Winchester, VA Homes for Sale with Acreage

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  /53

  $799,900

  • 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 hosting

  Nicole Renzetti EXP Realty, LLC

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

  $639,900

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

  281 Light Rd, Winchester, VA 22603

  Please note that this weekend's open house has been moved to Sunday, 5/18 - 12-2pm. Serene Ranch-Style Retreat on Over 8 Acres in Frederick County, VAWelcome to your private oasis in the heart of Frederick County! Nestled on over 8 partially wooded acres along peaceful Light Road, this beautifully maintained ranch-style home (with a heated in-ground swimming pool and several out-buildings)

  Jennifer Watt Century 21 Redwood Realty

  281 Light Rd, Winchester, VA 22603
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  /49

  $280,000

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

  Mockingbird Lane Lot Unit WP007A, 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 Mockingbird Lane. Features a fully functional hunting cabin wired for a generator hook up with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters in

  Chad Pangle

  Mockingbird Lane Lot Unit WP007A, Winchester, VA 22603
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  /50

  $345,000

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

  Mockingbird Lane Lot Unit WP008, 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 Mockingbird 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

  Mockingbird Lane Lot Unit WP008, Winchester, VA 22603
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  /26

  $245,000

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

  Mockingbird Lane Lot Unit WP007, 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 Mockingbird 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

  Mockingbird Lane Lot Unit WP007, Winchester, VA 22603
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  /31

  $125,000

  • Land
  • 23 Acres
  • $5,383 per Acre

  0 Bear Trail Unit LotWP001 22365692, Winchester, VA 22602

  Idyllic, mostly wooded mountaintop sanctuary made up of three parcels with many residential and recreational possibilities. It is located just a few miles west of Winchester above Shawneeland. The large parcel is part of the Great North Mountain Wilderness community. The soil work on one of the small parcels is approved for a two-bedroom septic system, and the owner has stated that at one time,

  Chad Pangle Whitetail Properties Real Estate

  0 Bear Trail Unit LotWP001 22365692, Winchester, VA 22602
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  /32

  $58,999

  • Land
  • 6 Acres
  • $10,137 per Acre

  0 Pack Horse Rd Unit LotWP00E 21685367, Winchester, VA 22603

  BRAND NEW gravel entrance, road to homesite, and survey!!!! Attractive OWNER FINANCING terms available!!! Enjoy rural living and fun on this building lot in the Valley Estates community. This land is located off of Pack Horse Road not far from the West Virginia state line. This prime wooded lot perked for a 3 bedroom septic system just recently. Access is secured via road frontage on Pack Horse

  Chad Pangle Whitetail Properties Real Estate

  0 Pack Horse Rd Unit LotWP00E 21685367, 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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  /3

  $659,900

  • 4 Beds
  • 2.5 Baths
  • 3,160 Sq Ft

  683 Lake Saint Clair Dr, Winchester, VA 22603

  A rare find. House on Lake Saint Clair about 15 minutes from downtown Winchester. 35-acre lake and use of 175 acres, trails, hunting, and a shooting range. Lake St. Clair transfer fee of $5000.00 due at closing. Electric motorboats only, gasoline-powered boats are not allowed.

  John Schroth Colony Realty

  683 Lake Saint Clair Dr, Winchester, VA 22603
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  /68

  $700,000

  • 3 Beds
  • 3 Baths
  • 1,664 Sq Ft

  516 Merrimans Ln, Winchester, VA 22601

  Amazing Opportunity--First time on the market, this mid-century Ranch comes with updated bathrooms and custom kitchen. The 1.4 acre property includes an in-ground pool and guest house with full bath and kitchenette. Densely landscaped property provides almost complete privacy on one of the few remaining spacious lots inside the city. A large Lanai complements the property for entertaining or

  Dallas Croft Samson Properties

  516 Merrimans Ln, Winchester, VA 22601
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  /40

  $749,000

  • 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 flowing

  Lori Hoffman Realty ONE Group Old Towne

  200 Sweetbriar 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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  /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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  /51

  $839,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 4 Baths
  • 3,612 Sq Ft

  373 Greenfield Dr, Winchester, VA 22603

  PRICE IMPROVEMENT! Remodeled & renovated 4 bedroom, 4 full bath rambler, on 8+ manicured acres, has a fully finished lower level apartment with a separate entrance, an 1800 sq ft detached garage with a new propane HVAC system, a hydro pool, and charging station for your electric cars. This property checks all the boxes! The remodeled home features new plumbing and wiring throughout, including

  Jackie Douglass CENTURY 21 New Millennium

  373 Greenfield Dr, 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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  /51

  $720,000

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft

  881 Adams Rd, Winchester, VA 22603

  Welcome to this exquisite 3-bedroom, 2-bath rancher nestled on nearly 9 private acres, offering 2,250 square feet of refined living space and unmatched serenity. From the moment you enter, you'll be captivated by the elegance of rich wood floors, 9-foot ceilings, and exquisite crown molding with wide baseboards throughout. The great room is a true showstopper, featuring vaulted ceilings and a

  Kimberly Schroeder Long & Foster Real Estate, Inc.

  881 Adams Rd, Winchester, VA 22603
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  /73

  $719,000

  • 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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  /94

  $1,125,000

  • 4 Beds
  • 4 Baths
  • 4,949 Sq Ft

  1460 Pitcock Ln, Winchester, VA 22602

  This beauty includes three lots totaling 27.65 acres and only 10 minutes from Winchester City! This home exudes character from the moment you step in!Located in a secluded area with towering trees and a pond. This charming log cabin was moved to its current site in circa 1960, with a three-story addition built in 1994. The main cabin features exposed wooden beams and a cozy fireplace, offering

  Sheila Pack RE/MAX Roots

  1460 Pitcock Ln, Winchester, VA 22602
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  /104

  $1,115,000

  • 5 Beds
  • 7 Baths
  • 5,058 Sq Ft

  700 Miller Rd, Winchester, VA 22602

  Nestled in a highly desirable area, this stunning Colonial home offers timeless elegance on 2.5 private acres. Thoughtfully designed with both a main-level primary suite and an upper-level primary suite, 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 multiple living and

  Lilly Triplett Colony Realty

  700 Miller Rd, Winchester, VA 22602
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  /74

  $679,000

  • 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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  /44

  $679,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  146 Broomsedge Ln, Winchester, VA 22602

  Quality KEE Construction new build. Magnificent views on this private 5 acre lot. Driveway will be paved prior to closing. Daylight basement can be finished if you desire for $80 to $100 per sq ft depending on your choice of finish. Home is complete and ready to move in .

  Meridee Powars Link Realty Services LLC

  146 Broomsedge Ln, Winchester, VA 22602
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  /48

  $799,900 New Construction

  • 5 Beds
  • 3 Baths
  • 3,056 Sq Ft

  181 Oak Dr, Winchester, VA 22603

  Very private community all paved road. Close to town with wooded lots 10 minutes to town. 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 and laundry to be tile).

  Jim Thomson Realty ONE Group Old Towne

  181 Oak Dr, Winchester, VA 22603
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  /7

  $685,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 1,942 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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  /41

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  327 Bryarly Rd, Winchester, VA 22603

  Charming Countryside Cape Cod on a Meticulously Maintained 1.25 acres! Welcome to 327 Bryarly Drive, Winchester, VA 22603 – a beautifully updated Cape Cod-style home nestled on a serene and private half-acre lot. Originally built in 1941, this residence exudes countryside charm and character, while offering numerous modern upgrades.Step inside to discover 3 spacious bedrooms and 2 full baths,

  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

  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 fully functional homestead setup—ideal for those seeking rural charm with commuter convenience.The main

  Samantha Armel EXP Realty, LLC

  1080 Old Bethel Church Rd, Winchester, VA 22603
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  /28

  $499,000

  • Studio
  • 2,736 Sq Ft

  386 Round Hill Rd, Winchester, VA 22602

  ATTENTION INVESTORS!! *** 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 offered separately, and all for

  Bridget Aikens Colony Realty

  386 Round Hill Rd, Winchester, VA 22602
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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. There is an open feel to the main level which has a versatile floor plan. There is a sunroom, a family room & a kitchen with

  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 Mockingbird Lot 7 Ln Unit VAFV2034380, 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 Mockingbird 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 Mockingbird Lot 7 Ln Unit VAFV2034380, Winchester, VA 22603
• 

  

  /49

  $280,000

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

  0 Mockingbird Lot 7a Ln Unit VAFV2034376, 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 Mockingbird 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 Mockingbird Lot 7a Ln Unit VAFV2034376, Winchester, VA 22603
• 

  

  /50

  $345,000

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

  0 Mockingbird Lot 8 Ln Unit VAFV2034374, 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 Mockingbird 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 Mockingbird Lot 8 Ln Unit VAFV2034374, Winchester, VA 22603
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  /41

  $579,900

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

  1420 Fishel Rd, Winchester, VA 22602

  Tucked away on over 2.5 private, wooded acres, this beautifully updated home offers the ease of one-level living with incredible space inside and out. Featuring 3 bedrooms, 2 newly updated full baths, and brand-new luxury vinyl plank flooring throughout, the home blends comfort and style. The eat-in kitchen boasts an island, stainless steel appliances, and is filled with natural light. Enjoy the

  Katherine (Kat) Wetzel Century 21 Redwood Realty

  1420 Fishel Rd, Winchester, VA 22602
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  /59

  $469,900

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  1085 Greenwood Rd, Winchester, VA 22602

  MUST SEE!! Sellers have lived in this CHARMING meticulously well maintained 1968 brick ranch sitting on 1 ACRE for 27+ years!! 27 years’ of PURE LOVE and it shows. LOCATION, LOCATION! Rt 7, Rt 50, Interstate 81 & Costco only a 5 minute drive. Historic Downtown Winchester 10 mins. & Jim Barnett Park 5 mins!! Once a 3 Bed/1 Bath on a septic system is now a 2 Bedroom (one ensuite with jacuzzi tub)

  Caroline W. Barb, REALTOR Jim Barb Realty, Inc.

  1085 Greenwood Rd, Winchester, VA 22602
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  /53

  $500,000

  • 4 Beds
  • 2 Baths
  • 2,012 Sq Ft

  669 Dicks Hollow Rd, Winchester, VA 22603

  Welcome to this spacious farmhouse on FIVE acres! NEW TWO ZONE HEAT AND AC BEING INSTALLED ON TUESDAY THE 17TH! NEW hot water heater! NEWER windows throughout. Metal roof - large detached two car garage with large work area. Pole barn and garden shed! Apple trees, peach tree - 15 minutes to town!

  Barbera Clausen EXP Realty, LLC

  669 Dicks Hollow Rd, Winchester, VA 22603
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  /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
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  /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
• 

  

  /9

  $135,000

  • 1 Bed
  • 1 Bath

  1114 Cedar Grove Rd, Winchester, VA 22603

  Property has a great location but is probably a tear down. Health Documents available showing location of well/septic.

  Dave Spence RE/MAX Roots

  1114 Cedar Grove Rd, Winchester, VA 22603
• 

  

  /23

  $99,900

  • Land
  • 16 Acres
  • $6,283 per Acre

  LOT 11-HOOVER MTN Pack Horse Rd, Winchester, VA 22603

  Unique property, great for recreation. Land is all wooded, tall hardwoods, mostly mountainside. There is about 1.5 acres where Little Mountain Run (creek) runs through the property for over 300' so that you have a very flat, wooded area on the other side of the creek which is perfect for hiking, camping, hunting. You will have to visit the property to really appreciate what it has to offer.

  Edward Beightol Cedar Creek Real Estate

  LOT 11-HOOVER MTN Pack Horse Rd, Winchester, VA 22603
• 

  

  /41

  $540,000

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  129 Jalapa Trail, Winchester, VA 22602

  Brand new everything, Roof, appliances, water treatment , bathrooms, deck, Sunroom, flooring Motivated Seller The perfect retreat for everyone, Welcome to your dream home in the heart of the Virginia Mountains , yet only 7 miles to the new Medical Center in Winchester. The property has access to the community lake, picnic grounds, play ground and loads of nature trails for hiking and nature

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602

Showing Results 1 - 40, Page 1 of 3