Winchester County VA Homes for Sale

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  /64

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 2,180 Sq Ft

  706 S Cameron St, Winchester, VA 22601

  Claim your spot in the heart of the city with this authentic 1866 gem, perfectly positioned to enjoy everything downtown Winchester has to offer. Proudly displaying its Winchester Historic Building plaque, this home is just steps from the vibrant local dining scene, boutique shopping, parks, and schools. It’s a rare find that pairs 19th-century soul with modern reliability, featuring the coveted

  Dan Whitacre Colony Realty

  706 S Cameron St, Winchester, VA 22601
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  /17

  $329,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  2952 Grace St, Winchester, VA 22601

  Charming one level, 3-bedroom, 1 full bath home conveniently located in the heart of Winchester. Recently remodeled with new flooring throughout, updated bathroom, and modern fixtures. Thoughtful updates make this home move-in ready and ideal for easy, single-level living. Close to shopping, dining, and commuter routes.

  Carolina Mosquera Weichert, REALTORS

  2952 Grace St, Winchester, VA 22601
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  /70

  $749,500

  • 6 Beds
  • 4 Baths
  • 4,672 Sq Ft

  817 Chelsea Dr, Winchester, VA 22601

  Spacious 5-6-bedroom, 4-bath brick-front rancher with a fully finished basement, offering flexible living space for today’s needs. The main level features a welcoming living room with a tray ceiling & a gas fireplace, a formal dining room with crown molding & chair rail, and a well-appointed kitchen with Corian countertops and a walk-in pantry. The primary suite is conveniently located on the

  Sheila Pack RE/MAX Roots

  817 Chelsea Dr, Winchester, VA 22601
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  /26

  $419,990 New Construction

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

  126 Swansong Place, Winchester, VA 22603

  Exceptional value for a 4‐bedroom END‐UNIT townhome—almost ready for summer move‐in! Brand‐new construction offers modern style and comfort with oak stairs with upgraded railings and durable LVP flooring throughout the main level. Backing to open space in the newest section of Snowden Bridge, this spacious home includes a flexible entry‐level bedroom with full bath, a bright open‐concept main

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  126 Swansong Place, Winchester, VA 22603
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  /50

  $1,179,000 Coming Soon

  • 4 Beds
  • 5 Baths
  • 3,456 Sq Ft

  1004 Heth Place, Winchester, VA 22601

  A Stunning Brick Colonial residence graced by meticulously manicured gardens and lush vegetation, cocooning the property in a tranquil and private ambiance. Offering an array of amenities, each of its three immaculately finished floors mirrors the care bestowed upon the surrounding gardens. Generously proportioned rooms bathed in natural light enhance the spacious open plan living areas,

  Kathryn Hallett Long & Foster Real Estate, Inc.

  1004 Heth Place, Winchester, VA 22601
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  /2

  $429,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,419 Sq Ft

  118 1/2 E Cork St, Winchester, VA 22601

  Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Winchester’s historic downtown walking mall, offering easy access to restaurants, bars, boutiques, and entertainment. Originally built in the 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural charm, and

  Janet Flaherty Keller Williams Realty

  118 1/2 E Cork St, Winchester, VA 22601
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  /2

  $359,999 Coming Soon

  • 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 everything while still offering the privacy and feel of a standalone home. Inside, you’ll find a

  Mr. Nate Crandell HoneyWay

  307 1/2 E Piccadilly St, Winchester, VA 22601
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  /55

  $310,500 Open Sat 1PM - 3PM

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

  406 Highland Ave, Winchester, VA 22601

  OPEN HOUSE SATURDAY MAY 9th 1 - 3 PM!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

  Lisette Turner Century 21 Redwood Realty

  406 Highland Ave, Winchester, VA 22601
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  /50

  $389,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,809 Sq Ft

  328 Longview Ave, Winchester, VA 22601

  This ranch home in Winchester City has been meticulously maintained. Beautiful hardwood floors. Dining room can be converted back to a third bedroom, simply install doors that are being stored in the basement. Basement is 75% finished and offers endless possibilities. The remaining 25% provides room for ample storage and/or a workshop. New HVAC installed in 2019, new water heater (2025) has never

  Kelly Bauer Coldwell Banker Premier

  328 Longview Ave, Winchester, VA 22601
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  /26

  $400,000

  • 5 Beds
  • 2 Baths
  • 1,011 Sq Ft

  605 Dunlap St, Winchester, VA 22601

  Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-bathroom home offers both seclusion and incredible proximity to Winchester's finest amenities, schools, shopping, and major commuter routes. This residence has been completely reimagined, blending the enduring strength, high-end modern finishes. The moment you enter, you are greeted by the seamless flow of

  Alexandra Brown Spring Hill Real Estate, LLC.

  605 Dunlap 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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  /36

  $320,000

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. Great investment opportunity! Currently tenant-occupied, offering

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /39

  $421,000

  • 3 Beds
  • 2.5 Baths
  • 2,277 Sq Ft

  422 S Loudoun St, Winchester, VA 22601

  Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level

  Dana Cloud Realty ONE Group Old Towne

  422 S Loudoun St, Winchester, VA 22601
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  /30

  $375,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 1,916 Sq Ft

  317 N Kent St, Winchester, VA 22601

  An amazing totally renovated 1820 home in the heart of downtown/historic district!! This home features: 4bedrooms, 3 full baths, remodeled gourmet kitchen, refinished hardwood floors, barn style doors, deluxeprimary bath, and so much more.

  Clark Smith Samson Properties

  317 N Kent St, Winchester, VA 22601
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  /13

  $257,500

  • 3 Beds
  • 1 Bath
  • 1,404 Sq Ft

  332 Opequon Ave, Winchester, VA 22601

  Adorable ranch home with great potential - TLC needed. The home has a large family room for entertainment, a rear patio for outside relaxation, and a fully fenced yard. Laminate flooring throughout the home with carpet in the family room. Selling as-is. Inspections for informational purposes only. The home is located downtown within close proximity to shopping, restaurants, Jim Barnett Park, and

  Renee Waymire Samson Properties

  332 Opequon Ave, Winchester, VA 22601
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  /40

  $349,000

  • 4 Beds
  • 2 Baths
  • 1,996 Sq Ft

  802 E Cork St, Winchester, VA 22601

  Check out the Virtual Tour! Rich with character and steeped in history, this spacious vintage home sits proudly on a corner lot, offering timeless appeal with many original features still intact. From the moment you enter, you’ll appreciate the craftsmanship of a bygone era—complete with built-in bookshelves, a charming upper-level sleeping porch, and a traditional canning storage area in the

  Jennifer Egen Samson Properties

  802 E Cork St, Winchester, VA 22601
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  /101

  $915,000 Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 4,330 Sq Ft

  512 S Loudoun St, Winchester, VA 22601

  Distinctive home on the historic register, Winchester walking tour, this property has been featured on the Winchester homes tour ---Walk two blocks into the heart of Winchester; restaurants, festivals, shopping! Gorgeous inside and out. Fully renovated, 4 levels with a log cabin room (in the blue building) likely built with timber from Fort Loudoun) , rgourmet emodeled kitchen with gas cooking,

  Roxanne Watts Coldwell Banker Realty

  512 S Loudoun St, Winchester, VA 22601
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  /47

  $369,900

  • 3 Beds
  • 1.5 Baths
  • 1,366 Sq Ft

  517 Dunlap St, Winchester, VA 22601

  Welcome to 517 Dunlap St — a beautifully renovated 3-bedroom, 1.5-bath home set on a nicely sized, fully fenced lot in the heart of Winchester, where modern updates meet everyday comfort and a backyard designed for making the most of every season, complete with your own private pool.The main level welcomes you with a bright and inviting layout, where the living and dining spaces flow

  Carolyn Young Samson Properties

  517 Dunlap St, Winchester, VA 22601
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  /65

  $549,900

  • 3 Beds
  • 2.5 Baths
  • 3,083 Sq Ft

  3013 Saratoga Dr, Winchester, VA 22601

  Nestled in the prestigious Battle Park Estates, this exquisite residence embodies the perfect blend of luxury and comfort. Built in 2001, this detached home showcases a timeless design with high-end finishes that create an inviting atmosphere throughout. Step inside to discover a spacious open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for both entertaining

  Michelle Donovan Long & Foster Real Estate, Inc.

  3013 Saratoga Dr, Winchester, VA 22601
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  /44

  $425,000

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  823 Woodland Ave, Winchester, VA 22601

  Charming on the outside, modern on the inside Located in a charming, very quiet neighborhood, this home offers the perfect blend of timeless character and a fully modern renovation. Featuring 3 beautifully updated levels, the home showcases new Bruce hardwood flooring throughout with no transitions, creating a seamless, elegant flow and easy mobility. Every detail has been thoughtfully upgraded

  Lenora Zaccur Coldwell Banker Realty

  823 Woodland Ave, Winchester, VA 22601
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  /29

  $465,000

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

  310 Longview Ave, Winchester, VA 22601

  THIS IS A MUST SEE! Wonderful location, 3 years new property, located in short drive to everything, Winchester. This is an offering you don't want to miss out on. Its not often that a nearly new construction home with all the best of everything comes on the market. For starters theres No HOA .All the appliances and operating systems are still under warranty and the interior is in blank canvas new

  Dave Milburn Coldwell Banker Realty

  310 Longview Ave, Winchester, VA 22601
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  /22

  $364,990 Open Sat 12PM - 4PM

  • 3 Beds
  • 4 Baths
  • 2,000 Sq Ft

  117 Boone Ct, Winchester, VA 22602

  Immediate Move-In Available at Rossum Crossing! Discover the convenience of townhome living in our vibrant community, ideally situated close to shopping and dining. The St. Paul Townhome offers three bedrooms, two and a half baths, and a private one-car garage. The main level features an open-concept layout, highlighted by a spacious family room that seamlessly connects to a modern kitchen. Enjoy

  Holly Horne Poole New Home Star Virginia, LLC

  117 Boone Ct, Winchester, VA 22602
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  /5

  $349,900 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,451 Sq Ft

  420 E Pall Mall St, Winchester, VA 22601

  "Beautifully Renovated On Pall Mall St." This 2-bedroom, 2-full bath ranch style home is ready for you to move right in! Home has been completely painted on the inside, and the outside brick/concrete, side handrails, outside/inside of doors have been freshly painted. The kitchen has new granite counters, new sink & faucet, new LVP flooring and new stainless-steel appliances. Huge family room with

  Matt Kilmer Samson Properties

  420 E Pall Mall St, Winchester, VA 22601
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  /9

  $150,000

  • Land
  • 18,295 Sq Ft
  • $357,143 per Acre

  1322 Vanceright Cir, Winchester, VA 22601

  Tucked away on a quiet cul-de-sac, this 0.4174-acre lot offers a fantastic opportunity to build your dream home in a highly desirable Winchester location. Enjoy the convenience of being just minutes from Handley High School and the charm, dining, and shopping of downtown Winchester. The property features a 30' easement, allowing for access while still providing ample space for your vision. With

  John Scully Colony Realty

  1322 Vanceright Cir, Winchester, VA 22601
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  /3

  $519,900 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,879 Sq Ft

  315 Walker St, Winchester, VA 22601

  Beautiful brick split-foyer home tucked away on a quiet dead-end street in the desirable Whittier Acres community. This location is one of Winchester’s best kept secrets! 315 Walker St has nearly 2,900 finished square feet, combining space, flexibility, and a peaceful setting just minutes from Old Town Winchester, Winchester Medical Center, and everyday conveniences. The main level features a

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 698-3569

  315 Walker St, Winchester, VA 22601
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  /62

  $799,000

  • 5 Beds
  • 4.5 Baths
  • 4,438 Sq Ft

  769 Seldon Dr, Winchester, VA 22601

  Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along

  Amanda Slate Keller Williams Realty

  769 Seldon Dr, Winchester, VA 22601
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  /20

  $364,990 New Construction

  • 3 Beds
  • 4 Baths
  • 2,000 Sq Ft

  105 Boone Ct, Winchester, VA 22602

  Brand New & Move-In Ready in Rossum Crossing!Located close to shopping and dining — convenience at its best! The St. Paul Townhome offers up to 2,000 sq ft with: 3 Bedrooms 2 Full Baths + 2 Half Baths 1-Car Garage Open-concept main level with a spacious family room flowing into a modern kitchen featuring: Large island Breakfast nook Pantry Composite deck – perfect for relaxing or entertaining

  Jimmy Thomas New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
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  /35

  $409,990 New Construction

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

  1805 Harvest Dr, Winchester, VA 22601

  1805 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for April 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, white cabinets, and stainless-steel appliances. The

  D.R. Horton Builder

  1805 Harvest Dr, Winchester, VA 22601
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  /67

  $569,900

  • 3 Beds
  • 2.5 Baths
  • 2,450 Sq Ft

  1930 Harvest Dr, Winchester, VA 22601

  Experience the perfect blend of traditional charm and modern scale in this meticulously maintained residence located in the highly sought-after and established community of Meadow Branch South. The striking exterior, framed by a beautifully manicured lawn and mature landscaping, welcomes you into a soaring two-story foyer anchored by gleaming hardwood floors. The main level is designed for

  Dan Whitacre Colony Realty

  1930 Harvest Dr, Winchester, VA 22601
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  /2

  $549,900 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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  /31

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  608 Dunlap St, Winchester, VA 22601

  Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort.

  Richard Butcher Coldwell Banker Premier

  608 Dunlap St, Winchester, VA 22601
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  /22

  $625,000

  • 5 Beds
  • 2 Baths
  • 1,948 Sq Ft

  446 N Loudoun St, Winchester, VA 22601

  Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking

  Lawrence Lessin Homes By Owner, Inc.

  446 N Loudoun St, Winchester, VA 22601
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  /29

  $324,900

  • 3 Beds
  • 4 Baths
  • 1,336 Sq Ft

  120 Worsham Terrace, Winchester, VA 22602

  This beautifully maintained 3 level townhome is a great place to call home. Perfectly situated at the back of the subdivision, you get the benefits of the community while enjoying the quiet surroundings. Enjoy the toddler playground and the walking/running trail just steps from your door. This home is also the perfect commuter location less than a mile from Route 7 and Interstate 81. Only minutes

  Marielle Thoburn Keller Williams Realty

  120 Worsham Terrace, Winchester, VA 22602
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  /14

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  2910 Sorrell Ct, Winchester, VA 22601

  Welcome to 2910 Sorrell Court—a well-maintained home offering comfort, convenience, and thoughtful updates in a desirable location. This property features a functional layout, with durable luxury vinyl plank flooring throughout the main living areas and hardwood flooring in the family room and hallways.The kitchen was renovated just two years ago and offers updated finishes. The home has been

  Marisa Varley ERA Oakcrest Realty, Inc.

  2910 Sorrell Ct, Winchester, VA 22601
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  /32

  $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
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  /57

  $630,000 Open Fri 5:30PM - 7:30PM

  • 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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  /86

  $1,200,000

  • 3 Beds
  • 3.5 Baths
  • 3,497 Sq Ft

  466 Merrimans Ln, Winchester, VA 22601

  An extraordinary and rarely available offering within the city limits, 466 Merrimans Lane presents a stately brick residence set on an impressive 2.03 acre lot—an uncommon blend of privacy, space, and convenience in an in-town setting. This classic home features three generously sized bedrooms and three-and-a-half baths, with a traditional floor plan designed for both comfortable everyday living

  Laura White ERA Oakcrest Realty, Inc.

  466 Merrimans Ln, Winchester, VA 22601
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  /28

  $329,000

  • 2 Beds
  • 1 Bath
  • 1,132 Sq Ft

  419 Stone Meadow Ct, Winchester, VA 22601

  Tucked away on a quiet cul-de-sac in the desirable Stonecrest Village community, 419 Stone Meadow Court offers a perfect blend of comfort, style, and convenience. Built in 1997 and thoughtfully maintained by its single in-residence owner, this charming home features easy one-level living with a spacious, light-filled layout ideal for both everyday living and entertaining. Recent updates include

  Alice Shank Samson Properties

  419 Stone Meadow Ct, Winchester, VA 22601
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  /52

  $549,000

  • 4 Beds
  • 3.5 Baths
  • 2,989 Sq Ft

  1300 Caroline St, Winchester, VA 22601

  Welcome to 1300 Caroline Street—where timeless design meets everyday functionality in one of Winchester’s most convenient locations. Perfectly positioned on a spacious 0.31-acre corner lot, this beautifully maintained residence offers 4 bedrooms, 3.5 bathrooms, a finished basement, and a desirable 2-car side-load garage. The main level showcases a thoughtfully renovated kitchen featuring updated

  Lisa Behr Hunt Country Sotheby's International Realty

  1300 Caroline St, Winchester, VA 22601
• 

  

  /65

  $599,900

  • 6 Beds
  • 4 Baths
  • 3,511 Sq Ft

  1400 Valley Ave, Winchester, VA 22601

  Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful original hardwood floors, tall ceilings, fireplace, 4 season sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you

  Danielle Spriggs Samson Properties

  1400 Valley Ave, Winchester, VA 22601

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