Real Estate Investment Properties for Sale in Bennington, OK

Looking for investment property in Bennington, OK with high ROI ?

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
4168 Armstrong Academy Bennington, OK 137 Acres of Cattle Land with Ranch Home! Property features Bermuda and native grasses, fi...	3 beds \| 1 baths \| 2,056 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.7% Airbnb Rental Income: $null Traditional Rental Income: $2604 Airbnb ROI: N/A Traditional ROI: 1.7%
488 Rock House Rd Bennington, OK A Dream Home Opportunity on 9.7 Acres Nestled on a picturesque hillside just off US Hig...	3 beds \| N/A baths \| 3,610 sq.ft.	$379,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.79% Airbnb Rental Income: $null Traditional Rental Income: $2013 Airbnb ROI: N/A Traditional ROI: 3.79%
36953 Us Highway 70 Bennington, OK Experience the perfect blend of country living and outdoor adventure on this exceptional 5...	4 beds \| 2 baths \| 2,256 sq.ft.	$489,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $2512 Airbnb ROI: N/A Traditional ROI: 3.39%
37001 Us Hwy 70 Bennington, OK Escape to this 55-acre +/- estate on Highway 70, where country living and outdoor adventur...	3 beds \| 2 baths \| 2,064 sq.ft.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $2255 Airbnb ROI: N/A Traditional ROI: 3.03%
699 Cox Ln Bennington, OK Escape the noise and discover the tranquility of true country living with this charming 3-...	3 beds \| 2 baths \| 1,300 sq.ft.	$195,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.07% Airbnb Rental Income: $null Traditional Rental Income: $1937 Airbnb ROI: N/A Traditional ROI: 8.07%
1965 Starlight Ln Bennington, OK Unique opportunity to purchase your very own 40 acres, located at the end of the road, off...	3 beds \| 2 baths \| 1,792 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.05% Airbnb Rental Income: $null Traditional Rental Income: $2331 Airbnb ROI: N/A Traditional ROI: 5.05%
36977 Hwy 70 Bennington, OK 36977 Hwy 70, Bennington, OK 74723 \| Single Family Residential	6 beds \| 4 baths \| 4,400 sq.ft.	$823,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.5% Airbnb Rental Income: $null Traditional Rental Income: $3466 Airbnb ROI: N/A Traditional ROI: 2.5%
240 Magnolia Bennington, OK 240 Magnolia, Bennington, OK 74723 \| Single Family Residential	3 beds \| 3 baths \| 4,040 sq.ft.	$2,555,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.87% Airbnb Rental Income: $null Traditional Rental Income: $2510 Airbnb ROI: N/A Traditional ROI: -0.87%
001 Shoe Make Bennington, OK 001 Shoe Make, Bennington, OK 74723 \| Other	N/A beds \| N/A baths \| N/A	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.32% Airbnb Rental Income: $null Traditional Rental Income: $800 Airbnb ROI: N/A Traditional ROI: 0.32%
1 N Wade Rd Bennington, OK 1 N Wade Rd, Bennington, OK 74723 \| Other	N/A beds \| N/A baths \| N/A	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.28% Airbnb Rental Income: $null Traditional Rental Income: $902 Airbnb ROI: N/A Traditional ROI: 1.28%
269 N Shoe Make Rdg Bennington, OK 269 N Shoe Make Rdg, Bennington, OK 74723 \| Manufactured Home	4 beds \| 3 baths \| 2,016 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.62% Airbnb Rental Income: $null Traditional Rental Income: $2383 Airbnb ROI: N/A Traditional ROI: 1.62%
32 Rock House Rd Bennington, OK Discover this historical rustic home nestled in Bryan County, Oklahoma. Perfectly positio...	1 beds \| 2 baths \| 1,200 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.05% Airbnb Rental Income: $null Traditional Rental Income: $1753 Airbnb ROI: N/A Traditional ROI: 2.05%
3 Shady Grv Bennington, OK 3 Shady Grv, Bennington, OK 74723 \| Single Family Residential	2 beds \| 2 baths \| 1,300 sq.ft.	$1,870,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.01% Airbnb Rental Income: $null Traditional Rental Income: $1626 Airbnb ROI: N/A Traditional ROI: -1.01%
Wilson N Jones Bennington, OK Wilson N Jones, Bennington, OK 74723 \| Other	N/A beds \| N/A baths \| N/A	$280,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.23% Airbnb Rental Income: $null Traditional Rental Income: $916 Airbnb ROI: N/A Traditional ROI: 1.23%
1318 N Banty Rd Bennington, OK Embrace the hustle and bustle and embrace the quiet country life! Nestled in 18 secluded a...	3 beds \| 2 baths \| 1,216 sq.ft.	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.03% Airbnb Rental Income: $null Traditional Rental Income: $1805 Airbnb ROI: N/A Traditional ROI: 4.03%
1386 Wilson N Jones Rd Bennington, OK 1386 Wilson N Jones Rd, Bennington, OK 74723 \| Single Family Residential	3 beds \| 2 baths \| 1,648 sq.ft.	$229,500	Airbnb cash on cash: N/A Traditional cash on cash: 7.2% Airbnb Rental Income: $null Traditional Rental Income: $2067 Airbnb ROI: N/A Traditional ROI: 7.2%
105 Rock House Rd Bennington, OK 105 Rock House Rd, Bennington, OK 74723 \| Single Family Residential	4 beds \| 2 baths \| 3,538 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.14% Airbnb Rental Income: $null Traditional Rental Income: $2272 Airbnb ROI: N/A Traditional ROI: 0.14%
002 N Wade Rd Bennington, OK 002 N Wade Rd, Bennington, OK 74723 \| Other	N/A beds \| N/A baths \| N/A	$135,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.49% Airbnb Rental Income: $null Traditional Rental Income: $920 Airbnb ROI: N/A Traditional ROI: 4.49%

Real Estate investment in Bennington, OK

There are 18 properties for sale in the city of Bennington . The median list price in Bennington is $175,000 and the average price per square foot is $75. In June 2026, the average monthly cash on cash return in Bennington is 3.00%. The average monthly rental income in Bennington is $1,871.

Bennington, OK Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 18 investment properties available for sale in Bennington.

The ROI for Short-Term is higher than the Long-Term in Bennington with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Bennington, OK

4168 Armstrong Academy

Bennington, OK

3 beds | 1 baths | 2,056 sq.ft.

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.7%

Airbnb Rental Income: $null

Traditional Rental Income: $2604

Airbnb ROI: N/A

Traditional ROI: 1.7%

488 Rock House Rd

Bennington, OK

3 beds | N/A baths | 3,610 sq.ft.

$379,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.79%

Airbnb Rental Income: $null

Traditional Rental Income: $2013

Airbnb ROI: N/A

Traditional ROI: 3.79%

36953 Us Highway 70

Bennington, OK

4 beds | 2 baths | 2,256 sq.ft.

$489,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.39%

Airbnb Rental Income: $null

Traditional Rental Income: $2512

Airbnb ROI: N/A

Traditional ROI: 3.39%

37001 Us Hwy 70

Bennington, OK

3 beds | 2 baths | 2,064 sq.ft.

$469,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.03%

Airbnb Rental Income: $null

Traditional Rental Income: $2255

Airbnb ROI: N/A

Traditional ROI: 3.03%

699 Cox Ln

Bennington, OK

3 beds | 2 baths | 1,300 sq.ft.

$195,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.07%

Airbnb Rental Income: $null

Traditional Rental Income: $1937

Airbnb ROI: N/A

Traditional ROI: 8.07%

1965 Starlight Ln

Bennington, OK

3 beds | 2 baths | 1,792 sq.ft.

$385,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.05%

Airbnb Rental Income: $null

Traditional Rental Income: $2331

Airbnb ROI: N/A

Traditional ROI: 5.05%

36977 Hwy 70

Bennington, OK

6 beds | 4 baths | 4,400 sq.ft.

$823,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.5%

Airbnb Rental Income: $null

Traditional Rental Income: $3466

Airbnb ROI: N/A

Traditional ROI: 2.5%

240 Magnolia

Bennington, OK

3 beds | 3 baths | 4,040 sq.ft.

$2,555,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.87%

Airbnb Rental Income: $null

Traditional Rental Income: $2510

Airbnb ROI: N/A