377

Winchester, VA Homes for Sale

Section Image
  • /38

    $355,000

    • 3 Beds
    • 3 Baths
    • 2,668 Sq Ft

    109 Arrowhead Trail, Winchester, VA 22602

    Have you been waiting for the perfect home in Shawneeland? Look no further. This fantastic split-foyer has been recently renovated and is ready for you! Upgrades include a brand new asphalt shingle roof, new vinyl plank flooring throughout, fresh paint, and a total overhaul of the laundry room. The home boasts three spacious bedrooms, a large family room, an enormous basement rec room, and two

    Kristin Crosby Samson Properties

    109 Arrowhead Trail, Winchester, VA 22602
  • /33

    $379,999

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    107 Fay St, Winchester, VA 22602

    This beauty will be available mid august or earlier has exceptional renovation and superb location off Rt.11 and great proximity to I-81/Rt.37 corridor. They have done all the big ticket items like installing a new roof, upgrading the baths, BRAND NEW WINDOWS (we all love those!), and considered the most important..newly installed HVAC for keeping your home cool during the summer and warm

    Dave Spence RE/MAX Roots

    107 Fay St, Winchester, VA 22602
  • /96

    $858,375

    • 3 Beds
    • 3.5 Baths
    • 4,469 Sq Ft

    650 Gough Rd, Winchester, VA 22602

    A "MacKenzie-Childs" inspired home awaits you and is better than new. Much detail put into this home where French country meets whimsical! Some highlights are as follows: Almost 2.75 acres of peaceful views/setting. Professional hardscaping and landscaping to include paver patio and walkways, BBQ station and fire pit area, new shed with herb garden station behind it and covered rear deck has

    Jim Thomson Realty ONE Group Old Towne

    650 Gough Rd, Winchester, VA 22602
  • /67

    $323,000

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

    151 Mccormick Cir Unit 203, Winchester, VA 22602

    55+ Condo Community, this charming 2-bedroom, 2-bathroom unit offers a perfect blend of comfort and style, featuring a Craftsman architectural design that welcomes you home. Step inside to find a thoughtfully designed interior with a combination kitchen and dining area, ideal for entertaining or enjoying quiet meals. The spacious family room off the kitchen is perfect for relaxation, while the

    Wanda Garris Miller Century 21 Redwood Realty

    151 Mccormick Cir Unit 203, Winchester, VA 22602
  • /30

    $370,000

    • 4 Beds
    • 2 Baths
    • 1,534 Sq Ft

    323 Russelcroft Rd, Winchester, VA 22601

    Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living space. Beautiful cared for by the homeowners. 3 bedrooms 2 full baths detached home .Beautiful Detached home with 3 bedrooms and 2 full baths + bonus room on the basement isfull finished with a family room. Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living

    Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

    323 Russelcroft Rd, Winchester, VA 22601
  • /80

    $679,900

    • 3 Beds
    • 2.5 Baths
    • 2,333 Sq Ft

    1153 Merrimans Ln, Winchester, VA 22602

    Welcome to this one-owner Cape Cod on sought-after Merrimans Lane, just steps from Roscommons. Thoughtfully designed and custom built, this home offers timeless style and comfortable living.Step inside to find gleaming hardwood floors, a well-appointed kitchen with a sunny breakfast area, and a lovely sunroom with direct access to the Trex deck—perfect for enjoying the peaceful views of

    Traci Shoberg RE/MAX Roots

    1153 Merrimans Ln, Winchester, VA 22602
  • /49

    $629,900

    • 4 Beds
    • 3.5 Baths
    • 3,829 Sq Ft

    114 Nassau Dr, Winchester, VA 22602

    Beautifully updated 4 bed, 3.5 bath colonial in a prime commuter location just minutes from I-81 and Route 7. Enjoy outdoor living with a fenced backyard, low-maintenance composite decking, brick patio, outdoor fireplace, and a storage shed. The spacious primary suite includes a large walk-in closet. The finished basement is ideal for entertaining, featuring a full bath and wet bar. Recent

    Sheila Pack RE/MAX Roots

    114 Nassau Dr, Winchester, VA 22602
  • /20

    $499,900

    • 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
  • /50

    $680,000

    • 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

    $255,000 Open Sun 1:30PM - 2:30PM

    • 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

    $939,950 Open Sat 12PM - 2PM

    • 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
  • /22

    $395,000

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

    1399 Chestnut Grove Rd, Winchester, VA 22603

    One Level home on a private 5 acre lot. Bring your horses, goats, chickens - this is the perfect farmette! Absolutely beautiful setting that includes a paddock and a barn/shed. New roof April 2025. New Laminate flooring in kitchen. Only 10 minutes from downtown Winchester and convenient to grocery, farmers’ markets, and the hospital. House is full of character and has an open floor plan! The

    Emma Kerns MarketPlace REALTY

    1399 Chestnut Grove Rd, Winchester, VA 22603
  • /35

    $340,000

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    115 Blue Ridge Ln, Winchester, VA 22602

    Welcome to 115 Blue Ridge Ln in Winchester, VA. This recently renovated 3-bedroom, 2-bath brick rancher sits on a 0.53-acre lot. This move-in ready home offers a perfect blend of charm and modern updates, just 10 minutes from historic Old Town Winchester. Inside, you’ll find new windows, new luxury vinyl plank flooring, fresh paint, updated lighting, and a functional layout perfect for everyday

    Jon Fleming Weichert Realtors - Blue Ribbon

    115 Blue Ridge Ln, Winchester, VA 22602
  • /22

    $270,000

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    303 Fox Dr, Winchester, VA 22601

    Charming Renovated Ranch in the Wooded Community of Wild Acres Welcome to this beautifully renovated 2-bedroom, 1-bath ranch-style home nestled in the serene and private subdivision of Wild Acres. Tucked among the trees, this 960 sq ft home offers the perfect blend of modern updates and cozy charm. Perk is for a one bedroom but home technically has two bedroomsInside, you'll find

    Brandy Clem Johnston and Rhodes Real Estate

    303 Fox Dr, Winchester, VA 22601
  • /10

    $225,000

    • Land
    • 20 Acres
    • $11,222 per Acre

    951 Bobcat Trail, Winchester, VA 22602

    Breathtaking Views and Endless Possibilities!Discover your own slice of paradise on this stunning 20.05-acre property! With a 3-bedroom perc already in place, drainfield and distribution box installed, and electric at the property, you're just a septic tank away from breaking ground. Part of the lot is already cleared, making it the perfect spot to build your dream home, weekend getaway, or

    Sharon Farinholt Realty ONE Group Old Towne

    951 Bobcat Trail, Winchester, VA 22602
  • /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
  • /31

    $425,000

    • Studio
    • 1,298 Sq Ft

    815 Woodland Ave, Winchester, VA 22601

    TWO HOMES FOR THE PRICE OF ONE! Welcome to a unique investment or multi-generational living opportunity with two separate homes on one property!Front House (815 Woodland Ave): On-street parking - 1400 Fin Sq FtThis charming 1920s Craftsman-style Cape Cod offers 3 bedrooms and 1 full bathroom, featuring a welcoming large front porch, original hardwood floors, updated electrical systems,

    RoxAnn Grimes RE/MAX Roots

    815 Woodland Ave, Winchester, VA 22601
  • /41

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 1,719 Sq Ft

    415 Quail Dr, Winchester, VA 22602

    Welcome to this beautiful 4 years young, 3-bedroom, 2 1/2-bath split foyer home, perfectly nestled on a peaceful dead-end road. Set on a spacious 1/2-acre lot with serene, wooded views, this home offers the perfect blend of comfort, privacy, and modern style.Step inside to discover luxury vinyl plank flooring throughout the entire home—durable, stylish, and low-maintenance. The heart of the

    Kerry Wysong Long & Foster Real Estate, Inc.

    415 Quail Dr, Winchester, VA 22602
  • /41

    $399,900

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

    115 Etnam St, Winchester, VA 22602

    Well maintained colonial in a mature neighborhood. Take a look at the curb appeal as you pull up to the large front porch. Walk through the front door to find a generous sized dining room. The kitchen is a welcoming place to cook all of your favorite meals. There is great counterspace for easy food prep. Off the kitchen you will find 2 living spaces, great for spreading out and having your own

    Dave Spence RE/MAX Roots

    115 Etnam St, Winchester, VA 22602
  • /34

    $350,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 2,436 Sq Ft

    216 Monticello Square, Winchester, VA 22602

    Seller is offering $5,000 toward purchasers closing cost with acceptable offer! Step into this beautifully designed 3-level townhome that offers both space and sophistication. With 3 bedrooms, 2.5 baths, and a 1-car garage, this home balances comfort and functionality perfectly. Interior Highlights:An upgraded kitchen featuring modern appliances, stylish cabinetry, and ample counter

    LESLIE WEBB Long & Foster Real Estate, Inc.

    216 Monticello Square, 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

    $460,000

    • 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
  • /23

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,446 Sq Ft

    209 S Braddock St, Winchester, VA 22601

    Opportunity is knocking! Here's your chance to purchase a unique home in the beautiful Winchester Historic district. Freshly painted interior is light and bright-Step inside to hardwood flooring on your left is the formal living room featuring a decorative brick fireplace with a mantel to display your treasures, on the main level you will find a full bath, laundry, and kitchen with Tiled Floors-

    Manuela Moyer Long & Foster Real Estate, Inc.

    209 S Braddock St, Winchester, VA 22601
  • /16

    $150,000

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    119 Averell Ave Unit 497, Winchester, VA 22603

    Welcome to Regency Lakes a all age active and vibrant community, where you can find your dream home.We have a beautiful maintenance free home that has a brand new roof with a transferable 30 year warranty. It has a beautiful gas fire place for those cold winter nights. New LPV flooring throughout the home, 2 year old HVAC system, 5 year old water heater and a recently installed water softner. The

    Kristina Kelly Regency Lakes

    119 Averell Ave Unit 497, Winchester, VA 22603
  • /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
  • /39

    $419,900 Open Sun 1PM - 3PM

    • 5 Beds
    • 2 Baths
    • 2,363 Sq Ft

    707 S Braddock St, Winchester, VA 22601

    Welcome to this charming, fully remodeled home located in the heart of Winchester.Experience the timeless appeal of Old Winchester charm, just minutes from the vibrant walking mall, shops, restaurants, and the famous Apple Blossom Parade route. This beautifully remodeled home features LVP flooring throughout and a light-filled open floor plan that seamlessly blends historic character with

    Heloisa Amar Samson Properties

    707 S Braddock St, Winchester, VA 22601
  • /50

    $699,000

    • 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
  • /36

    $379,900

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    111 Old Dominion Dr, Winchester, VA 22603

    JUST REDUCED!!!Welcome to 111 Old Dominion Dr — a beautifully maintained colonial nestled in a desirable Winchester neighborhood. This 3-bedroom, 2.5-bath detached home offers 1,664 square feet of bright, open living space featuring crown molding, recessed lighting, and modern finishes throughout (roof was changed in 2021, AC changed in 2021, water heater in 2021). The updated kitchen boasts

    Carolina Mosquera Weichert, REALTORS

    111 Old Dominion Dr, Winchester, VA 22603
  • /91

    $959,000 Open Sat 12PM - 2PM

    • 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
  • /19

    $308,000

    • 2 Beds
    • 1 Bath
    • 1,027 Sq Ft

    104 Redwood Ln, Winchester, VA 22603

    Charming 2bedroom 1bath house located minutes from downtown Winchester in Frederick County. House features a large kitchen, mudroom, attic, basement and large fenced in back yard. This house has the potential to become a four bedroom as the current owner has started framing in the upstairs for two additional bedrooms along with electrical hookup. Water heater is 2 years old and HVAC system is

    Courtney Spaid Crum Realty, Inc.

    104 Redwood Ln, Winchester, VA 22603
  • /63

    $849,990

    • 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
  • /36

    $409,900

    • 2 Beds
    • 2 Baths
    • 1,664 Sq Ft

    100 Candlewick Dr, Winchester, VA 22602

    “Cottage on Candlewick” - Welcome to easy, one-level living in the highly sought-after Cross Creek Village, a 55+ community designed for comfort, convenience, and connection. This beautifully maintained 2-bedroom, 2-bath home offers over 1,600 square feet of thoughtfully designed living space—all on one level for maximum accessibility.Perfectly situated near the front of the neighborhood

    Mark Francis ICON Real Estate, LLC

    100 Candlewick Dr, Winchester, VA 22602
  • /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!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 district and combines peaceful surroundings with unbeatable convenience—just one minute to

    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
  • /26

    $375,000

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

    1004 S Cameron St, Winchester, VA 22601

    PRICE REDUCED***Renovated Home in Winchester neighborhood.*** You’ll enter the house and find a spacious living room. As you continue walking, you’ll be led to the fully renovated kitchen. The kitchen features stainless steel appliances, including a new refrigerator, stove, microwave, dishwasher, new cabinets, and a granite countertop. The laundry room, located conveniently on the main level,

    Patricia Salgado Metas Realty Group, LLC

    1004 S Cameron St, Winchester, VA 22601
  • /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
  • /40

    $469,900

    • 5 Beds
    • 2 Baths
    • 1,956 Sq Ft

    116 S Pleasant Valley Rd, Winchester, VA 22601

    Welcome to 116 South Pleasant Valley Road! This fully-renovated gem has been meticulously transformed to offer a truly luxurious and modern living experience. You'll immediately appreciate the high-end finishes that grace every corner, making it feel brand new. Featuring 2 HVAC systems. The updated kitchen is a chef's delight, featuring new porcelain tile floors, sleek modern cabinetry, and

    Dan Whitacre Colony Realty

    116 S Pleasant Valley Rd, Winchester, VA 22601

Showing Results 81 - 120, Page 3 of 10

How to Buy a Home How to Finance a Home How to Sell a Home