Homes for Sale near John Handley High School

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  /5

  $289,500

  • 4 Beds
  • 1 Bath
  • 1,732 Sq Ft

  1006 S Cameron St, Winchester, VA 22601

  Don't miss out on this opportunity to own this 5 bedroom/1 bath home. Hardwood flooring throughout. Large, covered front porch and rear deck. Less than a mile from downtown Winchester & the Handley Library. Close to schools. Off-street parking and a spacious backyard. Access to alley from backyard and off-street parking.

  Sheila Pack RE/MAX Roots

  1006 S Cameron St, Winchester, VA 22601
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• 

  

  

  /45

  $399,900

  • 4 Beds
  • 1.5 Baths
  • 2,860 Sq Ft

  684 Berryville Ave, Winchester, VA 22601

  Come check out this 4-bedroom 1.5 bath 4 level Brick Colonial with a Detached Garage all on a double lot, updated roof, windows, new plumbing & water heater, updated electric & panel box. There is plenty of room to grow and put your flavor in the walk-up attic and basement. Home has the original Hardwood floors & Beautiful Woodworking that has never been painted on the main level. Large, Covered

  Richard Kozlowski Long & Foster Real Estate, Inc.

  684 Berryville Ave, Winchester, VA 22601
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  /58

  $1,129,000

  • 6 Beds
  • 5.5 Baths
  • 6,174 Sq Ft

  1020 Breckinridge Ln, Winchester, VA 22601

  A place to grow, gather, and stay awhile! From the moment you arrive, this property greets you with thoughtful details and a sense of home you can feel. A brick-paved, rocking chair-worthy front porch sets the tone, and the charming side porch with composite decking is both stylish and maintenance-free. This spacious 6+ bedroom/5.5 bath residence features a main-level bedroom and full bath—ideal

  Sheila Pack RE/MAX Roots

  1020 Breckinridge Ln, Winchester, VA 22601
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  /8

  $175,000

  • Land
  • 0.36 Acre
  • $486,111 per Acre

  2812 Saratoga Dr, Winchester, VA 22601

  A rare find and jewel of a lot! .36 acres in the perfect location on the south side of Winchester city limits. A short walk to Creekside Station with shopping and dining and the Kernstown Battlefield. Enjoy the quiet street with sidewalks and the bonus...water/sewer taps have been paid! Well maintained homes on either side make this a strong investment for a builder or create your custom

  Dave Spence RE/MAX Roots

  2812 Saratoga Dr, Winchester, VA 22601
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  /28

  $339,900

  • 3 Beds
  • 1 Bath
  • 1,376 Sq Ft

  230 Allison Ave, Winchester, VA 22601

  Welcome to 230 Allison Avenue, a recently renovated 3-bedroom, 1-bath home on a spacious 0.23-acre lot in Winchester. Ideally located just 1 mile from Winchester Medical Center and only minutes to Walmart Supercenter, shops, restaurants, and vibrant downtown Winchester, this home offers both convenience and charm. Step inside to discover a thoughtfully updated interior featuring luxury vinyl

  Jon Fleming Weichert Realtors - Blue Ribbon

  230 Allison Ave, Winchester, VA 22601
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  /81

  $1,224,000

  • 5 Beds
  • 5 Baths
  • 5,695 Sq Ft

  801 Armistead St, Winchester, VA 22601

  Step into refined elegance and exceptional quality in this beautifully upgraded residence, located in one of Winchester’s most desirable and walkable neighborhoods. This stately home offers the perfect blend of timeless architecture, sophisticated updates, and a lifestyle of convenience—just minutes from charming downtown shops, acclaimed restaurants, picturesque parks, and Winchester Medical

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  801 Armistead St, Winchester, VA 22601
• 

  

  /27

  $339,000

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  425 Beechcroft Rd, Winchester, VA 22601

  Looking for one level living in a sturdy, large (over 2000+/- SF) brick rancher close to all amenities? Restaurants and stores all within a couple of miles including Jim Barnett Park (swimming pools, yay). Easy access to major commuter routes. Relax on the huge front porch or rear covered patio in the private, fully fenced backyard. Semi-open floor plan in the main area bracket the kitchen

  Laurel Murray Samson Properties

  425 Beechcroft Rd, Winchester, VA 22601
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  /60

  $349,990

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

  1005 Pennsylvania Ave, Winchester, VA 22601

  This charming classic brick ranch in Winchester, VA, features 3 bedrooms and 2 full bathrooms, with easy access to downtown Winchester. As you approach, the covered front porch sets a welcoming tone. The basement has a separate entrance and additional space for bedrooms, a laundry area, and a full bathroom. Recent updates include an HVAC system, a washer and dryer, and complete renovations of

  Nathalie Acosta Spring Hill Real Estate, LLC.

  1005 Pennsylvania Ave, Winchester, VA 22601
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  /62

  $765,000

  • 4 Beds
  • 4.5 Baths
  • 5,183 Sq Ft

  1877 Clayton Ridge Dr, Winchester, VA 22601

  Nestled at the end of a quiet cul-de-sac and backing to serene wetlands and a protected preserve, this expansive colonial offers over 5,000 square feet of refined living space on nearly half an acre—providing both privacy and picturesque views. Boasting 4 generously sized bedrooms and 4.5 bathrooms, this home features a comfortable and functional main level layout perfect for everyday living and

  Dave Spence RE/MAX Roots

  1877 Clayton Ridge Dr, Winchester, VA 22601
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  /49

  $599,000

  • 5 Beds
  • 3 Baths
  • 3,200 Sq Ft

  1019 Berryville Ave, Winchester, VA 22601

  1019 Berryville Avenue, Winchester, VA 22601 is a Fully-rented triplex located just minutes from Old Town Winchester and Shenandoah University. This approximately 3,000 sq. ft. property is configured as three fully independent residential and commercial units. All units have private entrances, full kitchens, and separate electric. Middle unit may be used for commercial space. Units have been

  Pamela Debnam Houwzer, LLC

  1019 Berryville Ave, Winchester, VA 22601
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  /14

  $324,900

  • 3 Beds
  • 1.5 Baths
  • 1,704 Sq Ft

  10 Richards Ave, Winchester, VA 22601

  Back on the market with updated baths and brand-new flooring in the enclosed porch! Welcome to this charming classic home located in the City of Winchester. Built in 1940, this home offers timeless appeal and craftsmanship. Inside, you'll find 3 bedrooms, 1.5 baths, and a versatile fourth room—ideal for a home office, guest room, or creative space. The main level greets you with a welcoming

  Lindsey Richardson ERA Oakcrest Realty, Inc.

  10 Richards Ave, Winchester, VA 22601
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  /8

  $150,000

  • Land
  • 0.16 Acre
  • $937,500 per Acre

  1415 Ramseur Ln, Winchester, VA 22601

  This 0.16-acre lot is a rare opportunity to own a homesite in the desirable Early’s Green at Meadowbranch subdivision, located in the heart of Winchester. Nestled within a beautifully maintained community, this property offers access to fantastic amenities including common grounds, a swimming pool, and tennis courts—perfect for enjoying an active and social lifestyle. Conveniently located near

  Sheila Pack RE/MAX Roots

  1415 Ramseur Ln, Winchester, VA 22601
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  /37

  $389,000

  • 3 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  31 W Whitlock Ave, Winchester, VA 22601

  Charming Home Near Handley High School – Move-In Ready!Welcome to this beautifully updated home in a fantastic downtown location—just a short walk to shops, restaurants, and all that the vibrant city center has to offer. This property features a converted garage that now serves as a versatile studio space, perfect for a home office, art studio, or guest suite.Enjoy a spacious,

  Meridee Powars Link Realty Services LLC

  31 W Whitlock Ave, Winchester, VA 22601
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  /54

  $724,900

  • 4 Beds
  • 3 Baths
  • 3,482 Sq Ft

  1419 Ramseur Ln, Winchester, VA 22601

  (Not a 55 community)This beautifully maintained brick front rancher offers a spacious layout with 4 bedrooms and 3 full baths, situated in the desirable Early's Green at Meadowbranch community.Enjoy the comfort of single-level living with the added bonus of a finished basement with a professionally built bar—perfect for entertaining, hobbies, or extra living space. Hardwood flooring under

  Sheila Pack RE/MAX Roots

  1419 Ramseur Ln, Winchester, VA 22601
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  /87

  $699,900

  • 5 Beds
  • 6 Baths
  • 3,824 Sq Ft

  504 Old Fort Rd, Winchester, VA 22601

  Handsome Colonial loaded with possibilities, from a multigenerational home to spacious entertaining venues. It features a Main Floor ensuite Bedroom and expansive finished basement with kitchenette and outside entrance for possible in-law suite. Inviting lot with large pool and covered and open decks in large privacy fenced back yard. Conveniently located in lovely, well-maintained

  Dallas Croft Samson Properties

  504 Old Fort Rd, Winchester, VA 22601
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  /27

  $339,900

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft

  509 W Cork St, Winchester, VA 22601

  Location, Location, Location! Nestled in the heart of Winchester on the sought-after west side, this recently renovated 3-bedroom, 1-bath home offers modern comforts with a touch of classic charm. Step inside to discover a brand-new kitchen featuring gleaming white cabinets and exquisite granite countertops, perfect for culinary enthusiasts. The updated bathroom boasts a stylish tiled tub,

  Dan Whitacre Colony Realty

  509 W Cork St, Winchester, VA 22601
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  /34

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  12 Montague Cir, Winchester, VA 22601

  Welcome to 12 Montague Circle — a recently updated 3-bedroom, 1.5-bath home tucked away in a quiet cul-de-sac in downtown Winchester. Enjoy the best of both worlds with a peaceful, private setting and immediate access to restaurants, shops, grocery stores, and all the charm the city has to offer. This recently renovated gem features a new roof and HVAC system, durable and modern LVP flooring, and

  Jon Fleming Weichert Realtors - Blue Ribbon

  12 Montague Cir, Winchester, VA 22601
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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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  /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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  /43

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,299 Sq Ft

  341 Opequon Ave, Winchester, VA 22601

  Welcome home to this charming 3-bedroom, 1.5-bath gem perfectly located for easy access to I-81, Route 50, and Route 7—ideal for commuters. SEE VIDEO attached :)Enjoy the convenience of a main-level laundry room and peace of mind with a new roof installed in 2018. Step outside to your fully fenced backyard, complete with a screened-in porch and storage shed, perfect for relaxing or extra

  Sheila Pack RE/MAX Roots

  341 Opequon Ave, Winchester, VA 22601
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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

  $309,900

  • 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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  /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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  /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

  • 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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  /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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  /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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  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

Showing Results 41 - 80, Page 2 of 3