Winchester, VA Homes for Sale under $400,000

• 

  

  

  /26

  $359,000

  New Construction $14K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  600 Winchester Dr, Winchester, VA 22602

  Blue Ocean Modulars introduces The Laurel, a three-bedroom, two-full-bath ranch home to be built in the Wilde Acres subdivision of Frederick County. Nestled against a forested backdrop and built with high-quality workmanship, this residence showcases modern construction designed for durability, comfort, and long-term value. The home features Insul-Stud framing, a cutting-edge system that enhances

  Rebecca McTavish Long & Foster Real Estate, Inc.

  600 Winchester Dr, Winchester, VA 22602
• 

  

  

  /26

  $364,990

  New Construction $3K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  11 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Lower Level Bathroom! This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free

  DRB Homes Builder

  11 Monteith Dr, Winchester, VA 22601
• 

  

  

  /35

  $350,000

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  302 Pheasant Dr, Winchester, VA 22602

  NEW CONSTRUCTION — PRICED TO SELL AT $350,000! If you’ve been waiting for new construction that offers more than just fresh finishes, 302 Pheasant Drive deserves a look. Built by a local builder with more than 20 years of experience, this 3-bedroom, 2-bath ranch combines quality craftsmanship, one-level living, and a full walkout basement that gives you room to grow.The main level offers

  Tyler Hazelwood Virginia Real Estate

  302 Pheasant Dr, Winchester, VA 22602
• 

  

  

  /33

  $300,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018.

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
• 

  

  

  /42

  $400,000

  • 3 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  116 Cloverdale Ct, Winchester, VA 22602

  Located in the Brentwood Terrace Subdivision Near Greenwood Drive & Valley Mill Rd This Spectacular Three Level 3 Bedroom 2.5 Bathroom Single Family Home is Situated on a Beautifully Manicured Private Cul-De-Sac Lot Surrounded by Trees, Inviting Front Porch, Fenced-In Back Yard, Deck, & Newly Paved Driveway! The Sellers Pride of Ownership Includes 2 Brand New Upgraded Dual HVAC Systems (2026),

  Bill Fritz RE/MAX Executives

  116 Cloverdale Ct, Winchester, VA 22602
• 

  

  /36

  $397,990

  New Construction

  • 3 Beds
  • 2.5 - 3.5 Baths
  • 1,966+ Sq Ft

  St Paul Plan at Winchester Ridge Townhomes, 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 Builder

  161 Williamson Rd Unit 37409245, Winchester, VA 22602
• 

  

  /21

  $210,000

  • Land
  • 5 Acres
  • $42,000 per Acre

  0 Off of Mount Olive Rd Unit VAFV2044302, Winchester, VA 22603

  Prime building lot conveniently located less than 10 minutes west of Winchester with immediate access to US-50 - Northwestern Pike. Part of what was once the well known Rotz Farm and now part of the brand new Ridgeview Glen community. This land is ideally positioned between scenic Flint Ridge and flowing Hogue Creek. This tract features a 4 bedroom septic certification letter which is already on

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Off of Mount Olive Rd Unit VAFV2044302, Winchester, VA 22603
• 

  

  /29

  $369,999

  • 3 Beds
  • 2.5 Baths
  • 1,630 Sq Ft

  120 Maury Way, Winchester, VA 22602

  Welcome to this beautifully upgraded townhome in the highly sought-after Winchester Landing active adult community! Built in 2023, this move-in-ready home offers the perfect blend of modern style, comfort, and convenience. Designed with true main-level living in mind, the spacious first floor features a desirable primary suite, full bath, and laundry room, making everyday living effortless. The

  Samiirah Ruhomutally Pearson Smith Realty, LLC

  120 Maury Way, Winchester, VA 22602
• 

  

  /17

  $199,900

  $15K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $555,278 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
• 

  

  /36

  $355,500

  $4K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,644 Sq Ft

  423 Panther Dr, Winchester, VA 22602

  Welcome to 423 Panther Dr in Winchester, VA! This spacious split-level home offers 4 bedrooms, 3 full bathrooms, a 2-car front-entry garage, gravel driveway, and a storage shed, all situated in a convenient and peaceful setting.The upper level features 3 bedrooms and 2 full bathrooms. The kitchen and living areas showcase beautiful hardwood flooring, with new carpet throughout the

  Caleb Fowler Samson Properties

  423 Panther Dr, Winchester, VA 22602
• 

  

  /15

  $375,990

  New Construction $16K PRICE DROP

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

  105 Heirloom Way, 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

  105 Heirloom Way, Winchester, VA 22603
• 

  

  /42

  $175,000

  • 1 Bed
  • 1 Bath
  • 384 Sq Ft

  305 Raccoon Dr, Winchester, VA 22602

  Cozy 1-bedroom, 1-bathroom cabin located on a level, nicely shaded lot, ready for your enjoyment. Offering the perfect combination of rustic character, comfort, and natural beauty. Step outside onto the screened-in porch and enjoy your morning coffee, unwind with a good book, or simply take in the sights and sounds of the surrounding woods. This peaceful setting offers a wonderful opportunity to

  Bill Dixon Dandridge Realty Group, LLC

  305 Raccoon Dr, Winchester, VA 22602
• 

  

  /22

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  452 Valley Mill Rd, Winchester, VA 22602

  SOLD AS IS, CASH ONLY! Investor special on this great home that is on .55 Acre lot (2 lots make this up). Outbuildings, wood floors, fireplace, 3 generous size bedrooms, laundry room, eat in kitchen and dining room. Home needs to be hooked up to county water, current well not working properly. Call for details.

  Deborah Matthews ERA Oakcrest Realty, Inc.

  452 Valley Mill Rd, Winchester, VA 22602
• 

  

  /17

  $385,690

  New Construction

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

  660 Arden Ct, Winchester, VA 22601

  660 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  660 Arden Ct, Winchester, VA 22601
• 

  

  /18

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  132 Geronimo Trail, Winchester, VA 22602

  Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet and highly desirable neighborhood, this charming single-family home is perfect for first-time buyers, downsizers, or anyone seeking a peaceful retreat. This 1,232 square-foot rancher features 3 bedrooms, 2 full bathrooms, eat-in kitchen, living room, a brick fireplace with highly a efficient wood-burning

  Shane Price Long & Foster Real Estate, Inc.

  132 Geronimo Trail, Winchester, VA 22602
• 

  /2

  $139,900

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  130 Wollaston Dr Unit A34, Winchester, VA 22603

  COMING SOON! Currently under construction. Welcome to Regency Lakes, an all age active and vibrant community, where your dream home is coming to life. We are excited to offer a brand new, 2026 3 bed, 2 bath home for sale, featuring approximately 1564.80 sq ft of thoughtfully designed living space. Located in Winchester, this soon-to-be-completed property will offer the perfect blend of modern

  Kristina Kelly Regency Lakes

  130 Wollaston Dr Unit A34, Winchester, VA 22603
• 

  

  /28

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
• 

  

  /11

  $189,900

  • Land
  • 5 Acres
  • $37,980 per Acre

  0 0 Perry Rd, Winchester, VA 22602

  10 min or less into Winchester City, discover the possibilities on this beautiful 5-acre parcel, offering a peaceful mix of mature woods, open clearing areas, a creek, and a small pond that sits partially on the property. With 4-bedroom septic approval and no restrictions, this property provides the flexibility to create a private country retreat, recreational getaway, or secluded

  Lorie Crabill Sager Real Estate

  0 0 Perry Rd, Winchester, VA 22602
• 

  

  /10

  $399,000

  • Land
  • 3,920 Sq Ft
  • $4,433,333 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
• 

  

  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  540 Bellview Ave, Winchester, VA 22601

  Attention investors! Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
• 

  /2

  $250,000

  • Land
  • 5 Acres
  • $50,000 per Acre

  341 Laurel Grove Rd, Winchester, VA 22602

  THERE ARE 2 -5 ACRE BUILDING LOTS W/4 BR CONVENTIONAL PERKS APPROVED. LOT 3 IS UP ON THE HILL AND LOT 4 FRONTS THE ROAD. THESE LOTS ARE CREATED FROM A LARGER PARCEL BY WAY OF A BOUNDRY LINE ADJUSTMENT. NEW PLATS AND BOUNDRY LINE ADJUSTMENTS INCLUDED IN DOCUMENTS. NEW DEEDS WILL BE ISSUED AT CLOSING. TAX ASSESSMENTS AND TAXES ARE BASED ON THE ENTIRE PROPERTY PRIOR TO BOUNDRY LINE ADJUSTMENT. NEW

  Barbara Singhas Crum Realty, Inc.

  341 Laurel Grove Rd, Winchester, VA 22602
• 

  

  /46

  $360,000

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,362 Sq Ft

  300 Elk Trail, Winchester, VA 22602

  Looking for a newer home with room to spread out and a peaceful wooded setting? Welcome to 300 Elk Trail.Built in 2021 and tucked among the trees in the Mountain Falls/Wilde Acres area, this 4-bedroom, 3-bath home offers the perfect blend of modern convenience and country living. The open main level creates a welcoming space for gathering with family and friends, while the finished lower

  Abby Walters Preslee Real Estate

  300 Elk Trail, Winchester, VA 22602
• 

  

  /78

  $260,000

  • 2 Beds
  • 1.5 Baths
  • 1,068 Sq Ft

  103 E Germain St, Winchester, VA 22601

  Roof replaced in 2020.Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a

  RoxAnn Grimes RE/MAX Roots

  103 E Germain St, Winchester, VA 22601
• 

  

  /11

  $340,000

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

  197 Denny Ln, Winchester, VA 22603

  Charming 3-bedroom, 2-bathroom cottage located off Berryville Ave. This inviting home features a large fully fenced back yard complete with a firepit, perfect for outdoor gatherings and relaxation.On the main level, you'll find two cozy bedrooms, kitchen with stainless appliances and a living room with shiplap accent wall. Upstairs, the spacious primary suite awaits, boasting a large dual

  Stephanie Ambrogi Realty ONE Group Old Towne

  197 Denny Ln, Winchester, VA 22603
• 

  

  /26

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,844 Sq Ft

  1310 Whittier Ave, Winchester, VA 22601

  Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a

  Sarah Hott Realty ONE Group Old Towne

  1310 Whittier Ave, Winchester, VA 22601
• 

  

  /32

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft

  204 Cochise Trail, Winchester, VA 22602

  Adorable rancher in Shawneeland with access to a lake, trails, beach, and fishing. Ideally you wish for spacious living quarters,3 bedrooms, 2 full baths, and a walkout basement with a finished room for gym/office/den..well we have all that and more so come take a gander and make it your own before the summer ends.

  Dave Spence RE/MAX Roots

  204 Cochise Trail, Winchester, VA 22602
• 

  

  /64

  $359,000

  $16K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,474 Sq Ft

  805 Pennsylvania Ave, Winchester, VA 22601

  Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect

  Sherry Santmyer Hunt Country Sotheby's International Realty

  805 Pennsylvania Ave, Winchester, VA 22601
• 

  

  /45

  $315,000

  $35K PRICE DROP

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

  913 Orchard Hill Dr, Winchester, VA 22601

  New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter

  Dallas Croft Samson Properties

  913 Orchard Hill Dr, Winchester, VA 22601
• 

  

  /31

  $384,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft

  103 Elaine Dr, Winchester, VA 22602

  This is the one you’ve been waiting for — a beautifully maintained ranch‑style home with thoughtful updates and a bright, comfortable layout throughout. A newer roof, updated HVAC, and fresh carpet provide peace of mind and move‑in readiness from day one.The primary ensuite serves as a true retreat, featuring a spa‑like bath and a walk‑in closet. Two additional bedrooms offer flexible living

  LESLIE WEBB Long & Foster Real Estate, Inc.

  103 Elaine Dr, Winchester, VA 22602
• 

  /2

  $199,900

  • Land
  • 6,969 Sq Ft
  • $1,249,375 per Acre

  1415 Ramseur Ln, Winchester, VA 22601

  Steve DuBrueler Coldwell Banker Premier

  1415 Ramseur Ln, Winchester, VA 22601
• 

  

  /37

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  163 Margaret Ln, Winchester, VA 22603

  (Magnificent Margaret) This home has a lot to offer: All bedrooms and bathrooms on the main level, fully updated kitchen with Stainless Steel Appliances (Fridge, Dishwasher, Stove, Microwave) Quartz counter top, built in pantry, remodeled bathrooms with a double vanity in the primary bathroom and a walk-in tile shower, Central Heating & Air, New windows, Laundry room, large driveway, two car

  Michael Sprague Samson Properties

  163 Margaret Ln, Winchester, VA 22603
• 

  

  /27

  $339,999

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  113 Windmill Ln, Winchester, VA 22602

  Why rent when you can own? This spacious townhome has everything you are looking for. Located steps away from Route 7 & I Interstate 81, with grocery stores, pharmacy and restaurants. Who needs to go out when you can entertain at home. LARGE rooms, well equipped Kitchen w/ walk-in Pantry & Island, Microwave & Glass Top cooking Range & durable easy to clean Corian Countertops. Kitchen flows to

  Sarah Hott Realty ONE Group Old Towne

  113 Windmill Ln, Winchester, VA 22602
• 

  

  /71

  $339,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft

  904 Archwood Trail, Winchester, VA 22602

  "Escape To Archwood" Whether you're looking for a weekend retreat or a primary residence this 3-bedroom, 2-bathroom Chalet Style home is it! With incredible mountain views, privacy and room to stretch out this home can be your happy place! Open concept on the upper level with vaulted ceilings and a large kitchen with stainless steel appliances. Primary bedroom with a sliding door to the deck and

  Matt Kilmer Samson Properties

  904 Archwood Trail, Winchester, VA 22602
• 

  /2

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  111 Haven Terrace, Winchester, VA 22602

  Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This single-level home offers a practical layout with comfortable living spaces and plenty of potential to make it your own.The main-level living design provides easy access throughout the home, making this property a great fit

  Erin Kavanagh EXP Realty, LLC

  111 Haven Terrace, Winchester, VA 22602
• 

  

  /45

  $260,000

  • 2 Beds
  • 1 Bath
  • 997 Sq Ft

  108 Martin Dr, Winchester, VA 22602

  Attention investors! Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large

  Heloisa Amar Samson Properties

  108 Martin Dr, Winchester, VA 22602
• 

  

  /63

  $330,000

  • 4 Beds
  • 2 Baths
  • 1,592 Sq Ft

  805 S Kent St, Winchester, VA 22601

  Very well-maintained 2-level home offering 4 bedrooms and 2 full baths in the heart of Winchester. This home features a functional layout with a blend of classic charm and thoughtful updates throughout. Pride of ownership shows inside and out, with comfortable living spaces, a fully fenced yard, and a private driveway for off-street parking. Conveniently located near downtown, shopping, and

  Carolina Mosquera Weichert, REALTORS

  805 S Kent St, Winchester, VA 22601
• 

  

  /17

  $289,000

  $6K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1314 S Braddock St, Winchester, VA 22601

  1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room

  Jacqueline Moore Open Door Brokerage, LLC

  1314 S Braddock St, Winchester, VA 22601
• 

  

  /38

  $329,000

  Open Sun 12PM - 3PM $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,667 Sq Ft

  204 Cougar Trail, Winchester, VA 22602

  Nestled in the serene Wilde Acres subdivision, this charming split foyer home, built in 2020, offers a perfect blend of modern comfort and natural beauty. With 3 spacious bedrooms and 2.5 bathrooms, this residence is designed for both relaxation and entertaining. Step inside to discover a warm and inviting interior featuring laminated flooring throughout. The heart of the home is the combination

  Gerald Owens Realty ONE Group Old Towne

  204 Cougar Trail, Winchester, VA 22602
• 

  

  /32

  $329,900

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft

  103 Trade Wind Ln, Winchester, VA 22602

  Welcome home to 103 Trade Wind Lane, a beautifully updated townhome offering low-maintenance living on Winchester’s desirable east side! Perfectly situated near top schools, shopping, dining, and major commuter routes, this turn-key residence delivers both comfort and ultimate convenience. Natural light pours into the bright living room, where modern flooring lead you straight into the open

  Dan Whitacre Colony Realty

  103 Trade Wind Ln, Winchester, VA 22602

Showing Results 41 - 80, Page 2 of 5