Winchester, VA Homes for Sale

• 

  

  

  /10

  $85,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  108 Dwayne Place Unit A135, Winchester, VA 22603

  Welcome to Regency Lakes a all age active and vibrant community, where you can find yourself in your dream home. We have a beautiful, well maintained 1995 3 bed, 2 bath home featuring 1512.00 sq ft of beautifully designed living space. Located Winchester, this property offers the perfect blend of modern amenities and timeless charm. Step inside to find a beautiful and functional stone fireplace

  Kristina Kelly Regency Lakes

  108 Dwayne Place Unit A135, Winchester, VA 22603
• 

  

  

  /63

  $365,000 Open Fri 11AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,520 Sq Ft

  508 Grouse Dr, Winchester, VA 22602

  Nestled in the charming Wilde Acres community, this stunning new construction home, completed in 2025, offers a perfect blend of modern design and traditional comfort. The Colonial architectural style, adorned with durable vinyl siding, invites you into a warm and welcoming space. Step inside to discover a thoughtfully designed interior featuring a traditional floor plan that seamlessly connects

  Steve DuBrueler Coldwell Banker Premier

  508 Grouse Dr, Winchester, VA 22602
• 

  

  

  /11

  $4,000,000

  • Land
  • 19 Acres
  • $210,526 per Acre

  368 Victory Rd, Winchester, VA 22602

  19 Acres, Prime Commercial or FLEX Development Opportunity! Zoned B2, General Commercial. Major commuter corridor to Northern VA, adjacent to Airport Business Park, FBI Records Center, Navy Federal Credit Union headquarters, and new One Logistics Park. Also #1 commuter route to Northern VA! Excellent visibility, flat topo, and dual access on Victory Lane and Independence! Sale includes 14.06

  Gillian Greenfield Coldwell Banker Premier

  368 Victory Rd, Winchester, VA 22602
• 

  

  

  /52

  $410,000

  • 3 Beds
  • 4 Baths
  • 2,100 Sq Ft

  128 Killbuck Trail, Winchester, VA 22602

  Welcome to 128 Killbuck Trail, a beautifully maintained 2019 split-foyer home that truly shows like new. Freshly painted throughout, this residence features granite countertops in the kitchen and bathrooms and has an open, inviting floor plan perfect for everyday living and entertaining.The main level offers three spacious bedrooms, including a primary suite with an en-suite bath. The lower

  Leah Clowser RE/MAX Roots

  128 Killbuck Trail, Winchester, VA 22602
• 

  

  

  /43

  $592,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 3,619 Sq Ft

  125 Mascouten St, Winchester, VA 22602

  Quick Move-In Salem! This spacious 6 bedroom, 4.5 bath home offers 2,686 sq ft on the top two floors with a first-floor primary suite for easy main-level living. The open-concept design is perfect for entertaining, and the stone front elevation adds timeless curb appeal. Enjoy the added space of a finished recreation room with an additional bedroom—ideal for guests or a home office. Ask about

  D.R. Horton Builder

  125 Mascouten St, Winchester, VA 22602
• 

  

  /8

  $785,000 New Construction

  • 3 Beds
  • 3 Baths
  • 2,548 Sq Ft

  0 Apple Pie Ridge Rd Unit VAFV2039276, Winchester, VA 22603

  Dogwood - One Story Living Carrington Homes Western Loudoun’sPremiere Home builder introduces its newWinchester Collection of single familyHomes on a private 2 acre lot.Custom style homes designedBy James McDonald Architects One story and two story plans withFirst floor multi generational options available DECORATED MODELS located at 156 Covey Lane Winchester

  Daniel Boris Pearson Smith Realty, LLC

  0 Apple Pie Ridge Rd Unit VAFV2039276, Winchester, VA 22603
• 

  

  /36

  $410,000

  • 4 Beds
  • 3.5 Baths
  • 2,261 Sq Ft

  125 Cheshire Ct, Winchester, VA 22602

  Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-sac on the east side of Winchester. Conveniently located to Rt 7 and I-81 and historic downtown Winchester. The 3-level townhouse backs to a wooded tree area and has a fenced rear yard. New luxury vinyl floor installed in majority of the home. As you enter, you will be welcomed into a large foyer with

  Eric Kronenwetter RE/MAX Roots

  125 Cheshire Ct, Winchester, VA 22602
• 

  

  /33

  $245,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  815 Pheasant Dr, Winchester, VA 22602

  Affordable and move-in ready ranch-style home on a little more than a half acre. The mature trees, abundant wildlife, and quiet location make this a serene location. Featuring 2 bedrooms and 1 full bath, this home was freshly painted (Nov 2025) and underwent a major renovation in 2017 (roof, HVAC, water heater, floors, fixtures, and more). Enjoy the comfort of 1-level living with plenty of

  Eric Kronenwetter RE/MAX Roots

  815 Pheasant Dr, Winchester, VA 22602
• 

  

  /39

  $579,990 New Construction

  • 6 Beds
  • 4 Baths
  • 3,127 Sq Ft

  HAYDEN Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Hayden is a two-story plan with 6 bedrooms and 3 bathrooms in over 3,100 total square feet. The main level features a flex room adjacent to the foyer, ideal for a formal dining room or home office. The gourmet kitchen has an oversized island for extra seating and a large pantry, and it opens to the dining area and a spacious living room. A bedroom with a full bathroom completes the main

  D.R. Horton Builder

  137 Seminole Dr Unit 36203781, Winchester, VA 22602
• 

  

  /24

  $374,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 1,752 Sq Ft

  123 Castaway Place, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  123 Castaway Place, Winchester, VA 22603
• 

  

  /42

  $1,550,000

  • Land
  • 128.56 Acres
  • $12,057 per Acre

  Lot 1 (128.556 Acres Laurel Grove Rd, Winchester, VA 22602

  Welcome to a truly rare offering — a first-time release of an extraordinary 128+ acre estate parcel, perfectly suited for the discerning buyer seeking privacy, natural beauty, and limitless potential. This is one of only three exclusive lots masterfully curated from a 439-acre legacy estate, designed with elegance, intention, and long-term value in mind.Tucked behind private, impeccably

  Nadeem Helfer Corcoran McEnearney

  Lot 1 (128.556 Acres Laurel Grove Rd, Winchester, VA 22602
• 

  

  /36

  $529,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,415 Sq Ft

  ELM Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  Introducing the Elm, a contemporary 2,415 square feet two-story home, featuring five bedrooms, three bathrooms, a loft, and a two-car garage. As you step into the distinct foyer you will appreciate the open concept floorplan. The spacious kitchen boasts an abundance of cabinetry and counter space, an ample walk-in pantry, a large island with room for seating and stainless-steel appliances. The

  D.R. Horton Builder

  137 Seminole Dr Unit 36203780, Winchester, VA 22602
• 

  

  /22

  $399,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,094 Sq Ft

  2420 Swansong Place, Winchester, VA 22603

  The three-level Skyline model masterfully combines a traditional exterior with a contemporary, open-concept floor plan. On the main level, you’ll find an expansive living room, bathed in natural light from numerous windows, flows effortlessly into the dining area and kitchen. The kitchen is designed with an L-shaped countertop and an island that borders the dining room. A cozy nook serves as a

  Brookfield Residential Builder

  2420 Swansong Place, Winchester, VA 22603
• 

  

  /17

  $339,900 Open Sat 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  2952 Grace St, Winchester, VA 22601

  Charming one level, 3-bedroom, 1 full bath home conveniently located in the heart of Winchester. Recently remodeled with new flooring throughout, updated bathroom, and modern fixtures. Thoughtful updates make this home move-in ready and ideal for easy, single-level living. Close to shopping, dining, and commuter routes.

  Carolina Mosquera Weichert, REALTORS

  2952 Grace St, Winchester, VA 22601
• 

  

  /33

  $589,000

  • 3 Beds
  • 2 Baths
  • 1,974 Sq Ft

  832 Winder Ct, Winchester, VA 22601

  All-brick rancher located in the sought-after Early’s Green at Meadow Branch community, offering 1,974 finished square feet with 9-foot ceilings and true one-level living. The open floor plan provides excellent flow and is ideal for both everyday living and entertaining. Recent interior updates include new hardwood flooring in the main living room, new carpet in all bedrooms, and fresh interior

  Barton Chasler Realty ONE Group Old Towne

  832 Winder Ct, Winchester, VA 22601
• 

  

  /39

  $576,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,865 Sq Ft

  CLIFTON Plan at Willow Run, Winchester, VA 22601

  The Clifton by D.R. Horton is a stunning new construction, ranch home plan featuring 1,865 square feet of living space, 3 bedrooms, 2 bathrooms, and a 2-car garage. With a roomy and flexible floor plan, the Clifton is just as inviting as it is functional! Prepare to be enchanted by the spacious kitchen, equipped with brand-new stainless-steel appliances, sleek countertops, and cabinets that offer

  D.R. Horton Builder

  105 Trellis View Ln Unit 36406655, Winchester, VA 22601
• 

  

  /47

  $619,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 2,632 Sq Ft

  123 Wappinger Terrace, Winchester, VA 22602

  Quick Move-In Salem! This spacious 6 bedroom, 4.5 bath home offers 2,686 sq ft on the top two floors with a first-floor primary suite for easy main-level living. The open-concept design is perfect for entertaining, and the stone front elevation adds timeless curb appeal. Enjoy the added space of a finished recreation room with an additional bedroom—ideal for guests or a home office. Ask about

  D.R. Horton Builder

  123 Wappinger Terrace, Winchester, VA 22602
• 

  

  /6

  $20,000

  • Land
  • 0.46 Acre
  • $43,478 per Acre

  Lot 102 Bow Wood Trail, Winchester, VA 22602

  A Hidden Gem Waiting for YouNestled in the serene countryside of Winchester, Virginia, lies a great treed building lot on the lower side of Shawneeland. This picturesque piece of land offers the perfect blend of seclusion and convenience, making it an ideal location for building your dream home.Enjoy the tranquility and natural beauty of Shawneeland's private parks, perfect for relaxing

  Rick Guthrie Keller Williams Realty

  Lot 102 Bow Wood Trail, Winchester, VA 22602
• 

  

  /12

  $290,000

  • 2 Beds
  • 1 Bath
  • 817 Sq Ft

  580 York Ave, Winchester, VA 22601

  Charming and completely updated! This beautiful home features a brand-new kitchen with new appliances, an updated bathroom, newly installed HVAC system, and a new water heater. Truly move-in ready and waiting for its next owner!

  Yoselin Mejia The Vasquez Group LLC

  580 York Ave, Winchester, VA 22601
• 

  

  /25

  $279,900

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  111 Genesee Trail, Winchester, VA 22602

  Remodeled rancher on 4 lots totaling 1.41 acres. Cute 2 bedroom 1 bath home freshly painted with new luxury vinyl planking throughout the entire house. Brand new bathroom with tub /shower. Open floor plan with bedrooms on each end of the house for privacy. 2 sheds that convey to store whatever your heart desires. Front deck to be stained as soon as weather permits. Shawnee Land is in a sanitary

  Jacquelyn Rizzari MarketPlace REALTY

  111 Genesee Trail, Winchester, VA 22602
• 

  

  /51

  $1,595,000

  • Land
  • 158.44 Acres
  • $10,067 per Acre

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602

  Incredible opportunity to own 158.443 acres of pristine, private land in an exclusive 3-lot, 440-acre subdivision. This is the most secluded parcel of the three, offering unmatched 360-degree panoramic views and a level of privacy that’s increasingly rare—yet just 15 minutes from town. Tucked away from the lights and sounds of civilization, this property provides a peaceful, off-the-beaten-path

  Nadeem Helfer Corcoran McEnearney

  158.5 Acres Lot 3 Laurel Grove Rd, Winchester, VA 22602
• 

  /2

  $549,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,958 Sq Ft

  118 Scented Rose Way, Winchester, VA 22602

  The Dover by D.R. Horton is a stunning new construction, ranch home plan featuring 1,958 square feet of living space with 3 bedrooms, 2 bathrooms and a 2-car garage.The foyer welcomes you in with two versatile bedrooms, sharing a well-appointed full bathroom. As you continue down the foyer, you’ll find a spacious office, coat closet, and laundry room. At the heart of the home is the kitchen,

  Brooks Sears D R Horton Realty of Virginia LLC

  118 Scented Rose Way, Winchester, VA 22602
• 

  

  /45

  $449,000 Coming Soon

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

  25 W Southwerk St, Winchester, VA 22601

  Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers the perfect balance of neighborhood tranquility and

  Dan Whitacre Colony Realty

  25 W Southwerk St, Winchester, VA 22601
• 

  

  /33

  $576,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,865 Sq Ft

  55 Hydrangea Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 sq. ft. ranch home, blending style and functionality in a single-level open layout. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The kitchen opens to a large great room with two windows that let in

  Brooks Sears D R Horton Realty of Virginia LLC

  55 Hydrangea Way, Winchester, VA 22602
• 

  

  /12

  $632,990 New Construction

  • 3 Beds
  • 2 Baths
  • 3,056 Sq Ft

  5 Williamson Rd, Winchester, VA 22602

  Welcome to Abrams Pointe, featuring new single-family homes in an established Winchester neighborhood, complete with wooded cul-de-sac homesites. The Drexel Floorplan is a spacious and versatile single-family home designed to suit a variety of lifestyles. With up to 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features

  Dick Bryan New Home Star Virginia, LLC

  5 Williamson Rd, Winchester, VA 22602
• 

  

  /45

  $399,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  127 Lakota St, Winchester, VA 22602

  Don't miss this fantastic Adams interior unit townhome with included deck, washer and dryer, and blinds! The Adams offers 4 bedrooms, 3.5 baths, and a 1-car garage spread across three levels with a total of 1,889 square feet. The main level features 9-foot ceilings, luxury vinyl plank flooring, white cabinets with granite countertops, and stainless steel appliances by Whirlpool. With all the

  D.R. Horton Builder

  127 Lakota St, Winchester, VA 22602
• 

  

  /59

  $889,000

  • 5 Beds
  • 4.5 Baths
  • 4,957 Sq Ft

  1540 Meadow Branch Ave, Winchester, VA 22601

  An exceptional offering of luxury living in the City of Winchester, this stately brick residence presents 4,958 square feet or refined, custom-designed living space. The home features 5 generously sized bedrooms and 4.5 beautifully appointed bathrooms, thoughtfully crafted for both elegant entertaining and everyday comfort. Rich architectural details and custom finishes are showcased throughout,

  John Schroth Colony Realty

  1540 Meadow Branch Ave, Winchester, VA 22601
• 

  

  /3

  $384,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,966 Sq Ft

  105 Bonnings Dr, Winchester, VA 22603

  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 Builder

  105 Bonnings Dr, Winchester, VA 22603
• 

  /2

  $300,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,789 Sq Ft

  501 Battle Ave, Winchester, VA 22601

  Unwind on the covered front porch of this charming stone Cape Cod, ideally located on a spacious corner lot with sidewalks and a large, fenced backyard. Inside, the inviting living room features hardwood floors and a brick gas-log fireplace—perfect for cozy evenings. Hardwood flooring continues throughout the home, complemented by a convenient kitchen and dining combination. Two bedrooms are

  Susan Caulfield Pearson Smith Realty, LLC

  501 Battle Ave, 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 Samson Properties

  Lot A Cather Ln, Winchester, VA 22602
• 

  

  /21

  $384,900

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

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
• 

  

  /26

  $624,990 New Construction

  • 3 Beds
  • 1 Bath
  • 3,122 Sq Ft

  110 Lawford Way, Winchester, VA 22603

  Welcome home to the Rockwell, a versatile main-level living home designed for your lifestyle. The Rockwell's open-concept main floor seamlessly blends the kitchen, breakfast nook, and family room, creating a spacious and inviting atmosphere. The kitchen is a culinary enthusiast's dream, featuring a functional island with optional extension, ample storage, and a butler's pantry. The adjacent

  Brookfield Residential Builder

  110 Lawford Way, Winchester, VA 22603
• 

  

  /22

  $79,900

  • 3 Beds
  • 2 Baths
  • 1,118 Sq Ft

  107 Smith Dr, Winchester, VA 22603

  Resort-Style Living at Regency Lakes! Enjoy an amenity-rich community that also offers easy access to route 7 and many shopping and dining options nearby. The home features vinyl flooring in the main living areas and carpet in the bedrooms. A light and bright kitchen is the heart of the home, with plenty of storage and counterspace. A charming breakfast nook and laundry closet add convenience to

  Heloisa Amar Samson Properties

  107 Smith Dr, Winchester, VA 22603
• 

  

  /98

  $669,000

  • 6 Beds
  • 4.5 Baths
  • 4,124 Sq Ft

  461 Skylar Lanes Way, Winchester, VA 22603

  Welcome to 461 Skylar Lanes Way, a stunning home nestled on over 2 acres in the upscale & sought after Walnut Springs Estates community, with just minutes from downtown Winchester! This spacious residence offers 6 bedrooms, 4.5 bathrooms, finished basement and a 3-car side load garage with a circular paved driveway, providing plenty of room for family, guests, and entertaining. Step inside the

  Michele Gibson Samson Properties

  461 Skylar Lanes Way, Winchester, VA 22603
• 

  /2

  $69,900

  • Land
  • 0.19 Acre
  • $367,895 per Acre

  Lot 84 Purcell Ln, Winchester, VA 22603

  Build Your Vision Near Winchester City LimitsPrime buildable lot offering the perfect balance of convenience and freedom. Located just minutes from Winchester City but still in county, shopping, the hospital, and Route 37, this property is ready for your project with public water and sewer hookups available. Freedom to Build: No HOA or restrictive covenants—ideal for a custom small home or a

  Jim Thomson Realty ONE Group Old Towne

  Lot 84 Purcell Ln, Winchester, VA 22603
• 

  

  /27

  $364,990 New Construction

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

  DELMAR Plan at Retreat at Winding Creek - Townhomes, Winchester, VA 22602

  The Delmar by D.R. Horton is a stunning new construction 2 story townhome plan featuring 1,500 square feet of living space including 3 bedrooms, 2.5 baths and a 1-car garage. The convenience of townhome living meets the amenities of a single-family home with the Delmar. The main level eat-in kitchen with large pantry and modern island opens up to an airy, bright dining and living room. The upper

  D.R. Horton Builder

  137 Seminole Dr Unit 36203785, Winchester, VA 22602
• 

  /2

  $500,000

  • Studio
  • 1,175 Sq Ft

  513 and 525 Monticello St, Winchester, VA 22601

  For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

  Brett Haynes Oakcrest Commercial LLC.

  513 and 525 Monticello St, Winchester, VA 22601
• 

  

  /17

  $169,900

  • Land
  • 49.61 Acres
  • $3,425 per Acre

  0 Rockwood Trail Unit 49.61 ACRES, Winchester, VA 22602

  A great many buyers are looking for decent acreage, views, the ability to hunt and shoot, the opportunity to get away on the weekends with privacy and with potential for a family retreat and maybe even future retirement. This listing clicks all the boxes. This one is on top the mountain with hard surfaced roads all the way to the top. The name of the subdivision is Great Mountain Wilderness.

  Edward Beightol Cedar Creek Real Estate

  0 Rockwood Trail Unit 49.61 ACRES, Winchester, VA 22602
• 

  

  /7

  $1,100,000

  • Land
  • 2.3 Acres
  • $478,261 per Acre

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

  2.3 Acre Outparcel on Pleasant Valley Road for Sale Neighbors include Walmart, Ross, Target, Panera Bread, Olive Garden, Petco, and the list goes on! Zoned CM1, ideal for auto sales, offices, retail, and flex development. All utilities to site. Outstanding proximity to massive commercial and multifamily growth. VA's fastest growing City in it's fastest growing commercial district. Almost 500'

  Gillian Greenfield Coldwell Banker Premier

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601
• 

  

  /16

  $450,000

  • Land
  • 77 Acres
  • $5,844 per Acre

  92 Bobcat Trail, Winchester, VA 22602

  Calling all hunters or just someone who wants seclusion! This property has amazing views and already has a structure perfect to finish your way! Perfect for getting away from it all or long hunting trips. No septic or power to structure yet. Gate to enter property. Property has 2 pink flags at the beginning of property and runs all the way to the power lines.

  Daryl Stout RE/MAX Real Estate Connections

  92 Bobcat Trail, Winchester, VA 22602

Showing Results 81 - 120, Page 3 of 9