Real Estate Investment Properties for Sale in Winchester, TN
Looking for investment property in Winchester, TN with high ROI ?
Explore a variety of short-term homes & houses in Winchester, TN. Invest wisely with VRBO & Winchester, TN Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Winchester, TN
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
50 Maple DrWinchester, TNFireplace in den w/gas logs, formal living room & dining room. Located in Dripping Springs... |
3 beds | 2 baths | 1,493 sq.ft. |
$575,000 |
Airbnb cash on cash: 0.49%
|
512 Cline Ridge RdWinchester, TNDeeded lot #5 on Out Lot D located on White Oak is included with sale. There is a floating... |
3 beds | 2 baths | 1,388 sq.ft. |
$510,000 |
Airbnb cash on cash: 0.79%
|
236 Tims Ford DrWinchester, TNREDUCED!! European style home located within Tims Ford State Park! Master suite down, 3 be... |
4 beds | 4 baths | 6,152 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 0.62%
|
714 N Cedar StWinchester, TNMove - In Ready!! This home has 2 driveways! Renovated cottage style home close to schoo... |
2 beds | 1 baths | 1,150 sq.ft. |
$175,000 |
Airbnb cash on cash: 2.56%
|
182 Loop DrWinchester, TNGORGEOUS, Home that is 2 homes in one. The top floor is 2 bedroom and 2 bath with kitch... |
5 beds | 3 baths | 3,640 sq.ft. |
$875,000 |
Airbnb cash on cash: 2.06%
|
220 Bryan DrWinchester, TNLike 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%
|
111 Barefoot WayWinchester, TNWelcome to Barefoot Bay a quaint, gated waterfront community in beautiful Winchester, TN. ... |
4 beds | 2 baths | 1,981 sq.ft. |
$614,900 |
Airbnb cash on cash: 2.22%
|
140 Huntington Dr SWinchester, TNTims Ford Lake House with private dock. Fantastic renovated home in quiet cul-de-sac, priv... |
3 beds | 2 baths | 1,872 sq.ft. |
$749,000 |
Airbnb cash on cash: 0.6%
|
319 Campfire CtWinchester, TNUNDER CONSTRUCTION: This designer home built by Legacy Lake Homes features a first level p... |
3 beds | 3 baths | 2,579 sq.ft. |
$595,000 |
Airbnb cash on cash: 0.73%
|
0 Wakeboard WayWinchester, TNCOME ENJOY THE LAKE LIFE! TO BE BUILT! Enjoy a resort style atmosphere in beautiful Twin C... |
N/A beds | N/A baths | 2,689 sq.ft. |
$145,000 |
Airbnb cash on cash: -2.66%
|
0 Paddleboard CtWinchester, TN3 Car Garage Semi-Custom Craftsman's Style Floor Plan to be built on cul de sac lot with ... |
N/A beds | N/A baths | 3,172 sq.ft. |
$149,900 |
Airbnb cash on cash: -3.73%
|
3896 Lynchburg RdWinchester, TNAbsolute Gem! Beautiful full Brick Home and rare listing right off Lynchburg Rd located cl... |
3 beds | 2 baths | 1,509 sq.ft. |
$384,000 |
Airbnb cash on cash: 2.04%
|
118 Bel Aire DrWinchester, TNSeller is asking for all offers to be due by 5pm on Wednesday. Multiple offers received. O... |
3 beds | 2 baths | 1,476 sq.ft. |
$239,900 |
Airbnb cash on cash: 3.88%
|
70 Island WayWinchester, TNIf you've been dreaming of the perfect lake life, this is your chance to wake up and make ... |
4 beds | 3 baths | 2,578 sq.ft. |
$499,900 |
Airbnb cash on cash: 2.98%
|
90 Owl Hollow LnWinchester, TNFor more information, contact James Bowden at (931) 434-4225. Visit http://www.crye-leike.... |
3 beds | 2 baths | 2,431 sq.ft. |
$449,000 |
Airbnb cash on cash: 1.63%
|
667 Maple Bend RdWinchester, TN
|
2 beds | 1 baths | 1,200 sq.ft. |
$320,000 |
Airbnb cash on cash: 0.43%
|
282 Owl Hollow LnWinchester, TNWelcome to your dream lakefront property, where modern luxury meets serene natural beauty.... |
4 beds | 3 baths | 3,484 sq.ft. |
$844,900 |
Airbnb cash on cash: 1.67%
|
1445 Georgia Crossing RoadWinchester, TNThis stunning Franklin County, Tennessee, country home, originally built in 1912, has unde... |
3 beds | 2 baths | 1,812 sq.ft. |
$349,000 |
Airbnb cash on cash: 2.46%
|
220 Deer View LaneWinchester, TNThis stunning Franklin County, Tennessee, farm offers a pristine rural setting for those s... |
3 beds | 2 baths | 2,900 sq.ft. |
$1,650,000 |
Airbnb cash on cash: -0.37%
|
0 Aedc RdWinchester, TN0 Aedc Rd, Winchester, TN 37398 | Other |
N/A beds | N/A baths | N/A |
$129,000 |
Airbnb cash on cash: -1.3%
|
3819 Tullahoma HwyWinchester, TN3819 Tullahoma Hwy, Winchester, TN 37398 | Other |
N/A beds | N/A baths | N/A |
$1,800,000 |
Airbnb cash on cash: -1.67%
|
67 Edgefield CtWinchester, TN67 Edgefield Ct, Winchester, TN 37398 | Other |
N/A beds | N/A baths | N/A |
$64,900 |
Airbnb cash on cash: -1.69%
|
66 Edgefield CtWinchester, TN66 Edgefield Ct, Winchester, TN 37398 | Other |
N/A beds | N/A baths | N/A |
$64,900 |
Airbnb cash on cash: -1.69%
|
0 Cooper LnWinchester, TN0 Cooper Ln, Winchester, TN 37398 | Other |
N/A beds | N/A baths | N/A |
$72,000 |
Airbnb cash on cash: -1%
|
657 Pickney RdWinchester, TN657 Pickney Rd, Winchester, TN 37398 | Single Family Residential |
3 beds | 2 baths | 2,782 sq.ft. |
$600,000 |
Airbnb cash on cash: 0.42%
|
208 Loop DrWinchester, TN208 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%
|
101 N Shephard StWinchester, TN101 N Shephard St, Winchester, TN 37398 | Single Family Residential |
3 beds | 2 baths | 1,358 sq.ft. |
$327,900 |
Airbnb cash on cash: 1.97%
|
383 Strawberry DrWinchester, TN383 Strawberry Dr, Winchester, TN 37398 | Single Family Residential |
3 beds | 2 baths | 1,296 sq.ft. |
$298,000 |
Airbnb cash on cash: 2.53%
|
305 Oak Leaf CirWinchester, TN305 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%
|
44 Hammock DrWinchester, TN44 Hammock Dr, Winchester, TN 37398 | Single Family Residential |
3 beds | 2 baths | 2,296 sq.ft. |
$549,995 |
Airbnb cash on cash: 0.24%
|
219 Old Mill RdWinchester, TN219 Old Mill Rd, Winchester, TN 37398 | Single Family Residential |
3 beds | 2 baths | 3,050 sq.ft. |
$399,000 |
Airbnb cash on cash: 1.47%
|
102 Cannonball CtWinchester, TN102 Cannonball Ct, Winchester, TN 37398 | Single Family Residential |
2 beds | 2 baths | 1,425 sq.ft. |
$549,900 |
Airbnb cash on cash: -0.82%
|
99 N Shephard StWinchester, TN99 N Shephard St, Winchester, TN 37398 | Single Family Residential |
3 beds | 2 baths | 1,213 sq.ft. |
$299,999 |
Airbnb cash on cash: 2.31%
|
61 Joy CirWinchester, TN61 Joy Cir, Winchester, TN 37398 | Single Family Residential |
6 beds | 5 baths | 6,176 sq.ft. |
$1,399,900 |
Airbnb cash on cash: 0.16%
|
71 Fanning Bend DrWinchester, TN71 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%
|
101 Cypress Point DrWinchester, TN101 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%
|
356 Ridgecrest DrWinchester, TN356 Ridgecrest Dr, Winchester, TN 37398 | Single Family Residential |
4 beds | 3 baths | 3,705 sq.ft. |
$689,900 |
Airbnb cash on cash: 1.98%
|
44 Houghton DrWinchester, TN44 Houghton Dr, Winchester, TN 37398 | Single Family Residential |
4 beds | 2 baths | 2,197 sq.ft. |
$399,900 |
Airbnb cash on cash: 4.63%
|
Real Estate investment in Winchester, TN
There are 249 properties for sale in the city of Winchester . The median list price in Winchester is $317,286 and the average price per square foot is $135. In June 2026, the average monthly cash on cash return in Winchester is 2.00%. The average monthly rental income in Winchester is $1,842.