Winchester, VA 3-Story Homes for Sale

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  /23

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  514 Cather Ave, Winchester, VA 22601

  Welcome to this beautifully maintained home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today’s lifestyle. Step inside to a spacious main level featuring a bright and inviting family room, a dedicated dining area, and an eat-in kitchen—perfect for everyday living and entertaining. This home offers

  

  Paula Keiper

  EXP Realty, LLC

  (540) 452-9510

  514 Cather Ave, Winchester, VA 22601
• Explore Winchester

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  /67

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,530 Sq Ft

  229 Garber Ln, Winchester, VA 22602

  Welcome to 229 Garber Lane — Where Historic Charm Meets Prime Commercial Opportunity. Classic charm resides in this uniquely positioned B-2 commercially zoned property offering exceptional flexibility for renovation, redevelopment, or continued residential use. Situated on 1.65± prime acres, this property is surrounded by other B-2 zoned parcels and boasts outstanding visibility from I-81, making

  

  Jodi Cilley

  Realty ONE Group Old Towne

  (540) 329-2584

  229 Garber Ln, Winchester, VA 22602
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  /60

  $644,900

  • 4 Beds
  • 3.5 Baths
  • 3,490 Sq Ft

  128 Poe Dr, Winchester, VA 22602

  128 Poe Drive presents one of the largest models offered in the neighborhood, ideally positioned on a desirable corner lot with an expansive side yard in addition to the backyard. Built in 2023 and filled with upgrades, get ready to see one of the best homes in Winchester. Offering over 3,500 square feet with 4 bedrooms plus loft upstairs, including a finished basement, this home provides

  

  MJ Frazier

  Serhant

  (540) 515-5588

  128 Poe Dr, Winchester, VA 22602
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  /32

  $379,999

  • 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
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  /60

  $799,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 3,256 Sq Ft

  201 Nathaniel Dr, Winchester, VA 22603

  Stunning new construction modern contemporary home situated on nearly 6 private wooded acres, offering the perfect balance of privacy and convenience. This thoughtfully designed home features an open-concept layout filled with abundant natural sunlight and beautiful wooded views throughout.The main living area showcases engineered hardwood flooring, a spacious living room and dining area, and

  Renee Waymire Samson Properties

  201 Nathaniel Dr, Winchester, VA 22603
• 

  

  /18

  $564,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,747 Sq Ft

  25 Williamson Rd, Winchester, VA 22602

  Welcome to Abrams Pointe QUICK MOVE-IN HOME! The Rockford Floorplan is a beautiful 4-bedroom, 2.5-bath home over to 3000 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, a sunroom extension, and a breakfast area. On the second floor, you'll find 4 bedrooms and 2 bathrooms, including a large

  Greta Fernandez New Home Star Virginia, LLC

  25 Williamson Rd, Winchester, VA 22602
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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

  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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  /83

  $725,000 Open House 4/11

  • 3 Beds
  • 3 Baths
  • 3,052 Sq Ft

  171 Laurel Grove Rd, Winchester, VA 22602

  Historic 1800s farmhouse on 5 unrestricted acres just outside Winchester, Virginia, in desirable Frederick County. This 3-bedroom, 3-bath farmhouse blends historic charm with modern comfort and is equestrian-ready. Features include hardwood floors throughout, a farmhouse kitchen with wrap-around covered porch access, a dining room with a fireplace, a living room with a fireplace, and a den/office

  RoxAnn Grimes RE/MAX Roots

  171 Laurel Grove Rd, Winchester, VA 22602
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  /50

  $369,900

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft

  109 Huron Trail, Winchester, VA 22602

  Discover this inviting 3-bedroom, 2-bath tri‐level home, offering flexible living spaces and a unique layout designed for comfort and creativity. The main level features a bright kitchen and a welcoming living room, setting the tone for easy everyday living. The upper-level hosts three full bedrooms, including a comfortable primary suite with its own ensuite bath, along with a well‐appointed full

  LESLIE WEBB Long & Foster Real Estate, Inc.

  109 Huron Trail, Winchester, VA 22602
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  /94

  $950,000 Open Sat 11AM - 1PM

  • 6 Beds
  • 4.5 Baths
  • 4,714 Sq Ft

  226 Summerfield Dr, Winchester, VA 22602

  Nestled in the charming and sought-after Raven Pointe neighborhood,adjacent to farmland yet 7 minutes from Old Town Winchester, thisstunning Colonial home offers a perfect blend of modern comfort andtimeless elegance. This spacious residence boasts 4,714 finishedsquare feet, providing ample room for both relaxation andentertainment. Front porch entrance greets guests with a

  Rebecca Sims Century 21 Redwood Realty

  226 Summerfield Dr, Winchester, VA 22602
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  /41

  $355,000

  • 2 Beds
  • 2.5 Baths
  • 1,837 Sq Ft

  132 Seabreeze Ln, Winchester, VA 22602

  Amazing, end-unit townhome tucked in the back of sought after Windstone. Enjoy your own outdoor oasis from the spacious deck with stairs, overlooking the expanded, fully fenced yard, and surrounded by wooded common area behind and on the side. The inside is wonderfully kept, having been beautifully renovated , this home is truly a show-stopper! The main floor features updated flooring and paint

  Lisa Gill ERA Oakcrest Realty, Inc.

  132 Seabreeze Ln, Winchester, VA 22602
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  /52

  $574,900

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft

  104 Monet Terrace, Winchester, VA 22602

  Located in an established cul-de-sac this 4 bedrooms, 2 1⁄2 bath, home has an unfinished basement. Also a deep two vehicle garage and storage building with a fenced yard and rear covered porch. The kitchen has Corian counters and loads of beautiful cabinets, an arch pass through, and hardwood floors. The house has crown molding, chair rail, wainscoting and hardwood floors throughout the main

  Janet Jackson MarketPlace REALTY

  104 Monet Terrace, Winchester, VA 22602
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  /109

  $999,900

  • 5 Beds
  • 5.5 Baths
  • 5,670 Sq Ft

  530 Laurel Grove Rd, Winchester, VA 22602

  If you’re looking for a truly impressive property with unexpected benefits, welcome to 530 Laurel Grove Road. With nearly 6,000 finished square feet and five bedrooms and 5.5 baths, this home allows for easy gathering, relaxing, living, and entertaining—and includes a private in-law suite perfect for multi-generational living, guests, or rental potential. Ensconced in nature on 8.6 acres and

  Dan Whitacre Colony Realty

  530 Laurel Grove Rd, Winchester, VA 22602
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  /46

  $449,000

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  25 W Southwerk St, Winchester, VA 22601

  Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers the perfect balance of neighborhood tranquility and

  Dan Whitacre Colony Realty

  25 W Southwerk St, Winchester, VA 22601
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  /32

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  3138 Eton Place, Winchester, VA 22601

  Beautiful, just like brand new, 3 bedroom 2.5 bath end unit townhome located in The Lofts at Creekside! Walking distance to local restaurants and shopping here in Creekside. Home features large kitchen island, stainless steel appliances, and luxury vinyl plank flooring, private balcony, surrounded by open floor plan which provides for great entertainment. Nice upgrades all throughout the house!

  Christopher Hild Realty FC, LLC

  3138 Eton Place, Winchester, VA 22601
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  /36

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  102 Stribling Way, Winchester, VA 22602

  Beautifully maintained townhome located in the convenient Winchester community known as Freedom Manor. This location is close to everything yet out of the hurly-burly. Built in 2022 this home looks and feels brand new. Come inside! The entry level features a roomy foyer, a spacious finished room that is perfect for office, a one-car garage and an unfinished bathroom space with rough-in offering

  Angela Duncan MarketPlace REALTY

  102 Stribling Way, Winchester, VA 22602
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  /49

  $315,000

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft

  321 Copperfield Ln, Winchester, VA 22602

  Super cute 3 level townhome with a great design, two full baths one in the basement one in the upper level and a half on the main. Spacious and affordable!! 2 assigned parking spaces. Laminate flooring throughout. Spacious, light and bright!! Fenced backyard and deck. Freshly painted and NEW carpet, NEW stainless steel appliances!! Hurry to see today, it is vacant, quick closing possible!!

  Heather Mary Webb RE/MAX Allegiance

  321 Copperfield Ln, Winchester, VA 22602
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  /61

  $459,000 Open Sat 1PM - 3PM

  • 6 Beds
  • 3 Baths
  • 1,552 Sq Ft

  2250 Roosevelt Blvd, Winchester, VA 22601

  Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

  Heloisa Amar Samson Properties

  2250 Roosevelt Blvd, Winchester, VA 22601
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  /97

  $1,200,000

  • 6 Beds
  • 5 Baths
  • 6,682 Sq Ft

  217 W Boscawen St, Winchester, VA 22601

  Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and

  Gillian Greenfield Coldwell Banker Premier

  217 W Boscawen St, Winchester, VA 22601
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  /54

  $449,990

  • 3 Beds
  • 3.5 Baths
  • 2,239 Sq Ft

  142 Sequoia Dr, Winchester, VA 22602

  Some homes check the boxes. Others quietly stand apart the moment you pull up. This one does that. Not because it tries to impress, but because the setting, the layout, and the way the house sits on the land just make sense. Start with the lot. It’s a premium double-sized end-unit lot, something you simply don’t see often in townhouse communities. The home sits at the edge of the

  Alexander Bracke Real Broker, LLC

  142 Sequoia Dr, Winchester, VA 22602
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  /40

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,439 Sq Ft

  124 Lenore Ln, Winchester, VA 22602

  Welcome to 124 Lenore Lane, a beautifully appointed home in Winchester that blends modern upgrades, thoughtful design, and everyday comfort. This spacious residence offers a layout that works effortlessly for a wide range of lifestyles, with quality finishes throughout, all in a highly desirable community with outstanding amenities. The upper level features four generously sized bedrooms and two

  Sergio Vitela EXP Realty, LLC

  124 Lenore Ln, Winchester, VA 22602
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  /18

  $625,000

  • 5 Beds
  • 3.5 Baths
  • 2,967 Sq Ft

  219 Lehigh Dr, Winchester, VA 22602

  This nearly new Lennar home offers the advantages of modern construction combined with thoughtful upgrades and future expansion potential in a location that keeps you connected to everything Winchester has to offer. Built just two years ago, the home provides the confidence of newer systems and energy efficiency, enhanced by a complete security system and water softener for added comfort and

  Sarah Reynolds Keller Williams Realty

  219 Lehigh Dr, Winchester, VA 22602
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  /75

  $689,900

  • 4 Beds
  • 4.5 Baths
  • 5,020 Sq Ft

  108 Norfolk Ct, Winchester, VA 22602

  Welcome to 108 Norfolk Court in Winchester, where luxury, comfort, and an impressive amount of living space come together beautifully. Tucked away on a quiet cul-de-sac, this home offers both privacy and a peaceful setting while still being conveniently close to everything the area has to offer. With 5,020 finished square feet, this property provides the kind of space that makes everyday living

  Brian Yoder Realty ONE Group Old Towne

  108 Norfolk Ct, Winchester, VA 22602
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  /108

  $1,325,000

  • 5 Beds
  • 4.5 Baths
  • 4,100 Sq Ft

  100 Country Club Cir, Winchester, VA 22602

  This regal 1950s Colonial, named Eagle Gate, sits atop a knoll overlooking 6.34 pastoral acres on the east side of Winchester. This elegant home dazzles with nearly 4,000 finished square feet, three levels, five bedrooms, 4.5 baths, an expansive garage, a swimming pool, and renovations and updates that elevate the living experience to decadent. Majestic pillars are the hallmark of the handsome

  Dan Whitacre Colony Realty

  100 Country Club Cir, Winchester, VA 22602
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  /48

  $580,000 Open House 4/12

  • 4 Beds
  • 2.5 Baths
  • 3,414 Sq Ft

  3336 Hunting Ridge Rd, Winchester, VA 22603

  Colonial home 21 yrs young on 5 acres in Frederick county 4 bedroom 2 full baths with 1 half bath ., Whole house freshly painted in Jan/Feb 2025, laundry on main level with large pantry and large eat in kitchen with breakfast bar, granite countertops (new in Jan/Feb 2025) Family room formal dining room and living room (currently being used as a dining room) Large flat back yard with above ground

  Leslie Carter Carter Real Estate, Inc.

  3336 Hunting Ridge Rd, Winchester, VA 22603
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  /31

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,158 Sq Ft

  112 Grindstone Dr, Winchester, VA 22602

  Beautifully maintained 4-bedroom, 2.5-bath colonial home in the desirable Red Fox Run community. Built in 2002 and situated on a spacious 0.29-acre lot, this property offers the perfect blend of comfort, space, and offers tons of potential! The main level flows effortlessly, including both formal dining & living, with a bright eat-in style kitchen that opens to a large deck—ideal for

  Lisa Behr Hunt Country Sotheby's International Realty

  112 Grindstone Dr, Winchester, VA 22602
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  /45

  $500,000

  • 4 Beds
  • 3.5 Baths
  • 2,524 Sq Ft

  2643 Middle Rd, Winchester, VA 22601

  Location Location Location! NO HOA!!! Hardwood floors on the main level. Formal living and dining room leads to the Family room with stone fireplace, breakfast nook and kitchen. Step out on to the deck to enjoy the views. Large fenced level backyard. Large Primary suite with sitting room and luxury bath. Good sized bedrooms, one with an attached bath. Lower level leads to a patio and backyard.

  Lorraine Arora Berkshire Hathaway HomeServices PenFed Realty

  2643 Middle Rd, Winchester, VA 22601
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  /24

  $600,000

  • 5 Beds
  • 3.5 Baths
  • 3,494 Sq Ft

  127 Kinross Dr, Winchester, VA 22602

  A peaceful setting at the edge of Winchester pairs nicely with everyday convenience in this well-cared-for home at 127 Kinross Dr. Located in a quiet and welcoming neighborhood, this property offers the perfect balance of tranquility and practicality. The area provides a calm, residential atmosphere while still being just a short drive from Winchester's charming downtown area, where you'll find a

  Sarah Reynolds Keller Williams Realty

  127 Kinross Dr, Winchester, VA 22602
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  /51

  $309,000

  • 2 Beds
  • 3.5 Baths
  • 1,740 Sq Ft

  218 Tudor Dr, Winchester, VA 22603

  OPTIONAL THIRD BEDROOM! Welcome home to this beautifully updated townhome tucked away in a private, peaceful neighborhood—yet just minutes from major commuter routes, everyday amenities, and only 5 minutes to downtown Winchester! This bright and inviting home features fresh paint throughout, brand-new carpet, updated outlets, switches, lighting, and two new toilets—making it truly move-in ready.

  Stephanie Feltner Realty ONE Group Old Towne

  218 Tudor Dr, Winchester, VA 22603
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  /55

  $434,999

  • 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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  /80

  $795,000

  • 5 Beds
  • 4.5 Baths
  • 3,767 Sq Ft

  199 Meeting House Dr, Winchester, VA 22602

  Legendary Living on 3.46 Acres — 5BR Estate With Mountain Views, Luxe Updates & Iconic History Welcome to a truly one-of-a-kind estate offering over 3,700 sq. ft. of finished living space on nearly 3.46 acres, complete with mountain views, extensive updates, and a legendary past. This 5-bedroom, 4.5-bath home has been thoughtfully renovated throughout. The main level features a primary suite with

  Katie Deskins Century 21 Redwood Realty

  199 Meeting House Dr, Winchester, VA 22602
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  /67

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  707 E Cork St, Winchester, VA 22601

  Make an offer! 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,

  Misty Weaver Samson Properties

  707 E Cork St, Winchester, VA 22601
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  /17

  $435,000

  • 5 Beds
  • 4 Baths
  • 2,014 Sq Ft

  122 Cherry Hill Cir, Winchester, VA 22602

  Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

  Jen Moore ERA Oakcrest Realty, Inc.

  122 Cherry Hill Cir, Winchester, VA 22602
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  /79

  $860,000

  • 5 Beds
  • 5.5 Baths
  • 6,256 Sq Ft

  150 Ewell Dr, Winchester, VA 22602

  Price Reduction- Welcome to Equestrian Estates, a highly sought-after Winchester community with no HOA, where space, style, and flexibility come together beautifully. This stately 5-bedroom, 6-bath Colonial offers over 6,700 square feet of finished living space on nearly 3 private acres, creating the perfect setting for both everyday living and entertaining. Originally built in 2007 and

  Sherry Santmyer Hunt Country Sotheby's International Realty

  150 Ewell Dr, Winchester, VA 22602
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  /8

  $685,000

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft

  1950 Melvor Ln, Winchester, VA 22601

  Step into this meticulously maintained colonial home, a testament to quality craftsmanship and thoughtful design by Richmond American Homes. Situated in the desirable Meadow Branch South neighborhood, this residence offers an exceptional living experience with a perfect balance of formal and casual spaces This home is situated in a vibrant community with easy access to major roads, shopping, and

  Kim Kroner Washington Dulles Real Estate Group

  1950 Melvor Ln, Winchester, VA 22601
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  /47

  $985,000

  • 7 Beds
  • 5.5 Baths
  • 6,540 Sq Ft

  1020 Breckinridge Ln, Winchester, VA 22601

  This property exudes luxury multigenerational living in Meadowbranch! • Main level bedroom + bath• 6500 sq ft• Wet bar in primary suite• 3-car garage• No HOA• Backing to trees, and more..... Approximately 6,500 finished square feet of living space! A place to grow, gather, and stay awhile! A brick-paved, rocking chair-worthy, front porch sets the tone, and the charming side

  Sheila Pack RE/MAX Roots

  1020 Breckinridge Ln, Winchester, VA 22601
• 

  /2

  $539,000

  • 6 Beds
  • 3.5 Baths
  • 2,539 Sq Ft

  100 Alliance Ct, Winchester, VA 22602

  Come enjoy this beautiful 3-year young home. A spacious open floor plan is perfect for large families or entertaining friends and family. LVP flooring runs throughout the whole house except for a small area in the basement. The stunning kitchen features wrap around cabinets, a large center island and a separate pantry for all of your storage needs. There is also a flex space in the main level,

  Elizabeth Flood Keller Williams Realty

  100 Alliance Ct, Winchester, VA 22602
• 

  

  /13

  $429,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,094 Sq Ft

  104 Swansong Place, Winchester, VA 22603

  The three-level Skyline model masterfully combines a traditional exterior with a contemporary, open-concept floor plan. On the main level, you’ll find an expansive living room, bathed in natural light from numerous windows, flows effortlessly into the dining area and kitchen. The kitchen is designed with an L-shaped countertop and an island that borders the dining room. A cozy nook serves as a

  Brookfield Residential Builder

  104 Swansong Place, Winchester, VA 22603
• 

  

  /45

  $408,645 New Construction

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

  127 Lakota St, Winchester, VA 22602

  Don't miss this fantastic Adams interior 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

  D.R. Horton Builder

  127 Lakota St, Winchester, VA 22602
• 

  

  /34

  $420,340 New Construction

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

  1813 Harvest Dr, Winchester, VA 22601

  1813 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA – ready to 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, soft-close grey cabinets & drawers, and

  D.R. Horton Builder

  1813 Harvest Dr, Winchester, VA 22601

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