Real Estate Investment Properties for Sale in Greensburg, KY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
115 S 2nd Street GREENSBURG, KY Welcome to this charming Folk Victorianâstyle home with three bedrooms and two full bath...	3 beds \| 2 baths \| 1,456 sq.ft.	$179,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 11.96% Airbnb Rental Income: $818 Traditional Rental Income: $2333 Airbnb ROI: 1.16% Traditional ROI: 11.96%
504 Milby Street GREENSBURG, KY Currenly pending with a contingency. Sellers can still take back up offers. Spacious and c...	4 beds \| 3 baths \| 2,480 sq.ft.	$280,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.32% Airbnb Rental Income: $null Traditional Rental Income: $2779 Airbnb ROI: N/A Traditional ROI: 8.32%
206 Penick Ave GREENSBURG, KY New listing! 206 Penick Ave. Greensburg. Check this one out! Lovely three bedroom, o...	3 beds \| 1 baths \| 1,320 sq.ft.	$175,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.4% Airbnb Rental Income: $818 Traditional Rental Income: $1134 Airbnb ROI: 0.55% Traditional ROI: 4.4%
107 N McCullum Avenue GREENSBURG, KY Welcome to 107 N McCullum Avenue! This 3-bedroom, 1-bathroom home sits on a manageable 0.0...	3 beds \| 1 baths \| 1,008 sq.ft.	$80,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 11.07% Airbnb Rental Income: $818 Traditional Rental Income: $1073 Airbnb ROI: 3.7% Traditional ROI: 11.07%
309 Campbellsville Road GREENSBURG, KY Step into timeless elegance with this beautifully restored 1900's historic home set on 4 s...	4 beds \| 3 baths \| 3,405 sq.ft.	$659,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.93% Airbnb Rental Income: $null Traditional Rental Income: $2652 Airbnb ROI: N/A Traditional ROI: 2.93%
113 Graham Court GREENSBURG, KY HISTORICAL BEAUTY! This unique John Barrett home was built in 1815 with 2872 sq feet and ...	3 beds \| 2 baths \| 2,872 sq.ft.	$419,900	Airbnb cash on cash: -0.26% Traditional cash on cash: 5.51% Airbnb Rental Income: $818 Traditional Rental Income: $2762 Airbnb ROI: -0.26% Traditional ROI: 5.51%
2930 Highway 1464 GREENSBURG, KY Cute Country Charmer! Welcome home to this cozy 2-bedroom, 1-bath gem tucked into a peacef...	2 beds \| 1 baths \| 936 sq.ft.	$140,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 9.72% Airbnb Rental Income: $1039 Traditional Rental Income: $1543 Airbnb ROI: 3.27% Traditional ROI: 9.72%
504 Cook Street GREENSBURG, KY "Primrose Cottage" in Greensburg, Kentucky. This charming, cozy, and adorable new construc...	2 beds \| 1 baths \| 825 sq.ft.	$168,500	Airbnb cash on cash: 2.56% Traditional cash on cash: 8.35% Airbnb Rental Income: $1039 Traditional Rental Income: $1607 Airbnb ROI: 2.56% Traditional ROI: 8.35%
302 Locust Street GREENSBURG, KY "Sweet Escape" Located in a quiet, friendly neighborhood just minutes from top-rated schoo...	2 beds \| 1 baths \| 1,800 sq.ft.	$199,500	Airbnb cash on cash: 1.23% Traditional cash on cash: 6.47% Airbnb Rental Income: $1039 Traditional Rental Income: $1669 Airbnb ROI: 1.23% Traditional ROI: 6.47%
417 Henry Street GREENSBURG, KY "Ivy Cottage" New Construction 3bedroom, 2bathroom home in the heart of downtown Greensbur...	3 beds \| 2 baths \| 1,200 sq.ft.	$235,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 6.45% Airbnb Rental Income: $818 Traditional Rental Income: $1938 Airbnb ROI: -0.05% Traditional ROI: 6.45%
1500 Mell Road GREENSBURG, KY Tucked away in total privacy, this unique berm-style home sits on 3.11 beautiful acres wit...	1 beds \| 2 baths \| 2,517 sq.ft.	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 10% Airbnb Rental Income: $null Traditional Rental Income: $2198 Airbnb ROI: N/A Traditional ROI: 10%
200 River Road GREENSBURG, KY **MOTIVATED SELLER** Charming 3-Bedroom Home in Charming Greensburg Neighborhood. Thi...	3 beds \| 2 baths \| 1,572 sq.ft.	$259,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 6.92% Airbnb Rental Income: $818 Traditional Rental Income: $2244 Airbnb ROI: -0.22% Traditional ROI: 6.92%
1266 Grassy Flat Road GREENSBURG, KY Tucked away at the end of a long gravel driveway, this well-maintained 3-bedroom, 3.5 bath...	3 beds \| 4 baths \| 2,780 sq.ft.	$430,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 6.92% Airbnb Rental Income: $818 Traditional Rental Income: $3382 Airbnb ROI: -0.25% Traditional ROI: 6.92%
796 Winding Ridge Road GREENSBURG, KY Charming Fixer-Upper on 8.84 Acres Embrace the potential of this unique fixer-upper! This...	3 beds \| 3 baths \| 1,800 sq.ft.	$259,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 8.32% Airbnb Rental Income: $818 Traditional Rental Income: $2580 Airbnb ROI: -0.22% Traditional ROI: 8.32%
110 Valley Drive GREENSBURG, KY Charming 4-Bedroom Home in Prime Location! Welcome to this inviting 4-bedroom, 1-bath home...	4 beds \| 1 baths \| 1,330 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.91% Airbnb Rental Income: $null Traditional Rental Income: $1962 Airbnb ROI: N/A Traditional ROI: 9.91%
181 Highway 88 GREENSBURG, KY Welcome to this Cozy home featuring a well designed main floor, perfect for comfortable li...	2 beds \| 1 baths \| 1,044 sq.ft.	$174,500	Airbnb cash on cash: 1.98% Traditional cash on cash: 7.4% Airbnb Rental Income: $1039 Traditional Rental Income: $1579 Airbnb ROI: 1.98% Traditional ROI: 7.4%
847 Locust Grove Rd GREENSBURG, KY Welcome to a rare opportunity to own 70 acres of versatile Kentucky land, perfect for thos...	4 beds \| 1 baths \| 1,635 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.23% Airbnb Rental Income: $null Traditional Rental Income: $1842 Airbnb ROI: N/A Traditional ROI: 4.23%
3120 Highway 1464 GREENSBURG, KY Looking for love in all the wrong places? Well, head on down Highway 1464 in Green County ...	2 beds \| 2 baths \| 1,332 sq.ft.	$189,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 9.23% Airbnb Rental Income: $1039 Traditional Rental Income: $1949 Airbnb ROI: 2.14% Traditional ROI: 9.23%
4419 Highway 1464 GREENSBURG, KY Charming 1-Bedroom Country Home on 0.8 Acres with Highway Frontage This beautifully update...	1 beds \| 1 baths \| 576 sq.ft.	$109,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.57% Airbnb Rental Income: $null Traditional Rental Income: $1238 Airbnb ROI: N/A Traditional ROI: 9.57%
403 Durham St GREENSBURG, KY New listing! For sale. 403 Durham St. Greensburg Ky. Charming Bedford stone ho...	2 beds \| 1 baths \| 1,022 sq.ft.	$125,000	Airbnb cash on cash: 3% Traditional cash on cash: 10.58% Airbnb Rental Income: $1039 Traditional Rental Income: $1590 Airbnb ROI: 3% Traditional ROI: 10.58%
92 Shirrell Cemetery Road GREENSBURG, KY Beautiful Mini Farm Retreat with Room to Roam â 3 Bed, 2.5 Bath on a Country Setting Dis...	4 beds \| 3 baths \| 1,672 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.45% Airbnb Rental Income: $null Traditional Rental Income: $1287 Airbnb ROI: N/A Traditional ROI: 2.45%

Real Estate investment in Greensburg, KY

There are 22 properties for sale in the city of Greensburg . The median list price in Greensburg is $180,000 and the average price per square foot is $113. In September 2025, the average monthly cash on cash return in Greensburg is 9.00%. The average monthly rental income in Greensburg is $1,956.

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

There are 22 investment properties available for sale in Greensburg.

In 2025, the best neighborhood to buy investment property is GREENSBURG.

The ROI for Long-Term is higher than the Short-Term in Greensburg with average rental income of $1,956.

Your search for investment property begins and ends here

Investment Property for Sale in Greensburg, KY

115 S 2nd Street

GREENSBURG, KY

3 beds | 2 baths | 1,456 sq.ft.

$179,000

Airbnb cash on cash: 1.16%

Traditional cash on cash: 11.96%

Airbnb Rental Income: $818

Traditional Rental Income: $2333

Airbnb ROI: 1.16%

Traditional ROI: 11.96%

504 Milby Street

GREENSBURG, KY

4 beds | 3 baths | 2,480 sq.ft.

$280,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.32%

Airbnb Rental Income: $null

Traditional Rental Income: $2779

Airbnb ROI: N/A

Traditional ROI: 8.32%

206 Penick Ave

GREENSBURG, KY

3 beds | 1 baths | 1,320 sq.ft.

$175,000

Airbnb cash on cash: 0.55%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $818

Traditional Rental Income: $1134

Airbnb ROI: 0.55%

Traditional ROI: 4.4%

107 N McCullum Avenue

GREENSBURG, KY

3 beds | 1 baths | 1,008 sq.ft.

$80,000

Airbnb cash on cash: 3.7%

Traditional cash on cash: 11.07%

Airbnb Rental Income: $818

Traditional Rental Income: $1073

Airbnb ROI: 3.7%

Traditional ROI: 11.07%

309 Campbellsville Road

GREENSBURG, KY

4 beds | 3 baths | 3,405 sq.ft.

$659,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.93%

Airbnb Rental Income: $null

Traditional Rental Income: $2652

Airbnb ROI: N/A

Traditional ROI: 2.93%

113 Graham Court

GREENSBURG, KY

3 beds | 2 baths | 2,872 sq.ft.

$419,900

Airbnb cash on cash: -0.26%

Traditional cash on cash: 5.51%

Airbnb Rental Income: $818

Traditional Rental Income: $2762

Airbnb ROI: -0.26%

Traditional ROI: 5.51%

2930 Highway 1464

GREENSBURG, KY

2 beds | 1 baths | 936 sq.ft.

$140,000

Airbnb cash on cash: 3.27%

Traditional cash on cash: 9.72%

Airbnb Rental Income: $1039

Traditional Rental Income: $1543

Airbnb ROI: 3.27%

Traditional ROI: 9.72%

504 Cook Street

GREENSBURG, KY

2 beds | 1 baths | 825 sq.ft.

$168,500

Airbnb cash on cash: 2.56%

Traditional cash on cash: 8.35%

Airbnb Rental Income: $1039

Traditional Rental Income: $1607

Airbnb ROI: 2.56%