Winchester, VA Homes

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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
• 

  

  

  /13

  $2,500 per month

  • 3 Beds
  • 2.5 Baths
  • 1,634 Sq Ft
  • Townhouse for Rent

  126 Maury Way, Winchester, VA 22602

  Almost new. Well mainted home located in the 55+ community of Winchester Landing. Main level primary suite with walk-in closet, hardwood floor, and tiled bathroom floor and shower. Kitchen complete with granite counters, stainless steel appliances, gas cooking, island, and tile backsplash. Hardwood and Tile flooring throughout the main level. Two additional bedrooms with hardwood flooring on the

  Rodolfo Balarezo LPT Realty, LLC

  126 Maury Way, Winchester, VA 22602
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  /24

  $327,000 Sold Aug 15, 2025

  • 1,217 Sq Ft
  • $269/SF
  • 48 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  827 Panther Dr, Winchester, VA 22602

  Back on market, buyer's financing fell through. Brand new and ready for you!! Quality built new construction by Beiler & Co, this home offers a wonderful, functional layout with lovely, upgraded finishes throughout. As you step inside, you're greeted by the open concept family/dining/kitchen area. The kitchen really shines with stainless steel appliances, quartz countertops, and a modern, open

  Bradley Comstock ERA Oakcrest Realty, Inc.

  827 Panther Dr, Winchester, VA 22602
• 

  

  

  /19

  Est $327,156 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2947 S Pleasant Valley Rd, Winchester, VA 22601

  2947 S Pleasant Valley Rd, Winchester, VA 22601
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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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  /27

  $2,100 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 203, Winchester, VA 22601

  This one bedroom and one bath apartment overlooks the roof onto Vibrissa's beautiful courtyard and mural. You will have a front row seat to live music and super quick access to tons of Apple Blossom events! Easy to clean and maintain LVP flooring has been installed throughout. The kitchen features a beautiful island, tons of cabinet space, with plenty of drawers for easy organizing, and stainless

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 203, Winchester, VA 22601
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  /35

  $299,900 Sold Aug 15, 2025

  • 2,304 Sq Ft
  • $130/SF
  • 69 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1931

  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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  /13

  Est $361,918 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  2912 Grace St, Winchester, VA 22601

  2912 Grace St, Winchester, VA 22601
• 

  

  /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
• 

  

  /13

  $1,700 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  5 Brookland Ct, Winchester, VA 22602

  Well maintained 2 bedroom 2 bath unit on 2nd floor. Gas fireplace and private balcony. Ready for move in. Landlord requires Minimum credit score of 700 and income of 3X the rent. Pets are welcome case by case. No prior evictions. Apply online using RentSpree link. All adults over 18 must apply $35 application fee per applicant.

  Hushai Mesfin Samson Properties

  5 Brookland Ct, Winchester, VA 22602
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  /24

  $514,990 Sold Aug 15, 2025

  • 2,050 Sq Ft
  • $251/SF
  • 15 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2025

  128 Webster Ct, Winchester, VA 22603

  Now under construction and will be Ready for Summer move in!! Welcome home to your new single level Hemingway located within Hiatt Pointe, the active adult section of Snowden Bridge for those 55 or better!!This brand new villa in a haven of refined main-level living designed for both comfort and effortless entertaining. Situated on a highly desirable premium lot, this villa offers an

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  128 Webster Ct, Winchester, VA 22603
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  /25

  Est $328,668 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  2817 Papermill Rd, Winchester, VA 22601

  2817 Papermill Rd, Winchester, VA 22601
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  /59

  $539,000

  • 2 Beds
  • 2 Baths
  • 1,674 Sq Ft

  411 N Loudoun St Unit 203, Winchester, VA 22601

  City Living with History & Style in the Heart of Old Town Winchester. Welcome to The Fort—a one-of-a-kind residence on the historic site of Fort Loudoun, once George Washington’s headquarters during the French and Indian War. While the fort itself is long gone, this landmark property carries a rich story, having served as a tavern, a girls’ seminary, and apartments before its exquisite

  Stephanie Feltner Realty ONE Group Old Towne

  411 N Loudoun St Unit 203, Winchester, VA 22601
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  /2

  $1,450 per month

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • House for Rent

  116 Greenwood Ave, Winchester, VA 22602

  3 bedroom, 1 bath ranch house on crawl space, hardwood/vinyl composite floors, stove and refrigerator on large lot, storage building in rear electric baseboard heat, application fee $30.00 cash or money order in one person's name, credit score of 650+, no suits, judgments, collections, income requirement 2.5-3x rent

  James Golladay Crum Realty, Inc.

  116 Greenwood Ave, Winchester, VA 22602
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  /37

  $349,990 Sold Aug 15, 2025

  • 1,509 Sq Ft
  • $232/SF
  • 62 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  117 Nootka Way, Winchester, VA 22602

  This rear-load, two-level townhome offers 1,509 square feet of well-designed living space, perfect for modern comfort and convenience. With three spacious bedrooms and 2.5 baths, it’s ideal for those seeking a low-maintenance lifestyle. The open layout includes a welcoming main level with plenty of room for entertaining, while the second floor hosts the bedrooms for added privacy. The home also

  Brooks Sears D R Horton Realty of Virginia LLC

  117 Nootka Way, Winchester, VA 22602
• 

  

  /19

  Est $328,470 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2918 S Pleasant Valley Rd, Winchester, VA 22601

  2918 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /17

  $435,000

  • 5 Beds
  • 4 Baths
  • 2,014 Sq Ft

  122 Cherry Hill Cir, Winchester, VA 22602

  Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

  Jen Moore ERA Oakcrest Realty, Inc.

  122 Cherry Hill Cir, Winchester, VA 22602
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  /2

  $1,200 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  208 W Boscawen St Unit 1, Winchester, VA 22601

  Enjoy the charm & convenience of downtown living in this one-bedroom, 1-bath first-floor apartment located steps from Winchester's historic shops, restaurants & entertainment. This comfortable apartment features an efficient layout with easy access to coin-operated laundry facilities on the main floor. A shared rear deck area provides a great spot to relax. Cats are considered on a

  Marisa Varley ERA Oakcrest Realty, Inc.

  208 W Boscawen St Unit 1, Winchester, VA 22601
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  /22

  $250,000 Sold Aug 14, 2025

  • 1,000 Sq Ft
  • $250/SF
  • 33 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1989

  213 Little River Dr, Winchester, VA 22602

  Welcome to this freshly painted 2-bedroom end-unit townhouse. This home offers an unbeatable location—just minutes from Route 7 and I-81Enjoy added privacy and space with an extra-large lot and a low-maintenance, mulched backyard surrounded by a privacy fence—ideal for relaxing or entertaining. As an end unit, you'll love the extra natural light. Recent upgrades include new dishwasher,

  Meghan Pachas Realty ONE Group Old Towne

  213 Little River Dr, Winchester, VA 22602
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  /21

  Est $353,707 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  2915 S Pleasant Valley Rd, Winchester, VA 22601

  2915 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /92

  $1,175,000

  • 4 Beds
  • 3.5 Baths
  • 4,815 Sq Ft

  2321 Cedar Grove Rd, Winchester, VA 22603

  Escape to your own private retreat! This custom log home on 21 wooded acres offers space, comfort, and endless outdoor enjoyment—without the restrictions of an HOA. Featuring over 3,200 sq. ft. on the main level plus 1,600+ finished sq. ft. in the walkout basement, this home provides room for everyone.Inside, you’ll find 4 bedrooms, 3 1/2 baths, and 2 fireplaces, along with an outdoor

  Traci Shoberg RE/MAX Roots

  2321 Cedar Grove Rd, Winchester, VA 22603
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  /2

  $1,299 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  3105 Shawnee Dr Unit 7, Winchester, VA 22601

  Recently Renovated 1 Bedroom, 1 Bath Loft Apartment on 3rd Floor of Building. Amazing location located within less than 1 mile from the great shopping on Valley Avenue. Nine minutes drive from Shenandoah University and 10 minutes from downtown Winchester. The property is under new ownership, and many major improvements are planned. Be part of this great transformation. This quiet neighborhood is

  Steve DuBrueler Coldwell Banker Premier

  3105 Shawnee Dr Unit 7, Winchester, VA 22601
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  /9

  $17,500 Sold Aug 14, 2025

  • Land
  • 0.46 Acre
  • $38,043 per Acre

  • 174 Days On Market

  0 Bobcat Trail Unit VAFV2023894, Winchester, VA 22602

  Whether you're looking for a peaceful vacation hideaway or a permanent residence, this is the perfect retreat. Nestled amidst nature, you'll have breathtaking views, endless tranquility, and a chance to truly "get away from it all."Enjoy The Lake, complete with a sandy beach, ideal for sunbathing, swimming, or simply relaxing by the water. Love fishing? Cast your line and unwind by

  Mary Cox Berkshire Hathaway HomeServices PenFed Realty

  0 Bobcat Trail Unit VAFV2023894, Winchester, VA 22602
• 

  

  /19

  Est $298,064 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,033 Sq Ft

  2908 Papermill Rd, Winchester, VA 22601

  2908 Papermill Rd, Winchester, VA 22601
• 

  

  /56

  $339,999 Open Sat 1PM - 3PM

  • 2 Beds
  • 1.5 Baths
  • 935 Sq Ft

  129 E Cork St, Winchester, VA 22601

  Welcome home to this charming 2-bedroom Craftsman-style home! Inside, you’ll find a warm and comfortable interior filled with character, including beautiful refinished hardwood floors, built-ins in the living room, and a built-in china cabinet in the dining room. The newly remodeled kitchen features newer appliances, while the furnace and AC are approximately 2.5 years old.Upstairs offers

  Melissa Crider Sager Real Estate

  129 E Cork St, Winchester, VA 22601
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  /2

  $1,549 per month

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Townhouse for Rent

  3107 Shawnee Dr Unit 10, Winchester, VA 22601

  Two level townhome*Full size Washer & Dryer*Hardwood like Floors* Huge Eat-In Kitchen*Granite counters & Stainless Steel Appliances*Spacious bedrooms*Large closets*Individually controlled HVAC and hot water heater*Plenty of parking*1 mile from great shopping on Valley Avenue, 10 minute from downtown Winchester and 9 minute from Shenandoah University.There is an additional $25 per person fee

  Steve DuBrueler Coldwell Banker Premier

  3107 Shawnee Dr Unit 10, Winchester, VA 22601
• 

  

  /51

  $739,000 Sold Aug 13, 2025

  • 4,625 Sq Ft
  • $160/SF
  • 5 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2008

  921 Kennedy Dr, Winchester, VA 22601

  Nestled on a quiet cul-de-sac within city limits, this exquisite 5-bedroom, 4.5-bath colonial offers over 4,625 square feet of finished living space and a rare backdrop of preserved battlefield views. Step into the grand two-story foyer flanked by formal living and dining rooms, then flow into the expansive family room featuring coffered ceilings and a dramatic floor-to-ceiling stone

  Julie Shiley Coldwell Banker Realty

  921 Kennedy Dr, Winchester, VA 22601
• 

  

  /23

  Est $274,615 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,252 Sq Ft

  2905 Sorrell Ct, Winchester, VA 22601

  2905 Sorrell Ct, Winchester, VA 22601
• 

  

  /22

  $270,000

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2949 Sorrell Ct, Winchester, VA 22601

  Charming Townhouse in Winchester City LimitsWelcome to this well-maintained townhouse offering three spacious bedrooms and one and a half baths, perfectly located within the desirable Winchester city limits. This interior unit boasts a spacious living room, ideal for both relaxation and entertaining.The primary bedroom is particularly noteworthy, featuring generous space and a

  Shanon Levi RE/MAX Roots

  2949 Sorrell Ct, Winchester, VA 22601
• 

  /2

  $2,750 per month

  • 4 Beds
  • 2.5 Baths
  • 1,953 Sq Ft
  • House for Rent

  108 Manasquan Way, Winchester, VA 22602

  Brand new home available in amenity rich new DR Horton community on Route 7 on Winchester East Side for September move-in for rental. The Pine is a 1,953 square foot open concept home, offering four bedrooms, two and a half bathrooms and a two-car garage. A foyer with a powder room and coat closet greets you as you enter this home. The open floorplan allows you and your loved ones to spend

  Vija Rallabandi Partners Real Estate

  108 Manasquan Way, Winchester, VA 22602
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  /8

  $9,700 Sold Aug 13, 2025

  • Land
  • 0.52 Acre
  • $18,654 per Acre

  • 14 Days On Market

  151 Tomahawk Trail, Winchester, VA 22602

  Potential Building Lot 151 Tomahawk Trail .52 acres. Breath taking Mountain Views coming & going. Quiet rural area still close to Hospital, Schools & Shopping. Enjoy the amenities, Fishing Lake & Ponds & streams. Recreational Park / Picnic area, golf pads, Playground, Beach Area & Road Maintenance

  Gina Griffith MarketPlace REALTY

  151 Tomahawk Trail, Winchester, VA 22602
• 

  

  /38

  Est $276,419 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2945 Sorrell Ct, Winchester, VA 22601

  2945 Sorrell Ct, Winchester, VA 22601
• 

  

  /65

  $825,000

  • 4 Beds
  • 3.5 Baths
  • 5,040 Sq Ft

  2411 Hunting Ridge Rd, Winchester, VA 22603

  This is the one you've been waiting for! Welcome to 2411 Hunting Ridge Rd. This large and private classic colonial is ready for you. With over 5000 sq ft and more than 5 acres of property, this beautiful home has it all. The winding tree-lined (and paved!) driveway invites you in. Enter into the welcoming two story foyer, which is flanked by lovely formal dining and sitting rooms. Exploring

  Amanda White Nova Home Hunters Realty

  2411 Hunting Ridge Rd, Winchester, VA 22603
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  /2

  $2,495 per month

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft
  • House for Rent

  528 Greenwood Rd, Winchester, VA 22602

  Ranch home featuring 3 Bedrooms, 2 Baths, 2 Sunrooms, partially finished basement, attached one car garage, and 2 car detached garage on Large Lot in Winchester.No Cats, Dogs on Case by case basis with $300 non-refundable pet deposit per approved pet.No Smoking

  Steve DuBrueler Coldwell Banker Premier

  528 Greenwood Rd, Winchester, VA 22602
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  /57

  $550,000 Sold Aug 13, 2025

  • 2,125 Sq Ft
  • $259/SF
  • 71 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1921

  220 Wolfe St, Winchester, VA 22601

  MOTIVATED SELLER! BRING ALL OFFERS! This House appraised at over $600,000Classic craftsman style bungalow featuring a covered front porch supported by Tuscan columns located in the historic district. Super location between Washington and Stewart streets, convenient to everything in Old Town and within feet of the parade route! Other features include tons of storage in three floors of

  Kathrin Donovan Keller Williams Realty

  220 Wolfe St, Winchester, VA 22601
• 

  

  /18

  Est $286,272 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2947 Sorrell Ct, Winchester, VA 22601

  2947 Sorrell Ct, Winchester, VA 22601
• 

  

  /65

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 3,283 Sq Ft

  231 Gun Barrel Ln, Winchester, VA 22603

  Spectacular, move-in ready rancher on over 6 acres. Completely remodeled within the past 3 years with all appliances, HVAC systems, roof, flooring and more less than 3 years old. The home offers a beautiful new kitchen with upgraded cabinets and quartz countertops. All bathrooms have also been completely updated with top-of-the-line vanities, tile and flooring. The lower level is finished into

  Dennis Virts RE/MAX Distinctive Real Estate, Inc.

  231 Gun Barrel Ln, Winchester, VA 22603
• 

  

  /11

  $1,700 per month

  • 2 Beds
  • 1.5 Baths
  • 1,254 Sq Ft
  • Townhouse for Rent

  116 Whirlwind Dr, Winchester, VA 22602

  Mandie Gladwell OliveTree Property Group, LLC

  116 Whirlwind Dr, Winchester, VA 22602
• 

  

  /26

  $295,000 Sold Aug 13, 2025

  • 2,052 Sq Ft
  • $144/SF
  • 204 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1981

  806 Appleseed Ct, Winchester, VA 22601

  Newly painted interior. This 3 bedroom, 1.5 bath townhouse with a large rec room in the lower level is located just where you want to be. Great community and so convenient to shopping and everyday life necessities.

  Joan Donald MarketPlace REALTY

  806 Appleseed Ct, Winchester, VA 22601
• 

  

  /30

  Est $293,622 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,332 Sq Ft

  2955 Sorrell Ct, Winchester, VA 22601

  2955 Sorrell Ct, Winchester, VA 22601

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