Winchester, VA Homes for Sale

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  /49

  $280,000

  • Land
  • 25 Acres
  • $11,129 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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  /50

  $345,000

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

  0 Easter Ridge Lot 8 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 with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters via a loft. Experience exciting

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Easter Ridge Lot 8 Ln, Winchester, VA 22603
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  /47

  $600,000

  • 4 Beds
  • 3 Baths
  • 2,203 Sq Ft

  167 Morning Glory Dr, Winchester, VA 22602

  Welcome to the beautiful Twin Lakes Community! This charming ranch-style residence offers the ease of one-level living with a spacious and thoughtfully designed floor plan. The main level features a welcoming front den—perfect for a home office or reading nook—an updated kitchen with a large pantry area, a dining room filled with natural light, and a cozy family room complete with a gas

  Lisa Behr Coldwell Banker Premier

  167 Morning Glory Dr, Winchester, VA 22602
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  /69

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,189 Sq Ft

  1793 N Hayfield Rd, Winchester, VA 22603

  Back on the market - the buyer's home did not sell.Charming all-brick ranch home on a spacious .97-acre lot, featuring 3 bedrooms, 2.5 baths, and traditional style throughout. Enjoy a covered front porch, rear deck, living room with fireplace, separate dining room, and eat-in kitchen. Includes a 2-car garage and no HOA. Ideally located—peaceful setting just outside of town, yet only 10

  RoxAnn Grimes RE/MAX Roots

  1793 N Hayfield Rd, Winchester, VA 22603
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  /47

  $450,000

  • 3 Beds
  • 1.5 Baths
  • 1,952 Sq Ft

  164 Bethel Grange Rd, Winchester, VA 22603

  Beautiful brick ranch in a lovely rural setting with mountain views and only minutes to town amenities. Sellers are installing new central air conditioning . 3 bedrooms, 1 1/2 baths with a shower stall in mud room downstairs. Country kitchen with adjoining carport. Large living room front window with nice view of Round Hill. Extra closets. 4 ft hallway with ceiling fan. 5x16 covered front

  Cathy Durbin Crum Realty, Inc.

  164 Bethel Grange Rd, Winchester, VA 22603
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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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  /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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  /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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  /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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  /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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  /35

  $319,900

  • 4 Beds
  • 2 Baths
  • 2,304 Sq Ft

  911 Martinsburg Pike, Winchester, VA 22601

  Charming 1931 Home with Timeless Appeal & New Metal Roof – 911 Martinsburg Pike, WinchesterStep into a piece of Winchester history with this stunning "four-square" home, offering a perfect blend of old-world charm and modern convenience. Boasting 4 spacious bedrooms (5 if you make the main level room into a bedroom) and 2 full baths, including a main-level en suite, this home is designed for

  Sarah Abderrazzaq Realty ONE Group Old Towne

  911 Martinsburg Pike, Winchester, VA 22601
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  /53

  $475,000

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

  669 Dicks Hollow Rd, Winchester, VA 22603

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

  Barbera Clausen EXP Realty, LLC

  669 Dicks Hollow Rd, Winchester, VA 22603
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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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  /12

  $54,900

  • Land
  • 0.73 Acre
  • $75,205 per Acre

  LOTS 7 & 8 Manor Dr, Winchester, VA 22602

  Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have some space between neighbors. Lots 7 & 8 are being sold

  Bradley Comstock ERA Oakcrest Realty, Inc.

  LOTS 7 & 8 Manor Dr, Winchester, VA 22602
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  /40

  $374,500

  • 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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  /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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  /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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  /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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  /72

  $699,000

  • 4 Beds
  • 4.5 Baths
  • 4,320 Sq Ft

  292 Green Spring Rd, Winchester, VA 22603

  Welcome to your dream home! Nestled on just over 5 serene acres, this beautifully maintained 4-bedroom, 4.5-bathroom property offers the perfect blend of comfort, style, and functionality. From the moment you arrive, you’ll be charmed by the picturesque country and mountain views and the orchard-like feel created by numerous fruit trees (peaches, pears, apples, and cherries) lining the front

  Katie Landi Jordan Samson Properties

  292 Green Spring Rd, Winchester, VA 22603
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  /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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  /42

  $180,000

  • 3 Beds
  • 1 Bath
  • 775 Sq Ft

  117 Miller Rd, Winchester, VA 22602

  Welcome to 117 Miller Rd—your chance to own a hidden gem in one of Frederick County’s most historic and picturesque settings. Nestled on a beautiful, flat, and cleared 1-acre lot, this property is just minutes from downtown Winchester and less than 4 miles down Cedar Creek Grade. Tucked beside the Opequon Historic District—home to some of the area’s earliest settlements—you’ll be surrounded by

  Kaitlyn Behr RE/MAX Roots

  117 Miller Rd, Winchester, VA 22602
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  /71

  $849,900

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  251 Heather Hill Ln, Winchester, VA 22603

  Back on market at NO fault of seller. Have you been looking for peace and serenity, then you've found it. This gorgeous property offers almost 50 acres (there are several different parcels included in this sale. Parcels that are included are: 19-3-7 (house parcel, 5 acres), 19-3-10 (garage, pole barn parcel, 5 acres), 19-3-12 (7.79 acres), 19-A-48 (31.04 acres). The lovely Chalet offers 3

  Amber Jenkins Century 21 Redwood Realty

  251 Heather Hill Ln, Winchester, VA 22603
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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
• 

  

  /60

  $660,000

  • 4 Beds
  • 2.5 Baths
  • 3,165 Sq Ft

  109 Aulee Ct, Winchester, VA 22602

  If you’re looking for a home that truly checks all the boxes, space, setting, style, and room to grow, this is the one you’ve been waiting for. Perfectly perched on a quiet cul-de-sac in the sought-after Twin Lakes Overlook neighborhood, this Toll Brothers built beauty offers more than curb appeal. It boasts a premium lot backing to the lake, with tranquil views that just might make you forget

  Kim Spear Keller Williams Realty

  109 Aulee Ct, Winchester, VA 22602
• 

  

  /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

Showing Results 121 - 160, Page 4 of 9