Keller Williams
  • Home
  • Home Value
  • Buyers
  • Sellers
  • Rental Search
  • About
  • Webinars
  • Downsizing
  • Blog
  • FL Listings
  • VA, MD & DC Listings
Login
1.888.840.5553

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Quick Winchester VA MLS Search

TO
Advanced Search

Address Search

Browse All Winchester VA 5 Bedroom Properties for Sale

144 Morning Glory, Winchester image
144 Morning Glory, Winchester $525,000

Nestled in the charming Apple Ridge community, this stunning Colonial-style home offers a perfect blend of comfort and elegance. Set on a generous 0.4-acre lot, the prope...

  • 5 Beds
  • 4 Baths
  • Apple Ridge SubDv.
  • 22602 Zip Code
  • COMING SOON Status
243 Summerfield Dr, Winchester image
243 Summerfield Dr, Winchester $879,900

Immaculate custom home sitting on a half-acre lot in desirable Raven Pointe! Beautiful hardwood floors flow throughout the main level, leading into a dramatic family room...

  • 5 Beds
  • 5 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • COMING SOON Status
139 Darby Dr, Winchester image
139 Darby Dr, Winchester $625,000

COMING SOON! Being beautifully remodeled and updated, this home is getting a fresh new look inside and out! Enjoy relaxing times on the expansive front porch and enterta...

  • 5 Beds
  • 3 Baths
  • Raven Wing SubDv.
  • 22602 Zip Code
  • COMING SOON Status
102 Julie Ct, Winchester image
102 Julie Ct, Winchester $889,900

Opportunities of this caliber in the highly coveted Stonebrook Farms community are exceptionally rare. Positioned on a premium cul-de-sac lot backing directly to mature, ...

  • 5 Beds
  • 5 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
342 Canyon Rd, Winchester image
342 Canyon Rd, Winchester $724,000

Welcome to 342 Canyon Rd, a spacious and beautifully maintained home in the desirable Twin Lakes Overlook community on Winchester's east side. Situated on a beautifully l...

  • 5 Beds
  • 4 Baths
  • Twin Lakes Overlook SubDv.
  • 22602 Zip Code
  • COMING SOON Status
151 Travis Ct, Winchester image
151 Travis Ct, Winchester $535,000 ▼

Welcome to 151 Travis Court, a beautifully maintained 5-bedroom, 3.5-bath Colonial tucked away at the end of a quiet cul-de-sac in the highly desirable Red Fox Run commun...

  • 5 Beds
  • 4 Baths
  • Red Fox Run SubDv.
  • 22602 Zip Code
  • ACTIVE Status
440 Canyon Rd, Winchester image
440 Canyon Rd, Winchester $575,000

Welcome home to this stunning 5-bedroom, 3-bath, 3-story Colonial located in the highly desirable Sovereign Village community on the east side of Winchester. Offering spa...

  • 5 Beds
  • 3 Baths
  • Sovereign Village SubDv.
  • 22602 Zip Code
  • ACTIVE Status
136 Cahille Dr, Winchester image
136 Cahille Dr, Winchester $750,000

Nestled towards the end of a quiet dead-end street in the sought-after Raven Pointe community, this stunning 5-bedroom, 4.5-bath home offers the perfect blend of elegance...

  • 5 Beds
  • 5 Baths
  • Raven Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
135 Wappinger Ter, Winchester image
135 Wappinger Ter, Winchester $515,990 ▼

The Deerfield offers a smart, stylish layout with five bedrooms and four-and-a-half baths—perfect for both everyday living and entertaining. The kitchen features a large ...

  • 5 Beds
  • 4 Baths
  • Retreat At Winding Creek SubDv.
  • 22602 Zip Code
  • PENDING Status
130 Wappinger Ter, Winchester image
130 Wappinger Ter, Winchester $509,990 ▼

Discover the perfect blend of space, function, and style in the Elm—a thoughtfully designed 2,415 sq. ft. two-story home featuring 5 bedrooms, 3 full bathrooms, a versati...

  • 5 Beds
  • 3 Baths
  • Retreat At Winding Creek SubDv.
  • 22602 Zip Code
  • ACTIVE Status
118 Aulee Ct, Winchester image
118 Aulee Ct, Winchester $789,900

This beautiful, well-cared-for home overlooks a lake and stream directly behind the house. The owners have painted the entire interior, added new lighting fixtures, new ...

  • 5 Beds
  • 5 Baths
  • Twin Lake Overlook SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
614 Mohawk Trl, Winchester image
614 Mohawk Trl, Winchester $580,000

Welcome to 614 Mohawk Trail in the Shawneeland community! Nestled on 1.67 acres, this spacious 5-bedroom, 4-bath home offers over three levels of flexible living space, m...

  • 5 Beds
  • 4 Baths
  • Shawneeland SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
303 Pembridge Dr, Winchester image
303 Pembridge Dr, Winchester $399,000

Discover the potential of this charming split-level home nestled in the desirable Pembridge Heights community. This residence features five spacious bedrooms and three fu...

  • 5 Beds
  • 3 Baths
  • Pembridge Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
222 Cavalry Dr, Winchester image
222 Cavalry Dr, Winchester $549,000 ▼

Price reduced, with motivated sellers! Welcome to 222 Cavalry Drive — a beautifully maintained brick-front colonial offering timeless style, functional living, and except...

  • 5 Beds
  • 4 Baths
  • Pioneer Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
131 Thornton Way, Winchester image
131 Thornton Way, Winchester $599,900 ▼

One of the great houses with a great price, don't miss it! Welcome to this beautiful family house in desirable Senseny Village Community! This house condition like new. B...

  • 5 Beds
  • 4 Baths
  • Senseny Village SubDv.
  • 22602 Zip Code
  • ACTIVE Status
295 Huntersridge Rd, Winchester image
295 Huntersridge Rd, Winchester $627,102 ▼

Price Drop. Come check this home out. The listing remarks below come directly from the Seller's. This home is a true gem. Hello! Human here! I just want to touch base w...

  • 5 Beds
  • 4 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
206 Dogwood Rd, Winchester image
206 Dogwood Rd, Winchester $425,000

Welcome to 206 Dogwood Rd. Well maintained 5 Bedroom 2 Bath Cape Cod in a quiet neighborhood conveniently located a short distance from the downtown area. HVAC has just b...

  • 5 Beds
  • 2 Baths
  • Shenandoah Hills SubDv.
  • 22602 Zip Code
  • ACTIVE Status
440 Bristol Dr, Winchester image
440 Bristol Dr, Winchester $849,000

Some homes check a few boxes. 440 Bristol Drive showed up with its own notebook and started making new boxes. Nestled on 13.8 gorgeous acres in Winchester, this stunning...

  • 5 Beds
  • 3 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
801 Armistead St, Winchester image
801 Armistead St, Winchester $1,150,000

There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been worki...

  • 5 Beds
  • 5 Baths
  • Meadowbranch SubDv.
  • 22601 Zip Code
  • ACTIVE Status
220 Lehigh, Winchester image
220 Lehigh, Winchester $685,000 ▼

Some homes are new. This one is finished. Welcome to 220 Lehigh Drive, where the details have already been thoughtfully completed, allowing you to skip the time, expense,...

  • 5 Beds
  • 4 Baths
  • Senseny Village SubDv.
  • 22602 Zip Code
  • ACTIVE Status
106 Etnam St, Winchester image
106 Etnam St, Winchester $484,900 ▼

Beautiful updated 3400 sqft home, ready for immediate move-in! Featuring a host of updates including a new roof, flooring,counters and more, this lovingly kept home has ...

  • 5 Beds
  • 3 Baths
  • Pembridge Heights SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
419 Summit Ave, Winchester image
419 Summit Ave, Winchester $459,999 ▼

Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and...

  • 5 Beds
  • 3 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
974 Wayne Dr, Winchester image
974 Wayne Dr, Winchester $614,999

Finally, a five-bedroom, 3.5 bath home in the city of Winchester with over 4200 sq ft of living space within minutes of Valley Health and shopping. Beautifully landscaped...

  • 5 Beds
  • 4 Baths
  • Meadow Branch South SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
660 Beehive Way, Winchester image
660 Beehive Way, Winchester $554,900 ▼

Enjoy city living in this spacious and light-filled home featuring 5 bedrooms and 3.5 baths. Fresh new carpeting has been installed on the upper level and in the family r...

  • 5 Beds
  • 4 Baths
  • Park Place SubDv.
  • 22601 Zip Code
  • ACTIVE Status
114 Settlers Cir, Winchester image
114 Settlers Cir, Winchester $559,900 ▼

BACK ON THE MARKET AFTER THE INSTALLATION OF NEW CARPET !! MOVE IN CONDITION PRICED TO SELL FAST LOCATED IN THE CUL-DE-SAC WHICH HAS A PLAYGROUND - SEPERATE IN-LAW-SUITE ...

  • 5 Beds
  • 4 Baths
  • Pioneer Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
159 Abrams Pointe Blvd, Winchester image
159 Abrams Pointe Blvd, Winchester $749,900 ▼

***You could get up to $3,000 with use of preferred lender for closing cost assistance or use funds for a rate buy-down (restrictions apply and not all will qualify, cont...

  • 5 Beds
  • 5 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
769 Seldon Dr, Winchester image
769 Seldon Dr, Winchester $799,000

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 finis...

  • 5 Beds
  • 5 Baths
  • Meadow Branch SubDv.
  • 22601 Zip Code
  • ACTIVE Status
2450 Cardigan Way, Winchester image
2450 Cardigan Way, Winchester $646,090

This 5‑bedroom Torrington home with a main‑level primary suite is still available to personalize—choose your own flooring, quartz countertops, cabinets, and fixtures, and...

  • 5 Beds
  • 5 Baths
  • Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
446 N Loudoun St, Winchester image
446 N Loudoun St, Winchester $599,950 ▼

Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. Th...

  • 5 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
2230 Jones Rd, Winchester image
2230 Jones Rd, Winchester $2,200,000

Set on 21.5 acres just minutes from downtown Winchester, this 5-bedroom home offers over 5,800 finished square feet with a blend of space, functionality, and outdoor livi...

  • 5 Beds
  • 5 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
813 Chelsea Dr, Winchester image
813 Chelsea Dr, Winchester $595,000 ▼

BEAUTIFUL NEW PRICE FOR A BEAUTIFUL HOUSE! ELEGANT AND SPECTACULAR! DRAMATIC SHOW STOPPER HOME IN MEADOW BRANCH SOUTH. If your passion is entertaining and fine living, th...

  • 5 Beds
  • 3 Baths
  • Meadowbranch South SubDv.
  • 22601 Zip Code
  • ACTIVE UNDER CONTRACT Status
2486 Scotch Bonnet Dr, Winchester image
2486 Scotch Bonnet Dr, Winchester $664,190

5 bedroom home on a cul-de-sac is still available for you to personalize with your choice of flooring, counters, cabinets and fixtures and build for move in this year! R...

  • 5 Beds
  • 5 Baths
  • Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
Lot 191 Malbec Ct, Winchester image
Lot 191 Malbec Ct, Winchester $696,455

Welcome to Abrams Pointe, a new single-family home community in an established Winchester neighborhood. The Carlisle blends modern design, spacious living, and a desirabl...

  • 5 Beds
  • 5 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • PENDING Status
605 Dunlap St, Winchester image
605 Dunlap St, Winchester $390,000 ▼

Priced to reflect the need for some updating, this home offers opportunities and personalization while remaining move-in ready 1011sf total living space. This home is in ...

  • 5 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
274 Woodside Ln, Winchester image
274 Woodside Ln, Winchester $775,000 ▼

PRICE JUST REDUCED! Come take a look at this beautiful home located in the coveted neighborhood of Spring Valley Estates, on five wooded acres, and is only minutes away ...

  • 5 Beds
  • 4 Baths
  • Spring Valley SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
199 Laurel Grove Rd, Winchester image
199 Laurel Grove Rd, Winchester $999,990 ▼

Nestled in the scenic countryside of Winchester, this impressive custom built home offers space, privacy, and beautiful Shenandoah Valley surroundings. Located in Frederi...

  • 5 Beds
  • 4 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
219 Lehigh, Winchester image
219 Lehigh, Winchester $619,000 ▼

This nearly new Lennar home offers the advantages of modern construction combined with thoughtful upgrades and future expansion potential in a location that keeps you con...

  • 5 Beds
  • 4 Baths
  • Senseny Village SubDv.
  • 22602 Zip Code
  • ACTIVE Status
Lot 5 Keval Gyan Way, Winchester image
Lot 5 Keval Gyan Way, Winchester $850,000

Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a h...

  • 5 Beds
  • 3 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
1631 Back Mountain Rd, Winchester image
1631 Back Mountain Rd, Winchester $1,700,000 ▼

This unique property is the definition of an oasis in the woods. Surrounded by 180 glorious private acres, this home dazzles with grandeur while blending natural elements...

  • 5 Beds
  • 4 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
122 Cherry Hill Cir, Winchester image
122 Cherry Hill Cir, Winchester $435,000

Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and fou...

  • 5 Beds
  • 4 Baths
  • Green Acres SubDv.
  • 22602 Zip Code
  • ACTIVE Status
150 Ewell Dr, Winchester image
150 Ewell Dr, Winchester $850,000 ▼

Welcome to Equestrian Estates, a highly sought-after Winchester community with no HOA, where space, style, and flexibility come together beautifully. This stately 5-bedro...

  • 5 Beds
  • 6 Baths
  • Equestrian Estates SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
128 Wagtail Ln, Winchester image
128 Wagtail Ln, Winchester $634,990 ▼

Brand New Matisse is Ready for Move In at Hiatt Pointe at Snowden Bridge, a community for those 55 or better! The heart of the home is an open-concept haven, seamlessly ...

  • 5 Beds
  • 4 Baths
  • Hiatt Pointe At Snowden Bridge SubDv.
  • 22603 Zip Code
  • PENDING Status

5 Bedroom Winchester Real Estate

Our website features the best real estate search for 5 bedroom properties available in Winchester and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Like or Share

Address Search

Anne Nouri headshot
Anne Nouri

keller william luxury
1.888.840.5553
Contact Me

Browse Winchester Homes by Features

  • Styles
  • Subdivisions
  • Buildings

Browse Winchester Homes by Property Type

  • Single Family
  • Townhouses
  • Land
  • Manufactured Homes
  • Historical Homes
  • Foreclosures
  • Short Sales
  • Just Listed
  • Homes with Pool

Browse Winchester Homes by Price Range

  • Under $200K
  • $200K-$300K
  • $300K-$400K
  • $400K-$500K
  • $500K-$600K
  • $600K-$700K
  • $700K-$800K
  • $800K-$900K
  • $900K-$1 Million
  • $1 Million-$2 Million
  • $2 Million-$3 Million
  • $3 Million-$4 Million
  • $4 Million-$5 Million
  • Above $5 Million

Browse Winchester Homes by # of Bedroom

  • 1
  • 2
  • 3
  • 4
  • 5
  • 6+

Browse Winchester Homes by # of Bathroom

  • 1
  • 2
  • 3
  • 4
  • 5
  • 6+

Browse Winchester Homes by Lot Size

  • 1 Acre
  • 2+ Acres
  • 3+ Acres
  • 4+ Acres
  • 5+ Acres
  • 6+ Acres

Browse Winchester Homes by Square Feet

  • 500+ Sqft
  • 700+ Sqft
  • 1000+ Sqft
  • 1250+ sqft
  • 1500+ Sqft
  • 1750+ Sqft
  • 2000+ Sqft
  • 2250+ Sqft
  • 2500+ Sqft
  • 2750+ Sqft
  • 3000+ Sqft
  • 3500+ Sqft
  • 4000+ Sqft
  • 5000+ Sqft
  • 7500+ Sqft

Winchester Real Estate Market Reports

  • Winchester

Mortgage Calculator

Amount of Loan
Annual Interest Rate
%
Term of Loan
Years
Calculate

Does not include any taxes or fees.
Please consult a financial professional.

  • Home
  • Advanced Search
  • Sellers
  • Buyers
  • Rental Search
  • About
  • Blog
  • Connect

  • Alexandria
  • Arlington
  • Ashburn
  • Fairfax
  • Leesburg
  • Mclean
  • Middleburg
  • Purcellville
  • Reston
  • Round Hill
  • Springfield
  • Sterling
  • Upperville
  • Vienna
  • Waterford
  • Winchester
  • Woodbridge
  • Delray Beach
  • Jupiter
  • Lake Park
  • North Palm Beach
  • Palm Beach
  • Palm Beach Gardens
  • Palm Springs
  • Royal Palm Beach
  • West Palm Beach
  • Washington DC
IDX Real Estate Websites by
, an FNF RE Tech Company • Accessibility • Terms • Privacy