Winchester, VA Homes under $400,000

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  /42

  $349,000

  • 3 Beds
  • 1.5 Baths
  • 1,178 Sq Ft

  107 E Monmouth St, Winchester, VA 22601

  Charming Historic Home in Downtown Winchester – Move-In Ready!If you love timeless craftsmanship—think original wood floors, custom built-ins, and vintage doors—but still want the ease of modern living, this beautifully updated downtown Winchester home is calling your name!From the moment you step onto the inviting covered porch and through the front door, you’ll feel right at home. Warm wood

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 590-5989

  107 E Monmouth St, Winchester, VA 22601
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  /48

  $339,900

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft

  128 Fox Dr, Winchester, VA 22601

  Welcome to 128 Fox Dr — a spacious, move-in ready home nestled in the heart of Winchester, offering three levels spanning over 2,600 square feet of flexible living space, with 4 bedrooms, 3 bathrooms, and unbeatable convenience! This Cape Cod-style home features a thoughtful layout with at least one bedroom and a full bathroom on every level. Step into the main level to discover hardwood floors

  

  MJ Frazier

  Real Broker, LLC

  (540) 513-5877

  128 Fox Dr, Winchester, VA 22601
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  /50

  $345,000

  • Land
  • 40 Acres
  • $8,582 per Acre

  Mockingbird Lane Lot Unit WP008, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Features a fully functional hunting cabin with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters via a loft. Experience exciting

  Chad Pangle

  Mockingbird Lane Lot Unit WP008, Winchester, VA 22603
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  /60

  $359,990

  • 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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  /37

  $389,000

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

  31 W Whitlock Ave, Winchester, VA 22601

  Wonderful location near Handley High School. Home has been updated and is ready for new owners! Great d downtown location where it is an easy walk to all the downtown shops and restaurants. . Garage has been converted into studio. Large back yard that is fenced,. Lots of new featues to include, HVAC, how water tank and deck!

  Meridee Powars Link Realty Services LLC

  31 W Whitlock Ave, Winchester, VA 22601
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  /27

  $369,000

  • 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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  /51

  $354,999

  • 3 Beds
  • 1 Bath
  • 1,445 Sq Ft

  671 Fox Dr, Winchester, VA 22603

  ESTATE SALE..... "owner's pride" this cozy Ranch well taken care of, PROPERTY OFFERS....separate laundry room with back door entry, 13x13 family room, dining room with patio door going out onto a 10x19 covered deck, one bevel living, beautiful hardwood floors throughout, cozy brick fireplace in living room, pull down attic for extra storage, fenced backyard with dusk-to-dawn pole light, garage

  Wanda Garris Miller Century 21 Redwood Realty

  671 Fox Dr, Winchester, VA 22603
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  /24

  $360,000

  • 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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  /22

  $355,000

  • 3 Beds
  • 2 Baths
  • 1,060 Sq Ft

  601 Fairview Ave, Winchester, VA 22601

  Fully Renovated Gem in the Heart of Winchester! Welcome to 601 Fairview Ave, where modern upgrades meet timeless charm! This beautifully remodeled 3-bedroom, 2-bathroom rambler offers the perfect blend of comfort and convenience in one of Winchester’s most desirable locations.Step inside to discover a brand-new kitchen featuring stylish finishes, sleek countertops, and modern cabinetry—ready for

  Jorge Najarro Samson Properties

  601 Fairview Ave, Winchester, VA 22601
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  /22

  $369,900 Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,607 Sq Ft

  148 Amoco Ln, Winchester, VA 22603

  RENOVATIONS JUST COMPLETED ON 06/01/25! Frederick County B2 zoning on over 1/2 acre. Located just off Interstate 81 and Rt 11, Martinsburg Pike. Main level is 1,142 sq ft with two bedrooms and a walk-in shower in bathroom. Upper level has 465 sq ft with 2 bedrooms and a full bath = 1,607 total sq ft of living area. Plus a full basement. One car carport with additional storage area. NO HOA.

  Leo Smith CENTURY 21 New Millennium

  148 Amoco Ln, Winchester, VA 22603
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  /76

  $400,000

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  2431 Cedar Creek Grade, Winchester, VA 22602

  This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in

  Edward Beightol Cedar Creek Real Estate

  2431 Cedar Creek Grade, Winchester, VA 22602
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  /6

  $360,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,568 Sq Ft

  115 Mountain Lodge Dr, Winchester, VA 22602

  Welcome to your brand-new, private retreat in Mountain Falls! This thoughtfully designed three-story home features open-concept living on the main level, including a spacious kitchen, dining area, family room, convenient main-level laundry, and a half bath. Upstairs, you’ll find a generous primary suite with its own full bath, along with two additional bedrooms and another full bathroom. The

  Abby Walters Preslee Real Estate

  115 Mountain Lodge Dr, Winchester, VA 22602
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  /2

  $399,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft

  Bedford II, Winchester, VA 22601

  Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  DRB Homes

  Bedford II, Winchester, VA 22601
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  /28

  $374,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,752 Sq Ft

  0 Heirloom Way Unit VAFV2021776, Winchester, VA 22603

  Build this Brand New Northgate villa in Brookfield Residential's newest Active Adult community, Hiatt Pointe at Snowden Bridge, a gated community for those persons 55 or better for 2025 move in!This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  0 Heirloom Way Unit VAFV2021776, Winchester, VA 22603
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  /19

  $359,900 New Construction

  • 3 Beds
  • 3 Baths
  • 1,850 Sq Ft

  1619 Tomahawk Trail, Winchester, VA 22602

  Done! Top of the world views! Private. Over 1/2 acre lot private, stunning views of valley and mountains. Side load garage with garage windows across front. 3 bed, 3 full baths, 2 car garage, open floor plan, family rm and kitchen with vault. HW floors entire main floor and stairs, tile floors in all baths, upgraded cabinets. BUILDER BONUS HARDWOOD IN BEDROOMS, BUILDER BONUS GRANITE IN

  Jim Thomson Realty ONE Group Old Towne

  1619 Tomahawk Trail, Winchester, VA 22602
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  /9

  $375,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  115 Tanglewood Ln, Winchester, VA 22602

  Welcome to 115 Tanglewood Lane - Located on a quiet, no-through street in one of Winchester’s incredible 55+ communities, this charming home offers the perfect blend of comfort, convenience, and low-maintenance living. Just minutes from historic downtown Winchester and walking distance to Creekside Station, you'll love having shops, restaurants, and local businesses right at your fingertips.Step

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  115 Tanglewood Ln, Winchester, VA 22602
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  /23

  $369,900 Open Sun 12PM - 3PM

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

  116 Copeley Cir, Winchester, VA 22602

  Beautifully appointed garage townhome available now in Freedom Manor. Less than 3 years old and ideally located on one of the best lots in the neighborhood! Fantastic floor plan offering that highly desirable main level entry making this the home you want for easy living and minimal stairs. Just a few of the interior upgrades include warm luxury vinyl plank flooring spanning the entire main level

  Mike Casto Weichert, REALTORS

  116 Copeley Cir, Winchester, VA 22602
• 

  /2

  $365,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  Completely remodeled! Come enjoy ALL new everything, new electric, new windows, luxury floors, freshlypainted walls and brand-new custom kitchen and bathrooms, and all new plumbing and electricthroughout, nothing has been left untouched! New Mini Split HVAC system. Large living room opens into a gorgeous wrap aroundpeninsula kitchen with brand new Samsung appliances, granite countertop. Dining

  Lawrence Lessin Homes By Owner, Inc.

  553 Highland Ave, Winchester, VA 22601
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  /29

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,315 Sq Ft

  102 Meadowlark Ct, Winchester, VA 22602

  Welcome to this beautifully maintained 3 Bedroom 2 Bath home in the desirable neighborhood of Meadowlark Court in Winchester, Va. With a spacious interior, and a private backyard with a lovely shed for all your gardening tools or for a workshop. All season room off the master bedroom with a hot tub to relax in. This home is perfect for both relaxing and entertaining.

  Suzanne Simpson Fathom Realty

  102 Meadowlark Ct, Winchester, VA 22602
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  /37

  $399,900

  • 4 Beds
  • 1.5 Baths
  • 2,860 Sq Ft

  684 Berryville Ave, Winchester, VA 22601

  Come check out this 4-bedroom 1.5 bath 4 level Brick Colonial with a Detached Garage all on a double lot, updated roof, windows, new plumbing & water heater, updated electric & panel box. There is plenty of room to grow and put your flavor in the walk-up attic and basement. Home has the original Hardwood floors & Beautiful Woodworking that has never been painted throughout. Large, covered front

  Richard Kozlowski Long & Foster Real Estate, Inc.

  684 Berryville Ave, Winchester, VA 22601
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  /28

  $331,000

  • 3 Beds
  • 2.5 Baths
  • 1,210 Sq Ft

  238 Sage Cir, Winchester, VA 22603

  This charming 3-bedroom, 2.5-bath interior townhouse offers a perfect blend of comfort, privacy, and convenience in a highly sought-after, commuter-friendly location. The spacious kitchen features granite countertops and a large center island, opening seamlessly to a bright and inviting family room—ideal for both everyday living and entertaining. Upstairs, the primary suite offers a private

  Laura White ERA Oakcrest Realty, Inc.

  238 Sage Cir, Winchester, VA 22603
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  /61

  $399,900

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

  121 E James St, Winchester, VA 22601

  If your goal is to have an easy walk to Old Town Winchester, this is the home for you! Built in the early 1900's and full of charm!! The family room addition was done in1971 and is absolutely amazing!! Featuring 4 bedroom and 2 baths with approximately 2200 finished square feet!! Heating and air conditioning has been recently updated. The downstairs openness and light is incredible for this age

  Lisa Gill ERA Oakcrest Realty, Inc.

  121 E James St, Winchester, VA 22601
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  /30

  $399,900

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

  1826 Kershaw Ln, Winchester, VA 22601

  This charming one-level home is perfectly situated in one of Winchester's desirable 55+ senior communities, Willow Lawn Cottages. Great home....first time on the market,featuring two spacious bedrooms, two full bathrooms, hardwood floors & vaulted ceilings. The open and inviting floor plan will make your new home ideal for both daily living and entertaining. The large primary suite offers

  Jeff Webber Long & Foster Real Estate, Inc.

  1826 Kershaw Ln, Winchester, VA 22601
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  /28

  $349,900

  • 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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  /30

  $349,000

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  223 Monticello Square, Winchester, VA 22602

  Welcome to this stunning, move-in-ready townhome in the desirable Brookland Manor Subdivision in Winchester, VA! This 3-bedroom, 2.5-bath home boasts an open floor plan, perfect for modern living and entertaining. Interior Features: Hardwood floors grace the main level and staircase, adding warmth and elegance. High ceilings and large daylight windows create a bright, airy atmosphere. Groumet

  Minhkhoa Tran Fairfax Realty Premier

  223 Monticello Square, 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. There is an open feel to the main level which has a versatile floor plan. There is a sunroom, a family room & a kitchen

  Dorothy Beach Samson Properties

  102 Duwamish Trail, Winchester, VA 22602
• 

  

  /25

  $349,988

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

  425 Beechcroft Rd, Winchester, VA 22601

  Looking for a one level living in a sturdy, large brick rancher close to all amenities? This is it; walking distance to Frederick Douglas Elementary School. Restaurants, stores and amenities all within a couple of miles. 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

  Laurel Murray Samson Properties

  425 Beechcroft Rd, Winchester, VA 22601
• 

  

  /31

  $305,000

  • 2 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  7 E Hart St, Winchester, VA 22601

  Beautifully Maintained and Ideally Located!Nestled within city limits and just minutes from shopping, local dining, and the vibrant downtown walking mall, this home offers the perfect blend of comfort and convenience. Recent updates include fresh paint on all interior levels (2025), new carpet (2025), upgraded granite countertops (2019), a 30-year Timberline American Harvest roof (2017), HVAC

  Jennifer Sacco RE/MAX Roots

  7 E Hart St, Winchester, VA 22601
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  /22

  $327,500 Open Sat 11AM - 1:30PM

  • 3 Beds
  • 1.5 Baths
  • 1,634 Sq Ft

  102 Zephyr Ln, Winchester, VA 22602

  Motivated Sellers! Carpet allowance and Professional Cleaning will be provided prior to closing. Don’t miss this opportunity for a Beautifully Updated 3-Bedroom Town home in Prime Location!Welcome to this charming 3-bedroom, 1.5-bath town home located in a highly sought-after neighborhood. Featuring a cozy fireplace in the living room and a stylishly remodeled kitchen with modern finishes,

  Kandi Ross Realty ONE Group Old Towne

  102 Zephyr Ln, Winchester, VA 22602
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  /28

  $305,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  946 Franklin St, Winchester, VA 22601

  REDUCED! Relax on the back decks overlooking a treed canopy yard. Cape code with fresh paint, laminate flooring , large walk-in closets on upper lever with sitting room and 1 bedroom plus attic storage. Main level has 2 bedrooms, bathroom, living room and kitchen with door to back decks and yard. Unfinished basement with plenty of room to expand and for storage. Home has NEW windows 2024, NEW

  Stan Dull The Wiley Companies, Inc.

  946 Franklin St, Winchester, VA 22601
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  /14

  $339,900

  • 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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  /50

  $345,000

  • Land
  • 40 Acres
  • $8,582 per Acre

  0 Mockingbird Lot 8 Ln Unit VAFV2034374, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Mockingbird Lane. Features a fully functional hunting cabin with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters via a loft. Experience exciting

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Mockingbird Lot 8 Ln Unit VAFV2034374, Winchester, VA 22603
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  /36

  $349,900

  • 2 Beds
  • 2.5 Baths
  • 1,238 Sq Ft

  1312 S Kent St, Winchester, VA 22601

  Welcome to this beautifully maintained townhouse featuring 2 spacious bedrooms and 2.5 baths. Enjoy the convenience of both driveway parking and additional parking lot spaces. The modern kitchen boasts quartz countertops, a stylish backsplash, electric cooking, bamboo flooring, a pantry, and a reverse osmosis water system—perfect for any home chef. Located in the heart of downtown Winchester,

  Sheila Pack RE/MAX Roots

  1312 S Kent St, Winchester, VA 22601
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  /30

  $314,900

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft

  140 Mccormick Cir Unit 302, Winchester, VA 22602

  Welcome Home to this gorgeous, like-new condo! This stunning unit was constructed last year and offers the perfect blend of modern elegance and comfort. Enjoy top-tier finishes like quartz countertops, stainless steel appliances, and beautiful LVP flooring throughout.Relax and unwind in the meticulously manicured common grounds, take a stroll on the walking path, or enjoy the convenience of

  Karl Achstetter Keller Williams Realty

  140 Mccormick Cir Unit 302, Winchester, VA 22602
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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 cooking

  Kathrin Donovan Keller Williams Realty

  308 Fawn Dr, Winchester, VA 22602
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  /35

  $329,900 Open Sat 11AM - 1PM

  • 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
• 

  

  /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
• 

  

  /43

  $304,900

  • 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 2021. 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
• 

  

  /41

  $319,900

  • 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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