5-Bedroom Homes for Sale in Winchester, VA

Welcome to 127 Kinross Dr in Winchester, VA! This spacious 5-bedroom, 3.5-bath home offers 3,494 sq. ft. of beautifully updated living space with modern upgrades throughout. Located in the well sought-after RAVEN WING Community due to its perfect location and commuter friendly access to all major highways (Route 50, Route 7, Route 66 & Interstate 81), shopping and other great perks on the East

Matthew Roberts Redfin Corporation

Spacious Ranch-Style Retreat on 5+ Acres with Mountain ViewsWelcome to this beautifully updated ranch-style home offering over 5 acres of privacy, modern comforts, and sweeping mountain views. From the inviting covered front porch, step inside to a bright, open living room featuring durable LVP flooring and sliding glass doors that lead to an expansive deck—the perfect spot to take in the

Amanda Gulla Preslee Real Estate

Welcome to 108 Katie Lane in beautiful Stonebrook Farms. This classic brick home has space, charm, and a setting that feels like home the moment you pull up. With five large bedrooms, including a comfortable primary suite, there is room for everyone.The main level features an open floor plan with hardwood floors throughout, creating a warm and welcoming feel. A gas fireplace adds a cozy

Sharon Farinholt Realty ONE Group Old Towne

Gracious living abounds in this 3 years young Preston model in the prestigious community of Abrams Pointe. Designed for daily living and entertaining with several upgrades and custom features, this home offers it all on a .49AC lot backing to trees for privacy. The first floor offers 10' high ceilings and 9' doors for added ambiance. A custom double sliding glass door in the great room provides

Becky Hanrahan Coldwell Banker Realty

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

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.

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

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

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

MOTIVATED SELLER! 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

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.

Brand New Matisse is now under construction for Late Summer/Early Fall Move In at Hiatt Pointe at Snowden Bridge, a community for those 55 or better and can still be personalized with your interior selections! This thoughtfully designed home offers unparalleled comfort and flexibility to suit your unique lifestyle. The heart of the home is an open-concept haven, seamlessly blending a gourmet

Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

Robin Luu TTR Sothebys International Realty

Welcome to 292 Fortress Drive, where pride of ownership shines throughout! This stunning home has been beautifully updated and shows in perfect condition. The newly finished basement adds incredible value, featuring a 5th bedroom and full bath—ideal for guests, extended family, or a private office. The main level offers a modern kitchen with granite countertops, stylish cabinetry, and plenty of

Deborah Matthews ERA Oakcrest Realty, Inc.

Welcome to 25 E Hart Street! Nestled in the heart of downtown Winchester, this beautifully updated 5-bedroom, 3-bath home is the perfect mix of charm, space, and convenience. Step inside to a bright, spacious living room where a wood-burning fireplace provides the perfect spot to relax and unwind. The updated kitchen is a dream with quartz countertops, stainless steel appliances, crisp white

Liz Owings RE/MAX Roots

Fresh to market is this unexpected property that offers the sense of home combined with the amenities of a full-time retreat. This country escape is located within minutes of town with NO HOA. Markets, restaurants, stores, shopping are handy for a quick errand and allows you to get back fast and enjoy a lazy day at the pool. Additional offerings include 9.83 private acres, a fully outfitted

Angela Duncan MarketPlace REALTY

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

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

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

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

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.

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.

1019 Berryville Avenue, Winchester, VA 22601 is a Fully-rented triplex located just minutes from Old Town Winchester and Shenandoah University. This approximately 3,000 sq. ft. property is configured as three fully independent residential and commercial units. All units have private entrances, full kitchens, and separate electric. Middle unit may be used for commercial space. Units have been

Pamela Debnam Houwzer, LLC

PRICE REDUCED .....DO YOU HAVE A LARGE FAMILY AND NEED YOUR OWN SPACE. HERE IS A 6 BEDROOMS 3 BATHROOMS WITH A IN-LAW SUITE. OVER 3900+ SQ. FT FINISHED. OFF STREET PARKING FOR 6 CARS. SHED AND STILL ROOM TO RELAX OUTBACK.

Richard Kozlowski Long & Foster Real Estate, Inc.

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

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

HOUSE IS LISTED UNDER CURRENT APPRAISED VALUE. $ 25,000 OF INSTANT EQUITY COULD BE YOURS. Buyers Financing Fell Though,Welcome to this generously sized 5-bedroom, 3.5-bathroom home located in the sought-after Oakdale Crossing community of Winchester, VA. This property offers a fantastic opportunity to personalize and update to your taste.Inside, you’ll find a bright, flowing

Ruby Miller Samson Properties

This property is currently zoned as fully commercial but has the potential to be changed to: Mixed Use or Fully Residential with proper city approval. Additional information from city located in documents. This home will need a Kitchen.Situated in Downtown Winchester, 214 S Braddock is waiting for your ideas! Built in 1865, this home features historic charm including exposed brick walls,

Matt Leiva Keller Williams Realty

Situated on a 2.5 acre lot in highly desirable area, this stunning Colonial home offers an open floor plan perfect for entertaining. Thoughtfully designed with a main-level ensuite and a second primary suite on the upper level; this home provides flexible living options for modern convenience. Spacious and filled with natural light, the home features a welcoming foyer, a beautiful kitchen, and

Lilly Triplett Colony Realty

REDUCED! REDUCED!! REDUCED!!! Don't miss this well cared for home featuring 5 bedrooms and 3.5 bathrooms! It's located in a quiet neighborhood on a cul-de-sac and convenient to route 7 and Route 81 for commuters. NEW Large, private 6 car asphalt driveway so plenty of off-street parking! Whole length of house rear deck for entertaining! Featuring rare main level bedroom with attached full

Sara Helmke Samson Properties

Introducing the Salem floorplan at The Retreat at Winding Creek! The first-floor owners' bedroom house you've been waiting for! On the main floor, you will find a formal dining room, laundry room, and half bath. The open-concept kitchen and living areas are perfect for entertaining. The kitchen has stainless steel appliances by Whirlpool with granite countertops. Upstairs are four additional

Brooks Sears D R Horton Realty of Virginia LLC

Introducing the Salem floorplan at The Retreat at Winding Creek! The first-floor owners bedroom house you've been waiting for! On the main floor, you will find a formal dining room, laundry room, and half bath. The open-concept kitchen and living areas are perfect for entertaining. The kitchen has stainless steel appliances by Whirlpool with granite countertops. Upstairs are four additional

Brooks Sears D R Horton Realty of Virginia LLC

Very private community all paved road. Close to town with wooded lots 10 minutes to town. Make your selections. This home boosts two level living with 3,056 sq. ft. of floor plan with so many features others would call them upgrades! Brick front with cement siding on three sides. Large concrete front porch with concrete lead walk. No HOA. Builders upgrades: hardwood entire house (except baths

Jim Thomson Realty ONE Group Old Towne

The Amelia Model by Merrifield Homes. Price includes finished basement. This is a very rare customizable house on a subdivision lot in Frederick County. Built by Merrifield Homes, buyers can choose layout, paint, cabinets, countertops, lighting, decking, hardwood stain, etc. Final price depends on selections, but this house is already loaded, including the hardwood, trim, covered porch, tile

JP Carr Merrifield Realty, LLC