Winchester, VA Homes

• 

  

  

  /38

  $450,000 Sold Jul 07, 2025

  • 2,160 Sq Ft
  • $208/SF
  • 22 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1999

  119 Hill Valley Dr, Winchester, VA 22602

  Buyers Change of heart is your buyers good luck! Welcome to your dream home! This stunning split foyer residence, built in 1999, offers a perfect blend of comfort and style, boasting 2,160 sq. ft. of well-designed living space. With 4 spacious bedrooms and 3 full bathrooms, this home is ideal for those seeking both functionality and elegance. Step inside to discover a warm and inviting interior

  Stacy Mallonee Century 21 Redwood Realty

  119 Hill Valley Dr, Winchester, VA 22602
• 

  

  

  /25

  Est $321,082 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
• 

  

  

  /53

  $585,000

  • 3 Beds
  • 2.5 Baths
  • 2,527 Sq Ft

  125 Dewberry Dr, Winchester, VA 22602

  Discover the perfect blend of comfort and convenience in this 3 bedroom, 2 and a half bath single-story rambler nestled in the sought after neighborhood of Ravenwing. This home delivers spacious single level living with outdoor entertaining space and is move in ready. With sidewalks throughout the neighborhood, you can enjoy walking, running, or biking. This home is conveniently located close to

  Brittany Sims Keller Williams Capital Properties

  125 Dewberry Dr, Winchester, VA 22602
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  /60

  $485,000 Sold Jul 07, 2025

  • 1,914 Sq Ft
  • $253/SF
  • 11 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2014

  720 Adams Rd, Winchester, VA 22603

  Built in 2014, this nearly 2,000 sf modern rancher on 5 mostly wooded acres with no HOA is a hobbyist’s dream! In addition to two attached garages with custom 12’ wide doors, there’s also a 12'x10' attached shed, a 20'x20' workshop, and a detached shed/covered area for any equipment, materials, or supplies that need to be stored. Deer and other wildlife make their home on this property, where you

  Marcy Deck Dandridge Realty Group, LLC

  720 Adams Rd, Winchester, VA 22603
• 

  

  

  /19

  Est $328,237 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
• 

  

  /19

  $308,000

  • 2 Beds
  • 1 Bath
  • 1,027 Sq Ft

  104 Redwood Ln, Winchester, VA 22603

  Charming 2bedroom 1bath house located minutes from downtown Winchester in Frederick County. House features a large kitchen, mudroom, attic, basement and large fenced in back yard. This house has the potential to become a four bedroom as the current owner has started framing in the upstairs for two additional bedrooms along with electrical hookup. Water heater is 2 years old and HVAC system is

  Courtney Spaid Crum Realty, Inc.

  104 Redwood Ln, Winchester, VA 22603
• 

  

  /19

  $226,000 Sold Jul 03, 2025

  • 1,277 Sq Ft
  • $177/SF
  • 6 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1936

  521 1/2 N Loudoun St, Winchester, VA 22601

  Opportunity knocks in the heart of Winchester! This all-brick charmer sits just steps from downtown and is ready for its next chapter. With a classic front porch, a garage, and timeless architectural details, this home offers the perfect canvas for a full renovation. Whether you're an investor, contractor, or visionary buyer, this is your chance to bring a historic gem back to life in a prime

  Barton Chasler Realty ONE Group Old Towne

  521 1/2 N Loudoun St, Winchester, VA 22601
• 

  

  /21

  Est $352,269 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
• 

  

  /63

  $849,990

  • 4 Beds
  • 3.5 Baths
  • 3,942 Sq Ft

  756 Brookneil Dr, Winchester, VA 22602

  Some homes are lived in. Others are lived for. This one? It's the kind of place you wait for—the kind you watch for, and when it finally hits the market, you clear your calendar to see it.Set deep into over 9 private wooded acres, at the very end of a quiet cul-de-sac, this completely rebuilt ranch-style home in Winchester offers something you rarely find anymore: total privacy, modern

  Alexander Bracke Real Broker, LLC

  756 Brookneil Dr, Winchester, VA 22602
• 

  

  /39

  $365,000 Sold Jul 03, 2025

  • 1,833 Sq Ft
  • $199/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1964

  320 Russellcroft Rd, Winchester, VA 22601

  Lovingly maintained by the same owner for over 50 years, this charming ranch-style home is a true gem! From the moment you arrive, the care and attention to detail are clear — from the circular driveway and manicured lawn to the discreet bin enclosure that keeps trash cans out of sight. Enjoy the ease of main-level living with 3 spacious bedrooms and 2 full baths, including a private ensuite off

  Jeanne Mezzatesta Colony Realty

  320 Russellcroft Rd, Winchester, VA 22601
• 

  

  /19

  Est $299,295 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,033 Sq Ft

  2908 Papermill Rd, Winchester, VA 22601

  2908 Papermill Rd, Winchester, VA 22601
• 

  

  /49

  $669,000

  • 4 Beds
  • 2.5 Baths
  • 3,512 Sq Ft

  2321 Stoneridge Rd, Winchester, VA 22601

  Must see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The open foyer invites you into this spacious home boasting over 3500 sq.ft. plus a full walk-out basement, ready to finish for additional square footage. Large living and dining rooms with hardwood, den or office. Large kitchen features granite counters, stainless steel appliances, and a breakfast area that

  John Schroth Colony Realty

  2321 Stoneridge Rd, Winchester, VA 22601
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  /48

  $685,000 Sold Jul 03, 2025

  • 4,270 Sq Ft
  • $160/SF
  • 3 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1900

  503 S Washington St, Winchester, VA 22601

  Discover unparalleled charm and historic elegance in this circa 1900 Victorian residence, ideally situated in Winchester's downtown Historic District and on the Apple Blossom parade route. Stunning 5-bedroom,4.5 bathroom home, boasting approximately 4270 sq ft of living space, invites you to experience the grandeur of a bygone era. Off-street parking.Key features include:Historic Charm:

  John Schroth Colony Realty

  503 S Washington St, Winchester, VA 22601
• 

  

  /23

  Est $268,808 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
• 

  

  /36

  $419,900

  • 2 Beds
  • 2 Baths
  • 1,664 Sq Ft

  100 Candlewick Dr, Winchester, VA 22602

  “Cottage on Candlewick” - Welcome to easy, one-level living in the highly sought-after Cross Creek Village, a 55+ community designed for comfort, convenience, and connection. This beautifully maintained 2-bedroom, 2-bath home offers over 1,600 square feet of thoughtfully designed living space—all on one level for maximum accessibility.Perfectly situated near the front of the neighborhood

  Mark Francis ICON Real Estate, LLC

  100 Candlewick Dr, Winchester, VA 22602
• 

  

  /30

  $537,000 Sold Jul 03, 2025

  • 2,154 Sq Ft
  • $249/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  1412 Magruder Ct, Winchester, VA 22601

  This peaceful property is within minutes of the Old Town Walking Mall, the arts of Shenandoah University , Winchester Little Theater, Museum of the Shenandoah Valley, Winchester Medical Center and shopping.Spacious living room/dining room with gas fireplace joins a sunroom opening to deck surrounded by lush landscaping. The kitchen features an inviting light filled breakfast area

  Kathryn Hallett Long & Foster Real Estate, Inc.

  1412 Magruder Ct, Winchester, VA 22601
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  /38

  Est $267,083 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
• 

  

  /23

  $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!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 district and combines peaceful surroundings with unbeatable convenience—just one minute to

  Sarah Hott hott Realty ONE Group Old Towne

  143 Dowell J Cir, Winchester, VA 22602
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  /57

  $630,000 Sold Jul 03, 2025

  • 2,774 Sq Ft
  • $227/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1865

  716 S Washington St, Winchester, VA 22601

  Well-maintained and full of charm, this 2,774 sq ft, 4-bedroom, 3.5-bath home sits on a 1/3-acre lot in the heart of Old Town Winchester—just one block from Handley High School and a short distance to the vibrant Winchester Walking Mall. Built over 150 years ago, this home features original pine floors, a formal living and dining room, a grand marble-tiled foyer, and a dedicated office with

  Lisa Alberti Roberts Realty Group, LLC

  716 S Washington St, Winchester, VA 22601
• 

  

  /18

  Est $275,674 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
• 

  

  /51

  $1,195,000

  • 7 Beds
  • 4.5 Baths
  • 6,380 Sq Ft

  207 Westview Dr, Winchester, VA 22603

  Welcome to 207 Westview Drive, a secluded sanctuary nestled on just over six wooded acres in the heart of the Shenandoah Valley—mere minutes from the charm of Historic Old Town Winchester. With over 6,600 square feet of beautifully finished living space, this one-of-a-kind property offers the perfect blend of luxury, comfort, and natural beauty. Tucked deep into the trees, yet close to shops,

  Carolyn Young Samson Properties

  207 Westview Dr, Winchester, VA 22603
• 

  

  /28

  $479,990 Sold Jul 03, 2025

  • 1,953 Sq Ft
  • $246/SF
  • 87 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  119 Monacan St, Winchester, VA 22602

  The Pine Floor Plan offers 1,964 square feet of thoughtfully designed living space, making it a perfect choice for growing families or those who love to entertain. This single-family home features four spacious bedrooms, 2.5 bathrooms, and an open-concept layout. The sleek kitchen is equipped with gray cabinetry, granite countertops, and stainless steel appliances, blending style and

  Tracy Jennings D R Horton Realty of Virginia LLC

  119 Monacan St, Winchester, VA 22602
• 

  

  /12

  Est $274,513 Not Listed For Sale

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

  2949 Sorrell Ct, Winchester, VA 22601

  2949 Sorrell Ct, Winchester, VA 22601
• 

  

  /26

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  1004 S Cameron St, Winchester, VA 22601

  PRICE REDUCED***Renovated Home in Winchester neighborhood.*** You’ll enter the house and find a spacious living room. As you continue walking, you’ll be led to the fully renovated kitchen. The kitchen features stainless steel appliances, including a new refrigerator, stove, microwave, dishwasher, new cabinets, and a granite countertop. The laundry room, located conveniently on the main level,

  Patricia Salgado Metas Realty Group, LLC

  1004 S Cameron St, Winchester, VA 22601
• 

  

  /26

  $375,000 Sold Jul 03, 2025

  • 1,342 Sq Ft
  • $279/SF
  • 112 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  2969 Wardensville Grade, Winchester, VA 22602

  1900’s farmhouse with beautiful views. Completely renovated with new electrical system and plumbing. New GE appliances with Woodstove in kitchen. 3 story storage shed on 5 acres of wooded land. 15 mins fromWinchester medical center.

  Debbie Crevier Kent Cottage Street Realty LLC

  2969 Wardensville Grade, Winchester, VA 22602
• 

  

  /30

  Est $284,758 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
• 

  

  /143

  $950,000

  • 5 Beds
  • 4.5 Baths
  • 4,438 Sq Ft

  769 Seldon Dr, Winchester, VA 22601

  Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living.The main level features a generously sized primary suite with a walk-in closet and en-suite bath,

  Amanda Slate Keller Williams Realty

  769 Seldon Dr, Winchester, VA 22601
• 

  

  /54

  $550,000 Sold Jul 02, 2025

  • 2,551 Sq Ft
  • $216/SF
  • 28 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1927

  529 N Braddock St, Winchester, VA 22601

  Priced below appraised value!Welcome home to this charming, light filled Dutch Colonial in the heart of downtown Winchester. With four livable levels, this three bedroom, 2 bath home has been lovingly updated and renovated over the years embracing the charm of a bygone era and offering modern conveniences. Updates include the addition of a dual zone heat pump system (2019) providing cooling

  Dana Cloud Realty ONE Group Old Towne

  529 N Braddock St, Winchester, VA 22601
• 

  

  /29

  Est $274,761 Not Listed For Sale

  • 2 Beds
  • 3.5 Baths
  • 1,280 Sq Ft

  2957 Sorrell Ct, Winchester, VA 22601

  2957 Sorrell Ct, Winchester, VA 22601
• 

  

  /107

  $799,900

  • 4 Beds
  • 3.5 Baths
  • 5,161 Sq Ft

  132 Wilton Dr, Winchester, VA 22603

  Beautifully Conceived Custom Colonial on 2.59 manicured acres with mature trees and landscaping. Versatile floor plan with Main Floor Primary and generous room sizes for elegant one level living, complemented by multiple bedrooms above and a fully finished basement--possible in-law suite with level walkout. Large composite deck features a screened gazebo and overlooks beautiful patio with stone

  Dallas Croft Samson Properties

  132 Wilton Dr, Winchester, VA 22603
• 

  

  /3

  $271,000 Sold Jul 01, 2025

  • 1,197 Sq Ft
  • $226/SF
  • 23 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1965

  421 Superior Ave, Winchester, VA 22601

  This home is part of an Estate and is being sold as is. Needs a little TLC. Great starter home.Perfectly situated just minutes from shopping, restaurants, and I-81, this property offers convenience without sacrificing its quaint charm. Don't miss out on this genuinely affordable opportunity. Give me a call today to make it yours!

  Cathy Caniford Crossroads, Realtors

  421 Superior Ave, Winchester, VA 22601
• 

  

  /10

  Est $277,046 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2963 Sorrell Ct, Winchester, VA 22601

  2963 Sorrell Ct, Winchester, VA 22601
• 

  

  /22

  $334,900

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

  140 Mccormick Cir Unit 403, Winchester, VA 22602

  Nearly-new 55+ condominium located in Winchester Landing, offering comfort, convenience, and style just minutes from town. Step inside to an open floor plan filled with natural light, featuring a bright and modern kitchen with quartz countertops, a center island with sink, and sleek lighting that makes entertaining a breeze.The oversized primary suite is a true retreat, complete with a

  Sharon Farinholt Realty ONE Group Old Towne

  140 Mccormick Cir Unit 403, Winchester, VA 22602
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  /26

  $255,000 Sold Jul 01, 2025

  • 1,080 Sq Ft
  • $236/SF
  • 4 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  237 Kimberly Way, Winchester, VA 22601

  This beautifully renovated 2-bedroom, 1.5-bath townhouse features a spacious deck and a fenced backyard—perfect for outdoor entertaining. Enjoy fresh landscaping and stylish updates throughout. Ideally located within walking distance to downtown Winchester and Jim Barnett Park, and just minutes from shopping, Shenandoah University, and Winchester Medical Center. A perfect blend of comfort and

  Leah Clowser RE/MAX Roots

  237 Kimberly Way, Winchester, VA 22601
• 

  

  /27

  Est $287,558 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2967 Sorrell Ct, Winchester, VA 22601

  2967 Sorrell Ct, Winchester, VA 22601
• 

  

  /21

  $425,000

  • 5 Beds
  • 2 Baths
  • 1,710 Sq Ft

  912 Opequon Ave, Winchester, VA 22601

  Welcome to 912 Opequon Ave- Spacious, Updated & Perfectly Located in Winchester !Opportunity meets versatility in this beautifully updated 5 bedrooms, 2 bath home nestled in one of Winchester most walkable and convenient neighborhoods! Whether you're a homeowner seeking flexible living space or an investor eyeing income potential, this property checks every box . Freshly painted interior

  max cortijo Fairfax Realty of Tysons

  912 Opequon Ave, Winchester, VA 22601
• 

  

  /31

  $260,000 Sold Jul 01, 2025

  • 1,054 Sq Ft
  • $247/SF
  • 20 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1951

  3544 Papermill Rd, Winchester, VA 22602

  A charming and cozy rancher with updated interior, located on south side of the City of Winchester and offering 3 bedrooms, one bath and 1,054 square feet of living space with numerous and thoughtful updates. Spacious kitchen fully equipped with plenty of cabinets, counter space and appliances. Luxury Vinyl Plank (LVP) flooring in living room, dining room and all bedrooms. Separate and

  Gail Farrace Colony Realty

  3544 Papermill Rd, Winchester, VA 22602
• 

  

  /16

  Est $279,825 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  2975 Sorrell Ct, Winchester, VA 22601

  2975 Sorrell Ct, Winchester, VA 22601
• 

  

  /25

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  Completely remodeled! Come enjoy ALL new everything, new electric, new windows, luxury floors, freshlypainted walls and brand-new custom kitchen and bathrooms, and all new plumbing and electricthroughout, nothing has been left untouched! New Mini Split HVAC system. Large living room opens into a gorgeous wrap aroundpeninsula kitchen with brand new Samsung appliances, granite

  Lawrence Lessin Homes By Owner, Inc.

  553 Highland Ave, Winchester, VA 22601
• 

  

  /61

  $599,900 Sold Jul 01, 2025

  • 3,578 Sq Ft
  • $168/SF
  • 3 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  232 Devland Dr, Winchester, VA 22603

  Spacious, wonderful home on a tranquil, wooded setting, just minutes from Winchester and I-81. This modular-built home came together in 2005, and boasts 4 bedrooms, including the master on the main level with en-suite luxury bath, and three full plus one half bath. Big and roomy kitchen with breakfast space on one end, and a little breakfast bar on the other end, is great place to chef.

  Richard Hampton Douglas Elliman of Metro DC, LLC - Arlington

  232 Devland Dr, Winchester, VA 22603

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