Winchester, VA Homes for Sale with Parking

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  $520,000

  • 5 Beds
  • 3.5 Baths
  • 2,854 Sq Ft

  105 Fairfield Dr, Winchester, VA 22602

  Back to Active Buyers Financing Fell Though Welcome to this generously sized 5-bedroom, 3.5-bathroom home located in the sought-after Oakdale Crossing community of Winchester, VA. This property offers a fantastic opportunity to personalize and update to your taste.Inside, you’ll find a bright, flowing floor plan featuring a large living room, formal dining area, and a spacious

  Ruby Miller Samson Properties

  105 Fairfield Dr, Winchester, VA 22602
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  /81

  $689,900

  • 4 Beds
  • 3.5 Baths
  • 4,411 Sq Ft

  226 Taggart Dr, Winchester, VA 22602

  Welcome to 226 Taggart Drive – a sunlit Colonial in the heart of Winchester's sought-after Raven Pointe community.This spacious 4-bedroom, 3.5 bath home offers over 4,200 square feet of beautifully finished living space across three levels, thoughtfully designed for comfort, functionality, and quiet everyday living. Nestled on a peaceful street just minutes from historic downtown Winchester,

  Lilly Triplett Colony Realty

  226 Taggart Dr, Winchester, VA 22602
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  /35

  $665,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  112 W Germain St, Winchester, VA 22601

  100-Year-Old Downtown Winchester Charmer – Brought Back to Life in 2025!This beautifully restored century-old home has been completely reimagined from the ground up, blending timeless character with top-tier modern upgrades. Located in the heart of historic downtown Winchester, this home underwent a full-gut renovation in 2025—everything is new. From the all-new electrical wiring and replaced

  Amanda Magana RE/MAX Roots

  112 W Germain St, Winchester, VA 22601
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  $615,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

  Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
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  /28

  $189,000

  • 2 Beds
  • 1 Bath
  • 644 Sq Ft

  792 Fox Dr, Winchester, VA 22603

  Charming 2-bedroom, 1-bath bungalow featuring hardwood floors in the living room and both bedrooms. The exterior has been freshly painted, giving the home a clean, updated look. Conveniently located near shopping and major highways, making commuting easy. Recent updates within the last 2.5 years include a new roof and replacement of most windows. A great opportunity with key improvements already

  Amanda Gulla Preslee Real Estate

  792 Fox Dr, Winchester, VA 22603
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  /52

  $475,000

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

  129 Jalapa Trail, Winchester, VA 22602

  Brand new everything, Roof, appliances, water treatment , bathrooms, deck, Sunroom, flooring Motivated Seller The perfect retreat for everyone, Welcome to your dream home in the heart of the Virginia Mountains , yet only 7 miles to the new Medical Center in Winchester. The property has access to the community lake, picnic grounds, play ground and loads of nature trails

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
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  $1,125,000

  • 4 Beds
  • 4 Baths
  • 4,949 Sq Ft

  1460 Pitcock Ln, Winchester, VA 22602

  Escape to Your Private Retreat – Just 10 Minutes from Winchester!Don’t miss the 3D tour attached to this listing!Welcome to a truly one-of-a-kind property offering 27.65 secluded acres across three parcels, complete with towering trees, a tranquil pond, and breathtaking natural surroundings. This charming log home is rich with character and history—originally relocated here in the

  Sheila Pack RE/MAX Roots

  1460 Pitcock Ln, Winchester, VA 22602
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  $1,074,900

  • 5 Beds
  • 7 Baths
  • 5,058 Sq Ft

  700 Miller Rd, Winchester, VA 22602

  Situated on a 2.5 acre lot in highly desirable area, this stunning Colonial home offers an open floor plan perfect for entertaining. Thoughtfully designed with a main-level ensuite and a second primary suite on the upper level; this home provides flexible living options for modern convenience. Spacious and filled with natural light, the home features a welcoming foyer, a beautiful kitchen, and

  Lilly Triplett Colony Realty

  700 Miller Rd, Winchester, VA 22602
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  /62

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  400 Great Mountain Ln, Winchester, VA 22602

  Please watch the Video! Escape to your own private mountain retreat with this stunning custom-built log home, offering breathtaking views of the Shenandoah Valley from an elevation of 1600 feet and 99+ acres of pristine land (elevation 2300+). Explore trails illuminated by solarlights—perfect for hiking,riding, and outdoor adventures. For shooting enthusiasts, a private range awaits, while an

  Leah Clowser RE/MAX Roots

  400 Great Mountain Ln, Winchester, VA 22602
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  /83

  $794,500

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

  127 Triangle Ct, Winchester, VA 22602

  One-year-young 4BR/4.5BA home in sought-after Abrams Pointe with over $158K in upgrades. Gourmet kitchen with quartz, custom cabinets, herringbone backsplash, & high-end appliances. Soaring 2-story great room, private office, and luxury primary suite with spa bath. Finished walk-up basement with full bath & potential 5th BR. 3-car garage, composite deck, & vinyl privacy fence. Enhanced HVAC with

  Shelley Hanrahan

  127 Triangle Ct, Winchester, VA 22602
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  $669,000

  • 4 Beds
  • 3.5 Baths
  • 3,008 Sq Ft

  355 Fishel Rd, Winchester, VA 22602

  Experience the epitome of homeownership with this stunning colonial home property perfectly set on 2.5+ acres of serene land just moments from all the conveniences of town. Offering the perfect blend of classic charm and modern amenities, this home is ideal for those seeking privacy without sacrificing accessibility. Thoughtfully designed with generous living spaces. Upon entering, you're greeted

  Daniel Brereton RE/MAX Roots

  355 Fishel Rd, Winchester, VA 22602
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  /36

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,296 Sq Ft

  224 Lauck Dr, Winchester, VA 22603

  Custom Home in Historic Star Fort: Timeless Charm Meets modern Comfort for Discerning Buyers.This impeccably designed 3-bedroom, 2.5-bath home is a harmonious blend of classic elegance and contemporary convenience. Boasting cherry wood flooring throughout the main living areas, high-quality tile in the kitchen and bathrooms, and carpeted bedrooms, this home is as stylish as it is practical.

  Gidget Smallwood Coldwell Banker Premier

  224 Lauck Dr, Winchester, VA 22603
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  /50

  $429,900

  • 5 Beds
  • 3.5 Baths
  • 1,776 Sq Ft

  103 Fenwick Ct, Winchester, VA 22602

  REDUCED! REDUCED!! REDUCED!!! Don't miss this well cared for home featuring 5 bedrooms and 3.5 bathrooms! It's located in a quiet neighborhood on a cul-de-sac and convenient to route 7 and Route 81 for commuters. NEW Large, private 6 car asphalt driveway so plenty of off-street parking! Whole length of house rear deck for entertaining! Featuring rare main level bedroom with attached full

  Sara Helmke Samson Properties

  103 Fenwick Ct, Winchester, VA 22602
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  /36

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,489 Sq Ft

  110 Hill Valley Dr, Winchester, VA 22602

  Charming 3-bedroom, 2.5-bath split-foyer home with inviting features and modern updates! The kitchen boasts beautiful wood floors, Corian countertops, stainless steel appliances, an island, a stylish backsplash, and a pantry for extra storage. The lower level offers a cozy family room, a convenient half bath, and a laundry area. Enjoy outdoor living on the exterior sun porch, stamped concrete

  Sheila Pack RE/MAX Roots

  110 Hill Valley Dr, Winchester, VA 22602
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  $765,000

  • 4 Beds
  • 3.5 Baths
  • 3,504 Sq Ft

  3980 Middle Rd, Winchester, VA 22602

  Custom, all-brick white rambler with a French Country ambience, enjoys boundaries of a lovely brook and a berm of boulders and indigenous plantings that obscures property from the roadway. All rooms are generously sized with the main level suitable for one-level living with Primary bedroom and laundry. Bedrooms on upper level are large enough for additional sitting area or study furnishings.

  Dallas Croft Samson Properties

  3980 Middle Rd, Winchester, VA 22602
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  $319,000

  • 4 Beds
  • 3.5 Baths
  • 1,840 Sq Ft

  205 Eastside Ln, Winchester, VA 22602

  Wonderful commuter location. Close to Rt. 7 and I-81. Property was previously occupied making it difficult to show. It is now ready to show at any time. Three bedrooms with a fully finished basement complete with a full bath that could become a 4th bedroom. Spacious living areas. Fenced in back yard. Property tucked in a small development right off of Route 7. Seller offering a $1500.00

  Kelly Bauer Coldwell Banker Premier

  205 Eastside Ln, Winchester, VA 22602
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  $649,000

  • 7,650 Sq Ft

  230 W Boscawen St, Winchester, VA 22601

  Multifamily, Professional Office, Historical Residence, or a combination of any of these opportunities! Even potential bed and breakfast or events center! Located in Historical Old Town Winchester, Holly House offers three floors, totaling over 7650 +/- SF, PLUS a HUGE outdoor English courtyard, ideal for urban gardening, building expansion, additional parking or pool! Iconic Federal Style

  Gillian Greenfield Coldwell Banker Premier

  230 W Boscawen St, Winchester, VA 22601
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  /2

  $350,000

  • 2 Beds
  • 1 Bath
  • 1,348 Sq Ft

  242 Footstone Ln, Winchester, VA 22603

  Peaceful Country Retreat on 4.7 Acres – Minutes from WinchesterDiscover the perfect blend of comfort, charm, and privacy in this unique country home, ideally situated just minutes from Winchester. Nestled on a quiet gravel lane with a road maintenance agreement in place, this beautifully maintained property features a timeless stone and brick exterior and rich hardwood floors throughout.

  Kristina Towns Weichert Realtors - Blue Ribbon

  242 Footstone Ln, Winchester, VA 22603
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  $395,985 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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  /3

  $399,480 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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  $549,990 New Construction

  • 3 Beds
  • 3 Baths
  • 2,264 Sq Ft

  120 Webster Ct, Winchester, VA 22603

  This new home is now under construction and contains our most popular structural options. As a myStyle home, you can personalize this home by selecting your favorite countertops, cabinetry, flooring, and fixtures! This exceptional Fitzgerald home, situated on a premium lot backing to green space and a farm, offers streamlined main-level living. Step inside the impressive two-story foyer

  

  Brookfield Residential

  Builder

  120 Webster Ct, Winchester, VA 22603
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  $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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  $560,329 New Construction

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

  102 Wagtail Ln, Winchester, VA 22603

  55+ Active Adult living just got better in Winchester Virginia with Hiatt Pointe, Van Metre Homes' newest gated community. You have to come see for yourself these stunning new single family and villa homes. Hiatt Pointe is a resort style community and has it all clubhouse, swimming pool, hot tub, pickleball and bocce ball courts, fitness center, outdoor kitchen and ample walking

  Cynthia Butler Samson Properties

  102 Wagtail Ln, Winchester, VA 22603
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  $669,409 New Construction

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft

  120 Magpie Ln, Winchester, VA 22603

  55+ Active Adult living just got better in Winchester Virginia with Hiatt Pointe, Van Metre Homes newest gated community. You have to come see for yourself these stunning new single family and villa homes. Hiatt Pointe is a resort style community and has it all clubhouse, swimming pool, hot tub, pickleball and bocce ball courts, fitness center, outdoor kitchen and ample walking

  Cynthia Butler Samson Properties

  120 Magpie Ln, Winchester, VA 22603
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  $399,990 New Construction

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

  102 Hopi Place, Winchester, VA 22602

  End unit townhome ready for a December/January move-in! The Delmar by D.R. Horton offers the perfect blend of comfort and style in this thoughtfully designed 2-story end-unit townhome. With 1,500 sq. ft. of living space, this home features 3 spacious bedrooms, 2.5 bathrooms, and a 1-car garage. On the main level, enjoy an open-concept layout with a bright and airy living room, dining area, and

  

  D.R. Horton

  Builder

  102 Hopi Place, Winchester, VA 22602
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  $534,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,415 Sq Ft

  224 Munsee Cir, Winchester, VA 22602

  The Elm is a modern two-story home offering 2,415 square feet, 5 bedrooms, 3 bathrooms, a loft, and a 2-car garage—designed to give everyone the space they need. As you enter through the distinctive foyer, you’ll appreciate the open-concept layout. The kitchen features abundant cabinetry, ample counter space, a large island with seating, stainless steel appliances, and pantry. The eat-in dining

  

  D.R. Horton

  Builder

  224 Munsee Cir, Winchester, VA 22602
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  $409,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,889 Sq Ft

  176 Munsee Cir, Winchester, VA 22602

  This new townhome featuring the Adams floorplan comes complete with 4 bedrooms, 3.5 bathrooms, and a 1-car garage. You will love the granite countertops, stainless steel appliances, and recessed lighting in the kitchen. Create the 4th bedroom of your dreams in the lower level bonus space! Other highlights include: Spacious 9 ft ceilings on the main level, over-sized kitchen island, upgraded

  

  D.R. Horton

  Builder

  176 Munsee Cir, Winchester, VA 22602
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  $409,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,889 Sq Ft

  180 Munsee Cir, Winchester, VA 22602

  This new townhome featuring the Adams floorplan comes complete with 4 bedrooms, 3.5 bathrooms, and a 1-car garage. You will love the granite countertops, stainless steel appliances, and recessed lighting in the kitchen. Create the 4th bedroom of your dreams in the lower level bonus space! Other highlights include: Spacious 9 ft ceilings on the main level, over-sized kitchen island, upgraded

  

  D.R. Horton

  Builder

  180 Munsee Cir, Winchester, VA 22602
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  $999,999 New Construction

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

  52 Cedar Grove Rd, Winchester, VA 22603

  This estate built on 7+ acres can be yours. Very private on wooded lot and sets nicely off the road. Close to town setting with no HOA. This home boosts one level living with 3,100 sq. ft. of open floor plan with so many features others would call them upgrades! Brick front with cement siding on three sides. Large concrete front porch with concrete lead walk. Builders upgrades: hardwood entire

  Jim Thomson Realty ONE Group Old Towne

  52 Cedar Grove Rd, Winchester, VA 22603
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  $539,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,415 Sq Ft

  230 Munsee Cir, Winchester, VA 22602

  Discover the perfect blend of space, function, and style in the Elm—a thoughtfully designed 2,415 sq. ft. two-story home featuring 5 bedrooms, 3 full bathrooms, a versatile loft, and a 2-car garage. Step into a welcoming foyer that opens to a bright, open-concept living area. The heart of the home is the spacious kitchen, complete with stainless steel appliances, generous cabinet storage, a

  

  D.R. Horton

  Builder

  230 Munsee Cir, Winchester, VA 22602
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  $369,990 New Construction

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

  104 Pomo Ln, Winchester, VA 22602

  Discover the Delmar by D.R. Horton—a thoughtfully designed interior townhome that combines comfort, style, and convenience. With 1,500 square feet of living space, this two-story home features 3 bedrooms, 2.5 bathrooms, and a 1-car garage, perfectly suited for low-maintenance living without sacrificing space. The main level offers an open-concept layout where the modern kitchen seamlessly

  

  D.R. Horton

  Builder

  104 Pomo Ln, Winchester, VA 22602
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  /27

  $369,990 New Construction

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

  102 Pomo Ln, Winchester, VA 22602

  Introducing the Delmar by D.R. Horton—a spacious and stylish interior townhome designed for easy, low-maintenance living. This two-story home offers 1,500 square feet of well-planned space with 3 bedrooms, 2.5 bathrooms, and a 1-car garage. The open-concept main level features a modern kitchen with a large island, plenty of cabinet space, and an oversized pantry—all flowing seamlessly into the

  

  D.R. Horton

  Builder

  102 Pomo Ln, Winchester, VA 22602
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  /27

  $369,990 New Construction

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

  106 Pomo Ln, Winchester, VA 22602

  Welcome to the Delmar by D.R. Horton—a beautifully crafted interior townhome offering the low-maintenance lifestyle you want with the space you need. This two-story home features 3 bedrooms, 2.5 bathrooms, a 1-car garage, and 1,500 square feet of smartly designed living space. Step inside to an open main level where the stylish kitchen flows effortlessly into the dining and living areas. You’ll

  

  D.R. Horton

  Builder

  106 Pomo Ln, Winchester, VA 22602
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  /23

  $499,990 New Construction

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

  228 Munsee Cir, Winchester, VA 22602

  Offering 1,964 square feet of modern living space, the Pine floor plan is perfect for growing families or those who love to entertain. This thoughtfully designed single-family home features four spacious bedrooms, two and a half bathrooms, and a two-car garage on a slab foundation for added convenience. The open-concept layout highlights a stylish kitchen with stainless steel appliances, granite

  

  D.R. Horton

  Builder

  228 Munsee Cir, Winchester, VA 22602
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  $604,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,511 Sq Ft

  111 Mascouten St, Winchester, VA 22602

  The Hayden is a three-story plan with 6 bedrooms and 4 bathrooms in 3,205 square feet. The main level features a flex room adjacent to the foyer, ideal for a formal dining room or home office. The gourmet kitchen has an oversized island for extra seating and a large pantry, and it opens to the dining area and a spacious living room. A bedroom with a full bathroom completes the main level. The

  

  D.R. Horton

  Builder

  111 Mascouten St, Winchester, VA 22602
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  /45

  $414,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,889 Sq Ft

  174 Munsee Cir, Winchester, VA 22602

  The Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1-car garage. You will love the granite countertops, stainless steel appliances, and recessed lighting in the kitchen. Create the 4th bedroom of your dreams in the lower level bonus space! Other highlights include: Spacious 9 ft ceilings on the main level, over-sized kitchen island, upgraded cabinets, stainless steel

  

  D.R. Horton

  Builder

  174 Munsee Cir, Winchester, VA 22602
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  /22

  $479,990 New Construction

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

  116 Webster Ct, Winchester, VA 22603

  Brand new, single level Hemingway with 10 year builder warranty is now ready for move in at Hiatt Pointe at Snowden Bridge, an active adult community for those 55 or better!!Tranquil living awaits in this luxurious garden home, ideally set on a premium, wooded lot that backs directly to a private farm, offering expansive open space and serene views. The sleek, open-concept design seamlessly

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  116 Webster Ct, Winchester, VA 22603
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  /43

  $609,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,618 Sq Ft

  113 Mascouten St, Winchester, VA 22602

  Introducing the Salem floorplan at The Retreat at Winding Creek! The first-floor owners' bedroom house you've been waiting for! On the main floor, you will find a formal dining room, laundry room, and half bath. The open-concept kitchen and living areas are perfect for entertaining. The kitchen has stainless steel appliances by Whirlpool with granite countertops. Upstairs are four additional

  

  D.R. Horton

  Builder

  113 Mascouten St, Winchester, VA 22602
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  /43

  $604,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,618 Sq Ft

  107 Mascouten St, Winchester, VA 22602

  Introducing the Salem floorplan at The Retreat at Winding Creek! The first-floor owners bedroom house you've been waiting for! On the main floor, you will find a formal dining room, laundry room, and half bath. The open-concept kitchen and living areas are perfect for entertaining. The kitchen has stainless steel appliances by Whirlpool with granite countertops. Upstairs are four additional

  

  D.R. Horton

  Builder

  107 Mascouten St, Winchester, VA 22602
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  /33

  $449,990 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

Showing Results 121 - 160, Page 4 of 7