36

Winchester, VA Homes under $500,000

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  • /69

    $489,900

    • 3 Beds
    • 2.5 Baths
    • 2,028 Sq Ft

    256 Parkway St, Winchester, VA 22601

    Picturesque on Parkway - If you’ve been looking for the beauty and bones of an older home that has been updated tastefully, respecting the original charm, look no further. As you step into this immaculate 1940 colonial, you will be greeted with beautiful hardwood floors running throughout the main living area. The living room boasts built in bookshelves that run to the ceiling and tall windows

    Danielle Spriggs ICON Real Estate, LLC

    256 Parkway St, Winchester, VA 22601
  • /57

    $475,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,532 Sq Ft

    151 Morning Glory Dr, Winchester, VA 22602

    You'll love the convenience of living in the Apple Ridge neighborhood on the east side of Winchester with easy access to Route 7 & I-81. The open floor plan with kitchen, breakfast area & family room offers a great space for everyone to be together during meal prep, homework time, watching TV or just spending time together talking about the day's events. Highlights include the view of the

    Gina Chatham Century 21 Redwood Realty

    151 Morning Glory Dr, Winchester, VA 22602
  • /60

    $499,000

    • 2 Beds
    • 2.5 Baths
    • 1,914 Sq Ft

    720 Adams Rd, Winchester, VA 22603

    Built in 2014, this nearly 2,000 sf modern rancher on 5 mostly wooded acres with no HOA is a hobbyist’s dream! In addition to two attached garages with custom 12’ wide doors, there’s also a 12'x10' attached shed, a 20'x20' workshop, and a detached shed/covered area for any equipment, materials, or supplies that need to be stored. Deer and other wildlife make their home on this property, where you

    Marcy Deck Dandridge Realty Group, LLC

    720 Adams Rd, Winchester, VA 22603
  • /44

    $500,000

    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    1921 Harvest Dr, Winchester, VA 22601

    Save BIG - The Price of this Beautiful Home is Improved!Stunning Colonial in Meadow Branch South – Winchester, VA ** This home is in Move In Condition and can settle quickly!Welcome home to this meticulously maintained Colonial in the sought-after Meadow Branch South community! This 4-bedroom, 2.5-bath home is filled with thoughtful updates and timeless charm.Step inside to gleaming hardwood

    Sue Smith Compass

    1921 Harvest Dr, Winchester, VA 22601
  • /38

    $489,900 Open House 5/10

    • 4 Beds
    • 3.5 Baths
    • 2,892 Sq Ft

    112 Hites St, Winchester, VA 22602

    A Cape Cod like no other! This home boasts over 2800 sq.ft (addition in 2011), which includes two primary suites! The spacious main level features hardwood floors in the entryway, living room and dining room and is adorned by beautiful crown molding throughout. The kitchen features white cabinetry and SS appliances. A main level primary suite features hardwood floors and an attached bathroom,

    Heloisa Amar Samson Properties

    112 Hites St, Winchester, VA 22602
  • /20

    $460,000

    • 5 Beds
    • 3 Baths
    • 2,560 Sq Ft

    106 Donna Cir, Winchester, VA 22602

    This beautiful, remodeled home is very well located, close to shopping and entertainment. The upstairs area features 3 spacious bedrooms, 2 full bathrooms. Also has sleek LVP floors throughout the home. The heart of the home is the sleek, all-new kitchen, equipped with shaker cabinets, quartz countertops, and stainless-steel appliances.The home offers a walkout basement with an

    Marco Novillo Spring Hill Real Estate, LLC.

    106 Donna Cir, Winchester, VA 22602
  • /2

    $469,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,351 Sq Ft

    100 Meadow Way, Winchester, VA 22602

    Brand new construction with stunning mountain views! This beautiful 4 bedroom, 2.5 bath home features elegant hardwood floors and crown molding throughout the main living areas. Enjoy the convenience of the laundry room located on the upper level. The full basement offers endless possibilities for future expansion or storage. Don't miss your chance to own beautiful home with breathtaking views!

    Pamela Russell CENTURY 21 New Millennium

    100 Meadow Way, Winchester, VA 22602
  • /40

    $449,900

    • 3 Beds
    • 3.5 Baths
    • 2,721 Sq Ft

    1324 Ramseur Ln, Winchester, VA 22601

    Elegant Main-Level Condo in The Mews at MeadowbranchWelcome to effortless luxury living in one of Meadowbranch’s most sought-after communities! This stunning main-level condo combines the space and comfort of a single-family home with the convenience and ease of condo living. Bright, open, and beautifully finished, this rare gem in The Mews at Meadowbranch is move-in ready!Inside, you'll find

    Jeanne Mezzatesta Colony Realty

    1324 Ramseur Ln, Winchester, VA 22601
  • /80

    $439,900

    • 4 Beds
    • 2 Baths
    • 1,564 Sq Ft

    2820 Baldwin St, Winchester, VA 22601

    CHARMING SPLIT FOYER HOME WITH 4 BEDROOMS AND 3 FULL BATHROOMS IN WINCHESTER!!!!!THIS WELL-MAINTAINED SPLIT FOYER HOME IN WINCHESTER OFFERS A FUNCTIONAL LAYOUT AND PLENTY OF SPACE. THE MAIN LEVEL FEATURES 3 BEDROOMS AND 2 FULL BATHROOMS, INCLUDING A SEPARATE LIVING ROOM AND DINING AREA, EACH OFFERING A CONFORTABLE SPACE FOR FAMILY TIME AND ENTERTAINING. THE KITCHEN IS READY FOR YOUR

    Carolina Mosquera Weichert, REALTORS

    2820 Baldwin St, Winchester, VA 22601
  • /57

    $445,000 Open Sat 1PM - 4PM

    • 4 Beds
    • 2.5 Baths
    • 1,720 Sq Ft

    803 Berryville Ave, Winchester, VA 22601

    **Welcome to Timeless Beauty—an exquisitely restored 1928 American Four Square, just minutes from Winchester’s Historic District and a commuter’s dream with easy access to Leesburg, Tysons Corner, and the DC Metro area.**This timeless beauty has been *renovated from top to bottom*, blending historic charm with modern luxury. Step through the generous foyer and take in the warmth of the

    Tanya Spotts Long & Foster Real Estate, Inc.

    803 Berryville Ave, Winchester, VA 22601
  • /29

    $429,000

    • 4 Beds
    • 2 Baths
    • 2,134 Sq Ft

    320 S Cameron St, Winchester, VA 22601

    Historic Charm? Check!Modern Amenities? Check!Location? Check!Welcome to 320 S. Cameron Street! Built in 1773, this property will transport you back in time as soon as you arrive! The outside is host to 3 shops/outbuildings; some with power, an English garden, and original horse hitching posts! From the side porch, you will enter a newly renovated kitchen featuring stainless steel appliances and

    Matt Leiva Keller Williams Realty

    320 S Cameron St, Winchester, VA 22601
  • /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
  • /39

    $415,000

    • 3 Beds
    • 2 Baths
    • 1,786 Sq Ft

    265 Greenwood Rd, Winchester, VA 22602

    Beautifully maintained Home is looking for new owners. This lovely raised rambler features a welcoming front porch and 2 car attached garage with shelves for storage. Plenty of driveway space for friends and family. Home is adorned with wood and tile flooring throughout, Benefit from an open concept design with updated Kitchen, complete with quartz countertops, gorgeous backsplash, stainless

    Chanie Erb Berkshire Hathaway HomeServices PenFed Realty

    265 Greenwood Rd, Winchester, VA 22602
  • /27

    $439,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    127 Latane St, Winchester, VA 22601

    ?? LOCATION, LOCATION, LOCATION! Charming Brick Bungalow in Prime Downtown Winchester!?? This delightful three-bedroom, two-bath brick one level home is brimming with charm and ideally located within walking distance of downtown Winchester, Handley High School, the Patsy Cline House, 2-blocks from the parade route, and the historic district. With gorgeous hardwood floors, fresh modern

    Vanessa Couture ERA Oakcrest Realty, Inc.

    127 Latane St, Winchester, VA 22601
  • /42

    $429,900

    • 3 Beds
    • 2 Baths
    • 1,953 Sq Ft

    123 Meadowbrooke Place, Winchester, VA 22602

    This charming rambler is the one you've been looking for! Located at the end of a cul-de-sac on a tree-lined street, this property offers plenty of privacy. Inside you are greeted by a spacious open floor plan, featuring hardwood floors in all of the rooms except the kitchen and bathrooms. The kitchen features an abundance of wood cabinetry, newer SS dishwasher, stove and refrigerator and new

    Heloisa Amar Samson Properties

    123 Meadowbrooke Place, Winchester, VA 22602
  • /50

    $429,000

    • 4 Beds
    • 3 Baths
    • 1,617 Sq Ft

    126 Armstrong Place, Winchester, VA 22602

    All brick ranch home with 4 bedrooms close to town and a short walk to the golf course! Main level large living Room and dinning room, 2 bedrooms and 2 bathrooms, an eat in kitchen, has gleaming hardwood flooring. Lower Level large area for pool table 2 more bedrooms, 1 bathroom and a family room equipped with a brick fireplace and space for a pool table. There is a sliding glass door that leads

    John Scully Colony Realty

    126 Armstrong Place, Winchester, VA 22602
  • /65

    $475,000 Open Sat 12PM - 2:30PM

    • 3 Beds
    • 2 Baths
    • 1,974 Sq Ft

    146 Howards Chapel Rd, Winchester, VA 22603

    Have you ever envisioned owning an incredible ranch with a 5-acre home? This unique opportunity invites you to embrace a serene rural lifestyle, offering vast space for relaxation and small-scale farming endeavors. Picture awakening to the soothing sounds of nature, with the potential to cultivate a flourishing garden, raise livestock, or bask in the tranquility of the countryside. This Property

    Karla Castaneda Berkshire Hathaway HomeServices PenFed Realty

    146 Howards Chapel Rd, Winchester, VA 22603
  • /46

    $427,900

    • 4 Beds
    • 3.5 Baths
    • 1,776 Sq Ft

    103 Fenwick Ct, Winchester, VA 22602

    REDUCED! Come see this 4 (or 5 bedroom), 3.5 bathroom detached home! It's located on a quiet cul-de-sac and convenient to route 7 for commuters. Large private 6 car new paved driveway -so plenty of off-street parking! Whole length of house rear deck for entertaining! RARE main level bedroom (or use as a family room) with attached full bathroom with level rear exterior access! Half bath,

    Sara Helmke Samson Properties

    103 Fenwick Ct, Winchester, VA 22602
  • /34

    $446,000

    • 4 Beds
    • 2 Baths
    • 1,762 Sq Ft

    2320 Tower Ave, Winchester, VA 22601

    HUGE PRICE CUT!!!Don't drag your feet before this one disappear!!! Welcome to 2320 Tower Ave , Two Car garages ,4 legal bedrooms , 2 full bathrooms single family in quiet cul-de-sac is what you are waiting for is finally here to make it yours, the entire house just came out of renovations from freshly painted , Master Bathroom/Quartz, High Ceiling Family room, New Carpet, New

    Alex Adomako-Acheampong Samson Properties

    2320 Tower Ave, Winchester, VA 22601
  • /3

    $425,000

    • Land
    • 2.53 Acres
    • $167,984 per Acre

    0 N Frederick Pike Unit VAFV2024246, Winchester, VA 22603

    2.5344 Acres, Zoned B-2 General Business Office, Retail, Auto Dealers, Restaurants, Gas Service Stations, Sports (small area in rear is zoned RP) Site was also approved under the old regulations for storm water and is currently grandfathered as long as the current bond is in place. This is a tremendous amount of savingsAccess from North Frederick Pike, Autumn View Lane and Driveway on

    Suzanne Conrad Adams-Nelson & Associates Inc

    0 N Frederick Pike Unit VAFV2024246, Winchester, VA 22603
  • /7

    $499,000

    • Land
    • 18 Acres
    • $27,753 per Acre

    Lot 13 Tavistock Dr, Winchester, VA 22602

    Beautiful 17.98 acre Lot, approved for 3 bedroom perk, Tavistock Estates, one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

    Gillian Greenfield Coldwell Banker Premier

    Lot 13 Tavistock Dr, Winchester, VA 22602
  • /18

    $499,900

    • Land
    • 100 Acres
    • $4,997 per Acre

    100.05 Acres- Shawneeland, Winchester, VA 22602

    From the top of the mountain overlooking the beautiful Shenandoah Valley this 100 acres of pristine wooded property awaits your vision. With spectacular views and total serenity, this raw land has many potentials- it is coded in Agricultural Land Use and is zoned Residential R5 Dist. Currently under a one year lease to a hunting management company (this is definitely a hunters paradise). Must

    Liz Seitz Dandridge Realty Group, LLC

    100.05 Acres- Shawneeland, Winchester, VA 22602
  • /3

    $470,335

    • Land
    • 1.37 Acres
    • $343,310 per Acre

    0 Senseny Rd Unit VAFV2009062, Winchester, VA 22602

    PRICE REDUCED!! Owners are looking for reasonable offers. Lot fronts on Senseny road but can be accessed from the shopping center parking lot. Also can be purchased jointly with Lot H. Lot is flat and ready for development. The house adjoining the lot may also be available for purchase.

    John Coontz Commercial Specialists

    0 Senseny Rd Unit VAFV2009062, Winchester, VA 22602
  • /2

    $500,000

    • Studio
    • 1,175 Sq Ft

    513 and 525 Monticello St, Winchester, VA 22601

    For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

    Brett Haynes Oakcrest Commercial LLC.

    513 and 525 Monticello St, Winchester, VA 22601
  • /24

    $495,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 1,953 Sq Ft

    108 Manasquan Way, Winchester, VA 22602

    The Pine is a popular floorplan for all the right reasons! 4 bedrooms, 2.5 bathrooms, and a 2-car garage. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for seating, an impressive corner pantry, plenty of cabinet space and stainless-steel appliances that

    Brooks Sears DRH Realty Capital, LLC.

    108 Manasquan Way, Winchester, VA 22602
  • /24

    $493,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 1,953 Sq Ft

    110 Manasquan Way, Winchester, VA 22602

    The Pine is a popular floorplan for all the right reasons! 4 bedrooms, 2.5 bathrooms, and a 2-car garage. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for seating, an impressive corner pantry, plenty of cabinet space and stainless-steel appliances that

    Brooks Sears DRH Realty Capital, LLC.

    110 Manasquan Way, Winchester, VA 22602
  • /24

    $493,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 1,953 Sq Ft

    114 Manasquan Way, Winchester, VA 22602

    The Pine is a popular floorplan for all the right reasons! 4 bedrooms, 2.5 bathrooms, and a 2-car garage. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for seating, an impressive corner pantry, plenty of cabinet space and stainless-steel appliances that

    Brooks Sears DRH Realty Capital, LLC.

    114 Manasquan Way, Winchester, VA 22602
  • /20

    $454,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,657 Sq Ft

    111 Yurok Ct, Winchester, VA 22602

    The Cabral offers 1,657 square feet of thoughtfully designed living space, featuring 3 spacious bedrooms, 2.5 bathrooms, and a versatile loft area on the bedroom level—perfect for a home office, playroom, or additional lounge space. Enjoy the convenience of a 2-car garage and modern finishes throughout. This home is move-in ready and comes with added perks including a washer and dryer,

    Brooks Sears DRH Realty Capital, LLC.

    111 Yurok Ct, Winchester, VA 22602
  • /4

    $445,000 New Construction

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

    Lot 1A Lauck Dr, Winchester, VA 22603

    Welcome to this stunning modern cottage/farmhouse, located just 5 minutes from historic downtown Winchester, VA! This beautifully designed home seamlessly blends classic charm with contemporary comfort. This is a pre-planned home, no construction loan necessary.Featuring 3 bedrooms and 2.5 baths, this thoughtfully crafted residence offers an inviting open-concept layout. The main level

    Mary Casselano Dream Real Estate

    Lot 1A Lauck Dr, Winchester, VA 22603
  • /55

    $429,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 1,889 Sq Ft

    169 Munsee Cir, Winchester, VA 22602

    The Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1 car garage. You will love the granite countertops, stainless steel appliances, and recessed lighting in the kitchen. Create the 4th bedroom of your dreams in the lower level bonus space! Other highlights include: Spacious 9 ft ceilings on the main level, over-sized kitchen island, upgraded cabinets, stainless

    Tracy Jennings DRH Realty Capital, LLC.

    169 Munsee Cir, Winchester, VA 22602
  • /27

    $499,500 New Construction

    • 2 Beds
    • 2 Baths
    • 1,609 Sq Ft

    112 Amberfield Ct, Winchester, VA 22602

    BUILDER CLOSE OUT - NEW PRICING - SAVE OVER $52,000. MOVE IN READY TODAY! $35,335 INCENTIVES INCLUDED IN THE PRICE!!!Abrams Chase, Winchester's premier 55+ Active Adult Subdivision is nearing completion and this is the last home available. THIS HOME HAS OVER $75,000 IN UPGRADES.Ashbrook Homes is an award-winning builder specializing in 55+ active adult one-level, maintenance-free

    Cynthia Butler Samson Properties

    112 Amberfield Ct, Winchester, VA 22602
  • /19

    $457,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,637 Sq Ft

    117 Monacan St, Winchester, VA 22602

    The Cabral is a 1,665-square-foot, two-story home with three bedrooms, 2.5 bathrooms, a loft, and a two-car garage. The open-concept main level features a spacious living room, an eat-in kitchen with stainless steel appliances, a walk-in pantry, and a sliding glass door to the backyard. Upstairs, the owner’s suite boasts a large bedroom, walk-in closet, and luxurious bath, complemented by two

    Tracy Jennings DRH Realty Capital, LLC.

    117 Monacan St, Winchester, VA 22602
  • /32

    $449,900 New Construction

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

    570 Glaize Orchard Rd, Winchester, VA 22603

    I am brand new and done! The lot drops off to the rear for privacy, down to Babbs Run which flows strongly during rainy periods. Walk south along the ridge from the excavated area and the driveway and take a look at the dramatic rock outcroppings, there's a perfect spot for a fire ring and chairs. Private and over 3 wooded UNRESTRICTED acres. Side load garage with garage windows across front.

    Jim Thomson Realty ONE Group Old Towne

    570 Glaize Orchard Rd, Winchester, VA 22603
  • /11

    $499,900 Coming Soon

    • 6 Beds
    • 3 Baths
    • 2,793 Sq Ft

    811 Berryville Ave, Winchester, VA 22601

    DO YOU HAVE A LARGE FAMILY AND NEED YOUR OWN SPACE. HERE IS 6 BEDROOMS 3 BATHROOMS WITH 3 FULL KITCHENS. ALMOST 2800 SQ. FT FINISHED. OFF STREET PARKING FOR 6 CARS. SHED AND STILL ROOM TO RELAX OUTBACK. MORE PICS COMING SOON.

    Richard Kozlowski Long & Foster Real Estate, Inc.

    811 Berryville Ave, Winchester, VA 22601
  • /8

    $475,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,309 Sq Ft

    319 Walker St, Winchester, VA 22601

    Coming Soon in Desirable Whittier Acres!This charming 4-bedroom, 2.5-bath Colonial is located just a few blocks from thriving downtown Winchester. Featuring a fantastic floorplan, a bright and inviting sunroom, and a beautifully landscaped yard, this home offers great curb appeal and endless potential. While it awaits your personal updates, its solid layout and prime location in a

    Tiffany Hunter ERA Oakcrest Realty, Inc.

    319 Walker St, Winchester, VA 22601
  • /4

    $445,000 New Construction

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

    Lot 1B Lauck Dr, Winchester, VA 22603

    Welcome to this stunning modern cottage/farmhouse, located just 5 minutes from historic downtown Winchester, VA! This beautifully designed home seamlessly blends classic charm with contemporary comfort. This is a pre-planned home, no construction loan necessary.Featuring 3 bedrooms and 2.5 baths, this thoughtfully crafted residence offers an inviting open-concept layout. The main level

    Mary Casselano Dream Real Estate

    Lot 1B Lauck Dr, Winchester, VA 22603

Home Trends in Winchester, VA

Home Trends

Median Price (12 Mo)
$404,950
Median Single Family Price
$422,750
Median Townhouse Price
$366,990
Median 2 Bedroom Price
$235,000
Median 1 Bedroom Price
$225,000
Average Price Per Sq Ft
$206
Number of Homes for Sale
168
Last 12 months Home Sales
1,030
Months of Supply
2.00
Median List Price
$409,995
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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