Real Estate Investment Properties for Sale in Chester, SD

Looking for investment property in Chester, SD with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
24105 461st Ave Chester, SD Only 3 miles South of Lake Madison, Lake Golf Course and Restaurant. Within 35 miles from ...	4 beds \| 6 baths \| 4,424 sq.ft.	$899,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.44% Airbnb Rental Income: $null Traditional Rental Income: $6043 Airbnb ROI: N/A Traditional ROI: 5.44%
201 2nd Ave Chester, SD Enjoy the perfect blend of country living and city convenience with this beautifully maint...	2 beds \| 3 baths \| 2,400 sq.ft.	$489,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.77% Airbnb Rental Income: $2030 Traditional Rental Income: $2658 Airbnb ROI: 1.24% Traditional ROI: 3.77%
23866 464th Ave Chester, SD *NEW PRICE* Enjoy peaceful country living with this beautifully updated ranch-style ho...	3 beds \| 2 baths \| 2,444 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.27% Airbnb Rental Income: $null Traditional Rental Income: $2571 Airbnb ROI: N/A Traditional ROI: 3.27%
Investment Properties for Sale in Other Cities of South-dakota
2020 S Lawson Street Aberdeen , SD This 4-bedroom, 2-bathroom home built in 2015 has everything you've been looking for - and...	4 beds \| 2 baths \| 2,384 sq.ft.	$364,900	Airbnb cash on cash: 5.01% Traditional cash on cash: 3.97% Airbnb Rental Income: $3348 Traditional Rental Income: $2244 Airbnb ROI: 5.01% Traditional ROI: 3.97%
1940 Meadowlark Ln Huron , SD Welcome to easy living in this spacious 3-bedroom, 2-bath condo featuring an open-concept ...	3 beds \| 2 baths \| 1,210 sq.ft.	$139,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.7% Airbnb Rental Income: $null Traditional Rental Income: $1551 Airbnb ROI: N/A Traditional ROI: 8.7%
24799 457th Ave Colton , SD It's time... time to own your own piece of land. Here's your opportunity to breathe with t...	2 beds \| 1 baths \| 1,108 sq.ft.	$239,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.28% Airbnb Rental Income: $null Traditional Rental Income: $1609 Airbnb ROI: N/A Traditional ROI: 5.28%
528 W Bailey St Sioux Falls , SD Cozy ranch style home with 2 bedrooms, 1 full bath and tandem 14 x32 double garage. Update...	2 beds \| 1 baths \| 950 sq.ft.	$179,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 5.49% Airbnb Rental Income: $777 Traditional Rental Income: $1366 Airbnb ROI: 0.19% Traditional ROI: 5.49%
845 Madison Blvd SE Huron , SD Welcome to this well-maintained 3-bed, 2-bath home, located in a quiet, friendly neighborh...	3 beds \| 2 baths \| 2,028 sq.ft.	$247,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.48% Airbnb Rental Income: $null Traditional Rental Income: $2371 Airbnb ROI: N/A Traditional ROI: 7.48%
3017 S Keyrell Dr Sioux Falls , SD This beautifully maintained split foyer home features 5 bedrooms, 3 bathrooms, and a spaci...	5 beds \| 3 baths \| 1,956 sq.ft.	$410,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 5.25% Airbnb Rental Income: $1430 Traditional Rental Income: $2968 Airbnb ROI: 0.14% Traditional ROI: 5.25%
316 W Evergreen Dr Brandon , SD Looking for space, privacy, and a great location? Check out this 3-bedroom split-level hom...	3 beds \| 2 baths \| 1,986 sq.ft.	$324,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.96% Airbnb Rental Income: $null Traditional Rental Income: $2503 Airbnb ROI: N/A Traditional ROI: 5.96%
1601 E Keystone Dr Brandon , SD Here's a 4 bed, 2 bath, 2 car attached garage, in one of the nicest neighborhoods in Brand...	4 beds \| 2 baths \| 2,002 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.26% Airbnb Rental Income: $null Traditional Rental Income: $2569 Airbnb ROI: N/A Traditional ROI: 5.26%
5809 W Oakcrest Dr Sioux Falls , SD From the moment you walk in, the layout feels right. This home offers the kind of space th...	3 beds \| 2 baths \| 1,514 sq.ft.	$315,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 5.36% Airbnb Rental Income: $1083 Traditional Rental Income: $2129 Airbnb ROI: 0.59% Traditional ROI: 5.36%
1378 Iowa Ave SE Huron , SD Cozy & Inviting! This 2-bedroom, 1-bath home offers comfort and charm with an attached sin...	2 beds \| 1 baths \| 1,792 sq.ft.	$160,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.26% Airbnb Rental Income: $null Traditional Rental Income: $1405 Airbnb ROI: N/A Traditional ROI: 6.26%
806 E Chestnut St Harrisburg , SD Welcome home! This 4 bed, 3 bath, 3 stall garage ranch home in Harrisburg is sure to impre...	4 beds \| 3 baths \| 2,328 sq.ft.	$379,900	Airbnb cash on cash: -0.23% Traditional cash on cash: 5.47% Airbnb Rental Income: $1182 Traditional Rental Income: $2829 Airbnb ROI: -0.23% Traditional ROI: 5.47%
1506 SE 3rd Avenue Aberdeen , SD Spacious 4 bedroom, 2.5 bath with many updates including kitchen; appliances; main floor b...	4 beds \| 3 baths \| 2,452 sq.ft.	$265,000	Airbnb cash on cash: 7.93% Traditional cash on cash: 9.75% Airbnb Rental Income: $3348 Traditional Rental Income: $3056 Airbnb ROI: 7.93% Traditional ROI: 9.75%
464 Nesbitt Drive Mina , SD WALKOUT TO A TASTE OF PARADISE! Classy remodeling, recent updates, 3 large BEDROOMS , And ...	3 beds \| 2 baths \| 1,920 sq.ft.	$449,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 4.19% Airbnb Rental Income: $2882 Traditional Rental Income: $2500 Airbnb ROI: 3.51% Traditional ROI: 4.19%
814 E 7th St Dell Rapids , SD Enjoy the charm of small-town living at an affordable price! This inviting 1.5-story home ...	3 beds \| 1 baths \| 1,082 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.54% Airbnb Rental Income: $null Traditional Rental Income: $1075 Airbnb ROI: N/A Traditional ROI: 3.54%
601 S Prairie Ave Sioux Falls , SD Welcome to your next homeâfull of charm, character, and modern comforts! From the momen...	3 beds \| 1 baths \| 1,317 sq.ft.	$227,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 5.48% Airbnb Rental Income: $1115 Traditional Rental Income: $1674 Airbnb ROI: 1.15% Traditional ROI: 5.48%

Real Estate investment in Chester, SD

There are 3 properties for sale in the city of Chester . The median list price in Chester is $539,900 and the average price per square foot is $175. In September 2025, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,658.

Chester, SD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3 investment properties available for sale in Chester.

In 2025, the best neighborhood to buy investment property is Chester.

The ROI for Long-Term is higher than the Short-Term in Chester with average rental income of $2,658.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, SD

24105 461st Ave

Chester, SD

4 beds | 6 baths | 4,424 sq.ft.

$899,500

Airbnb cash on cash: N/A

Traditional cash on cash: 5.44%

Airbnb Rental Income: $null

Traditional Rental Income: $6043

Airbnb ROI: N/A

Traditional ROI: 5.44%

201 2nd Ave

Chester, SD

2 beds | 3 baths | 2,400 sq.ft.

$489,900

Airbnb cash on cash: 1.24%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $2030

Traditional Rental Income: $2658

Airbnb ROI: 1.24%

Traditional ROI: 3.77%

23866 464th Ave

Chester, SD

3 beds | 2 baths | 2,444 sq.ft.

$539,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.27%

Airbnb Rental Income: $null

Traditional Rental Income: $2571

Airbnb ROI: N/A

Traditional ROI: 3.27%

Investment Properties for Sale in Other Cities of South-dakota

Aberdeen , SD

4 beds | 2 baths | 2,384 sq.ft.

$364,900

Airbnb cash on cash: 5.01%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $3348

Traditional Rental Income: $2244

Airbnb ROI: 5.01%

Traditional ROI: 3.97%

Huron , SD

3 beds | 2 baths | 1,210 sq.ft.

$139,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.7%

Airbnb Rental Income: $null

Traditional Rental Income: $1551

Airbnb ROI: N/A

Traditional ROI: 8.7%

Colton , SD

2 beds | 1 baths | 1,108 sq.ft.

$239,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.28%

Airbnb Rental Income: $null

Traditional Rental Income: $1609

Airbnb ROI: N/A

Traditional ROI: 5.28%

Sioux Falls , SD

2 beds | 1 baths | 950 sq.ft.

$179,900

Airbnb cash on cash: 0.19%

Traditional cash on cash: 5.49%

Airbnb Rental Income: $777

Traditional Rental Income: $1366

Airbnb ROI: 0.19%

Traditional ROI: 5.49%

Huron , SD

3 beds | 2 baths | 2,028 sq.ft.

$247,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.48%

Airbnb Rental Income: $null

Traditional Rental Income: $2371

Airbnb ROI: N/A

Traditional ROI: 7.48%

Sioux Falls , SD

5 beds | 3 baths | 1,956 sq.ft.

$410,000