Winchester, VA Houses for Sale

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  /41

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,165 Sq Ft

  327 Bryarly Rd, Winchester, VA 22603

  Charming Countryside Cape Cod on a Meticulously Maintained 1.25 acres! Motivated seller! Welcome to 327 Bryarly Drive, Winchester, VA 22603 – a beautifully updated Cape Cod-style home nestled on a serene and private 1.25 Acre lot. Originally built in 1941, this residence exudes countryside charm and character, while offering numerous modern upgrades.Step inside to discover 3 spacious

  Lisa Behr Coldwell Banker Premier

  327 Bryarly Rd, Winchester, VA 22603
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  /56

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,581 Sq Ft

  1080 Old Bethel Church Rd, Winchester, VA 22603

  Notice: Private Property/Working Homestead, Do NOT enter/walk property without appointment. Turnkey Homestead on 5+ Acres | Updated 4BR Home with Farm InfrastructureWelcome to this versatile and well-maintained property located in the pastoral countryside of Frederick County, VA. Situated on 5.07 acres, this 4-bedroom, 3.5-bath home offers modern updates, flexible living spaces, and a

  Samantha Armel EXP Realty, LLC

  1080 Old Bethel Church Rd, Winchester, VA 22603
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  /58

  $1,129,000

  • 6 Beds
  • 5.5 Baths
  • 6,174 Sq Ft

  1020 Breckinridge Ln, Winchester, VA 22601

  A place to grow, gather, and stay awhile! From the moment you arrive, this property greets you with thoughtful details and a sense of home you can feel. A brick-paved, rocking chair-worthy front porch sets the tone, and the charming side porch with composite decking is both stylish and maintenance-free. This spacious 6+ bedroom/5.5 bath residence features a main-level bedroom and full bath—ideal

  Sheila Pack RE/MAX Roots

  1020 Breckinridge Ln, Winchester, VA 22601
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  /25

  $244,900

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  132 Erie Trail, Winchester, VA 22602

  This move-in ready home in the sought-after Shawneeland community offers the perfect blend of modern comfort and natural beauty. Featuring a newer roof, newer washer and dryer, updated lighting and fixtures, and a beautifully renovated bathroom and kitchen, this home has everything done for you. The primary bedroom currently holds a queen size bed for reference. This single level home showcases

  Ember Crow Pearson Smith Realty LLC

  132 Erie Trail, Winchester, VA 22602
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  /40

  $465,000

  • 4 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1709 Reaves St, Winchester, VA 22601

  Please take off shoes and give feedback. Step into this beautifully cared-for home featuring new roof (2023) New HVAC System (2024) new LVP floors throughout the basement a spacious, inviting layout. The large kitchen offers plenty of room for meal prep and flows effortlessly into the dining and living rooms — perfect for family gatherings and entertaining. The finished basement boasts a

  Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

  1709 Reaves St, Winchester, VA 22601
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  /28

  $344,900

  • 3 Beds
  • 1 Bath
  • 1,376 Sq Ft

  230 Allison Ave, Winchester, VA 22601

  Welcome to 230 Allison Avenue, a recently renovated 3-bedroom, 1-bath home on a spacious 0.23-acre lot in Winchester. Ideally located just 1 mile from Winchester Medical Center and only minutes to Walmart Supercenter, shops, restaurants, and vibrant downtown Winchester, this home offers both convenience and charm. Step inside to discover a thoughtfully updated interior featuring luxury vinyl

  Jon Fleming Weichert Realtors - Blue Ribbon

  230 Allison Ave, Winchester, VA 22601
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  /18

  $299,000

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

  711 E Cork St, Winchester, VA 22601

  Welcome home to 711 E. Cork Street! Centrally located in Winchester, VA. Enjoy the ease of access to downtown Winchester, Jim Barnett Park, shopping, and commuter routes. This 2 bedroom 1 1/2 bath detached home with brand new exterior update(new vinyl siding). Deeded right away provides access to rear of the property. The right of way is not the actual gravel driveway in place

  Jim Stafford ERA Oakcrest Realty, Inc.

  711 E Cork St, Winchester, VA 22601
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  /81

  $1,224,000

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

  801 Armistead St, Winchester, VA 22601

  Step into refined elegance and exceptional quality in this beautifully upgraded residence, located in one of Winchester’s most desirable and walkable neighborhoods. This stately home offers the perfect blend of timeless architecture, sophisticated updates, and a lifestyle of convenience—just minutes from charming downtown shops, acclaimed restaurants, picturesque parks, and Winchester Medical

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  801 Armistead St, Winchester, VA 22601
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  /40

  $699,900

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  200 Sweetbriar Ln, Winchester, VA 22603

  Welcome to your dream escape! This custom-built cabin on 7.02 acres in Winchester, VA offers the perfect blend of peace, privacy, and high-end living. Whether you're seeking a serene getaway or a functional farmette, this property has it all — with a mix of open pasture and woods, it’s ideal for animals, gardening, or simply soaking in nature.Step inside to find gleaming hardwood floors

  Lori Hoffman Realty ONE Group Old Towne

  200 Sweetbriar Ln, Winchester, VA 22603
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  /18

  $449,900

  • 3 Beds
  • 3 Baths
  • 1,924 Sq Ft

  275 Greenwood Rd, Winchester, VA 22602

  Charming split-foyer home situated on a generous 13,000 sq. ft. lot with convenient access to Routes 7 and 81. The main level boasts neutral-toned walls and a distinctive dual-sided fireplace, seamlessly connecting the living and dining areas. The dining room and well-appointed kitchen feature elegant hardwood flooring and an abundance of natural light, enhanced by a full-size window and sliding

  Jose Ugaz Gates Smart Realty, LLC

  275 Greenwood Rd, Winchester, VA 22602
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  /52

  $300,000

  • 2 Beds
  • 4 Baths
  • 2,438 Sq Ft

  102 Duwamish Trail, Winchester, VA 22602

  If you are looking for a home with privacy and a peaceful rural feel but only 15 minutes to Winchester then this home is for you! Set in a natural habitat, 102 Duwamish Trail has a vintage feel and could be a weekend getaway or your primary residence away from the city. No HOA! There is an open feel to the main level which has a versatile floor plan. There is a sunroom, a family room & a

  Dorothy Beach Samson Properties

  102 Duwamish Trail, Winchester, VA 22602
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  /27

  $339,000

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  425 Beechcroft Rd, Winchester, VA 22601

  Looking for one level living in a sturdy, large (over 2000+/- SF) brick rancher close to all amenities? Restaurants and stores all within a couple of miles including Jim Barnett Park (swimming pools, yay). Easy access to major commuter routes. Relax on the huge front porch or rear covered patio in the private, fully fenced backyard. Semi-open floor plan in the main area bracket the kitchen

  Laurel Murray Samson Properties

  425 Beechcroft Rd, Winchester, VA 22601
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  /60

  $349,990

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft

  1005 Pennsylvania Ave, Winchester, VA 22601

  This charming classic brick ranch in Winchester, VA, features 3 bedrooms and 2 full bathrooms, with easy access to downtown Winchester. As you approach, the covered front porch sets a welcoming tone. The basement has a separate entrance and additional space for bedrooms, a laundry area, and a full bathroom. Recent updates include an HVAC system, a washer and dryer, and complete renovations of

  Nathalie Acosta Spring Hill Real Estate, LLC.

  1005 Pennsylvania Ave, Winchester, VA 22601
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  /62

  $765,000

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

  1877 Clayton Ridge Dr, Winchester, VA 22601

  Nestled at the end of a quiet cul-de-sac and backing to serene wetlands and a protected preserve, this expansive colonial offers over 5,000 square feet of refined living space on nearly half an acre—providing both privacy and picturesque views. Boasting 4 generously sized bedrooms and 4.5 bathrooms, this home features a comfortable and functional main level layout perfect for everyday living and

  Dave Spence RE/MAX Roots

  1877 Clayton Ridge Dr, Winchester, VA 22601
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  /49

  $599,000

  • 5 Beds
  • 3 Baths
  • 3,200 Sq Ft

  1019 Berryville Ave, Winchester, VA 22601

  1019 Berryville Avenue, Winchester, VA 22601 is a Fully-rented triplex located just minutes from Old Town Winchester and Shenandoah University. This approximately 3,000 sq. ft. property is configured as three fully independent residential and commercial units. All units have private entrances, full kitchens, and separate electric. Middle unit may be used for commercial space. Units have been

  Pamela Debnam Houwzer, LLC

  1019 Berryville Ave, Winchester, VA 22601
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  /14

  $324,900

  • 3 Beds
  • 1.5 Baths
  • 1,704 Sq Ft

  10 Richards Ave, Winchester, VA 22601

  Back on the market with updated baths and brand-new flooring in the enclosed porch! Welcome to this charming classic home located in the City of Winchester. Built in 1940, this home offers timeless appeal and craftsmanship. Inside, you'll find 3 bedrooms, 1.5 baths, and a versatile fourth room—ideal for a home office, guest room, or creative space. The main level greets you with a welcoming

  Lindsey Richardson ERA Oakcrest Realty, Inc.

  10 Richards Ave, Winchester, VA 22601
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  /47

  $600,000

  • 4 Beds
  • 3 Baths
  • 2,203 Sq Ft

  167 Morning Glory Dr, Winchester, VA 22602

  Welcome to the beautiful Twin Lakes Community! This charming ranch-style residence offers the ease of one-level living with a spacious and thoughtfully designed floor plan. The main level features a welcoming front den—perfect for a home office or reading nook—an updated kitchen with a large pantry area, a dining room filled with natural light, and a cozy family room complete with a gas

  Lisa Behr Coldwell Banker Premier

  167 Morning Glory Dr, Winchester, VA 22602
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  /69

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,189 Sq Ft

  1793 N Hayfield Rd, Winchester, VA 22603

  Back on the market - the buyer's home did not sell.Charming all-brick ranch home on a spacious .97-acre lot, featuring 3 bedrooms, 2.5 baths, and traditional style throughout. Enjoy a covered front porch, rear deck, living room with fireplace, separate dining room, and eat-in kitchen. Includes a 2-car garage and no HOA. Ideally located—peaceful setting just outside of town, yet only 10

  RoxAnn Grimes RE/MAX Roots

  1793 N Hayfield Rd, Winchester, VA 22603
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  /47

  $450,000

  • 3 Beds
  • 1.5 Baths
  • 1,952 Sq Ft

  164 Bethel Grange Rd, Winchester, VA 22603

  Beautiful brick ranch in a lovely rural setting with mountain views and only minutes to town amenities. Sellers are installing new central air conditioning . 3 bedrooms, 1 1/2 baths with a shower stall in mud room downstairs. Country kitchen with adjoining carport. Large living room front window with nice view of Round Hill. Extra closets. 4 ft hallway with ceiling fan. 5x16 covered front

  Cathy Durbin Crum Realty, Inc.

  164 Bethel Grange Rd, Winchester, VA 22603
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  /56

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,937 Sq Ft

  442 Frog Hollow Rd, Winchester, VA 22603

  Nestled in the serene Frog Hollow Estates, this charming Colonial home offers a perfect blend of comfort and functionality. With four spacious bedrooms and 2.5 bathrooms, the interior is designed for modern living. The traditional floor plan flows seamlessly into a family room off the kitchen, creating a warm atmosphere for entertaining. Step outside to discover 16 acres of picturesque land,

  Wendy Conner Coldwell Banker Premier

  442 Frog Hollow Rd, Winchester, VA 22603
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  /37

  $389,000

  • 3 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  31 W Whitlock Ave, Winchester, VA 22601

  Charming Home Near Handley High School – Move-In Ready!Welcome to this beautifully updated home in a fantastic downtown location—just a short walk to shops, restaurants, and all that the vibrant city center has to offer. This property features a converted garage that now serves as a versatile studio space, perfect for a home office, art studio, or guest suite.Enjoy a spacious,

  Meridee Powars Link Realty Services LLC

  31 W Whitlock Ave, Winchester, VA 22601
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  /58

  $724,900

  • 4 Beds
  • 3 Baths
  • 3,482 Sq Ft

  1419 Ramseur Ln, Winchester, VA 22601

  (Not a 55 community)This beautifully maintained brick front rancher offers a spacious layout with 4 bedrooms and 3 full baths, situated in the desirable Early's Green at Meadowbranch community.Enjoy the comfort of single-level living with the added bonus of a finished basement with a professionally built bar—perfect for entertaining, hobbies, or extra living space. Hardwood flooring under

  Sheila Pack RE/MAX Roots

  1419 Ramseur Ln, Winchester, VA 22601
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  /87

  $699,900

  • 5 Beds
  • 6 Baths
  • 3,824 Sq Ft

  504 Old Fort Rd, Winchester, VA 22601

  Handsome Colonial loaded with possibilities, from a multigenerational home to spacious entertaining venues. It features a Main Floor ensuite Bedroom and expansive finished basement with kitchenette and outside entrance for possible in-law suite. Inviting lot with large pool and covered and open decks in large privacy fenced back yard. Conveniently located in lovely, well-maintained

  Dallas Croft Samson Properties

  504 Old Fort Rd, Winchester, VA 22601
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  /27

  $349,900

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  509 W Cork St, Winchester, VA 22601

  Location, Location, Location! Nestled in the heart of Winchester on the sought-after west side, this recently renovated 3-bedroom, 1-bath home offers modern comforts with a touch of classic charm. Step inside to discover a brand-new kitchen featuring gleaming white cabinets and exquisite granite countertops, perfect for culinary enthusiasts. The updated bathroom boasts a stylish tiled tub,

  Dan Whitacre Colony Realty

  509 W Cork St, Winchester, VA 22601
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  /13

  $910,000

  • 2 Beds
  • 1 Bath
  • 609 Sq Ft

  196 Hodges Ln, Winchester, VA 22603

  Incredible Builder or Private Estate Opportunity on Nearly 80 Acres!This 79.16-acre property, located less than 15 miles from Winchester, offers the perfect blend of rural seclusion and convenient access. Tucked away in a peaceful setting, this land presents a rare opportunity for developers to build 7+ homes, or for an individual to create a private dream retreat surrounded by nature. The

  Sarah Reynolds Keller Williams Realty

  196 Hodges Ln, Winchester, VA 22603
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  /28

  $475,000

  • 6 Beds
  • 3 Baths
  • 2,736 Sq Ft

  386 Round Hill Rd, Winchester, VA 22602

  ATTENTION INVESTORS - OFFERED AT A NEW PRICE!! *** You will want to check out this fantastic opportunity - with a history of POSITIVE CASH FLOW these two ADJACENT PROPERTIES on a combined total of 1.91-acres in Winchester, just minutes from Valley Health Campus, shopping, restaurants and Rt. 37, may be what you are looking for! *** These two parcels are to be sold TOGETHER; they are not

  Bridget Aikens Colony Realty

  386 Round Hill Rd, Winchester, VA 22602
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  /34

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  12 Montague Cir, Winchester, VA 22601

  Welcome to 12 Montague Circle — a recently updated 3-bedroom, 1.5-bath home tucked away in a quiet cul-de-sac in downtown Winchester. Enjoy the best of both worlds with a peaceful, private setting and immediate access to restaurants, shops, grocery stores, and all the charm the city has to offer. This recently renovated gem features a new roof and HVAC system, durable and modern LVP flooring, and

  Jon Fleming Weichert Realtors - Blue Ribbon

  12 Montague Cir, Winchester, VA 22601
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  /46

  $344,000

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

  308 Fawn Dr, Winchester, VA 22602

  Charming 3-Bedroom Home in Desirable Wilde Acres CommunityWelcome to this beautifully maintained 3-bedroom, 2.5-bath home, nestled on a spacious and flat lot in the sought-after Wilde Acres neighborhood. Featuring a 2-bay garage and fresh paint throughout, this move-in-ready home offers comfort, functionality, and a touch of nature all in one.Inside, enjoy a generous kitchen perfect for

  Kathrin Donovan Keller Williams Realty

  308 Fawn Dr, Winchester, VA 22602
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  /35

  $319,900

  • 4 Beds
  • 2 Baths
  • 2,304 Sq Ft

  911 Martinsburg Pike, Winchester, VA 22601

  Charming 1931 Home with Timeless Appeal & New Metal Roof – 911 Martinsburg Pike, WinchesterStep into a piece of Winchester history with this stunning "four-square" home, offering a perfect blend of old-world charm and modern convenience. Boasting 4 spacious bedrooms (5 if you make the main level room into a bedroom) and 2 full baths, including a main-level en suite, this home is designed for

  Sarah Abderrazzaq Realty ONE Group Old Towne

  911 Martinsburg Pike, Winchester, VA 22601
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  /53

  $475,000

  • 4 Beds
  • 2 Baths
  • 2,012 Sq Ft

  669 Dicks Hollow Rd, Winchester, VA 22603

  Welcome to this spacious farmhouse on FIVE acres! NEW TWO ZONE HEAT AND AC BEING INSTALLED ON TUESDAY THE 17TH! NEW hot water heater! NEWER windows throughout. Metal roof - large detached two car garage with large work area. Pole barn and garden shed! Apple trees, peach tree - 15 minutes to town! All windows are newer as well. WOOD FLOORS! LARGE wrap around deck! Hiking trails on

  Barbera Clausen EXP Realty, LLC

  669 Dicks Hollow Rd, Winchester, VA 22603
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  /27

  $344,990

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

  144 Falcon Trail, Winchester, VA 22602

  Charming Split Foyer Home in Shawneeland – 144 Falcon Trail, Winchester, VAWelcome to 144 Falcon Trail, a delightful 3-bedroom, 2.5-bathroom split foyer residence nestled in the serene Shawneeland community of Winchester, VA. Built in 2009, this 1,566 sq ft home offers a perfect blend of comfort and potential, making it an ideal choice for first-time buyers or savvy investors.Enjoy a traditional

  Susan Wathen EXP Realty, LLC

  144 Falcon Trail, Winchester, VA 22602
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  /18

  $355,000

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft

  2940 Grace St, Winchester, VA 22601

  Welcome to your charming Cape Cod retreat! Built in 1955, this delightful 3-bedroom, 1-bath home offers a warm and inviting atmosphere—perfect for anyone looking for a cozy and welcoming place to call home. --- Step inside to a thoughtfully designed layout that makes the most of the 936 square feet of finished living space. --- Home is equipped with energy-efficient solar panels to help reduce

  Lauren Smith-Washbourne Coldwell Banker Premier

  2940 Grace St, Winchester, VA 22601
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  /40

  $374,500

  • 3 Beds
  • 2.5 Baths
  • 1,466 Sq Ft

  124 Wilkins Dr, Winchester, VA 22602

  Welcome home to this newly remodeled and upgraded ranch style home. All the convenience of one level living, with the option of a basement full of possibilities. Step into the spacious living room, complete with fireplace, as you walk in the front door. Continue through the wonderful flow of the house into the dining room and open kitchen. Enjoy making your meals in the fully renovated kitchen

  Dave Spence RE/MAX Roots

  124 Wilkins Dr, Winchester, VA 22602
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  /43

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,299 Sq Ft

  341 Opequon Ave, Winchester, VA 22601

  Welcome home to this charming 3-bedroom, 1.5-bath gem perfectly located for easy access to I-81, Route 50, and Route 7—ideal for commuters. SEE VIDEO attached :)Enjoy the convenience of a main-level laundry room and peace of mind with a new roof installed in 2018. Step outside to your fully fenced backyard, complete with a screened-in porch and storage shed, perfect for relaxing or extra

  Sheila Pack RE/MAX Roots

  341 Opequon Ave, Winchester, VA 22601
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  /42

  $769,900

  • 3 Beds
  • 3 Baths
  • 2,112 Sq Ft

  1049 Laurel Grove Rd, Winchester, VA 22602

  Nestled at the end of a peaceful cul-de-sac, this stunning, property offers the perfect blend of seclusion and community living. This custom-designed home offers three bedrooms and three bathrooms, with the convenience of main-level living. Surrounded by lush woodlands and boasting breathtaking views of both trees and mountains, this property is ideal for those seeking a tranquil retreat that

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
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  /41

  $309,900

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

  601 Grove St, Winchester, VA 22601

  601 Grove Street, is a single-family home offering a blend of comfort and convenience. Built in 1980, this 1,152 sq ft ranch-style residence features 3 bedrooms and 1 full bath on the main level, complemented by a partially finished basement that includes an additional bathroom and laundry area. The basement also offers versatile spaces that can serve as extra bedrooms, an office, or a recreation

  Lilly Triplett Colony Realty

  601 Grove St, Winchester, VA 22601
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  /72

  $699,000

  • 4 Beds
  • 4.5 Baths
  • 4,320 Sq Ft

  292 Green Spring Rd, Winchester, VA 22603

  Welcome to your dream home! Nestled on just over 5 serene acres, this beautifully maintained 4-bedroom, 4.5-bathroom property offers the perfect blend of comfort, style, and functionality. From the moment you arrive, you’ll be charmed by the picturesque country and mountain views and the orchard-like feel created by numerous fruit trees (peaches, pears, apples, and cherries) lining the front

  Katie Landi Jordan Samson Properties

  292 Green Spring Rd, Winchester, VA 22603
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  /81

  $689,900

  • 4 Beds
  • 3.5 Baths
  • 4,411 Sq Ft

  226 Taggart Dr, Winchester, VA 22602

  Welcome to 226 Taggart Drive – a sunlit Colonial in the heart of Winchester's sought-after Raven Pointe community.This spacious 4-bedroom, 3.5 bath home offers over 4,200 square feet of beautifully finished living space across three levels, thoughtfully designed for comfort, functionality, and quiet everyday living. Nestled on a peaceful street just minutes from historic downtown Winchester,

  Lilly Triplett Colony Realty

  226 Taggart Dr, Winchester, VA 22602
• 

  

  /29

  $439,000

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

  214 S Braddock St, Winchester, VA 22601

  This property is currently zoned as fully commercial but has the potential to be changed to: Mixed Use or Fully Residential with proper city approval. Additional information from city located in documents. This home will need a Kitchen.Situated in Downtown Winchester, 214 S Braddock is waiting for your ideas! Built in 1865, this home features historic charm including exposed brick walls,

  Matt Leiva Keller Williams Realty

  214 S Braddock St, Winchester, VA 22601
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  /9

  $135,000

  • 1 Bed
  • 1 Bath

  1114 Cedar Grove Rd, Winchester, VA 22603

  Property has a great location but is probably a tear down. Health Documents available showing location of well/septic.

  Dave Spence RE/MAX Roots

  1114 Cedar Grove Rd, Winchester, VA 22603

Showing Results 81 - 120, Page 3 of 6