Real Estate Investment Properties for Sale in Highlandville, MO

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
115 Ravenhill Dr Highlandville, MO One-of-a-kind 3 bed, 3 bath home on 2.8 private acres in the Ozark Mountains. Open floor p...	3 beds \| 3 baths \| 2,951 sq.ft.	$429,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 5.31% Airbnb Rental Income: $1832 Traditional Rental Income: $2840 Airbnb ROI: 1.57% Traditional ROI: 5.31%
1115 Highlandville Rd Highlandville, MO *Back on the market at no fault of the seller* Welcome to 1115 Highlandville Road, a b...	4 beds \| 2 baths \| 2,003 sq.ft.	$469,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 5.17% Airbnb Rental Income: $1772 Traditional Rental Income: $2919 Airbnb ROI: 1.45% Traditional ROI: 5.17%
395 Bear Rdg Highlandville, MO 395 Bear Ridge Highlandville MO. Come see this redone and well cared for home on 5 acres i...	4 beds \| 2 baths \| 1,502 sq.ft.	$395,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 4.53% Airbnb Rental Income: $1772 Traditional Rental Income: $2310 Airbnb ROI: 1.77% Traditional ROI: 4.53%
3679 Two Rivers Rd Highlandville, MO HUGE PRICE REDUCTION!!!Prime Location! 3+ Surveyed Acres Near Nixa, Highlandville & Spring...	2 beds \| 1 baths \| 1,280 sq.ft.	$139,500	Airbnb cash on cash: 4.67% Traditional cash on cash: 6.43% Airbnb Rental Income: $1312 Traditional Rental Income: $1140 Airbnb ROI: 4.67% Traditional ROI: 6.43%
1568 Glossip Ave Highlandville, MO Incredible setting of rolling acres, meticulous home & property, 5 car garages, in-ground ...	3 beds \| 2 baths \| 2,482 sq.ft.	$590,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 3.6% Airbnb Rental Income: $1832 Traditional Rental Income: $2777 Airbnb ROI: 0.98% Traditional ROI: 3.6%
755 Highlandville Rd Highlandville, MO Charming property on 4.93 acres conveniently located in Highlandville. It boasts a brand n...	3 beds \| 2 baths \| 1,708 sq.ft.	$419,900	Airbnb cash on cash: 1.74% Traditional cash on cash: 4.13% Airbnb Rental Income: $1832 Traditional Rental Income: $2278 Airbnb ROI: 1.74% Traditional ROI: 4.13%
3095 State Highway O Highlandville, MO Opportunities like this are almost impossible to find! Whether you're searching for a fami...	5 beds \| 3 baths \| 3,583 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $3056 Airbnb ROI: N/A Traditional ROI: 4.67%
170 Country View Rd Highlandville, MO This Beautiful Spacious 5 Bedroom 3 Bath Home on 6+ acres is Move-In Ready!Inside you will...	5 beds \| 3 baths \| 2,651 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.81% Airbnb Rental Income: $null Traditional Rental Income: $3007 Airbnb ROI: N/A Traditional ROI: 4.81%
003 State Hwy O Highlandville, MO 003 State Hwy O, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| N/A	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.4% Airbnb Rental Income: $null Traditional Rental Income: $788 Airbnb ROI: N/A Traditional ROI: -0.4%
000 Logan Ave Highlandville, MO 000 Logan Ave, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$260,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.98% Airbnb Rental Income: $null Traditional Rental Income: $1059 Airbnb ROI: N/A Traditional ROI: 1.98%
002 State Hwy O Highlandville, MO 002 State Hwy O, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$264,500	Airbnb cash on cash: N/A Traditional cash on cash: 0.82% Airbnb Rental Income: $null Traditional Rental Income: $788 Airbnb ROI: N/A Traditional ROI: 0.82%
331 Raspberry Rd Highlandville, MO 331 Raspberry Rd, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| N/A	$49,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.73% Airbnb Rental Income: $null Traditional Rental Income: $788 Airbnb ROI: N/A Traditional ROI: 11.73%
3095b State Highway O Highlandville, MO Rarely does a property offer this much versatility, beauty, and opportunity! Welcome to 30...	5 beds \| 3 baths \| 3,583 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.87% Airbnb Rental Income: $null Traditional Rental Income: $2975 Airbnb ROI: N/A Traditional ROI: 2.87%
000 Joshua Tree Rd Highlandville, MO 000 Joshua Tree Rd, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| N/A	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.88% Airbnb Rental Income: $null Traditional Rental Income: $897 Airbnb ROI: N/A Traditional ROI: -0.88%
000 Accacia Dr Highlandville, MO 000 Accacia Dr, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| N/A	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $878 Airbnb ROI: N/A Traditional ROI: 4.56%
3095c State Highway O Highlandville, MO Welcome to 3095 State Highway O in Highlandville, where 63 beautiful acres provide the per...	5 beds \| 3 baths \| 3,583 sq.ft.	$999,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.94% Airbnb Rental Income: $null Traditional Rental Income: $3003 Airbnb ROI: N/A Traditional ROI: 1.94%
200 Highlandville Rd Highlandville, MO 200 Highlandville Rd, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| N/A	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.43% Airbnb Rental Income: $null Traditional Rental Income: $878 Airbnb ROI: N/A Traditional ROI: 0.43%
805 Raspberry Road lot: #50 Highlandville, MO THIS BEAUTIFULLY CRAFTED NEW CONSTRUCTION HOME just keeps GETTING BETTER!! With a PRICE AD...	4 beds \| 3 baths \| 3,060 sq.ft.	$475,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 5.6% Airbnb Rental Income: $1772 Traditional Rental Income: $3043 Airbnb ROI: 1.65% Traditional ROI: 5.6%
811 Rainbow Valley Dr Highlandville, MO RIVERFRONT PARADISE ON THE JAMES RIVER! Experience the ultimate Ozark lifestyle on this st...	3 beds \| 2 baths \| 2,030 sq.ft.	$539,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.02% Airbnb Rental Income: $1832 Traditional Rental Income: $2213 Airbnb ROI: 1.28% Traditional ROI: 3.02%
495 Bear Rdg Highlandville, MO Welcome to your private retreat in the heart of Highlandville! Nestled on 5 beautiful acre...	5 beds \| 3 baths \| 3,300 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.75% Airbnb Rental Income: $null Traditional Rental Income: $3000 Airbnb ROI: N/A Traditional ROI: 4.75%
000 Us Highway 65 S Highlandville, MO 000 Us Highway 65 S, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| N/A	$942,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.05% Airbnb Rental Income: $null Traditional Rental Income: $897 Airbnb ROI: N/A Traditional ROI: -1.05%
000 State Highway O Highlandville, MO 000 State Highway O, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| N/A	$997,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.1% Airbnb Rental Income: $null Traditional Rental Income: $897 Airbnb ROI: N/A Traditional ROI: -1.1%
000 State Hwy 65 Highlandville, MO 000 State Hwy 65, Highlandville, MO 65669 \| Other	N/A beds \| N/A baths \| N/A	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.27% Airbnb Rental Income: $null Traditional Rental Income: $897 Airbnb ROI: N/A Traditional ROI: -1.27%
612 Stoneshire Drive Highlandville, MO Nestled on nearly 4 acres in desirable Highlandville, this unique 3-bedroom, 2-bath earth-...	3 beds \| 2 baths \| 1,764 sq.ft.	$319,500	Airbnb cash on cash: 2.71% Traditional cash on cash: 5.86% Airbnb Rental Income: $1832 Traditional Rental Income: $2286 Airbnb ROI: 2.71% Traditional ROI: 5.86%
117 Tower Rd Highlandville, MO 117 Tower Rd, Highlandville, MO 65669 \| Single Family Residential	4 beds \| 3 baths \| 3,000 sq.ft.	$299,000	Airbnb cash on cash: 2.23% Traditional cash on cash: 7.41% Airbnb Rental Income: $1772 Traditional Rental Income: $2746 Airbnb ROI: 2.23% Traditional ROI: 7.41%
247 Bradley Ct Highlandville, MO 247 Bradley Ct, Highlandville, MO 65669 \| Single Family Residential	3 beds \| 2 baths \| 1,315 sq.ft.	$259,999	Airbnb cash on cash: 3.11% Traditional cash on cash: 5.15% Airbnb Rental Income: $1832 Traditional Rental Income: $1837 Airbnb ROI: 3.11% Traditional ROI: 5.15%
271 Maplewood Dr Highlandville, MO 271 Maplewood Dr, Highlandville, MO 65669 \| Single Family Residential	3 beds \| 2 baths \| 1,184 sq.ft.	$200,000	Airbnb cash on cash: 4.6% Traditional cash on cash: 6.82% Airbnb Rental Income: $1832 Traditional Rental Income: $1760 Airbnb ROI: 4.6% Traditional ROI: 6.82%
255 Maplewood Dr Highlandville, MO 255 Maplewood Dr, Highlandville, MO 65669 \| Single Family Residential	3 beds \| 2 baths \| 1,167 sq.ft.	$265,000	Airbnb cash on cash: 3.02% Traditional cash on cash: 4.7% Airbnb Rental Income: $1832 Traditional Rental Income: $1759 Airbnb ROI: 3.02% Traditional ROI: 4.7%
667 Rainbow Valley Dr Highlandville, MO 667 Rainbow Valley Dr, Highlandville, MO 65669 \| Single Family Residential	4 beds \| 3 baths \| 2,494 sq.ft.	$360,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 5.84% Airbnb Rental Income: $1772 Traditional Rental Income: $2729 Airbnb ROI: 1.57% Traditional ROI: 5.84%
184 Barnridge Rd Highlandville, MO 184 Barnridge Rd, Highlandville, MO 65669 \| Single Family Residential	3 beds \| 2 baths \| 2,600 sq.ft.	$414,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.84% Airbnb Rental Income: $1832 Traditional Rental Income: $2348 Airbnb ROI: 1.24% Traditional ROI: 3.84%
748 Ellingsworth Lane Highlandville, MO Dead-end street. Three quarters of an acre. The kind of quiet you actually have to go look...	3 beds \| 2 baths \| 1,448 sq.ft.	$259,900	Airbnb cash on cash: 3.73% Traditional cash on cash: 5.99% Airbnb Rental Income: $1832 Traditional Rental Income: $1894 Airbnb ROI: 3.73% Traditional ROI: 5.99%
1367 Glossip Ave Highlandville, MO This spacious, remodeled, clean, and well cared for homes shows well and features 5 bedroo...	5 beds \| 3 baths \| 2,952 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $3042 Airbnb ROI: N/A Traditional ROI: 4.86%
152 Dry Creek Lane Highlandville, MO Welcome home to this beautiful 4 bedroom, 3 bathroom home located on a quiet dead-end stre...	4 beds \| 3 baths \| 3,299 sq.ft.	$449,900	Airbnb cash on cash: 1.25% Traditional cash on cash: 4.42% Airbnb Rental Income: $1772 Traditional Rental Income: $2625 Airbnb ROI: 1.25% Traditional ROI: 4.42%
228 Logan Avenue Highlandville, MO Tucked away on 2.3 peaceful acres in Highlandville, this adorable hobby farm is the perfec...	4 beds \| 3 baths \| 1,850 sq.ft.	$350,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 6.2% Airbnb Rental Income: $1772 Traditional Rental Income: $2576 Airbnb ROI: 2.28% Traditional ROI: 6.2%

Real Estate investment in Highlandville, MO

There are 35 properties for sale in the city of Highlandville . The median list price in Highlandville is $269,739 and the average price per square foot is $159. In August 2026, the average monthly cash on cash return in Highlandville is 5.00%. The average monthly rental income in Highlandville is $2,282.

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

There are 35 investment properties available for sale in Highlandville.

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

The ROI for Long-Term is higher than the Short-Term in Highlandville with average rental income of $2,282.

Your search for investment property begins and ends here

Investment Property for Sale in Highlandville, MO

115 Ravenhill Dr

Highlandville, MO

3 beds | 3 baths | 2,951 sq.ft.

$429,000

Airbnb cash on cash: 1.57%

Traditional cash on cash: 5.31%

Airbnb Rental Income: $1832

Traditional Rental Income: $2840

Airbnb ROI: 1.57%

Traditional ROI: 5.31%

1115 Highlandville Rd

Highlandville, MO

4 beds | 2 baths | 2,003 sq.ft.

$469,000

Airbnb cash on cash: 1.45%

Traditional cash on cash: 5.17%

Airbnb Rental Income: $1772

Traditional Rental Income: $2919

Airbnb ROI: 1.45%

Traditional ROI: 5.17%

395 Bear Rdg

Highlandville, MO

4 beds | 2 baths | 1,502 sq.ft.

$395,000

Airbnb cash on cash: 1.77%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $1772

Traditional Rental Income: $2310

Airbnb ROI: 1.77%

Traditional ROI: 4.53%

3679 Two Rivers Rd

Highlandville, MO

2 beds | 1 baths | 1,280 sq.ft.

$139,500

Airbnb cash on cash: 4.67%

Traditional cash on cash: 6.43%

Airbnb Rental Income: $1312

Traditional Rental Income: $1140

Airbnb ROI: 4.67%

Traditional ROI: 6.43%

1568 Glossip Ave

Highlandville, MO

3 beds | 2 baths | 2,482 sq.ft.

$590,000

Airbnb cash on cash: 0.98%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $1832

Traditional Rental Income: $2777

Airbnb ROI: 0.98%

Traditional ROI: 3.6%

755 Highlandville Rd

Highlandville, MO

3 beds | 2 baths | 1,708 sq.ft.

$419,900

Airbnb cash on cash: 1.74%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $1832

Traditional Rental Income: $2278

Airbnb ROI: 1.74%

Traditional ROI: 4.13%

3095 State Highway O

Highlandville, MO

5 beds | 3 baths | 3,583 sq.ft.

$525,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.67%

Airbnb Rental Income: $null

Traditional Rental Income: $3056

Airbnb ROI: N/A

Traditional ROI: 4.67%

170 Country View Rd

Highlandville, MO

5 beds | 3 baths | 2,651 sq.ft.

$499,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.81%

Airbnb Rental Income: $null

Traditional Rental Income: $3007

Airbnb ROI: N/A