Winchester, VA Homes for Sale under $800,000

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  /21

  $579,990

  New Construction $20K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 3,127 Sq Ft

  114 Wappinger Terrace, Winchester, VA 22602

  The Hayden is a spacious two-story home offering 6 bedrooms, 4 bathrooms, and over 3,100 square feet of thoughtfully designed living space, perfect for both everyday living and entertaining. The main level features a versatile flex room off the foyer, ideal for a formal dining room, home office, or additional living space. The gourmet kitchen includes an oversized island with seating, a large

  D.R. Horton Builder

  114 Wappinger Terrace, Winchester, VA 22602
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  /16

  $759,900

  Open Sun 11AM - 1PM

  • 5 Beds
  • 4.5 Baths
  • 2,383 Sq Ft

  174 Williamson Rd, Winchester, VA 22602

  This spectacular, move-in-ready home shows like a professional model, showcasing exquisite designer touches, custom window treatments (included), and premium finishes throughout. Built in 2023, the residence offers the ultimate convenience of main-level living with a bright, open-concept layout that beautifully blends comfortable luxury with timeless appeal.Nestled on a spacious .28-acre

  Brenda Miller Berkshire Hathaway HomeServices PenFed Realty

  174 Williamson Rd, Winchester, VA 22602
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  /86

  $559,900

  • 2 Beds
  • 2.5 Baths
  • 2,031 Sq Ft

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601

  Experience a rare opportunity to own a piece of Winchester history at The Fort, one of Old Town's most distinctive residential communities. Located just blocks from the vibrant Walking Mall, this beautifully renovated 2-bedroom, 2.5-bath condominium seamlessly blends historic character with modern luxury.Unit 105 features an open-concept floor plan with soaring ceilings, rich

  Jen Richards MarketPlace REALTY

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601
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  /4

  $749,990

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,614 Sq Ft

  154 Williamson Rd, Winchester, VA 22602

  The Carlisle home design by Maronda Homes offers the perfect balance of style, space, and flexibility—designed to meet the needs of modern families and active lifestyles. Featuring 4 to 6 bedrooms, 2.5 to 5 bathrooms, and 3,614 square feet of living space, the Carlisle provides room to grow without sacrificing comfort or function.From the welcoming front entry to the spacious open-concept layout,

  Maronda Homes Builder

  154 Williamson Rd, Winchester, VA 22602
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  /69

  $675,000

  $24K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,738 Sq Ft

  158 Old Forest Cir, Winchester, VA 22602

  SELLER OFFERING ONE-YEAR STONEBROOK CLUB MEMBERSHIP! OPEN HOUSE SATURDAY, 1:00–3:00, SUNDAY, 2:00-4:00. Offering approximately 4,000 square feet of living space, welcome to 158 Old Forest Circle, a spacious and inviting Colonial nestled among mature trees in the desirable Stonebrook Farms community. This classic home features four bedrooms, two full baths and one half bath, along with a partially

  Mrs. Maria M Cunningham EXP Realty, LLC

  158 Old Forest Cir, Winchester, VA 22602
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  /59

  $600,000

  • 3 Beds
  • 1.5 Baths
  • 3,483 Sq Ft

  1311 Handley Ave, Winchester, VA 22601

  Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condition, this residence invites you to experience a blend of traditional elegance and modern comfort. Step inside to discover a thoughtfully designed interior featuring beautiful hardwood floors that flow seamlessly throughout. The

  Kim Hurst MarketPlace REALTY

  1311 Handley Ave, Winchester, VA 22601
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  /7

  $680,000

  New Construction $1K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  0 Tumble Leaf Ln, Winchester, VA 22602

  CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Main Level Living Evergreene model with standard 13' Family Rm CeilingsModel Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

  Daniel Boris Pearson Smith Realty, LLC

  0 Tumble Leaf Ln, Winchester, VA 22602
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  /2

  $646,090

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  2450 Cardigan Way, Winchester, VA 22603

  This 5‐bedroom Torrington home with a main‐level primary suite is still available to personalize—choose your own flooring, quartz countertops, cabinets, and fixtures, and move in early next year!The main level features luxury vinyl plank flooring and an open, light‐filled layout. The gourmet kitchen is appointed with stainless steel appliances, a statement range hood, quartz countertops, and

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  2450 Cardigan Way, Winchester, VA 22603
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  /26

  $749,900

  $16K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,220 Sq Ft

  175 Shields Dr, Winchester, VA 22602

  Beautiful 5 bedroom, 2.5-bath brick-front home situated on 2 private acres, offering the perfect blend of space, comfort, and recent updates. Shower on the main floor in laudry room, bonus room being used as a main floor bedroom. Major updates provide peace of mind, including a new roof (2025), HVAC systems replaced in 2023, 2024, and 2025, a new pressure tank, water heater, sump pump, Culligan

  Sheila Pack RE/MAX Roots

  175 Shields Dr, Winchester, VA 22602
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  /73

  $625,000

  Coming Soon Sep 11

  • 4 Beds
  • 3.5 Baths
  • 2,768 Sq Ft

  394 Old Baltimore Rd, Winchester, VA 22603

  Coming Soon! A truly special property in a gorgeous, peaceful setting! This charming 1911 farmhouse sits on 2.75 acres and offers the perfect opportunity for a small farmette, complete with a barn and large detached garage. Thoughtfully updated throughout the years while maintaining its farmhouse character, the home offers plenty of space and a rare, flexible layout with two primary suites - one

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  394 Old Baltimore Rd, Winchester, VA 22603
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  /48

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 2,325 Sq Ft

  414 N Braddock St, Winchester, VA 22601

  This charming farmhouse-style home,with off street parking, originally built in 1890 and beautifully renovated in 2018 (new windows, doors, HVAC, plumbing, drywall & insulation, electrical, kitchen & baths) offers the perfect blend of historic character and modern comfort in Old Town Winchester's Historic District, within walking distance of Downtown Winchester. Fresh interior paint and updated

  Sheila Pack RE/MAX Roots

  414 N Braddock St, Winchester, VA 22601

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