Short Term Rental Investment Properties for Sale in Winchester, KY

Airbnb Potential
$ 135,000
ROI
25.8
Cash Flow/m
225- 2 Bed
- 1 Bath
- 807 sft
3208 Ford Hampton Rd, Winchester, KY, 40391

Airbnb Potential
$ 275,000
ROI
21.9
Cash Flow/m
162- 2 Bed
- 1 Bath
- 1231 sft
682 Athens Boonesboro Rd, Winchester, KY, 40391

Airbnb Potential
$ 139,000
ROI
25.9
Cash Flow/m
236- - Bed
- - Bath
- - sft
7950 Four Mile Rd, Winchester, KY, 40391
or
Here are some other similar properties you might be interested in:
Listed for sale 1 day ago
$ 100,000
ROI
25.7
Cash Flow/m
164- 3 Bed
- 2 Bath
- 1292 sft
727 Louis Coleman Jr Dr, Louisville, KY, 40211

Fix & Flip
Listed for sale 1 day ago
$ 100,000
ROI
25.3
Cash Flow/m
153- 2 Bed
- 1 Bath
- 720 sft
214 Helmwood Dr, Elizabethtown, KY, 42701

Fix & Flip
Listed for sale 5 days ago
$ 100,000
ROI
24.9
Cash Flow/m
143- 3 Bed
- 2 Bath
- 1245 sft
11875 State Route 131, Symsonia, KY, 42082

Listed for sale 4 days ago
$ 100,000
ROI
22.7
Cash Flow/m
81- 1 Bed
- 1 Bath
- 760 sft
535/575 Obanion Ln, Owenton, KY, 40359

Fix & Flip
Listed for sale 5 days ago
$ 100,000
ROI
26.5
Cash Flow/m
186- 2 Bed
- 1 Bath
- 780 sft
1823 W 3rd St, Owensboro, KY, 42301

Listed for sale 6 days ago
$ 100,000
ROI
26.5
Cash Flow/m
188- 3 Bed
- 2 Bath
- 1188 sft
255 Lee Johnson Ln, Dawson Springs, KY, 42408

$ 100,000
ROI
25.2
Cash Flow/m
150- 3 Bed
- 1 Bath
- 1262 sft
4133 State Route 764, Utica, KY, 42376

$ 100,000
ROI
24.9
Cash Flow/m
143- 4 Bed
- 2 Bath
- 1900 sft
103 Bennett Ct, Richmond, KY, 40475

Fix & Flip
$ 100,000
ROI
26.4
Cash Flow/m
185- 2 Bed
- 1 Bath
- 1296 sft
2579 Happy Hollow Rd, Hawesville, KY, 42348

Airbnb Potential
$ 100,000
ROI
26.4
Cash Flow/m
185- 2 Bed
- 2 Bath
- 784 sft
38 Wood Lake Dr, Murray, KY, 42071

$ 100,000
ROI
25.5
Cash Flow/m
159- 3 Bed
- 3 Bath
- 3000 sft
222 Court St, Irvine, KY, 40336

$ 100,000
ROI
-
Cash Flow/m
-- 3 Bed
- 2 Bath
- 1545 sft
1288 Marsh Creek Rd, Strunk, KY, 42649

$ 100,000
ROI
25.8
Cash Flow/m
168- - Bed
- - Bath
- - sft
227 Rochester Ave, Marion, KY, 42064

$ 100,000
ROI
25.6
Cash Flow/m
162- 2 Bed
- 1 Bath
- 841 sft
419 Ray St, Henderson, KY, 42420

Fix & Flip
$ 100,000
ROI
25.5
Cash Flow/m
160- 3 Bed
- 2 Bath
- 1754 sft
8683 Us Highway 119, Calvin, KY, 40813

Fix & Flip
$ 100,000
ROI
26.2
Cash Flow/m
178- 3 Bed
- 2 Bath
- 2088 sft
229 Rand Ave, Lexington, KY, 40508

Motivated Seller
$ 100,000
ROI
26.5
Cash Flow/m
187- 3 Bed
- 2 Bath
- 1937 sft
5166 Big Spring Rd, Vine Grove, KY, 40175

$ 100,000
ROI
25.1
Cash Flow/m
147- 4 Bed
- 2 Bath
- 1368 sft
1910 Russell St, Covington, KY, 41014

Fix & Flip
$ 100,000
ROI
25.4
Cash Flow/m
157- 2 Bed
- 1 Bath
- 1800 sft
6044 Richard Crick Rd, White Plains, KY, 42464

Rental Income
$ 100,000
ROI
25.0
Cash Flow/m
145- 2 Bed
- 1 Bath
- 1071 sft
1110 Main St, Williamsburg, KY, 40769

$ 100,000
ROI
-
Cash Flow/m
-- 3 Bed
- 1 Bath
- 1000 sft
1794 Us Highway 60 E, Salem, KY, 42078

Motivated Seller
$ 100,000
ROI
26.7
Cash Flow/m
192- 3 Bed
- 2 Bath
- 1378 sft
128 Southridge Ests, Verona, KY, 41092

$ 100,000
ROI
25.9
Cash Flow/m
170- 4 Bed
- 2 Bath
- 1600 sft
635 Salisbury Branch Rd, Dema, KY, 41859

$ 100,000
ROI
26.6
Cash Flow/m
190- 4 Bed
- 2 Bath
- 1612 sft
701 S 10th St, Mayfield, KY, 42066
Why Invest in Winchester, Kentucky?
Winchester, KY offers strong potential for **short-term rental** investments amid stable market growth. Kentucky's housing market shows steady appreciation around 5%, supporting solid returns. Average rents align with regional trends, while cap rates remain attractive for cash flow. Renter occupancy is high, bolstered by local employment and tourism demand. Investor metrics indicate reliable **rental yields** near 7-8% with moderate appreciation.
8.5%
Avg. ROI
7.8%
Rental Yield
6.2%
Cap Rate
$1250/mo
Avg. Cash Flow
$1450/mo
Avg. Rent
5.2%
1Y Appreciation
Frequently Asked Questions
Yes, Winchester benefits from tourism and proximity to Lexington, driving demand for short-term stays. Stable appreciation and low vacancy support profitability. Investors see average yields around 7-8%.
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