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
387 Pleasantview Boulevard Greenwood, IN Welcome Home! This home is located on cul-de-sac near the Greenwood Carefree Community and...	3 beds \| 2 baths \| 1,564 sq.ft.	$295,900	Airbnb cash on cash: 3.48% Traditional cash on cash: 5.04% Airbnb Rental Income: $1946 Traditional Rental Income: $1867 Airbnb ROI: 3.48% Traditional ROI: 5.04%
5415 Misthaven Lane Greenwood, IN Welcome to this really comfortable home in Brookhaven that just feels easy to live in. The...	4 beds \| 3 baths \| 2,428 sq.ft.	$375,000	Airbnb cash on cash: 2.75% Traditional cash on cash: 5.11% Airbnb Rental Income: $2177 Traditional Rental Income: $2456 Airbnb ROI: 2.75% Traditional ROI: 5.11%
2689 Falcon Drive Greenwood, IN Welcome home to this beautiful 2,167 square foot two-story nestled on a corner lot in the ...	4 beds \| 3 baths \| 2,167 sq.ft.	$350,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 5.79% Airbnb Rental Income: $2177 Traditional Rental Income: $2417 Airbnb ROI: 3.39% Traditional ROI: 5.79%
1144 Barbara Drive Greenwood, IN Discover the charm of single-story living at 1144 Barbara DR, a delightful single-family r...	2 beds \| 1 baths \| 1,013 sq.ft.	$204,999	Airbnb cash on cash: 4.07% Traditional cash on cash: 4.15% Airbnb Rental Income: $1574 Traditional Rental Income: $1138 Airbnb ROI: 4.07% Traditional ROI: 4.15%
5263 Brooks Bend Greenwood, IN Beautiful custom-built, three-level home in the heart of Center Grove. Sought after Preser...	4 beds \| 4 baths \| 3,725 sq.ft.	$505,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 5.15% Airbnb Rental Income: $2177 Traditional Rental Income: $3284 Airbnb ROI: 1.63% Traditional ROI: 5.15%
5422 Wakefield Drive S Greenwood, IN You will love this 4-bedroom Wakefield home minutes away from the pond where you can fish ...	4 beds \| 4 baths \| 4,452 sq.ft.	$400,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 7.29% Airbnb Rental Income: $2177 Traditional Rental Income: $3414 Airbnb ROI: 2.52% Traditional ROI: 7.29%
5400 Wakefield Drive S Greenwood, IN Bring your strongest offer - seller is offering up to $2,500 toward buyers concessions. Di...	4 beds \| 3 baths \| 3,894 sq.ft.	$395,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 5.29% Airbnb Rental Income: $2177 Traditional Rental Income: $2571 Airbnb ROI: 2.74% Traditional ROI: 5.29%
229 Brighton Court Greenwood, IN Welcome home to this magnificently modern and maintenance-free 3 bed, 2.5 bath condo locat...	3 beds \| 3 baths \| 1,844 sq.ft.	$300,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 5.07% Airbnb Rental Income: $1946 Traditional Rental Income: $2312 Airbnb ROI: 1.95% Traditional ROI: 5.07%
759 Mountain Pine Drive Greenwood, IN Welcome to 759 Mountain Pine Dr. in Greenwood, where comfort, style, and functionality com...	3 beds \| 3 baths \| 1,697 sq.ft.	$254,999	Airbnb cash on cash: 3.88% Traditional cash on cash: 5.97% Airbnb Rental Income: $1946 Traditional Rental Income: $1935 Airbnb ROI: 3.88% Traditional ROI: 5.97%
299 Entrance Hall View Greenwood, IN This is the one you've been waiting for. This stunning Center Grove luxury ranch sits on a...	3 beds \| 2 baths \| 2,299 sq.ft.	$454,900	Airbnb cash on cash: 1.56% Traditional cash on cash: 3.54% Airbnb Rental Income: $1946 Traditional Rental Income: $2277 Airbnb ROI: 1.56% Traditional ROI: 3.54%
5590 Harness Drive Greenwood, IN This is a rare opportunity to skip the process of building new without sacrificing quality...	4 beds \| 5 baths \| 4,912 sq.ft.	$850,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 4.26% Airbnb Rental Income: $2177 Traditional Rental Income: $4520 Airbnb ROI: 0.61% Traditional ROI: 4.26%
1500 Harrison Drive Greenwood, IN Enjoy the ease of one-level living in this beautifully updated 3-bedroom, 2-bath ranch hom...	3 beds \| 2 baths \| 1,316 sq.ft.	$275,000	Airbnb cash on cash: 3.54% Traditional cash on cash: 6.32% Airbnb Rental Income: $1946 Traditional Rental Income: $2155 Airbnb ROI: 3.54% Traditional ROI: 6.32%
298 Pennswood Road Greenwood, IN Scenic nature and water views just beyond the fully fenced backyard of this 4 bedroom, 2.5...	4 beds \| 3 baths \| 3,284 sq.ft.	$425,000	Airbnb cash on cash: 2.32% Traditional cash on cash: 3.13% Airbnb Rental Income: $2177 Traditional Rental Income: $1948 Airbnb ROI: 2.32% Traditional ROI: 3.13%
458 Sayre Drive Greenwood, IN Cozy 3 beds 1.5 baths ranch home in greenwood area awaits new owner ! All laminate hardwoo...	3 beds \| 2 baths \| 1,068 sq.ft.	$220,000	Airbnb cash on cash: 5.38% Traditional cash on cash: 5.75% Airbnb Rental Income: $1946 Traditional Rental Income: $1510 Airbnb ROI: 5.38% Traditional ROI: 5.75%
700 Horton Street Greenwood, IN Welcome home to this charming all brick 3 BR, 2FBA home of yesteryear! this sweet home bod...	3 beds \| 2 baths \| 1,628 sq.ft.	$279,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 5.38% Airbnb Rental Income: $1946 Traditional Rental Income: $1964 Airbnb ROI: 3.36% Traditional ROI: 5.38%
863 W Ashbourne Lane Greenwood, IN Immaculate and meticulously maintained 3-bedroom, 2-bath ranch home nestled in the heart o...	3 beds \| 2 baths \| 1,848 sq.ft.	$339,900	Airbnb cash on cash: 2.75% Traditional cash on cash: 4.64% Airbnb Rental Income: $1946 Traditional Rental Income: $2035 Airbnb ROI: 2.75% Traditional ROI: 4.64%
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 \| 2,379 sq.ft.	$335,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 5.83% Airbnb Rental Income: $2177 Traditional Rental Income: $2396 Airbnb ROI: 3.39% Traditional ROI: 5.83%
1215 Siena Drive Greenwood, IN Welcome to this charming 2-story home in the sought-after Tuscany Village neighborhood in ...	4 beds \| 3 baths \| 2,770 sq.ft.	$399,900	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.08% Airbnb Rental Income: $2177 Traditional Rental Income: $2586 Airbnb ROI: 2.52% Traditional ROI: 5.08%
3442 Enclave Lane Greenwood, IN Welcome Home! This 3 bed, 2 bath ranch features a split floor plan, cathedral ceilings, an...	3 beds \| 2 baths \| 1,390 sq.ft.	$290,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.44% Airbnb Rental Income: $1946 Traditional Rental Income: $1743 Airbnb ROI: 3.3% Traditional ROI: 4.44%
1770 Blue Grass Parkway Greenwood, IN Welcome home to this spacious and inviting 3-bedroom, 2.5-bath residence in desirable Gree...	3 beds \| 3 baths \| 2,226 sq.ft.	$274,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 6.22% Airbnb Rental Income: $1946 Traditional Rental Income: $2273 Airbnb ROI: 2.97% Traditional ROI: 6.22%
4047 N Oval Lane Greenwood, IN Welcome to 4047 N Oval Lane in Greenwood, located in the popular Enclave at Harrison Cross...	3 beds \| 2 baths \| 1,938 sq.ft.	$380,000	Airbnb cash on cash: 2.16% Traditional cash on cash: 4.27% Airbnb Rental Income: $1946 Traditional Rental Income: $2186 Airbnb ROI: 2.16% Traditional ROI: 4.27%
5326 Tracey Jo Road Greenwood, IN Fully renovated, stunning custom brick ranch in Center Grove schools. Sought-after neighbo...	4 beds \| 3 baths \| 2,614 sq.ft.	$400,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 5.28% Airbnb Rental Income: $2177 Traditional Rental Income: $2604 Airbnb ROI: 2.67% Traditional ROI: 5.28%
525 Paradise Way E #C Greenwood, IN Welcome to 525 Paradise Way E (Unit C)! Fall in love with this low-maintenance, move-in-re...	2 beds \| 2 baths \| 1,270 sq.ft.	$185,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 5.61% Airbnb Rental Income: $1574 Traditional Rental Income: $1558 Airbnb ROI: 3.13% Traditional ROI: 5.61%
1708 Woodcroft Court Greenwood, IN PRICED TO IMPRESS, this home delivers exceptional VALUE. To make ownership even more attai...	4 beds \| 5 baths \| 4,588 sq.ft.	$599,900	Airbnb cash on cash: 1.16% Traditional cash on cash: 6.52% Airbnb Rental Income: $2177 Traditional Rental Income: $4627 Airbnb ROI: 1.16% Traditional ROI: 6.52%
4748 Brickert Court Greenwood, IN Welcome to this beautifully designed home offering over 4,100 total square feet, 3-car gar...	3 beds \| 3 baths \| 2,958 sq.ft.	$455,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 3.96% Airbnb Rental Income: $1946 Traditional Rental Income: $2625 Airbnb ROI: 1.16% Traditional ROI: 3.96%
225 Southwind Way Greenwood, IN Made for Memories! Situated on one of the largest lots in Southwind Estates (over 1/2 acre...	4 beds \| 3 baths \| 2,172 sq.ft.	$469,999	Airbnb cash on cash: 1.96% Traditional cash on cash: 3.87% Airbnb Rental Income: $2177 Traditional Rental Income: $2464 Airbnb ROI: 1.96% Traditional ROI: 3.87%
3463 Enclave Lane Greenwood, IN The neighbors of 3463 Enclave Ln are waiting for you! Welcome home to this inviting 3-bedr...	3 beds \| 2 baths \| 1,636 sq.ft.	$299,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 4.78% Airbnb Rental Income: $1946 Traditional Rental Income: $1883 Airbnb ROI: 3.18% Traditional ROI: 4.78%
449 Southgate Drive Greenwood, IN Welcome Home to this 3BR, 1BA stone ranch in the heart of Greenwood! This home offers an u...	3 beds \| 1 baths \| 960 sq.ft.	$229,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 4.94% Airbnb Rental Income: $1946 Traditional Rental Income: $1425 Airbnb ROI: 4.98% Traditional ROI: 4.94%
1200 Timber Creek Lane Greenwood, IN Move in ready with immediate possession and built in equity, this updated 3BR/2BA ranch st...	3 beds \| 2 baths \| 1,228 sq.ft.	$215,000	Airbnb cash on cash: 4.19% Traditional cash on cash: 4.87% Airbnb Rental Income: $1946 Traditional Rental Income: $1572 Airbnb ROI: 4.19% Traditional ROI: 4.87%
1795 Feather Reed Lane Greenwood, IN Welcome to your new home! As you enter through the covered porch, you walk into a spacious...	3 beds \| 3 baths \| 2,328 sq.ft.	$289,900	Airbnb cash on cash: 3.34% Traditional cash on cash: 6.43% Airbnb Rental Income: $1946 Traditional Rental Income: $2275 Airbnb ROI: 3.34% Traditional ROI: 6.43%
1772 Wedgewood Drive Greenwood, IN Update: Motivated Seller!!!! Seller is offering $5,000 in sellers concessions to buyers wi...	4 beds \| 5 baths \| 4,127 sq.ft.	$674,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 6.44% Airbnb Rental Income: $2177 Traditional Rental Income: $5110 Airbnb ROI: 0.89% Traditional ROI: 6.44%
1167 Station Drive Greenwood, IN Discover an exceptional lifestyle opportunity at 1167 Station DR, GREENWOOD. Constructed i...	4 beds \| 3 baths \| 2,218 sq.ft.	$339,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 5.61% Airbnb Rental Income: $2177 Traditional Rental Income: $2411 Airbnb ROI: 3.14% Traditional ROI: 5.61%
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.	$420,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 4.17% Airbnb Rental Income: $1946 Traditional Rental Income: $2438 Airbnb ROI: 1.62% Traditional ROI: 4.17%
1697 Pelham Drive Greenwood, IN Welcome to this ALL-BRICK, MOVE-IN ready ranch-style home that immediately feels solid, co...	3 beds \| 3 baths \| 2,463 sq.ft.	$430,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 4.2% Airbnb Rental Income: $1946 Traditional Rental Income: $2592 Airbnb ROI: 1.32% Traditional ROI: 4.2%
884 Sheffield Drive Greenwood, IN Turnkey and move-in ready, this beautifully updated home awaits its next homeowner! Locate...	3 beds \| 3 baths \| 1,486 sq.ft.	$300,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 5.06% Airbnb Rental Income: $1946 Traditional Rental Income: $1897 Airbnb ROI: 3.41% Traditional ROI: 5.06%
1758 Pelham Drive Greenwood, IN Modern ranch living with pond views - HUGE LOT - PRICE REDUCED Built in 2022, this move in...	3 beds \| 3 baths \| 2,182 sq.ft.	$399,900	Airbnb cash on cash: 1.54% Traditional cash on cash: 2.66% Airbnb Rental Income: $1946 Traditional Rental Income: $1852 Airbnb ROI: 1.54% Traditional ROI: 2.66%
1355 Egret Lane Greenwood, IN Tastefully updated and easy to love, this traditional 3-bedroom, 2.5-bath home offers a la...	3 beds \| 3 baths \| 2,050 sq.ft.	$285,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 6.57% Airbnb Rental Income: $1946 Traditional Rental Income: $2284 Airbnb ROI: 3.4% Traditional ROI: 6.57%
81 Crestview Drive Greenwood, IN Discover 81 Crestview DR in GREENWOOD, IN, a 1960 ranch-style single family residence offe...	4 beds \| 1 baths \| 1,248 sq.ft.	$177,000	Airbnb cash on cash: 7.02% Traditional cash on cash: 6.14% Airbnb Rental Income: $2177 Traditional Rental Income: $1477 Airbnb ROI: 7.02% Traditional ROI: 6.14%
1132 Madrid Road Greenwood, IN Tucked into one of Greenwood's most ESTABLISHED and sought-after neighborhoods. The main l...	4 beds \| 2 baths \| 2,324 sq.ft.	$340,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 5.29% Airbnb Rental Income: $2177 Traditional Rental Income: $2298 Airbnb ROI: 3.18% Traditional ROI: 5.29%
310 S Serenity Way Greenwood, IN Space, layout, and location come together in this 4-bedroom, 2.5-bath home in the desirabl...	4 beds \| 3 baths \| 1,959 sq.ft.	$323,000	Airbnb cash on cash: 3.57% Traditional cash on cash: 6% Airbnb Rental Income: $2177 Traditional Rental Income: $2363 Airbnb ROI: 3.57% Traditional ROI: 6%

Real Estate investment in Greenwood, IN

There are 201 properties for sale in the city of Greenwood . The median list price in Greenwood is $294,824 and the average price per square foot is $117. In July 2026, the average monthly cash on cash return in Greenwood is 5.00%. The average monthly rental income in Greenwood is $2,364.

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

There are 201 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 $2,364.

Your search for investment property begins and ends here

Investment Property for Sale in Greenwood, IN

387 Pleasantview Boulevard

Greenwood, IN

3 beds | 2 baths | 1,564 sq.ft.

$295,900

Airbnb cash on cash: 3.48%

Traditional cash on cash: 5.04%

Airbnb Rental Income: $1946

Traditional Rental Income: $1867

Airbnb ROI: 3.48%

Traditional ROI: 5.04%

5415 Misthaven Lane

Greenwood, IN

4 beds | 3 baths | 2,428 sq.ft.

$375,000

Airbnb cash on cash: 2.75%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $2177

Traditional Rental Income: $2456

Airbnb ROI: 2.75%

Traditional ROI: 5.11%

2689 Falcon Drive

Greenwood, IN

4 beds | 3 baths | 2,167 sq.ft.

$350,000

Airbnb cash on cash: 3.39%

Traditional cash on cash: 5.79%

Airbnb Rental Income: $2177

Traditional Rental Income: $2417

Airbnb ROI: 3.39%

Traditional ROI: 5.79%

1144 Barbara Drive

Greenwood, IN

2 beds | 1 baths | 1,013 sq.ft.

$204,999

Airbnb cash on cash: 4.07%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $1574

Traditional Rental Income: $1138

Airbnb ROI: 4.07%

Traditional ROI: 4.15%

5263 Brooks Bend

Greenwood, IN

4 beds | 4 baths | 3,725 sq.ft.

$505,000

Airbnb cash on cash: 1.63%

Traditional cash on cash: 5.15%

Airbnb Rental Income: $2177

Traditional Rental Income: $3284

Airbnb ROI: 1.63%

Traditional ROI: 5.15%

5422 Wakefield Drive S

Greenwood, IN

4 beds | 4 baths | 4,452 sq.ft.

$400,000

Airbnb cash on cash: 2.52%

Traditional cash on cash: 7.29%

Airbnb Rental Income: $2177

Traditional Rental Income: $3414

Airbnb ROI: 2.52%

Traditional ROI: 7.29%

5400 Wakefield Drive S

Greenwood, IN

4 beds | 3 baths | 3,894 sq.ft.

$395,000

Airbnb cash on cash: 2.74%

Traditional cash on cash: 5.29%

Airbnb Rental Income: $2177

Traditional Rental Income: $2571

Airbnb ROI: 2.74%

Traditional ROI: 5.29%

229 Brighton Court

Greenwood, IN

3 beds | 3 baths | 1,844 sq.ft.

$300,000

Airbnb cash on cash: 1.95%

Traditional cash on cash: 5.07%

Airbnb Rental Income: $1946

Traditional Rental Income: $2312

Airbnb ROI: 1.95%