Winchester, VA Homes for Sale under $400,000

• 

  

  /2

  $349,900 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,890 Sq Ft

  113 Christopher Dr, Winchester, VA 22601

  Meticulously maintained 3 bedroom, 1.5 bath home in a convenient in-town Winchester location! This home shows beautifully and features hardwood floors that add warmth and character throughout the main living areas. Spacious bedrooms and updates made over the years make this home functional and livable, while still providing an opportunity to personalize as desired. The partially finished basement

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 318-0527

  113 Christopher Dr, Winchester, VA 22601
• Explore Winchester

• 

  

  

  /11

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,456 Sq Ft

  1755 N Hayfield Rd, Winchester, VA 22603

  Enjoy easy one-level living in this charming all brick ranch set on just under an acre of peaceful privacy. This well-kept 3 bedroom, 1.5 bath home features beautiful wood floors throughout and a cozy wood-burning fireplace in the living room. The full, unfinished basement offers plenty of room for storage, hobbies, or future expansion. Relax outdoors on the welcoming front porch, rear porch, or

  

  Katherine (Kat) Wetzel

  Century 21 Redwood Realty

  (540) 596-5444

  1755 N Hayfield Rd, Winchester, VA 22603
• 

  

  

  /65

  $389,990

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

  317 Gray Ave, Winchester, VA 22601

  Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully

  

  Matthew Abregu

  Keller Williams Realty

  (540) 701-3590

  317 Gray Ave, Winchester, VA 22601
• 

  

  

  /32

  $379,999

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft

  151 Mccormick Cir Unit 201, Winchester, VA 22602

  Price improvement!! Experience Effortless 55+ Living at Winchester Landing – The Sapphire by Ryan Homes Discover the perfect blend of comfort and convenience in the Sapphire model, a spacious single-level condo offering over 1,500 sq. ft. of thoughtfully designed living space. The open-concept layout seamlessly connects a modern kitchen, large island, and bright great room, creating an inviting

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  (540) 787-2320

  151 Mccormick Cir Unit 201, Winchester, VA 22602
• 

  

  

  /26

  $389,990 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft

  Bedford II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

  Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Box bay rear window and 10' x 14' Trex deck. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  DRB Homes Builder

  0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
• 

  

  /37

  $399,500

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft

  1033 Sunnyside Dr, Winchester, VA 22603

  Welcome to 1033 Sunnyside Drive, a beautifully renovated bungalow tucked away on a quiet street just minutes from historic downtown Winchester. This charming home blends classic character with modern upgrades, creating a warm and inviting place to call home.Start your day on the inviting 9’ x 11’ tiled front porch, complete with new railings and stairs, the perfect spot for morning coffee or

  Tien Dao Redfin Corporation

  1033 Sunnyside Dr, Winchester, VA 22603
• 

  

  /31

  $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
• 

  

  /23

  $349,990 New Construction

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

  Northgate Plan at Hiatt Pointe at Snowden Bridge - 55+ Villas Collection, 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 Wagtail Ln Unit 36578847, Winchester, VA 22603
• 

  

  /29

  $389,000 Open Fri 4PM - 6PM

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  224 Hawk Trail, Winchester, VA 22602

  Welcome home to this charming retreat nestled in the Shawneeland community of Winchester, Virginia. This beautifully reimaged rambler has been fully remodeled. The 3-bedroom, 2-bathroom home offers the perfect blend of modern finishes and relaxed mountain community living – ready for you to move-in and enjoy! Step outside and breathe it all in. A delightful front porch sets the tone the moment

  Joelle Graham Weichert, REALTORS

  224 Hawk Trail, Winchester, VA 22602
• 

  

  /17

  $339,000

  • 3 Beds
  • 1 Bath
  • 1,699 Sq Ft

  2956 Grace St, Winchester, VA 22601

  Welcome to 2956 Grace Street — a 3-bedroom, 1-bath ranch-style home offering comfortable single-level living in Winchester, where a simple, functional layout and everyday ease come together. Inside, the home opens to a light-filled living area with hardwood floors that add warmth and character, creating a comfortable place to gather or unwind at the end of the day. The kitchen offers workspace

  Carolyn Young Samson Properties

  2956 Grace St, Winchester, VA 22601
• 

  

  /50

  $369,900

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

  109 Huron Trail, Winchester, VA 22602

  Discover this inviting 3-bedroom, 2-bath tri‐level home, offering flexible living spaces and a unique layout designed for comfort and creativity. The main level features a bright kitchen and a welcoming living room, setting the tone for easy everyday living. The upper-level hosts three full bedrooms, including a comfortable primary suite with its own ensuite bath, along with a well‐appointed full

  LESLIE WEBB Long & Foster Real Estate, Inc.

  109 Huron Trail, Winchester, VA 22602
• 

  

  /29

  $360,000

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  16 S Pleasant Valley Rd, Winchester, VA 22601

  Welcome to this one-of-a-kind property offering a unique and inviting layout designed with a seamless flow from front to back, filled with natural light throughout. Start your mornings on the rear patio enjoying peaceful sunrise views, and unwind in the evenings on the welcoming front porch with beautiful sunsets — the best of both worlds right at home.This home has been thoughtfully updated

  Vanessa Couture Samson Properties

  16 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /45

  $385,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  540 Eagle Place, Winchester, VA 22601

  Welcome to this well-maintained one-level rancher tucked away in a quiet cul-de-sac. This home offers easy, comfortable living with a warm and inviting feel throughout. Hardwood floors run through much of the home, complemented by LVP in the living and dining areas. The living room features a cozy fireplace and flows into the dining area and kitchen, where you’ll find stainless steel appliances,

  Camryn Jeremiah NextHome Realty Select

  540 Eagle Place, Winchester, VA 22601
• 

  

  /41

  $355,000

  • 2 Beds
  • 2.5 Baths
  • 1,837 Sq Ft

  132 Seabreeze Ln, Winchester, VA 22602

  Amazing, end-unit townhome tucked in the back of sought after Windstone. Enjoy your own outdoor oasis from the spacious deck with stairs, overlooking the expanded, fully fenced yard, and surrounded by wooded common area behind and on the side. The inside is wonderfully kept, having been beautifully renovated , this home is truly a show-stopper! The main floor features updated flooring and paint

  Lisa Gill ERA Oakcrest Realty, Inc.

  132 Seabreeze Ln, Winchester, VA 22602
• 

  

  /16

  $329,900

  • 3 Beds
  • 2 Baths
  • 1,147 Sq Ft

  2015 Senseny Rd, Winchester, VA 22602

  Price reduced! Renovated house with NO HOA. The lot is almost half acre, it goes beyond the metal fence on the back to the tree line. The following are new: HVAC, siding, kitchen, bathrooms. floors, gutters, washer and dryer . The roof was installed in 2018. The windows in 2015. Fenced back yard. The driveway has gravel. 4 cars can fit easily in the front, plus another car in the backyard. This

  Alex Fernandez Epic Realty, LLC.

  2015 Senseny Rd, Winchester, VA 22602
• 

  

  /63

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  520 N Braddock St, Winchester, VA 22601

  Welcome to this charming home in the heart of Winchester offering character, natural light, and a highly walkable location.This home features 3 bedrooms and 2 full bathrooms, with all bedrooms located on the upper level. At the top of the stairs you’ll find a spacious primary bedroom filled with natural light, creating a bright and inviting retreat. Large windows throughout the home allow

  Angela Duncan MarketPlace REALTY

  520 N Braddock St, Winchester, VA 22601
• 

  

  /32

  $399,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,338 Sq Ft

  3138 Eton Place, Winchester, VA 22601

  Beautiful, just like brand new, 3 bedroom 2.5 bath end unit townhome located in The Lofts at Creekside! Walking distance to local restaurants and shopping here in Creekside. Home features large kitchen island, stainless steel appliances, and luxury vinyl plank flooring, private balcony, surrounded by open floor plan which provides for great entertainment. Nice upgrades all throughout the house!

  Christopher Hild Realty FC, LLC

  3138 Eton Place, Winchester, VA 22601
• 

  

  /30

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  616 Cardinal Dr, Winchester, VA 22602

  Nestled in the serene Wilde Acres community, this exquisite split foyer home, built in 2024, offers a harmonious blend of modern luxury and inviting comfort. With three spacious bedrooms and two full bathrooms, this residence is designed for both relaxation and entertaining, making it the perfect sanctuary for those who appreciate the finer things in life. Step inside to discover a thoughtfully

  Brett Shankle Samson Properties

  616 Cardinal Dr, Winchester, VA 22602
• 

  

  /36

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  102 Stribling Way, Winchester, VA 22602

  Beautifully maintained townhome located in the convenient Winchester community known as Freedom Manor. This location is close to everything yet out of the hurly-burly. Built in 2022 this home looks and feels brand new. Come inside! The entry level features a roomy foyer, a spacious finished room that is perfect for office, a one-car garage and an unfinished bathroom space with rough-in offering

  Angela Duncan MarketPlace REALTY

  102 Stribling Way, Winchester, VA 22602
• 

  

  /43

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,405 Sq Ft

  1851 Melvor Ln, Winchester, VA 22601

  Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to

  RoxAnn Grimes RE/MAX Roots

  1851 Melvor Ln, Winchester, VA 22601
• 

  

  /36

  $314,900

  • 3 Beds
  • 1 Bath
  • 1,086 Sq Ft

  126 S Euclid Ave, Winchester, VA 22601

  This 3-bedroom, 1 full bath home is ready for you to move right in! Entire inside has been freshly painted. As you enter, you'll see the spacious living room with LVP flooring. Kitchen with new LVP flooring, new stainless-steel stove, new stainless-steel hood vent, new stainless-steel refrigerator and an eating area. Beautiful full bath with tile shower. 3 great sized bedrooms with LVP flooring.

  Matt Kilmer Samson Properties

  126 S Euclid Ave, Winchester, VA 22601
• 

  

  /3

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,505 Sq Ft

  101 Maury Way, Winchester, VA 22602

  Perfect End-Townhome at Winchester Landing with Garage/patioPrivate main level bedroom & bath, big closet and two bedrooms with bath upstairs. Kitchen walks out to back patio and landscaping is really nice.Lots of light and open space, great condition.Stainless appliances, walk-out to spacious back patio, full size washer & dryer near garage in seperate spot.Active-adult

  Anita Hartke National Realty, LLC

  101 Maury Way, Winchester, VA 22602
• 

  

  /56

  $349,900 Open Sat 2:30PM - 4:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,058 Sq Ft

  224 Doe Trail, Winchester, VA 22602

  Welcome home to this spacious 4-bedroom, 2.5-bath ranch nestled on two wooded lots in Shawneeland - which has a lake, playground, beach and more! Situated on over half an acre, this property offers privacy, beautiful natural surroundings, and an abundance of flowers and mature plantings that create a peaceful setting. Inside, you'll find finished living space on both levels, offering flexibility

  Traci Shoberg Samson Properties

  224 Doe Trail, Winchester, VA 22602
• 

  

  /26

  $305,000

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft

  110 Duwamish Trail, Winchester, VA 22602

  Charming and Move-In Ready Ranch in a Peaceful Setting!Welcome home to this beautifully refreshed single-level ranch nestled on a spacious, tree-lined lot. This inviting home features a bright and functional layout with updated finishes throughout. The kitchen offers grey cabinetry, granite countertops, and stainless steel appliances, creating a clean and modern space perfect for everyday

  Tina Jacobin Main Street Realty

  110 Duwamish Trail, Winchester, VA 22602
• 

  

  /22

  $332,900

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  105 Buckskin Trail, Winchester, VA 22602

  Nestled in the charming Shawneeland community, you will enjoy the mountain views in this delightful ranch-style home which offers a perfect blend of comfort and modern living. With a major renovation completed in 2026, this residence boasts a fresh and inviting atmosphere, ideal for creating lasting memories. The exterior features low-maintenance vinyl siding, complemented exterior lighting that

  Bruce Elsey Long & Foster Real Estate, Inc.

  105 Buckskin Trail, Winchester, VA 22602
• 

  

  /37

  $395,000

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

  116 Maury Way, Winchester, VA 22602

  Welcome home! This lovely and charming end-unit townhome is nestled in the sought-after active adult community of Winchester Landing. Why wait for the builders when you can have a better than new home right now?! Perfectly located on the east side of Winchester, everything you need is conveniently close by; shopping, restaurants, amenities, and all the commuter routes. This spacious home is

  Amanda White Nova Home Hunters Realty

  116 Maury Way, Winchester, VA 22602
• 

  

  /51

  $304,900

  • 2 Beds
  • 3.5 Baths
  • 1,740 Sq Ft

  218 Tudor Dr, Winchester, VA 22603

  OPTIONAL THIRD BEDROOM! Welcome home to this beautifully updated townhome tucked away in a private, peaceful neighborhood—yet just minutes from major commuter routes, everyday amenities, and only 5 minutes to downtown Winchester! This bright and inviting home features fresh paint throughout, brand-new carpet, updated outlets, switches, lighting, and two new toilets—making it truly move-in ready.

  Stephanie Feltner Realty ONE Group Old Towne

  218 Tudor Dr, Winchester, VA 22603
• 

  

  /47

  $311,000

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

  151 Mccormick Cir Unit 203, Winchester, VA 22602

  Welcome to Winchester Landing, a 55+ condominium community offering comfort, convenience, and low-maintenance living. This secured building provides added peace of mind for residents. This well-designed 2-bedroom, 2-bath condo features a combination kitchen and dining area that opens to a spacious family room—perfect for everyday living. The primary suite features a walk-in shower and ample

  RoxAnn Grimes RE/MAX Roots

  151 Mccormick Cir Unit 203, Winchester, VA 22602
• 

  

  /58

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,585 Sq Ft

  139 Bryarly Rd, Winchester, VA 22603

  Motivated seller!! Seller is moving out of state. Welcome home to timeless charm with this beautiful 3-bedroom, 2–full-bath home, featuring stunning original woodwork that has been exceptionally well preserved. From the moment you enter, you’ll appreciate the character and craftsmanship that make this home truly special. While leaving the character of the home, it has been well cared for. New

  Hailey Mooney Real Broker, LLC

  139 Bryarly Rd, Winchester, VA 22603
• 

  

  /40

  $358,000

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft

  323 Russelcroft Rd, Winchester, VA 22601

  Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living space. Beautiful cared for by the homeowners. 3 bedrooms 2 full baths detached home.Beautiful Detached home with 3 bedrooms and 2 full baths + bonus room on the basement isfull finished with a family room. Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living

  Alexandra Brown Spring Hill Real Estate, LLC.

  323 Russelcroft Rd, Winchester, VA 22601
• 

  

  /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
• 

  

  /32

  $364,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,590 Sq Ft

  203 Crestwood Ln, Winchester, VA 22602

  Property is back on the market due to buyer’s home sale contingency not being satisfied—no fault of the seller.Welcome home to this well-maintained property located in an established Winchester neighborhood. The property features a functional main-level layout with a bright living area and a sunroom that adds additional usable space. Recent updates include a roof installed around 5 years ago,

  Jen Richards MarketPlace REALTY

  203 Crestwood Ln, Winchester, VA 22602
• 

  

  /20

  $319,000

  • 1,362 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  Don't miss taking a LOOK at this property with the new low price of $319K. One Way street = quiet Gorgeous Rehab - you have to see it! Secure Parking off the alley Efficient HVAC mini splits installed Washer and Dryer included

  Teri Domanski Corcoran McEnearney

  553 Highland Ave, Winchester, VA 22601
• 

  

  /22

  $335,000

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

  1004 S Cameron St, Winchester, VA 22601

  Renovated 3-bedroom detached home for just $335,000!- -Tucked away on a private 7,840 sq. ft. lot in Winchester. This charming single home gives you the one thing that condos and townhouses can’t; freedom. No shared walls, no stairs, and absolutely no HOA telling you what color your door can be.- -Step inside and you’ll instantly feel it, the calm of a bright,

  Patricia Salgado Metas Realty Group, LLC

  1004 S Cameron St, Winchester, VA 22601
• 

  

  /82

  $370,000

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  2431 Cedar Creek Grade, Winchester, VA 22602

  This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in place.

  Edward Beightol Cedar Creek Real Estate

  2431 Cedar Creek Grade, Winchester, VA 22602
• 

  

  /12

  $369,900

  • Land
  • 11.49 Acres
  • $32,193 per Acre

  Lot 1 Tavistock Dr, Winchester, VA 22602

  Beautiful 11.49 acre Lot, approved for 3 bedroom perk, Tavistock Estates one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

  Gillian Greenfield Coldwell Banker Premier

  Lot 1 Tavistock Dr, Winchester, VA 22602
• 

  

  /14

  $359,990 New Construction

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

  119 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

  119 Castaway Place, Winchester, VA 22603
• 

  

  /16

  $379,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  106 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

  106 Heirloom Way, Winchester, VA 22603
• 

  

  /17

  $374,990 New Construction

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

  115 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

  115 Castaway Place, Winchester, VA 22603
• 

  

  /17

  $349,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  119 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

  119 Heirloom Way, Winchester, VA 22603

Showing Results 1 - 40, Page 1 of 2