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Browse All Winchester VA 5 Bedroom Properties for Sale

223 Asbury Rd, Winchester image
223 Asbury Rd, Winchester $549,900

“Pioneer Heights Colonial” - Welcome to this beautifully maintained colonial in the desirable Pioneer Heights neighborhood, ideally situated just off Route 7 for easy com...

  • 5 Beds
  • 4 Baths
  • Pioneer Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
300 Pembridge Dr, Winchester image
300 Pembridge Dr, Winchester $439,000

Welcome to this newly renovated and thoughtfully designed 5-bedroom, 3-full-bath home offering exceptional flexibility for modern living or rental income. Featuring two ...

  • 5 Beds
  • 3 Baths
  • Pembridge Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
110 Bentpath Ct, Winchester image
110 Bentpath Ct, Winchester $710,000

Welcome to 110 Betpath Ct, nestled within the premier Twin Lakes Overlook (TLO) enclave of exclusively single-family homes by Toll Brothers and Richmond American, this ex...

  • 5 Beds
  • 4 Baths
  • Twin Lake Overlook SubDv.
  • 22602 Zip Code
  • ACTIVE Status
174 Williamson Rd, Winchester image
174 Williamson Rd, Winchester $759,900

This spectacular, move-in-ready home shows like a professional model, showcasing exquisite designer touches, custom window treatments (included), and premium finishes thr...

  • 5 Beds
  • 5 Baths
  • Abrams Pointe SubDv.
  • 22602 Zip Code
  • ACTIVE Status
337 Canyon Rd, Winchester image
337 Canyon Rd, Winchester $674,000

Welcome to 337 Canyon Road, a spacious brick-front home offering more than 4,600 finished square feet in desirable Twin Lakes Overlook. The open-concept main level featur...

  • 5 Beds
  • 4 Baths
  • Twin Lakes Overlook SubDv.
  • 22602 Zip Code
  • COMING SOON Status
632 Stonymeade Dr, Winchester image
632 Stonymeade Dr, Winchester $1,025,000

Opportunities in Stonymeade don't come along often—and once you arrive, it's easy to understand why. Tucked away on 3.2 beautifully maintained acres with a wooded perimet...

  • 5 Beds
  • 4 Baths
  • Stonymeade SubDv.
  • 22602 Zip Code
  • ACTIVE Status
102 Forest Valley Rd, Winchester image
102 Forest Valley Rd, Winchester $597,000 ▼

Welcome to this beautifully maintained home in the established Stonebrook Farms community, perfectly situated on a quiet cul-de-sac and surrounded by mature trees and lan...

  • 5 Beds
  • 3 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
854 Valley Mill Rd, Winchester image
854 Valley Mill Rd, Winchester $1,170,000

Unique 5+ acre property in Winchester. Beautiful home with plenty of space for everyone's interests. 5 bedrooms- all with en suite bathrooms. High end kitchen designed by...

  • 5 Beds
  • 6 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
922 Wayne Dr, Winchester image
922 Wayne Dr, Winchester $615,000

Welcome home to this beautifully updated brick-front residence in the City of Winchester, where a thoughtful floor plan, generous living spaces with 9' ceilings on the ma...

  • 5 Beds
  • 4 Baths
  • Meadow Branch South SubDv.
  • 22601 Zip Code
  • ACTIVE Status
136 Plaid Hill Dr, Winchester image
136 Plaid Hill Dr, Winchester $729,990

Rare cul-de-sac opportunity in sought-after Snowden Bridge! This stunning 5-bedroom Sinclair is under construction for a year-end move-in and offers the perfect blend of ...

  • 5 Beds
  • 5 Baths
  • Snowden Bridge SubDv.
  • 22603 Zip Code
  • PENDING Status
102 Primrose Pl, Winchester image
102 Primrose Pl, Winchester $499,900

Nestled in the charming Apple Ridge community, this delightful Colonial home offers a perfect blend of comfort and convenience. With 2,528 sq. ft. of living space, this r...

  • 5 Beds
  • 3 Baths
  • Apple Ridge SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1605 Fort Braddock Ct, Winchester image
1605 Fort Braddock Ct, Winchester $530,000

Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square...

  • 5 Beds
  • 4 Baths
  • Fort Braddock Heights SubDv.
  • 22601 Zip Code
  • ACTIVE Status
103 Renee Ln, Winchester image
103 Renee Ln, Winchester $710,000 ▼

Welcome to this gorgeous single family home with custom details galore in the lovely Lynnehaven community! Approaching the home you are welcomed by a spacious front porch...

  • 5 Beds
  • 4 Baths
  • Lynnehaven SubDv.
  • 22602 Zip Code
  • ACTIVE Status
769 Seldon Dr, Winchester image
769 Seldon Dr, Winchester $760,000

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
139 Wappinger Ter, Winchester image
139 Wappinger Ter, Winchester $519,990

The Deerfield offers a thoughtfully designed floor plan with five bedrooms and four-and-a-half baths, ideal for both everyday living and entertaining. <br><br> The open-...

  • 5 Beds
  • 4 Baths
  • Retreat At Winding Creek SubDv.
  • 22602 Zip Code
  • ACTIVE Status
218 Babbs Mountain Rd, Winchester image
218 Babbs Mountain Rd, Winchester $935,000 ▼

A PRIVATE CUSTOM-BUILT ESTATE SURROUNDED BY NATURE — WITH YOUR OWN RESORT-STYLE POOL! Set on an extraordinary 6.44 private acres, this exquisite custom-built residence of...

  • 5 Beds
  • 3 Baths
  • Babbs Mountain SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
313 Lehigh Dr, Winchester image
313 Lehigh Dr, Winchester $630,000

***Very motivated Sellers*** Set within the desirable Senseny Village community, 313 Lehigh Drive offers an exceptional blend of refined living and effortless comfort. Th...

  • 5 Beds
  • 4 Baths
  • Senseny Village SubDv.
  • 22602 Zip Code
  • ACTIVE Status
223 Fairfield Dr, Winchester image
223 Fairfield Dr, Winchester $725,000

Beautifully remodeled with exceptional care and attention to detail by its current owners, this stunning 5-bedroom, 3-bath home offers over 4,400 finished square feet on ...

  • 5 Beds
  • 4 Baths
  • Oakdale Crossing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
199 Meeting House Dr, Winchester image
199 Meeting House Dr, Winchester $699,000 ▼

3.46 ACRES • MOUNTAIN VIEWS • NO HOA • MAIN-LEVEL PRIMARY Discover a different kind of Winchester living at 199 Meeting House Drive. Tucked at the end of a quiet cul-de-...

  • 5 Beds
  • 5 Baths
  • Fawcett Gap Farm SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
175 Shields Dr, Winchester image
175 Shields Dr, Winchester $749,900 ▲

Beautiful 5 bedroom, 2.5-bath brick-front home situated on 2 private acres, offering the perfect blend of space, comfort, and recent updates. Shower on the main floor in...

  • 5 Beds
  • 4 Baths
  • Equestrian Estates SubDv.
  • 22602 Zip Code
  • ACTIVE Status
146 Stonebrook Rd, Winchester image
146 Stonebrook Rd, Winchester $649,900 ▼

Spacious ranch home on a beautiful 1-acre lot in the highly desirable Stonebrook Farms community! Surrounded by mature trees and offering a peaceful setting, this home co...

  • 5 Beds
  • 3 Baths
  • Stonebrook Farms SubDv.
  • 22602 Zip Code
  • ACTIVE Status
485 Lake Serene Dr, Winchester image
485 Lake Serene Dr, Winchester $969,000

A rare opportunity to live on Lake Serene - Welcome to your private lakefront retreat on Lake Serene, where lake-life meets timeless craftsmanship. Tucked among the trees...

  • 5 Beds
  • 4 Baths
  • Lake Serene SubDv.
  • 22603 Zip Code
  • ACTIVE Status
144 Morning Glory, Winchester image
144 Morning Glory, Winchester $499,000 ▼

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
  • ACTIVE 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
  • ACTIVE UNDER CONTRACT Status
102 Julie Ct, Winchester image
102 Julie Ct, Winchester $829,900 ▼

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 $714,000 ▼

Welcome to 342 Canyon Rd, a spacious and beautifully maintained home in the desirable Twin Lakes Overlook community on Winchester's east side close to Rt 7. Situated on a...

  • 5 Beds
  • 4 Baths
  • Twin Lakes Overlook SubDv.
  • 22602 Zip Code
  • ACTIVE Status
440 Canyon Rd, Winchester image
440 Canyon Rd, Winchester $549,000 ▼

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 $739,900 ▼

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
130 Wappinger Ter, Winchester image
130 Wappinger Ter, Winchester $489,990 ▼

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 $784,900 ▼

This beautiful, well-cared-for home occupies a peaceful setting overlooking a lake and stream directly behind the house. The well-stocked lake has an easily accessible w...

  • 5 Beds
  • 5 Baths
  • Twin Lake Overlook SubDv.
  • 22602 Zip Code
  • ACTIVE Status
303 Pembridge Dr, Winchester image
303 Pembridge Dr, Winchester $399,000

BACK ON MARKET and worth another look!!! NEW CARPET!!!! FRESH PAINT!!! NEW LIGHTING!! UPDATED Upstairs Bathrooms!!! (New photos coming soon).Discover the potential of th...

  • 5 Beds
  • 3 Baths
  • Pembridge Heights SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
206 Dogwood Rd, Winchester image
206 Dogwood Rd, Winchester $400,000 ▼

...NEW PRICE....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....

  • 5 Beds
  • 2 Baths
  • Shenandoah Hills SubDv.
  • 22602 Zip Code
  • PENDING Status
220 Lehigh, Winchester image
220 Lehigh, Winchester $665,000 ▼

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 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
660 Beehive Way, Winchester image
660 Beehive Way, Winchester $524,900 ▼

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
159 Abrams Pointe Blvd, Winchester image
159 Abrams Pointe Blvd, Winchester $749,900 ▼

***SELLER OFFERING UP TO $20,000 IN BUYER INCENTIVE TO USE TOWARD CLOSING COSTS OR INTEREST RATE BUYDOWN WITH AN ACCEPTABLE OFFER!!*** Better than new in coveted Abrams ...

  • 5 Beds
  • 5 Baths
  • Abrams Pointe SubDv.
  • 22602 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
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
107 Launchris Dr, Winchester image
107 Launchris Dr, Winchester $799,500 ▼

Looking for a home that gives you space, style, privacy, and the freedom to make it your own? Welcome to this stately Colonial set on nearly an acre of beautiful, private...

  • 5 Beds
  • 4 Baths
  • Dav Mar Village SubDv.
  • 22602 Zip Code
  • ACTIVE Status
219 Lehigh, Winchester image
219 Lehigh, Winchester $625,000 ▲

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 UNDER CONTRACT Status
Lot 10 Desant Cir, Winchester image
Lot 10 Desant Cir, Winchester $849,900 ▼

Four month build time from contract. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Appl...

  • 5 Beds
  • 3 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE 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 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!

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Anne Nouri

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