Winchester County VA Homes for Sale

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  /69

  $650,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 4,179 Sq Ft

  1529 Dalton Place, Winchester, VA 22601

  Welcome to 1529 Dalton Place, an exceptional home tucked away on a quiet cul-de-sac in one of Winchester's most desirable locations. Offering 4 spacious bedrooms, 3.5 bathrooms, and an expansive floor plan, this beautifully designed residence delivers the perfect blend of comfort, style, and functionality. From the moment you enter, you'll appreciate the generous room sizes throughout, including

  RoxAnn Grimes RE/MAX Roots

  1529 Dalton Place, Winchester, VA 22601
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  /64

  $375,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,474 Sq Ft

  805 Pennsylvania Ave, Winchester, VA 22601

  Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect

  Sherry Santmyer Hunt Country Sotheby's International Realty

  805 Pennsylvania Ave, Winchester, VA 22601
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  /2

  $500,900

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  609 Quartzite Cir, Winchester, VA 22601

  Welcome to 609 Quartzite Circle! A beautifully maintained 4-bedroom, 3-bath home offering a spacious and functional layout designed for modern living. The main level features inviting living spaces, hardwood flooring, and an open kitchen with ample cabinetry and table space. The primary suite includes a walk-in closet and a private bath with a soaking tub, while the finished lower level provides

  

  Walther Vasquez Johnson

  Samson Properties

  609 Quartzite Cir, Winchester, VA 22601
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  /2

  $400,000

  Coming Soon

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

  1853 Rosser Ln, Winchester, VA 22601

  Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms and 2 full bathrooms. The open floor plan feels bright and spacious, with vaulted ceilings, plenty of natural light, and luxury vinyl plank flooring throughout. The kitchen includes granite countertops, updated cabinets,

  Sarena Baker Realty FC, LLC

  1853 Rosser Ln, Winchester, VA 22601
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  /50

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,678 Sq Ft

  1004 Pennsylvania Ave, Winchester, VA 22601

  Charming, Updated Rancher in the Heart of Winchester! Welcome home to this impeccably maintained 3-bedroom, 2-bath ranch offering the perfect blend of comfort, character, and convenience—all on one level! From the moment you arrive, you'll appreciate the pride of ownership and thoughtful updates throughout. The spacious kitchen is the heart of the home, offering abundant cabinetry and room to

  Traci Shoberg Samson Properties

  1004 Pennsylvania Ave, Winchester, VA 22601
• 

  

  /23

  $127,750

  • Land
  • 8.11 Acres
  • $15,752 per Acre

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602

  Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by, making for easy

  Chad Pangle Whitetail Properties Real Estate

  0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602
• 

  

  /23

  $127,750

  • Land
  • 8.11 Acres
  • $15,752 per Acre

  0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602

  Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by making for easy and

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602
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  /50

  $379,000

  • 3 Beds
  • 3.5 Baths
  • 2,160 Sq Ft

  2104 Stoneleigh Dr, Winchester, VA 22601

  Situated in the charming Orchard Hill subdivision, this delightful twin home offers a perfect blend of comfort and functionality. Built in 1987, this Colonial-style residence boasts a classic brick exterior that exudes warmth and character. With over 2,000 square feet of thoughtfully designed living space, this home is ideal for those seeking a cozy retreat. As you approach the property, you'll

  Kim Hurst MarketPlace REALTY

  2104 Stoneleigh Dr, Winchester, VA 22601
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  /2

  $180,000

  • 3 Beds
  • 1 Bath
  • 1,054 Sq Ft

  309 Liberty Ave, Winchester, VA 22601

  Opportunity awaits at 309 Liberty Avenue in Winchester City. This classic Cape Cod offers the chance to create something truly special in an area experiencing continued growth, infrastructure improvements, and neighborhood investment. The property does require substantial work, making cash financing the most likely option; however, the potential is significant for a buyer with the vision to

  Rick Guthrie Keller Williams Realty

  309 Liberty Ave, Winchester, VA 22601
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  /76

  $719,000

  • 7 Beds
  • 5 Baths
  • 4,736 Sq Ft

  2700 Loyalty Ct, Winchester, VA 22601

  Situated on a prominent corner lot in an exclusive cul-de-sac enclave of distinguished homes, this impressive stone-front residence offers exceptional space, comfort, and timeless appeal in one of the area’s most desirable neighborhoods. Ideally located near fine dining, shopping, banks, and everyday conveniences, the home combines luxury living with unmatched accessibility.Built in 2011 and

  Elcy Pereira Elcy & Co. Realty, LLC.

  2700 Loyalty Ct, Winchester, VA 22601
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  /46

  $435,000

  Open House 8/16

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  338 Lanny Dr, Winchester, VA 22601

  Come home to Whittier Acres and this well maintained Rancher with 1-car garage just minutes from Winchester Medical Center. You'll love the cozy living room with wood burning fireplace, crown molding & built in bookshelves. Gleaming hardwood floors grace the main level (just refinished). The kitchen has a French door refrigerator, electric range, built-in microwave, dishwasher, a built-in spice

  Gina Chatham Century 21 Redwood Realty

  338 Lanny Dr, Winchester, VA 22601
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  /26

  $429,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,844 Sq Ft

  1310 Whittier Ave, Winchester, VA 22601

  Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a

  Sarah Hott Realty ONE Group Old Towne

  1310 Whittier Ave, Winchester, VA 22601
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  /44

  $360,000

  Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,230 Sq Ft

  117 E Pall Mall St, Winchester, VA 22601

  Welcome home to 117 E Pall Mall St! Ideally located within a mile of Shenandoah University and historic downtown Winchester! This 3 bedroom, 2.5 bath has lots of updates and upgrades! Updated kitchen and baths, stainless steel appliances, & a fenced in backyard! 2023 - Roof, siding, & electrical panel (and all breakers), updated kitchen and all baths, 2024 - repaired sump pump & new hot water

  

  Becky Wallace

  Pearson Smith Realty, LLC

  117 E Pall Mall St, Winchester, VA 22601
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  /51

  $364,000

  $15K PRICE DROP

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

  2055 Cidermill Ln, Winchester, VA 22601

  PRICE ADJUSTMENT. 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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  /45

  $334,900

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  913 Orchard Hill Dr, Winchester, VA 22601

  New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter

  Dallas Croft Samson Properties

  913 Orchard Hill Dr, Winchester, VA 22601
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  /17

  $295,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1314 S Braddock St, Winchester, VA 22601

  1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room

  Jacqueline Moore Open Door Brokerage, LLC

  1314 S Braddock St, Winchester, VA 22601
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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
• 

  /2

  $300,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft

  361 E Piccadilly St, Winchester, VA 22601

  In the heart of Winchester with 3 bedrooms and 1 full bath. Hardwood floors, fresh paint, kitchen with granite countertops, appliances, including full-sized washer and dryer. Lots of storage and private fenced backyard. Close to amenities. You don't want to miss this one!

  

  Stacy Martin

  Keller Williams Realty/Lee Beaver & Assoc.

  361 E Piccadilly St, Winchester, VA 22601
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  /38

  $420,000

  • 2 Beds
  • 2 Baths
  • 1,431 Sq Ft

  1826 Kershaw Ln, Winchester, VA 22601

  Welcome to 1826 Kershaw Lane in Willow Lawn Cottages, one of Winchester, Virginia's most sought-after 55+ active adult communities, offering low-maintenance, single-level living just minutes from Historic Old Town Winchester.This beautifully maintained 2-bedroom, 2-bath ranch home showcases exceptional pride of ownership with beautiful hardwood flooring, soaring vaulted ceilings, and an open

  RoxAnn Grimes RE/MAX Roots

  1826 Kershaw Ln, Winchester, VA 22601
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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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  /18

  $259,000

  $16K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  135 S Kent St Unit 202, Winchester, VA 22601

  Step into the charm of Historic Downtown Winchester with this beautifully renovated Urban Lofts Condominium, where history and modern living come together. Located in a home built in 1825, this unique property is just a short stroll to Winchester's favorite restaurants, boutique shopping, coffee shops, museums, and downtown events. Renovated in 2021, the condo offers stylish updates while

  Sharon Farinholt Realty ONE Group Old Towne

  135 S Kent St Unit 202, Winchester, VA 22601
• 

  

  /19

  $329,990

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,576 Sq Ft

  Juniper Plan at Old Town Green, Winchester, VA 22601

  Welcome to Ryan Homes at Old Town Green, experience life in Old Town Winchester with the city's lowest priced garage townhomes, just a short walk to shops, dining and recreation. The Juniper townhome combines all the amenities of single-family living with total convenience. The main level is highlighted by a gourmet kitchen that's open to the living area so you'll never miss a moment. The kitchen

  Ryan Homes Builder

  306 Smalts Cir Unit 41303475, Winchester, VA 22601
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  /34

  $435,000

  $40K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,682 Sq Ft

  21 E Germain St, Winchester, VA 22601

  Seller offering closing cost assistance on select offers—contact the listing agent for details. Welcome to this beautifully renovated historic home in the heart of Old Town Winchester, where timeless charm meets modern living. This move-in-ready 4-bedroom, 2-bath home has been thoughtfully updated throughout, featuring a stunning kitchen with quartz countertops, custom cabinetry, stainless steel

  Diego Ferrando Samson Properties

  21 E Germain St, Winchester, VA 22601
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  /127

  $3,175,000

  • 6 Beds
  • 7 Baths
  • 8,593 Sq Ft

  730 Merrimans Ln, Winchester, VA 22601

  A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city limits. Perfectly positioned on 5.49 acres of breathtaking, park-like grounds, this historic masterpiece is a true private oasis. Painstakingly and lovingly renovated, the estate offers an unparalleled blend of 18th-century charm

  Justin Mistretta Berkshire Hathaway HomeServices PenFed Realty

  730 Merrimans Ln, Winchester, VA 22601
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  /53

  $569,000

  • 4 Beds
  • 4 Baths
  • 2,489 Sq Ft

  687 Woodland Ave, Winchester, VA 22601

  Exceptional opportunity to own this beautifully crafted custom all-brick home on Winchester's desirable east side, nestled in an established neighborhood just minutes from Route 7, downtown Winchester, schools, shopping, dining, hospitals, and major commuter routes.Designed for both everyday living and entertaining, this impressive residence features an open-concept floor plan with gleaming

  Katy Donovan Keller Williams Realty

  687 Woodland Ave, Winchester, VA 22601
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  /32

  $530,000

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

  108 Morgan St, Winchester, VA 22601

  Welcome to this charming historic home in Old Town. A spacious 3-bedroom Colonial, where timeless character meets modern comfort in the heart of Winchester. Thoughtfully updated with today's buyer in mind, this charming residence offers upgraded amenities while preserving its classic appeal. Inside, you'll find generous living spaces filled with natural light, along with a walk-up attic offering

  Stacey Rowe Real Broker LLC

  108 Morgan St, Winchester, VA 22601
• 

  

  /6

  $220,000

  $79K PRICE DROP

  • Studio
  • 1,730 Sq Ft

  384 National Ave, Winchester, VA 22601

  Discover the potential of this 4-bedroom, 2-bath multi-family property offering 1,730 sq ft of living space ona 2,684 sq ft lot. Built in 1930, this property is a great opportunity for investors or buyers looking torenovate and add value. Don't miss your chance to make this income-producing property your next project!

  Derek Greene The Greene Realty Group

  384 National Ave, Winchester, VA 22601
• 

  

  /19

  $406,190

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,689 Sq Ft

  1813 Sloane St, Winchester, VA 22601

  1813 Sloane St. is an attractive new 3 level townhome with full brick front in Winchester, VA for August move-in. Included Deck for first 3 homebuyers! Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  1813 Sloane St, Winchester, VA 22601
• 

  

  /26

  $374,990

  New Construction

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

  HOMESITE 8 Monteith Dr, Winchester, VA 22601

  Open House this Saturday & Sunday from 2-4 PM!End of Row Townhome with 3 Bedrooms & 3.5 Bathrooms! All Three Levels Finished! Explore Winchester’s new luxury townhome community. This three level end unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with

  DRB Homes Builder

  HOMESITE 8 Monteith Dr, Winchester, VA 22601
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  /34

  $524,900

  • 3 Beds
  • 3.5 Baths
  • 3,021 Sq Ft

  1352 Ramseur Ln, Winchester, VA 22601

  Welcome to this beautifully maintained townhome in the desirable Meadowbranch Mews community, where comfort, style, and convenience come together. Featuring three bedrooms and three-and-a-half bathrooms, this brick-front home offers timeless curb appeal and thoughtfully designed living spaces throughout. Step inside to a welcoming foyer with tile flooring that leads to an open and inviting main

  Melissa Donnelly Redfin Corporation

  1352 Ramseur Ln, Winchester, VA 22601
• 

  

  /3

  $350,000

  • Studio
  • 1,654 Sq Ft

  211, 213-215 E Clifford St, Winchester, VA 22601

  Exceptional investment opportunity in the heart of Winchester! This unique offering includes three income-producing rental units for one price: one duplex and one single-family home located at 211, 213, and 215 E. Clifford Street. The duplex features two separate 2-bedroom, 1-bath units, while the single-family home also offers 2 bedrooms and 1 full bath. The properties are deeded separately as

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  211, 213-215 E Clifford St, Winchester, VA 22601
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  /35

  $334,000

  $3K PRICE DROP

  • 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

  124 Worsham Terrace, Winchester, VA 22602
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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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  /47

  $330,000

  $19K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,566 Sq Ft

  101 Locust Ave, Winchester, VA 22601

  Welcome to 101 Locust Avenue in the heart of Winchester on a spacious corner lot! This solid brick ranch home offers 3 bedrooms, 2.5 bathrooms, and comfortable one-level living with additional space in the lower level. The bright and spacious living room serves as the centerpiece of the home, featuring a large bay window that fills the space with natural light. On the main level there are three

  Angela Duncan MarketPlace REALTY

  101 Locust Ave, Winchester, VA 22601
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  /103

  $899,000

  • 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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  /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
• 

  

  /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
• 

  /2

  $325,000

  $40K PRICE DROP

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

  719 National Ave, Winchester, VA 22601

  Priced to sell! 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

  Windy Harris Hunt Country Sotheby's International Realty

  719 National Ave, Winchester, VA 22601
• 

  

  /31

  $545,000

  $15K PRICE DROP

  • 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
• 

  

  /89

  $539,000

  Open Sat 11AM - 12PM $71K PRICE DROP

  • 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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