Winchester, VA Homes for Sale under $500,000

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  $449,990 New Construction

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

  1819 Reese Ct, Winchester, VA 22601

  1819 Reese Court is a move-in ready 3-level townhome with full brick front in Winchester, VA. 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 flooring. The kitchen is equipped with beautiful quartz countertops, sasparilla cabinets, and stainless-steel appliances. The upper

  D.R. Horton Builder

  1819 Reese Ct, Winchester, VA 22601
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  $415,000

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  4403 Back Mountain Rd, Winchester, VA 22602

  Nestled on two private wooded acres. New Roof 2023 - A peaceful country retreat with no HOA or restrictions. Colonial-style home features approximately 2,012 square feet of comfortable finished living space plus an unfinished basement. Includes 3 bedrooms and 2.5 baths. The walk-out basement provides excellent storage and potential for future expansion. The main level includes a spacious living

  RoxAnn Grimes RE/MAX Roots

  4403 Back Mountain Rd, Winchester, VA 22602
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  $439,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,920 Sq Ft

  1805 Harvest Dr, Winchester, VA 22601

  1805 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for February move-in. Our modern Adams II floorplan features a 1-car garage, and 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, white cabinets, and stainless-steel appliances. The

  D.R. Horton Builder

  1805 Harvest Dr, Winchester, VA 22601
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  $412,365 New Construction

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

  117 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

  117 Bonnings Dr, Winchester, VA 22603
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  $459,990

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  110 Elaine Dr, Winchester, VA 22602

  WELCOME HOME TO THIS BEAUTIFULLY RE-IMAGINED 3-BED, 2-BATH WINCHESTER GEM! THIS SINGLE FAMILY HOME HAS BEEN RECENTLY & METICULOUSLY RENOVATED FROM THE STUDS OUT (built in 1990). THIS HOME BLENDS TIMELESS CHARM WITH TODAY'S MODERN UPDATES. STEP INSIDE TO DISCOVER AN OPEN, LIGHT-FILLED FLOOR PLAN FEATURING RECESSED LIGHTING THRU OUT, A NEST THERMOSTAT TO REMOTELY CONTROL YOUR HOMES TEMPERATURE, A

  JoAnn Walker Century 21 Redwood Realty

  110 Elaine Dr, Winchester, VA 22602
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  $439,900

  • Studio
  • 2,376 Sq Ft

  510 N Loudoun St, Winchester, VA 22601

  All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD/1BA with unfinished attic, main floor is 1BR/1BA (Both have rear balcony) and basement unit has access to storage area and includes1BD/1BA. All units have washer/dryer (Basement unit washer/dryer belongs to tenant). Owner/Agent and home inspection report available upon request.

  Dave Spence RE/MAX Roots

  510 N Loudoun St, Winchester, VA 22601
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  $449,000

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

  570 Welltown Rd, Winchester, VA 22603

  Built to last but updated and move in ready! This charming brick home has a lot to offer. The location is perfect with quick access to I-81 for commuting, is only minutes away from restaurants, shopping and other amenities, and maybe best of all, it has a separate apartment on the lower level! The basement apartment has a bedroom, a full bathroom, full kitchen, a living area, as well as it's own

  Marielle Fusaro Keller Williams Realty

  570 Welltown Rd, Winchester, VA 22603
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  $429,990 New Construction

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

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

  The 1,889 sq. ft. Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1-car garage. You will love the granite counter tops, stainless steel appliances, and recessed lighting in the kitchen. Create the rec room, home office or 4th bedroom of your dreams in the lower level bonus space! The Adams comes with a 12'x10' deck off the rear of the home, perfect for outdoor

  D.R. Horton Builder

  137 Seminole Dr Unit 36203787, Winchester, VA 22602
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  $499,000

  • 3 Beds
  • 2 Baths
  • 2,094 Sq Ft

  101 Delaware Trail, Winchester, VA 22602

  Welcome to 101 Delaware Trail, a thoughtfully updated home nestled in the highly desirable Shawneeland community of Winchester, VA. Nearly the entire home has been updated, both inside and out, creating a fresh and modern living experience. Interior improvements include new flooring throughout (excluding existing wood flooring), an updated kitchen featuring Taj Mahal quartzite countertops, a

  Michael Putnam EXP Realty, LLC

  101 Delaware Trail, Winchester, VA 22602
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  $469,900

  • 3 Beds
  • 4 Baths
  • 3,359 Sq Ft

  227 Miller St, Winchester, VA 22601

  BE SURE TO WATCH THE VIDEO TOUR! Welcome to 227 Miller Street — a home that instantly feels inviting. Recent improvements include new flooring in both upstairs and downstairs bathrooms (2025), new toilets in all bathrooms (2024), refreshed hardwood floors (2025), a professionally cleaned chimney (2025). The back deck was replaced in 2024, and the home offers multiple outdoor spaces, including a

  Leah Marabella Realty ONE Group Old Towne

  227 Miller St, Winchester, VA 22601
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  $469,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  117 Wagtail Ln, Winchester, VA 22603

  Welcome to 117 Wagtail Lane, a brand-new Van Metre townhome located in the sought-after 55+ community of Hiatt Point at Snowden Bridge. Designed for low-maintenance living, this thoughtfully crafted home features an open-concept main level filled with natural light and a modern kitchen with stylish finishes—ideal for everyday living and entertaining. The spacious primary suite is located on the

  Lindsay Potter Real Broker, LLC

  117 Wagtail Ln, Winchester, VA 22603
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  $449,900

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  1105 Henry Dr, Winchester, VA 22602

  Home offers nearly 3000 sqft of finished living space that has Luxury Vinyl flooring through out both levels (absolutely no carpet) that features 4 bedrooms and 2.5 baths situated on over a 1/2 acre (.61) of ground. Upon entering you will find an open floor plan that encompasses a large living room and dining room with canned lighting then pours into the large eat in kitchen (new appliances) that

  James Amick RE/MAX Roots

  1105 Henry Dr, Winchester, VA 22602
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  $450,000

  • 4 Beds
  • 2.5 Baths
  • 2,072 Sq Ft

  129 Doonbeg Ct, Winchester, VA 22602

  ENJOY AN AFFORDABLE RETIREMENT! Newer, beautifully maintained 4-bedroom home with open floor plan and upgrades. In Cottage Glen, an age 55-plus community that's convenient to I-81 and Rt. 37 and near restaurants, shopping, services, regional Medical Center and historic downtown Winchester. National publications and TV have hailed Winchester as a prime location for retirement. Tucked away on a

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  129 Doonbeg Ct, Winchester, VA 22602
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  $409,990 New Construction

  • 3 Beds
  • 2 Baths
  • 2,060 Sq Ft

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

  Attached 1-car garage or flex option. Open concept kitchen with optional island opens to country kitchen, sun room, and living room. Alternative main level option available. Optional choices available include a study and a fireplace. Owner’s suite with a generous walk-in closet, dual vanity, and seated shower.

  DRB Homes Builder

  0 Tbd Weems Ln Unit 38608305, Winchester, VA 22601
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  $459,000 Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,884 Sq Ft

  108 Rawlings Ave, Winchester, VA 22603

  Welcome to this Nice Home, a 4 Bed 2 Bath split foyer home in the wonderful community of Dominion Knolls. This location is close to everything, minutes to Route 81. Great commuter location, with a 1-car garage with storage, a fenced backyard with concrete driveway, and a finished ground-level family Room with an adjacent large laundry/Utility room. New Carpet & Freshly Painted throughout! Must

  Maritza Munoz Samson Properties

  108 Rawlings Ave, Winchester, VA 22603
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  $409,990 New Construction

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

  Adams Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams I townhome offers 1,889 sq. ft. of thoughtfully designed living space, featuring 4 bedrooms, 3.5 bathrooms, and a convenient 1-car front-load garage. The modern kitchen showcases quartz countertops, stainless steel appliances, a spacious island, recessed lighting, and upgraded cabinets. Enjoy the flexibility of a finished lower-level bonus space—perfect for a rec room, home office, or

  D.R. Horton Builder

  1831 Reese Ct Unit 37025140, Winchester, VA 22601
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  $435,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,408 Sq Ft

  519 Whitacre St, Winchester, VA 22601

  Ideally located within one of Winchester’s most desirable neighborhoods, Whittier Acres, and next to Winchester Medical Center, this spacious split-level home offers exceptional convenience paired with a rare sense of privacy in a quiet, established setting. Backing to mature trees, the backyard is a peaceful retreat where birds visit regularly and an established butterfly garden awaits its

  Katie Landi Jordan Samson Properties

  519 Whitacre St, Winchester, VA 22601
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  $424,900

  • 3 Beds
  • 2.5 Baths
  • 2,547 Sq Ft

  113 Williamson Rd, Winchester, VA 22602

  **NEW PRICE** Welcome home to this solid all-brick rancher offering timeless charm and endless potential. Featuring 3 spacious bedrooms and 2.5 baths, this home blends comfort with opportunity. The updated kitchen provides a great foundation for everyday living and entertaining, while the full walkout basement expands your living space with a large recreation room highlighted by an in-wall gas

  Traci Shoberg Samson Properties

  113 Williamson Rd, Winchester, VA 22602
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  $415,000

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  307 Fox Dr, Winchester, VA 22601

  Ready for occupancy and fast settlement! Exceptional, spacious one-level home ideally located near the Medical Center, the Museum of the Shenandoah Valley, shopping, and downtown. This well-maintained property features newly refinished hardwood floors. The generously sized living room offers extensive built-in shelving and a wood-burning fireplace with mantle and hearth. Sliding glass doors open

  Darcy Amburn Colony Realty

  307 Fox Dr, Winchester, VA 22601
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  $459,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,905 Sq Ft

  Adams II Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams II townhome features 1,905 sq. ft. of stylish and flexible living space, including 4 bedrooms, 3.5 bathrooms, and a 1-car rear-load garage. The gourmet kitchen is equipped with quartz countertops, stainless steel appliances, recessed lighting, a generous island, and sleek Duraform cabinetry. The lower-level bonus room offers endless possibilities—use it as a rec room, home office, or an

  D.R. Horton Builder

  1831 Reese Ct Unit 37025141, Winchester, VA 22601
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  $414,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  119 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

  119 Heirloom Way, Winchester, VA 22603
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  $499,990 New Construction

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

  GLENDALE Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Glendale is a new construction home plan featuring 2,216 square feet of living space, 4 bedrooms, 3.5 baths and a 2-car garage. The Glendale gives you the features you’re looking for at the price you want! You’ll immediately feel at home as you enter into the spacious family room. This living space flows nicely into the eat-in kitchen which highlights a peninsula island overlooking the family

  D.R. Horton Builder

  137 Seminole Dr Unit 39403232, Winchester, VA 22602
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  $412,365 New Construction

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

  109 Boone Ct, 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

  109 Boone Ct, Winchester, VA 22602
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  $448,140 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,939 Sq Ft

  1817 Harvest Dr, Winchester, VA 22601

  1817 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for February move-in. Our modern Adams II floorplan features a 1-car garage, and 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, white cabinets, and stainless-steel appliances. The

  D.R. Horton Builder

  1817 Harvest Dr, Winchester, VA 22601
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  $428,140 New Construction

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

  1822 Blythe Way, Winchester, VA 22601

  1822 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA for February 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, white cabinets, and stainless-steel

  D.R. Horton Builder

  1822 Blythe Way, Winchester, VA 22601
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  $489,900 Open Sun 3PM - 5PM

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  703 S Loudoun St, Winchester, VA 22601

  Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Check. Endless possibilities? Check!!! This amazing property, located within the Historic Winchester District, presents a one-of-a-kind opportunity to own a piece of history - all just minutes from the Old Town mall. The front of the main home dates back to 1856! You will surely fall in love with the wood

  Kristin Crosby Samson Properties

  703 S Loudoun St, Winchester, VA 22601
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  $465,000

  • 4 Beds
  • 2.5 Baths
  • 1,634 Sq Ft

  21 W Pall Mall St, Winchester, VA 22601

  This inviting Winchester home offers a comfortable blend of character, functionality, and everyday convenience. The welcoming front porch creates a warm first impression and provides an ideal place to relax, unwind, or enjoy time outdoors. The fenced-in backyard offers added privacy and flexibility, making it well suited for entertaining, gardening, or simply enjoying open-air living. A private

  Sarah Reynolds Keller Williams Realty

  21 W Pall Mall St, Winchester, VA 22601
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  $429,990 New Construction

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

  123 Lakota St, Winchester, VA 22602

  Don't miss this fantastic Adams end-unit townhome with included deck, washer and dryer, and blinds! The Adams offers 4 bedrooms, 3.5 baths, and a 1-car garage spread across three levels with a total of 1,889 square feet. The main level features 9-foot ceilings, luxury vinyl plank flooring, white cabinets with granite countertops, and stainless steel appliances by Whirlpool. With all the smart

  D.R. Horton Builder

  123 Lakota St, Winchester, VA 22602

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