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Browse All Winchester VA Between $400K - $500K Properties for Sale

109 Julee Dr, Winchester image
109 Julee Dr, Winchester $479,900

This lovingly maintained two-owner Colonial has been thoughtfully cared for and improved since 1994, offering the character of an established home with many of the update...

  • 4 Beds
  • 3 Baths
  • Mill Race Estates SubDv.
  • 22602 Zip Code
  • COMING SOON Status
991 Front Royal Pike, Winchester image
991 Front Royal Pike, Winchester $459,900

Enjoy easy one-level living in this well-maintained ranch home conveniently located in Winchester, close to commuter routes, shopping, restaurants, and everyday amenities...

  • 3 Beds
  • 2 Baths
  • Bufflick Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
322 E Piccadilly, Winchester image
322 E Piccadilly, Winchester $409,000

Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless ch...

  • 4 Beds
  • 1 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
131 Country Club Cir, Winchester image
131 Country Club Cir, Winchester $435,000

No HOA in the heart of Winchester! This charming brick rancher features three bedrooms, two baths, tall ceilings, fresh paint, hardwood floors, and a fireplace on the ma...

  • 3 Beds
  • 2 Baths
  • A Melvin Lewis SubDv.
  • 22602 Zip Code
  • COMING SOON Status
300 Pembridge Dr, Winchester image
300 Pembridge Dr, Winchester $439,000

Welcome to this newly renovated and thoughtfully designed 5-bedroom, 3-full-bath home offering exceptional flexibility for modern living or rental income. Featuring two ...

  • 5 Beds
  • 3 Baths
  • Pembridge Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
310 Goldenrod Rd, Winchester image
310 Goldenrod Rd, Winchester $430,000

This is the one you have been waiting for!! Well cared for home, one story living in desirable Briarwood Estates...east side location convenient to commuter routes, shopp...

  • 3 Beds
  • 2 Baths
  • Briarwood Estates SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1412 S Loudoun St, Winchester image
1412 S Loudoun St, Winchester $429,000

Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
1960 Siler Rd, Winchester image
1960 Siler Rd, Winchester $499,900

Looking for one-level living with acreage, a detached workshop/garage, RV/camper parking, and no HOA? Welcome to 1960 Siler Road, a custom-built ranch situated on 5 fence...

  • 3 Beds
  • 2 Baths
  • None Available SubDv.
  • 22603 Zip Code
  • ACTIVE Status
142 Sequoia Dr, Winchester image
142 Sequoia Dr, Winchester $434,900 ▼

The lot you’ve been waiting for—without giving up the convenience of townhouse living! This exceptional end-unit townhome sits on a rare, double-sized lot, offering the k...

  • 3 Beds
  • 4 Baths
  • Fieldstone SubDv.
  • 22602 Zip Code
  • ACTIVE Status
109 Marlow Ct, Winchester image
109 Marlow Ct, Winchester $420,000

Don't miss this nearly new townhouse in Rossum Crossing! With 4 bedrooms, 3.5 bathrooms, over 2,000 square feet of finished space, and a one-car garage, this home offers ...

  • 4 Beds
  • 4 Baths
  • Rossum Crossing SubDv.
  • 22602 Zip Code
  • ACTIVE Status
938 Wayne Dr, Winchester image
938 Wayne Dr, Winchester $499,900

Beautifully maintained and updated home located in popular area close to Medical Center, schools , services and amenities and with easy access to commuter thoroughfares. ...

  • 4 Beds
  • 3 Baths
  • Meadow Branch South SubDv.
  • 22601 Zip Code
  • PENDING Status
109 Keswick Ct, Winchester image
109 Keswick Ct, Winchester $439,000

Some homes have a screened porch. This one has a screened porch you may never want to leave. You could sit on your front porch and enjoy a rain shower, but you might be h...

  • 3 Beds
  • 2 Baths
  • Pembridge Heights SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1019 Berryville Ave, Winchester image
1019 Berryville Ave, Winchester $499,000

1019 Berryville Ave, Winchester, VA 22601 | Prime Winchester location! This approximately 3,000+ square foot finished property offers flexibility, with three full, indep...

  • 22601 Zip Code
  • ACTIVE Status
4531 Back Mountain Rd, Winchester image
4531 Back Mountain Rd, Winchester $498,500

HUNTER’S PARADISE • 13.58 UNRESTRICTED ACRES!! Privacy, wildlife, outdoor adventure, and plenty of space—this home offers a rare opportunity to enjoy the peace and privac...

  • 4 Beds
  • 2 Baths
  • None Available SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
114 Meadow Way, Winchester image
114 Meadow Way, Winchester $439,000

Discover the perfect blend of modern living and community charm in this stunning Colonial-style home located in the desirable High View Manor subdivision. Built in 2021, ...

  • 3 Beds
  • 3 Baths
  • High View Manor SubDv.
  • 22602 Zip Code
  • ACTIVE Status
640 Arden Ct, Winchester image
640 Arden Ct, Winchester $410,190

640 Arden Court is an attractive new 3 level end townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Ad...

  • 4 Beds
  • 4 Baths
  • Abrams Crossing SubDv.
  • 22601 Zip Code
  • PENDING Status
422 S Loudoun St, Winchester image
422 S Loudoun St, Winchester $434,000

Priced at recent appraised value. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the cha...

  • 3 Beds
  • 3 Baths
  • City Of Winchester SubDv.
  • 22601 Zip Code
  • ACTIVE Status
100 Keystone Ln Unit #HOMESITE 1090, Winchester image
100 Keystone Ln Unit #HOMESITE 1090, Winchester $456,639 ▲

Discover a new MOVE-IN READY and thoughtfully designed home for active 55+ living. This BRAND NEW END VILLA gives you more time to enjoy what matters most. Main-level liv...

  • 3 Beds
  • 3 Baths
  • Hiatt Pointe At Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
424 Valley Mill Rd, Winchester image
424 Valley Mill Rd, Winchester $474,900 ▼

Welcome to this beautifully updated Colonial in Winchester, where classic curb appeal meets thoughtful modern upgrades. The exterior shines with new Hardie Plank siding, ...

  • 4 Beds
  • 3 Baths
  • Brentwood Terrace SubDv.
  • 22602 Zip Code
  • ACTIVE Status
3135 Eton Pl, Winchester image
3135 Eton Pl, Winchester $400,000

Lofts at Creekside is one of the newest walkable communities in the city of Winchester with proximity to the upscale Creekside Station. Offering eateries, clothing store...

  • 3 Beds
  • 3 Baths
  • Lofts At Creekside SubDv.
  • 22601 Zip Code
  • ACTIVE Status
102 Primrose Pl, Winchester image
102 Primrose Pl, Winchester $499,900

Nestled in the charming Apple Ridge community, this delightful Colonial home offers a perfect blend of comfort and convenience. With 2,528 sq. ft. of living space, this r...

  • 5 Beds
  • 3 Baths
  • Apple Ridge SubDv.
  • 22602 Zip Code
  • ACTIVE Status
2643 Middle Rd, Winchester image
2643 Middle Rd, Winchester $499,999

Location, Location, Location! NO HOA!!! Priced below assessed value! Hardwood floors on the main level. Formal living and dining room leads to the Family room with sto...

  • 4 Beds
  • 4 Baths
  • None Available SubDv.
  • 22601 Zip Code
  • ACTIVE Status
176 Lauck Dr, Winchester image
176 Lauck Dr, Winchester $435,000 ▼

Very well taken care of 3 bedrooms , 2.5 Baths in popular and Convenient STAR FORT subdivision. 5 minutes from downtown just off of Rt 522N but without any traffic nois...

  • 3 Beds
  • 3 Baths
  • Star Fort SubDv.
  • 22603 Zip Code
  • ACTIVE Status
110 Coriander Dr, Winchester image
110 Coriander Dr, Winchester $424,990 ▼

BUILDER OFFERING BELOW MARKET RATE FINANCING OPTIONS ON THIS QUICK MOVE IN HOME!! Brand-New Dual Primary Townhome—Late Summer Move-In! Step into modern living with this b...

  • 3 Beds
  • 4 Baths
  • Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
144 Solara Dr, Winchester image
144 Solara Dr, Winchester $429,900 ▼

A Rare Gem in an Unbeatable Location! Back on market to no fault of the seller or this gorgeous home. Why wait for new construction when you can have a home that is alrea...

  • 3 Beds
  • 4 Baths
  • Fieldstone SubDv.
  • 22602 Zip Code
  • ACTIVE Status
102 Zinnia Ln, Winchester image
102 Zinnia Ln, Winchester $474,990

Move right into the effortless lifestyle you've been dreaming of with this beautifully designed single-level semi-attached home, ready for immediate move-in. The open-con...

  • 2 Beds
  • 2 Baths
  • Hiatt Pointe At Snowden Bridge SubDv.
  • 22603 Zip Code
  • PENDING Status
501 Fox Dr, Winchester image
501 Fox Dr, Winchester $450,000

Welcome to this beautifully updated 4 bedroom, 2 full bath home in the heart of Winchester City! This move in-ready property offers fresh paint throughout, newly installe...

  • 4 Beds
  • 2 Baths
  • Walker Mcc Bond SubDv.
  • 22601 Zip Code
  • ACTIVE Status
413 Superior Ave, Winchester image
413 Superior Ave, Winchester $425,000 ▼

This beautiful rancher sits on 0.38 acres with an expansive, level backyard that is fully fenced and shaded by gorgeous mature trees. A large deck spans the back of the h...

  • 3 Beds
  • 2 Baths
  • Wea-Villa SubDv.
  • 22601 Zip Code
  • ACTIVE Status
307 Canyon Rd, Winchester image
307 Canyon Rd, Winchester $499,000

Welcome to 307 Canyon Road in Winchesters sought-after Senseny Glen community. This move-in-ready ranch style home offers open-concept main-level living boasting hardwoo...

  • 4 Beds
  • 2 Baths
  • Senseny Glen SubDv.
  • 22602 Zip Code
  • ACTIVE Status
102 Geneva Pl, Winchester image
102 Geneva Pl, Winchester $405,000 ▼

Location Location Location, Nice home tucked away in a cul-de-sac, this ranch style home offers 4 bedrooms and 2 full bathrooms. Eat in kitchen that has room for a tab...

  • 4 Beds
  • 2 Baths
  • Regency Heights SubDv.
  • 22603 Zip Code
  • ACTIVE Status
114 Windcrest Cir, Winchester image
114 Windcrest Cir, Winchester $435,000

Charming cape cod, located on a quiet cul-de-sac street with no through traffic! Beautiful hardwood floors welcome you into this thoughtfully updated, move-in-ready home....

  • 4 Beds
  • 3 Baths
  • Brentwood Terrace SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
116 Cloverdale Ct, Winchester image
116 Cloverdale Ct, Winchester $400,000

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...

  • 3 Beds
  • 3 Baths
  • Brentwood Terrace SubDv.
  • 22602 Zip Code
  • ACTIVE Status
116 Charlton Rd, Winchester image
116 Charlton Rd, Winchester $400,000

***Listing Agent Will be Hosting an Open House to the Public on Saturday 8-15-2026 from 1-4PM*** Conveniently Located Near Major Commuter Routes, Schools & Shopping Cente...

  • 4 Beds
  • 2 Baths
  • Carlisle Heights SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
153 Fox Dr, Winchester image
153 Fox Dr, Winchester $439,900

Welcome home to this beautifully maintained 3-bedroom, 2-bath home offering comfort, convenience, and exceptional outdoor living. Ideally located just minutes from shopp...

  • 3 Beds
  • 2 Baths
  • B P Myers SubDv.
  • 22601 Zip Code
  • ACTIVE Status
169 Sioux Loop, Winchester image
169 Sioux Loop, Winchester $402,160

Move into your new home this October and enjoy the best of fall in this stunning Adams end-unit townhome! Featuring a classic white siding exterior and bright, timeless w...

  • 4 Beds
  • 4 Baths
  • Retreat At Winding Creek SubDv.
  • 22602 Zip Code
  • ACTIVE Status
179 Sioux Loop, Winchester image
179 Sioux Loop, Winchester $404,160

Move into your new home this September/October and enjoy a fresh start this fall in the beautiful Adams end-unit townhome! Featuring a stylish green exterior and designer...

  • 4 Beds
  • 4 Baths
  • Retreat At Winding Creek SubDv.
  • 22602 Zip Code
  • PENDING Status
1853 Rosser Ln, Winchester image
1853 Rosser Ln, Winchester $400,000

Welcome to easy one-level living in Willow Lawn Cottages, a popular 55+ community in Winchester! This well-maintained home has been freshly painted and offers 2 bedrooms ...

  • 2 Beds
  • 2 Baths
  • Willow Lawn Cottages SubDv.
  • 22601 Zip Code
  • ACTIVE Status
131 Amberfield Ct, Winchester image
131 Amberfield Ct, Winchester $465,000

Move-In Ready Luxury in an Intimate 55+ Boutique Community! Crafted in 2022, this exquisite Craftsman-style residence combines main-level luxury with low-maintenance livi...

  • 2 Beds
  • 2 Baths
  • Abram's Chase SubDv.
  • 22602 Zip Code
  • PENDING Status
144 Morning Glory, Winchester image
144 Morning Glory, Winchester $499,000 ▼

Nestled in the charming Apple Ridge community, this stunning Colonial-style home offers a perfect blend of comfort and elegance. Set on a generous 0.4-acre lot, the prope...

  • 5 Beds
  • 4 Baths
  • Apple Ridge SubDv.
  • 22602 Zip Code
  • ACTIVE Status
1310 Whittier Ave, Winchester image
1310 Whittier Ave, Winchester $400,000 ▼

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 w...

  • 4 Beds
  • 2 Baths
  • Northwestern Hills SubDv.
  • 22601 Zip Code
  • ACTIVE Status
132 Swansong Pl, Winchester image
132 Swansong Pl, Winchester $404,990 ▼

BUILDER OFFERING BELOW MARKET RATE FINANCING OPTION ON THIS QUICK MOVE IN HOME!! Brand-New 4-Bedroom Townhome | Late Summer Move-In! Enjoy stylish, low-maintenance living...

  • 4 Beds
  • 4 Baths
  • Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
107 Lawford Way, Winchester image
107 Lawford Way, Winchester $459,990 ▼

Under construction for late summer Move-In and Backing to Trees! This beautifully designed home offers easy, open-concept living with a stylish gourmet kitchen featuring ...

  • 2 Beds
  • 2 Baths
  • Hiatt Pointe At Snowden Bridge SubDv.
  • 22603 Zip Code
  • ACTIVE Status
420 W Cork St, Winchester image
420 W Cork St, Winchester $449,000

Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting...

  • 4 Beds
  • 2 Baths
  • Carter & Glaize SubDv.
  • 22601 Zip Code
  • ACTIVE Status
231 Bentley Ave, Winchester image
231 Bentley Ave, Winchester $489,900

Welcome to this beautifully refreshed 3-bedroom, 2-bath rancher in Chapel Hill. After hearing buyer feedback that the home felt dated, the sellers invested thousands of d...

  • 3 Beds
  • 2 Baths
  • Chapel Hill SubDv.
  • 22602 Zip Code
  • PENDING Status
167 Manor Dr, Winchester image
167 Manor Dr, Winchester $489,900

Welcome to this beautiful new construction home offering over 2300 square feet of living space, This spacious home features 4 bedrooms, 2 1/2 bathrooms, and an attached g...

  • 4 Beds
  • 3 Baths
  • High View Manor SubDv.
  • 22602 Zip Code
  • PENDING Status
180 Quaker Ln, Winchester image
180 Quaker Ln, Winchester $439,000

Welcome to 180 Quaker Lane, where timeless charm meets thoughtful updates! Nestled on a peaceful one-acre lot in the desirable Glenside subdivision, this beautifully main...

  • 3 Beds
  • 2 Baths
  • Glenside SubDv.
  • 22603 Zip Code
  • ACTIVE UNDER CONTRACT Status
1826 Kershaw Ln, Winchester image
1826 Kershaw Ln, Winchester $400,000 ▼

Welcome to 1826 Kershaw Lane in Willow Lawn Cottages, one of Winchester, Virginia's most sought-after 55+ active adult communities, offering low-maintenance, single-level...

  • 2 Beds
  • 2 Baths
  • Willow Lawn Cottages SubDv.
  • 22601 Zip Code
  • ACTIVE Status
145 Wilkins Dr, Winchester image
145 Wilkins Dr, Winchester $405,000 ▼

PRICE DROP! ✨ Rare Opportunity on Winchester's East Side with a LOWER-LEVEL IN-LAW SUITE! 🏡NEW ROOF (2026) AND NEW BOILER (2025) Welcome home to this spacious 4-bedroom...

  • 4 Beds
  • 2 Baths
  • Green Acres SubDv.
  • 22602 Zip Code
  • ACTIVE UNDER CONTRACT Status
108 Morgan St, Winchester image
108 Morgan St, Winchester $495,000 ▼

OPEN HOUSE 08/30/2026 FROM 1:00 PM - 3:00 PM Welcome to this charming historic home in Old Town Winchester. This spacious 3-bedroom Colonial blends timeless character wi...

  • 3 Beds
  • 2 Baths
  • Winchester Historic District SubDv.
  • 22601 Zip Code
  • ACTIVE Status
104 Kapok Cir, Winchester image
104 Kapok Cir, Winchester $420,000 ▼

Welcome to the neighborhood of Apple Ridge in Eastern Frederick County. You won't find a nicer home or more quiet cul-d-sac anywhere let alone one that has been more tast...

  • 3 Beds
  • 3 Baths
  • Apple Ridge SubDv.
  • 22602 Zip Code
  • ACTIVE Status

Between $400K - $500K Winchester Real Estate

Our website features the best real estate search for between $400k - $500k properties available in Winchester and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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Anne Nouri

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