5-Bedroom Houses for Sale in Winchester, VA

Listed well below market value, this stunning all-brick home in the sought-after Meadow Branch community was built in 2000 and has undergone extensive renovations in 2023 and 2024. The main-level bedroom includes a spacious, newly updated ensuite featuring an oversized marble-tiled shower, dual vanities, and a custom walk-in closet designed by ClosetsByDesign. The beautifully reimagined kitchen

Kiran K. Morzaria Parekh Redfin Corporation

Welcome to your dream retreat—set on 5 private acres just outside Winchester, this fully renovated home offers the perfect blend of luxury and land. With 5 spacious bedrooms and 3.5 beautifully updated bathrooms, this property is designed for comfort, functionality, and style.From the chef’s kitchen to the expansive living areas, every detail has been thoughtfully upgraded. Whether you're

Nicole Renzetti EXP Realty, LLC

Spacious & Elegant 5-Bedroom Colonial in the Heart of Winchester!This beautifully maintained 5-bedroom, 4-bath Colonial offers over 4,000 sq. ft. of comfortable living in the City of Winchester. Hardwood flooring flows throughout the home, creating a warm and inviting atmosphere. The main level includes a convenient bedroom, a sunroom filled with natural light, and access to a large

Sheila Pack RE/MAX Roots

Nestled on a quiet cul-de-sac within city limits, this exquisite 5-bedroom, 4.5-bath colonial offers over 4,625 square feet of finished living space and a rare backdrop of preserved battlefield views. Step into the grand two-story foyer flanked by formal living and dining rooms, then flow into the expansive family room featuring coffered ceilings and a dramatic floor-to-ceiling stone

Julie Shiley Coldwell Banker Realty

Welcome to your dream home at 140 Whistlewood Ln in Winchester! This stunning 5-bedroom, 3.5-bath home is nestled on 2 private acres with a fully fenced backyard, offering space, privacy, and elegance. Inside, hardwood floors flow throughout the main living area. The open-concept kitchen features granite countertops, a large island, stainless steel appliances, a breakfast nook, and a walk-in

Abby Walters Preslee Real Estate

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

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.

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

Handsome Colonial loaded with possibilities, from a multigenerational home to spacious entertaining venues. It features a Main Floor ensuite Bedroom and expansive finished basement with kitchenette and outside entrance for possible in-law suite. Inviting lot with large pool and covered and open decks in large privacy fenced back yard. Conveniently located in lovely, well-maintained

Dallas Croft Samson Properties

The Hayden is a three-story plan with 6 bedrooms and 4 bathrooms in 3,205 square feet. The main level features a flex room adjacent to the foyer, ideal for a formal dining room or home office. The gourmet kitchen has an oversized island for extra seating and a large pantry, and it opens to the dining area and a spacious living room. A bedroom with a full bathroom completes the main level. The

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

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

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

Welcome to this well-maintained split-foyer home, offering five bedrooms and two full bathrooms across two thoughtfully designed levels. Hardwood floors extend throughout the main level, adding warmth and character to the central living spaces.The kitchen is both functional and stylish, featuring stainless steel appliances—including a new refrigerator and dishwasher (2023)—along with

Chris Craddock EXP Realty, LLC

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

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. The updated kitchen is a chef's delight, featuring new porcelain tile floors, sleek modern cabinetry, and stunning quartz countertops.

Dan Whitacre Colony Realty

Welcome to 912 Opequon Ave- Spacious, Updated & Perfectly Located in Winchester !Opportunity meets versatility in this beautifully updated 5 bedrooms, 2 bath home nestled in one of Winchester most walkable and convenient neighborhoods! Whether you're a homeowner seeking flexible living space or an investor eyeing income potential, this property checks every box . Freshly painted interior

max cortijo Fairfax Realty of Tysons

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 residence features a main-level bedroom and full bath—ideal

Sheila Pack RE/MAX Roots

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.

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

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

PRICE RARE UNIQUE OPPORTUNITY KNOCKS!ALL inside units cleaned, and junk removed - Ready for new investor.Warehouse also cleaned of junk and any hazards however has been condemned by City of Winchester as warehouse roof has caved in.Do not miss this rare opportunity to own this rare, unique property in Winchester. Work with the city of Winchester and turn this into your

Pakeeza Akhtar The KOR Group, Inc.

Active again, Buyer's loan fell through. Charming Colonial located in the heart of Winchester. Only a few minutes walk to the Old Town Mall. This home features 5 bedrooms and 3 1/2 baths with 4 levels. There's a Primary Bedroom and Bathroom located on the main level with doors that open onto the back deck. The family room boasts hardwood floors and a wood burning fireplace. The kitchen is

Julie Teets Long & Foster Real Estate, Inc.

This beautiful, remodeled home is very well located, close to shopping and entertainment. The upstairs area features 3 spacious bedrooms, 2 full bathrooms. Also has sleek LVP floors throughout the home. The heart of the home is the sleek, all-new kitchen, equipped with shaker cabinets, quartz countertops, and stainless-steel appliances.The home offers a walkout basement with an independent exit,

Marco Novillo Spring Hill Real Estate, LLC.

This luxury ranch estate boasts a whopping 8,295 square feet (with another 1,152 in the basement) on a lovely 1.5 acres. In 1998 the home was completely remodeled and expanded by the local, renowned architectural firm of Reader and Swartz. This home features beautiful, all-brick craftsmanship with herringbone details and hardscaping, curated landscaping, and mature trees for additional privacy.

Dan Whitacre Colony Realty

BONUS BONUS BONUS The Seller is very motivated and is offering $15,000.00 towards repairs and also offering 3% towards closing cost. The garage has been converted into a private living area. Great for the out of town family that need their privacy or the young adult that may want their independence or maybe you would like to have a private living area for your in-laws. So no matter the reason

Janet Broyles CENTURY 21 New Millennium

The Elm floor plan offers a versatile layout with 2,415 square feet, perfect for families or entertaining guests. The main level includes a secondary bedroom and full bathroom, ideal for accessibility, home office use, or play space. Upstairs, you’ll find four more bedrooms, including a generous primary suite, two additional full bathrooms, and a conveniently placed laundry room. Set for

Brooks Sears D R Horton Realty of Virginia LLC

The Elm floor plan features a flexible design with 2,415 square feet of living space, making it ideal for families or hosting guests. On the main level, you’ll find a secondary bedroom and a full bath - perfect for convenience or multi-generational living. Upstairs, four additional bedrooms, including a spacious primary suite, along with two full baths and a conveniently located laundry room,

Brooks Sears D R Horton Realty of Virginia LLC

The northeast-facing Elm model home is now for sale! This home comes with 5 bedrooms, 3.5 bathrooms, and a 2-car garage. You will love the granite countertops, stainless steel appliances, and recessed lighting in the kitchen. Other highlights include: Spacious 9 ft ceilings on the main level, over-sized kitchen island, upgraded cabinets, stainless steel appliances, luxury plank flooring on main

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

Coming Soon to Market is an 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. 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

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