Real Estate Investment Properties for Sale in Greenwood, IN

Looking for investment property in Greenwood, IN with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
848 Cypress N Greenwood, IN From the moment you pull up, this all-brick ranch just feels like home. It's warm, welcomi...	3 beds \| 2 baths \| 1,608 sq.ft.	$315,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 4.79% Airbnb Rental Income: $1459 Traditional Rental Income: $1942 Airbnb ROI: 1.7% Traditional ROI: 4.79%
400 W Main Street Greenwood, IN Unlock the lifestyle you've been waiting for! Imagine a Saturday night where you leave the...	3 beds \| 2 baths \| 2,062 sq.ft.	$300,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 5.75% Airbnb Rental Income: $1459 Traditional Rental Income: $2105 Airbnb ROI: 1.93% Traditional ROI: 5.75%
1272 Townsend Drive Greenwood, IN Tucked on a spacious corner lot, this 3-bedroom, 2.5-bath home is truly move-in ready with...	3 beds \| 3 baths \| 2,036 sq.ft.	$309,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 5.91% Airbnb Rental Income: $1459 Traditional Rental Income: $2302 Airbnb ROI: 1.54% Traditional ROI: 5.91%
2596 Horizon Boulevard Greenwood, IN Welcome home to this Charming 3-bedroom, 2.5-bath ranch on a large fenced-in yard with mat...	3 beds \| 3 baths \| 1,443 sq.ft.	$314,900	Airbnb cash on cash: 1.73% Traditional cash on cash: 4.67% Airbnb Rental Income: $1459 Traditional Rental Income: $1897 Airbnb ROI: 1.73% Traditional ROI: 4.67%
1737 Brer Rabbit Drive Greenwood, IN Beautiful 1531 sq ft stone ranch, move-in ready! Great location, nestled on over 1/2 an ac...	3 beds \| 2 baths \| 1,531 sq.ft.	$299,900	Airbnb cash on cash: 2.03% Traditional cash on cash: 5.05% Airbnb Rental Income: $1459 Traditional Rental Income: $1881 Airbnb ROI: 2.03% Traditional ROI: 5.05%
2545 Wildflower Lane Greenwood, IN Welcome to this beautiful, well-maintained home offering spacious living in a prime locati...	4 beds \| 3 baths \| 2,793 sq.ft.	$334,900	Airbnb cash on cash: 2.41% Traditional cash on cash: 6.68% Airbnb Rental Income: $1884 Traditional Rental Income: $2723 Airbnb ROI: 2.41% Traditional ROI: 6.68%
5862 Columbia Circle Greenwood, IN Ready to FIND the space you have been waiting for? This home will CHECK all your boxes. Lo...	4 beds \| 3 baths \| 2,295 sq.ft.	$345,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 5.64% Airbnb Rental Income: $1884 Traditional Rental Income: $2396 Airbnb ROI: 2.51% Traditional ROI: 5.64%
6451 Enclave Court Greenwood, IN This home has been freshly updated and is ready for your family! It sits in the popular En...	4 beds \| 3 baths \| 2,642 sq.ft.	$349,995	Airbnb cash on cash: 2.31% Traditional cash on cash: 6.07% Airbnb Rental Income: $1884 Traditional Rental Income: $2617 Airbnb ROI: 2.31% Traditional ROI: 6.07%
4498 Hickory Grove Boulevard Greenwood, IN This all BRICK, one level home with a FINISHED walk-out basement is perfectly POSITIONED a...	4 beds \| 4 baths \| 5,080 sq.ft.	$680,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.99% Airbnb Rental Income: $1884 Traditional Rental Income: $1820 Airbnb ROI: 0.29% Traditional ROI: 0.99%
2209 Leeward Court Greenwood, IN This beautiful 3-bedroom, 2-bath ranch home in desirable Greenwood, IN offers the perfect ...	3 beds \| 2 baths \| 1,518 sq.ft.	$304,500	Airbnb cash on cash: 1.81% Traditional cash on cash: 4.75% Airbnb Rental Income: $1459 Traditional Rental Income: $1867 Airbnb ROI: 1.81% Traditional ROI: 4.75%
1418 Osprey Way Greenwood, IN Downstairs has a bedroom across its own full bath. Garden tub and 2 large walk in closets...	5 beds \| 3 baths \| 2,986 sq.ft.	$299,890	Airbnb cash on cash: N/A Traditional cash on cash: 7.71% Airbnb Rental Income: $null Traditional Rental Income: $2725 Airbnb ROI: N/A Traditional ROI: 7.71%
2777 Grand Fir Drive Greenwood, IN Hold onto your hats, folks, 2777 Grand Fir Dr is ready to steal your heart (and your keys)...	3 beds \| 3 baths \| 1,677 sq.ft.	$239,900	Airbnb cash on cash: 2.72% Traditional cash on cash: 5.25% Airbnb Rental Income: $1459 Traditional Rental Income: $1600 Airbnb ROI: 2.72% Traditional ROI: 5.25%
2019 Woodfield Drive Greenwood, IN Nestled at 2019 Woodfield DR, GREENWOOD, IN, this attractive property in Johnson County of...	3 beds \| 3 baths \| 2,934 sq.ft.	$450,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 3.92% Airbnb Rental Income: $1459 Traditional Rental Income: $2438 Airbnb ROI: 0.58% Traditional ROI: 3.92%
451 Pebble Way Greenwood, IN Come take a look at this full brick ranch home in Center Grove! It has a large open living...	3 beds \| 2 baths \| 1,285 sq.ft.	$295,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.92% Airbnb Rental Income: $1459 Traditional Rental Income: $1708 Airbnb ROI: 1.47% Traditional ROI: 3.92%
1697 Pelham Drive Greenwood, IN Welcome to this beautiful 2021 built home in Fieldstone Subdivision, featuring 3 bedroom 2...	3 beds \| 3 baths \| 2,463 sq.ft.	$434,500	Airbnb cash on cash: 0.29% Traditional cash on cash: 4.14% Airbnb Rental Income: $1459 Traditional Rental Income: $2592 Airbnb ROI: 0.29% Traditional ROI: 4.14%
1758 Pelham Drive Greenwood, IN Step inside this thoughtfully designed ranch home located in the popular Fieldstone neighb...	3 beds \| 3 baths \| 2,182 sq.ft.	$415,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 2.5% Airbnb Rental Income: $1459 Traditional Rental Income: $1852 Airbnb ROI: 0.37% Traditional ROI: 2.5%
1512 Tuscany Drive Greenwood, IN Beautiful 4-bedroom, 3.5-bath open-concept home in Greenwood! This spacious layout feature...	4 beds \| 4 baths \| 4,008 sq.ft.	$589,900	Airbnb cash on cash: 0.71% Traditional cash on cash: 2.45% Airbnb Rental Income: $1884 Traditional Rental Income: $2341 Airbnb ROI: 0.71% Traditional ROI: 2.45%
5151 W Stones Crossing Road Greenwood, IN MAGNIFICENT 5 Bedroom / 2.5 Bath Full Brick Ranch w/ Finished Basement on 1.3 Acres AVAILA...	5 beds \| 3 baths \| 4,250 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $2289 Airbnb ROI: N/A Traditional ROI: 1.71%
2950 Treehouse Pass Greenwood, IN Great Two Story House in Greenwood with a full fenced back yard and deck waiting for you t...	3 beds \| 3 baths \| 2,132 sq.ft.	$317,500	Airbnb cash on cash: 1.34% Traditional cash on cash: 5.72% Airbnb Rental Income: $1459 Traditional Rental Income: $2333 Airbnb ROI: 1.34% Traditional ROI: 5.72%
317 Legacy Boulevard Greenwood, IN Spacious 4 bedroom, 2.5 bathroom home in Greenwood featuring a full unfinished basement, v...	4 beds \| 3 baths \| 3,085 sq.ft.	$349,900	Airbnb cash on cash: 2.19% Traditional cash on cash: 5.99% Airbnb Rental Income: $1884 Traditional Rental Income: $2631 Airbnb ROI: 2.19% Traditional ROI: 5.99%
948 Fred Lane Greenwood, IN Move in Ready w/ Immediate possession. Attractive 2023 Built, Brick Ranch 3 BR/2.5 BA home...	3 beds \| 3 baths \| 2,187 sq.ft.	$435,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.87% Airbnb Rental Income: $1459 Traditional Rental Income: $2049 Airbnb ROI: 0.36% Traditional ROI: 2.87%
2967 Hearthside Drive Greenwood, IN Outstanding Opportunity in Homecoming at University Park! Welcome to this beautiful 3-bedr...	3 beds \| 3 baths \| 2,398 sq.ft.	$324,900	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.66% Airbnb Rental Income: $1459 Traditional Rental Income: $1808 Airbnb ROI: 1.1% Traditional ROI: 3.66%
733 Keepsake Run Greenwood, IN Rare 2017 Build with Finished Basement in Greenwood! This 4-bed, 2.5-bath home offers 3,5...	4 beds \| 3 baths \| 3,524 sq.ft.	$395,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 4% Airbnb Rental Income: $1884 Traditional Rental Income: $2290 Airbnb ROI: 1.55% Traditional ROI: 4%
1567 Mitis Street Greenwood, IN Welcome to this beautifully crafted 3-bedroom, 2-bath ranch home offering timeless Craftsm...	3 beds \| 2 baths \| 1,673 sq.ft.	$325,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.7% Airbnb Rental Income: $1459 Traditional Rental Income: $1869 Airbnb ROI: 0.95% Traditional ROI: 3.7%
5656 Grosbeak Drive Greenwood, IN MI Homes built this beautiful Fairbanks floor plan home in 2021. This home is like new ins...	4 beds \| 3 baths \| 2,976 sq.ft.	$429,500	Airbnb cash on cash: 1.23% Traditional cash on cash: 4% Airbnb Rental Income: $1884 Traditional Rental Income: $2495 Airbnb ROI: 1.23% Traditional ROI: 4%
142 Kensington Park Road Greenwood, IN SPACE ODESSEY!!! Enjoy all of the space that this 3 bedroom (poss 4), 2 bath brick ranch ...	3 beds \| 2 baths \| 1,521 sq.ft.	$225,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 7.38% Airbnb Rental Income: $1459 Traditional Rental Income: $1995 Airbnb ROI: 2.83% Traditional ROI: 7.38%
2277 Maple Stone Lane Greenwood, IN Cherry Tree Walk Beautiful 5 BEDROOM + 2.5 BATH Two-Story Home! 3,068 Sq. Ft. Features: ...	5 beds \| 3 baths \| 3,068 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.69% Airbnb Rental Income: $null Traditional Rental Income: $2949 Airbnb ROI: N/A Traditional ROI: 5.69%
1 S Meridian Street Greenwood, IN Welcome to 2026 in the heart of Old Town Greenwood-where classic charm meets modern style....	4 beds \| 3 baths \| 2,102 sq.ft.	$310,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 4.36% Airbnb Rental Income: $1884 Traditional Rental Income: $1784 Airbnb ROI: 2.98% Traditional ROI: 4.36%
801 Silverleaf Drive Greenwood, IN Located at 801 Silverleaf DR, GREENWOOD, IN, this attractive single-family residence in Jo...	4 beds \| 4 baths \| 5,679 sq.ft.	$765,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 2.97% Airbnb Rental Income: $1884 Traditional Rental Income: $3467 Airbnb ROI: 0.05% Traditional ROI: 2.97%
3621 Olive Branch Road Greenwood, IN Adjacent to Dyes Walk Golf Course, luxury, privacy, and flexibility come together in this ...	5 beds \| 6 baths \| 7,454 sq.ft.	$1,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.28% Airbnb Rental Income: $null Traditional Rental Income: $7191 Airbnb ROI: N/A Traditional ROI: 3.28%
1169 Richmond Lane Greenwood, IN Lovely, well-maintained 5 BR home on 1/3 acre lot in sought-after community with pool & pl...	5 beds \| 3 baths \| 2,560 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.69% Airbnb Rental Income: $null Traditional Rental Income: $2546 Airbnb ROI: N/A Traditional ROI: 4.69%
1265 Sika Lane Greenwood, IN This is Lennar's incredibly popular Rockwell D floorplan! This wonderful home features a g...	5 beds \| 5 baths \| 3,529 sq.ft.	$486,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.73% Airbnb Rental Income: $null Traditional Rental Income: $4714 Airbnb ROI: N/A Traditional ROI: 8.73%
17 Crestview Drive Greenwood, IN Come see this charming home now on the market! Discover a bright interior tied together w...	3 beds \| 2 baths \| 1,721 sq.ft.	$240,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 6.38% Airbnb Rental Income: $1459 Traditional Rental Income: $1920 Airbnb ROI: 2.45% Traditional ROI: 6.38%
5839 Altar Bell Circle Greenwood, IN Corner Lot Beauty Built in 2023! Welcome home to modern luxury on a premium corner lot! Th...	5 beds \| 3 baths \| 3,371 sq.ft.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $2848 Airbnb ROI: N/A Traditional ROI: 5.01%
209 Brighton Court Greenwood, IN Check out this stunning condo, located next to the Valle Vista Golf Course in Greenwood, f...	2 beds \| 2 baths \| 1,314 sq.ft.	$228,200	Airbnb cash on cash: -0.34% Traditional cash on cash: 3.17% Airbnb Rental Income: $1189 Traditional Rental Income: $1560 Airbnb ROI: -0.34% Traditional ROI: 3.17%
5331 Birch Lane Greenwood, IN Dive into Your Private Oasis Experience the epitome of relaxation and entertainment with ...	3 beds \| 2 baths \| 1,751 sq.ft.	$385,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 3.79% Airbnb Rental Income: $1459 Traditional Rental Income: $2244 Airbnb ROI: 0.42% Traditional ROI: 3.79%
1021 Hudson Bay Drive Greenwood, IN Custom-Built and Well-Appointed Ranch w/ Walk-Out Daylight Basement and Beautiful Living A...	5 beds \| 5 baths \| 4,680 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.55% Airbnb Rental Income: $null Traditional Rental Income: $4847 Airbnb ROI: N/A Traditional ROI: 7.55%
4808 Lakeview Drive Greenwood, IN Why wait two years to design and build your next custom home when you can step into this s...	4 beds \| 6 baths \| 4,764 sq.ft.	$1,050,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 4.92% Airbnb Rental Income: $1884 Traditional Rental Income: $6883 Airbnb ROI: -0.71% Traditional ROI: 4.92%
4242 Watson Road Greenwood, IN Nestled behind a private stone entry gate on 5 wooded, meticulously landscaped acres, this...	4 beds \| 5 baths \| 5,779 sq.ft.	$2,500,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 0.28% Airbnb Rental Income: $1884 Traditional Rental Income: $4951 Airbnb ROI: -1.26% Traditional ROI: 0.28%
1148 Easy Street #A Greenwood, IN Your proposed all-brick, single-family attached home will feature 3 bedrooms, 2 full baths...	3 beds \| 2 baths \| 1,578 sq.ft.	$380,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 4.01% Airbnb Rental Income: $1459 Traditional Rental Income: $2084 Airbnb ROI: 1.04% Traditional ROI: 4.01%

Real Estate investment in Greenwood, IN

There are 154 properties for sale in the city of Greenwood . The median list price in Greenwood is $353,500 and the average price per square foot is $141. In January 2026, the average monthly cash on cash return in Greenwood is 5.00%. The average monthly rental income in Greenwood is $2,281.

Greenwood, IN Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 154 investment properties available for sale in Greenwood.

In 2026, the best neighborhood to buy investment property is Greenwood.

The ROI for Long-Term is higher than the Short-Term in Greenwood with average rental income of $2,281.

Your search for investment property begins and ends here

Investment Property for Sale in Greenwood, IN

848 Cypress N

Greenwood, IN

3 beds | 2 baths | 1,608 sq.ft.

$315,000

Airbnb cash on cash: 1.7%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $1459

Traditional Rental Income: $1942

Airbnb ROI: 1.7%

Traditional ROI: 4.79%

400 W Main Street

Greenwood, IN

3 beds | 2 baths | 2,062 sq.ft.

$300,000

Airbnb cash on cash: 1.93%

Traditional cash on cash: 5.75%

Airbnb Rental Income: $1459

Traditional Rental Income: $2105

Airbnb ROI: 1.93%

Traditional ROI: 5.75%

1272 Townsend Drive

Greenwood, IN

3 beds | 3 baths | 2,036 sq.ft.

$309,900

Airbnb cash on cash: 1.54%

Traditional cash on cash: 5.91%

Airbnb Rental Income: $1459

Traditional Rental Income: $2302

Airbnb ROI: 1.54%

Traditional ROI: 5.91%

2596 Horizon Boulevard

Greenwood, IN

3 beds | 3 baths | 1,443 sq.ft.

$314,900

Airbnb cash on cash: 1.73%

Traditional cash on cash: 4.67%

Airbnb Rental Income: $1459

Traditional Rental Income: $1897

Airbnb ROI: 1.73%

Traditional ROI: 4.67%

1737 Brer Rabbit Drive

Greenwood, IN

3 beds | 2 baths | 1,531 sq.ft.

$299,900

Airbnb cash on cash: 2.03%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $1459

Traditional Rental Income: $1881

Airbnb ROI: 2.03%

Traditional ROI: 5.05%

2545 Wildflower Lane

Greenwood, IN

4 beds | 3 baths | 2,793 sq.ft.

$334,900

Airbnb cash on cash: 2.41%

Traditional cash on cash: 6.68%

Airbnb Rental Income: $1884

Traditional Rental Income: $2723

Airbnb ROI: 2.41%

Traditional ROI: 6.68%

5862 Columbia Circle

Greenwood, IN

4 beds | 3 baths | 2,295 sq.ft.

$345,000

Airbnb cash on cash: 2.51%

Traditional cash on cash: 5.64%

Airbnb Rental Income: $1884

Traditional Rental Income: $2396

Airbnb ROI: 2.51%

Traditional ROI: 5.64%

6451 Enclave Court

Greenwood, IN

4 beds | 3 baths | 2,642 sq.ft.

$349,995

Airbnb cash on cash: 2.31%

Traditional cash on cash: 6.07%

Airbnb Rental Income: $1884

Traditional Rental Income: $2617

Airbnb ROI: 2.31%