Winchester County VA Homes for Sale

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  $365,000

  • 4 Beds
  • 2.5 Baths
  • 2,678 Sq Ft

  719 National Ave, Winchester, VA 22601

  A true Federal‐style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many visions, this

  Windy Harris Hunt Country Sotheby's International Realty

  719 National Ave, Winchester, VA 22601
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  /40

  $399,900

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft

  225 Fox Dr, Winchester, VA 22601

  Welcome to 225 Fox Dr.! A very well maintained all brick ranch rambler. Has a fully updated kitchen with stainless steel appliances, quartz countertops, updated cabinetry with an induction oven. Very spacious open concept living room, good size bedrooms and hard flooring all around. The basement has plenty of potential and has recently been updated. The home offers paid off solar panels an EV

  Elber Olivo First Decision Realty LLC

  225 Fox Dr, Winchester, VA 22601
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  /51

  $480,000

  • 4 Beds
  • 2 Baths
  • 2,268 Sq Ft

  1306 Vanceright Cir, Winchester, VA 22601

  Filled with storybook charm and timeless character, this enchanting cottage-style home is much larger than it appears! Newly refinished hardwood floors flow throughout the home, blending warmth and elegance with everyday comfort. The updated kitchen offers modern convenience while maintaining the home's inviting charm. The partially finished basement provides flexible space for a family room,

  Julie Teets ERA Oakcrest Realty, Inc.

  1306 Vanceright Cir, Winchester, VA 22601
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  /31

  $560,000

  Open Wed 3PM - 6:30PM

  • 4 Beds
  • 3 Baths
  • 2,068 Sq Ft

  110 Russelcroft Rd, Winchester, VA 22601

  Nestled in the established Cedarmeade community, this beautifully updated 4-bedroom, 3-bath ranch home offers the perfect combination of comfort, style, and functionality. With over 2,000 square feet of finished living space, this home is designed to accommodate both everyday living and effortless entertaining. Step inside to find warm hardwood flooring, abundant natural light, and thoughtfully

  Grace Mooney Coldwell Banker Premier

  110 Russelcroft Rd, Winchester, VA 22601
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  /87

  $610,000

  Open Sat 11AM - 2PM

  • 3 Beds
  • 3.5 Baths
  • 3,140 Sq Ft

  1202 Handley Ave, Winchester, VA 22601

  Nestled on one of Winchester's most sought-after streets, this distinctive mid-century contemporary home offers a rare blend of character, space, and convenience just moments from downtown dining, shopping, and entertainment. Designed for comfortable main-level living, the home combines timeless architectural appeal with thoughtful functionality. The main level features a spacious primary suite

  Leah Marabella Realty ONE Group Old Towne

  1202 Handley Ave, Winchester, VA 22601
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  /83

  $559,900

  • 2 Beds
  • 2.5 Baths
  • 2,031 Sq Ft

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601

  Experience a rare opportunity to own a piece of Winchester history at The Fort, one of Old Town's most distinctive residential communities. Located just blocks from the vibrant Walking Mall, this beautifully renovated 2-bedroom, 2.5-bath condominium seamlessly blends historic character with modern luxury. Unit 105 features an open-concept floor plan with soaring ceilings, rich architectural

  Jen Richards MarketPlace REALTY

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601
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  /33

  $353,990

  New Construction

  • 3 Beds
  • 4 Baths
  • 1,669 Sq Ft

  136 Swansong Place, Winchester, VA 22603

  Brand New, townhome with 3 finished levels, is under construction and will be ready for you to call home this Summer! With builder incentives available, there is no reason to wait to make this the next place you call home!Backing to open space in the newest section of Snowden Bridge, this home will be in close proximity to all of the newest amenities. Natural light flows through the kitchen

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  136 Swansong Place, Winchester, VA 22603
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  /103

  $899,000

  Coming Soon

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

  466 Merrimans Ln, Winchester, VA 22601

  Your long search is over! Beautifully renovated all-brick ranch home situated on a secluded 2.03-acre lot in the city of Winchester, just a short walk to Valley Health. Offering an exceptional combination of privacy, convenience, and quality. This home features spacious living areas, three fireplaces, including one in the primary bedroom.The finished lower level provides outstanding

  John Schroth Colony Realty

  466 Merrimans Ln, Winchester, VA 22601
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  /36

  $360,000

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  302 Wentworth Dr, Winchester, VA 22601

  Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on

  Heloisa Amar Samson Properties

  302 Wentworth Dr, Winchester, VA 22601
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  /13

  $274,999

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft

  206 Kimberly Way, Winchester, VA 22601

  Beautifully remodeled 2-bedroom, 2.5-bath townhouse that's ready for you to move right in! This home features a stunning updated kitchen with granite countertops and stainless steel appliances, along with modern finishes throughout. Major improvements include a new roof and heat pump installed in 2023, providing added comfort and peace of mind. Spacious living areas, updated bathrooms, and

  

  Frank Armstrong, IV

  Colony Realty

  (540) 516-5187

  206 Kimberly Way, Winchester, VA 22601
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  /4

  $289,900

  Coming Soon

  • 2 Beds
  • 1 Bath
  • 1,458 Sq Ft

  102 N Purcell Ave, Winchester, VA 22601

  Charming home ideally located just minutes from the heart of historic Winchester! Whether you're looking for convenient access to shopping, dining, entertainment, or commuter routes, this home offers an exceptional location paired with valuable updates for peace of mind. Relax on the inviting covered front porch, the perfect place to enjoy your morning coffee or unwind at the end of the day. The

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 565-5107

  102 N Purcell Ave, Winchester, VA 22601
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  /49

  $320,000

  Coming Soon

  • 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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  /5

  $295,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 913 Sq Ft

  405 Shenandoah Ave, Winchester, VA 22601

  Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a

  Heloisa Amar Samson Properties

  405 Shenandoah Ave, Winchester, VA 22601
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  /40

  $429,000

  Coming Soon

  • Studio
  • 700 Sq Ft

  406-408 S Cameron St, Winchester, VA 22601

  Opportunity is knocking! This 3-unit multifamily property is centrally located in downtown Winchester, just minutes from the Walking Mall. The property is fully occupied and offers immediate rental income with strong upside potential. The property currently has a long term tenants with leases as follows: One month-to-month tenant , One tenant with a lease ending June 5, 2026 , One tenant with a

  Heloisa Amar Samson Properties

  406-408 S Cameron St, Winchester, VA 22601
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  /2

  $319,900

  Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,026 Sq Ft

  936 Allen Dr, Winchester, VA 22601

  Charming, beautifully maintained ranch home in a well-established Winchester neighborhood! Lovingly cared for by just one family since its construction, this special property even comes with the original architectural floor plans. This move-in-ready home features stunning, gleaming hardwood floors and an enclosed carport that has been seamlessly converted into a spacious family room. The main

  Jody Elson Dream Real Estate

  936 Allen Dr, Winchester, VA 22601
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  /2

  $337,000

  Coming Soon

  • 3 Beds
  • 4 Baths
  • 1,320 Sq Ft

  124 Worsham Terrace, Winchester, VA 22602

  Welcome to this beautifully maintained townhouse that offers the perfect blend of comfort, style, and convenience. Boasting an attractive full brick-front exterior with classic black shutters, this home offers timeless curb appeal and a welcoming first impression. The private driveway, attached one-car garage, and well-maintained landscaping add both functionality and charm. The main living level

  

  David Peña

  Corcoran McEnearney

  (540) 730-1775

  124 Worsham Terrace, Winchester, VA 22602
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  /2

  $449,900

  • 2 Beds
  • 2 Baths
  • 2,370 Sq Ft

  443 Fairmont Ave, Winchester, VA 22601

  So much potential !!! Great location, private yard, lots of square feet. Lot is 3/4 acre !Needs TLC. Listed $120,000 under tax assessment to allow room for updating. Kitchen has Corion counter tops , great cabinets. Very large room with beautiful book case built in, has fantastic screened in porch, Very large ( 24 X 24 ) family room with fireplace .

  Jeff Webber Long & Foster Real Estate, Inc.

  443 Fairmont Ave, Winchester, VA 22601
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  /7

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,737 Sq Ft

  614 Sherlock Trace, Winchester, VA 22601

  **Excellent Opportunity in the Heart of Winchester!** Don't miss the chance to own a well-located home in one of Winchester's most convenient areas. Situated on a quiet street, this property offers easy access to shopping, dining, schools, parks, and major commuter routes—everything that matters is just minutes away. Featuring **3 bedrooms** plus **two additional versatile rooms**, this home

  

  Carlos Soares

  Samson Properties

  (540) 517-6899

  614 Sherlock Trace, Winchester, VA 22601
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  /46

  $1,150,000

  • 5 Beds
  • 5 Baths
  • 5,695 Sq Ft

  801 Armistead St, Winchester, VA 22601

  There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been working so hard to create. Nestled in one of Winchester's most beloved neighborhoods, this stately residence blends timeless elegance with the confidence that comes from knowing the important work has already been done. Over the past

  Donna Chong Samson Properties

  801 Armistead St, Winchester, VA 22601
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  /27

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  601 Gray Ave, Winchester, VA 22601

  Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a

  

  Walther Vasquez Johnson

  Samson Properties

  (540) 701-0507

  601 Gray Ave, Winchester, VA 22601
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  /25

  $285,000

  $35K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  317 Fairview Ave, Winchester, VA 22601

  HUGE PRICE REDUCTION OF $35,000! Fully Renovated SFH in Historic Winchester! Prime location. Just minutes from charming Historic Downtown Winchester featuring local shops, restaurants, entertainment, and more! Beautifully Updated throughout. This charming home offers bright, inviting living spaces with modern finishes and thoughtfully updates designed for comfortable everyday living. w Just Move

  Donna Lutkins Real Broker, LLC

  317 Fairview Ave, Winchester, VA 22601
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  /26

  $364,990

  New Construction $3K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  11 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Lower Level Bathroom! This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free

  DRB Homes Builder

  11 Monteith Dr, Winchester, VA 22601
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  /26

  $369,990

  New Construction $5K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  13 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Deck! The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home with backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. This

  DRB Homes Builder

  13 Monteith Dr, Winchester, VA 22601
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  /24

  $359,990

  New Construction $5K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  12 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with 3 Bedrooms! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen

  DRB Homes Builder

  12 Monteith Dr, Winchester, VA 22601
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  /25

  $479,900

  • 3 Beds
  • 2 Baths
  • 2,025 Sq Ft

  654 Treys Dr, Winchester, VA 22601

  Welcome to 654 Treys Drive - Great corner lot in Williamsburg Heights! No HOA! One story home built in 1986 on crawl space with 3 bedrooms and 2 baths. Gas heat, and electric air conditioning. Beautiful wood floors. Great room with cathedral ceiling. Glassed in sunroom for cozy evenings. Spacious 2-car garage perfect for additional storage. Gas fireplace has not been used for 10 years. Sorry no

  Don Butler Virginia Property Group, Inc.

  654 Treys Dr, Winchester, VA 22601
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  /34

  $364,900

  • 4 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  621 Patterson Ave, Winchester, VA 22601

  Enchanting Cape Cod in an ideal in‐town location, this home has a welcoming ease to it, offering 3–4 bedrooms and 2.5 bathrooms with a layout that adapts beautifully to everyday living. The main level includes two convenient bedrooms, a comfortable, light‐filled living room, a separate dining area, and a renovated kitchen featuring new cabinets and stainless‐steel appliances. In 2021, the home

  LESLIE WEBB Long & Foster Real Estate, Inc.

  621 Patterson Ave, Winchester, VA 22601
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  /41

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  703 S Loudoun St, Winchester, VA 22601

  Located in the heart of Winchester’s Historic District, this remarkable property offers a rare opportunity to own a piece of the city’s rich architectural heritage just moments from vibrant Old Town Winchester. Blending timeless character with flexible living options, the home showcases classic historic charm paired with thoughtful updates that support today’s lifestyle. Inside the main

  John Ginty Samson Properties

  703 S Loudoun St, Winchester, VA 22601
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  /47

  $379,990

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 2,102 Sq Ft

  519 Fairmont Ave, Winchester, VA 22601

  Expect a long love affair with this home.Some homes feel like they were built with patience, pride, and a sense of permanence—and this historic Winchester beauty has that feeling the moment you step inside. Set near Old Town Winchester and positioned right next to the approved Cider Hill Neighborhood Design District, it offers something rare: preserved historic character today, with a

  Hannah Won Samson Properties

  519 Fairmont Ave, Winchester, VA 22601
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  /3

  $425,000

  • 4 Beds
  • 3 Baths
  • 2,157 Sq Ft

  1709 Brandon Dr, Winchester, VA 22601

  Spacious Home in a Prime Location! Discover the potential of this well-built Cape Cod offering generous living spaces and timeless charm. The welcoming living and dining area features a cozy fireplace, creating the perfect setting for gatherings and everyday living. The main level includes a desirable primary suite with a private full bath, an additional bedroom, and a hall bath for added

  Darcy Amburn Colony Realty

  1709 Brandon Dr, Winchester, VA 22601
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  /64

  $499,999

  $19K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,837 Sq Ft

  1317 Caroline St, Winchester, VA 22601

  Conveniently located in the heart of Winchester, this spacious brick ranch offers the perfect combination of timeless character, thoughtful updates, and flexible living space. Situated on a nearly half-acre corner lot, the property provides room to spread out while remaining just minutes from Winchester Medical Center, shopping, dining, and major commuter routes. Inside, you'll find beautiful

  Kristina Towns Weichert Realtors - Blue Ribbon

  1317 Caroline St, Winchester, VA 22601
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  /42

  $579,000

  • 4 Beds
  • 2.5 Baths
  • 2,108 Sq Ft

  2532 Middle Rd, Winchester, VA 22601

  Welcome to this stunning, custom-built Craftsman-style home that perfectly balances contemporary elegance with everyday functionality. Located in a prime, highly convenient Winchester location, this property immediately captivates with its striking curb appeal, highlighted by a large covered front porch and a classic architectural silhouette. Step inside to discover an immaculate interior bathed

  Dan Whitacre Colony Realty

  2532 Middle Rd, Winchester, VA 22601
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  /6

  $370,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1845 Rosser Ln, Winchester, VA 22601

  Beautifully maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+Community. The main-level features an open floor plan, vaulted ceiling, ceiling fan, gas fireplace, largeconcrete patio, and 1-car garage. 2026 updates include a new HVAC system. The primary suite offers awalk-in closet, private full bath, and laundry. Low maintenance living includes lawn and

  Derek Greene The Greene Realty Group

  1845 Rosser Ln, Winchester, VA 22601
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  /46

  $320,000

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  2917 First St, Winchester, VA 22601

  Welcome home to this charming stone rancher, perfectly situated on a fantastic lot adorned with gorgeous, mature trees and a lush, expansive yard. Step inside to find a spacious living room bathed in natural light, featuring rich hardwood flooring and a cozy stone fireplace that serves as the room's centerpiece. The effortless layout flows seamlessly into the kitchen and formal dining room,

  Dan Whitacre Colony Realty

  2917 First St, Winchester, VA 22601
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  /32

  $429,000

  • 2 Beds
  • 2 Baths
  • 1,031 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 Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural

  Janet Flaherty Keller Williams Realty

  118 1/2 E Cork St, Winchester, VA 22601
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  /29

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,734 Sq Ft

  11 W Germain St, Winchester, VA 22601

  Back on the Market!...Beautifully located in the heart of Historic Winchester, this charming home offers 2 bedrooms, 1 full bath, and a versatile bonus room on the second floor-perfect for an office, guest space, or hobby room. Enjoy the convenience of being within walking distance to downtown Winchester's shops, restaurants, entertainment, and the famous Apple Blossom Festival festivities.

  Magnolia Halkowitz ERA Oakcrest Realty, Inc.

  11 W Germain St, Winchester, VA 22601
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  /46

  $359,999

  • 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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  /23

  $350,000

  $25K PRICE DROP

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

  317 N Kent St, Winchester, VA 22601

  Step into a world of timeless elegance and modern luxury with this stunning Colonial residence, beautifully renovated in 2015 while preserving its historic charm. Nestled in a serene setting, this detached home offers a perfect blend of classic architecture and contemporary comforts, making it an ideal retreat for those seeking an exclusive lifestyle. As you enter, you are greeted by rich

  

  Clark Smith

  Samson Properties

  (540) 530-4200

  317 N Kent St, Winchester, VA 22601
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  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  540 Bellview Ave, Winchester, VA 22601

  Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow for indoor-outdoor

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
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  /48

  $525,000

  $20K PRICE DROP

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

  938 Wayne Dr, Winchester, VA 22601

  Improved Price!! 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

  Kira Grubb Realty ONE Group Old Towne

  938 Wayne Dr, Winchester, VA 22601
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  /34

  $369,900

  • 2 Beds
  • 2 Baths
  • 1,219 Sq Ft

  1856 Melvor Ln, Winchester, VA 22601

  Welcome to 1856 Melvor Lane in Winchester! Nestled on a corner lot in a desirable 55+ community, this charming one-level cottage offers the perfect blend of comfort, convenience, and low-maintenance living. Featuring 2 bedrooms, 2 full baths, and an airy open floor plan with cathedral ceilings, the home is designed for both everyday living and easy entertaining. Recent improvements include luxury

  Natasha Roberts Realty ONE Group Old Towne

  1856 Melvor Ln, Winchester, VA 22601

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