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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

Currently Rented
Listed for sale 3 days ago
$ 239,000
ROI
29.7
Cash Flow/m
660- 5 Bed
- 3 Bath
- 3007 sft
221 S Highland St, Winchester, KY, 40391

Listed for sale 7 days ago
$ 275,000
ROI
24.6
Cash Flow/m
369- 3 Bed
- 3 Bath
- 1787 sft
304 Newcastle Ln, Winchester, KY, 40391

$ 279,900
ROI
24.5
Cash Flow/m
366- 3 Bed
- 3 Bath
- 1604 sft
136 Sturbridge Ln, Winchester, KY, 40391

Fix & Flip
$ 125,000
ROI
26.6
Cash Flow/m
239- 3 Bed
- 1 Bath
- 900 sft
25 Oliver St, 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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