 Sq Ft

  120 Wales Ct, Winchester, VA 22602

  Nestled on a road that ends in a quiet cul-de-sac, 120 Wales Ct offers the perfect blend of comfort, privacy, and convenience. The home features an ideal flowing layout designed for both everyday living and privacy. The spacious owner’s suite is positioned on the right side of the home and offers an ensuite bathroom with a walk-in shower, soaking tub, and large walk-in closet. Three additional

  Kaitlyn Behr Samson Properties

  120 Wales Ct, Winchester, VA 22602
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  /18

  $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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  /44

  $656,990

  New Construction $3K PRICE INCREASE

  • 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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  /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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  /57

  $310,500

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

  406 Highland Ave, Winchester, VA 22601

  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 home, the owners have totally resurfaced and painted the metal roof, installed

  Lisette Turner Century 21 Redwood Realty

  406 Highland Ave, Winchester, VA 22601
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  /36

  $320,000

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. Great investment opportunity! Currently tenant-occupied, offering

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /27

  $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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  /43

  $475,000

  • 4 Beds
  • 2.5 Baths
  • 2,330 Sq Ft

  237 Asbury Rd, Winchester, VA 22602

  Welcome to 237 Asbury Road in Winchester tucked away on a quiet cul-de-sac yet perfectly located just off Rt. 7 for an easy commute. This 4-bedroom, 2.5 bath home offers a spacious, functional layout with multiple living areas, including a living room, separate dining room, and a family room with fireplace. The custom kitchen features granite countertops, a center island with prep sink, ample

  Stacey Mullins ERA Oakcrest Realty, Inc.

  237 Asbury Rd, Winchester, VA 22602
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  /41

  $395,900

  $13K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,615 Sq Ft

  114 Woodys Place, Winchester, VA 22602

  TOTALLY Renovated & Everything SHINES!! If this home had a Brand, it would be NEW!! The 3Br. 2 Ba. home features an excellent floorplan, providing an open & airy feel with skylights & cathedral ceilings that run the span of both levels. The main level features a master suite w/ private full bath, & walk in closet, the kitchen gleams with Top end appliances, gorgeous Granite countertops & abundant

  Dave Lyne Motion Realty, LLC

  114 Woodys Place, Winchester, VA 22602
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  /26

  $799,900

  New Construction

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

  169 Cather Ln, Winchester, VA 22602

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

  Kaitlyn Behr Samson Properties

  169 Cather Ln, Winchester, VA 22602
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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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  /24

  $519,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,953 Sq Ft

  TBD Munsee Cir, Winchester, VA 22602

  The Pine offers 1,964 square feet of modern living space - perfect for growing families or those who love to entertain. This well-designed single family home includes four spacious bedrooms, two and a half bathrooms, and a two-car garage on slab foundation. The open-concept design showcases a contemporary kitchen with stainless steel appliances, quartz countertops, and white cabinetry - combining

  D.R. Horton Builder

  TBD Munsee Cir, Winchester, VA 22602
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  /9

  $150,000

  • Land
  • 18,295 Sq Ft
  • $357,143 per Acre

  1322 Vanceright Cir, Winchester, VA 22601

  Tucked away on a quiet cul-de-sac, this 0.4174-acre lot offers a fantastic opportunity to build your dream home in a highly desirable Winchester location. Enjoy the convenience of being just minutes from Handley High School and the charm, dining, and shopping of downtown Winchester. The property features a 30' easement, allowing for access while still providing ample space for your vision. With

  John Scully Colony Realty

  1322 Vanceright Cir, Winchester, VA 22601
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  /27

  $459,990

  New Construction

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

  123 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

  123 Trellis View Ln, Winchester, VA 22602
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  /17

  $215,000

  • Land
  • 15,681 Sq Ft
  • $597,222 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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  /21

  $99,900

  • Land
  • 28,314 Sq Ft
  • $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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  /47

  $875,000

  • 4 Beds
  • 5.5 Baths
  • 5,054 Sq Ft

  125 Skyjes Ln, Winchester, VA 22602

  BACK ON THE MARKET! Custom-built modern farmhouse designed with comfort, flexibility, and multigenerational living in mind! This thoughtfully designed home, on 2 acres, welcomes you with an oversized family room featuring soaring 12-foot ceilings and an electric fireplace with a gas line already in place. A separate formal dining room with a stunning wall of windows creates the perfect setting

  Angie Bresnahan Pearson Smith Realty, LLC

  125 Skyjes Ln, Winchester, VA 22602
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  /55

  $579,000

  Open Sun 12PM - 2PM

  • 5 Beds
  • 3.5 Baths
  • 3,518 Sq Ft

  151 Travis Ct, Winchester, VA 22602

  Fantastic 5 bedroom, 3.5 bath colonial tucked away at the end of a quiet cul-de-sac in sought-after Red Fox Run. Offering three finished levels and backing to mature woods, this home combines space, privacy, and convenience on Winchester’s desirable east side.Step inside to find a bright open floor plan with a dramatic two-story foyer, hardwood flooring, and spacious living areas designed for

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  151 Travis Ct, Winchester, VA 22602
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  /22

  $469,990

  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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  /19

  $649,990

  New Construction $9K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,712 Sq Ft

  249 Hydrangea Way, Winchester, VA 22602

  The Dover by D.R. Horton offers 1,958 square feet of thoughtfully designed, single-level living with 3 bedrooms, 2 full baths, and a 2-car garage. A private flex room with LVP flooring sits just off the foyer – ideal for a home office or craft room. 9-foot ceilings lead into the open-concept kitchen, dining, and family room. The kitchen features quartz countertops, soft-close cabinet doors, a gas

  D.R. Horton Builder

  249 Hydrangea Way, Winchester, VA 22602
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  /36

  $385,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft

  13 E Leicester St, Winchester, VA 22601

  Incredible location, incredible home! Relax on the elevated front porch overlooking Leicester St, or retreat to the private back yard. Inside, gleaming wood floors and original trim compliment the new kitchen and bathrooms. HVAC, wiring, plumbing, windows, roofing, and siding have been lovingly replaced/updated in the last 5 years. This home is walkable to everything, and sits on a calm side

  William Steinmetz RE/MAX Roots

  13 E Leicester St, Winchester, VA 22601
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  /14

  $391,990

  New Construction

  • 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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  /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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  /8

  $399,999

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft

  217 Pembridge Dr, Winchester, VA 22602

  COMING SOON! Welcome to this well-maintained home in the sought-after Pembridge Heights community on the east side of Winchester. Conveniently located with easy access to Route 50, I-81, shopping, dining, and commuter routes, this property offers a blend of comfort, functionality, and numerous recent updates. The kitchen features granite countertops and updated appliances, including a

  Sue Goodwin Long & Foster Real Estate, Inc.

  217 Pembridge Dr, Winchester, VA 22602
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  /48

  $549,000

  $10K 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

  Kathrin Donovan Keller Williams Realty

  104 Wagtail Ln, Winchester, VA 22603
• 

  

  /17

  $285,000

  • Land
  • 40.2 Acres
  • $7,090 per Acre

  507 Easter Ridge Ln, Winchester, VA 22603

  Beautiful 40-acre wooded retreat with cabin and development potential! Discover the possibilities with this wooded property offering privacy, natural beauty, and future opportunity. Tucked away along a state-maintained road, this tract provides a secluded setting while still maintaining accessibility. The property features a charming rustic cabin, perfect for weekend getaways or a hunting

  Pamela Russell CENTURY 21 New Millennium

  507 Easter Ridge Ln, Winchester, VA 22603
• 

  

  /18

  $349,900

  New Construction $20K PRICE INCREASE

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

  212 Falcon Trail, Winchester, VA 22602

  Mearing completion! Current Shawneeland Inventory208 Beaver Trail (split foyer)210 Beaver Trail (split foyer)212 Falcon Trail (colonial)211 Inca Trail (colonial)103 Tonto Trail (split foyer)123 Killbuck Trail (colonial)1/3 Acre – No Carpet!This affordable 2-bed, 2.5-bath home offers high-end finishes and incredible growth potential.Premium Finishes: Hardwood

  Jim Thomson Realty ONE Group Old Towne

  212 Falcon Trail, Winchester, VA 22602
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  /83

  $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. The main living areas feature an

  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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  /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

Showing Results 121 - 160, Page 4 of 11