Real Estate Investment Properties for Sale in Windsor, KY

Looking for investment property in Windsor, KY with high ROI ?

Explore a variety of short-term homes & houses in Windsor, KY. Invest wisely with VRBO & Windsor, KY 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 Windsor, KY

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
No properties are listed in Windsor, Kentucky at the moment.
Other Investment Properties for Sale in Kentucky
4103 Hayden Kyle Ct Prospect , KY Welcome to refined living in this exceptional townhome in the Gardens of Hunters Ridge. De...	4 beds \| 4 baths \| 4,218 sq.ft.	$479,900	Airbnb cash on cash: 4.6% Traditional cash on cash: 5.54% Airbnb Rental Income: $4351 Traditional Rental Income: $3859 Airbnb ROI: 4.6% Traditional ROI: 5.54%
11117 Radleigh Ln Louisville , KY Welcome to 11117 Radleigh Lane, nestled in the highly sought-after Little Spring Farm neig...	4 beds \| 3 baths \| 4,087 sq.ft.	$559,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.54% Airbnb Rental Income: $1115 Traditional Rental Income: $2481 Airbnb ROI: -0.78% Traditional ROI: 2.54%
1144 Leafdale Road HODGENVILLE , KY Beautiful brick bi-level home located just minutes from downtown Hodgenville. This move-in...	4 beds \| 2 baths \| 2,500 sq.ft.	$269,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 4.74% Airbnb Rental Income: $1115 Traditional Rental Income: $1766 Airbnb ROI: 0.7% Traditional ROI: 4.74%
609 Moore Drive Elizabethtown , KY This well-kept 3-bedroom, 1-bath home is move-in ready and full of charm! Built in 2003, i...	3 beds \| 1 baths \| 1,170 sq.ft.	$194,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 5.33% Airbnb Rental Income: $1339 Traditional Rental Income: $1422 Airbnb ROI: 2.65% Traditional ROI: 5.33%
857 Malabu Drive Lexington , KY BOM due to buyer financing. Malabu Hills Condominium. Lovely 2 level Condominium centrall...	3 beds \| 3 baths \| 1,582 sq.ft.	$249,000	Airbnb cash on cash: 3.28% Traditional cash on cash: 4.95% Airbnb Rental Income: $2032 Traditional Rental Income: $1898 Airbnb ROI: 3.28% Traditional ROI: 4.95%
1025 Lydia St Louisville , KY Fall in love with this adorable Germantown bungalowâjust steps from all your favorite sp...	2 beds \| 1 baths \| 1,250 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $1415 Airbnb ROI: N/A Traditional ROI: 3.34%
309 E Market St #213 Louisville , KY Escape into your private oasis, in the middle of downtown Louisville, at the Mercantile Ga...	2 beds \| 2 baths \| 1,402 sq.ft.	$343,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.42% Airbnb Rental Income: $null Traditional Rental Income: $2070 Airbnb ROI: N/A Traditional ROI: 2.42%
1057 E Saint Catherine St Louisville , KY Charming updated home in Germantown! Nestled in one of Louisville's most desirable and est...	1 beds \| 1 baths \| 858 sq.ft.	$180,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $1047 Airbnb ROI: N/A Traditional ROI: 3.72%
8615 Battlefield Memorial Highway Berea , KY Outstanding rare find! Impressive foyer with sweeping grand staircase. Stunning hardwood t...	3 beds \| 3 baths \| 3,451 sq.ft.	$399,900	Airbnb cash on cash: 1.01% Traditional cash on cash: 1.77% Airbnb Rental Income: $1633 Traditional Rental Income: $1457 Airbnb ROI: 1.01% Traditional ROI: 1.77%
7797 Promontory Drive Alexandria , KY Incredible Fischer Clay loaded with upgrades! This beautiful multi-level floorplan offers ...	4 beds \| N/A baths \| 3,029 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.77% Airbnb Rental Income: $null Traditional Rental Income: $2254 Airbnb ROI: N/A Traditional ROI: 1.77%
11179 War Admiral Drive Union , KY Discover spacious luxury with this stunning home in the Equestrian section of Triple Crown...	5 beds \| 3 baths \| 3,160 sq.ft.	$614,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $2868 Airbnb ROI: N/A Traditional ROI: 3.26%
9218 Axminster Dr Louisville , KY Welcome to 9218 Axminster Drive! Tucked away at the end of a dead-end street in the Forest...	4 beds \| 3 baths \| 2,042 sq.ft.	$349,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 5.38% Airbnb Rental Income: $1634 Traditional Rental Income: $2483 Airbnb ROI: 1.38% Traditional ROI: 5.38%
1102 La Fontenay Ct Louisville , KY SELLER TO PAY FIRST 6 MONTHS OF HOA FEES!! Updated first floor condo in prime east end are...	2 beds \| 2 baths \| 1,000 sq.ft.	$129,900	Airbnb cash on cash: 4.53% Traditional cash on cash: 6.99% Airbnb Rental Income: $1295 Traditional Rental Income: $1197 Airbnb ROI: 4.53% Traditional ROI: 6.99%
816 Stratton Lane Winchester , KY Welcome to your dream home! Nestled in an excellent location in Winchester, KY, this charm...	4 beds \| 3 baths \| 3,024 sq.ft.	$250,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 9.42% Airbnb Rental Income: $1966 Traditional Rental Income: $2721 Airbnb ROI: 4.03% Traditional ROI: 9.42%

Real Estate investment in Windsor, KY

There are 0 properties for sale in the city of Windsor . The median list price in Windsor is $104,400 and the average price per square foot is $82. In September 2025, the average monthly cash on cash return in Windsor is 18.00%. The average monthly rental income in Windsor is $2,010.

Windsor, KY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 0 investment properties available for sale in Windsor.

The ROI for Short-Term is higher than the Long-Term in Windsor with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, KY

Other Investment Properties for Sale in Kentucky

Prospect , KY

4 beds | 4 baths | 4,218 sq.ft.

$479,900

Airbnb cash on cash: 4.6%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $4351

Traditional Rental Income: $3859

Airbnb ROI: 4.6%

Traditional ROI: 5.54%

Louisville , KY

4 beds | 3 baths | 4,087 sq.ft.

$559,900

Airbnb cash on cash: -0.78%

Traditional cash on cash: 2.54%

Airbnb Rental Income: $1115

Traditional Rental Income: $2481

Airbnb ROI: -0.78%

Traditional ROI: 2.54%

HODGENVILLE , KY

4 beds | 2 baths | 2,500 sq.ft.

$269,000

Airbnb cash on cash: 0.7%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $1115

Traditional Rental Income: $1766

Airbnb ROI: 0.7%

Traditional ROI: 4.74%

Elizabethtown , KY

3 beds | 1 baths | 1,170 sq.ft.

$194,900

Airbnb cash on cash: 2.65%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $1339

Traditional Rental Income: $1422

Airbnb ROI: 2.65%

Traditional ROI: 5.33%

Lexington , KY

3 beds | 3 baths | 1,582 sq.ft.

$249,000

Airbnb cash on cash: 3.28%

Traditional cash on cash: 4.95%

Airbnb Rental Income: $2032

Traditional Rental Income: $1898

Airbnb ROI: 3.28%

Traditional ROI: 4.95%

Louisville , KY

2 beds | 1 baths | 1,250 sq.ft.

$270,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.34%

Airbnb Rental Income: $null

Traditional Rental Income: $1415

Airbnb ROI: N/A

Traditional ROI: 3.34%

Louisville , KY

2 beds | 2 baths | 1,402 sq.ft.

$343,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.42%

Airbnb Rental Income: $null

Traditional Rental Income: $2070

Airbnb ROI: N/A

Traditional ROI: 2.42%

Louisville , KY

1 beds | 1 baths | 858 sq.ft.

$180,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.72%

Airbnb Rental Income: $null

Traditional Rental Income: $1047

Airbnb ROI: N/A

Traditional ROI: 3.72%

Berea , KY

3 beds | 3 baths | 3,451 sq.ft.

$399,900

Airbnb cash on cash: 1.01%

Traditional cash on cash: 1.77%

Airbnb Rental Income: $1633