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.	$289,900	Airbnb cash on cash: 3.73% Traditional cash on cash: 5.16% Airbnb Rental Income: $1996 Traditional Rental Income: $1867 Airbnb ROI: 3.73% Traditional ROI: 5.16%
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: 4.44% Traditional cash on cash: 5.11% Airbnb Rental Income: $2892 Traditional Rental Income: $2456 Airbnb ROI: 4.44% Traditional ROI: 5.11%
1213 Barrington Drive Greenwood, IN Welcome home! This 4 bedrooms, 2.5 bathrooms, and over 3,000 square feet. This home offers...	4 beds \| 3 baths \| 2,020 sq.ft.	$339,900	Airbnb cash on cash: 5.24% Traditional cash on cash: 5.65% Airbnb Rental Income: $2892 Traditional Rental Income: $2354 Airbnb ROI: 5.24% Traditional ROI: 5.65%
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: 5.2% Traditional cash on cash: 5.79% Airbnb Rental Income: $2892 Traditional Rental Income: $2417 Airbnb ROI: 5.2% Traditional ROI: 5.79%
3724 Morningside Drive Greenwood, IN Welcome home to this beautifully crafted custom ranch featuring 4 bedrooms, 3.5 baths, and...	4 beds \| 4 baths \| 3,494 sq.ft.	$524,900	Airbnb cash on cash: 2.78% Traditional cash on cash: 4.82% Airbnb Rental Income: $2892 Traditional Rental Income: $3220 Airbnb ROI: 2.78% Traditional ROI: 4.82%
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: 4.12% Traditional cash on cash: 4.15% Airbnb Rental Income: $1585 Traditional Rental Income: $1138 Airbnb ROI: 4.12% 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: 2.89% Traditional cash on cash: 5.15% Airbnb Rental Income: $2892 Traditional Rental Income: $3284 Airbnb ROI: 2.89% 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: 4.11% Traditional cash on cash: 7.29% Airbnb Rental Income: $2892 Traditional Rental Income: $3414 Airbnb ROI: 4.11% 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: 4.35% Traditional cash on cash: 5.29% Airbnb Rental Income: $2892 Traditional Rental Income: $2571 Airbnb ROI: 4.35% 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: 2.1% Traditional cash on cash: 5.07% Airbnb Rental Income: $1996 Traditional Rental Income: $2312 Airbnb ROI: 2.1% Traditional ROI: 5.07%
1012 Hudson Bay Drive Greenwood, IN HEY WAIT A MINUTE THIS IS FOR YOU! HUGE PRICE IMPROVEMENT ON this four-bedroom, four bath ...	4 beds \| 4 baths \| 4,230 sq.ft.	$474,900	Airbnb cash on cash: 3.2% Traditional cash on cash: 6.7% Airbnb Rental Income: $2892 Traditional Rental Income: $3775 Airbnb ROI: 3.2% Traditional ROI: 6.7%
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: 4.06% Traditional cash on cash: 5.97% Airbnb Rental Income: $1996 Traditional Rental Income: $1935 Airbnb ROI: 4.06% 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: 1.65% Traditional cash on cash: 3.54% Airbnb Rental Income: $1996 Traditional Rental Income: $2277 Airbnb ROI: 1.65% 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: 1.36% Traditional cash on cash: 4.26% Airbnb Rental Income: $2892 Traditional Rental Income: $4520 Airbnb ROI: 1.36% Traditional ROI: 4.26%
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: 3.81% Traditional cash on cash: 3.13% Airbnb Rental Income: $2892 Traditional Rental Income: $1948 Airbnb ROI: 3.81% Traditional ROI: 3.13%
2 Bentwood Street Greenwood, IN 3 Bedrooms and 1.50 baths in Greenwood. Home needs extensive renovations, is currently in ...	3 beds \| 2 baths \| 1,248 sq.ft.	$160,000	Airbnb cash on cash: 7.8% Traditional cash on cash: 8.65% Airbnb Rental Income: $1996 Traditional Rental Income: $1604 Airbnb ROI: 7.8% Traditional ROI: 8.65%
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: 5.58% Traditional cash on cash: 5.75% Airbnb Rental Income: $1996 Traditional Rental Income: $1510 Airbnb ROI: 5.58% 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: 3.52% Traditional cash on cash: 5.38% Airbnb Rental Income: $1996 Traditional Rental Income: $1964 Airbnb ROI: 3.52% 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: 2.88% Traditional cash on cash: 4.64% Airbnb Rental Income: $1996 Traditional Rental Income: $2035 Airbnb ROI: 2.88% Traditional ROI: 4.64%
3442 Enclave Ln 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: 3.46% Traditional cash on cash: 4.44% Airbnb Rental Income: $1996 Traditional Rental Income: $1743 Airbnb ROI: 3.46% Traditional ROI: 4.44%
481 Runyon Road Greenwood, IN Your own private backyard oasis awaits! The highlight of this well-maintained 4-bedroom, 2...	4 beds \| 3 baths \| 3,679 sq.ft.	$450,000	Airbnb cash on cash: 3.54% Traditional cash on cash: 5.41% Airbnb Rental Income: $2892 Traditional Rental Income: $3008 Airbnb ROI: 3.54% Traditional ROI: 5.41%
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: 3.13% Traditional cash on cash: 6.22% Airbnb Rental Income: $1996 Traditional Rental Income: $2273 Airbnb ROI: 3.13% 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: 2.28% Traditional cash on cash: 4.27% Airbnb Rental Income: $1996 Traditional Rental Income: $2186 Airbnb ROI: 2.28% Traditional ROI: 4.27%
139 Campbell Road Greenwood, IN This is the one you have been waiting for! Custom-built brick ranch with basement on over ...	4 beds \| 3 baths \| 3,808 sq.ft.	$725,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 3.07% Airbnb Rental Income: $2892 Traditional Rental Income: $2852 Airbnb ROI: 2.14% Traditional ROI: 3.07%
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: 3.19% Traditional cash on cash: 5.61% Airbnb Rental Income: $1585 Traditional Rental Income: $1558 Airbnb ROI: 3.19% Traditional ROI: 5.61%
85 Tarry Court Greenwood, IN Experience 85 Tarry Ct, arranged for everyday practicality with a thoughtful layout center...	5 beds \| 3 baths \| 2,749 sq.ft.	$380,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.91% Airbnb Rental Income: $null Traditional Rental Income: $2687 Airbnb ROI: N/A Traditional ROI: 5.91%
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: 2.23% Traditional cash on cash: 6.52% Airbnb Rental Income: $2892 Traditional Rental Income: $4627 Airbnb ROI: 2.23% Traditional ROI: 6.52%
2702 Ashton Lane Greenwood, IN Welcome to this Beautiful 2-Story Home! This inviting 2-story home features 4 bedrooms and...	4 beds \| 3 baths \| 2,390 sq.ft.	$339,100	Airbnb cash on cash: 5.11% Traditional cash on cash: 5.72% Airbnb Rental Income: $2892 Traditional Rental Income: $2417 Airbnb ROI: 5.11% Traditional ROI: 5.72%
4763 Oakleigh Court Greenwood, IN Located on a quiet cul-de-sac in desirable Center Grove Schools, this spacious two-story h...	4 beds \| 3 baths \| 2,906 sq.ft.	$390,000	Airbnb cash on cash: 4.29% Traditional cash on cash: 3.87% Airbnb Rental Income: $2892 Traditional Rental Income: $2065 Airbnb ROI: 4.29% Traditional ROI: 3.87%
340 Averitt Road Greenwood, IN Charming 3-bedroom, 2-bath home on .42 acres with 1,456 sq ft of comfortable living space,...	3 beds \| 2 baths \| 1,456 sq.ft.	$259,900	Airbnb cash on cash: 4.38% Traditional cash on cash: 5.7% Airbnb Rental Income: $1996 Traditional Rental Income: $1797 Airbnb ROI: 4.38% Traditional ROI: 5.7%
243 E County Line Road Greenwood, IN Are you looking for a home walking distance from the golf course? Look no further! This st...	2 beds \| 2 baths \| 1,136 sq.ft.	$180,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 4.76% Airbnb Rental Income: $1585 Traditional Rental Income: $1122 Airbnb ROI: 4.82% Traditional ROI: 4.76%
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: 1.26% Traditional cash on cash: 3.96% Airbnb Rental Income: $1996 Traditional Rental Income: $2625 Airbnb ROI: 1.26% 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: 3.32% Traditional cash on cash: 3.87% Airbnb Rental Income: $2892 Traditional Rental Income: $2464 Airbnb ROI: 3.32% Traditional ROI: 3.87%
3463 Enclave Ln 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: 3.33% Traditional cash on cash: 4.78% Airbnb Rental Income: $1996 Traditional Rental Income: $1883 Airbnb ROI: 3.33% 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: 5.17% Traditional cash on cash: 4.94% Airbnb Rental Income: $1996 Traditional Rental Income: $1425 Airbnb ROI: 5.17% 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: 4.39% Traditional cash on cash: 4.87% Airbnb Rental Income: $1996 Traditional Rental Income: $1572 Airbnb ROI: 4.39% Traditional ROI: 4.87%
296 Webber Way Greenwood, IN Don't let the bedroom count fool you!! This home lives significantly larger than it appear...	3 beds \| 2 baths \| 1,776 sq.ft.	$315,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.87% Airbnb Rental Income: $1996 Traditional Rental Income: $1941 Airbnb ROI: 3.3% Traditional ROI: 4.87%
4858 Brentridge Place Greenwood, IN Here's your opportunity to own an updated, full brick, custom built home in Brentridge Est...	4 beds \| 3 baths \| 3,830 sq.ft.	$549,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 3.75% Airbnb Rental Income: $2892 Traditional Rental Income: $2768 Airbnb ROI: 2.68% Traditional ROI: 3.75%
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.	$650,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 6.71% Airbnb Rental Income: $2892 Traditional Rental Income: $5110 Airbnb ROI: 1.94% Traditional ROI: 6.71%
1167 Station Drive Greenwood, IN Welcome home to this well-maintained 4-bedroom, 2.5-bath home featuring a light, bright, a...	4 beds \| 3 baths \| 2,218 sq.ft.	$339,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 5.61% Airbnb Rental Income: $2892 Traditional Rental Income: $2411 Airbnb ROI: 5.01% Traditional ROI: 5.61%

Real Estate investment in Greenwood, IN

There are 272 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 $120. In July 2026, the average monthly cash on cash return in Greenwood is 5.00%. The average monthly rental income in Greenwood is $2,349.

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

There are 272 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 $2,349.

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.

$289,900

Airbnb cash on cash: 3.73%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $1996

Traditional Rental Income: $1867

Airbnb ROI: 3.73%

Traditional ROI: 5.16%

5415 Misthaven Lane

Greenwood, IN

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

$375,000

Airbnb cash on cash: 4.44%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $2892

Traditional Rental Income: $2456

Airbnb ROI: 4.44%

Traditional ROI: 5.11%

1213 Barrington Drive

Greenwood, IN

4 beds | 3 baths | 2,020 sq.ft.

$339,900

Airbnb cash on cash: 5.24%

Traditional cash on cash: 5.65%

Airbnb Rental Income: $2892

Traditional Rental Income: $2354

Airbnb ROI: 5.24%

Traditional ROI: 5.65%

2689 Falcon Drive

Greenwood, IN

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

$350,000

Airbnb cash on cash: 5.2%

Traditional cash on cash: 5.79%

Airbnb Rental Income: $2892

Traditional Rental Income: $2417

Airbnb ROI: 5.2%

Traditional ROI: 5.79%

3724 Morningside Drive

Greenwood, IN

4 beds | 4 baths | 3,494 sq.ft.

$524,900

Airbnb cash on cash: 2.78%

Traditional cash on cash: 4.82%

Airbnb Rental Income: $2892

Traditional Rental Income: $3220

Airbnb ROI: 2.78%

Traditional ROI: 4.82%

1144 Barbara Drive

Greenwood, IN

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

$204,999

Airbnb cash on cash: 4.12%

Traditional cash on cash: 4.15%

Airbnb Rental Income: $1585

Traditional Rental Income: $1138

Airbnb ROI: 4.12%

Traditional ROI: 4.15%

5263 Brooks Bend

Greenwood, IN

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

$505,000

Airbnb cash on cash: 2.89%

Traditional cash on cash: 5.15%

Airbnb Rental Income: $2892

Traditional Rental Income: $3284

Airbnb ROI: 2.89%

Traditional ROI: 5.15%

5422 Wakefield Drive S

Greenwood, IN

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

$400,000

Airbnb cash on cash: 4.11%

Traditional cash on cash: 7.29%

Airbnb Rental Income: $2892

Traditional Rental Income: $3414

Airbnb ROI: 4.11%