Winchester, VA Houses for Sale

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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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  /71

  $849,900

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  251 Heather Hill Ln, Winchester, VA 22603

  Back on market at NO fault of seller. Have you been looking for peace and serenity, then you've found it. This gorgeous property offers almost 50 acres (there are several different parcels included in this sale. Parcels that are included are: 19-3-7 (house parcel, 5 acres), 19-3-10 (garage, pole barn parcel, 5 acres), 19-3-12 (7.79 acres), 19-A-48 (31.04 acres). The lovely Chalet offers 3

  Amber Jenkins Century 21 Redwood Realty

  251 Heather Hill Ln, Winchester, VA 22603
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  /60

  $660,000

  • 4 Beds
  • 2.5 Baths
  • 3,165 Sq Ft

  109 Aulee Ct, Winchester, VA 22602

  If you’re looking for a home that truly checks all the boxes, space, setting, style, and room to grow, this is the one you’ve been waiting for. Perfectly perched on a quiet cul-de-sac in the sought-after Twin Lakes Overlook neighborhood, this Toll Brothers built beauty offers more than curb appeal. It boasts a premium lot backing to the lake, with tranquil views that just might make you forget

  Kim Spear Keller Williams Realty

  109 Aulee Ct, Winchester, VA 22602
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  /77

  $824,999

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

  127 Triangle Ct, Winchester, VA 22602

  ***ONE-YEAR NEW, NEVER OCCUPIED! SELLER OFFERING CONCESSIONS TO BUYER FOR RATE BUY-DOWN OR CLOSING ASSISTANCE.*** Nestled in the sought-after Abrams Pointe community, this stunning 4 bedroom, 4.5 bath home is infused with countless designer upgrades, fine millwork, and craftsman-style design. A tailored exterior with front porch entrance, 3-car garage, composite deck, and expert landscaping are

  Shelley Hanrahan Shelley Shellz Sells Homes

  127 Triangle Ct, Winchester, VA 22602
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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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  /85

  $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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  /104

  $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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  /34

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,313 Sq Ft

  320 Highland Ave, Winchester, VA 22601

  Welcome to this centrally located home in the heart of Winchester. With easy access to I-81, this home is in a great commuter's location. Just a quick walk or drive away are the charming shops and restaurants of Historic Old Town Winchester. The main level features hardwood floors, a living room with wood-burning brick fireplace and a formal dining room, featuring a charming a built in China

  Heloisa Amar Samson Properties

  320 Highland Ave, Winchester, VA 22601
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  /2

  $250,000

  • 8 Beds
  • 5 Baths
  • 12,127 Sq Ft

  910 Franklin St, Winchester, VA 22601

  PRICE RARE UNIQUE OPPORTUNITY KNOCKS!ALL inside units cleaned, and junk removed - Ready for new investor.Warehouse also cleaned of junk and any hazards however has been condemned by City of Winchester as warehouse roof has caved in.Do not miss this rare opportunity to own this rare, unique property in Winchester. Work with the city of Winchester and turn this into your

  Pakeeza Akhtar The KOR Group, Inc.

  910 Franklin St, Winchester, VA 22601
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  /55

  $425,000

  • 5 Beds
  • 3.5 Baths
  • 3,333 Sq Ft

  1503 Valley Ave, Winchester, VA 22601

  Active again, Buyer's loan fell through. Charming Colonial located in the heart of Winchester. Only a few minutes walk to the Old Town Mall. This home features 5 bedrooms and 3 1/2 baths with 4 levels. There's a Primary Bedroom and Bathroom located on the main level with doors that open onto the back deck. The family room boasts hardwood floors and a wood burning fireplace. The kitchen is

  Julie Teets Long & Foster Real Estate, Inc.

  1503 Valley Ave, Winchester, VA 22601
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  /75

  $599,999

  • 4 Beds
  • 3.5 Baths
  • 3,084 Sq Ft

  1425 Cedar Grove Rd, Winchester, VA 22603

  Welcome to this spacious colonial situated on 4.75 acres in Winchester. With 4 bedrooms and 3.5 bathrooms, this home offers plenty of room and modern comforts. Key Updates:New Roof (2023) – Enjoy peace of mind with this recent upgrade.Brand New HVAC System – Featuring highly efficient heat pumps with a 90% efficiency rating.New Bosch Dishwasher – It's so quiet - no disruption while you're taking

  Katrina Smith RE/MAX Roots

  1425 Cedar Grove Rd, Winchester, VA 22603
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  /61

  $799,000

  • 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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  /40

  $415,000

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft

  128 Pioneers Rd, Winchester, VA 22602

  The previous contract was released through no fault of the seller. Great house in an excellent location just minutes from commuter routes and downtown Winchester. There are many recent improvements and upgrades to the kitchen and bathrooms. The bedrooms and living areas are nicely proportioned for comfortable living. Wonderful gas fireplace in the living room makes a beautiful focal point. This

  Erika De Azagra ERA Oakcrest Realty, Inc.

  128 Pioneers Rd, Winchester, VA 22602
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  /63

  $349,900

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

  525 Pheasant Dr, Winchester, VA 22602

  Absolutely beautiful home. When you walk into this lovely home, with its many upgraded fixtures, and freshly painted walls you will realize there is nothing you need to do but relax and enjoy your new home. Three bedrooms, 2 1/2 bathrooms and a gourmet kitchen with stainless steel appliances. Primary bedroom has two closets, one is a walk-in, and a private bathroom. French doors leading to a

  Jimmy Biedrzycki CENTURY 21 New Millennium

  525 Pheasant Dr, Winchester, VA 22602
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  /40

  $379,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  112 Fairway Dr, Winchester, VA 22602

  New roof just installed!This beautiful ranch-style home is located in a quiet cul-de-sac just minutes from downtown Winchester, Jim Barnett Park, and Shenandoah University. Ideal for commuters, with easy access to Route 7 and I-81.The home features 3 bedrooms and 1 bathroom, with a full, partially finished basement adding 600 sq ft of finished space. A convenient basement kitchenette

  Daniel Brereton RE/MAX Roots

  112 Fairway Dr, Winchester, VA 22602
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  /70

  $674,900

  • 4 Beds
  • 4.5 Baths
  • 4,395 Sq Ft

  113 Pangborne Ct, Winchester, VA 22602

  Back on the market at no fault of the seller! Space, space and more space! With nearly 4,400 finished square feet, this home can accommodate the needs of any buyer! Sitting on a quiet cul de sac on the desirable east side of Winchester, the location is ideal for commuters to NOVA as well as provides easy access to I-81. The spacious main floor offers a living room, formal dining room, study,

  Stephanie Ryall Realty ONE Group Old Towne

  113 Pangborne Ct, Winchester, VA 22602
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  /50

  $399,000

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

  126 Armstrong Place, Winchester, VA 22602

  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 that leads

  John Scully Colony Realty

  126 Armstrong Place, Winchester, VA 22602
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  /47

  $445,900

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

  103 Fenwick Ct, Winchester, VA 22602

  5 bedroom, 3.5 bathroom detached home! It's located in a neighborhood on a quiet cul-de-sac and convenient to route 7 and Route 81 for commuters. Large private 6 car new paved driveway -so plenty of off-street parking! Whole length of house rear deck for entertaining! Featuring rare main level bedroom with attached full bathroom. Plus, primary bedroom/primary full bathroom and 3 more bedrooms

  Sara Helmke Samson Properties

  103 Fenwick Ct, Winchester, VA 22602
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  /80

  $1,485,000

  • 4 Beds
  • 4.5 Baths
  • 5,754 Sq Ft

  291 Lake Serene Dr, Winchester, VA 22603

  An architectural masterpiece, true luxury is in every detail of this lakefront estate home. This unique property is nestled in a beautiful, peaceful natural setting, on a captivating private 25 acre lake with stunning panoramic views from the two expansive decks. (check out the video). The English Country- Style manor home was custom designed and completed in 2008. The property

  Cynthia Butler Samson Properties

  291 Lake Serene Dr, Winchester, VA 22603
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  /77

  $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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  /20

  $449,000

  • 5 Beds
  • 3 Baths
  • 2,560 Sq Ft

  106 Donna Cir, Winchester, VA 22602

  This beautiful, remodeled home is very well located, close to shopping and entertainment. The upstairs area features 3 spacious bedrooms, 2 full bathrooms. Also has sleek LVP floors throughout the home. The heart of the home is the sleek, all-new kitchen, equipped with shaker cabinets, quartz countertops, and stainless-steel appliances.The home offers a walkout basement with an independent exit,

  Marco Novillo Spring Hill Real Estate, LLC.

  106 Donna Cir, Winchester, VA 22602
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  /104

  $1,499,000

  • 5 Beds
  • 7 Baths
  • 9,447 Sq Ft

  103 Oak Ridge Ln, Winchester, VA 22602

  This luxury ranch estate boasts a whopping 8,295 square feet (with another 1,152 in the basement) on a lovely 1.5 acres. In 1998 the home was completely remodeled and expanded by the local, renowned architectural firm of Reader and Swartz. This home features beautiful, all-brick craftsmanship with herringbone details and hardscaping, curated landscaping, and mature trees for additional privacy.

  Dan Whitacre Colony Realty

  103 Oak Ridge Ln, Winchester, VA 22602
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  /17

  $385,000

  • 3 Beds
  • 2 Baths
  • 880 Sq Ft

  482 Diamondback Ln, Winchester, VA 22602

  Nestled on approximately 10 acres of serene land, this peaceful retreat offers minimal restrictions and features a picturesque stream that enhances the natural landscape. The cozy one-level home, approximately 880 sq. ft., was built in 2019 and served as a successful Airbnb, offering the perfect balance of comfort and privacy. Whether you're looking to unwind in nature or create your own private

  Sheila Pack RE/MAX Roots

  482 Diamondback Ln, Winchester, VA 22602
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  /39

  $312,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  127 S Euclid Ave, Winchester, VA 22601

  PRICE REDUCED!!!! BEATIFULL HOME!!! Fully Renovated Gem in the Heart of Winchester! Welcome to 127 Euclid , where modern upgrades meet timeless charm! This beautifully remodeled 3-bedroom, 2-bathroom rambler offers the perfect blend of comfort and convenience in one of Winchester’s most desirable locations. Step inside to discover a brand-new kitchen featuring stylish finishes, quartz

  Carolina Mosquera Weichert, REALTORS

  127 S Euclid Ave, Winchester, VA 22601
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  /56

  $2,098,000

  • 4 Beds
  • 2.5 Baths
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  Opportunity meets elegance in this fully remodeled multi-unit gem, perfectly situated in a prime in-town location. This unique property features four beautifully refinished homes and two modern apartments, offering both luxury and income potential in one impressive package.The main residence—currently owner-occupied—is a standout, seamlessly connected to a private indoor swimming pool, creating a

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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  /28

  $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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  /4

  $1,500,000

  • 3 Beds
  • 2 Baths

  821,839,851, lot44 Fox Dr, Winchester, VA 22603

  2.45 ACRES (4 current lots) ZONED RP WITH POTENTIAL CONVERSION FOR MIXED USE OR TOWNHOMES ECT. FRONTAGE ON FOX DRIVE CLOSE TO THE WINCHESTER MEDICAL CENTER AND DIRECTLY ACROSS FROM SUNNYSIDE PLAZA WITH KFC AND SHEETZ TO THE RIGHT OF PROPERTY. THREE EXISTING (RENTED $1,000/MONTH ON MONTH TO MONTH) HOMES AND VACANT LOT. PLATS AND TAX ID'S IN DOCUMENTS. EXISTING TOWNHOMES BACK RIGHT BEHIND

  Jim Thomson Realty ONE Group Old Towne

  821,839,851, lot44 Fox Dr, Winchester, VA 22603
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  /2

  $289,500

  • 4 Beds
  • 1 Bath
  • 1,732 Sq Ft

  1006 S Cameron St, Winchester, VA 22601

  Don't miss out on this opportunity to own this 5 bedroom/1 bath home. Hardwood flooring throughout. Large, covered front porch and rear deck. Less than a mile from downtown Winchester & the Handley Library. Close to schools. Off-street parking and a spacious backyard. Access to alley from backyard and off-street parking.

  Sheila Pack RE/MAX Roots

  1006 S Cameron St, Winchester, VA 22601
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  /25

  $670,434 New Construction

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

  108 Magpie Ln, Winchester, VA 22603

  Step into the Sierra 39-F2 – Homesite 1037 at Hiatt Pointe (55+)—a two-car, front-load garage SINGLE FAMILY home with three bedrooms and three full bathrooms will be ready AUGUST 2025. Designed for ease and everyday function, this factory-framed floorplan is as innovative as it stylish! Enter through the inviting front porch and be immediately welcomed by 9’ ceilings on both levels, oak main

  Shannon L Bray Pearson Smith Realty, LLC

  108 Magpie Ln, Winchester, VA 22603
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  /3

  $369,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  207 Otter Trail, Winchester, VA 22602

  This beautifully designed 3-bedroom, 2-bathroom home offers the perfect combination of modern comfort, single-level living, and thoughtful details—ideal for both growing families and retirees looking to downsize without compromise. With 1,560 sq. ft. of well-planned space, this home delivers everything you need in a manageable, low-maintenance package.As you step through the front door,

  Babak Taghavi Venture Realty

  207 Otter Trail, Winchester, VA 22602
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  /19

  $699,990 New Construction

  • 4 Beds
  • 3 Baths
  • 3,518 Sq Ft

  136 Magpie, Winchester, VA 22603

  Brand New Picasso is Ready for Move In at Hiatt Pointe at Snowden Bridge, a community for those 55 or better. The heart of the home is an open-concept haven, seamlessly blending a gourmet kitchen, dining room, and spacious family room. The kitchen, a chef's dream, features a functional island, stainless steel appliances, Carrara Morro Quartz counters, white and grey cabinets plus a large

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  136 Magpie, Winchester, VA 22603
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  /34

  $609,990 New Construction

  • 6 Beds
  • 4 Baths
  • 3,211 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

  Brooks Sears D R Horton Realty of Virginia LLC

  111 Mascouten St, Winchester, VA 22602
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  /57

  $609,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,619 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

  Brooks Sears D R Horton Realty of Virginia LLC

  113 Mascouten St, Winchester, VA 22602
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  /12

  $399,900 New Construction

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

  Lot 12 Doe, Winchester, VA 22602

  Complete by mid September. Almost 3/4 acre double lot (.69) low in community and close to entrance. Public water and Xfinity internet available. Brand new . 3 bed, 1,850 sq ft, 3 full baths, 2 car garage, open floor plan, family rm and kitchen with vault. HW floors entire main floor and stairs, tile floors in all baths, upgraded cabinets. BUILDER BONUS HARDWOOD IN BEDROOMS, BUILDER BONUS

  Jim Thomson Realty ONE Group Old Towne

  Lot 12 Doe, Winchester, VA 22602
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  /2

  $389,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,909 Sq Ft

  527 Grouse Dr, Winchester, VA 22602

  **7/10 - Many selections still able to be made within the next two weeks!** Welcome to your future dream home! Currently under construction, this beautifully designed split foyer blends modern living with classic comfort. Situated on a spacious 1/3-acre lot, this 1909 square foot home offers plenty of room to grow, relax, and entertain—inside and out.Step inside and experience the

  Shane Bowman RE/MAX Roots

  527 Grouse Dr, Winchester, VA 22602
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  /18

  $661,170 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,853 Sq Ft

  107 Malbec Ct, Winchester, VA 22602

  Quick move-in new construction in the desirable Abrams Pointe community! Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites.The Rockford Floorplan is a beautiful 4-bedroom, 2.5-bath home with up to 2,833 square feet of living space. This single-family home design features an open floor

  Dick Bryan New Home Star Virginia, LLC

  107 Malbec Ct, Winchester, VA 22602
• 

  

  /12

  $632,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,956 Sq Ft

  5 Williamson Rd, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites.The Drexel Floorplan is a spacious and versatile single-family home designed to suit a variety of lifestyles. With up to 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features

  Dick Bryan New Home Star Virginia, LLC

  5 Williamson Rd, Winchester, VA 22602
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  /29

  $619,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,847 Sq Ft

  4 Williamson Rd, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites.The Birmingham Floorplan is a beautiful 4-bedroom, 2.5-bath home with up to 3,717 square feet of living space. This single-family home design features an open floor plan, highlighted by a spacious great room, a light-filled kitchen, and a

  Dick Bryan New Home Star Virginia, LLC

  4 Williamson Rd, Winchester, VA 22602
• 

  

  /13

  $632,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,974 Sq Ft

  3 Williamson Rd, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites.The Carlisle Floorplan is a beautiful 4-bedroom, 2.5-bath home with up to 3,789 square feet of living space. This single-family home design features an open floor plan, highlighted by a spacious great room, a light-filled kitchen, and a breakfast

  Dick Bryan New Home Star Virginia, LLC

  3 Williamson Rd, Winchester, VA 22602
• 

  

  /27

  $611,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,542 Sq Ft

  0 Williamson Unit VAFV2034422, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites.The Somerset Floorplan is a beautiful 4-bedroom, 2.5-bath home that offers up to 3,514 square feet of living space. This single-family home design features an open floor plan, highlighted by a spacious great room, a light-filled kitchen, and a

  Dick Bryan New Home Star Virginia, LLC

  0 Williamson Unit VAFV2034422, Winchester, VA 22602

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