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Price: $300K - 500K
Monthly Cash Flow: $1 - $3k+
Home Type: Single Family
Under $300K Investment Properties for Sale in Winchester, KY

Listed for sale 1 day ago
$ 179,900
ROI
32.4
Cash Flow/m
633- 3 Bed
- 2 Bath
- 1635 sft
47 Buckner St, Winchester, KY, 40391

Listed for sale 1 day ago
$ 139,000
ROI
25.5
Cash Flow/m
221- 2 Bed
- 1 Bath
- 904 sft
37 Ashland Ave, Winchester, KY, 40391

Currently Rented
Fix & Flip
Listed for sale 1 day ago
$ 189,999
ROI
26.4
Cash Flow/m
351- 3 Bed
- 1 Bath
- 950 sft
41 Hiawatha Trl, Winchester, KY, 40391

Listed for sale 1 day ago
$ 204,900
ROI
27.1
Cash Flow/m
420- 3 Bed
- 1 Bath
- 1290 sft
60 Hiawatha Trl, Winchester, KY, 40391
Why Invest in Winchester, Kentucky?
Winchester, KY offers strong investment opportunities in homes under $300K, with affordable entry points for single-family rentals. Stable rental demand from local workforce supports consistent cash flow. Average cap rates around 7-8% make it attractive for value-add strategies. Recent appreciation trends and low vacancy rates enhance long-term returns. Proximity to Lexington provides commuter appeal without big-city prices.
9.2%
Avg. ROI
7.8%
Rental Yield
7.5%
Cap Rate
$450/mo
Avg. Cash Flow
$1250/mo
Avg. Rent
4.2%
1Y Appreciation
Frequently Asked Questions
Investors can expect 7-9% ROI with cap rates around 7.5% on single-family homes. Average monthly cash flow is $450 after expenses. Stable rents of $1,200-1,500 support consistent yields.
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