New39$384,990
3 bd · 4 ba · 1,756 sqft
Homesite 126 Monteith Dr, Winchester, VA
Brittany Newman · DRB Group Realty, LLC
Homes Under $500K in Winchester, VA
Hide MapHomes Under $500K in Winchester, VA
24 of 202 Listings
New39$384,990
3 bd · 4 ba · 1,756 sqft
Homesite 126 Monteith Dr, Winchester, VA
Brittany Newman · DRB Group Realty, LLC
New13$419,000
3 bd · 3 ba · 1,453 sqft
131 Shirley St, Winchester, VA
Brandon W Pifer · Pifer Realty, LLC
New44$350,000
3 bd · 2 ba · 1,317 sqft
144 Apple Valley Rd, Winchester, VA
Julie M Teets · ERA Oakcrest Realty, Inc.
New27$220,000
2 bd · 1 ba · 560 sqft
610 Puma Trl, Winchester, VA
James Podoley · EXP Realty, LLC
47$349,999
4 bd · 2 ba · 1,812 sqft
120 Comanche Trl, Winchester, VA
Michelle L Belford · NextHome Realty Select
99$395,600
4 bd · 2 ba · 1,860 sqft
178 Payne Rd, Winchester, VA
Wanda Garris Miller · Century 21 Redwood Realty
25$299,500
3 bd · 2 ba · 1,138 sqft
621 Watson Ave, Winchester, VA
Caleb Christen Fowler · Samson Properties
19$375,000
3 bd · 2 ba · 1,452 sqft
265 McDonald Rd, Winchester, VA
Verria Hairston · Open Door Brokerage, LLC
23$260,000
2 bd · 1 ba · 900 sqft
107 Little River Dr, Winchester, VA
Erin M Kavanagh · EXP Realty, LLC
54$459,900
3 bd · 2 ba · 1,834 sqft
991 Front Royal Pike, Winchester, VA
James W. King, Jr. · Re/Max Roots
40$374,900
3 bd · 3 ba · 1,696 sqft
1957 Cidermill Ln, Winchester, VA
Matthew Michael Kilmer · Samson Properties
59$499,900
3 bd · 2 ba · 1,479 sqft
1960 Siler Rd, Winchester, VA
Natasha Roberts · Realty ONE Group Old Towne
48$439,000
5 bd · 3 ba · 2,508 sqft
300 Pembridge Dr, Winchester, VA
Magnolia L Halkowitz · ERA Oakcrest Realty, Inc.
56$380,000
4 bd · 3 ba · 2,243 sqft
900 Enfield Dr, Winchester, VA
Alexandra Lilian Brown · Spring Hill Real Estate, LLC.
2$300,000
3 bd · 1 ba · 1,008 sqft
111 Haven Ter, Winchester, VA
Erin M Kavanagh · EXP Realty, LLC
54$295,000
2 bd · 3 ba · 2,148 sqft
159 Aspen Trl, Winchester, VA
Kimberly C Baggett · EXP Realty, LLC
22$389,990
4 bd · 4 ba · 2,200 sqft
Homesite 42 Shuoner Ct, Winchester, VA
James Thomas · New Home Star Virginia, LLC
4$290,000
2 bd · 3 ba · 1,868 sqft
323 Copperfield Ln, Winchester, VA
Rebecca Sims · Century 21 Redwood Realty
22$389,990
4 bd · 4 ba · 2,200 sqft
Homesite 41 Shuoner Ct, Winchester, VA
James Thomas · New Home Star Virginia, LLC
22$334,000
3 bd · 3 ba · 1,680 sqft
308 Fawn Dr, Winchester, VA
Steve A DuBrueler · Coldwell Banker Premier
15$287,000
3 bd · 1 ba · 1,104 sqft
700 Tomahawk Trl, Winchester, VA
Stacy Priddy · Berkshire Hathaway HomeServices PenFed Realty
65$359,000
3 bd · 2 ba · 1,710 sqft
812 Appleseed Ct, Winchester, VA
Feletia Van Valkenburg Sharples · Realty FC
93$355,000
2 bd · 2 ba · 1,234 sqft
1847 Melvor Ln, Winchester, VA
Lisette B. Turner · Century 21 Redwood Realty
29$409,000
4 bd · 1 ba · 1,768 sqft
322 E Piccadilly, Winchester, VA
Leslie A. Webb · Long & Foster Real Estate, Inc.
Bright MLSSource: HJN community data
August 2026 · This period is still settling
Selling at 99.0% of asking price
Buyers here are paying below asking. MLS · 86 sales · as of Aug 31, 2026