Colonial Homes for Sale in Winchester, VA

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  $449,000

  • 4 Beds
  • 4.5 Baths
  • 1,913 Sq Ft

  315 National Ave, Winchester, VA 22601

  Fully reimagined for modern living while preserving its timeless charm, this stunning 1910 home in the heart of Downtown Winchester offers the perfect blend of character, luxury, and value. Completely renovated from top to bottom, every detail has been thoughtfully updated—delivering the feel of new construction within a classic architectural setting.This spacious residence features 4

  

  Carlos Soares

  Samson Properties

  (540) 787-2197

  315 National Ave, Winchester, VA 22601
• Explore Winchester

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  /65

  $389,990 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  317 Gray Ave, Winchester, VA 22601

  Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully

  

  Matthew Abregu

  Keller Williams Realty

  (540) 701-3590

  317 Gray Ave, Winchester, VA 22601
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  $220,000

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  523 Monticello St, Winchester, VA 22601

  Nice duplex. Needs a little updating. Hardwood floors in living room and throughout the 2nd level. Property at this price doesn't include the lot that is being used as part of the yard now. Property can be bought with the lot for $240k Tax id number 330-02-19.Agent related to seller.

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 660-7920

  523 Monticello St, Winchester, VA 22601
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  $650,000 Open Sat 2PM - 5PM

  • 4 Beds
  • 4 Baths
  • 3,266 Sq Ft

  293 Skylar Lanes Way, Winchester, VA 22603

  3 FINISHED LEVELS * 3 CAR OVERSIZED SIDELOAD GARAGE * 2 PRIVATE ACRES * LOCATED IN SOUGHT AFTER WALNUT SPRINGS ESTATES * WRAP AROUND FRONT PORCH * MAIN LEVEL FEATURES INVITING 2 STORY FOYER * LIVING ROOM AND DINING ROOM WITH TRAY CEILING AND CUSTOM MOLDINGS * KITCHEN WITH GE PROFILE BLACK STAINLESS APPLIANCES WITH GAS COOKING AND CENTER ISLAND * BREAKFAST ROOM WITH BAYWINDOW * FAMILY ROOM WITH

  Gregory Frank Berkshire Hathaway HomeServices PenFed Realty

  293 Skylar Lanes Way, Winchester, VA 22603
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  $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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  /57

  $645,000 Open Sun 4PM - 6PM

  • 4 Beds
  • 3.5 Baths
  • 4,188 Sq Ft

  930 Wayne Dr, Winchester, VA 22601

  Beautiful brick-front Colonial in a prime location! Nestled in a quiet neighborhood yet just minutes from I-81 and local amenities, this stunning home offers the perfect blend of convenience and tranquility.Brand new LVP flooring was just installed on both levels. Step into the grand two-story foyer, flanked by a formal living room and dining room accented with elegant columns and a cozy

  Elizabeth Flood Keller Williams Realty

  930 Wayne Dr, Winchester, VA 22601
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  $545,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,317 Sq Ft

  938 Wayne Dr, Winchester, VA 22601

  Welcome to this spacious and well-maintained home in the desirable Meadow Branch South community. Offering over 3,300 square feet, this 4-bedroom, 2.5-bath home provides the perfect blend of space, comfort, and thoughtful updates. The main level features an updated kitchen, ideal for both everyday living and entertaining, along with multiple living areas that offer flexibility for today’s

  Kira Grubb Realty ONE Group Old Towne

  938 Wayne Dr, Winchester, VA 22601
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  $530,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,971 Sq Ft

  251 Rossmann Blvd, Winchester, VA 22602

  The home is vacant, move-in ready, with preselected upgrades and a one-year home warranty. Welcome tothis beautifully crafted new home by a respected local builder, offering almost 2,000 square feet ofthoughtfully designed living space in the desirable Sovereign Village community with room to grow in theunfinished basement. The inviting, open-concept main level features a spacious

  Marisa Varley ERA Oakcrest Realty, Inc.

  251 Rossmann Blvd, Winchester, VA 22602
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  /2

  $514,900 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 3,152 Sq Ft

  407 Tamarack Cir, Winchester, VA 22602

  Beautiful colonial located on a quiet cul-de-sac. The formal living and dining rooms feature hardwood floors, crown molding, and chair rail. The light-filled, spacious kitchen offers an island and an eat-in area, perfect for everyday living and entertaining. A half bath completes the main level.Upstairs, enjoy a relaxing primary suite with a walk-in closet and attached bath with dual sinks,

  Heloisa Amar Samson Properties

  407 Tamarack Cir, Winchester, VA 22602
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  $499,900

  • 5 Beds
  • 4 Baths
  • 2,288 Sq Ft

  144 Morning Glory Dr, Winchester, VA 22602

  Motivated Seller! Extraordinary 5-Bedroom Home with Pool and Dual Kitchens in Winchester This exceptional 5-bedroom, 3.5-bathroom home — complete with a private office — offers comfort, functionality, and modern elegance. Thoughtfully designed for both everyday living and relaxed entertaining, this residence features two fully renovated kitchens (one on the main level and one in the walkout

  Julieta Russell Keller Williams Realty Dulles

  144 Morning Glory Dr, Winchester, VA 22602
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  $674,900

  • 3 Beds
  • 2 Baths
  • 3,024 Sq Ft

  777 Glengary Rd, Winchester, VA 22603

  If you’ve been dreaming of wide open space, mountain views, and a home with character, this special property may be exactly what you’ve been waiting for.Nestled on 37 unrestricted acres, this beautiful property offers the best of Shenandoah Valley living. With a perfect blend of open pasture and wooded privacy, the land provides room to breathe, explore, and imagine what’s possible. A

  Sharon Farinholt Realty ONE Group Old Towne

  777 Glengary Rd, Winchester, VA 22603
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  $520,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,023 Sq Ft

  102 Brockham Ct, Winchester, VA 22602

  The home is ready, and includes pre-selected upgrades and a new-construction warranty. Welcome to this beautifully crafted new home by a respected local builder, offering over 2,000 square feetof thoughtfully designed living space in the desirable Sovereign Village community. The inviting, open-concept main level features a spacious kitchen with a large island, perfect for gathering and

  Marisa Varley ERA Oakcrest Realty, Inc.

  102 Brockham Ct, Winchester, VA 22602
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  /40

  $540,000

  • 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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  $679,900

  • 3 Beds
  • 2.5 Baths
  • 1,856 Sq Ft

  5039 Wardensville Grade, Winchester, VA 22602

  Need space for you and yours PLUS more than enough garage space? Look no further! Nestled on nearly 5.5 private acres, this spacious and meticulously maintained 1- owner residence offers the perfect blend of rural serenity and modern convenience. Set well back from the road and framed by towering, mature trees, the property boasts a stunning backdrop of the rolling Blue Ridge Mountains in the

  Dan Whitacre Colony Realty

  5039 Wardensville Grade, Winchester, VA 22602
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  $535,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  253 Rossmann Blvd, Winchester, VA 22602

  The home is vacant, move-in ready, and includes pre-selected upgrades and a new-construction warranty. Welcome to this beautifully crafted new home by a respected local builder, offering almost 2,300 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting, open-concept main level features a spacious kitchen with a large island, perfect for

  Marisa Varley ERA Oakcrest Realty, Inc.

  253 Rossmann Blvd, Winchester, VA 22602
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  $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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  $535,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  100 Brockham Ct, Winchester, VA 22602

  This move-in-ready home includes pre-selected upgrades and a new-construction warranty. Welcome to this beautifully crafted new home by a respected local builder, offering almost 2,300 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting, open-concept main level features a spacious kitchen with a large island, perfect for gathering and

  Marisa Varley ERA Oakcrest Realty, Inc.

  100 Brockham Ct, Winchester, VA 22602
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  /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
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  /59

  $535,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,023 Sq Ft

  619 Farmington Blvd, Winchester, VA 22602

  The home is vacant, move-in ready, and includes pre-selected upgrades and a new-construction warranty. Welcome to this beautifully crafted new home by a respected local builder, offering over 2,000 square feetof thoughtfully designed living space in the desirable Sovereign Village community. The inviting open-concept main level features a spacious kitchen with a large island, perfect for

  Marisa Varley ERA Oakcrest Realty, Inc.

  619 Farmington Blvd, Winchester, VA 22602
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  $360,000

  • 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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  $420,000

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  17 E Leicester St, Winchester, VA 22601

  The perfect old town Winchester location and ready for you to move in......Classic brick “American Foursquare” house in Winchester’s historic district. . This well maintained 1928 home was designed and built by “ole time” craftsmen who had an appreciation for solid, quality construction. What better way to spend wonderful lazy evenings or morning coffee than on the expansive 23-foot long front

  Roger Lamborne MarketPlace REALTY

  17 E Leicester St, Winchester, VA 22601
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  /2

  $465,000

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  310 Longview Ave, Winchester, VA 22601

  Dave Milburn Coldwell Banker Realty

  310 Longview Ave, Winchester, VA 22601
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  $424,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  743 Berryville Ave, Winchester, VA 22601

  Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot.The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to

  Sineenat Sirimas Pearson Smith Realty, LLC

  743 Berryville Ave, Winchester, VA 22601
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  $465,000

  • 3 Beds
  • 2.5 Baths
  • 1,745 Sq Ft

  430 Babbs Mountain Rd, Winchester, VA 22603

  3-bedroom, 2.5-bath home set on 2.68 wooded acres just minutes from Winchester Medical Center, offering a private, peaceful setting with everyday convenience. Enjoy the outdoors from the covered front porch or rear deck—perfect for relaxing or entertaining. Inside, the spacious kitchen features a center island, stainless steel appliances, and luxury vinyl plank flooring, opening to a comfortable

  Sheila Pack RE/MAX Roots

  430 Babbs Mountain Rd, Winchester, VA 22603
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  /7

  $239,900

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  139 Little River Dr, Winchester, VA 22602

  Rebecca Sims Century 21 Redwood Realty

  139 Little River Dr, Winchester, VA 22602
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  $435,000

  • 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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  /21

  $379,900

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
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  /97

  $1,150,000

  • 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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  $310,500 Open House 5/10

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft

  406 Highland Ave, Winchester, VA 22601

  LOcated in The Old Town Winchester area but on a quiet street, we are happy to list this nicely remodeled 2 level home. Since the purchase of this center hall Circa 1930s home, the owners have totally resurfaced and painted the metal roof, installed windows,installed all new plumbing and electrical services, a dual zoned HVAC system, sanded the gleaming hardwood floors, installed new vanities,new

  Lisette Turner Century 21 Redwood Realty

  406 Highland Ave, Winchester, VA 22601
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  /2

  $475,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,330 Sq Ft

  237 Asbury Rd, Winchester, VA 22602

  Welcome to 237 Asbury Road in Winchester tucked away on a quiet cul-de-sac yet perfectly located just off Rt. 7 for an easy commute. This 4-bedroom, 2.5-bath home offers a spacious, functional layout with multiple living areas, including a living room, separate dining room, and a family room with fireplace. The custom kitchen features granite countertops, a center island with prep sink, and ample

  Stacey Mullins ERA Oakcrest Realty, Inc.

  237 Asbury Rd, Winchester, VA 22602
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  /2

  $334,900 Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 1,754 Sq Ft

  112 Chatham Square, Winchester, VA 22601

  Beautiful townhome in Huntington Meadows. This 3 bedroom, 2.5 bath home has full washer and dryer, amazing fenced backyard, and finished basement with full bath. Minutes from Rt 7 and I-81 makes for easy commuting. New stainless steel kitchen appliances, remodeled second floor bath, and a brand new deck not pictured. Must see in person.

  Mr. Nate Crandell HoneyWay

  112 Chatham Square, Winchester, VA 22601
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  $399,000

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft

  13 E Leicester St, Winchester, VA 22601

  Incredible location, incredible home! Relax on the elevated front porch overlooking Leicester St, or retreat to the private back yard. Inside, gleaming wood floors and original trim compliment the new kitchen and bathrooms. HVAC, wiring, plumbing, windows, roofing, and siding have been lovingly replaced/updated in the last 5 years. This home is walkable to everything, and sits on a calm side

  William Steinmetz RE/MAX Roots

  13 E Leicester St, Winchester, VA 22601
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  $265,000

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  106 W Southwerk St, Winchester, VA 22601

  This charming 3-bedroom, 1.5-bath Colonial is perfectly located just minutes from Old Town Winchester and steps from Handley High School, giving you easy access to local restaurants, shops, and community events. Enjoy slow mornings on the covered front porch with your coffee, or gather with friends and family on the spacious back deck. Inside, you’ll find warm, comfortable living spaces filled

  Laura White ERA Oakcrest Realty, Inc.

  106 W Southwerk St, Winchester, VA 22601
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  /19

  $349,900 New Construction

  • 2 Beds
  • 2.5 Baths
  • 1,152 Sq Ft

  212 Falcon Trail, Winchester, VA 22602

  4-14-26 Going to paint and hardwoods down. Delivery end of April. Current Shawneeland Inventory208 Beaver Trail210 Beaver Trail212 Falcon Trail211 Inca Trail103 Tonto Trail123 Killbuck Trail116 Pinto Trail1/3 Acre – No Carpet!This affordable 2-bed, 2.5-bath home offers high-end finishes and incredible growth potential.Premium Finishes: Hardwood floors

  Jim Thomson Realty ONE Group Old Towne

  212 Falcon Trail, Winchester, VA 22602
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  $409,000

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
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  $424,900

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  1025 S Loudoun St, Winchester, VA 22601

  TONS OF UPGRADES! This home has been updated top to bottom. From the roof, windows, kitchen, bathrooms, light fixtures, HVAC, and so on. Located just 1 block from Handley High School, this home and all of its high end improvements make it a treasure waiting to be discovered. As you walk through this home you'll notice that a ton of care and thoughtfulness was put into what it is today. The

  Michael Sprague Samson Properties

  1025 S Loudoun St, Winchester, VA 22601
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  $465,000

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft

  3137 Eton Place, Winchester, VA 22601

  Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for

  Laura White ERA Oakcrest Realty, Inc.

  3137 Eton Place, Winchester, VA 22601
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  /10

  $273,000

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2967 Sorrell Ct, Winchester, VA 22601

  This diamond in the rough has solid bones and plenty of potential for the right buyer. The HVAC system is only two years old, the water heater is brand new, and both full bathrooms have already been updated. The home could use some fresh paint, and the dishwasher is currently not working, but the major systems are in great shape—making this an excellent opportunity for a starter home or

  Jamie Cook Treck Realty LLC

  2967 Sorrell Ct, Winchester, VA 22601
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  /32

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,842 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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  /64

  $374,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  506 Grouse Dr, Winchester, VA 22602

  Nestled in the charming Wilde Acres community, this stunning new construction home, completed in 2025,offers a perfect blend of modern design and traditional comfort. The Colonial architectural style, adorned with durable vinyl siding, invites you into a warm and welcoming space. Step inside to discover a thoughtfully designed interior featuring a traditional floor plan that seamlessly connects

  Steve DuBrueler Coldwell Banker Premier

  506 Grouse Dr, Winchester, VA 22602

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