Winchester, VA Homes for Sale with Acreage

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  /46

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 2,859 Sq Ft

  247 Mcguire Rd, Winchester, VA 22603

  Tucked away on a private 2.7-acre wooded lot, this stunning all-brick colonial has been fully renovated from top to bottom. Inside, 3/4" solid ash, 5"wide herringbone flooring flows throughout, accented by designer lighting, crown molding, and elegant chair rail trim. The chef’s kitchen is a true showstopper—featuring a massive island, striking white and gold appliances, and custom finishes. The

  

  Lori Bales

  Keller Williams Realty

  (540) 701-5541

  247 Mcguire Rd, Winchester, VA 22603
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  Explore Winchester

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  /41

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  1420 Fishel Rd, Winchester, VA 22602

  Nestled away in the trees, this updated retreat on 2.67 acres offers the perfect blend of peace, privacy, and one-level living. Inside, you’ll find 3 bedrooms, 2 renovated baths, brand-new flooring, and fresh paint throughout. The bright eat-in kitchen with island and stainless appliances flows into a spacious sitting room, enclosed rear porch with A/C, and a covered front porch for year-round

  

  Katherine (Kat) Wetzel

  Century 21 Redwood Realty

  (540) 779-1383

  1420 Fishel Rd, Winchester, VA 22602
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  /34

  $870,000

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  601 Fall Run Ln, Winchester, VA 22602

  Prepare to be captivated by the beauty and tranquility of this exceptional custom-built home, nestled on 20.10 acres with breathtaking mountain views. Offering desirable one-level living, this nearly new (under 3 years old) home boasts a gorgeous covered porch and an expansive deck perfect for savoring the stunning surroundings.Step inside to discover a meticulously designed open-plan

  Theo Theologis Slones Real Estate

  601 Fall Run Ln, Winchester, VA 22602
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  /53

  $774,900

  • 5 Beds
  • 3.5 Baths
  • 3,928 Sq Ft

  977 W Parkins Mill Rd, Winchester, VA 22602

  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

  977 W Parkins Mill Rd, Winchester, VA 22602
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  /56

  $619,900

  • 3 Beds
  • 2.5 Baths
  • 1,968 Sq Ft

  281 Light Rd, Winchester, VA 22603

  Century 21 Redwood Realty makes no representation as to the accuracy or reliability of information provided in the listing. Buyer should verify information provided, that is material to the Buyer’s decisions, as they relate to this property. Any provided documents should be researched and verified. ** Price Improvement!! Property previously appraised for just under $647,000! Now

  Jennifer Watt Century 21 Redwood Realty

  281 Light Rd, Winchester, VA 22603
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  /23

  $168,000

  • Land
  • 10 Acres
  • $16,800 per Acre

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602

  Enjoy rural living and fun on this building lot in the Long Ridge Estates community. This prime building lot is located off of Gough Road in the High View Manor area of the county. This parcel has a septic certification letter on record with the county health department for a four-bedroom septic system. Access is secured via a 50 ft deeded access easement, which has already been installed and

  Chad Pangle Whitetail Properties Real Estate

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602
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  /50

  $685,000

  • 4 Beds
  • 2.5 Baths
  • 2,998 Sq Ft

  441 Fair Ln, Winchester, VA 22603

  Discover your perfect retreat at 441 Fair Ln, Winchester, VA 22603, in the peaceful Fairway Estates neighborhood! This stunning 4-bedroom, 2.5-bathroom single-family home spans 2,998 square feet on a sprawling 5.54-acre lot, offering a blend of modern luxury and serene country living. Built in 2000, this meticulously updated residence is just minutes from Historic Downtown Winchester and major

  Caleb Fowler Samson Properties

  441 Fair Ln, Winchester, VA 22603
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  /40

  $939,950

  • 5 Beds
  • 6.5 Baths
  • 4,301 Sq Ft

  254 Whistlewood Ln, Winchester, VA 22602

  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

  254 Whistlewood Ln, Winchester, VA 22602
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  /63

  $849,990

  • 4 Beds
  • 3.5 Baths
  • 3,942 Sq Ft

  756 Brookneil Dr, Winchester, VA 22602

  Some homes are lived in. Others are lived for. This one? It's the kind of place you wait for—the kind you watch for, and when it finally hits the market, you clear your calendar to see it.Set deep into over 9 private wooded acres, at the very end of a quiet cul-de-sac, this completely rebuilt ranch-style home in Winchester offers something you rarely find anymore: total privacy, modern

  Alexander Bracke Real Broker, LLC

  756 Brookneil Dr, Winchester, VA 22602
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  /107

  $799,900

  • 4 Beds
  • 3.5 Baths
  • 5,161 Sq Ft

  132 Wilton Dr, Winchester, VA 22603

  Beautifully Conceived Custom Colonial on 2.59 manicured acres with mature trees and landscaping. Versatile floor plan with Main Floor Primary and generous room sizes for elegant one level living, complemented by multiple bedrooms above and a fully finished basement--possible in-law suite with level walkout. Large composite deck features a screened gazebo and overlooks beautiful patio with stone

  Dallas Croft Samson Properties

  132 Wilton Dr, Winchester, VA 22603
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  /86

  $669,900

  • 4 Beds
  • 3 Baths
  • 3,442 Sq Ft

  121 Sweetbriar Ln, Winchester, VA 22603

  "Private haven Rancher" on 13 plus acres with 4 Bedrooms and 3 full baths. Hardwood floors throughout home. See-thru Fireplace between Dining room and Living room. Recent upgraded kitchen with new flooring ,counter tops and fresh paint. Owners' Suite has bathroom w/whirlpool tub, separate shower, double sinks and French door access to the rear deck. Finished basement with full bath, bedroom,

  Andrew Hensley Samson Properties

  121 Sweetbriar Ln, Winchester, VA 22603
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  /72

  $695,000

  • 5 Beds
  • 4 Baths
  • 4,387 Sq Ft

  3949 N Frederick Pike, Winchester, VA 22603

  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

  3949 N Frederick Pike, Winchester, VA 22603
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  /40

  $699,900

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  200 Sweetbriar Ln, Winchester, VA 22603

  Welcome to your dream escape! This custom-built cabin on 7.02 acres in Winchester, VA offers the perfect blend of peace, privacy, and high-end living. Whether you're seeking a serene getaway or a functional farmette, this property has it all — with a mix of open pasture and woods, it’s ideal for animals, gardening, or simply soaking in nature.Step inside to find gleaming hardwood floors

  Lori Hoffman Realty ONE Group Old Towne

  200 Sweetbriar Ln, Winchester, VA 22603
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  /13

  $910,000

  • 2 Beds
  • 1 Bath
  • 609 Sq Ft

  196 Hodges Ln, Winchester, VA 22603

  Incredible Builder or Private Estate Opportunity on Nearly 80 Acres!This 79.16-acre property, located less than 15 miles from Winchester, offers the perfect blend of rural seclusion and convenient access. Tucked away in a peaceful setting, this land presents a rare opportunity for developers to build 7+ homes, or for an individual to create a private dream retreat surrounded by nature. The

  Sarah Reynolds Keller Williams Realty

  196 Hodges Ln, Winchester, VA 22603
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  /42

  $769,900

  • 3 Beds
  • 3 Baths
  • 2,112 Sq Ft

  1049 Laurel Grove Rd, Winchester, VA 22602

  Nestled at the end of a peaceful cul-de-sac, this stunning, property offers the perfect blend of seclusion and community living. This custom-designed home offers three bedrooms and three bathrooms, with the convenience of main-level living. Surrounded by lush woodlands and boasting breathtaking views of both trees and mountains, this property is ideal for those seeking a tranquil retreat that

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
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  /72

  $699,000

  • 4 Beds
  • 4.5 Baths
  • 4,320 Sq Ft

  292 Green Spring Rd, Winchester, VA 22603

  Welcome to your dream home! Nestled on just over 5 serene acres, this beautifully maintained 4-bedroom, 4.5-bathroom property offers the perfect blend of comfort, style, and functionality. From the moment you arrive, you’ll be charmed by the picturesque country and mountain views and the orchard-like feel created by numerous fruit trees (peaches, pears, apples, and cherries) lining the front

  Katie Landi Jordan Samson Properties

  292 Green Spring Rd, Winchester, VA 22603
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  /74

  $669,000

  • 4 Beds
  • 3.5 Baths
  • 3,008 Sq Ft

  355 Fishel Rd, Winchester, VA 22602

  Experience the epitome of homeownership with this stunning colonial home property perfectly set on 2.5+ acres of serene land just moments from all the conveniences of town. Offering the perfect blend of classic charm and modern amenities, this home is ideal for those seeking privacy without sacrificing accessibility. Thoughtfully designed with generous living spaces. Upon entering, you're greeted

  Daniel Brereton RE/MAX Roots

  355 Fishel Rd, Winchester, VA 22602
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  /77

  $765,000

  • 4 Beds
  • 3.5 Baths
  • 3,504 Sq Ft

  3980 Middle Rd, Winchester, VA 22602

  Custom, all-brick white rambler with a French Country ambience, enjoys boundaries of a lovely brook and a berm of boulders and indigenous plantings that obscures property from the roadway. All rooms are generously sized with the main level suitable for one-level living with Primary bedroom and laundry. Bedrooms on upper level are large enough for additional sitting area or study furnishings.

  Dallas Croft Samson Properties

  3980 Middle Rd, Winchester, VA 22602
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  /25

  $749,900 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,368 Sq Ft

  lot 7 Redbud Rd, Winchester, VA 22603

  Another quality home offered by H&H Builders Inc. Easy access to Winchester, I81 and Rt 7 for commuting. Open/flexible floor plan with room to roam! Kitchen features huge island and all the amenities. Ex Large covered rear deck for entertaining. See example pictures and standard features sheet as they would be upgrades for many others. VDOT road and no HOA. Water treatment system now included

  Jim Thomson Realty ONE Group Old Towne

  lot 7 Redbud Rd, Winchester, VA 22603
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  /4

  $679,900 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,333 Sq Ft

  1153 Merrimans Ln, Winchester, VA 22602

  Nice Cape Cod coming soon - custom built - one owner home. Over 2 acres next to Roscommons. Great location. Full unfinished basement. 3 bedrooms, 2.5 baths - bonus room. Selling As Is. Over 2 acres - 5 minutes to Winchester Med Center. Professional photos coming soon.

  Traci Shoberg RE/MAX Roots

  1153 Merrimans Ln, Winchester, VA 22602
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  /2

  $750,000 Coming Soon

  • 5 Beds
  • 3.5 Baths
  • 4,144 Sq Ft

  108 Katie Ln, Winchester, VA 22602

  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

  108 Katie Ln, Winchester, VA 22602
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  /15

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  1399 Chestnut Grove Rd, Winchester, VA 22603

  One Level home on a private 5 acre lot. Bring your horses, goats, chickens - this is the perfect farmette! Absolutely beautiful setting that includes a paddock and a barn/shed. New roof April 2025. New Laminate flooring in kitchen. Only 10 minutes from downtown Winchester and convenient to grocery, farmers’ markets, and the hospital. House is full of character and has an open floor plan! The

  Emma Kerns MarketPlace REALTY

  1399 Chestnut Grove Rd, Winchester, VA 22603
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  /10

  $250,000

  • Land
  • 20 Acres
  • $12,469 per Acre

  951 Bobcat Trail, Winchester, VA 22602

  Breathtaking Views and Endless Possibilities!Discover your own slice of paradise on this stunning 20.05-acre property! With a 3-bedroom perc already in place, drainfield and distribution box installed, and electric at the property, you're just a septic tank away from breaking ground. Part of the lot is already cleared, making it the perfect spot to build your dream home, weekend getaway, or

  Sharon Farinholt Realty ONE Group Old Towne

  951 Bobcat Trail, Winchester, VA 22602
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  /52

  $650,000

  • 6 Beds
  • 3 Baths
  • 2,568 Sq Ft

  1301 Front Royal Pike, Winchester, VA 22602

  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.

  1301 Front Royal Pike, Winchester, VA 22602
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  /78

  $1,300,000

  • 5 Beds
  • 4.5 Baths
  • 5,117 Sq Ft

  325 Windsor Ln, Winchester, VA 22602

  Welcome to 325 Windsor Lane, a stately brick Georgian-style home on 5 open and wooded acres in Winchester’s desirable Long Meadows community. This timeless residence offers privacy, serenity, and refined indoor-outdoor living just minutes from Winchester. Inside, the gourmet kitchen is a culinary showpiece featuring 36" custom cabinetry, granite countertops, two Sub-Zero refrigerators, a

  Sherry Pullen Weichert Realtors - Blue Ribbon

  325 Windsor Ln, Winchester, VA 22602
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  /70

  $599,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  251 Heather Hill Ln, Winchester, VA 22603

  Priced below appraised value! Have you been looking for peace and serenity, then you've found it. This gorgeous property offers 10 acres (there are two different parcels included in this sale. Parcels that are included are: 19-3-7 (house parcel, 5 acres), and 19-3-10 (garage, pole barn parcel, 5 acres) The lovely Chalet offers 3 bedrooms and 2 full bathrooms. The main level of the home

  Amber Jenkins Century 21 Redwood Realty

  251 Heather Hill Ln, Winchester, VA 22603
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  /52

  $608,000

  • 3 Beds
  • 2.5 Baths
  • 2,268 Sq Ft

  224 Vine Ln, Winchester, VA 22602

  Welcome to 224 Vine Lane – A Rare Gem in Winchester!Situated on a beautifully landscaped lot with fantastic curb appeal, this updated Cape Cod offers timeless charm, spacious living, and exciting potential with an additional building lot included in the sale!Step inside to discover large, light-filled rooms, a functional layout, and tasteful updates throughout. The main level boasts

  Tracie Clawson ERA Oakcrest Realty, Inc.

  224 Vine Ln, Winchester, VA 22602
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  /51

  $1,195,000

  • 7 Beds
  • 4.5 Baths
  • 6,380 Sq Ft

  207 Westview Dr, Winchester, VA 22603

  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

  207 Westview Dr, Winchester, VA 22603
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  /8

  $1,400,000

  • Land
  • 6 Acres
  • $244,328 per Acre

  1667 N Frederick Pike, Winchester, VA 22603

  Great highway exposure exposure to state route 37 the bypass around the West side of Winchester and and 5222 north or North Frederick Pike entrance at a signalized intersection

  John Scully Colony Realty

  1667 N Frederick Pike, Winchester, VA 22603
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  /41

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,165 Sq Ft

  327 Bryarly Rd, Winchester, VA 22603

  Charming Countryside Cape Cod on a Meticulously Maintained 1.25 acres! Motivated seller! Welcome to 327 Bryarly Drive, Winchester, VA 22603 – a beautifully updated Cape Cod-style home nestled on a serene and private 1.25 Acre lot. Originally built in 1941, this residence exudes countryside charm and character, while offering numerous modern upgrades.Step inside to discover 3 spacious

  Lisa Behr Coldwell Banker Premier

  327 Bryarly Rd, Winchester, VA 22603
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  /56

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,581 Sq Ft

  1080 Old Bethel Church Rd, Winchester, VA 22603

  Notice: Private Property/Working Homestead, Do NOT enter/walk property without appointment. Turnkey Homestead on 5+ Acres | Updated 4BR Home with Farm InfrastructureWelcome to this versatile and well-maintained property located in the pastoral countryside of Frederick County, VA. Situated on 5.07 acres, this 4-bedroom, 3.5-bath home offers modern updates, flexible living spaces, and a

  Samantha Armel EXP Realty, LLC

  1080 Old Bethel Church Rd, Winchester, VA 22603
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  /52

  $300,000

  • 2 Beds
  • 4 Baths
  • 2,438 Sq Ft

  102 Duwamish Trail, Winchester, VA 22602

  If you are looking for a home with privacy and a peaceful rural feel but only 15 minutes to Winchester then this home is for you! Set in a natural habitat, 102 Duwamish Trail has a vintage feel and could be a weekend getaway or your primary residence away from the city. No HOA! There is an open feel to the main level which has a versatile floor plan. There is a sunroom, a family room & a

  Dorothy Beach Samson Properties

  102 Duwamish Trail, Winchester, VA 22602
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  /26

  $245,000

  • Land
  • 23 Acres
  • $10,452 per Acre

  0 Easter Ridge Lot 7 Ln, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Easter Ridge Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. There are potential building sites located throughout the

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Easter Ridge Lot 7 Ln, Winchester, VA 22603
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  /49

  $280,000

  • Land
  • 25 Acres
  • $11,129 per Acre

  0 Easter Ridge Lot 7a Ln, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Easter Ridge Lane. Features a fully functional hunting cabin wired for a generator hook up with propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters in an attached

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Easter Ridge Lot 7a Ln, Winchester, VA 22603
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  /50

  $345,000

  • Land
  • 40 Acres
  • $8,582 per Acre

  0 Easter Ridge Lot 8 Ln, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Easter Ridge Lane. Features a fully functional hunting cabin with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters via a loft. Experience exciting

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Easter Ridge Lot 8 Ln, Winchester, VA 22603
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  /56

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,937 Sq Ft

  442 Frog Hollow Rd, Winchester, VA 22603

  Nestled in the serene Frog Hollow Estates, this charming Colonial home offers a perfect blend of comfort and functionality. With four spacious bedrooms and 2.5 bathrooms, the interior is designed for modern living. The traditional floor plan flows seamlessly into a family room off the kitchen, creating a warm atmosphere for entertaining. Step outside to discover 16 acres of picturesque land,

  Wendy Conner Coldwell Banker Premier

  442 Frog Hollow Rd, Winchester, VA 22603
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  /28

  $475,000

  • 6 Beds
  • 3 Baths
  • 2,736 Sq Ft

  386 Round Hill Rd, Winchester, VA 22602

  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

  386 Round Hill Rd, Winchester, VA 22602
• 

  

  /6

  $4,000,000

  • Land
  • 27 Acres
  • $147,059 per Acre

  0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603

  Unprecedented Development Opportunity, County of Frederick, 27.2 acres in land use plan for high density rezoning (RP) and development (currently zoned RA, will require rezoning). Ideal townhouse and apartment project. Gateway to downtown Old Town Winchester. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1

  Gillian Greenfield Coldwell Banker Premier

  0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603
• 

  

  /6

  $4,500,000

  • Land
  • 11 Acres
  • $393,701 per Acre

  801 Fairmont Ave, Winchester, VA 22601

  Unprecedented Development Opportunity, City of Winchester, 10.34 acres plus 3 SFH fronting Fairmont Ave (additional 1.09 acres). Gateway to downtown Old Town Winchester. Prime location for high density multifamily and mixed use commercial. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1 Main Street and Places

  Gillian Greenfield Coldwell Banker Premier

  801 Fairmont Ave, Winchester, VA 22601
• 

  

  /71

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  251 Heather Hill Ln, Winchester, VA 22603

  Back on market at NO fault of seller. Have you been looking for peace and serenity, then you've found it. This gorgeous property offers almost 50 acres (there are several different parcels included in this sale. Parcels that are included are: 19-3-7 (house parcel, 5 acres), 19-3-10 (garage, pole barn parcel, 5 acres), 19-3-12 (7.79 acres), 19-A-48 (31.04 acres). The lovely Chalet offers 3

  Amber Jenkins Century 21 Redwood Realty

  251 Heather Hill Ln, Winchester, VA 22603

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