Colonial Homes for Sale in Winchester, VA

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  /90

  $949,000

  $40K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,621 Sq Ft

  144 Widener Dr, Winchester, VA 22603

  Exceptional All-Brick Custom Home with Panoramic Mountain Views!Nestled on a private 2-acre cul-de-sac lot in prestigious Butler Estates, this exceptional all-brick 4-bedroom, 4.5-bath custom home offers over three finished levels, timeless craftsmanship, and breathtaking Appalachian Mountain and pastoral views. A brand-new roof adds even more peace of mind.The main level features

  Laura White ERA Oakcrest Realty, Inc.

  144 Widener Dr, Winchester, VA 22603
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  /53

  $549,000

  $26K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,368 Sq Ft

  440 Canyon Rd, Winchester, VA 22602

  Welcome home to this stunning 5-bedroom, 3-bath, 3-story Colonial located in the highly desirableSovereign Village community on the east side of Winchester. Offering space, comfort, and thoughtfulupdates throughout, this home is designed to fit every stage of life.Step inside to find beautiful hardwood floors and a warm, inviting living room featuring a gas fireplace just off the

  Tami Woerl ERA Oakcrest Realty, Inc.

  440 Canyon Rd, Winchester, VA 22602
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  /33

  $379,999

  $35K PRICE DROP

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

  123 Etnam St, Winchester, VA 22602

  Well-maintained colonial available in one of Winchester’s premier subdivisions, Pembridge Heights. The main level features a formal dining room just off the foyer, perfect for family gatherings, which flows into the eat-in kitchen with LVP flooring, stainless steel appliances, a tile backsplash, custom wood cabinetry, and access to the deck overlooking a semi-flat backyard with a koi pond. The

  Paul Sneeringer Samson Properties

  123 Etnam St, Winchester, VA 22602
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  /36

  $316,900

  $8K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,692 Sq Ft

  315 Copperfield Ln, Winchester, VA 22602

  *PRICE ADJUSTMENT *Welcome to this beautifully remodeled end-unit townhouse offering three spacious levels of comfortable living. The main level features a refreshed kitchen with brand-new cabinets, new flooring, and recessed lighting, creating a bright and inviting space for everyday living and entertaining.Upstairs, you’ll find two generously sized rooms, each with its own full

  JORGE CABRERA Spring Hill Real Estate, LLC.

  315 Copperfield Ln, Winchester, VA 22602
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  /32

  $495,000

  $35K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,505 Sq Ft

  108 Morgan St, Winchester, VA 22601

  OPEN HOUSE 08/30/2026 FROM 1:00 PM - 3:00 PMWelcome to this charming historic home in Old Town Winchester. This spacious 3-bedroom Colonial blends timeless character with modern comfort in a convenient downtown location. Thoughtfully updated with today’s buyer in mind, this inviting residence offers upgraded amenities while preserving its classic appeal.Ideally situated within

  Stacey Rowe Real Broker LLC

  108 Morgan St, Winchester, VA 22601
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  /34

  $552,000

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

  100 Winns Cir, Winchester, VA 22602

  Beautifully remodeled Colonial in Pioneer Heights. Designed with primary suite; ideal home office configuration. All large bedrooms, large hardwood living room with stone wood fireplace, new natural gas upstairs furnace and a/c, upgraded insulation in attic, oversized garage and large deck. New paint, LVPk flooring in baths and kitchen. Must see.

  Thomas Hennerty NetRealtyNow.com, LLC

  100 Winns Cir, Winchester, VA 22602
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  /66

  $359,000

  Open Sun 12PM - 2PM

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

  812 Appleseed Ct, Winchester, VA 22601

  Nestled on a quiet cul-de-sac surrounded by mature trees in the highly desirable Orchard Hills Subdivision with no HOA fees or restrictions, this traditional all-brick home features 3 bedrooms, 1.5 bathrooms, a 2-car driveway, and three beautifully finished levels of move-in-ready living space. From the tree-lined sidewalks and charming street lighting, you are welcomed onto a main level boasting

  Feletia Sharples Realty FC, LLC

  812 Appleseed Ct, Winchester, VA 22601
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  /49

  $320,000

  • 4 Beds
  • 2 Baths
  • 2,034 Sq Ft

  410 S Cameron St, Winchester, VA 22601

  Step into a home where timeless character and modern opportunity come together. This spacious property is filled with antique charm and unique details throughout.Featuring 4 bedrooms, 2 full bathrooms, and several versatile flex spaces, this home can easily adapt to your needs or offer increased income potential with a renovation. Enjoy the outdoor living opportunities with a private

  Heloisa Amar Samson Properties

  410 S Cameron St, Winchester, VA 22601
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  /58

  $674,900

  • 4 Beds
  • 3.5 Baths
  • 3,924 Sq Ft

  146 Darby Dr, Winchester, VA 22602

  Beautiful brick-front home in sought-after Ravenwing offering three finished levels and exceptional space throughout! This 4-bedroom, 3.5-bath home features a welcoming main level with formal living and dining rooms, plus a cozy family room with a gas fireplace—perfect for relaxing or entertaining.Dual staircases lead to the expansive upper level, highlighted by two owner’s suites, each with

  Traci Shoberg Samson Properties

  146 Darby Dr, Winchester, VA 22602
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  /70

  $525,000

  • 4 Beds
  • 3.5 Baths
  • 3,829 Sq Ft

  114 Nassau Dr, Winchester, VA 22602

  Offering three luxuriously finished levels, extensive upgrades, and a backyard designed for entertaining, this 4 bed/3.5 bath colonial is a MUST-SEE! Step inside to a grand foyer with soaring 12-foot ceilings and walls of windows flooding the home with natural light throughout. The main level features a dedicated study room accented by striking arched windows, spacious living and dining areas, an

  Angela Kim RE/MAX Galaxy

  114 Nassau Dr, Winchester, VA 22602
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  /37

  $710,000

  • 5 Beds
  • 3.5 Baths
  • 3,946 Sq Ft

  110 Bentpath Ct, Winchester, VA 22602

  Welcome to 110 Betpath Ct, nestled within the premier Twin Lakes Overlook (TLO) enclave of exclusively single-family homes by Toll Brothers and Richmond American, this exceptional 2019-built executive estate offers an unmatched lifestyle in Winchester. Spanning nearly 4,000 square feet of refined living space, this property combines high-end craftsmanship with an extraordinary, functional

  Xinli Ji Realty Aspire

  110 Bentpath Ct, Winchester, VA 22602
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  /56

  $380,000

  • 4 Beds
  • 2.5 Baths
  • 2,243 Sq Ft

  900 Enfield Dr, Winchester, VA 22602

  Nestled in the serene Wilde Acres community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Built in 2007 and thoughtfully renovated in 2019, this home boasts a pristine condition and modern amenities that cater to the discerning homeowner. Step inside to discover an inviting open floor plan that seamlessly

  Alexandra Brown Spring Hill Real Estate, LLC.

  900 Enfield Dr, Winchester, VA 22602
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  /4

  $290,000

  • 2 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  323 Copperfield Ln, Winchester, VA 22602

  Nestled in the charming Copperfield neighborhood, this delightful townhouse offers a perfect blend of comfort and convenience. Built in 2002, this well-maintained home features 2 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and everyday living. With 1,868 square feet of thoughtfully designed interiors, you'll find a cozy atmosphere that invites you to unwind. The

  Rebecca Sims Century 21 Redwood Realty

  323 Copperfield Ln, Winchester, VA 22602
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  /95

  $699,900

  $24K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,264 Sq Ft

  342 Canyon Rd, Winchester, VA 22602

  Welcome to 342 Canyon Rd, a spacious and beautifully maintained home in the desirable Twin Lakes Overlook community on Winchester's east side close to Rt 7. Situated on a beautifully landscaped corner lot of nearly .40 acres where the schoolbus stop is at the front door, this impressive home offers over 4,264 finished square feet with a thoughtfully designed floor plan perfect for both everyday

  Michele Gibson Samson Properties

  342 Canyon Rd, Winchester, VA 22602
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  /46

  $370,000

  New Construction Coming Soon Oct 5

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

  902 Panther Dr, Winchester, VA 22602

  With special financing options available, Discover the promise of your future home. This stunning Colonial-style residence all most completed. Move in your new home in just 30 days or less. This property offers a perfect blend of modern design and classic comfort. With three spacious bedrooms and two and a half bathrooms, this home is designed for both relaxation and entertaining. The interior

  Steve DuBrueler Coldwell Banker Premier

  902 Panther Dr, Winchester, VA 22602
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  /42

  $449,000

  • 4 Beds
  • 1.5 Baths
  • 1,932 Sq Ft

  420 W Cork St, Winchester, VA 22601

  Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a

  Dan Whitacre Colony Realty

  420 W Cork St, Winchester, VA 22601
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  /43

  $499,000

  $26K PRICE DROP

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

  144 Morning Glory Dr, Winchester, VA 22602

  Nestled in the charming Apple Ridge community, this stunning Colonial-style home offers a perfect blend of comfort and elegance. Set on a generous 0.4-acre lot, the property backs onto serene open common areas and lush trees, providing a tranquil retreat right in your backyard. Enjoy the luxury of multiple balconies, a spacious deck, and a welcoming porch, ideal for relaxing or entertaining while

  James Powell RE/MAX Supercenter

  144 Morning Glory Dr, Winchester, VA 22602
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  /63

  $824,900

  $64K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 4,891 Sq Ft

  161 Skylar Lanes Way, Winchester, VA 22603

  PRICED BELOW RECENT Gorgeous Country Home on Two Acres — Nearly 5,000 Sq Ft of Well-Appointed Living!! Welcome to 161 Skylar Lanes Way, a thoughtfully-updated and well-maintained six-bedroom, five-bath home just 20 minutes from downtown Winchester. This inviting property features modern updates and practical design throughout - see the attached list of recent upgrades! Bright and airy, the

  Kristin Crosby Samson Properties

  161 Skylar Lanes Way, Winchester, VA 22603
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  /46

  $329,000

  $31K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  307 1/2 E Piccadilly St, Winchester, VA 22601

  Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll

  Nate Crandell HoneyWay

  307 1/2 E Piccadilly St, Winchester, VA 22601
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  /17

  $344,000

  $5K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 1,740 Sq Ft

  108 Monticello Square, Winchester, VA 22602

  Great Commuter Location in Brookland Manor!! 3 level townhome features 3 bedrooms, 2 full baths, 2 half baths, one car garage, master suite with full bath (shower and soaking tub) and walk-in closet, family room on lower level, large living room and kitchen on main level. 50-year shingles installed in 2022, new air handler in 2025. Seller is listing both for sale or lease.

  Don Butler Virginia Property Group, Inc.

  108 Monticello Square, Winchester, VA 22602
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  /51

  $349,000

  Open Sat 11AM - 1PM $30K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,592 Sq Ft

  2055 Cidermill Ln, Winchester, VA 22601

  PRICE IMPROVEMENT. Welcome home to this beautifully maintained 3-bedroom, 2-full-bath/2 half bath, end-of-row townhouse! Perfectly situated in a highly desirable, family-friendly neighborhood, step inside to find gleaming hardwood floors and large, sunlit rooms that offer plenty of space to live and entertain. The heart of the home features a spacious kitchen that flows seamlessly onto a private

  Karen O'Hare Colony Realty

  2055 Cidermill Ln, Winchester, VA 22601
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  /28

  $301,000

  Open Sun 11AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 920 Sq Ft

  711 Fawn Dr, Winchester, VA 22602

  Nestled in the charming Wilde Acres subdivision, this delightful Colonial-style home offers a perfect blend of comfort and modern living. Built in 2024, this detached residence features 2 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and privacy. The inviting living area is enhanced by a cozy fireplace, perfect for creating warm memories on chilly evenings. Step

  Steve DuBrueler Coldwell Banker Premier

  711 Fawn Dr, Winchester, VA 22602
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  /76

  $1,650,000

  • 4 Beds
  • 5 Baths
  • 6,183 Sq Ft

  582 Miller Rd, Winchester, VA 22602

  Built in 1774, before America was America, this remarkable 31-acre estate has stood through the birth of a nation, and today it's ready for its next chapter. This is history you can live in, a piece of the past, built for the life you're living now. Hardwood floors run throughout, and the spacious kitchen opens effortlessly into the family room and dining space, the kind of layout that makes

  Elizabeth Cossette ERA Oakcrest Realty, Inc.

  582 Miller Rd, Winchester, VA 22602
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  /69

  $665,000

  $34K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,738 Sq Ft

  158 Old Forest Cir, Winchester, VA 22602

  NEW PRICE — NOW $665,000! An exceptional opportunity to make 158 Old Forest your new home. With a $10,000 price improvement, this property offers even more value. If you've been waiting to take a second look, now is the time! SELLER OFFERING ONE-YEAR STONEBROOK CLUB MEMBERSHIP! Offering approximately 4,000 square feet of living space, welcome to 158 Old Forest Circle, a spacious and inviting

  Mrs. Maria M Cunningham EXP Realty, LLC

  158 Old Forest Cir, Winchester, VA 22602
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  /59

  $600,000

  • 3 Beds
  • 1.5 Baths
  • 3,483 Sq Ft

  1311 Handley Ave, Winchester, VA 22601

  Nestled in the charming City of Winchester, this delightful Colonial home, built in 1952, exudes warmth and character. With its classic brick exterior and excellent condition, this residence invites you to experience a blend of traditional elegance and modern comfort. Step inside to discover a thoughtfully designed interior featuring beautiful hardwood floors that flow seamlessly throughout. The

  Kim Hurst MarketPlace REALTY

  1311 Handley Ave, Winchester, VA 22601
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  /26

  $749,900

  $16K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,220 Sq Ft

  175 Shields Dr, Winchester, VA 22602

  Beautiful 5 bedroom, 2.5-bath brick-front home situated on 2 private acres, offering the perfect blend of space, comfort, and recent updates. Shower on the main floor in laudry room, bonus room being used as a main floor bedroom. Major updates provide peace of mind, including a new roof (2025), HVAC systems replaced in 2023, 2024, and 2025, a new pressure tank, water heater, sump pump, Culligan

  Sheila Pack RE/MAX Roots

  175 Shields Dr, Winchester, VA 22602
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  /73

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,768 Sq Ft

  394 Old Baltimore Rd, Winchester, VA 22603

  Coming Soon! A truly special property in a gorgeous, peaceful setting! This charming 1911 farmhouse sits on 2.75 acres and offers the perfect opportunity for a small farmette, complete with a barn and large detached garage. Thoughtfully updated throughout the years while maintaining its farmhouse character, the home offers plenty of space and a rare, flexible layout with two primary suites - one

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  394 Old Baltimore Rd, Winchester, VA 22603
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  /60

  $650,000

  Open Sat 2PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,528 Sq Ft

  132 Darby Dr, Winchester, VA 22602

  Welcome to this beautiful single-family home in the sought-after Ravenwing neighborhood of Winchester, Virginia. Conveniently located near local shopping, downtown Winchester, Costco, I-81, Route 50, and Route 7, this spacious two-story property offers over 3,500 square feet of comfortable living space tailored for modern living. The main level features a large kitchen complete with an island,

  Paige Ulevich Dream Real Estate

  132 Darby Dr, Winchester, VA 22602
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  /59

  $474,900

  New Construction $60K PRICE DROP

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

  619 Farmington Blvd, Winchester, VA 22602

  NEW PRICE + LIMITED-TIME BUYER INCENTIVE! Now offered at $474,900, plus the builder is offering up to $10,000 toward purchaser closing costs OR the cost of installing a fence—purchaser's choice! This special incentive is available with an acceptable contract ratified by 10/15/26—a great opportunity to save upfront or put the finishing touch on your new home.This move-in-ready home

  Marisa Varley ERA Oakcrest Realty, Inc.

  619 Farmington Blvd, Winchester, VA 22602

Showing Results 81 - 109, Page 3 of 3