Winchester, VA Homes

• 

  

  

  /34

  Est $583,346 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,550 Sq Ft

  673 Hillman Dr, Winchester, VA 22601

  673 Hillman Dr, 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
• 

  

  

  /37

  $268,000 Sold Jul 22, 2025

  • 1,214 Sq Ft
  • $221/SF
  • 13 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1996

  104 Braeburn Dr, Winchester, VA 22601

  Turnkey and full of charm, this brick-front townhome offers an ideal location near Route 7 and I-81. Inside, enjoy an open flow, warm natural light, and fresh updates throughout. The family room features hardwood floors and a bay window, while the kitchen boasts ceramic tile and gas cooking. A laundry room with washer and dryer on the main level adds convenience. Upstairs, the spacious primary

  Steph Mitchell Samson Properties

  104 Braeburn Dr, Winchester, VA 22601
• 

  

  

  /20

  Est $572,622 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,550 Sq Ft

  661 Hillman Dr, Winchester, VA 22601

  661 Hillman Dr, 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
• 

  

  /12

  $145,000 Sold Jul 21, 2025

  • 7 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1941

  381 National Ave, Winchester, VA 22601

  ***OFFER DEADLINE: SUNDAY JUNE 22ND AT 8PM!***Calling all investors, builders, and renovation enthusiasts—this is the opportunity you've been waiting for! This property is a true blank canvas with tons of potential. The home has been completely gutted and is ready for your vision—whether you're planning to renovate, rebuild, or start from scratch, the possibilities are wide open! With over

  Kevin Rodriguez Weichert, REALTORS

  381 National Ave, Winchester, VA 22601
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  /45

  Est $534,240 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,825 Sq Ft

  653 Hillman Dr, Winchester, VA 22601

  653 Hillman Dr, Winchester, VA 22601
• 

  

  /86

  $649,999

  • 4 Beds
  • 3 Baths
  • 3,442 Sq Ft

  121 Sweetbriar Ln, Winchester, VA 22603

  "Private haven Rancher" on 13 plus acres with 4 Bedrooms and 3 full baths. Hardwood floors throughout home. See-thru Fireplace between Dining room and Living room. Recent upgraded kitchen with new flooring ,counter tops and fresh paint. Owners' Suite has bathroom w/whirlpool tub, separate shower, double sinks and French door access to the rear deck. Finished basement with full bath, bedroom,

  Andrew Hensley Samson Properties

  121 Sweetbriar Ln, Winchester, VA 22603
• 

  

  /23

  $365,000 Sold Jul 21, 2025

  • 1,680 Sq Ft
  • $217/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2022

  116 Copeley Cir, Winchester, VA 22602

  Beautifully appointed garage townhome available now in Freedom Manor. Less than 3 years old and ideally located on one of the best lots in the neighborhood! Fantastic floor plan offering that highly desirable main level entry making this the home you want for easy living and minimal stairs. Just a few of the interior upgrades include warm luxury vinyl plank flooring spanning the entire main level

  Mike Casto Weichert, REALTORS

  116 Copeley Cir, Winchester, VA 22602
• 

  

  /24

  Est $499,690 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,395 Sq Ft

  649 Hillman Dr, Winchester, VA 22601

  649 Hillman Dr, Winchester, VA 22601
• 

  

  /72

  $695,000

  • 5 Beds
  • 4 Baths
  • 4,387 Sq Ft

  3949 N Frederick Pike, Winchester, VA 22603

  You will feel the peace and harmony the moment you come up the drive, this is your new home place. Almost 4 unrestricted acres for you to spread your wings. The sweet spots here will truly tug at your heart, the hammock area for lazy day reading, the fire pit with the most incredible mountain views in the fall and winter months, The four wheeler trails begging for fun and memories!! The

  Kristen Kerns Roberts Realty Group, LLC

  3949 N Frederick Pike, Winchester, VA 22603
• 

  

  /67

  $690,000 Sold Jul 21, 2025

  • 3,426 Sq Ft
  • $201/SF
  • 9 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2001

  960 Laurel Grove Rd, Winchester, VA 22602

  Interior photos to come!Welcome to 960 Laurel Grove Road — a peaceful retreat nestled in the scenic countryside of Winchester, VA. This charming property offers the perfect blend of comfort, space, and privacy, making it an ideal home for those seeking a quiet lifestyle without sacrificing convenience.Set on a generous lot surrounded by mature trees and natural beauty, this home

  Matt Leiva Keller Williams Realty

  960 Laurel Grove Rd, Winchester, VA 22602
• 

  

  /34

  Est $578,355 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,509 Sq Ft

  906 Wayne Dr, Winchester, VA 22601

  906 Wayne Dr, Winchester, VA 22601
• 

  

  /54

  $860,000 Open Sat 1PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 5,254 Sq Ft

  1504 Brookdale Ct, Winchester, VA 22601

  MOTIVATED SELLER! Over 5,250 sq ft in this stunning 5BR/3.5BA Home in Prime Meadow Branch Area!Elegant 2-story foyer with sweeping staircase, coffered ceilings, and extended-height windows. Family room features floor-to-ceiling stone fireplace, open to gourmet kitchen with quartz countertops, stainless steel appliances, cooktop, and wall oven. Main level office with French doors, formal

  Julie Shiley Coldwell Banker Realty

  1504 Brookdale Ct, Winchester, VA 22601
• 

  

  /61

  $525,000 Sold Jul 21, 2025

  • 3,440 Sq Ft
  • $153/SF
  • 17 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  3296 Apple Pie Ridge Rd, Winchester, VA 22603

  Tucked away on 1.66 scenic acres, this beautifully updated ranch-style home blends the serenity of country living with unbeatable convenience—just 10 minutes from downtown Winchester. Ideally located off Apple Pie Ridge Road, you’re within 15 minutes of the hospital and major highways, yet a world away from the hustle. Step inside and soak in over 3,400 sqft of freshly renovated living space,

  Christian Davis RE/MAX Executives

  3296 Apple Pie Ridge Rd, Winchester, VA 22603
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  /32

  Est $344,210 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,052 Sq Ft

  808 Appleseed Ct, Winchester, VA 22601

  808 Appleseed Ct, Winchester, VA 22601
• 

  

  /5

  $265,000

  • 4 Beds
  • 1 Bath
  • 1,732 Sq Ft

  1006 S Cameron St, Winchester, VA 22601

  Don't miss out on this opportunity to own this 5 bedroom/1 bath home. Hardwood flooring throughout. Large, covered front porch and rear deck. Less than a mile from downtown Winchester & the Handley Library. Close to schools. Off-street parking and a spacious backyard. Access to alley from backyard and off-street parking.

  Sheila Pack RE/MAX Roots

  1006 S Cameron St, Winchester, VA 22601
• 

  

  /22

  $350,000 Sold Jul 21, 2025

  • 1,060 Sq Ft
  • $330/SF
  • 66 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  601 Fairview Ave, Winchester, VA 22601

  Fully Renovated Gem in the Heart of Winchester! Welcome to 601 Fairview Ave, where modern upgrades meet timeless charm! This beautifully remodeled 3-bedroom, 2-bathroom rambler offers the perfect blend of comfort and convenience in one of Winchester’s most desirable locations.Step inside to discover a brand-new kitchen featuring stylish finishes, sleek countertops, and modern

  Jorge Najarro Samson Properties

  601 Fairview Ave, Winchester, VA 22601
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  /15

  Est $336,919 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,052 Sq Ft

  801 Appleseed Ct, Winchester, VA 22601

  801 Appleseed Ct, Winchester, VA 22601
• 

  

  /8

  $25,000

  • Land
  • 0.51 Acre
  • $49,020 per Acre

  LOT 85 Mimosa, Winchester, VA 22602

  Mimosa Trail- Beautiful Mountain Views. Build your dream home on this Large .51 acre Lot. 3 bedroom Perc, Certification Letter and Plat. Breathtaking Mountain Views, Quiet Rural area still close to Hospital, Shopping, Schools, Rt.37 & I 81. Enjoy the amenities, Fishing Lake & Ponds, Beach area, Recreational Park area, Picnic Pavilion, Golf pads, Ball Field & Streams. Sanitary District Fee

  Gina Griffith MarketPlace REALTY

  LOT 85 Mimosa, Winchester, VA 22602
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  /28

  $488,990 Sold Jul 21, 2025

  • 1,953 Sq Ft
  • $250/SF
  • 114 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  101 Monacan St, Winchester, VA 22602

  The Pine is a popular floorplan for all the right reasons! 4 bedrooms, 2.5 bathrooms, and a 2-car garage. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for seating, an impressive corner pantry, plenty of cabinet space and stainless-steel appliances that

  Tracy Jennings D R Horton Realty of Virginia LLC

  101 Monacan St, Winchester, VA 22602
• 

  

  /45

  Est $560,523 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,437 Sq Ft

  722 Chelsea Dr, Winchester, VA 22601

  722 Chelsea Dr, Winchester, VA 22601
• 

  

  /8

  $1,400,000

  • Land
  • 5.73 Acres
  • $244,328 per Acre

  1667 N Frederick Pike, Winchester, VA 22603

  Great highway exposure exposure to state route 37 the bypass around the West side of Winchester and and 5222 north or North Frederick Pike entrance at a signalized intersection

  John Scully Colony Realty

  1667 N Frederick Pike, Winchester, VA 22603
• 

  

  /11

  $270,000 Sold Jul 18, 2025

  • 1,524 Sq Ft
  • $177/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  147 Country Park Dr, Winchester, VA 22602

  Opportunity knocks at 147 Country Park Dr—an affordable home with loads of potential in a prime commuter-friendly location on the east side of Winchester. Just minutes to Old Town, shopping, schools, and Route 7, this is a perfect chance to build sweat equity and make this home your own!This split foyer layout offers 2 bedrooms and 1 full bath upstairs, with an additional bedroom, bonus

  Bradley Comstock ERA Oakcrest Realty, Inc.

  147 Country Park Dr, Winchester, VA 22602
• 

  

  /24

  Est $198,975 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,183 Sq Ft

  2130 Douglas St, Winchester, VA 22601

  2130 Douglas St, Winchester, VA 22601
• 

  

  /58

  $1,099,000

  • 6 Beds
  • 5.5 Baths
  • 6,540 Sq Ft

  1020 Breckinridge Ln, Winchester, VA 22601

  Buy your new home and enjoy a 1% lower interest rate for the first year with a temporary buydown incentive - helping make your first year of homeownership more affordable! Ask for details! Approximately 6,000 finished square feet of living space! A place to grow, gather, and stay awhile! From the moment you arrive, this property greets you with thoughtful details and a sense of home you

  Sheila Pack RE/MAX Roots

  1020 Breckinridge Ln, Winchester, VA 22601
• 

  

  /39

  $370,000 Sold Jul 18, 2025

  • 1,050 Sq Ft
  • $352/SF
  • 4 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1968

  625 Butler Ave, Winchester, VA 22601

  This house has been remodeled and offers five bedrooms and 2.5 bathrooms. The open concept is evident in the easy-flowing floor plan. Beautiful kitchen quartz countertops, 42-inch cabinets and stainless steel appliances. Freshly painted, tastefully renovated bathrooms, new floors throughout, recess lighting, newer windows, driveway, and garage. Walkout basement with two big bedrooms and a

  Aracely Rivera First Decision Realty LLC

  625 Butler Ave, Winchester, VA 22601
• 

  

  /30

  Est $369,234 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,550 Sq Ft

  2047 Stoneleigh Dr, Winchester, VA 22601

  2047 Stoneleigh Dr, Winchester, VA 22601
• 

  

  /11

  $99,500

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

  108 Lugano Place Unit A52, Winchester, VA 22603

  This gorgeous 3 bed/2 bath home was manufactured in 2015, it has 1248.00 sq. ft. of beautiful living space. This newly renovated home comes with new flooring throughout the home, all new appliances, custom cabinetry with coffee nook and granite countertops. The masterbath comes with 2 sinks, linen closet, walkin shower and a custom closet. The 2 bedrooms also comes with custom closet and granite

  Kristina Kelly Regency Lakes

  108 Lugano Place Unit A52, Winchester, VA 22603
• 

  

  /34

  $402,500 Sold Jul 18, 2025

  • 1,475 Sq Ft
  • $273/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  350 Poorhouse Rd, Winchester, VA 22603

  Located in a quiet and well-established Area convenient to shopping, Historic downtown Winchester, Valley Health and Schools. The ease of one-level living, a flexible floor plan, and a generous 2+ Acre lot with a pond make this house a home! This 3-bedroom, 2-bath ranch-style home features a traditional layout with defined living spaces, including a front living room, and a dedicated dining

  LESLIE WEBB Long & Foster Real Estate, Inc.

  350 Poorhouse Rd, Winchester, VA 22603
• 

  

  /25

  Est $366,373 Not Listed For Sale

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

  2067 Stoneleigh Dr, Winchester, VA 22601

  2067 Stoneleigh Dr, Winchester, VA 22601
• 

  

  /40

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1709 Reaves St, Winchester, VA 22601

  Please take off shoes and give feedback. Step into this beautifully cared-for home featuring new roof (2023) New HVAC System (2024) new LVP floors throughout the basement a spacious, inviting layout. The large kitchen offers plenty of room for meal prep and flows effortlessly into the dining and living rooms — perfect for family gatherings and entertaining. The finished basement boasts a

  Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

  1709 Reaves St, Winchester, VA 22601
• 

  

  /26

  $235,000 Sold Jul 18, 2025

  • 704 Sq Ft
  • $334/SF
  • 34 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1988

  1502 Tomahawk Trail, Winchester, VA 22602

  BACK ON THE MARKET!! Nestled about 20 minutes from downtown Winchester, this charming two-bedroom home may be just what you need to escape city life! Perfect for a primary residence or a part-time getaway, the property is nestled on two lots equaling nearly one acre. Once inside, you'll feel right at home with warm and inviting wood tones. The open living-dining area provides a comfortable space

  Kristin Crosby Samson Properties

  1502 Tomahawk Trail, Winchester, VA 22602
• 

  /2

  Est $396,229 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  2066 Honeysuckle Ln, Winchester, VA 22601

  2066 Honeysuckle Ln, Winchester, VA 22601
• 

  

  /32

  $244,900

  • 3 Beds
  • 2 Baths
  • 1,070 Sq Ft

  311 Ash Hollow Dr, Winchester, VA 22602

  Opportunity awaits in Ash Hollow Estates! This 3-bedroom, 2-bath townhouse is full of potential—solid bones, a smart layout, and endless possibilities for transformation. Whether you're an investor or a first-time buyer ready to create something special, this home is the perfect canvas. With a little TLC, a fresh new look is on the horizon! New carpet installed as of August 2025 adds a clean,

  Josh Medina ERA Oakcrest Realty, Inc.

  311 Ash Hollow Dr, Winchester, VA 22602
• 

  

  /48

  $260,000 Sold Jul 18, 2025

  • 1,340 Sq Ft
  • $194/SF
  • 34 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1930

  21 W Pall Mall St, Winchester, VA 22601

  "Bring Your Vision To W Pall Mall" This 4 bedroom, 1 full bath home is perfect if you're looking for a renovation! Right in the heart of Winchester City within walking distance to the Old Town Walking Mall where you can enjoy excellent food, shopping and more! The first floor has a great sized living room, dining room and kitchen. 4 bedrooms on the upper level, full bathroom, walk-up attic and an

  Matt Kilmer Samson Properties

  21 W Pall Mall St, Winchester, VA 22601
• 

  

  /36

  Est $374,706 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  1995 Cidermill Ln, Winchester, VA 22601

  1995 Cidermill Ln, Winchester, VA 22601
• 

  

  /18

  $299,000

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  Welcome home to 711 E. Cork Street! Centrally located in Winchester, VA. Enjoy the ease of access to downtown Winchester, Jim Barnett Park, shopping, and commuter routes. This 2 bedroom 1 1/2 bath detached home with brand new exterior update(new vinyl siding). Deeded right away provides access to rear of the property. The right of way is not the actual gravel driveway in place

  Jim Stafford ERA Oakcrest Realty, Inc.

  711 E Cork St, Winchester, VA 22601
• 

  

  /20

  $450,000 Sold Jul 18, 2025

  • 1,657 Sq Ft
  • $272/SF
  • 69 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  111 Yurok Ct, Winchester, VA 22602

  The Cabral offers 1,657 square feet of thoughtfully designed living space, featuring 3 spacious bedrooms, 2.5 bathrooms, and a versatile loft area on the bedroom level—perfect for a home office, playroom, or additional lounge space. Enjoy the convenience of a 2-car garage and modern finishes throughout. This home is move-in ready and comes with added perks including a washer and dryer,

  Brooks Sears D R Horton Realty of Virginia LLC

  111 Yurok Ct, Winchester, VA 22602
• 

  

  /35

  Est $371,394 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,748 Sq Ft

  2081 Cidermill Ln, Winchester, VA 22601

  2081 Cidermill Ln, Winchester, VA 22601

Showing Results 641 - 680, Page 17 of 18