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Back in 2014, spending $500,000 on a house was generally reserved for high earners. The typical U.S. home sold for $159,000, while starter homes averaged just $101,000. Fast-forward to today, and prices have more than doubled: A home now sells for $440,000, with starter homes approaching $300,000. 

These current prices have put homeownership out of reach for many – and things don't look to be improving. Prices are still , affordability keeps dropping, and are becoming harder to find as home values . This has created a very sluggish and difficult housing market. In fact, even the usual busy spring and summer buying seasons were this year.

While $500,000 once stretched much further, in many cities today, it's not nearly enough. But what about Winchester?

To find out, found listings near the $500,000 mark to see what types of homes you can actually afford in Winchester right now. Listings below $500,000 were included if necessary.

513 Monticello St, Winchester, VA 22601
- Price: $500,000
- 7 bedrooms, 1.5 bathrooms
- Square feet: 1,175
- See 513 Monticello St, Winchester, VA 22601 on

386 Round Hill Rd, Winchester, VA 22602
- Price: $475,000
- 6 bedrooms, 3 bathrooms
- Square feet: 2,736
- See 386 Round Hill Rd, Winchester, VA 22602 on

131 Emerald Ln, Berkeley Springs, WV 25411
- Price: $488,500
- 5 bedrooms, 3 bathrooms
- Square feet: 3,673
- See 131 Emerald Ln, Berkeley Springs, WV 25411 on

110 Carter Pl, Winchester, VA 22602
- Price: $494,970
- 5 bedrooms, 3 bathrooms
- Square feet: 3,116
- See 110 Carter Pl, Winchester, VA 22602 on

201 Parkway St, Winchester, VA 22601
- Price: $495,000
- 4 bedrooms, 4 bathrooms
- Square feet: 1,627
- See 201 Parkway St, Winchester, VA 22601 on

202 Senseny Glen Dr, Winchester, VA 22602
- Price: $499,000
- 4 bedrooms, 3.5 bathrooms
- Square feet: 3,982
- See 202 Senseny Glen Dr, Winchester, VA 22602 on

200 Stephens Run St, Stephens City, VA 22655
- Price: $499,000
- 4 bedrooms, 3.5 bathrooms
- Square feet: 3,844
- See 200 Stephens Run St, Stephens City, VA 22655 on

219 Milam Dr, Winchester, VA 22602
- Price: $489,000
- 4 bedrooms, 3 bathrooms
- Square feet: 2,654
- See 219 Milam Dr, Winchester, VA 22602 on

510 N Loudoun St, Winchester, VA 22601
- Price: $475,000
- 4 bedrooms, 3 bathrooms
- Square feet: 2,376
- See 510 N Loudoun St, Winchester, VA 22601 on

16497 Northwestern Pike, Augusta, WV 26704
- Price: $474,888
- 4 bedrooms, 2.5 bathrooms
- Square feet: 2,308
- See 16497 Northwestern Pike, Augusta, WV 26704 on

121 Midsummer Ln, Middletown, VA 22645
- Price: $489,999
- 4 bedrooms, 2.5 bathrooms
- Square feet: 1,840
- See 121 Midsummer Ln, Middletown, VA 22645 on

109 Shelby Ct, Winchester, VA 22602
- Price: $499,999
- 3 bedrooms, 2.5 bathrooms
- Square feet: 2,412
- See 109 Shelby Ct, Winchester, VA 22602 on

117 Wagtail Ln, Winchester, VA 22603
- Price: $496,129
- 3 bedrooms, 2.5 bathrooms
- Square feet: 2,195
- See 117 Wagtail Ln, Winchester, VA 22603 on

120 Midsummer Ln, Middletown, VA 22645
- Price: $479,999
- 3 bedrooms, 2.5 bathrooms
- Square feet: 1,986
- See 120 Midsummer Ln, Middletown, VA 22645 on

106 Midsummer Ln, Middletown, VA 22645
- Price: $469,999
- 3 bedrooms, 2.5 bathrooms
- Square feet: 1,980
- See 106 Midsummer Ln, Middletown, VA 22645 on

703 National Ave, Winchester, VA 22601
- Price: $479,900
- 3 bedrooms, 2.5 bathrooms
- Square feet: 1,976
- See 703 National Ave, Winchester, VA 22601 on

102 Midsummer Ln, Middletown, VA 22645
- Price: $469,999
- 3 bedrooms, 2.5 bathrooms
- Square feet: 1,840
- See 102 Midsummer Ln, Middletown, VA 22645 on

129 Jalapa Trl, Winchester, VA 22602
- Price: $475,000
- 3 bedrooms, 2 bathrooms
- Square feet: 2,400
- See 129 Jalapa Trl, Winchester, VA 22602 on

101 Delaware Trl, Winchester, VA 22602
- Price: $489,000
- 3 bedrooms, 2 bathrooms
- Square feet: 2,302
- See 101 Delaware Trl, Winchester, VA 22602 on

539 River Bend Dr, Paw Paw, WV 25434
- Price: $485,000
- 3 bedrooms, 2 bathrooms
- Square feet: 2,179
- See 539 River Bend Dr, Paw Paw, WV 25434 on

421 Superior Ave, Winchester, VA 22601
- Price: $469,700
- 3 bedrooms, 2 bathrooms
- Square feet: 1,800
- See 421 Superior Ave, Winchester, VA 22601 on

311 Akern Ln, Cross Junction, VA 22625
- Price: $499,900
- 3 bedrooms, 2 bathrooms
- Square feet: 1,794
- See 311 Akern Ln, Cross Junction, VA 22625 on

15 Downhill Cir, Cross Junction, VA 22625
- Price: $489,000
- 3 bedrooms, 2 bathrooms
- Square feet: 1,760
- See 15 Downhill Cir, Cross Junction, VA 22625 on

Lot 163-101 Woodland Ln, Cross Junction, VA 22625
- Price: $479,400
- 3 bedrooms, 2 bathrooms
- Square feet: 1,760
- See Lot 163-101 Woodland Ln, Cross Junction, VA 22625 on

1420 Fishel Rd, Winchester, VA 22602
- Price: $499,900
- 3 bedrooms, 2 bathrooms
- Square feet: 1,680
- See 1420 Fishel Rd, Winchester, VA 22602 on

113 Mimosa Dr, Stephens City, VA 22655
- Price: $475,000
- 3 bedrooms, 2 bathrooms
- Square feet: 1,651
- See 113 Mimosa Dr, Stephens City, VA 22655 on

100 Midsummer Ln, Middletown, VA 22645
- Price: $484,999
- 3 bedrooms, 2 bathrooms
- Square feet: 1,610
- See 100 Midsummer Ln, Middletown, VA 22645 on

3634 Wardensville Grade, Winchester, VA 22602
- Price: $499,000
- 3 bedrooms, 1 bathroom
- Square feet: 2,050
- See 3634 Wardensville Grade, Winchester, VA 22602 on

118 Milkweed Dr, Lake Frederick, VA 22630
- Price: $484,900
- 2 bedrooms, 2 bathrooms
- Square feet: 1,632
- See 118 Milkweed Dr, Lake Frederick, VA 22630 on

9987 Capon River Rd, Yellow Spring, WV 26865
- Price: $499,999
- 2 bedrooms, 1 bathroom
- Square feet: 900
- See 9987 Capon River Rd, Yellow Spring, WV 26865 on