Homes for Sale near The Independent School of Winchester

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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
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  /18

  $355,000

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft

  2940 Grace St, Winchester, VA 22601

  Welcome to your charming Cape Cod retreat! Built in 1955, this delightful 3-bedroom, 1-bath home offers a warm and inviting atmosphere—perfect for anyone looking for a cozy and welcoming place to call home. --- Step inside to a thoughtfully designed layout that makes the most of the 936 square feet of finished living space. --- Home is equipped with energy-efficient solar panels to help reduce

  Lauren Smith-Washbourne Coldwell Banker Premier

  2940 Grace St, Winchester, VA 22601
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  /40

  $359,900

  • 3 Beds
  • 2.5 Baths
  • 1,466 Sq Ft

  124 Wilkins Dr, Winchester, VA 22602

  Welcome home to this newly remodeled and upgraded ranch style home. All the convenience of one level living, with the option of a basement full of possibilities. Step into the spacious living room, complete with fireplace, as you walk in the front door. Continue through the wonderful flow of the house into the dining room and open kitchen. Enjoy making your meals in the fully renovated kitchen

  Dave Spence RE/MAX Roots

  124 Wilkins Dr, Winchester, VA 22602
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  /17

  $235,000

  • Land
  • 0.36 Acre
  • $652,778 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  Introducing a newly configured Winchester City lot ready for you to build your dream home! The heavy lifting has already been done. The current owner worked with the neighbors and the City to widen the lot to accommodate a sizable home. With a width of approximately 100 feet you will have plenty of space to spread out. Located on a storied street in downtown Winchester, you will enjoy the perks

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
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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
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  /41

  $310,000

  • 5 Beds
  • 2 Baths
  • 1,152 Sq Ft

  601 Grove St, Winchester, VA 22601

  601 Grove Street, is a single-family home offering a blend of comfort and convenience. Built in 1980, this 1,152 sq ft ranch-style residence features 3 bedrooms and 1 full bath on the main level, complemented by a partially finished basement that includes an additional bathroom and laundry area. The basement also offers versatile spaces that can serve as extra bedrooms, an office, or a recreation

  Lilly Triplett Colony Realty

  601 Grove St, Winchester, VA 22601
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  /29

  $399,000

  • 5 Beds
  • 2 Baths
  • 2,186 Sq Ft

  214 S Braddock St, Winchester, VA 22601

  This property is currently zoned as fully commercial but has the potential to be changed to: Mixed Use or Fully Residential with proper city approval. Additional information from city located in documents. This home will need a Kitchen.Situated in Downtown Winchester, 214 S Braddock is waiting for your ideas! Built in 1865, this home features historic charm including exposed brick walls,

  Matt Leiva Keller Williams Realty

  214 S Braddock St, Winchester, VA 22601
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  /35

  $665,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  112 W Germain St, Winchester, VA 22601

  100-Year-Old Downtown Winchester Charmer – Brought Back to Life in 2025!This beautifully restored century-old home has been completely reimagined from the ground up, blending timeless character with top-tier modern upgrades. Located in the heart of historic downtown Winchester, this home underwent a full-gut renovation in 2025—everything is new. From the all-new electrical wiring and replaced

  Amanda Magana RE/MAX Roots

  112 W Germain St, Winchester, VA 22601
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  /67

  $615,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

  Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
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  /28

  $189,000

  • 2 Beds
  • 1 Bath
  • 644 Sq Ft

  792 Fox Dr, Winchester, VA 22603

  Charming 2-bedroom, 1-bath bungalow featuring hardwood floors in the living room and both bedrooms. The exterior has been freshly painted, giving the home a clean, updated look. Conveniently located near shopping and major highways, making commuting easy. Recent updates within the last 2.5 years include a new roof and replacement of most windows. A great opportunity with key improvements already

  Amanda Gulla Preslee Real Estate

  792 Fox Dr, Winchester, VA 22603
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  /85

  $1,125,000

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

  1460 Pitcock Ln, Winchester, VA 22602

  Escape to Your Private Retreat – Just 10 Minutes from Winchester!Don’t miss the 3D tour attached to this listing!Welcome to a truly one-of-a-kind property offering 27.65 secluded acres across three parcels, complete with towering trees, a tranquil pond, and breathtaking natural surroundings. This charming log home is rich with character and history—originally relocated here in the

  Sheila Pack RE/MAX Roots

  1460 Pitcock Ln, Winchester, VA 22602
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  /76

  $350,000

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  2431 Cedar Creek Grade, Winchester, VA 22602

  This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in

  Edward Beightol Cedar Creek Real Estate

  2431 Cedar Creek Grade, Winchester, VA 22602
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  /24

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  16 W Clifford St, Winchester, VA 22601

  Wooden construction, Alley side home ready for construction. Boarders Downton Winchester, blocks form Historic Old town, Walking Mall and restaurant Alley. 5 minutes drive to Shenandoah University. Winchester has been named fastest growing place in all of VA. Best place to retire by FORBS magazine. 15 hour outside of Washington DC excellent location for rental. City approved plans to

  Carlos Beamon Samson Properties

  16 W Clifford St, Winchester, VA 22601
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  /104

  $1,074,900

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

  700 Miller Rd, Winchester, VA 22602

  Situated on a 2.5 acre lot in highly desirable area, this stunning Colonial home offers an open floor plan perfect for entertaining. Thoughtfully designed with a main-level ensuite and a second primary suite on the upper level; 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

  Lilly Triplett Colony Realty

  700 Miller Rd, Winchester, VA 22602
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  /34

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,313 Sq Ft

  320 Highland Ave, Winchester, VA 22601

  Welcome to this centrally located home in the heart of Winchester. With easy access to I-81, this home is in a great commuter's location. Just a quick walk or drive away are the charming shops and restaurants of Historic Old Town Winchester. The main level features hardwood floors, a living room with wood-burning brick fireplace and a formal dining room, featuring a charming a built in China

  Heloisa Amar Samson Properties

  320 Highland Ave, Winchester, VA 22601
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  /2

  $250,000

  • 8 Beds
  • 5 Baths
  • 12,127 Sq Ft

  910 Franklin St, Winchester, VA 22601

  PRICE RARE UNIQUE OPPORTUNITY KNOCKS!ALL inside units cleaned, and junk removed - Ready for new investor.Warehouse also cleaned of junk and any hazards however has been condemned by City of Winchester as warehouse roof has caved in.Do not miss this rare opportunity to own this rare, unique property in Winchester. Work with the city of Winchester and turn this into your

  Pakeeza Akhtar The KOR Group, Inc.

  910 Franklin St, Winchester, VA 22601
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  /55

  $400,000 Open Sat 10AM - 2PM

  • 5 Beds
  • 3.5 Baths
  • 3,333 Sq Ft

  1503 Valley Ave, Winchester, VA 22601

  Active again, Buyer's loan fell through. Charming Colonial located in the heart of Winchester. Only a few minutes walk to the Old Town Mall. This home features 5 bedrooms and 3 1/2 baths with 4 levels. There's a Primary Bedroom and Bathroom located on the main level with doors that open onto the back deck. The family room boasts hardwood floors and a wood burning fireplace. The kitchen is

  Julie Teets Long & Foster Real Estate, Inc.

  1503 Valley Ave, Winchester, VA 22601
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  /40

  $379,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  112 Fairway Dr, Winchester, VA 22602

  New roof just installed!This beautiful ranch-style home is located in a quiet cul-de-sac just minutes from downtown Winchester, Jim Barnett Park, and Shenandoah University. Ideal for commuters, with easy access to Route 7 and I-81.The home features 3 bedrooms and 1 bathroom, with a full, partially finished basement adding 600 sq ft of finished space. A convenient basement kitchenette

  Daniel Brereton RE/MAX Roots

  112 Fairway Dr, 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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  /56

  $1,998,000

  • Studio
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  In town location for this completely remodeled multi unit property. This property contains 4 homes and 2 apartments that have been completely refinished. The main home is currently lived in by the owner and is attached to a indoor swimming pool. The other 3 homes and 2 apartments are leased and are bringing over$10,500 monthly. If you choose rent the main house income would be much higher. .

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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  /3

  $375,000

  • Land
  • 2.53 Acres
  • $148,221 per Acre

  0 N Frederick Pike Unit VAFV2024246, Winchester, VA 22603

  2.5344 Acres, Zoned B-2 General Business Office, Retail, Auto Dealers, Restaurants, Gas Service Stations, Sports (small area in rear is zoned RP) Site was also approved under the old regulations for storm water and is currently grandfathered as long as the current bond is in place. This is a tremendous amount of savingsAccess from North Frederick Pike, Autumn View Lane and Driveway on

  Suzanne Conrad Adams-Nelson & Associates Inc

  0 N Frederick Pike Unit VAFV2024246, Winchester, VA 22603
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  /39

  $312,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  127 S Euclid Ave, Winchester, VA 22601

  PRICE REDUCED!!!! BEATIFULL HOME!!! Fully Renovated Gem in the Heart of Winchester! Welcome to 127 Euclid , where modern upgrades meet timeless charm! This beautifully remodeled 3-bedroom, 2-bathroom rambler offers the perfect blend of comfort and convenience in one of Winchester’s most desirable locations. Step inside to discover a brand-new kitchen featuring stylish finishes, quartz

  Carolina Mosquera Weichert, REALTORS

  127 S Euclid Ave, Winchester, VA 22601
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  /56

  $2,098,000

  • 4 Beds
  • 2.5 Baths
  • 7,190 Sq Ft

  908 Cedar Creek Grade, Winchester, VA 22601

  Opportunity meets elegance in this fully remodeled multi-unit gem, perfectly situated in a prime in-town location. This unique property features four beautifully refinished homes and two modern apartments, offering both luxury and income potential in one impressive package.The main residence—currently owner-occupied—is a standout, seamlessly connected to a private indoor swimming pool, creating a

  Meridee Powars Link Realty Services LLC

  908 Cedar Creek Grade, Winchester, VA 22601
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  /28

  $649,000

  • 7,650 Sq Ft

  230 W Boscawen St, Winchester, VA 22601

  Multifamily, Professional Office, Historical Residence, or a combination of any of these opportunities! Even potential bed and breakfast or events center! Located in Historical Old Town Winchester, Holly House offers three floors, totaling over 7650 +/- SF, PLUS a HUGE outdoor English courtyard, ideal for urban gardening, building expansion, additional parking or pool! Iconic Federal Style

  Gillian Greenfield Coldwell Banker Premier

  230 W Boscawen St, Winchester, VA 22601
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  /16

  $269,000

  • Land
  • 0.97 Acre
  • $277,320 per Acre

  823 Armistead St, Winchester, VA 22601

  An amazing opportunity to acquire a prime lot in the City of Winchester, Virginia, perfect for your dream home!Nestled in the established Meadows Branch neighborhood, one of Winchester’s most upscale developments of beautifully crafted homes, this spacious 0.97 acre lot backs to the protected Abrams Creek Wetlands Preserve and Winchester’s Green Circle Trail.This ready-to-build homesite

  Janet Flaherty Keller Williams Realty

  823 Armistead St, Winchester, VA 22601
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  /15

  $256,000

  • Land
  • 33 Acres
  • $7,755 per Acre

  33+ ACRES Quail Run Ln, Winchester, VA 22602

  This is 4 contiguous lots of 8+ acres each with a total of 33.01 acres. Seller is selling as a whole, of the 33+ acres. The land is situated at the very back of Lincoln Estates. Property covenants are not enforced. Very quiet and private. There is no HOA. Roads are gravel/dirt, with no road maintenance in effect. Camp, Hike, build your cabin, hunt the land. Full of tall hardwoods. ATV

  Edward Beightol Cedar Creek Real Estate

  33+ ACRES Quail Run Ln, Winchester, VA 22602
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  /57

  $499,000

  • Land
  • 60 Acres
  • $8,249 per Acre

  0 Ewell Dr, Back Creek, VA 22602

  Enjoy the privacy and possibilities that come with over 60 acres of land, perfect for creating your custom home and outdoor haven. This property is located in a prestigious subdivision known for its large estate properties, offering a peaceful, rural lifestyle with a community feel. A fully approved septic site document is available, ensuring that the property is ready for your new home. For

  Brandi Marcum Pearson Smith Realty, LLC

  0 Ewell Dr, Back Creek, VA 22602
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  /7

  $53,500

  • Land
  • 0.06 Acre
  • $891,667 per Acre

  118 W Leicester St, Winchester, VA 22601

  Unique opportunity to own a piece of land in Historic Downtown Winchester. Located between Braddock and Washington Streets South of the Old Town Walking Mall. The property is within steps to Washington Street and the Apple Blossom Festival Parade route. The lot is located within the Historic District of Winchester. One parcels is included in this listing. Two lots are available for

  Kim Hurst MarketPlace REALTY

  118 W Leicester St, Winchester, VA 22601
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  /8

  $66,500

  • Land
  • 0.06 Acre
  • $1,108,333 per Acre

  116 W Leicester St, Winchester, VA 22601

  Unique opportunity to own a piece of land in Historic Downtown Winchester. Located between Braddock and Washington Streets South of the Old Town Walking Mall. The property is within steps to Washington Street and the Apple Blossom Festival Parade route. The lot is located within the Historic District of Winchester. One parcels is included in this listing. This lot includes a water and sewer

  Kim Hurst MarketPlace REALTY

  116 W Leicester St, Winchester, VA 22601
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  /10

  $599,000

  • Land
  • 0.09 Acre
  • $6,655,556 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
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  /11

  $1,100,000

  • Land
  • 2.48 Acres
  • $443,548 per Acre

  2725 S Pleasant Valley Rd, Winchester, VA 22601

  Location, location, location. Here is your chance to own one of the few commercial/industrial lots located in the highly desirable Winchester City. This cleared, blank slate is ready for your next business endeavor. Currently zoned as CM-1 (Commercial/Industrial), the property offers roughly 465 ft of prime road frontage, perfect for displaying your establishment.Current use regulations

  Kaitlyn Behr RE/MAX Roots

  2725 S Pleasant Valley Rd, Winchester, VA 22601
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  /7

  $499,000

  • Land
  • 18 Acres
  • $27,753 per Acre

  Lot 13 Tavistock Dr, Winchester, VA 22602

  Beautiful 17.98 acre Lot, approved for 3 bedroom perk, Tavistock Estates, one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

  Gillian Greenfield Coldwell Banker Premier

  Lot 13 Tavistock Dr, Winchester, VA 22602
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  /12

  $369,900

  • Land
  • 11 Acres
  • $32,193 per Acre

  Lot 1 Tavistock Dr, Winchester, VA 22602

  Beautiful 11.49 acre Lot, approved for 3 bedroom perk, Tavistock Estates one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

  Gillian Greenfield Coldwell Banker Premier

  Lot 1 Tavistock Dr, Winchester, VA 22602
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  /4

  $1,500,000

  • 3 Beds
  • 2 Baths

  821,839,851, lot44 Fox Dr, Winchester, VA 22603

  2.45 ACRES (4 current lots) ZONED RP WITH POTENTIAL CONVERSION FOR MIXED USE OR TOWNHOMES ECT. FRONTAGE ON FOX DRIVE CLOSE TO THE WINCHESTER MEDICAL CENTER AND DIRECTLY ACROSS FROM SUNNYSIDE PLAZA WITH KFC AND SHEETZ TO THE RIGHT OF PROPERTY. THREE EXISTING (RENTED $1,000/MONTH ON MONTH TO MONTH) HOMES AND VACANT LOT. PLATS AND TAX ID'S IN DOCUMENTS. EXISTING TOWNHOMES BACK RIGHT BEHIND

  Jim Thomson Realty ONE Group Old Towne

  821,839,851, lot44 Fox Dr, Winchester, VA 22603
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  /8

  $299,000

  • Land
  • 0.60 Acre
  • $498,333 per Acre

  229 S Pleasant Valley Rd, Winchester, VA 22601

  FOR SALE+PAD SITE APPROVED* (!) Pad site approved for 2000 SF professional office building on Pleasant Valley Road, Winchester City. Very rare opportunity! Will have direct access from Pleasant Valley Road. Excellent visibility and traffic count! Ideal for professional medical office building. Asking $299K. Contact Agent for more details!

  Gillian Greenfield Coldwell Banker Premier

  229 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /3

  $470,335

  • Land
  • 1.37 Acres
  • $343,310 per Acre

  0 Senseny Rd Unit VAFV2009062, Winchester, VA 22602

  PRICE REDUCED!! Owners are looking for reasonable offers. Lot fronts on Senseny road but can be accessed from the shopping center parking lot. Also can be purchased jointly with Lot H. Lot is flat and ready for development. The house adjoining the lot may also be available for purchase.

  John Coontz Commercial Specialists

  0 Senseny Rd Unit VAFV2009062, Winchester, VA 22602
• 

  /2

  $500,000

  • Studio
  • 1,175 Sq Ft

  513 and 525 Monticello St, Winchester, VA 22601

  For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

  Brett Haynes Oakcrest Commercial LLC.

  513 and 525 Monticello St, Winchester, VA 22601
• 

  /2

  $89,900

  • Land
  • 5 Acres
  • $17,124 per Acre

  Lot 14 Autumn Hills Estate, Gore, VA 22637

  Lot # 14. Autumn Hills Estate, Gore, VA ( Frederick County, VA ). BIG CORNER lot. 5.25 Acres on the corner of Three Oaks Dr., and W. Four Seasons Ln. Near cul-de-sac of W. Four Seasons Ln. Please see Tax Bill in the Documents Tab.. Please see GIS Coordinates Data in the Documents Tab.///Gore is an unincorporated community in western Frederick County, Virginia, United States, located off

  Vinay Gulati Dream Realty, Inc.

  Lot 14 Autumn Hills Estate, Gore, VA 22637
• 

  /2

  $69,900

  • Land
  • 0.19 Acre
  • $367,895 per Acre

  Lot 84 Purcell Ln, Winchester, VA 22603

  Buildable lot just outside Winchester City limits with easy access to shopping, town and Rt 37. Public water and sewer hook ups available. No restrictions on size of home. Sheds on property conveys. Wonderful for small or popular tiny home! Close to hospital and shopping.

  Jim Thomson Realty ONE Group Old Towne

  Lot 84 Purcell Ln, Winchester, VA 22603

Showing Results 81 - 120, Page 3 of 5