244

Winchester, VA Homes for Sale with Parking

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  • /50

    $669,500

    • 4 Beds
    • 2.5 Baths
    • 2,998 Sq Ft

    441 Fair Ln, Winchester, VA 22603

    Discover your perfect retreat at 441 Fair Ln, Winchester, VA 22603, in the peaceful Fairway Estates neighborhood! This stunning 4-bedroom, 2.5-bathroom single-family home spans 2,998 square feet on a sprawling 5.54-acre lot, offering a blend of modern luxury and serene country living. Built in 2000, this meticulously updated residence is just minutes from Historic Downtown Winchester and major

    Caleb Fowler Samson Properties

    441 Fair Ln, Winchester, VA 22603
  • /64

    $249,500

    • 3 Beds
    • 1 Bath
    • 946 Sq Ft

    208 Opossum Trail, Winchester, VA 22602

    Welcome to this charming two-story home nestled in a peaceful country setting, surrounded by mature trees, vibrant flower beds, and a majestic weeping willow that graces the front yard. The cozy and convenient main-level primary suite features a spacious double-door walk-in closet, and the open floor plan offers the perfect blend of comfort and function—flooded with natural light and ideal for

    Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

    208 Opossum Trail, Winchester, VA 22602
  • /40

    $915,000

    • 5 Beds
    • 6.5 Baths
    • 4,301 Sq Ft

    254 Whistlewood Ln, Winchester, VA 22602

    Situated in the picturesque countryside of Winchester Virginia boasting a modern aesthetic and elevation. Welcome home to 254 Whistlewood Ln! The home is beautifully positioned within the Royal Oaks community on a private 5 acre lot! It benefits from the serenity one would expect from a countryside home and the convenience of a short distance to town, commuter routes and just 15 minutes to

    Stuart Pollard Pearson Smith Realty, LLC

    254 Whistlewood Ln, Winchester, VA 22602
  • /13

    $349,999

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

    505 Green St, Winchester, VA 22601

    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 area. The main level boasts a warm and

    Julissa Rodriguez Vaze Realty

    505 Green St, Winchester, VA 22601
  • /90

    $515,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,984 Sq Ft

    2623 Middle Rd, Winchester, VA 22601

    Welcome home to 2623 Middle Rd! Now with a Virtual Tour of this beautiful home! Located near all that Winchester has to offer, Middle Rd is a lovely private oasis to come home to. With a myriad of upgrades including a gorgeous screened in back porch, this home offers many conveniences, a spacious layout and bedrooms, and plenty of room for entertainment, hobbies, and whatever you can dream of.

    Nicole Lewis Coldwell Banker Premier

    2623 Middle Rd, Winchester, VA 22601
  • /52

    $650,000

    • 6 Beds
    • 3 Baths
    • 2,568 Sq Ft

    1301 Front Royal Pike, Winchester, VA 22602

    UNIQUE AND HISTORIC! UNPACK THE POTENTIAL OF THIS 214-YEAR-OLD SHENANDOAH VALLEY HOME AND TURN IT INTO AN ELEGANT SHOWPLACE! If houses could talk, this one would speak volumes. Built in 1811, during the nation's infancy, it later bore witness to the Civil War in which it was said to have been a hospital. In 1864, it was a division headquarters for George Armstrong Custer. The flat roof

    Teresa Strohmeyer ERA Oakcrest Realty, Inc.

    1301 Front Royal Pike, Winchester, VA 22602
  • /94

    $699,999

    • 6 Beds
    • 3.5 Baths
    • 4,365 Sq Ft

    122 Poe Dr, Winchester, VA 22602

    Welcome to your dream home to own this immaculate 6-Bedroom with amazing Blue Ridge Views. This beautiful home built 2023 has been adorably well cared for and nestled in one of Winchester’s most coveted neighborhoods. This home is the largest model offered by Richmond American Homes – the Yorktown with add-on Sun-Room extension. With 6 spacious bedrooms, 3.5 luxurious bathrooms, and an array of

    Mohammad Bhatti Samson Properties

    122 Poe Dr, Winchester, VA 22602
  • /57

    $455,000

    • 4 Beds
    • 3.5 Baths
    • 1,676 Sq Ft

    125 Alliance Ct, Winchester, VA 22602

    Welcome to this beautifully maintained home in the highly desirable Freedom Manor subdivision in Winchester, VA—ideally located just minutes from shopping, dining, and everyday conveniences. Offering a perfect blend of comfort, functionality, and location, this property is ready to impress.The main level features durable and stylish luxury vinyl plank (LVP) flooring throughout. The living

    Rhonda Shade ERA Oakcrest Realty, Inc.

    125 Alliance Ct, Winchester, VA 22602
  • /25

    $445,000

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

    112 Hites St, Winchester, VA 22602

    No HOA! Discover the expanded comfort of this charming home, featuring a spacious addition completed in 2011. Two master suites: one upstairs and the other one at the main level—it’s ideal for multigenerational living or a private in-law suite. Enjoy a fenced backyard, attached single-car garage, and updates including a newer roof (2015) and HVAC system with heat pump and gas furnace (2011). The

    Rocio Benavides Orus Realty Inc

    112 Hites St, Winchester, VA 22602
  • /52

    $250,000

    • 3 Beds
    • 3 Baths
    • 2,090 Sq Ft

    123 Old Bethel Ln, Winchester, VA 22603

    Welcome to 123 Old Bethel Ln – a spacious manufactured home situated on a beautiful lot that may exceed tax-recorded acreage (survey in progress!). This property has served as a long-time family home and is now ready for a new chapter—offering affordability, space, and potential. The home includes multiple living areas, intact appliances, some updated windows, and a layout that could be renovated

    Fawn Deitsch RE/MAX Gateway

    123 Old Bethel Ln, Winchester, VA 22603
  • /50

    $694,000

    • 4 Beds
    • 3.5 Baths
    • 4,167 Sq Ft

    132 Cahille Dr, Winchester, VA 22602

    Elegant Colonial with Theater Room, Stone Water Features & Luxury Upgrades in Raven Pointe Welcome to your dream home in the highly sought-after Raven Pointe neighborhood! This beautifully maintained 4-bedroom, 3.5-bath colonial, built in 2005, offers nearly 4,000 sq ft of luxurious living space on a serene 0.28-acre lot. Thoughtfully designed for both entertaining and everyday comfort, this home

    Jonathan Minerick Homecoin.com

    132 Cahille Dr, Winchester, VA 22602
  • /91

    $959,000

    • 4 Beds
    • 4.5 Baths
    • 6,566 Sq Ft

    1509 Stone House Ct, Winchester, VA 22601

    Perched on the edge of the walking trail with fall views of the lake, and host to a private oasis in the back yard, you'll find 1509 Stone House Court, one of the largest homes in Morlyn Hills. The current owners added the pool, extensive hardscaping, retainer walls, privacy fence, and a composite deck with angled stairs to the pool area. Marble floors welcome you to a light filled foyer that

    Natalie Langford ERA Oakcrest Realty, Inc.

    1509 Stone House Ct, Winchester, VA 22601
  • /63

    $815,000

    • 4 Beds
    • 3.5 Baths
    • 3,942 Sq Ft

    756 Brookneil Dr, Winchester, VA 22602

    Some homes are lived in. Others are lived for. This one? It's the kind of place you wait for—the kind you watch for, and when it finally hits the market, you clear your calendar to see it.Set deep into over 9 private wooded acres, at the very end of a quiet cul-de-sac, this completely rebuilt ranch-style home in Winchester offers something you rarely find anymore: total privacy, modern

    Alexander Bracke Real Broker, LLC

    756 Brookneil Dr, Winchester, VA 22602
  • /49

    $659,000

    • 4 Beds
    • 2.5 Baths
    • 3,512 Sq Ft

    2321 Stoneridge Rd, Winchester, VA 22601

    Must see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The open foyer invites you into this spacious home boasting over 3500 sq.ft. plus a full walk-out basement, ready to finish for additional square footage. Large living and dining rooms with hardwood, den or office. Large kitchen features granite counters, stainless steel appliances, and a breakfast area that

    John Schroth Colony Realty

    2321 Stoneridge Rd, Winchester, VA 22601
  • /26

    $294,900

    • 3 Beds
    • 1 Bath
    • 1,094 Sq Ft

    143 Dowell J Cir, Winchester, VA 22602

    Charming Rancher with Prime Location and Endless Potential! Seller offering $5,000 towards buyers closing costs or desired upgrades.This well-built, single-level rancher offers 3 bedrooms and 1 full bath across 1,000 square feet of smartly designed living space. Nestled on a quiet street just outside Winchester city limits, this home falls within the Frederick County school

    Sarah Hott hott Realty ONE Group Old Towne

    143 Dowell J Cir, Winchester, VA 22602
  • /51

    $1,195,000

    • 7 Beds
    • 4.5 Baths
    • 6,380 Sq Ft

    207 Westview Dr, Winchester, VA 22603

    Welcome to 207 Westview Drive, a secluded sanctuary nestled on just over six wooded acres in the heart of the Shenandoah Valley—mere minutes from the charm of Historic Old Town Winchester. With over 6,600 square feet of beautifully finished living space, this one-of-a-kind property offers the perfect blend of luxury, comfort, and natural beauty. Tucked deep into the trees, yet close to shops,

    Carolyn Young Samson Properties

    207 Westview Dr, Winchester, VA 22603
  • /143

    $950,000

    • 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,

    Amanda Slate Keller Williams Realty

    769 Seldon Dr, Winchester, VA 22601
  • /72

    $695,000

    • 5 Beds
    • 4 Baths
    • 4,387 Sq Ft

    3949 N Frederick Pike, Winchester, VA 22603

    You will feel the peace and harmony the moment you come up the drive, this is your new home place. Almost 4 unrestricted acres for you to spread your wings. The sweet spots here will truly tug at your heart, the hammock area for lazy day reading, the fire pit with the most incredible mountain views in the fall and winter months, The four wheeler trails begging for fun and memories!! The

    Kristen Kerns Roberts Realty Group, LLC

    3949 N Frederick Pike, Winchester, VA 22603
  • /29

    $409,900

    • 3 Beds
    • 2.5 Baths
    • 1,962 Sq Ft

    117 Tye Ct, Winchester, VA 22602

    Modern, Move-In Ready Townhome with Premium UpgradesIdeally located just outside the bustle of Winchester with an easy commute to the DC Metro area, this 2023-built townhome offers the perfect balance of comfort, convenience, and style.Freshly and professionally painted throughout, the home features an open-concept main level with durable LVP flooring, granite countertops,

    Rick Cockrill Keller Williams Realty

    117 Tye Ct, Winchester, VA 22602
  • /56

    $860,000

    • 5 Beds
    • 4.5 Baths
    • 5,254 Sq Ft

    1504 Brookdale Ct, Winchester, VA 22601

    PRICE IMPROVEMENT!Over 5,250 sq ft in this stunning 5BR/3.5BA Home in Prime Meadow Branch Area!Elegant 2-story foyer with sweeping staircase, coffered ceilings, and extended-height windows. Family room features floor-to-ceiling stone fireplace, open to gourmet kitchen with quartz countertops, stainless steel appliances, cooktop, and wall oven. Main level office with French doors, formal

    Julie Shiley Coldwell Banker Realty

    1504 Brookdale Ct, Winchester, VA 22601
  • /78

    $675,000

    • 5 Beds
    • 4 Baths
    • 4,037 Sq Ft

    114 Renee Ln, Winchester, VA 22602

    Welcome to 114 Renee Lane – Where Elegance Meets Everyday ComfortThis beautifully appointed home offers the perfect blend of space, sophistication, and modern convenience. Boasting 5 bedrooms and 4 full bathrooms, including a main-level bedroom and full bath ideal for guests or multi-generational living, this residence is designed to accommodate today’s lifestyles.Step inside to

    Laura White ERA Oakcrest Realty, Inc.

    114 Renee Ln, Winchester, VA 22602
  • /58

    $1,099,000

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

    1020 Breckinridge Ln, Winchester, VA 22601

    Approximately 6,000 finished square feet of living space! A place to grow, gather, and stay awhile! From the moment you arrive, this property greets you with thoughtful details and a sense of home you can feel. A brick-paved, rocking chair-worthy front porch sets the tone, and the charming side porch with composite decking is both stylish and maintenance-free. This spacious 6+ bedroom/5.5 bath

    Sheila Pack RE/MAX Roots

    1020 Breckinridge Ln, Winchester, VA 22601
  • /49

    $499,870

    • 5 Beds
    • 3 Baths
    • 3,116 Sq Ft

    110 Carter Place, Winchester, VA 22602

    Contract fell through! Extensive Renovations: The home has been fully renovated in 2025, including updates to kitchen, bathrooms, flooring, and fresh paint throughout. Designed to accommodate two families comfortably, featuring large rooms that are flooded with natural light like the entire house. The lower level is equipped with wheelchair-accessible features, enhancing mobility and

    Rodrigo Cruz Long & Foster Real Estate, Inc.

    110 Carter Place, Winchester, VA 22602
  • /40

    $450,000

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

    1709 Reaves St, Winchester, VA 22601

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

    Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

    1709 Reaves St, Winchester, VA 22601
  • /28

    $339,900

    • 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
  • /32

    $244,900

    • 3 Beds
    • 2 Baths
    • 1,070 Sq Ft

    311 Ash Hollow Dr, Winchester, VA 22602

    Opportunity awaits in Ash Hollow Estates! This 3-bedroom, 2-bath townhouse is full of potential—solid bones, a smart layout, and endless possibilities for transformation. Whether you're an investor or a first-time buyer ready to create something special, this home is the perfect canvas. With a little TLC, a fresh new look is on the horizon! New carpet installed as of August 2025 adds a clean,

    Josh Medina ERA Oakcrest Realty, Inc.

    311 Ash Hollow Dr, Winchester, VA 22602
  • /18

    $299,000

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

    711 E Cork St, Winchester, VA 22601

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

    Jim Stafford ERA Oakcrest Realty, Inc.

    711 E Cork St, Winchester, VA 22601
  • /85

    $1,224,000

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

    801 Armistead St, Winchester, VA 22601

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

    Tiffany Hunter ERA Oakcrest Realty, Inc.

    801 Armistead St, Winchester, VA 22601
  • /45

    $439,900

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

    275 Greenwood Rd, Winchester, VA 22602

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

    Jose Ugaz Gates Smart Realty, LLC

    275 Greenwood Rd, Winchester, VA 22602
  • /52

    $300,000

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

    102 Duwamish Trail, Winchester, VA 22602

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

    Dorothy Beach Samson Properties

    102 Duwamish Trail, Winchester, VA 22602
  • /27

    $339,000

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

    425 Beechcroft Rd, Winchester, VA 22601

    Open House Saturday 16th only. 1-3. One level living in a sturdy, large (over 2000+/- SF) brick rancher close to all amenities? Restaurants and stores all within a couple of miles including Jim Barnett Park. Easy access to major commuter routes. Relax on the huge front porch or rear covered patio in the private, fully fenced backyard. Semi-open floor plan in the main area bracket the kitchen

    Laurel Murray Samson Properties

    425 Beechcroft Rd, Winchester, VA 22601
  • /62

    $749,000

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

    1877 Clayton Ridge Dr, Winchester, VA 22601

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

    Dave Spence RE/MAX Roots

    1877 Clayton Ridge Dr, Winchester, VA 22601
  • /22

    $317,500

    • 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 McKenzie Realty ONE Group Old Towne

    102 Zephyr Ln, Winchester, VA 22602
  • /69

    $435,000

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

    1793 N Hayfield Rd, Winchester, VA 22603

    Charming all-brick ranch home on a spacious .97-acre lot, featuring 3 bedrooms, 2.5 baths, and traditional style throughout. Enjoy a covered front porch, rear deck, living room with fireplace, separate dining room, and eat-in kitchen. Includes a 2-car garage and no HOA. Ideally located—peaceful setting just outside of town, yet only 10 minutes to shopping and Winchester Medical Center, and just

    RoxAnn Grimes RE/MAX Roots

    1793 N Hayfield Rd, Winchester, VA 22603
  • /47

    $450,000

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

    164 Bethel Grange Rd, Winchester, VA 22603

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

    Cathy Durbin Crum Realty, Inc.

    164 Bethel Grange Rd, Winchester, VA 22603
  • /56

    $899,000

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

    442 Frog Hollow Rd, Winchester, VA 22603

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

    Wendy Conner Coldwell Banker Premier

    442 Frog Hollow Rd, Winchester, VA 22603
  • /54

    $724,900

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

    1419 Ramseur Ln, Winchester, VA 22601

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

    Sheila Pack RE/MAX Roots

    1419 Ramseur Ln, Winchester, VA 22601
  • /28

    $475,000

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

    386 Round Hill Rd, Winchester, VA 22602

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

    Bridget Aikens Colony Realty

    386 Round Hill Rd, Winchester, VA 22602
  • /42

    $769,900

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

    1049 Laurel Grove Rd, Winchester, VA 22602

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

    LESLIE WEBB Long & Foster Real Estate, Inc.

    1049 Laurel Grove Rd, Winchester, VA 22602
  • /41

    $310,000

    • 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

Showing Results 81 - 120, Page 3 of 7

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