Winchester, VA Homes

• 

  

  

  /43

  $559,900 Sold Oct 10, 2025

  • 2,614 Sq Ft
  • $214/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1987

  1729 Handley Ave, Winchester, VA 22601

  This immaculate 4-bedroom, 3-bath Cape Cod in sought-after Meadow Branch is move-in ready and full of thoughtful updates! From the welcoming foyer, the home flows seamlessly into a bright living room, spacious kitchen, and dedicated dining room. On the main level you'll also find two bedrooms and a full bath, perfect for guests or convenient one-level living.From the kitchen, step outside

  Jeanne Mezzatesta Colony Realty

  1729 Handley Ave, Winchester, VA 22601
• 

  

  

  /24

  Est $474,198 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  609 Quartzite Cir, Winchester, VA 22601

  609 Quartzite Cir, Winchester, VA 22601
• 

  

  

  /37

  $259,900

  • 3 Beds
  • 2 Baths
  • 931 Sq Ft

  309 Raccoon Dr, Winchester, VA 22602

  Move in ready 3 bedroom 2 full baths home nestled in the woods that comes with additional lots(2) that can be built on or kept as a privacy buffer and equates to an acre or so. House features hardwood flooring and lots of knotty pine for that rustic look. Living room features a wood burning fireplace that is capable of heating the entire house and there is plenty of free down wood on the lot

  James Amick RE/MAX Roots

  309 Raccoon Dr, Winchester, VA 22602
• 

  

  

  /25

  $232,000 Sold Oct 10, 2025

  • 720 Sq Ft
  • $322/SF
  • 74 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1970

  132 Erie Trail, Winchester, VA 22602

  **Back on the market at no fault of the seller**This charming move-in ready home in the sought-after Shawneeland community offers the perfect blend of modern comfort and natural beauty. Featuring a newer roof, newer washer and dryer, updated lighting and fixtures, and a beautifully renovated bathroom and kitchen, this home has everything done for you. The primary bedroom currently holds a queen

  Ember Crow Pearson Smith Realty LLC

  132 Erie Trail, Winchester, VA 22602
• 

  

  

  /24

  Est $413,984 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,854 Sq Ft

  625 Quartzite Cir, Winchester, VA 22601

  625 Quartzite Cir, Winchester, VA 22601
• 

  

  /86

  $2,125,000

  • 5 Beds
  • 4 Baths
  • 4,166 Sq Ft

  1631 Back Mountain Rd, Winchester, VA 22602

  This unique property is the definition of an oasis in the woods. Surrounded by 180 glorious private acres, this home dazzles with grandeur while blending natural elements that mesh with the environment. The handsome hunter green standing seam metal roof with matching accents against wood siding is the ideal look for this 4,166 square foot architectural marvel. Indoors, there’s a thoughtful

  Dan Whitacre Colony Realty

  1631 Back Mountain Rd, Winchester, VA 22602
• 

  

  /42

  $324,500 Sold Oct 10, 2025

  • 1,178 Sq Ft
  • $275/SF
  • 141 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1930

  107 E Monmouth St, Winchester, VA 22601

  Price Reduction!! Charming Historic Home in Downtown Winchester – Move-In Ready!If you love timeless craftsmanship—think original wood floors, custom built-ins, and vintage doors—but still want the ease of modern living, this beautifully updated downtown Winchester home is calling your name!From the moment you step onto the inviting covered porch and through the front door, you’ll

  Jeanne Mezzatesta Colony Realty

  107 E Monmouth St, Winchester, VA 22601
• 

  

  /55

  Est $502,142 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  2713 Middle Rd, Winchester, VA 22601

  2713 Middle Rd, Winchester, VA 22601
• 

  

  /41

  $379,000

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  222 Crestwood Ln, Winchester, VA 22602

  Turnkey Living Awaits at 222 Crestwood Lane, Woodbrook Village! Discover the ease and joy of low-maintenance living in the highly sought-after Woodbrook Village, a charming 55+ community. This attractive end unit home at 222 Crestwood Lane is perfectly positioned on a desirable corner lot (non through street) and has been meticulously maintained and tastefully updated, making it an absolute

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  222 Crestwood Ln, Winchester, VA 22602
• 

  

  /39

  $320,000 Sold Oct 10, 2025

  • 2,369 Sq Ft
  • $135/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2007

  102 Elk Trail, Winchester, VA 22602

  Split Foyer with plenty of space and a heck of a view in the private community of Wilde Acres. From your breakfast room you will pan out to see the Shenandoah valley and your private backyard is set with a wooded backdrop. this 4 bedroom abode adopts the sense of open space along with traditional bedroom layout on the main floor with your entertaining room both off the kitchen and in the

  Dave Spence RE/MAX Roots

  102 Elk Trail, Winchester, VA 22602
• 

  

  /52

  Est $538,095 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,243 Sq Ft

  904 W View Ln, Winchester, VA 22601

  904 W View Ln, Winchester, VA 22601
• 

  

  /55

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,494 Sq Ft

  113 Williamson Rd, Winchester, VA 22602

  Charming All-Brick Ranch just minutes from in Prime Winchester Location. Beautifully maintained all-brick ranch just minutes from Jim Barnett Park, Winchester Country Club, shopping, and everyday amenities. This well built home blends timeless craftmanship with modern comfort and offers the ease of low maintenance, energy efficient brick construction. Step inside to discover a spacious main level

  Avis Drummond Long & Foster Real Estate, Inc.

  113 Williamson Rd, Winchester, VA 22602
• 

  

  /53

  $540,000 Sold Oct 10, 2025

  • 2,527 Sq Ft
  • $214/SF
  • 47 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  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
• 

  

  /3

  Est $508,458 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,547 Sq Ft

  2635 Middle Rd, Winchester, VA 22601

  2635 Middle Rd, Winchester, VA 22601
• 

  

  /72

  $699,900

  • 4 Beds
  • 3.5 Baths
  • 3,475 Sq Ft

  132 Amherst St, Winchester, VA 22601

  Price Improvement to make this Yours! Step back in time with this Beautifully preserved VICTORIAN Brick Home Built in 1880, a true piece of Winchester's history. This is a Registered Historic Property that showcases original architectural details, high ceilings, ornate trim, and original wood floors that reflect the artistry of a bygone era. A Well Designed Addition has allowed for generous space

  Jodi Costello ERA Oakcrest Realty, Inc.

  132 Amherst St, Winchester, VA 22601
• 

  

  /32

  $400,000 Sold Oct 09, 2025

  • 2,256 Sq Ft
  • $177/SF
  • 13 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1928

  225 Parkway St, Winchester, VA 22601

  Built in 1928 and fully renovated inside and out, this 4-level home blends historic charm with modern updates in one of Winchester’s most desirable downtown locations.Step inside to discover a thoughtfully redesigned interior featuring refinished hardwood floors, fresh paint throughout, and an all-new kitchen with granite counters, a farm sink, quality plywood cabinetry, and new appliances.

  Tracy Jewell Samson Properties

  225 Parkway St, Winchester, VA 22601
• 

  

  /40

  Est $377,984 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  2717 Blue Ridge Terrace, Winchester, VA 22601

  2717 Blue Ridge Terrace, Winchester, VA 22601
• 

  

  /58

  $635,000

  • 6 Beds
  • 4 Baths
  • 2,672 Sq Ft

  220 Snappy Ln, Winchester, VA 22602

  This stunning two-level home sits on a flat, picturesque 5 acre acre lot, offering endless possibilities for the right buyer.Adding the two lots together is 7.44 acres.The basement was completely remodeled in 2025, featuring a brand-new kitchen, a full bathroom, and plenty of open living space—perfect for guests, recreation, or rental potential. A property with this much land and

  Mauricio Argandona Fairfax Realty Select

  220 Snappy Ln, Winchester, VA 22602
• 

  

  /20

  $340,000 Sold Oct 09, 2025

  • 1,584 Sq Ft
  • $215/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  123 Whirlwind Dr, Winchester, VA 22602

  Welcome home to this beautiful, well maintained, end unit townhome in the highly sought after Windstone community. This spacious townhome has 3 nice size bedrooms, 2 full baths and a powder room on the main level. Open kitchen/dining with sliding glass doors going out onto the deck for the perfect spot to dine outside or just enjoy your morning coffee! Unfinished basement can easily be finished

  Amy Conover Samson Properties

  123 Whirlwind Dr, Winchester, VA 22602
• 

  

  /21

  Est $256,869 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft

  18 Jigsaw Place, Winchester, VA 22601

  18 Jigsaw Place, Winchester, VA 22601
• 

  

  /3

  $1,200,000

  • Land
  • 2.38 Acres
  • $504,202 per Acre

  0 Prosperity Dr, Winchester, VA 22602

  2.38 Acres at the intersection of Valley Pike and Prosperity Drive. Located in the Kernstown area of Frederick County/Winchester. Property is located across from the street from CMA Honda, Aldi Supermarket, Outback Steakhouse, and Carrabba's Italian Grill & Restaurant. Located in close proximity to the intersection of I-81, US Route 37, and US Route 11. Excellent signage opportunities,

  H. Paige Manuel Oakcrest Commercial LLC.

  0 Prosperity Dr, Winchester, VA 22602
• 

  

  /45

  $389,000 Sold Oct 09, 2025

  • 1,558 Sq Ft
  • $250/SF
  • 16 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2004

  106 Candlewick Dr, Winchester, VA 22602

  Welcome Home to this Gable Front Cottage & Relax on your Front Porch. One level living with elegant features: crown moulding, chair railing, shadowboxing, wainscotting, french doors, 6 panel doors, display shelving & cabinetry, gas log fireplace w/hearth & mantel, plantation shutters, roller shades, roman shades, recessed lighting and laminate plank flooring. Enjoy your Kitchen with breakfast

  Wendy Longerbeam Coldwell Banker Elite

  106 Candlewick Dr, Winchester, VA 22602
• 

  

  /29

  Est $245,488 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,160 Sq Ft

  31 Jigsaw Place, Winchester, VA 22601

  31 Jigsaw Place, Winchester, VA 22601
• 

  

  /62

  $1,200,000

  • Land
  • 124 Acres
  • $9,677 per Acre

  0 Frog Hollow Rd, Winchester, VA 22603

  Here’s a piece of pristine land on the market for the first time since the late 70’s with nearly endless possibilities for the next owner(s). This property is located north of Winchester and very near the West Virginia line. This prime piece of real estate has been family owned and operated for decades. Mix of mostly flat hay ground and wooded acreage that stretches to the top of North Mountain.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Frog Hollow Rd, Winchester, VA 22603
• 

  

  /4

  $445,940 Sold Oct 08, 2025

  • 1,590 Sq Ft
  • $280/SF

  • 3 Beds
  • 3.5 Baths
  • Built 2025

  TBD Nepal Ct, Winchester, VA 22602

  Introducing the St. Paul, one of Maronda’s latest townhome designs.The St. Paul offers a range of 1,966 to 1,989 square feet of living space, including 3 to 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious 1-car garage. This new design offers plenty of personalization opportunities to fit your family’s unique needs.On the first floor of the home, you will find a spacious, open-concept floor plan.

  Maronda Homes

  TBD Nepal Ct, Winchester, VA 22602
• 

  

  /42

  Est $331,442 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft

  2513 Hillside Terrace, Winchester, VA 22601

  2513 Hillside Terrace, Winchester, VA 22601
• 

  

  /19

  $400,000

  • 4 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  123 Etnam St, Winchester, VA 22602

  Come see this beautiful home located just off of Rt 50 to the East side of Winchester, great location for commuters, 4br, 2.5 bath with lots of room and storage space. Fenced in backyard with nice 20x16 deck and 8x10 additional deck space off of that for great entertaining. Call agent for combo to visit this listing.

  Heather Sutphin Coldwell Banker Realty

  123 Etnam St, Winchester, VA 22602
• 

  

  /4

  $450,125 Sold Oct 08, 2025

  • 1,590 Sq Ft
  • $283/SF

  • 3 Beds
  • 3.5 Baths
  • Built 2025

  TBD Shouner Ct, Winchester, VA 22602

  Introducing the St. Paul, one of Maronda’s latest townhome designs.The St. Paul offers a range of 1,966 to 1,989 square feet of living space, including 3 to 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious 1-car garage. This new design offers plenty of personalization opportunities to fit your family’s unique needs.On the first floor of the home, you will find a spacious, open-concept floor plan.

  Maronda Homes

  TBD Shouner Ct, Winchester, VA 22602
• 

  

  /53

  Est $278,265 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,741 Sq Ft

  2436 Massanutten Terrace, Winchester, VA 22601

  2436 Massanutten Terrace, Winchester, VA 22601
• 

  

  /38

  $335,000

  • 4 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  298 Bufflick Rd, Winchester, VA 22602

  Meet Convenience with Old World Charm!Welcome to this beautifully renovated home just minutes from Winchester. New is the key to loving this property—with updates inside and out that provide comfort, efficiency, and style.This spacious home features 4 bedrooms, a fully renovated full bath upstairs, and a renovated half bath on the main level. The kitchen has been completely redone with

  Mary Cox Berkshire Hathaway HomeServices PenFed Realty

  298 Bufflick Rd, Winchester, VA 22602
• 

  

  /20

  $305,000 Sold Oct 08, 2025

  • 1,634 Sq Ft
  • $187/SF
  • 95 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2004

  102 Zephyr Ln, Winchester, VA 22602

  Motivated Sellers! Carpet allowance and Professional Cleaning will be provided prior to closing. Don’t miss this opportunity for a Beautifully Updated 3-Bedroom Town home in Prime Location!Welcome to this charming 3-bedroom, 1.5-bath town home located in a highly sought-after neighborhood. Featuring a cozy fireplace in the living room and a stylishly remodeled kitchen with modern finishes,

  Kandi McKenzie Realty ONE Group Old Towne

  102 Zephyr Ln, Winchester, VA 22602
• 

  

  /42

  Est $333,843 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,676 Sq Ft

  2428 Massanutten Terrace, Winchester, VA 22601

  2428 Massanutten Terrace, Winchester, VA 22601
• 

  

  /24

  $25,000

  • Land
  • 1.43 Acres
  • $17,483 per Acre

  LOT 5A Fox Trail, Winchester, VA 22602

  Beautiful building lot located in Mountain Falls Park – Wilde Acres. This is the last lot on the right on Fox Trail, offering excellent privacy and seclusion. The property backs to permanent open space, providing a peaceful setting with mountain views and abundant wildlife. Approved for a 3-bedroom septic system with a certification letter on file. A current survey is also available. This is an

  Nadeem Helfer Corcoran McEnearney

  LOT 5A Fox Trail, Winchester, VA 22602
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  /78

  $670,000 Sold Oct 07, 2025

  • 4,037 Sq Ft
  • $166/SF
  • 77 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2011

  114 Renee Ln, Winchester, VA 22602

  Welcome to 114 Renee Lane – Where Elegance Meets Everyday ComfortThis beautifully appointed home offers the perfect blend of space, sophistication, and modern convenience. Boasting 5 bedrooms and 4 full bathrooms, including a main-level bedroom and full bath ideal for guests or multi-generational living, this residence is designed to accommodate today’s lifestyles.Step inside to

  Laura White ERA Oakcrest Realty, Inc.

  114 Renee Ln, Winchester, VA 22602
• 

  

  /33

  Est $217,420 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  2518 Hockman Ave, Winchester, VA 22601

  2518 Hockman Ave, Winchester, VA 22601
• 

  

  /56

  $424,900

  • 3 Beds
  • 2 Baths
  • 2,326 Sq Ft

  138 Country Club Cir, Winchester, VA 22602

  Charming All-Brick Rancher with Pool Across from Winchester Country ClubThis beautifully maintained 3-bedroom, 2-bath all-brick rancher offers classic charm and modern updates in one of Winchester’s most desirable east-side locations. Featuring a brand-new roof and new windows throughout, this home is move-in ready and designed for both comfort and entertainment.The main level

  Traci Shoberg RE/MAX Roots

  138 Country Club Cir, Winchester, VA 22602
• 

  

  /44

  $650,000 Sold Oct 07, 2025

  • 1,800 Sq Ft
  • $361/SF
  • 237 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  146 Broomsedge Ln, Winchester, VA 22602

  Quality KEE Construction new build. Magnificent views on this private 5 acre lot. Driveway will be paved prior to closing. Daylight basement can be finished if you desire for $80 to $100 per sq ft depending on your choice of finish. Home is complete and ready to move in .

  Meridee Powars Link Realty Services LLC

  146 Broomsedge Ln, Winchester, VA 22602
• 

  

  /76

  Est $460,990 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,095 Sq Ft

  2316 Tower Ave, Winchester, VA 22601

  2316 Tower Ave, Winchester, VA 22601
• 

  

  /67

  $399,999

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

  707 E Cork St, Winchester, VA 22601

  Don't let this location fool you - Plenty of parking on the side and back of the home and a large turn around space to exit onto Cork St easily! Centrally located colonial with gorgeous hardwood flooring and trim throughout! Step back in time, but enjoy all of the modern amenities with easy access to Jim Barnett Park just down the street, downtown walking mall and commuter roads, and even views

  Misty Weaver Samson Properties

  707 E Cork St, Winchester, VA 22601
• 

  

  /50

  $450,000 Sold Oct 06, 2025

  • 2,680 Sq Ft
  • $168/SF
  • 15 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1945

  25 E Hart St, Winchester, VA 22601

  Welcome to 25 E Hart Street! Nestled in the heart of downtown Winchester, this beautifully updated 5-bedroom, 3-bath home is the perfect mix of charm, space, and convenience. Step inside to a bright, spacious living room where a wood-burning fireplace provides the perfect spot to relax and unwind. The updated kitchen is a dream with quartz countertops, stainless steel appliances, crisp white

  Liz Owings RE/MAX Roots

  25 E Hart St, Winchester, VA 22601

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