Real Estate Investment Properties for Sale in Greenwood, MO

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
108 Pin Oak Dr Greenwood, MO ONE-LEVEL LIVING IN THE HEART OF GREENWOOD \| $228,000 Move-in ready and convenient to ev...	2 beds \| 2 baths \| 1,388 sq.ft.	$228,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 6.25% Airbnb Rental Income: $1540 Traditional Rental Income: $1872 Airbnb ROI: 2.64% Traditional ROI: 6.25%
25103 Haines Rd Greenwood, MO Custom Two Story on 2.96 m/l acres in desirable Timberlake Estates! This spacious Two Stor...	5 beds \| 5 baths \| 4,698 sq.ft.	$689,900	Airbnb cash on cash: 2.34% Traditional cash on cash: 8.19% Airbnb Rental Income: $3697 Traditional Rental Income: $6655 Airbnb ROI: 2.34% Traditional ROI: 8.19%
302 16th Ave S Greenwood, MO Nestled in Greenwood, this affordable split level offers so much room for growth. Three be...	3 beds \| 2 baths \| 1,567 sq.ft.	$330,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 5.1% Airbnb Rental Income: $2460 Traditional Rental Income: $2285 Airbnb ROI: 3.74% Traditional ROI: 5.1%
1108 Deer Run Dr Greenwood, MO Located in the award-winning Lee's Summit School District, this stunning JFE-built home of...	4 beds \| 4 baths \| 3,143 sq.ft.	$739,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 2.65% Airbnb Rental Income: $3311 Traditional Rental Income: $3154 Airbnb ROI: 1.8% Traditional ROI: 2.65%
1149 Hummingbird Ct Greenwood, MO Nestled on a private, wooded estate lot at the end of a quiet cul-de-sac, this stunning cu...	4 beds \| 4 baths \| 3,502 sq.ft.	$865,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 1.55% Airbnb Rental Income: $3311 Traditional Rental Income: $3333 Airbnb ROI: 0.6% Traditional ROI: 1.55%
908 Savannah Ln Greenwood, MO Stunning new Whitney Modern Reverse plan by L & G Homes. The designer finishes will wow yo...	4 beds \| 3 baths \| 2,800 sq.ft.	$667,500	Airbnb cash on cash: 2.78% Traditional cash on cash: 3.95% Airbnb Rental Income: $3311 Traditional Rental Income: $3302 Airbnb ROI: 2.78% Traditional ROI: 3.95%
33604 E Stringtown Rd Greenwood, MO Custom 1.5-story home on 9.48 wooded acres surrounded by wildlife in Greenwood that alread...	4 beds \| 3 baths \| 3,756 sq.ft.	$625,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 4.51% Airbnb Rental Income: $3311 Traditional Rental Income: $3839 Airbnb ROI: 2.34% Traditional ROI: 4.51%
1004 Wilds Pkwy Greenwood, MO Don't miss this new home by Walker Custom Homes! The Layla 1 1/2 Story home features grand...	4 beds \| 3 baths \| 2,537 sq.ft.	$761,850	Airbnb cash on cash: 1.42% Traditional cash on cash: 1.83% Airbnb Rental Income: $3311 Traditional Rental Income: $2866 Airbnb ROI: 1.42% Traditional ROI: 1.83%
N Mo-7 Hwy Greenwood, MO N Mo-7 Hwy, Greenwood, MO 64034 \| Other	N/A beds \| N/A baths \| N/A	$1,820,000	Airbnb cash on cash: -1.66% Traditional cash on cash: -1.49% Airbnb Rental Income: $960 Traditional Rental Income: $891 Airbnb ROI: -1.66% Traditional ROI: -1.49%
1007 Wilds Pkwy Greenwood, MO Discover the spacious reverse floor plan you have been looking for! The Phoenix III by Wal...	4 beds \| 3 baths \| 3,095 sq.ft.	$826,408	Airbnb cash on cash: 0.79% Traditional cash on cash: 1.46% Airbnb Rental Income: $3311 Traditional Rental Income: $3082 Airbnb ROI: 0.79% Traditional ROI: 1.46%
703 19th Avenue N Greenwood, MO Welcome home to this beautifully maintained 4-bedroom, 3.5-bath home offering the perfect ...	4 beds \| 4 baths \| 2,345 sq.ft.	$450,000	Airbnb cash on cash: 3.64% Traditional cash on cash: 4.87% Airbnb Rental Income: $3311 Traditional Rental Income: $3087 Airbnb ROI: 3.64% Traditional ROI: 4.87%
1100 Deer Run Dr Greenwood, MO Heather Reverse plan by Walker Custom Homes! This Craftsman style home is situated on a go...	4 beds \| 4 baths \| 3,080 sq.ft.	$794,908	Airbnb cash on cash: 2.22% Traditional cash on cash: 3.37% Airbnb Rental Income: $3311 Traditional Rental Income: $3423 Airbnb ROI: 2.22% Traditional ROI: 3.37%
1117 Hummingbird Ct Greenwood, MO Modern and spacious home has 5 bedrooms, 5 full baths and a main floor office. So much roo...	5 beds \| 5 baths \| 4,074 sq.ft.	$869,500	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.7% Airbnb Rental Income: $3697 Traditional Rental Income: $4998 Airbnb ROI: 1.1% Traditional ROI: 3.7%
14300 S Smart Rd Greenwood, MO 14300 S Smart Rd, Greenwood, MO 64034 \| Single Family Residential	4 beds \| 3 baths \| 3,396 sq.ft.	$1,179,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 0.6% Airbnb Rental Income: $3311 Traditional Rental Income: $2902 Airbnb ROI: 0.3% Traditional ROI: 0.6%
912 Savannah Ln Greenwood, MO Welcome to a truly special Edgeless Design home in Woodland Trails where warm interior spa...	4 beds \| 3 baths \| 3,064 sq.ft.	$965,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 0.93% Airbnb Rental Income: $3311 Traditional Rental Income: $3104 Airbnb ROI: 0.33% Traditional ROI: 0.93%
803 Savannah Ct Greenwood, MO Open and spacious Whitney reverse plan by L & G Homes. The gable vaulted ceiling will wow ...	4 beds \| 3 baths \| 2,800 sq.ft.	$629,900	Airbnb cash on cash: 1.74% Traditional cash on cash: 2.59% Airbnb Rental Income: $3311 Traditional Rental Income: $3070 Airbnb ROI: 1.74% Traditional ROI: 2.59%
25409 Timberlake Trl Greenwood, MO Nestled on a stunning 3-acre corner lot in the highly sought-after Timberlake Estates, thi...	3 beds \| 4 baths \| 3,160 sq.ft.	$615,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.59% Airbnb Rental Income: $2460 Traditional Rental Income: $3314 Airbnb ROI: 1.06% Traditional ROI: 3.59%
2103 Patti Ln Greenwood, MO 2103 Patti Ln, Greenwood, MO 64034 \| Single Family Residential	4 beds \| 3 baths \| 2,524 sq.ft.	$345,000	Airbnb cash on cash: 5.68% Traditional cash on cash: 6.14% Airbnb Rental Income: $3311 Traditional Rental Income: $2719 Airbnb ROI: 5.68% Traditional ROI: 6.14%
1208 Aspen Dr Greenwood, MO Sought after Lee Summit School District. This home is located in Greenwood Missouri. The h...	3 beds \| 2 baths \| 1,420 sq.ft.	$315,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 4.72% Airbnb Rental Income: $2460 Traditional Rental Income: $2082 Airbnb ROI: 3.97% Traditional ROI: 4.72%
14615 Whippoorwill Ln Greenwood, MO Nestled on 5 breathtaking wooded acres in the highly sought-after Whippoorwill Place subdi...	5 beds \| 4 baths \| 5,651 sq.ft.	$1,100,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 1.2% Airbnb Rental Income: $3697 Traditional Rental Income: $3276 Airbnb ROI: 0.83% Traditional ROI: 1.2%
13801 S Pebblebrook Ln Greenwood, MO AMAZING & truly extraordinary Reverse 1.5-Story Estate in a private gated community. The p...	5 beds \| 5 baths \| 6,338 sq.ft.	$2,000,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 0.73% Airbnb Rental Income: $3697 Traditional Rental Income: $4905 Airbnb ROI: -0.35% Traditional ROI: 0.73%
410 Copeland Dr Greenwood, MO Fully remodeled and move-in ready in the highly sought-after Lee's Summit School District!...	4 beds \| 2 baths \| 2,138 sq.ft.	$349,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 5.46% Airbnb Rental Income: $3311 Traditional Rental Income: $2455 Airbnb ROI: 5.81% Traditional ROI: 5.46%
305 Pinetree Dr Greenwood, MO Quiet cul-de-sac living in Greenwood with R-7 schools and no HOA! Enjoy the small-town cha...	3 beds \| 2 baths \| 1,451 sq.ft.	$309,900	Airbnb cash on cash: 4.25% Traditional cash on cash: 5.31% Airbnb Rental Income: $2460 Traditional Rental Income: $2173 Airbnb ROI: 4.25% Traditional ROI: 5.31%
2104 Cherokee Dr Greenwood, MO Welcome home to this beautifully maintained ranch offering the ease of one-level living! T...	3 beds \| 2 baths \| 1,380 sq.ft.	$338,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 4.02% Airbnb Rental Income: $2460 Traditional Rental Income: $1927 Airbnb ROI: 3.81% Traditional ROI: 4.02%
1000 Bellflower Ln Greenwood, MO JUST LISTED!! This Greenwood gem has everything you've been looking for! Perfectly situate...	4 beds \| 3 baths \| 3,036 sq.ft.	$523,500	Airbnb cash on cash: 2.7% Traditional cash on cash: 3.47% Airbnb Rental Income: $3311 Traditional Rental Income: $2949 Airbnb ROI: 2.7% Traditional ROI: 3.47%
2225 Martha Ln Greenwood, MO Welcome home to this meticulously maintained 4-bedroom, 3-bath residence that perfectly bl...	4 beds \| 3 baths \| 1,934 sq.ft.	$479,900	Airbnb cash on cash: 3.67% Traditional cash on cash: 4.11% Airbnb Rental Income: $3311 Traditional Rental Income: $2769 Airbnb ROI: 3.67% Traditional ROI: 4.11%
907 SPRUCE Drive Greenwood, MO SHORT SALE BANK APPROVED W/ BUYER CLOSING COSTS CREDITS ADDITIONAL. This exceptional prope...	4 beds \| 3 baths \| 1,737 sq.ft.	$292,000	Airbnb cash on cash: 6.82% Traditional cash on cash: 6.23% Airbnb Rental Income: $3311 Traditional Rental Income: $2408 Airbnb ROI: 6.82% Traditional ROI: 6.23%
804 Old Hickory Road Greenwood, MO 1.5 story with 5 bedrooms, 4.5 baths, just doesn't say enough about this fabulous home. Me...	5 beds \| 5 baths \| 4,124 sq.ft.	$749,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 4.39% Airbnb Rental Income: $3697 Traditional Rental Income: $4813 Airbnb ROI: 1.63% Traditional ROI: 4.39%
29509 E Stringtown Road Greenwood, MO Sold before processed.	3 beds \| 3 baths \| 4,169 sq.ft.	$840,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 2.06% Airbnb Rental Income: $2460 Traditional Rental Income: $3233 Airbnb ROI: 0.3% Traditional ROI: 2.06%
1013 Old Hickory Road Greenwood, MO Welcome to 1013 Old Hickory Road, a truly custom-built 4-bedroom, 4-bathroom home located ...	4 beds \| 4 baths \| 3,214 sq.ft.	$734,950	Airbnb cash on cash: 1.36% Traditional cash on cash: 2.91% Airbnb Rental Income: $3311 Traditional Rental Income: $3629 Airbnb ROI: 1.36% Traditional ROI: 2.91%
1606 Curtis Drive Greenwood, MO Welcome to a beautifully updated home that combines functional living spaces with a privat...	4 beds \| 4 baths \| 2,855 sq.ft.	$405,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 5.39% Airbnb Rental Income: $3311 Traditional Rental Income: $3017 Airbnb ROI: 4.21% Traditional ROI: 5.39%
1308 Bradford Drive Greenwood, MO Welcome to this exceptionally well-maintained 3-bedroom, 2-bath home offering comfort, fun...	3 beds \| 2 baths \| 1,370 sq.ft.	$329,900	Airbnb cash on cash: 3.88% Traditional cash on cash: 4.44% Airbnb Rental Income: $2460 Traditional Rental Income: $2034 Airbnb ROI: 3.88% Traditional ROI: 4.44%
1002 Tabitha Lane Greenwood, MO Welcome home to this well maintained 3 bedroom 2.5 bath property featuring vaulted ceiling...	3 beds \| 3 baths \| 1,848 sq.ft.	$335,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 6.04% Airbnb Rental Income: $2460 Traditional Rental Income: $2614 Airbnb ROI: 3.65% Traditional ROI: 6.04%
12904 Quail Ridge Greenwood, MO Tucked away on 2.36 acres and backing directly to the 3,000+ acre James A. Reed Memorial W...	4 beds \| 3 baths \| 3,800 sq.ft.	$725,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 2.27% Airbnb Rental Income: $3311 Traditional Rental Income: $2836 Airbnb ROI: 1.88% Traditional ROI: 2.27%

Real Estate investment in Greenwood, MO

There are 36 properties for sale in the city of Greenwood . The median list price in Greenwood is $349,691 and the average price per square foot is $133. In July 2026, the average monthly cash on cash return in Greenwood is 4.00%. The average monthly rental income in Greenwood is $3,044.

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

There are 36 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 $3,044.

Your search for investment property begins and ends here

Investment Property for Sale in Greenwood, MO

108 Pin Oak Dr

Greenwood, MO

2 beds | 2 baths | 1,388 sq.ft.

$228,000

Airbnb cash on cash: 2.64%

Traditional cash on cash: 6.25%

Airbnb Rental Income: $1540

Traditional Rental Income: $1872

Airbnb ROI: 2.64%

Traditional ROI: 6.25%

25103 Haines Rd

Greenwood, MO

5 beds | 5 baths | 4,698 sq.ft.

$689,900

Airbnb cash on cash: 2.34%

Traditional cash on cash: 8.19%

Airbnb Rental Income: $3697

Traditional Rental Income: $6655

Airbnb ROI: 2.34%

Traditional ROI: 8.19%

302 16th Ave S

Greenwood, MO

3 beds | 2 baths | 1,567 sq.ft.

$330,000

Airbnb cash on cash: 3.74%

Traditional cash on cash: 5.1%

Airbnb Rental Income: $2460

Traditional Rental Income: $2285

Airbnb ROI: 3.74%

Traditional ROI: 5.1%

1108 Deer Run Dr

Greenwood, MO

4 beds | 4 baths | 3,143 sq.ft.

$739,000

Airbnb cash on cash: 1.8%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $3311

Traditional Rental Income: $3154

Airbnb ROI: 1.8%

Traditional ROI: 2.65%

1149 Hummingbird Ct

Greenwood, MO

4 beds | 4 baths | 3,502 sq.ft.

$865,000

Airbnb cash on cash: 0.6%

Traditional cash on cash: 1.55%

Airbnb Rental Income: $3311

Traditional Rental Income: $3333

Airbnb ROI: 0.6%

Traditional ROI: 1.55%

908 Savannah Ln

Greenwood, MO

4 beds | 3 baths | 2,800 sq.ft.

$667,500

Airbnb cash on cash: 2.78%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $3311

Traditional Rental Income: $3302

Airbnb ROI: 2.78%

Traditional ROI: 3.95%

33604 E Stringtown Rd

Greenwood, MO

4 beds | 3 baths | 3,756 sq.ft.

$625,000

Airbnb cash on cash: 2.34%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $3311

Traditional Rental Income: $3839

Airbnb ROI: 2.34%

Traditional ROI: 4.51%

1004 Wilds Pkwy

Greenwood, MO

4 beds | 3 baths | 2,537 sq.ft.

$761,850

Airbnb cash on cash: 1.42%

Traditional cash on cash: 1.83%

Airbnb Rental Income: $3311

Traditional Rental Income: $2866

Airbnb ROI: 1.42%