Winchester, VA Homes for Sale

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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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  /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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  /30

  $314,900

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft

  140 Mccormick Cir Unit 302, Winchester, VA 22602

  Welcome home to this gorgeous, like-new condo! This stunning unit was constructed last year and offers the perfect blend of modern elegance and comfort. Enjoy top-tier finishes like quartz countertops, stainless steel appliances, and beautiful LVP flooring throughout.Relax and unwind in the meticulously manicured common grounds, take a stroll on the walking path, or enjoy the convenience of

  Karl Achstetter Keller Williams Realty

  140 Mccormick Cir Unit 302, Winchester, VA 22602
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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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  /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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  /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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  /46

  $344,000

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

  308 Fawn Dr, Winchester, VA 22602

  Charming 3-Bedroom Home in Desirable Wilde Acres CommunityWelcome to this beautifully maintained 3-bedroom, 2.5-bath home, nestled on a spacious and flat lot in the sought-after Wilde Acres neighborhood. Featuring a 2-bay garage and fresh paint throughout, this move-in-ready home offers comfort, functionality, and a touch of nature all in one.Inside, enjoy a generous kitchen perfect for

  Kathrin Donovan Keller Williams Realty

  308 Fawn Dr, Winchester, VA 22602
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  /5

  $62,000

  • 3 Beds
  • 2 Baths
  • 980 Sq Ft

  114 Gregory Place Unit A130, Winchester, VA 22603

  Welcome to Regency Lakes, a vibrant and active all age community! This adorable, well-maintained 3 bedroom, 2 bath home is Move in Ready!! It has an open floor plan for socializing with guess while creating your favorite meal. Inside you will find thoughtful updates from the kitchen cabinets, stove, dishwasher, HVAC, to the large water heater. This home offers a perfect blend of comfort,

  Kristina Kelly Regency Lakes

  114 Gregory Place Unit A130, Winchester, VA 22603
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  /27

  $344,990

  • 3 Beds
  • 2.5 Baths
  • 1,566 Sq Ft

  144 Falcon Trail, Winchester, VA 22602

  Charming Split Foyer Home in Shawneeland – 144 Falcon Trail, Winchester, VAWelcome to 144 Falcon Trail, a delightful 3-bedroom, 2.5-bathroom split foyer residence nestled in the serene Shawneeland community of Winchester, VA. Built in 2009, this 1,566 sq ft home offers a perfect blend of comfort and potential, making it an ideal choice for first-time buyers or savvy investors.Enjoy a traditional

  Susan Wathen EXP Realty, LLC

  144 Falcon Trail, 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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  /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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  /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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  /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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  /6

  $398,000

  • Land
  • 0.60 Acre
  • $663,333 per Acre

  0 Marathon Dr, Winchester, VA 22602

  Property Description/Offering: Two parcels .61 and .6 ac to be sold together only. Corner lot with paved streets surrounded by developed parcels just off Valley Pike (Rte 11 South) near DMV. Ground is level and cleared. Fiber-optic cable in ground. Highlights (5):Well-known and easy access off Valley Pike (South) near DMVCorner LotZoned B2 - Business GeneralGround is level and cleared -

  Bill Nordman Commercial Specialists

  0 Marathon Dr, Winchester, VA 22602
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  /81

  $689,900

  • 4 Beds
  • 3.5 Baths
  • 4,411 Sq Ft

  226 Taggart Dr, Winchester, VA 22602

  Welcome to 226 Taggart Drive – a sunlit Colonial in the heart of Winchester's sought-after Raven Pointe community.This spacious 4-bedroom, 3.5 bath home offers over 4,200 square feet of beautifully finished living space across three levels, thoughtfully designed for comfort, functionality, and quiet everyday living. Nestled on a peaceful street just minutes from historic downtown Winchester,

  Lilly Triplett Colony Realty

  226 Taggart Dr, Winchester, VA 22602
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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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  /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
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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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  /52

  $475,000

  • 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

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
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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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  /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

  • 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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  /62

  $749,000

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  400 Great Mountain Ln, Winchester, VA 22602

  Please watch the Video! Escape to your own private mountain retreat with this stunning custom-built log home, offering breathtaking views of the Shenandoah Valley from an elevation of 1600 feet and 99+ acres of pristine land (elevation 2300+). Explore trails illuminated by solarlights—perfect for hiking,riding, and outdoor adventures. For shooting enthusiasts, a private range awaits, while an

  Leah Clowser RE/MAX Roots

  400 Great Mountain Ln, Winchester, VA 22602
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  /77

  $794,500

  • 4 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  127 Triangle Ct, Winchester, VA 22602

  One-year-young 4BR/4.5BA home in sought-after Abrams Pointe with over $158K in upgrades. Gourmet kitchen with quartz, custom cabinets, herringbone backsplash, & high-end appliances. Soaring 2-story great room, private office, and luxury primary suite with spa bath. Finished walk-up basement with full bath & potential 5th BR. 3-car garage, composite deck, & vinyl privacy fence (install

  Shelley Hanrahan

  127 Triangle Ct, Winchester, VA 22602
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  /74

  $669,000

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

  355 Fishel Rd, Winchester, VA 22602

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

  Daniel Brereton RE/MAX Roots

  355 Fishel Rd, Winchester, VA 22602
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  /9

  $186,000

  • Land
  • 60 Acres
  • $3,104 per Acre

  0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602

  UNIQUE 60 ACRE WOODED TRACT within the Great North Mountain Wilderness Area enhanced by County maintained hard surfaced road access and available electricity. The Offering also includes a contiguous half acre building Lot (Shawneeland - Tax ID 49-A05-1-W-1) which is located adjacent to the main tracts access point at the intersection of Tomahawk and Jalapa. Potential forty plus mile views

  Wayne Wilson Thomas and Talbot Estate Properties, Inc.

  0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602
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  /40

  $415,000

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft

  128 Pioneers Rd, Winchester, VA 22602

  The previous contract was released through no fault of the seller. Great house in an excellent location just minutes from commuter routes and downtown Winchester. There are many recent improvements and upgrades to the kitchen and bathrooms. The bedrooms and living areas are nicely proportioned for comfortable living. Wonderful gas fireplace in the living room makes a beautiful focal point. This

  Erika De Azagra ERA Oakcrest Realty, Inc.

  128 Pioneers Rd, Winchester, VA 22602
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  /63

  $349,900

  • 3 Beds
  • 2.5 Baths
  • 1,362 Sq Ft

  525 Pheasant Dr, Winchester, VA 22602

  Absolutely beautiful home. When you walk into this lovely home, with its many upgraded fixtures, and freshly painted walls you will realize there is nothing you need to do but relax and enjoy your new home. Three bedrooms, 2 1/2 bathrooms and a gourmet kitchen with stainless steel appliances. Primary bedroom has two closets, one is a walk-in, and a private bathroom. French doors leading to a

  Jimmy Biedrzycki CENTURY 21 New Millennium

  525 Pheasant Dr, Winchester, VA 22602
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  /12

  $19,500

  • Land
  • 0.29 Acre
  • $67,241 per Acre

  155 Hawk Trail, Winchester, VA 22602

  Lot 155 on Hawk Trail , is located in the mountainous residential community of Shawneeland, just 12 miles from Winchester, VA. Enjoy the fresh mountain air, hiking, fishing and swimming in Lake Cherokee in this idyllic setting. Know, however, that you are close to Winchester Medical Center, the Museum of the Shenandoah Valley, and an abundance of restaurants and shopping opportunities. Build a

  Rebecca McTavish Long & Foster Real Estate, Inc.

  155 Hawk Trail, Winchester, VA 22602
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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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  /50

  $399,000

  • 4 Beds
  • 3 Baths
  • 1,617 Sq Ft

  126 Armstrong Place, Winchester, VA 22602

  All brick ranch home with 4 bedrooms close to town and a short walk to the golf course! Main level large living Room and dinning room, 2 bedrooms and 2 bathrooms, an eat in kitchen, has gleaming hardwood flooring. Lower Level large area for pool table 2 more bedrooms, 1 bathroom and a family room equipped with a brick fireplace and space for a pool table. There is a sliding glass door that leads

  John Scully Colony Realty

  126 Armstrong Place, Winchester, VA 22602
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  /50

  $439,900 Open Sat 11AM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 1,776 Sq Ft

  103 Fenwick Ct, Winchester, VA 22602

  5 bedroom, 3.5 bathroom detached home! It's located in a neighborhood on a quiet cul-de-sac and convenient to route 7 and Route 81 for commuters. Large private 6 car new paved driveway -so plenty of off-street parking! Whole length of house rear deck for entertaining! Featuring rare main level bedroom with attached full bathroom. Plus, primary bedroom/primary full bathroom and 3 more bedrooms

  Sara Helmke Samson Properties

  103 Fenwick Ct, Winchester, VA 22602
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  /28

  $1,485,000

  • 4 Beds
  • 4.5 Baths
  • 5,754 Sq Ft

  291 Lake Serene Dr, Winchester, VA 22603

  This unique property is nestled in a beautiful, peaceful natural setting, on a private lake with stunning panoramic views from the two decks. The property includes 1.3 acres of meticulously landscaped grounds, gardens and retaining walls, 291 Lake Serene Dr is perfectly perched overlooking the lake, where one can immerse yourself in the natural beauty of Lake Serene. The magnificent

  Cynthia Butler Samson Properties

  291 Lake Serene Dr, Winchester, VA 22603

Showing Results 161 - 200, Page 5 of 10