Colonial Homes for Sale in Winchester, VA

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  /58

  $549,900

  • 4 Beds
  • 2.5 Baths
  • 2,234 Sq Ft

  1917 Harvest Dr, Winchester, VA 22601

  Beautiful Colonial set in a quiet neighborhood with convenient access to town and I-81. The main level features gleaming hardwood floors and classic oak plantation shutters, creating a warm and inviting feel throughout. Enjoy a formal living room with built-in shelving and a formal dining room accented by a chair rail, perfect for gatherings and entertaining. The kitchen offers granite

  

  Brock Harris

  Samson Properties

  (540) 712-8133

  1917 Harvest Dr, Winchester, VA 22601
• Explore Winchester

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  /2

  $250,000 Coming Soon

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

  523 Monticello St, Winchester, VA 22601

  Sold "As-IS" Nice investment or starter property. Needs a little updating. Hardwoods throughout upstairs and living room downstairs. This price includes 525 Monticello lot. Tax ID #330-02-19. If any questions call listing agent. Agent related to seller.

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 305-3611

  523 Monticello St, Winchester, VA 22601
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  /51

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 3,945 Sq Ft

  270 Sotheby Ct, Winchester, VA 22602

  This all-brick custom home sits on 8 acres on the east side of Winchester, offering a prime commuter location with a gated entrance for added privacy. The main level includes a high-end kitchen with a gas cooktop, double wall ovens, and a large pantry, alongside a family room with a fireplace and wet bar. An additional room on this level serves as an optional living room or office, while covered

  

  Paul Gallagher

  Colony Realty

  (540) 551-7922

  270 Sotheby Ct, Winchester, VA 22602
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  /40

  $640,000 Open Sat 12PM - 2PM

  • 6 Beds
  • 3.5 Baths
  • 3,192 Sq Ft

  162 Omps Dr, Winchester, VA 22601

  This exceptional residence is nestled in a popular neighborhood in Winchester, just moments from Winchester Medical Center. With almost 4,000 square feet of refined living space, this 6-bedroom, 3.5-bath home delivers the scale, comfort, and location today’s discerning buyer expects.Designed for both elegant entertaining and everyday ease, the home features expansive living areas filled with

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 274-1014

  162 Omps Dr, Winchester, VA 22601
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  /50

  $1,200,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,284 Sq Ft

  80 Gough Rd, Winchester, VA 22602

  Dreaming of your own farmette, private estate, or peaceful country retreat?This is a rare opportunity to create what you're searching for on a premium 8-acre lot offering gorgeous mountain views, usable acreage, and a truly scenic setting. The elevated homesite sits approximately 800 feet off Cedar Creek Grade with frontage on Gough Road, providing privacy while still offering easy access to

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 781-0968

  80 Gough Rd, Winchester, VA 22602
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  /41

  $669,900

  • 5 Beds
  • 3.5 Baths
  • 3,083 Sq Ft

  216 Lehigh Dr, Winchester, VA 22602

  Skip the wait for new construction—this stunning 2023-built Discovery II Colonial in Winchester’s Senseny Village offers luxury, space, and upgrades galore! Featuring 4 bedrooms, 3.5 baths, and 3,083 sq ft across the upper two levels, it sits on a premium lot with wooded views and includes a large unfinished walkout basement with full-size windows and bathroom rough-in—ideal for future

  Donna Wolford Redfin Corporation

  216 Lehigh Dr, Winchester, VA 22602
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  /31

  $454,900 Open Sun 1PM - 3PM

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

  1025 S Loudoun St, Winchester, VA 22601

  Prepare to be wowed by this stunning renovation in downtown Winchester! This charming Colonial has been fully remodeled and is ready for new owners. No detail was spared—original features were thoughtfully preserved to maintain the home’s historic charm, while modern conveniences were added throughout for everyday living. The original hardwood floors were refinished and run throughout the house,

  Heloisa Amar Samson Properties

  1025 S Loudoun St, Winchester, VA 22601
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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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  /37

  $430,000

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

  17 E Leicester St, Winchester, VA 22601

  LOWER INTEREST RATE FOR YOU.....Sellers are offering you 2 percent of sales price so you can buy down your interest rate with an initial 2/1 interest rate buydown OR use the 2% seller concession for your closing costs on this classic brick “American Foursquare” house in Winchester’s historic district. This very well maintained 1928 home was designed and built by “ole time” craftsmen who had an

  Roger Lamborne MarketPlace REALTY

  17 E Leicester St, Winchester, VA 22601
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  /48

  $615,000

  • 5 Beds
  • 3.5 Baths
  • 4,500 Sq Ft

  211 Lynnehaven Dr, Winchester, VA 22602

  Professional Photos Coming Soon! Spacious 5BR 3.5BA Colonial on .33 acre fenced yard. Finished lower level for added comfort. Features Kitchen with island; formal dining area, formal living room, office/den. Spacious primary bedroom with large walk in closet. Across from Greenwood Mill Elem School; great commuter location. . Must See to Appreciate!

  Toni Carone Long & Foster Real Estate, Inc.

  211 Lynnehaven Dr, Winchester, VA 22602
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  /25

  $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. The neighborhood feel is quiet and comfortable, with easy in-and-out access that helps keep daily routines running smoothly, even during peak times. Shopping, dining, and community favorites in Winchester are close by, and nearby commuter routes make it simple to stay connected. Set on

  Sarah Reynolds Keller Williams Realty

  127 Kinross Dr, Winchester, VA 22602
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  /63

  $365,000 New Construction

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

  508 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

  508 Grouse Dr, Winchester, VA 22602
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  /56

  $439,000 Open Sat 11AM - 1PM

  • 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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  /45

  $450,000

  • 4 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  100 Winns Cir, Winchester, VA 22602

  Welcome home to Winns Circle! This is a fantastic opportunity for future homeowners to live in a bright, spacious home on the east side of Winchester, as the home is listed under the tax assessed value, as well as the most recently appraised value of $487,700 (completed 1/21/2026 and available to qualified buyers upon request) and the After Repair Value of $522, 700, as noted on the appraisal.

  Nicole Lewis Coldwell Banker Premier

  100 Winns Cir, Winchester, VA 22602
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  /45

  $449,000 Coming Soon

  • 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

  $384,900

  • 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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  /65

  $637,500 Open Sat 10AM - 12PM

  • 4 Beds
  • 2.5 Baths
  • 2,908 Sq Ft

  101 Winslow Ct, Winchester, VA 22602

  Tucked on the cul-de-sac's corner lot in Raven Wing, 101 Winslow Court, offers the kind of space, flexibility, and personality that makes a house feel like home. The main level is especially versatile, with room to fit the way you actually live — whether you need one or even two dedicated office spaces, a cozy coffee or bar area, open entertaining space for hosting, or simply the everyday room to

  Sarah Abderrazzaq Realty ONE Group Old Towne

  101 Winslow Ct, Winchester, VA 22602
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  /98

  $669,000

  • 6 Beds
  • 4.5 Baths
  • 4,124 Sq Ft

  461 Skylar Lanes Way, Winchester, VA 22603

  Welcome to 461 Skylar Lanes Way, a stunning home nestled on over 2 acres in the upscale & sought after Walnut Springs Estates community, with just minutes from downtown Winchester! This spacious residence offers 6 bedrooms, 4.5 bathrooms, finished basement and a 3-car side load garage with a circular paved driveway, providing plenty of room for family, guests, and entertaining. Step inside the

  Michele Gibson Samson Properties

  461 Skylar Lanes Way, Winchester, VA 22603
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  /43

  $414,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,251 Sq Ft

  713 Ross St, Winchester, VA 22601

  COMPLETED AND READY TO MOVE IN!!!BRAND NEW 3 BEDROOM, 2.5 BATH COLONIAL! NO HOA FEES AND NO SUBDIVISION RULES!Be the first to call this beautiful new construction yours. Conveniently located just outside the City of Winchester and close to shopping, this home offers an open layout designed for entertaining. The great room leads into the spacious kitchen featuring an oversized island,

  Donna Anderson Samson Properties

  713 Ross St, Winchester, VA 22601
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  $459,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 2,805 Sq Ft

  407 Jefferson St, Winchester, VA 22601

  READY FOR BUYER! TURN KEY classic colonial, fully UPDATED, and WALKABLE to downtown! *3 LEVELS totalling 2568 SF* Stroll to the restaurants in Old Town, enjoy the activities at Handley, or walk to the trails at MSV! NEW roof, HVAC, privacy fencing, custom paint and built-in cabinetry, plus new stainless steel appliances, including washer/dryer. Get creative in the FINISHED LOWER LEVEL with

  Gillian Greenfield Coldwell Banker Premier

  407 Jefferson St, Winchester, VA 22601
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  /25

  $340,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  718 Panther Dr, Winchester, VA 22602

  Brand-new construction in the Wilde Acres community of Frederick County, now with the seller offering a $5,000 CREDIT toward buyer closing costs with acceptable terms. This 3-bedroom, 2.5-bath Colonial-style home is planned to offer approximately 1,512 finished square feet across three levels and sits on a spacious 0.25-acre lot. Designed for modern living, the main level features an open-concept

  Abby Walters Preslee Real Estate

  718 Panther Dr, Winchester, VA 22602
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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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  /47

  $279,000

  • 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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  /5

  $349,900 New Construction

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

  Lot 33 Falcon Trail, Winchester, VA 22602

  New Construction on 1/3 Acre – No Carpet!This affordable 2-bed, 2.5-bath home offers high-end finishes and incredible growth potential.Premium Finishes: Hardwood floors throughout (including all bedrooms), tile in all baths, and granite kitchen countertops.Open Layout: Bright family room and a spacious kitchen/dining area perfect for entertaining.Owner’s Suite: Large master

  Jim Thomson Realty ONE Group Old Towne

  Lot 33 Falcon Trail, Winchester, VA 22602
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  /28

  $429,000 Open Sun 12PM - 2PM

  • 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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  /44

  $499,000

  • 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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  /21

  $410,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  215 Cochise Trail, Winchester, VA 22602

  Under Construction - stainless steel appliances are included- April Delivery -10 minutes from town - New Custom Colonial with upgrades and designed for modern living! This beautiful home offers 3 bedrooms, 2.5 baths, including a spacious primary suite with a private ensuite bath. The open-concept main level seamlessly connects the kitchen, dining, and living areas—perfect for everyday living and

  RoxAnn Grimes RE/MAX Roots

  215 Cochise Trail, Winchester, VA 22602
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  /32

  $399,000 Coming Soon

  • 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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  /64

  $375,000 Open Fri 11AM - 2PM

  • 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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  /61

  $530,000 Open Sun 1PM - 3PM

  • 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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  /56

  $1,850,000

  • Studio
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  In town location for this completely remodeled multi unit property. This property contains 4 homes and 2 apartments that have been completely refinished. . Update, main house is now rented and income is over $15,000 per month. This property is also improved with large block garage and a separate 4 car garage with over 18' ceilings. Perfect for the automotive enthusiast or you can continue to

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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  /24

  $399,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  211 Inca Trail, Winchester, VA 22602

  3-10-26 Foundation going in this week. Premium Finishes: Enjoy a builder-upgraded interior featuring gleaming hardwood floors throughout the entire home (including all bedrooms) and elegant tile in all bathrooms.Gourmet Kitchen: Equipped with upgraded cabinetry, sleek granite countertops, a central island, and a sunny breakfast nook.Modern Layout: An airy, open floor plan connects the

  Jim Thomson Realty ONE Group Old Towne

  211 Inca Trail, Winchester, VA 22602
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  /62

  $675,000 Coming Soon

  • 5 Beds
  • 4.5 Baths
  • 4,301 Sq Ft

  105 Barnston Ct, Winchester, VA 22602

  This is the kind of home where memories are made. Pool parties in the summer, cozy evenings by the fireplace in the winter, and plenty of space for everyone in between — all tucked away on a peaceful cul-de-sac in one of Winchester’s most desirable neighborhoods. Imagine summer afternoons spent poolside in the saltwater in-ground pool, evenings hosting friends on the patio, and the comfort of

  Katrina Smith Samson Properties

  105 Barnston Ct, Winchester, VA 22602
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  /24

  $399,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  2 Tonto Trail, Winchester, VA 22602

  New Construction: 100% Hardwood – No Carpet!Move into this pristine 3-bed, 2.5-bath Colonial featuring high-end finishes and a seamless layout. The chef-inspired kitchen offers granite tops and a breakfast island, while the massive owner’s retreat provides total relaxation with its soaking tub and double walk-ins. Expand your living space in the walk-out basement (ready for a future bath) or

  Jim Thomson Realty ONE Group Old Towne

  2 Tonto Trail, Winchester, VA 22602
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  /82

  $370,000

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  2431 Cedar Creek Grade, Winchester, VA 22602

  This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in place.

  Edward Beightol Cedar Creek Real Estate

  2431 Cedar Creek Grade, Winchester, VA 22602
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  /40

  $414,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,251 Sq Ft

  709 Ross St, Winchester, VA 22601

  COMPLETED AND READY TO MOVE IN!!!BRAND NEW 3 BEDROOM, 2.5 BATH COLONIAL! NO HOA FEES AND NO SUBDIVISION RULES!Be the first to call this beautiful new construction yours. Conveniently located just outside the City of Winchester and close to shopping, this home offers an open layout designed for entertaining. The great room leads into the spacious kitchen featuring an oversized island,

  Donna Anderson Samson Properties

  709 Ross St, Winchester, VA 22601
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  /10

  $699,999 New Construction

  • 5 Beds
  • 4 Baths
  • 3,850 Sq Ft

  111 Pawn Ct, Winchester, VA 22602

  Move in Spring 2026 ! Final opportunity in this community! Welcome to the stunning Preston floorplan! This spacious 2-story home with a partially finished basement offers 5 bedrooms and 4 full bathrooms. The main level features a cozy dining room, a bedroom with a full bathroom, an electric fireplace, and a gourmet kitchen—perfect for entertaining. Enjoy outdoor living on the composite deck. The

  Jay Day LPT Realty, LLC

  111 Pawn Ct, 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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  /2

  $699,000 Coming Soon

  • 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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