Airbnb Properties for Sale in Winchester, TN

Looking for a vacation rental investment in Winchester, TN with high ROI ?

Explore a range of newly added short-term rental homes in Winchester, TN. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winchester, TN

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
220 Bryan Dr Winchester, TN Like new remodeled home in Bell Acres Subdivision. Featuring 2 master suites, one downstai...	4 beds \| 3 baths \| 2,209 sq.ft.	$459,000	Airbnb cash on cash: 4.01% Traditional cash on cash: 3.57% Airbnb Rental Income: $3188 Traditional Rental Income: $2278 Airbnb ROI: 4.01% Traditional ROI: 3.57%
208 Loop Dr Winchester, TN 208 Loop Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 2,906 sq.ft.	$1,050,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 0.62% Airbnb Rental Income: $3188 Traditional Rental Income: $2369 Airbnb ROI: 0.73% Traditional ROI: 0.62%
305 Oak Leaf Cir Winchester, TN 305 Oak Leaf Cir, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 1,864 sq.ft.	$357,900	Airbnb cash on cash: 5.36% Traditional cash on cash: 3.5% Airbnb Rental Income: $3188 Traditional Rental Income: $1841 Airbnb ROI: 5.36% Traditional ROI: 3.5%
71 Fanning Bend Dr Winchester, TN 71 Fanning Bend Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 2,583 sq.ft.	$1,075,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.25% Airbnb Rental Income: $3188 Traditional Rental Income: $2352 Airbnb ROI: 0.36% Traditional ROI: 0.25%
101 Cypress Point Dr Winchester, TN 101 Cypress Point Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 3,738 sq.ft.	$749,900	Airbnb cash on cash: 1.66% Traditional cash on cash: 1.11% Airbnb Rental Income: $3188 Traditional Rental Income: $2087 Airbnb ROI: 1.66% Traditional ROI: 1.11%
356 Ridgecrest Dr Winchester, TN 356 Ridgecrest Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 3,705 sq.ft.	$689,900	Airbnb cash on cash: 1.98% Traditional cash on cash: 1.37% Airbnb Rental Income: $3188 Traditional Rental Income: $2075 Airbnb ROI: 1.98% Traditional ROI: 1.37%
44 Houghton Dr Winchester, TN 44 Houghton Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 2,197 sq.ft.	$399,900	Airbnb cash on cash: 4.63% Traditional cash on cash: 3.09% Airbnb Rental Income: $3188 Traditional Rental Income: $1893 Airbnb ROI: 4.63% Traditional ROI: 3.09%
205 8th Ave NW Winchester, TN 205 8th Ave NW, Winchester, TN 37398 \| Single Family Residential	3 beds \| 1 baths \| 1,333 sq.ft.	$224,900	Airbnb cash on cash: 3.88% Traditional cash on cash: 3.53% Airbnb Rental Income: $1765 Traditional Rental Income: $1208 Airbnb ROI: 3.88% Traditional ROI: 3.53%
240 Myers Road Winchester, TN Welcome to peaceful country living in beautiful Winchester, Tennessee. Priced below apprai...	4 beds \| 3 baths \| 1,960 sq.ft.	$300,000	Airbnb cash on cash: 6.88% Traditional cash on cash: 4.96% Airbnb Rental Income: $3188 Traditional Rental Income: $1926 Airbnb ROI: 6.88% Traditional ROI: 4.96%
206 Homeward Ave Winchester, TN 206 Homeward Ave, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 1,999 sq.ft.	$299,900	Airbnb cash on cash: 6.71% Traditional cash on cash: 4.39% Airbnb Rental Income: $3188 Traditional Rental Income: $1812 Airbnb ROI: 6.71% Traditional ROI: 4.39%
65 Pontoon Pl Winchester, TN 65 Pontoon Pl, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 2,592 sq.ft.	$635,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 1.79% Airbnb Rental Income: $3188 Traditional Rental Income: $2348 Airbnb ROI: 1.99% Traditional ROI: 1.79%
1035 Franklin Heights Dr Winchester, TN 1035 Franklin Heights Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 3,323 sq.ft.	$640,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 1.77% Airbnb Rental Income: $3188 Traditional Rental Income: $2176 Airbnb ROI: 2.26% Traditional ROI: 1.77%
2124 Boswell Rd Winchester, TN 2124 Boswell Rd, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 6,803 sq.ft.	$999,500	Airbnb cash on cash: 0.85% Traditional cash on cash: 0.42% Airbnb Rental Income: $3188 Traditional Rental Income: $2069 Airbnb ROI: 0.85% Traditional ROI: 0.42%
102 Summer Lake Ct Winchester, TN 102 Summer Lake Ct, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 2,688 sq.ft.	$675,000	Airbnb cash on cash: 2.07% Traditional cash on cash: 1.98% Airbnb Rental Income: $3188 Traditional Rental Income: $2410 Airbnb ROI: 2.07% Traditional ROI: 1.98%
1111 Holders Cove Rd Winchester, TN 1111 Holders Cove Rd, Winchester, TN 37398 \| Single Family Residential	3 beds \| 1 baths \| 1,508 sq.ft.	$369,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 1.54% Airbnb Rental Income: $1765 Traditional Rental Income: $1218 Airbnb ROI: 1.73% Traditional ROI: 1.54%
65 Campfire Ct Winchester, TN 65 Campfire Ct, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 2,564 sq.ft.	$474,900	Airbnb cash on cash: 2.95% Traditional cash on cash: 2.16% Airbnb Rental Income: $3188 Traditional Rental Income: $2117 Airbnb ROI: 2.95% Traditional ROI: 2.16%
58 Island Way Winchester, TN 58 Island Way, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 2,660 sq.ft.	$439,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.24% Airbnb Rental Income: $3188 Traditional Rental Income: $2053 Airbnb ROI: 3.25% Traditional ROI: 2.24%
188 Wiseman Ln Winchester, TN 188 Wiseman Ln, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 2,269 sq.ft.	$469,900	Airbnb cash on cash: 3.7% Traditional cash on cash: 2.79% Airbnb Rental Income: $3188 Traditional Rental Income: $2069 Airbnb ROI: 3.7% Traditional ROI: 2.79%
0 Ridgecrest Dr Winchester, TN 0 Ridgecrest Dr, Winchester, TN 37398 \| Other	4 beds \| 3 baths \| 3,165 sq.ft.	$794,500	Airbnb cash on cash: 1.5% Traditional cash on cash: -1.16% Airbnb Rental Income: $3188 Traditional Rental Income: $502 Airbnb ROI: 1.5% Traditional ROI: -1.16%
205 Houghton Dr Winchester, TN 205 Houghton Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 2,640 sq.ft.	$364,500	Airbnb cash on cash: 5.23% Traditional cash on cash: 5.05% Airbnb Rental Income: $3188 Traditional Rental Income: $2404 Airbnb ROI: 5.23% Traditional ROI: 5.05%
111 Dogwood Ln Winchester, TN 111 Dogwood Ln, Winchester, TN 37398 \| Single Family Residential	3 beds \| 1 baths \| 1,822 sq.ft.	$300,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.06% Airbnb Rental Income: $1765 Traditional Rental Income: $1156 Airbnb ROI: 2.5% Traditional ROI: 2.06%
400 Cessna Cir Winchester, TN 400 Cessna Cir, Winchester, TN 37398 \| Single Family Residential	5 beds \| 3 baths \| 2,218 sq.ft.	$309,000	Airbnb cash on cash: 7.71% Traditional cash on cash: 5.38% Airbnb Rental Income: $3622 Traditional Rental Income: $2153 Airbnb ROI: 7.71% Traditional ROI: 5.38%
73 Cypress Point Dr Winchester, TN 73 Cypress Point Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 2,684 sq.ft.	$879,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.16% Airbnb Rental Income: $3188 Traditional Rental Income: $2463 Airbnb ROI: 1.16% Traditional ROI: 1.16%
2607 Old Tullahoma Rd Winchester, TN 2607 Old Tullahoma Rd, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 2,645 sq.ft.	$494,900	Airbnb cash on cash: 3.42% Traditional cash on cash: 2.53% Airbnb Rental Income: $3188 Traditional Rental Income: $2053 Airbnb ROI: 3.42% Traditional ROI: 2.53%
270 Wood Bluff Rd Winchester, TN 270 Wood Bluff Rd, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 2,228 sq.ft.	$459,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.63% Airbnb Rental Income: $3188 Traditional Rental Income: $1957 Airbnb ROI: 3.82% Traditional ROI: 2.63%
107 Highland Dr Winchester, TN 107 Highland Dr, Winchester, TN 37398 \| Single Family Residential	3 beds \| 1 baths \| 1,348 sq.ft.	$210,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 4.2% Airbnb Rental Income: $1765 Traditional Rental Income: $1269 Airbnb ROI: 4.27% Traditional ROI: 4.2%
25 Lookout Dr Winchester, TN 25 Lookout Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 1,887 sq.ft.	$454,900	Airbnb cash on cash: 3.77% Traditional cash on cash: 2.62% Airbnb Rental Income: $3188 Traditional Rental Income: $1980 Airbnb ROI: 3.77% Traditional ROI: 2.62%
53 River Watch Way Winchester, TN 53 River Watch Way, Winchester, TN 37398 \| Single Family Residential	5 beds \| 4 baths \| 3,095 sq.ft.	$879,900	Airbnb cash on cash: 1.4% Traditional cash on cash: 1.3% Airbnb Rental Income: $3622 Traditional Rental Income: $2741 Airbnb ROI: 1.4% Traditional ROI: 1.3%
260 Lookout Dr Winchester, TN 260 Lookout Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 3,115 sq.ft.	$649,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 1.88% Airbnb Rental Income: $3188 Traditional Rental Income: $2297 Airbnb ROI: 2.16% Traditional ROI: 1.88%
103 Anderton Dr Winchester, TN 103 Anderton Dr, Winchester, TN 37398 \| Townhouse	5 beds \| 3 baths \| 2,160 sq.ft.	$486,800	Airbnb cash on cash: 3.63% Traditional cash on cash: 2.53% Airbnb Rental Income: $3622 Traditional Rental Income: $2325 Airbnb ROI: 3.63% Traditional ROI: 2.53%
124 Lookout Dr Winchester, TN 124 Lookout Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 1,890 sq.ft.	$444,900	Airbnb cash on cash: 3.89% Traditional cash on cash: 2.71% Airbnb Rental Income: $3188 Traditional Rental Income: $1976 Airbnb ROI: 3.89% Traditional ROI: 2.71%
88 Norwood Creek Rd Winchester, TN 88 Norwood Creek Rd, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 2,544 sq.ft.	$599,999	Airbnb cash on cash: 2.53% Traditional cash on cash: 2.18% Airbnb Rental Income: $3188 Traditional Rental Income: $2272 Airbnb ROI: 2.53% Traditional ROI: 2.18%
369 Fanning Bend Dr Winchester, TN 369 Fanning Bend Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 4 baths \| 2,376 sq.ft.	$899,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 0.7% Airbnb Rental Income: $3188 Traditional Rental Income: $2432 Airbnb ROI: 0.74% Traditional ROI: 0.7%
128 Bel Aire Dr Winchester, TN 128 Bel Aire Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 1 baths \| 1,923 sq.ft.	$309,900	Airbnb cash on cash: 6.44% Traditional cash on cash: 2.37% Airbnb Rental Income: $3188 Traditional Rental Income: $1282 Airbnb ROI: 6.44% Traditional ROI: 2.37%
1200 Little St Winchester, TN 1200 Little St, Winchester, TN 37398 \| Single Family Residential	5 beds \| 2 baths \| 1,600 sq.ft.	$310,000	Airbnb cash on cash: 7.68% Traditional cash on cash: 4% Airbnb Rental Income: $3622 Traditional Rental Income: $1756 Airbnb ROI: 7.68% Traditional ROI: 4%
105 W Paradise Dr Winchester, TN 105 W Paradise Dr, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 4,400 sq.ft.	$850,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 0.98% Airbnb Rental Income: $3188 Traditional Rental Income: $2236 Airbnb ROI: 1.27% Traditional ROI: 0.98%
1400 Holders Cove Rd Winchester, TN 1400 Holders Cove Rd, Winchester, TN 37398 \| Single Family Residential	3 beds \| 1 baths \| 1,490 sq.ft.	$325,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 2.15% Airbnb Rental Income: $1765 Traditional Rental Income: $1272 Airbnb ROI: 2.19% Traditional ROI: 2.15%
379 Hooper Rd Winchester, TN 379 Hooper Rd, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 2,793 sq.ft.	$699,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 1.49% Airbnb Rental Income: $3188 Traditional Rental Income: $2176 Airbnb ROI: 1.94% Traditional ROI: 1.49%
154 Barefoot Way Winchester, TN 154 Barefoot Way, Winchester, TN 37398 \| Single Family Residential	4 beds \| 2 baths \| 2,224 sq.ft.	$649,000	Airbnb cash on cash: 2.02% Traditional cash on cash: 1.46% Airbnb Rental Income: $3188 Traditional Rental Income: $2126 Airbnb ROI: 2.02% Traditional ROI: 1.46%
59 Turtle Ct Winchester, TN 59 Turtle Ct, Winchester, TN 37398 \| Single Family Residential	4 beds \| 3 baths \| 2,560 sq.ft.	$695,900	Airbnb cash on cash: 1.66% Traditional cash on cash: 1.56% Airbnb Rental Income: $3188 Traditional Rental Income: $2401 Airbnb ROI: 1.66% Traditional ROI: 1.56%

Vacation Rentals in Winchester

There are 55 vacation rental properties available for sale in the city of Winchester . The median list price of Airbnb properties available for sale in Winchester is $317,286 and the average price per square foot is $135. The cash on cash return on vacation rentals in Winchester is 1.00%. The average monthly short term rental income in Winchester is $1,765.

Winchester, TN Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 55 Airbnb properties available for sale in Winchester.

In 2026, the best neighborhood to buy short term rental property is Winchester.

In June 2026, the average Airbnb occupancy rate in Winchester is 23%.

Airbnb data on vacation rentals in Winchester, TN is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winchester, TN market insights, guest information and booking details, seasonality trends and historical Winchester, TN Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winchester, TN

220 Bryan Dr

Winchester, TN

4 beds | 3 baths | 2,209 sq.ft.

$459,000

Airbnb cash on cash: 4.01%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $3188

Traditional Rental Income: $2278

Airbnb ROI: 4.01%

Traditional ROI: 3.57%

208 Loop Dr

Winchester, TN

4 beds | 3 baths | 2,906 sq.ft.

$1,050,000

Airbnb cash on cash: 0.73%

Traditional cash on cash: 0.62%

Airbnb Rental Income: $3188

Traditional Rental Income: $2369

Airbnb ROI: 0.73%

Traditional ROI: 0.62%

305 Oak Leaf Cir

Winchester, TN

4 beds | 3 baths | 1,864 sq.ft.

$357,900

Airbnb cash on cash: 5.36%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $3188

Traditional Rental Income: $1841

Airbnb ROI: 5.36%

Traditional ROI: 3.5%

71 Fanning Bend Dr

Winchester, TN

4 beds | 3 baths | 2,583 sq.ft.

$1,075,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 0.25%

Airbnb Rental Income: $3188

Traditional Rental Income: $2352

Airbnb ROI: 0.36%

Traditional ROI: 0.25%

101 Cypress Point Dr

Winchester, TN

4 beds | 3 baths | 3,738 sq.ft.

$749,900

Airbnb cash on cash: 1.66%

Traditional cash on cash: 1.11%

Airbnb Rental Income: $3188

Traditional Rental Income: $2087

Airbnb ROI: 1.66%

Traditional ROI: 1.11%

356 Ridgecrest Dr

Winchester, TN

4 beds | 3 baths | 3,705 sq.ft.

$689,900

Airbnb cash on cash: 1.98%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $3188

Traditional Rental Income: $2075

Airbnb ROI: 1.98%

Traditional ROI: 1.37%

44 Houghton Dr

Winchester, TN

4 beds | 2 baths | 2,197 sq.ft.

$399,900

Airbnb cash on cash: 4.63%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $3188

Traditional Rental Income: $1893

Airbnb ROI: 4.63%

Traditional ROI: 3.09%

205 8th Ave NW

Winchester, TN

3 beds | 1 baths | 1,333 sq.ft.

$224,900

Airbnb cash on cash: 3.88%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $1765

Traditional Rental Income: $1208

Airbnb ROI: 3.88%