Winchester, VA Homes for Sale under $400,000

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  /32

  $395,000

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft

  151 Mccormick Cir Unit 201, Winchester, VA 22602

  Price improvement!! Experience Effortless 55+ Living at Winchester Landing – The Sapphire by Ryan Homes Discover the perfect blend of comfort and convenience in the Sapphire model, a spacious single-level condo offering over 1,500 sq. ft. of thoughtfully designed living space. The open-concept layout seamlessly connects a modern kitchen, large island, and bright great room, creating an inviting

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  (540) 787-2320

  151 Mccormick Cir Unit 201, Winchester, VA 22602
• Explore Winchester

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  /23

  $320,000

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft

  27 Jackson Ave, Winchester, VA 22601

  Completely renovated and move-in ready, this charming 3 bedroom, 1 bath home is ideally located just minutes from downtown Winchester's shops, dining, and entertainment. Inside, you'll find beautiful hardwood floors throughout and a brand new kitchen and fully renovated bathroom. Major updates to the home include a new roof, new windows, new HVAC system, new hot water heater and new electric all

  

  Mikiala Whitacre

  ERA Oakcrest Realty, Inc.

  (540) 590-5591

  27 Jackson Ave, Winchester, VA 22601
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  /36

  $365,000

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft

  127 Shirley St, Winchester, VA 22601

  Comfortable living at this split-foyer home located in the heart of the City of Winchester. On the main level, you’ll find three bedrooms and a full bath. The lower level features a fourth bedroom plus a second full bath — ideal for guests, or a home office. Location is a standout. You’re just minutes from downtown dining, shopping, and community events, and enjoy easy access to schools, parks,

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 802-5087

  127 Shirley St, Winchester, VA 22601
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  /25

  $379,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  230 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Home with Deck! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. The main level includes a private finished recreation room and possible 4th bedroom with its own

  DRB Homes Builder

  230 Monteith Dr, Winchester, VA 22601
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  /39

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft

  100 Maury Way, Winchester, VA 22602

  Welcome to this Former Model Home for the Grand Nassau model by Ryan Homes - once the Winchester Landing 55+ community's showcase villa, thoughtfully designed to highlight elegant architecture, stylish finishes, and countless upgrades. Perfectly positioned on a desirable corner lot with expanded green space, this home blends sophistication with comfort, creating a lifestyle that feels both

  Matt Boyer Keller Williams Realty

  100 Maury Way, Winchester, VA 22602
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  /26

  $369,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  222 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Condo with Box Bay Windows! Explore Winchester’s new luxury townhome community. This three level home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height. The first

  DRB Homes Builder

  222 Monteith Dr, Winchester, VA 22601
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  /26

  $389,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  Bedford II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Box bay rear window and 10' x 14' Trex deck. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  DRB Homes Builder

  0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
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  /24

  $389,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  210 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm Beautiful open concept living 3 level townhome with Lower Level Walkout! The Bedford II 3 level interior town home with a box bay window with 1 car garage featuring 3 Bedrooms and 3.5 Baths and 1,784 square feet. It is fully finished top to bottom. The front door with the electronic Ring door camera leads directly into the spacious lower-level recreation

  DRB Homes Builder

  210 Monteith Dr, Winchester, VA 22601
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  /30

  $379,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  209 Monteith Dr, Winchester, VA 22601

  OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Condo with Deck! Explore Winchester’s new luxury townhome community. This three level home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. The main level includes a private finished recreation room and possible 4th bedroom with its own full bath and

  DRB Homes Builder

  209 Monteith Dr, Winchester, VA 22601
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  /11

  $374,990 New Construction

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

  Northgate Plan at Hiatt Pointe at Snowden Bridge - 55+ Villas Collection, 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 Wagtail Ln Unit 36578847, Winchester, VA 22603
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  /50

  $375,000

  • 4 Beds
  • 3 Baths
  • 1,617 Sq Ft

  126 Armstrong Place, Winchester, VA 22602

  SHORT SALE: All brick ranch home with 4 bedrooms close to town and a short walk to the golf course! Main level large living Room and dinning room, 2 bedrooms and 2 bathrooms, an eat in kitchen, has gleaming hardwood flooring. Lower Level large area for pool table 2 more bedrooms, 1 bathroom and a family room equipped with a brick fireplace and space for a pool table. There is a sliding glass door

  John Scully Colony Realty

  126 Armstrong Place, Winchester, VA 22602
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  /42

  $314,900

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft

  140 Mccormick Cir Unit 302, Winchester, VA 22602

  Welcome home to this gorgeous, like-new condo located in scenic and historic Winchester! This this gleaming home was just constructed and offers the perfect blend of modern elegance and cozy comfort. Enjoy top-tier finishes like quartz countertops, stainless steel appliances, and beautiful LVP flooring throughout. Relax and unwind on your private balcony overlooking the meticulously manicured

  Karl Achstetter Keller Williams Realty

  140 Mccormick Cir Unit 302, Winchester, VA 22602
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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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  /70

  $379,000

  • 3 Beds
  • 2.5 Baths
  • 1,631 Sq Ft

  313 Beaver Trail, Winchester, VA 22602

  Ring in the New Year with the perfect home! Beautiful Craftsman-style home in great Shawneeland location. Over 1600 Finished Square Feet with a Full Unfinished Basement. 3 Bedrooms, 2.5 Baths. Main level Primary Bedroom with Full Bath. Engineered Hardwood flooring in Living Room, Family Room, Dining Area and Kitchen, Upgraded Cabinetry throughout home. Oak Staircase and Railing. Upper Level has 2

  Dana Durr CENTURY 21 New Millennium

  313 Beaver Trail, Winchester, VA 22602
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  /63

  $365,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  508 Grouse Dr, Winchester, VA 22602

  Nestled in the charming Wilde Acres community, this stunning new construction home, completed in 2025, offers a perfect blend of modern design and traditional comfort. The Colonial architectural style, adorned with durable vinyl siding, invites you into a warm and welcoming space. Step inside to discover a thoughtfully designed interior featuring a traditional floor plan that seamlessly connects

  Steve DuBrueler Coldwell Banker Premier

  508 Grouse Dr, Winchester, VA 22602
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  /43

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,580 Sq Ft

  420 Russelcroft Rd, Winchester, VA 22601

  Welcome to 420 Russelcroft Road — the house that practically checks all your boxes *and* puts a smile on your face while doing it. With 1,580 square feet of comfortable living space, this 3-bedroom, 2-bath beauty has all the right vibes. The hardwood floors throughout most of the home give it a touch of class (and make cleaning a breeze), while the carpeted bedrooms give you that perfect excuse

  Brian Yoder Realty ONE Group Old Towne

  420 Russelcroft Rd, Winchester, VA 22601
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  /13

  $374,990 New Construction

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

  123 Castaway Place, 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

  123 Castaway Place, Winchester, VA 22603
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  /24

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  129 Jalapa Trail, Winchester, VA 22602

  Mountain Views & Modern Perfection: Your Turnkey Retreat Awaits!Seller offering buyer credit Welcome to your completely renovated sanctuary at 129 Jalapa Trail, where breathtaking Virginia mountain vistas meet the peace of mind of brand-new everything. Nestled on a private 1.35-acre lot, this charming home is the perfect blend of rustic tranquility and modern convenience—just 7 miles from the

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
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  /34

  $399,000

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

  318 E Piccadilly St, Winchester, VA 22601

  This delightful brick Colonial, perfectly situated in the heart of downtown Winchester, combines classic architecture with modern updates and an unbeatable location close to every downtown amenity, including restaurants, schools, shopping, parks, and major commuter routes. The home welcomes you with a large foyer featuring newly refinished hardwood floors that extend throughout the entire

  Dan Whitacre Colony Realty

  318 E Piccadilly St, Winchester, VA 22601
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  /44

  $319,000

  • 1 Bed
  • 1 Bath
  • 1,348 Sq Ft

  242 Footstone Ln, Winchester, VA 22603

  Peaceful Country Retreat on 4.7 Acres – Minutes from WinchesterThis private country home combines solid craftsmanship with serene mountain views. Located on a quiet gravel lane with a road maintenance agreement, the property features a durable stone-and-brick exterior and hardwood floors throughout. Inside, two stone fireplaces—including one in the primary bedroom—add warmth and character.

  Kristina Towns Weichert Realtors - Blue Ribbon

  242 Footstone Ln, Winchester, VA 22603
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  /3

  $384,880 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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  /21

  $384,900

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
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  /21

  $389,880 New Construction

  • 3 Beds
  • 4 Baths
  • 1,989 Sq Ft

  117 Boone Ct, Winchester, VA 22602

  Immediate Move-in at Rossum Crossing! Winchester's newest and most popular townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a

  Dorelba Estrada New Home Star Virginia, LLC

  117 Boone Ct, Winchester, VA 22602
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  /27

  $364,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  DELMAR Plan at Retreat at Winding Creek - Townhomes, Winchester, VA 22602

  The Delmar by D.R. Horton is a stunning new construction 2 story townhome plan featuring 1,500 square feet of living space including 3 bedrooms, 2.5 baths and a 1-car garage. The convenience of townhome living meets the amenities of a single-family home with the Delmar. The main level eat-in kitchen with large pantry and modern island opens up to an airy, bright dining and living room. The upper

  D.R. Horton Builder

  137 Seminole Dr Unit 36203785, Winchester, VA 22602
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  /10

  $370,000

  • 4 Beds
  • 3 Baths
  • 1,868 Sq Ft

  126 N Euclid Ave, Winchester, VA 22601

  Discover this charming brick home that offers a perfect blend of classic character and modern convenience. This detached home features 4 spacious bedrooms and 3 full bathrooms, providing ample space for relaxation and privacy. The inviting living area boasts a cozy fireplace, ideal for creating warm memories during chilly evenings and on this level, you'll also have 2 bedrooms and a full bath.

  Marta Bingham Real Broker, LLC

  126 N Euclid Ave, Winchester, VA 22601
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  /30

  $335,000

  • 4 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  126 Plainfield Dr, Winchester, VA 22602

  Live in town on south end with a viable yard with two sheds, 4 bedrooms, some simple updates mostly from 2020, hardwood floors, over 1400sqft, no hoa, and close proximity to major road arteries. Utilities are public water, septic, and electric. Dbox and lines were replaced in 2012 (Septic number of bedrooms). Owner is licensed VA real estate agent.

  Dave Spence RE/MAX Roots

  126 Plainfield Dr, Winchester, VA 22602
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  /47

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,476 Sq Ft

  130 Mill Race Dr, Winchester, VA 22602

  Bright, well-maintained 3-bedroom, 2-bath ranch-style home just off Route 7 on a quiet, non–through street, with easy access to shopping, dining, and downtown Winchester. The open floor plan features cathedral ceilings, refinished hardwood floors, and updated light fixtures throughout, creating a warm and airy atmosphere.The renovated kitchen flows seamlessly into the living and dining areas

  Natasha Roberts Realty ONE Group Old Towne

  130 Mill Race Dr, Winchester, VA 22602
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  /16

  $350,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  718 Panther Dr, Winchester, VA 22602

  Brand-new construction in the Wilde Acres community of Frederick County! This newly completed 3-bedroom, 2.5-bath Colonial-style home offers approximately 1,512 finished square feet across three levels and sits on a spacious 0.25-acre lot. Designed for modern living, the main level features an open-concept layout with luxury vinyl plank flooring, a bright kitchen with pantry and upgraded

  Abby Walters Preslee Real Estate

  718 Panther Dr, Winchester, VA 22602
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  /13

  $349,999

  • 5 Beds
  • 2 Baths
  • 1,584 Sq Ft

  505 Green St, Winchester, VA 22601

  BACK ON THE MARKET DUE TO BUYER FINANCING AND NON PERFORMANCE. Charming 3-Level Split Home in the Heart of Winchester! This split level home could be your forever home! Surrounded by parks, top-rated schools, and everyday amenities. Quick access to Route 7 and Interstate 81 commuting is breeze! Upstairs, you’ll find three generously sized bedrooms and a full bathroom, offering a peaceful seperate

  Julissa Rodriguez Vaze Realty

  505 Green St, Winchester, VA 22601
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  /37

  $325,000

  • 4 Beds
  • 2 Baths
  • 1,450 Sq Ft

  3221 Laurel Grove Rd, Winchester, VA 22602

  This beautifully updated all-brick ranch in Winchester offers true main-level living and a peaceful country setting with incredible mountain views. A long circular driveway welcomes you to this turnkey home featuring a brand-new HVAC system, architectural roof, and modern finishes throughout. Inside, enjoy a renovated kitchen with stainless steel appliances, new cabinetry, and gorgeous

  Andrew Hopley Keller Williams Realty Centre

  3221 Laurel Grove Rd, Winchester, VA 22602
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  /32

  $379,000

  • 2 Beds
  • 2 Baths
  • 1,590 Sq Ft

  203 Crestwood Ln, Winchester, VA 22602

  Welcome home to this well-maintained property located in an established Winchester neighborhood. The property features a functional main-level layout with a bright living area and a sunroom that adds additional usable space. Recent updates include a roof installed around 5 years ago, new kitchen appliances, a new hot water heater, and new wood flooring. The kitchen offers ample cabinet and

  Jen Richards MarketPlace REALTY

  203 Crestwood Ln, Winchester, VA 22602
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  /2

  $390,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 1,582 Sq Ft

  121 Graywolf Trail, Winchester, VA 22602

  This fully renovated 4-bedroom, 2.5-bath home offers the perfect blend of comfort and functionality. The attached climate-controlled garage adds versatility—ideal for a home gym, workshop, or temperature-sensitive storage—while the deck provides great outdoor living space.

  Rocio Cossich Samson Properties

  121 Graywolf Trail, Winchester, VA 22602
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  /27

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,419 Sq Ft

  309 W Tevis St, Winchester, VA 22601

  Discover this Charming One-Level Rambler Featuring an Attached Two-Car Garage and a Thoughtful Layout Designed for Comfortable Living. Enjoy Spacious Bedrooms, Walk-In Closets, and a Warm Gas Fireplace that Anchors the Inviting Living Area. The Home Offers a Spacious Eat-In Kitchen, Providing Ample Room for Cooking, Dining, and Daily Gatherings. Step Outside to a Screened-In Deck, Perfect for

  Matthew Altizer ANR Realty, LLC

  309 W Tevis St, Winchester, VA 22601
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  /52

  $399,990 New Construction

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

  1814 Blythe Way, Winchester, VA 22601

  1814 Blythe Way is an attractive new 3 level townhome with full brick front in Winchester, VA for January move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful Quartz countertops, Stone Grey cabinets, and stainless-steel

  D.R. Horton Builder

  1814 Blythe Way, Winchester, VA 22601
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  /30

  $340,000

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft

  138 Windstone Dr, Winchester, VA 22602

  HAVE IT ALL! BEAUTIFUL 3-LEVEL TOWNHOUSE WITH A GAS LOG FIREPLACE, GARAGE AND A COMMUNITY SWIMMING POOL! Just east of Winchester and commuter convenient to I-81 and Rt. 7, shopping and services. An easy drive to Dulles Airport and Northern Virginia. Welcome to Windstone, a community with a fenced outdoor pool and plenty of places to walk. 3 bedrooms, 2 1/2 baths., including a primary suite with

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  138 Windstone Dr, Winchester, VA 22602
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  /22

  $399,000

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

  129 Jalapa Trail, Winchester, VA 22602

  Seller Credit - This beautifully renovated traditional home in Shawnee Land offers a perfect blend of comfort and modern living. With 3 spacious bedrooms and 2 full bathrooms, the layout is designed for both relaxation and functionality. The interior features a breakfast area and a traditional floor plan, complemented by wood flooring throughout. The full daylight basement provides ample space

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
• 

  

  /64

  $375,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  506 Grouse Dr, Winchester, VA 22602

  Nestled in the charming Wilde Acres community, this stunning new construction home, completed in 2025,offers a perfect blend of modern design and traditional comfort. The Colonial architectural style, adorned with durable vinyl siding, invites you into a warm and welcoming space. Step inside to discover a thoughtfully designed interior featuring a traditional floor plan that seamlessly connects

  Steve DuBrueler Coldwell Banker Premier

  506 Grouse Dr, Winchester, VA 22602
• 

  

  /23

  $374,990 New Construction

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

  105 Castaway Place, 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 Castaway Place, Winchester, VA 22603
• 

  

  /22

  $389,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  Lot 232 Inca Trail, Winchester, VA 22602

  Large lot (.47/acre) on private street with valley views. HW floors entire main floor and stairs, tile floors in all baths, BUILDER BONUS HARDWOOD TO INCLUDE BEDROOMS (no carpet in house), UPGRADED CABINETS, GRANITE COUNTERTOPS IN KITCHEN. New Colonial home. 3 bed, 2.5 full baths, open floor plan, family rm, Kitchen w/ island and breakfast rm & sep. dining rm, Lg owner suite & true master bath

  Jim Thomson Realty ONE Group Old Towne

  Lot 232 Inca Trail, Winchester, VA 22602
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  /20

  $319,000

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

  553 Highland Ave, Winchester, VA 22601

  Don't miss taking a LOOK at this property with the new low price of $319K. See you tomorrow at noon.............................. 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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