Winchester, VA Homes for Sale under $300,000

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  $279,900

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft

  2718 Welltown Rd, Winchester, VA 22603

  Beautiful and buildable lots on Welltown Road. Build your dream house and an extended family suite/ guest house. Build two, live in one, sell one! There are so many option on this unrestricted parcel. The mobile home on the property has electric, well and septic. The mobile home is not where the value is and is a tear down. The second parcel has been perc previously and is suitable for

  

  Tracey Scott

  Path Realty

  (540) 453-8745

  2718 Welltown Rd, Winchester, VA 22603
• Explore Winchester

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  /9

  $225,000

  • Land
  • 5.75 Acres
  • $39,130 per Acre

  Lot 3 Cedar Creek Grade, Winchester, VA

  Beautiful lot in a small neighborhood on the very desirable west side of Winchester off Cedar Creek Grade! Lot is already perked for 4 BR septic system. This opportunity doesn’t come along often! Rolling hills with beautiful surroundings and views. The location is less than 10 minutes to grocery stores, downtown Winchester, or Winchester Medical Center. It’s also located within 2 miles of

  

  Lori Bales

  Keller Williams Realty

  (540) 974-1542

  Lot 3 Cedar Creek Grade, Winchester, VA
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  /2

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft

  112 Star Fort Dr, Winchester, VA 22601

  Unlock the Potential! 3BR/2BA Fixer-Upper in Winchester/Frederick County. Nestled in a quiet Cul De Sac in Frederick County, this 3-bedroom, 2-bath home is bursting with potential and ready for a visionary buyer to bring it back to life. Whether you're looking to renovate and resell or transform this into a charming personal residence, the canvas is yours to create something

  

  Kimberly Schroeder

  Long & Foster Real Estate, Inc.

  (540) 502-3981

  112 Star Fort Dr, Winchester, VA 22601
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  /2

  $279,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  423 Highland Ave, Winchester, VA 22601

  Charming Winchester Home –Don't let this property slip away!This freshly updated home in the heart of Winchester offers incredible potential and versatility. Featuring off-street parking from the rear alley, a fresh coat of paint, and newly installed vinyl flooring downstairs, this property is move-in ready while leaving room for your personal touches.Highlights include:3

  

  Carlos Soares

  Samson Properties

  (540) 584-8746

  423 Highland Ave, Winchester, VA 22601
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  $285,000

  • 3 Beds
  • 2.5 Baths

  611 Tudor Dr, Winchester, VA 22603

  This charming and well-maintained townhome is a perfect for first time homebuyer or an investor! Priced to sell, and the location is pristine. It’s tucked back at the end of cul-de-sac, private and quiet and minutes from shopping, Winchester Medical Center, the beautiful downtown Winchester Walking Mall, and major commuter routes. The first thing you will love about this home is the welcoming

  

  Jodi Cilley

  Realty ONE Group Old Towne

  (540) 305-3448

  611 Tudor Dr, Winchester, VA 22603
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  /27

  $289,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  210 Zeiger Dr, Winchester, VA 22602

  Looking for a home just outside the city limits? You are 3 miles from Rt 37 and the hospital. This charming 3-bedroom, 1-bath rancher sits on 1.1 acres at the end of a cul-de-sac, surrounded by trees for extra privacy. Enjoy quiet mornings on the covered front porch or unwind in the evenings on the spacious wrap-around deck. Inside, the home has been tastefully remodeled and is move-in ready.

  Melissa Crider Sager Real Estate

  210 Zeiger Dr, Winchester, VA 22602
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  /29

  $299,900

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East

  Jodi Costello ERA Oakcrest Realty, Inc.

  1125 Conway St, Winchester, VA 22601
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  /20

  $299,999

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  608 Green St, Winchester, VA 22601

  Welcome to 608 Green Street. Come make this your own space. 3-Bedroom, 1 renovated full bath. Hardwood floors, no carpet! Attached carport. Brand new shed in the backyard. Backs to common area. Deck off the back of the home. Newer windows. New Roof. Large kitchen. Laundry room off the kitchen. This home is within the city limits of Winchester City School System. Within walking distance to

  Linda DeFelice Samson Properties

  608 Green St, Winchester, VA 22601
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  /19

  $299,500

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  106 W Southwerk St, Winchester, VA 22601

  Charming 3 bedroom, 1.5 bath colonial just blocks from downtown Winchester! Enjoy a covered front porch perfect for relaxing and a spacious rear deck for entertaining. Inside, you’ll find inviting spaces with newer windows throughout. Conveniently located near shopping, restaurants, entertainment, the local library, and Jim Barnett Park—this home offers both comfort and an unbeatable location!

  Sheila Pack RE/MAX Roots

  106 W Southwerk St, Winchester, VA 22601
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  /25

  $285,900

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft

  230 Shenandoah Trail, Winchester, VA 22602

  ONE LEVEL LIVING in a quiet and peaceful setting ! Enjoy the custom open floor plan joining the large country kitchen (with direct access to a full bath, laundry and entertaining deck) to the inviting living room featuring a brick fireplace with wood burning stove and bay window. In addition, there is a light filled family room with exterior access, two bedrooms and a second full bath located in

  Wayne Wilson Thomas and Talbot Estate Properties, Inc.

  230 Shenandoah Trail, Winchester, VA 22602
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  /26

  $287,500

  • 2 Beds
  • 2 Baths
  • 897 Sq Ft

  939 Woodland Ave, Winchester, VA 22601

  Price Reduced!!! Need your Own Space? or you're looking to Downsize or Just Starting Out, Come Checkout this 1–2-bedroom 2 full bath home on 3 Levels Updated Kitchen with Stainless Steel Appliances, a Living room Dining room or Main level Bedroom with a Full bath attached., Washer & Dryer in the shed convey. 2nd Level has a Bedroom Full bathroom and a loft area. Theres a unfinished Basement.

  Richard Kozlowski Long & Foster Real Estate, Inc.

  939 Woodland Ave, Winchester, VA 22601
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  /49

  $299,000

  • 2 Beds
  • 2 Baths
  • 2,795 Sq Ft

  159 Ashton Dr, Winchester, VA 22603

  Great Location! 2-Bedroom, 2-Bath Ranch with Great Potential! Sold "AS IS"Discover the possibilities in this spacious ranch-style home featuring 2 bedrooms and 2 full bathrooms. A large living room with a wood-burning fireplace. Kitchen and separate dining room. Hardwood flooring under carpet. The full basement offers a full bath, ample space for storage, a workshop, or future finished

  RoxAnn Grimes RE/MAX Roots

  159 Ashton Dr, Winchester, VA 22603
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  /16

  $299,900

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  20 E Hart St, Winchester, VA 22601

  This is a completely restored Winchester classic within walking distance to the downtown area and Handley High school. Located at the end of street. Home improvements include new HVAC, plumbing, electric and appliances. Interior pictures will follow as soon as painting has been completed.

  Meridee Powars Link Realty Services LLC

  20 E Hart St, Winchester, VA 22601
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  $285,000

  • 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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  /20

  $305,000

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  369 Charles St, Winchester, VA 22601

  This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two

  Marisa Varley ERA Oakcrest Realty, Inc.

  369 Charles St, Winchester, VA 22601
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  /18

  $245,000

  • 2 Beds
  • 1 Bath
  • 1,091 Sq Ft

  1033 Sunnyside Dr, Winchester, VA 22603

  Come check out this charming and cozy bungalow/cottage, located in Frederick County. Easy to show, located just outside the northern border of the City of Winchester. Offering 2 nice-sized bedrooms, spacious eat-in kitchen, fully equipped, with range, refrigerator, dishwasher and plenty of cabinets and counter space. Full bath has laundry area with washer and dryer. Inside, some TLC is needed,

  Gail Farrace Colony Realty

  1033 Sunnyside Dr, Winchester, VA 22603
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  /25

  $289,000

  • 3 Beds
  • 2.5 Baths
  • 1,296 Sq Ft

  505 Emily Ln, Winchester, VA 22602

  Charming Townhouse in the Beautiful Countryside of Winchester, VAMove-in ready! This spacious upper-level townhouse features:Three large bedroomsTwo full bathroomsGleaming hardwood floors throughoutFreshly painted interiorModern kitchen with stainless steel appliancesLarge backyard — perfect for relaxing or entertainingTwo reserved parking spacesEnjoy peaceful

  Trancito Laureano RE/MAX Gateway

  505 Emily Ln, Winchester, VA 22602
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  /31

  $235,000

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft

  205 Shenandoah Ave, Winchester, VA 22601

  LOCATION LOCATION LOCATION!!!!!!! INVESTORS DREAM. HOUSE NEEDS SOME WORK AND IS SOLD AS IS CONDITION.

  Ismael Carino MarketPlace REALTY

  205 Shenandoah Ave, Winchester, VA 22601
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  /7

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot C Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr RE/MAX Roots

  Lot C Cather Ln, Winchester, VA 22602
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  /6

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot B Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr RE/MAX Roots

  Lot B Cather Ln, Winchester, VA 22602
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  /7

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot A Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr RE/MAX Roots

  Lot A Cather Ln, Winchester, VA 22602
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  /19

  $285,000

  • 3 Beds
  • 1 Bath
  • 1,006 Sq Ft

  206 Custer Ave, Winchester, VA 22602

  Being Sold As Is but with great potential. Situate in a great location. This brick 3 bed, 1 full bath home on nearly an acre of land, with no HOA in a quiet neighborhood could be just what you are looking for. The addition in the rear will need to be reworked to satisfy the septic approval. Septic was recently inspected for County approval, results attached. Needs new septic tank, all else is

  Joan Donald MarketPlace REALTY

  206 Custer Ave, Winchester, VA 22602
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  /12

  $275,000

  • Land
  • 78.79 Acres
  • $3,490 per Acre

  LOT 13 Great Mountain Ln, Winchester, VA 22602

  Located In The Great North Mountain Wilderness Community! Don't Miss Out On This Amazing Opportunity To Own 78 Acres With Scenic Views! Whether You Are Looking For A Place To Build Your Dream Home Or A Get Away To Camp and Hunt With The Family, This Is The Perfect Location! As You Drive Up The Gravel Driveway There Is A Cleared Flat Area That Currently Has A Camper, Bunker, Out House, Solar

  Joseph Dedekind LPT Realty, LLC

  LOT 13 Great Mountain Ln, Winchester, VA 22602
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  $220,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  376 Charles St, Winchester, VA 22601

  Welcome home to laid-back charm in Winchester, VA! This inviting 3-bedroom, 1-bath home offers character, comfort, and plenty of breathing room to make your own. Inside, rich hardwood floors add warmth and continuity from the living room through the main level, while oversized windows flood the spacious bedrooms with natural light. The kitchen has plenty of cabinet space and a layout that

  Chris Craddock EXP Realty, LLC

  376 Charles St, Winchester, VA 22601
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  /28

  $265,000

  • 2 Beds
  • 1.5 Baths
  • 1,134 Sq Ft

  105 Chatham Square, Winchester, VA 22601

  Beautiful 2 level townhouse in established Huntington Meadows and eastside of Winchester allows you to get on the road to school, conveniences, work, or head north/south on I-81. Spacious bedrooms, large family room, gleaming hardwood floors, carpeted bedrooms, a massive back deck with fenced yard. All appliances convey which makes for minimum investment and move in ready!

  Dave Spence RE/MAX Roots

  105 Chatham Square, Winchester, VA 22601
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  /16

  $244,900

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  3253 Front Royal Pike, Winchester, VA 22602

  This home offers hardwood floors in the living room, dining room, and one bedroom. A cozy fireplace adds warmth and character, while two separate porches provide wonderful outdoor living space. The durable, low-maintenance brick and vinyl exterior and a partially finished basement offer practicality and storage. This property presents a fantastic opportunity to bring your vision and

  Derek Greene The Greene Realty Group

  3253 Front Royal Pike, Winchester, VA 22602
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  /10

  $225,000

  • Land
  • 20.05 Acres
  • $11,222 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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  /26

  $294,900

  • 3 Beds
  • 1 Bath
  • 1,094 Sq Ft

  143 Dowell J Cir, Winchester, VA 22602

  Charming Rancher with Prime Location and Endless Potential! Seller offering $5,000 towards buyers closing costs or desired upgrades.This well-built, single-level rancher offers 3 bedrooms and 1 full bath across 1,000 square feet of smartly designed living space. Nestled on a quiet street just outside Winchester city limits, this home falls within the Frederick County school

  Sarah Hott hott Realty ONE Group Old Towne

  143 Dowell J Cir, Winchester, VA 22602
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  /5

  $265,000

  • 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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  /32

  $244,900

  • 3 Beds
  • 2 Baths
  • 1,070 Sq Ft

  311 Ash Hollow Dr, Winchester, VA 22602

  Opportunity awaits in Ash Hollow Estates! This 3-bedroom, 2-bath townhouse is full of potential—solid bones, a smart layout, and endless possibilities for transformation. Whether you're an investor or a first-time buyer ready to create something special, this home is the perfect canvas. With a little TLC, a fresh new look is on the horizon! New carpet installed as of August 2025 adds a clean,

  Josh Medina ERA Oakcrest Realty, Inc.

  311 Ash Hollow Dr, Winchester, VA 22602
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  /26

  $232,750

  • Land
  • 23.44 Acres
  • $9,930 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

  $266,000

  • Land
  • 25.16 Acres
  • $10,572 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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  /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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  /3

  $299,000

  • Land
  • 2.53 Acres
  • $118,182 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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  /16

  $259,900

  • Land
  • 0.97 Acre
  • $267,938 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
  • 33.01 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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  /8

  $299,000

  • Land
  • 0.6 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
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  /2

  $289,900

  • 3 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  226 Muse Dr, Winchester, VA 22603

  Welcome to this almost completely renovated duplex home! Excellent location on the map, close to Downtown Winchester, shopping and Route 7 and I-81 for Commuting. This three bedroom and 1.5 bathroom home is getting a complete make over. New LVP Flooring throughout, Brand new kitchen cabinets and countertops, Kitchen Appliances, Bathroom vanities and tub/showers. Great opportunity for first time

  Brett Sowder RE/MAX Roots

  226 Muse Dr, Winchester, VA 22603
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  /2

  $235,000

  • Land
  • 0.92 Acre
  • $255,435 per Acre

  0 7 Building Lots In Shawneeland Unit VAFV2032844, Winchester, VA 22602

  CALLING ALL BUILDERS!! SEVEN BUILDING LOTS for $235,000 (being sold as a bundle) located in Shawneeland in Frederick County, VA. . Perc approved certification letter, plat and sewer docs on file for each lot. The lots range in size from 0.40-0.92 acres. Potential home sites for permanent home or weekends and vacations. Enjoy hiking, fishing, swimming in the lake, nature walks and playgrounds for

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

  0 7 Building Lots In Shawneeland Unit VAFV2032844, Winchester, VA 22602
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  /2

  $209,900

  • Land
  • 5.06 Acres
  • $41,482 per Acre

  3900 Hunting Ridge Rd, Winchester, VA 22603

  Discover the perfect blend of seclusion and convenience on this 5.06-acre lot, already equipped with electric access, a well, and septic—ready for your dream home or recreational getaway. Tucked away in a serene and private setting, this lot offers easy access to nearby amenities and is ideal for those seeking tranquility without sacrificing convenience. Whether you’re planning to build your

  Natalie Dalecky ERA Oakcrest Realty, Inc.

  3900 Hunting Ridge Rd, Winchester, VA 22603

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