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Winchester County VA Homes for Sale

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  • /88

    $435,000

    • Studio
    • 2,152 Sq Ft

    26 A Jackson Ave, Winchester, VA 22601

    Rare Opportunity: Turnkey Duplex in Winchester – Vacant, Updated, and Ready for Your Next Move! A rare and an exceptional opportunity to own a two-unit duplex in Winchester City— vacant and ready for your plans. Whether you’re an investor seeking strong cash flow or an owner-occupant looking to live in one unit and rent the other, this property offers flexibility, income potential, and low

    Agent Photo

    Melanie Lucero

    Real Broker, LLC

    (540) 386-1285

    26 A Jackson Ave, Winchester, VA 22601
  • /72

    $699,900

    • 4 Beds
    • 3.5 Baths
    • 3,475 Sq Ft

    132 Amherst St, Winchester, VA 22601

    Price Improvement to make this Yours! Step back in time with this Beautifully preserved VICTORIAN Brick Home Built in 1880, a true piece of Winchester's history. This is a Registered Historic Property that showcases original architectural details, high ceilings, ornate trim, and original wood floors that reflect the artistry of a bygone era. A Well Designed Addition has allowed for generous space

    Jodi Costello ERA Oakcrest Realty, Inc.

    132 Amherst St, Winchester, VA 22601
  • /115

    $499,999

    • 5 Beds
    • 3 Baths
    • 2,080 Sq Ft

    419 Summit Ave, Winchester, VA 22601

    Welcome Home!This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment.With 5

    Waqas Abbasi Lifestyle Realty, LLC.

    419 Summit Ave, Winchester, VA 22601
  • /67

    $399,999

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

    707 E Cork St, Winchester, VA 22601

    Don't let this location fool you - Plenty of parking on the side and back of the home and a large turn around space to exit onto Cork St easily! Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access to Jim Barnett Park just down the street, downtown walking mall and commuter roads, and even views

    Misty Weaver Samson Properties

    707 E Cork St, Winchester, VA 22601
  • /43

    $490,000

    • 3 Beds
    • 4 Baths
    • 3,359 Sq Ft

    227 Miller St, Winchester, VA 22601

    Welcome to 227 Miller Street — a home that instantly feels inviting. The front porch sets the tone, offering a perfect spot for quiet mornings in the heart of downtown Winchester. Inside, the main level has an easy flow: a bright living room, a dining space ready for gatherings, and a sun-filled enclosed sunroom that naturally becomes a favorite place to slow down. The kitchen has all new

    Leah Marabella Realty ONE Group Old Towne

    227 Miller St, Winchester, VA 22601
  • /24

    $389,990 New Construction

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

    210 Monteith Dr, Winchester, VA 22601

    OPEN HOUSE: Saturday - Sunday 1pm - 3pm Beautiful open concept living 3 level townhome with Lower Level Walkout! The Bedford II 3 level interior town home with a box bay window with 1 car garage featuring 3 Bedrooms and 3.5 Baths and 1,784 square feet. It is fully finished top to bottom. The front door with the electronic Ring door camera leads directly into the spacious lower-level recreation

    DRB Homes Builder
    210 Monteith Dr, Winchester, VA 22601
  • /55

    $659,000

    • 5 Beds
    • 2.5 Baths
    • 3,420 Sq Ft

    501 Jefferson St, Winchester, VA 22601

    Welcome Home!If you’ve been searching for an updated home in a prime location, this is it! This stunning 5BR/3BA property has been completely renovated from top to bottom—and it shows. Step inside to an open floor plan where natural light fills the gorgeous kitchen, featuring quartz countertops, stainless steel appliances, and plenty of space to gather. The adjoining family room opens to a

    Agent Photo

    Jeanne Mezzatesta

    Colony Realty

    (540) 306-5775

    501 Jefferson St, Winchester, VA 22601
  • /29

    $289,900

    • 2 Beds
    • 1 Bath
    • 870 Sq Ft

    1125 Conway St, Winchester, VA 22601

    Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of

    Jodi Costello ERA Oakcrest Realty, Inc.

    1125 Conway St, Winchester, VA 22601
  • /20

    $323,000

    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    553 Highland Ave, Winchester, VA 22601

    MOTIVATED SELLER - price reduction of $11,000 - bring all offers! One Way street = quiet Gorgeous Rehab - you have to see it! Secure Parking off the alley Efficient HVAC mini splits installed Washer and Dryer included

    Teri Domanski Corcoran McEnearney

    553 Highland Ave, Winchester, VA 22601
  • /55

    $685,000

    • 5 Beds
    • 4 Baths
    • 4,576 Sq Ft

    800 Lake Dr, Winchester, VA 22601

    Location Location Location! Welcome to 800 Lake Dr. Winchester VA 22601, Located in the highly sought-after Rolling Hills community and situated on a 0.37 acre lot, This expansive home offers 4,500+ sqft. of living space, featuring 5 bedrooms, 4 Full baths, finished basement, and 2 car garage! Step inside to find gleaming hardwood floors in the formal living and dining rooms. The unique

    Lisa Behr Coldwell Banker Premier

    800 Lake Dr, Winchester, VA 22601
  • /41

    $355,000

    • 4 Beds
    • 2.5 Baths
    • 2,804 Sq Ft

    513 van Fossen St, Winchester, VA 22601

    Welcome to 513 Van Fossen St, a beautifully updated 4-bedroom, 2.5-bathroom brick ranch conveniently located just minutes from downtown Winchester. Step inside to discover freshly refinished original red oak hardwood floors (locally sourced from Plumly Lumber) in a warm Golden Pecan finish (2025). The home boasts fresh paint inside and out, a brand-new roof (2025), and newer HVAC. The living room

    Amy Longerbeam RE/MAX Roots

    513 van Fossen St, Winchester, VA 22601
  • /72

    $494,900

    • 5 Beds
    • 3.5 Baths
    • 3,330 Sq Ft

    118 Russelcroft Rd, Winchester, VA 22601

    Tina Jacobin Main Street Realty

    118 Russelcroft Rd, Winchester, VA 22601
  • /42

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,426 Sq Ft

    715 Berryville Ave, Winchester, VA 22601

    This renovated jewel on the east side of Winchester is ready for you! Enjoy the new modern kitchen, new tile bathrooms, updated HVAC and electrical, fresh paint, refinished floors, and more! Plus, this home is full of character you don't find in new homes. Look close! From unique windows to original molding and solid interior doors, you'll find unexpected charm everywhere. Between the unfinished

    William Steinmetz RE/MAX Roots

    715 Berryville Ave, Winchester, VA 22601
  • /43

    $459,000

    • 3 Beds
    • 2 Baths
    • 2,648 Sq Ft

    1332 Ramseur Ln, Winchester, VA 22601

    Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exterior condo offering 3 bedrooms and 2 full baths. Rich hardwood floors flow throughout the home. The primary bedroom includes a cozy fireplace perfect for relaxing evenings. Updated appliances, such as washer, dryer, refrigerator, stove and microwave. Enjoy the ease of your own private elevator within the

    James King RE/MAX Roots

    1332 Ramseur Ln, Winchester, VA 22601
  • /14

    $1,499,000

    • Land
    • 2 Acres
    • $749,500 per Acre

    1625 Amherst St, Winchester, VA 22601

    Introducing a fantastic development opportunity! This parcel features 2 flat acres of commercial land in a prime location. Located on a major thoroughfare into downtown Winchester and a half mile from Winchester Medical Center, this lot is ideal for your commercial venture. The lot offers excellent road frontage and good topography. Ideal for medical/dental office, office space, restaurant, or

    Dan Whitacre Colony Realty

    1625 Amherst St, Winchester, VA 22601
  • /14

    $441,700

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    421 Superior Ave, Winchester, VA 22601

    Renovated and move in ready! Let's start with the new mailbox, new 16' wide asphalt driveway, new 8'x13' concrete patio for you to enjoy watching the sun sets overlooking the large back yard., The carport even has bolts in ceiling for you to install a swing. Then inside, new heat pump and central a/c system, new appliances with fingerprint resistant stainless-steel exterior, stainless steel liner

    Leo Smith CENTURY 21 New Millennium

    421 Superior Ave, Winchester, VA 22601
  • /42

    $449,900

    • 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
  • /38

    $449,990 New Construction

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

    1819 Reese Ct, Winchester, VA 22601

    1819 Reese Court is a move-in ready 3-level townhome with full brick front in Winchester, VA. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP flooring. The kitchen is equipped with beautiful quartz countertops, sasparilla cabinets, and stainless-steel appliances. The upper

    D.R. Horton Builder
    1819 Reese Ct, Winchester, VA 22601
  • /19

    $299,500

    • 3 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    106 W Southwerk St, Winchester, VA 22601

    Charming 3 bedroom, 1.5 bath colonial just blocks from downtown Winchester! Enjoy a covered front porch perfect for relaxing and a spacious rear deck for entertaining. Inside, you’ll find inviting spaces with newer windows throughout. Conveniently located near shopping, restaurants, entertainment, the local library, and Jim Barnett Park—this home offers both comfort and an unbeatable location!

    Sheila Pack RE/MAX Roots

    106 W Southwerk St, Winchester, VA 22601
  • /31

    $344,900

    • 4 Beds
    • 2 Baths
    • 915 Sq Ft

    414 Elm St, Winchester, VA 22601

    Completely renovated four-bedroom, two-bath home in Winchester. Upgraded kitchen with new 42-inch cabinets, quartz countertops, and brand new appliances. Tastefully painted, new windows, new flooring, new HVAC, upgraded electric fixtures, and plumbing. Totally remodeled bathrooms. Very spacious walkout basement with a bedroom and bath. Huge flat backyard with a stone patio.Excellent commuter

    Aracely Rivera First Decision Realty LLC

    414 Elm St, Winchester, VA 22601
  • /53

    $654,000

    • Studio
    • 3,511 Sq Ft

    1400 Valley Ave, Winchester, VA 22601

    Versatile on Valley!So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out

    Danielle Spriggs Real Broker LLC

    1400 Valley Ave, Winchester, VA 22601
  • /3

    $2,300,000

    • Land
    • 3.51 Acres
    • $655,271 per Acre

    1721 Amherst St, Winchester, VA 22601

    3.51 AC of premier commercial land. Directly across the street from the main hospital campus on one of Winchester's main commercial corridors. Ideal for banks, medical offices, retail or restaurants.

    Marie DiLorenzo Oakcrest Commercial LLC.

    1721 Amherst St, Winchester, VA 22601
  • /17

    $389,990

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

    TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601

    ***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*Featuring Bedford II in Valor Crossing! Open concept kitchen located next to the country kitchen and living room. Optional features include box bay rear window and 10' x 14' deck. Primary suite with large

    Brittany Newman DRB Group Realty, LLC

    TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601
  • /11

    $1,100,000

    • Land
    • 2.83 Acres
    • $388,693 per Acre

    2725 S Pleasant Valley Rd, Winchester, VA 22601

    Location, location, location. Here is your chance to own one of the few commercial/industrial lots located in the highly desirable Winchester City. This cleared, blank slate is ready for your next business endeavor. Currently zoned as CM-1 (Commercial/Industrial), the property offers roughly 465 ft of prime road frontage, perfect for displaying your establishment.Current use regulations

    Kaitlyn Behr RE/MAX Roots

    2725 S Pleasant Valley Rd, Winchester, VA 22601
  • /20

    $449,900

    • Studio
    • 2,376 Sq Ft

    510 N Loudoun St, Winchester, VA 22601

    All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD/1BA with unfinished attic, main floor is 1BR/1BA (Both have rear balcony) and basement unit has access to storage area and includes1BD/1BA. All units have washer/dryer (Basement unit washer/dryer belongs to tenant). Owner/Agent and home inspection report available upon request.

    Dave Spence RE/MAX Roots

    510 N Loudoun St, Winchester, VA 22601
  • /13

    $349,999

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

    505 Green St, Winchester, VA 22601

    BACK ON THE MARKET DUE TO BUYER FINANCING AND NON PERFORMANCE. Charming 3-Level Split Home in the Heart of Winchester! This split level home could be your forever home! Surrounded by parks, top-rated schools, and everyday amenities. Quick access to Route 7 and Interstate 81 commuting is breeze! Upstairs, you’ll find three generously sized bedrooms and a full bathroom, offering a peaceful seperate

    Julissa Rodriguez Vaze Realty

    505 Green St, Winchester, VA 22601
  • /33

    $459,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 1,905 Sq Ft

    Adams II Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

    The Adams II townhome features 1,905 sq. ft. of stylish and flexible living space, including 4 bedrooms, 3.5 bathrooms, and a 1-car rear-load garage. The gourmet kitchen is equipped with quartz countertops, stainless steel appliances, recessed lighting, a generous island, and sleek Duraform cabinetry. The lower-level bonus room offers endless possibilities—use it as a rec room, home office, or an

    D.R. Horton Builder
    1831 Reese Ct Unit 37025141, Winchester, VA 22601
  • /38

    $409,990 New Construction

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

    Adams Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

    The Adams I townhome offers 1,889 sq. ft. of thoughtfully designed living space, featuring 4 bedrooms, 3.5 bathrooms, and a convenient 1-car front-load garage. The modern kitchen showcases quartz countertops, stainless steel appliances, a spacious island, recessed lighting, and upgraded cabinets. Enjoy the flexibility of a finished lower-level bonus space—perfect for a rec room, home office, or

    D.R. Horton Builder
    1831 Reese Ct Unit 37025140, Winchester, VA 22601
  • /19

    $225,000

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft

    369 Charles St, Winchester, VA 22601

    This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two

    Marisa Varley ERA Oakcrest Realty, Inc.

    369 Charles St, Winchester, VA 22601
  • /143

    $899,000

    • 5 Beds
    • 4.5 Baths
    • 4,438 Sq Ft

    769 Seldon Dr, Winchester, VA 22601

    Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along

    Amanda Slate Keller Williams Realty

    769 Seldon Dr, Winchester, VA 22601
  • /26

    $344,900

    • 3 Beds
    • 2.5 Baths
    • 1,536 Sq Ft

    1004 S Cameron St, Winchester, VA 22601

    Why squeeze your life into a shoebox condo or townhouse when you could actually stretch out, breathe, and live in this renovated 3-bedroom detached home for just $349K?- -Tucked away on a private 7,840 sq. ft. lot in Winchester, this 1920s charmer gives you the one thing condos and townhouses can’t: freedom. No shared walls, no stairs, and absolutely no HOA telling you what color

    Patricia Salgado Metas Realty Group, LLC

    1004 S Cameron St, Winchester, VA 22601
  • /26

    $389,990 New Construction

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

    Bedford II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

    OPEN HOUSE: Saturday - Sunday 1pm - 3pm 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. Box bay rear window and 10' x 14' Trex deck. 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 Builder
    0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
  • /58

    $999,000

    • 6 Beds
    • 5.5 Baths
    • 6,540 Sq Ft

    1020 Breckinridge Ln, Winchester, VA 22601

    Buy your new home and enjoy a 1% lower interest rate for the first year with a temporary buydown incentive - helping make your first year of homeownership more affordable! Ask for details!Recent Updates include a new roof (2023), attic HVAC serviced/replaced A coil (2024), basement HVAC replaced A Coil & condenser (2021), and a new water softener to be installed (2025) One-owner, custom home,

    Sheila Pack RE/MAX Roots

    1020 Breckinridge Ln, Winchester, VA 22601
  • /32

    $474,500

    • 4 Beds
    • 4 Baths
    • 1,627 Sq Ft

    201 Parkway St, Winchester, VA 22601

    Freshly Renovated Charmer in Winchester! Welcome to 201 Parkway Street, a freshly updated home in the heart of Winchester! Previously tenant-occupied, this property has been thoughtfully refreshed and is ready for new owners. Recent Updates Include: Fresh interior paint throughout Renovated kitchen and bath Updated fixtures and finishes Clean, move-in ready condition This home offers the perfect

    Cherish Green Coldwell Banker Elite

    201 Parkway St, Winchester, VA 22601
  • /37

    $396,500

    • 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, fenced-in

    Meridee Powars Link Realty Services LLC

    31 W Whitlock Ave, Winchester, VA 22601
  • /17

    $235,000

    • Land
    • 0.36 Acre
    • $652,778 per Acre

    506 Fairmont Ave, Winchester, VA 22601

    Introducing a newly configured Winchester City lot ready for you to build your dream home! The heavy lifting has already been done. The current owner worked with the neighbors and the City to widen the lot to accommodate a sizable home. With a width of approximately 100 feet you will have plenty of space to spread out. Located on a storied street in downtown Winchester, you will enjoy the perks

    Dan Whitacre Colony Realty

    506 Fairmont Ave, Winchester, VA 22601
  • /56

    $1,899,000

    • Studio
    • 7,190 Sq Ft

    908 Cedar Creek Grade, Winchester, VA 22601

    In town location for this completely remodeled multi unit property. This property contains 4 homes and 2 apartments that have been completely refinished. The main home is currently lived in by the owner and is attached to a indoor swimming pool. The other 3 homes and 2 apartments are leased and are bringing over$10,500 monthly. If you choose rent the main house income would be much higher. .

    Meridee Powars Link Realty Services LLC

    908 Cedar Creek Grade, Winchester, VA 22601
  • /10

    $549,900

    • Land
    • 0.09 Acre
    • $6,110,000 per Acre

    1 N Braddock St, Winchester, VA 22601

    Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

    Gillian Greenfield Coldwell Banker Premier

    1 N Braddock St, Winchester, VA 22601
  • /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

Showing Results 41 - 79, Page 2 of 2

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