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Winchester County VA Homes for Sale with Basement

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  • /2

    $349,900 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,890 Sq Ft

    113 Christopher Dr, Winchester, VA 22601

    Meticulously maintained 3 bedroom, 1.5 bath home in a convenient in-town Winchester location! This home shows beautifully and features hardwood floors that add warmth and character throughout the main living areas. Spacious bedrooms and updates made over the years make this home functional and livable, while still providing an opportunity to personalize as desired. The partially finished basement

    Agent Photo

    Bradley Comstock

    ERA Oakcrest Realty, Inc.

    (540) 318-0527

    113 Christopher Dr, Winchester, VA 22601
  • /65

    $389,990

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

    317 Gray Ave, Winchester, VA 22601

    Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully

    Agent Photo

    Matthew Abregu

    Keller Williams Realty

    (540) 701-3590

    317 Gray Ave, Winchester, VA 22601
  • /20

    $250,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft

    514 Cather Ave, Winchester, VA 22601

    Welcome to this beautifully maintained home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today’s lifestyle. Step inside to a spacious main level featuring a bright and inviting family room, a dedicated dining area, and an eat-in kitchen—perfect for everyday living and entertaining. This home offers

    Agent Photo

    Paula Keiper

    EXP Realty, LLC

    (540) 452-9510

    514 Cather Ave, Winchester, VA 22601
  • /2

    $295,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    704 Watson Ave, Winchester, VA 22601

    Beautifully Maintained Bungalow in a Prime Location! This very well-kept home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for a

    Agent Photo

    Carlos Soares

    Samson Properties

    (540) 530-4023

    704 Watson Ave, Winchester, VA 22601
  • /22

    $949,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,546 Sq Ft

    0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602

    TO BE BUILT: Fauver and Browning Homes proudly presents The Tremont House—a masterfully designed modern residence that blurs the line between architecture and nature. Thoughtfully crafted to harmonize with its surroundings, this home offers a calm, refined living experience. Tucked at the end of a private cul-de-sac in desirable Fairway Estates, overlooking Winchester Country Club, the design

    Agent Photo

    Jeanne Mezzatesta

    Colony Realty

    (540) 698-4119

    0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602
  • /30

    $389,990 New Construction

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

    221 Monteith Dr, Winchester, VA 22601

    END UNIT Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available!***OFFERING UP TO $12K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*MOVE-IN READY! Explore Winchester’s new luxury

    Brittany Newman DRB Group Realty, LLC

    221 Monteith Dr, Winchester, VA 22601
  • /24

    $379,990 New Construction

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

    218 Monteith Dr, Winchester, VA 22601

    END UNIT Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available!***OFFERING UP TO $12K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*MOVE-IN READY! Explore Winchester’s new luxury

    Brittany Newman DRB Group Realty, LLC

    218 Monteith Dr, Winchester, VA 22601
  • /30

    $369,990 New Construction

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

    213 Monteith Dr, Winchester, VA 22601

    Luxury 3 level/3 bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available!***OFFERING UP TO $12K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*MOVE-IN READY! Explore Winchester’s new luxury townhome

    Brittany Newman DRB Group Realty, LLC

    213 Monteith Dr, Winchester, VA 22601
  • /17

    $339,000 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,699 Sq Ft

    2956 Grace St, Winchester, VA 22601

    Welcome to 2956 Grace Street — a 3-bedroom, 1-bath ranch-style home offering comfortable single-level living in Winchester, where a simple, functional layout and everyday ease come together. Inside, the home opens to a light-filled living area with hardwood floors that add warmth and character, creating a comfortable place to gather or unwind at the end of the day. The kitchen offers workspace

    Carolyn Young Samson Properties

    2956 Grace St, Winchester, VA 22601
  • /67

    $375,000

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

    707 E Cork St, Winchester, VA 22601

    Make an offer! 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,

    Misty Weaver Samson Properties

    707 E Cork St, Winchester, VA 22601
  • /37

    $430,000

    • 4 Beds
    • 2 Baths
    • 2,100 Sq Ft

    17 E Leicester St, Winchester, VA 22601

    LOWER INTEREST RATE FOR YOU.....Sellers are offering you 2 percent of sales price so you can buy down your interest rate with an initial 2/1 interest rate buydown OR use the 2% seller concession for your closing costs on this classic brick “American Foursquare” house in Winchester’s historic district. This very well maintained 1928 home was designed and built by “ole time” craftsmen who had an

    Roger Lamborne MarketPlace REALTY

    17 E Leicester St, Winchester, VA 22601
  • /2

    $400,000 Coming Soon

    • 5 Beds
    • 2 Baths
    • 1,011 Sq Ft

    605 Dunlap St, Winchester, VA 22601

    Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-bathroom home offers both seclusion and incredible proximity to Winchester's finest amenities, schools, shopping, and major commuter routes. This residence has been completely reimagined, blending the enduring strength, high-end modern finishes. The moment you enter, you are greeted by the seamless flow of

    Alexandra Brown Spring Hill Real Estate, LLC.

    605 Dunlap St, Winchester, VA 22601
  • /56

    $439,000

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft

    743 Berryville Ave, Winchester, VA 22601

    Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot.The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to

    Sineenat Sirimas Pearson Smith Realty, LLC

    743 Berryville Ave, Winchester, VA 22601
  • /58

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 2,909 Sq Ft

    328 Sheridan Ave, Winchester, VA 22601

    Timeless charm meets thoughtful updates in this beautifully maintained all-brick 1958 home, offering effortless one-level living with a warm retro vibe. Freshly painted throughout and enhanced with new quartz countertops, classic subway tile backsplash, updated sink and faucet, and stylish new lighting, this home blends character with modern comfort. The main level is inviting and functional,

    Mary Casselano Dream Real Estate

    328 Sheridan Ave, Winchester, VA 22601
  • /46

    $449,000

    • 3 Beds
    • 2.5 Baths
    • 1,904 Sq Ft

    25 W Southwerk St, Winchester, VA 22601

    Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers the perfect balance of neighborhood tranquility and

    Dan Whitacre Colony Realty

    25 W Southwerk St, Winchester, VA 22601
  • /97

    $1,200,000

    • 6 Beds
    • 5 Baths
    • 6,682 Sq Ft

    217 W Boscawen St, Winchester, VA 22601

    Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and

    Gillian Greenfield Coldwell Banker Premier

    217 W Boscawen St, Winchester, VA 22601
  • /55

    $585,000

    • 3 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    308 Ridge Ave, Winchester, VA 22601

    Charming all-brick ranch offering comfortable one-level living in a highly convenient location! This well-maintained home features 3 bedrooms and 2 baths on the main level, along with a spacious living room highlighted by a cozy fireplace. A formal dining room provides the perfect space for entertaining, while the kitchen offers ample workspace and connects conveniently to the main-level laundry

    John Scully Colony Realty

    308 Ridge Ave, Winchester, VA 22601
  • /45

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 2,293 Sq Ft

    3137 Eton Place, Winchester, VA 22601

    Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for

    Laura White ERA Oakcrest Realty, Inc.

    3137 Eton Place, Winchester, VA 22601
  • /32

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    3138 Eton Place, Winchester, VA 22601

    Beautiful, just like brand new, 3 bedroom 2.5 bath end unit townhome located in The Lofts at Creekside! Walking distance to local restaurants and shopping here in Creekside. Home features large kitchen island, stainless steel appliances, and luxury vinyl plank flooring, private balcony, surrounded by open floor plan which provides for great entertainment. Nice upgrades all throughout the house!

    Christopher Hild Realty FC, LLC

    3138 Eton Place, Winchester, VA 22601
  • /28

    $360,000

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    101 Molden Dr, Winchester, VA 22601

    This 1963 brick ranch is conveniently located off Pleasant Valley Road in Eastview Subdivision and has been the home to one family. Beautiful hardwood floors throughout the main level, and two fireplaces, one on the main level and one in the finished recreation room on the lower level. Most of the windows throughout the home have also been replaced. Oversized two car garage. Roof was replaced in

    Elizabeth Page Boxwell MarketPlace REALTY

    101 Molden Dr, Winchester, VA 22601
  • /2

    $619,900 Coming Soon

    • 4 Beds
    • 3 Baths
    • 3,336 Sq Ft

    329 Wood Ave, Winchester, VA 22601

    Offering charm and character blended with modern conveniences in the heart of Winchester.Located in the lovely neighborhood of Whittier Acres, this home has been professionally redesigned with flexibility in mind... so you can call this "home" for years to come. Our main level is fitted with two bedrooms and two baths, in addition to a formal living room and an open concept

    Amy Capitano MarketPlace REALTY

    329 Wood Ave, Winchester, VA 22601
  • /30

    $389,990 New Construction

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

    201 Monteith Dr, Winchester, VA 22601

    END UNIT Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! Possibility of 4th Bedroom/flex base in the basement available! ***OFFERING UP TO $12K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*MOVE-IN READY! Explore Winchester’s new luxury

    Brittany Newman DRB Group Realty, LLC

    201 Monteith Dr, Winchester, VA 22601
  • /47

    $985,000

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

    1020 Breckinridge Ln, Winchester, VA 22601

    This property exudes luxury multigenerational living in Meadowbranch! • Main level bedroom + bath• 6500 sq ft• Wet bar in primary suite• 3-car garage• No HOA• Backing to trees, and more..... Approximately 6,500 finished square feet of living space! A place to grow, gather, and stay awhile! A brick-paved, rocking chair-worthy, front porch sets the tone, and the charming side

    Sheila Pack RE/MAX Roots

    1020 Breckinridge Ln, Winchester, VA 22601
  • /22

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,204 Sq Ft

    625 Watson Ave, Winchester, VA 22601

    Nestled in Orchard Terrace, this beautifully updated Colonial home is ideally located within Winchester city limits, just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen features new cabinets, granite countertops, stainless steel appliances, a new sink and faucet, and vinyl plank flooring. The bathroom includes a new vanity, vanity

    Jennifer Sacco RE/MAX Roots

    625 Watson Ave, Winchester, VA 22601
  • /61

    $459,000 Open Sat 1PM - 3PM

    • 6 Beds
    • 3 Baths
    • 1,552 Sq Ft

    2250 Roosevelt Blvd, Winchester, VA 22601

    Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

    Heloisa Amar Samson Properties

    2250 Roosevelt Blvd, Winchester, VA 22601
  • /11

    $525,000 Coming Soon

    • 4 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    823 Woodland Ave, Winchester, VA 22601

    Beautifully renovated 3-level home featuring new hardwood flooring throughout with no transitions for seamless flow and easy mobility. The entire property has been thoughtfully updated while preserving its original charm, including solid wood interior doors. Modern upgrades include new appliances, a main-level accessible restroom, and a stylish kitchen with a contemporary sink, built-in

    Lenora Zaccur Coldwell Banker Realty

    823 Woodland Ave, Winchester, VA 22601
  • /46

    $579,900

    • 4 Beds
    • 2 Baths
    • 2,837 Sq Ft

    1317 Caroline St, Winchester, VA 22601

    Welcome to 1317 Caroline Street, a well-appointed brick rancher in a fantastic Winchester location that perfectly balances professional convenience with residential comfort. Situated just minutes from Winchester Medical Center and major commuter routes, this home offers an effortless transition from a busy day to a relaxing evening. This sense of ease begins the moment you step inside the main

    Dan Whitacre Colony Realty

    1317 Caroline St, Winchester, VA 22601
  • /63

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,999 Sq Ft

    520 N Braddock St, Winchester, VA 22601

    Welcome to this charming home in the heart of Winchester offering character, natural light, and a highly walkable location.This home features 3 bedrooms and 2 full bathrooms, with all bedrooms located on the upper level. At the top of the stairs you’ll find a spacious primary bedroom filled with natural light, creating a bright and inviting retreat. Large windows throughout the home allow

    Angela Duncan MarketPlace REALTY

    520 N Braddock St, Winchester, VA 22601
  • /45

    $500,000

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

    2643 Middle Rd, Winchester, VA 22601

    Location Location Location! NO HOA!!! Hardwood floors on the main level. Formal living and dining room leads to the Family room with stone fireplace, breakfast nook and kitchen. Step out on to the deck to enjoy the views. Large fenced level backyard. Large Primary suite with sitting room and luxury bath. Good sized bedrooms, one with an attached bath. Lower level leads to a patio and backyard.

    Lorraine Arora Berkshire Hathaway HomeServices PenFed Realty

    2643 Middle Rd, Winchester, VA 22601
  • /85

    $625,000

    • 3 Beds
    • 3 Baths
    • 2,722 Sq Ft

    130 Morgan St, Winchester, VA 22601

    Location, Location, Location! 2700 + Finished Sq. Ft. Quality Brick Home Meticulously Maintained with many upgrades! Sitting on a large 12253 Sq. Ft. Lot. Prime Location Two Blocks to Handley Library, Three Blocks to Old Town Walking Mall and Walking Distance to Handley High School, Walking Trails and Summer Concerts at The Museum of the Shenandoah Valley. Low Maintenance Home with Privacy,

    George Johnson Jim Barb Realty Inc.

    130 Morgan 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 both

    Danielle Spriggs Real Broker LLC

    1400 Valley Ave, Winchester, VA 22601
  • /73

    $650,000

    • 4 Beds
    • 3.5 Baths
    • 3,474 Sq Ft

    132 Amherst St, Winchester, VA 22601

    Charming Victorian home in the heart of Winchester’s historic downtown, move-in ready and ideally located just off the Shenandoah Apple Blossom Festival parade route. Rich in character, the foyer, front staircase, living, dining, family room, and main-level bedroom showcase beautiful wood flooring reminiscent of a bygone era. The inviting living room features a bay window and decorative

    Darcy Amburn Colony Realty

    132 Amherst St, Winchester, VA 22601
  • /62

    $884,000

    • 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
  • /45

    $479,900 Open Sat 11:30AM - 1:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,992 Sq Ft

    703 S Loudoun St, Winchester, VA 22601

    Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Check. Endless possibilities? Check!!! This amazing property, located within the Historic Winchester District, presents a one-of-a-kind opportunity to own a piece of history - all just minutes from the Old Town mall. The front of the main home dates back to 1856! You will surely fall in love with the wood

    Kristin Crosby Samson Properties

    703 S Loudoun St, Winchester, VA 22601
  • /17

    $389,990 New Construction

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

    TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601

    ***OFFERING UP TO $12K 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
  • /29

    $269,900

    • 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
  • /8

    $685,000

    • 4 Beds
    • 2.5 Baths
    • 3,108 Sq Ft

    1950 Melvor Ln, Winchester, VA 22601

    Step into this meticulously maintained colonial home, a testament to quality craftsmanship and thoughtful design by Richmond American Homes. Situated in the desirable Meadow Branch South neighborhood, this residence offers an exceptional living experience with a perfect balance of formal and casual spaces This home is situated in a vibrant community with easy access to major roads, shopping, and

    Kim Kroner Washington Dulles Real Estate Group

    1950 Melvor Ln, Winchester, VA 22601
  • /36

    $429,000

    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft

    209 Wood Ave, Winchester, VA 22601

    Welcome to this beautifully-updated brick rancher, a masterclass in blending timeless character with high-end, modern sophistication. From the moment you arrive, the covered front porch and classic silhouette command attention, offering undeniable curb appeal in one of Winchester’s most sought-after locations. Step inside to find a main level bathed in natural light, showcasing gleaming hardwood

    Dan Whitacre Colony Realty

    209 Wood Ave, Winchester, VA 22601
  • /60

    $735,000

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

    1419 Ramseur Ln, Winchester, VA 22601

    This property is NOT in a 55+ community. A rare opportunity for one-level living with over 3,400 finished sq ft in Early’s Green at Meadowbranch. This 4 bedroom, 3 bath brick-front rancher offers a fully finished basement with a custom built bar, a chef’s kitchen, and major upgrades including a Generac whole-house generator and new HVAC (2024). The finished lower level functions as an ideal guest

    Sheila Pack RE/MAX Roots

    1419 Ramseur Ln, Winchester, VA 22601
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