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Winchester VA MLS Search

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View All Latest Winchester 5+ Acre Properties for Sale

Winchester image
Winchester $3,500,000

Be sure to see the video and 3D tour to fully explore this property! <br><br> Award-Winning Virginia Winery + Luxury Vineyard Estate + Income-Producing Luxury Short Term...

  • No SubDv.
  • 22603 Zip Code
  • ACTIVE Status
Tumble Leaf Lane, Winchester image
Tumble Leaf Lane, Winchester $805,000

CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Main Level Owners Suite floorplan the Box...

  • 4 Beds
  • 4 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
Off Mount Olive Rd, Winchester image
Off Mount Olive Rd, Winchester $1,120,000

Premier builder opportunity!!! Cluster of prime building lots conveniently located less than 10 minutes west of Winchester. Part of what was once the well known Rotz Farm...

  • 22603 Zip Code
  • ACTIVE Status
Off Of Mount Olive Rd, Winchester image
Off Of Mount Olive Rd, Winchester $210,000

Prime building lot conveniently located less than 10 minutes west of Winchester with immediate access to US-50 - Northwestern Pike. Part of what was once the well known R...

  • 22603 Zip Code
  • ACTIVE Status
1960 Siler Rd, Winchester image
1960 Siler Rd, Winchester $499,900

Looking for one-level living with acreage, a detached workshop/garage, RV/camper parking, and no HOA? Welcome to 1960 Siler Road, a custom-built ranch situated on 5 fence...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
Dominion Rd, Winchester image
Dominion Rd, Winchester $350,000

Open ground that is prime for investment, livestock or build your future home. Fully unrestriced, this property sits a long the Virginia/West Virginia border but calls Vi...

  • 22603 Zip Code
  • ACTIVE Status
236 Delmas Trl Trl, Winchester image
236 Delmas Trl Trl, Winchester $984,900

Nestled in the prestigious Midland Heights community, this exquisite Colonial-style residence offers a harmonious blend of luxury and comfort, set against a breathtaking ...

  • 4 Beds
  • 4 Baths
  • Midland Heights SubDv.
  • 22602 Zip Code
  • COMING SOON Status
531 Cedar Grove Rd, Winchester image
531 Cedar Grove Rd, Winchester $675,000

Discover a rare opportunity to own a piece of Frederick County history with this unique farmette property offering approximately 9.79 acres, a charming farmhouse, extensi...

  • 2 Beds
  • 1 Baths
  • Cedar Grove Road SubDv.
  • 22603 Zip Code
  • ACTIVE Status
TRACT 1: 152.44+/- ACRES Off Of Laurel Grove Rd, Winchester image
TRACT 1: 152.44+/- ACRES Off Of Laurel Grove Rd, Winchester $899,000

152± BEAUTIFUL ACRES IN WINCHESTER, VA! This outstanding property offers an incredible opportunity to build your dream home, cabin, or private retreat. The property featu...

  • 22602 Zip Code
  • ACTIVE Status
TRACT 2: 158.43+/- ACRES Laurel Grove Rd, Winchester image
TRACT 2: 158.43+/- ACRES Laurel Grove Rd, Winchester $899,000

158.43± BEAUTIFUL ACRES IN WINCHESTER, VA! This outstanding property offers an incredible opportunity to build your dream home, cabin, or private retreat. The property fe...

  • 22602 Zip Code
  • ACTIVE Status
479 Perry Rd, Winchester image
479 Perry Rd, Winchester $599,500

GREAT LOCATION CLOSE TO TOWN - 5 ACRES THAT POSSIBLY COULD BE SUBDIVIDED - HARDWOOD FLOORING - OPEN FLOOR PLAN - HAS A FLUE FOR WOOD OR PELLET STOVE - THIS PLACE IS READY...

  • 3 Beds
  • 2 Baths
  • None Available 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
4531 Back Mountain Rd, Winchester image
4531 Back Mountain Rd, Winchester $498,500

HUNTER’S PARADISE • 13.58 UNRESTRICTED ACRES!! Privacy, wildlife, outdoor adventure, and plenty of space—this home offers a rare opportunity to enjoy the peace and privac...

  • 4 Beds
  • 2 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
210 Jackson Dr, Winchester image
210 Jackson Dr, Winchester $800,000 ▲

Garage space like this is hard to find. Set on 10.05 private acres in Deerfield Estates, this all-brick rancher is anchored by a five-bay detached garage (garage lifts do...

  • 2 Beds
  • 3 Baths
  • Deerfield Estates SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1950 Jones Rd, Winchester image
1950 Jones Rd, Winchester $1,750,000

Tucked away on a private lane bordered by an elegant stone wall, this impressive all-brick residence offers approximately 8,000 square feet of exceptional living space in...

  • 4 Beds
  • 6 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • PENDING Status
144 Robinson Dr, Winchester image
144 Robinson Dr, Winchester $2,599,000

This upscale custom home blends clean, modern comfort with rustic charm—and does it sublimely with nearly 5,000 finished square feet on one level, including a separate in...

  • 4 Beds
  • 6 Baths
  • Roscommon SubDv.
  • 22602 Zip Code
  • ACTIVE Status
3150 Apple Pie Ridge Rd, Winchester image
3150 Apple Pie Ridge Rd, Winchester $575,000

<p> Located on highly desired Apple Pie Ridge Road with fabulous scenic mountain VIEWS, HORSES ARE ALLOWED at this charming split-foyer home offers over 2,500 finished sq...

  • 3 Beds
  • 3 Baths
  • White Hall SubDv.
  • 22603 Zip Code
  • ACTIVE Status
2216 Laurel Grove Rd, Winchester image
2216 Laurel Grove Rd, Winchester $1,300,000

Welcome to 2216 Laurel Grove Rd, an exceptional custom-built modern farmhouse offering privacy, beautiful views, and relaxed country living on 30 unrestricted acres, all ...

  • 4 Beds
  • 3 Baths
  • None Available 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
0 Perry Road, Winchester image
0 Perry Road, Winchester $189,900

10 min or less into Winchester City, discover the possibilities on this beautiful 5-acre parcel, offering a peaceful mix of mature woods, open clearing areas, a creek, an...

  • 22602 Zip Code
  • ACTIVE Status
194 Glendobbin Ln, Winchester image
194 Glendobbin Ln, Winchester $1,350,000

Welcome to an extraordinary custom-built all-brick estate nestled on five beautifully manicured acres in the highly sought-after Apple Pie Ridge area. This exceptional pr...

  • 4 Beds
  • 4 Baths
  • Glendobbin Hills SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
2122 Jones Road, Winchester image
2122 Jones Road, Winchester $749,900 ▼

Beautifully renovated 1918 farmhouse situated on 10 scenic acres with views of Opequon Creek, accessible creek frontage, a picturesque pond, and some fenced acreage. Conv...

  • 3 Beds
  • 3 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE Status
Wolf Spring Trl, Winchester image
Wolf Spring Trl, Winchester $127,750

Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist wi...

  • Shawneeland SubDv.
  • 22602 Zip Code
  • ACTIVE Status
2630 Hunting Ridge Rd, Winchester image
2630 Hunting Ridge Rd, Winchester $900,000

Striking modern farmhouse-style home built in 2009, set on 15.14 private acres. Offering 2,475 finished square feet above grade plus 540 finished square feet on the lower...

  • 3 Beds
  • 5 Baths
  • Creek View Farms SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
1480 Chestnut Grove Rd, Winchester image
1480 Chestnut Grove Rd, Winchester $375,000

Enjoy one-level living with 6.44 partly wooded acres. All-brick 3-bedroom, 1-bath home offering a peaceful country setting with plenty of room to enjoy the outdoors. Rela...

  • 3 Beds
  • 1 Baths
  • Three Creek Knolls SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
Brush Creek Rd, Winchester image
Brush Creek Rd, Winchester $300,000

Discover the possibilities with this beautiful 20.2-acre property offering the perfect blend of privacy, natural beauty, and opportunity. Featuring a mix of mature woods ...

  • 22603 Zip Code
  • ACTIVE Status
450 Green Spring Rd, Winchester image
450 Green Spring Rd, Winchester $3,500,000

Be Sure to View the Video and 3D Tour to Fully Experience this Stunning Property <br><br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one ...

  • 3 Beds
  • 4 Baths
  • No SubDv.
  • 22603 Zip Code
  • ACTIVE Status
450 Green Spring Rd, Winchester image
450 Green Spring Rd, Winchester $3,500,000

Be sure to see the video and 3D tour to fully explore this property! <br><br> Award-Winning Virginia Winery + Luxury Vineyard Estate + Income-Producing Luxury Short Term...

  • 3 Beds
  • 4 Baths
  • No SubDv.
  • 22603 Zip Code
  • ACTIVE Status
2760 Wardensville Grade, Winchester image
2760 Wardensville Grade, Winchester $164,999 ▼

Discover this 5-acre residential lot in the Winchester area of Frederick County, Virginia. Featuring gently sloped, wooded terrain, the property offers a peaceful natural...

  • Canter Estates L-313 SubDv.
  • 22602 Zip Code
  • ACTIVE Status
582 Miller Rd, Winchester image
582 Miller Rd, Winchester $1,650,000

Built in 1774, before America was America, this remarkable 31-acre estate has stood through the birth of a nation, and today it's ready for its next chapter. This is his...

  • 4 Beds
  • 5 Baths
  • Belleville Farm SubDv.
  • 22602 Zip Code
  • ACTIVE Status
341 Laurel Grove Rd Unit #LOT 4 ROAD FRONT, Winchester image
341 Laurel Grove Rd Unit #LOT 4 ROAD FRONT, Winchester $250,000

THERE ARE 2 -5 ACRE BUILDING LOTS W/4 BR CONVENTIONAL PERKS APPROVED. LOT 3 IS UP ON THE HILL AND LOT 4 FRONTS THE ROAD. THESE LOTS ARE CREATED FROM A LARGER PARCEL BY ...

  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
Light Rd, Winchester image
Light Rd, Winchester $959,000

Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning...

  • 3 Beds
  • 3 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
Light Rd, Winchester image
Light Rd, Winchester $959,000

Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning...

  • 3 Beds
  • 3 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
3764 Northwestern Pike, Winchester image
3764 Northwestern Pike, Winchester $715,000 ▼

RARE FIND! Discover the freedom and possibilities that come with 12.17 wooded acres—no HOA, no restrictions, just endless opportunity. Whether you're dreaming of creating...

  • 4 Beds
  • 3 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
730 Merrimans Ln, Winchester image
730 Merrimans Ln, Winchester $3,175,000

A Once-in-a-Generation Opportunity: 1765 Heritage Meets Modern Luxury Rarely does a property of this caliber, history, and scale become available within Winchester city ...

  • 6 Beds
  • 7 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
48 W Boscawen, Winchester image
48 W Boscawen, Winchester $1,724,000

Beautifully restored and fully modernized mixed-use building in the heart of historic Winchester. This exceptional offering includes a fully leased commercial building wi...

  • Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
135 & 171 Bufflick Rd, Winchester image
135 & 171 Bufflick Rd, Winchester $825,000 ▼

A rare commercial development opportunity awaits at 135 & 171 Bufflick Road, featuring nearly 8 acres of prime, strategic real estate in Winchester. Perfectly positioned ...

  • 22602 Zip Code
  • ACTIVE Status
341 Laurel Grove Rd Unit #LOTS 3 AND 4, Winchester image
341 Laurel Grove Rd Unit #LOTS 3 AND 4, Winchester $250,000 ▼

THERE ARE 2 -5 ACRE BUILDING LOTS W/4 BR CONVENTIONAL PERKS APPROVED. LOT 3 IS UP ON THE HILL AND LOT 4 FRONTS THE ROAD. THESE LOTS ARE CREATED FROM A LARGER PARCEL BY ...

  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
Pack Horse Road Lot C, Winchester image
Pack Horse Road Lot C, Winchester $110,000

The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 6.42 lot C is wooded, has septic al...

  • 22603 Zip Code
  • ACTIVE Status
Pack Horse Road Lot B, Winchester image
Pack Horse Road Lot B, Winchester $89,000

The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 5 acre lot B is wooded, has an old...

  • 22603 Zip Code
  • ACTIVE Status
Pack Horse Road Lot A, Winchester image
Pack Horse Road Lot A, Winchester $89,000

The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 6.11 lot A is wooded, has a Freder...

  • 22603 Zip Code
  • ACTIVE Status
TWO LOTS ON Siler Rd, Winchester image
TWO LOTS ON Siler Rd, Winchester $139,900

In the Gainesboro area of Frederick County, VA, offered here are (2) 10 acre lots with unique characteristics. The land is within the Rhine Forest Estates "subdivision" ...

  • Rhine Forest Estates SubDv.
  • 22603 Zip Code
  • ACTIVE Status
170 Mountain View Ct, Winchester image
170 Mountain View Ct, Winchester $439,900

Charming 3-bedroom, 1.5-bath colonial home on 5 acres, with an additional 7 acres available. Nestled in nature, it features a detached 2-car garage with power and lights,...

  • 3 Beds
  • 2 Baths
  • Chestnut Grove Estates SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
117 Glen Ridge Rd, Winchester image
117 Glen Ridge Rd, Winchester $599,000 ▼

Welcome to 117 Glen Ridge Road! Discover the perfect blend of privacy, space, and convenience on 6.65 beautiful wooded acres just minutes from Winchester. Tucked away in ...

  • 3 Beds
  • 4 Baths
  • High View Manor SubDv.
  • 22602 Zip Code
  • ACTIVE Status
Lot 5 Snake, Winchester image
Lot 5 Snake, Winchester $190,000 ▼

Build Your Ultimate Private Sanctuary on Hoover Mountain Retreat!Escape the noise and embrace the serene beauty of the Virginia countryside on this magnificent 17.8-acre ...

  • 22603 Zip Code
  • ACTIVE Status
3105 Apple Pie Ridge Rd, Winchester image
3105 Apple Pie Ridge Rd, Winchester $699,999

Situated on a beautiful tract of land with scenic views in every season, this charming farmhouse offers the space, tranquility, and rural lifestyle that buyers dream abou...

  • 4 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
300 Tavistock Dr, Winchester image
300 Tavistock Dr, Winchester $899,990 ▼

Discover the perfect blend of space, privacy and convenience this expansive 3500 sq ft plus ranch home situated on 7.12 beautiful acres. Located just 10 mins from shoppin...

  • 4 Beds
  • 4 Baths
  • Tavistock Estates SubDv.
  • 22602 Zip Code
  • ACTIVE Status
3336 Hunting Ridge Rd, Winchester image
3336 Hunting Ridge Rd, Winchester $539,000 ▼

Colonial home 21 yrs young on 5 acres in Frederick county 4 bedroom 2 full baths with 1 half bath ., Whole house freshly painted in Jan/Feb 2025, laundry on main level ...

  • 4 Beds
  • 3 Baths
  • Chestnut Grove Estates SubDv.
  • 22603 Zip Code
  • ACTIVE Status
Shockeysville Road, Winchester image
Shockeysville Road, Winchester $475,000

Approximately 90-acre wooded parcel offering abundant space for recreation, hunting, and enjoying nature, with Little Brush Creek bordering the property. This private ret...

  • 22603 Zip Code
  • ACTIVE Status
Four Wheel Dr, Winchester image
Four Wheel Dr, Winchester $79,900

All wooded in private area with other nice homes. About 30 minutes south west of hospital, Wal-Mart. No HOA that allows you to do anything with your property. Older 3BR P...

  • 22602 Zip Code
  • ACTIVE Status

5+ Acres Winchester Real Estate

Our website features the best real estate search for 5+ acre 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

keller william luxury
1.888.840.5553
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