Real Estate Investment Properties for Sale in Chesterfield, IN

Looking for investment property in Chesterfield, IN with high ROI ?

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
312 North St Chesterfield, IN Your home search is over! Check out this wonderful home built in 2009 with over 1600 sqft ...	4 beds \| 2 baths \| 1,606 sq.ft.	$279,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.47% Airbnb Rental Income: $null Traditional Rental Income: $2227 Airbnb ROI: N/A Traditional ROI: 6.47%
1023 Avalon Ln Chesterfield, IN Discover the charm of 1023 Avalon LN, a captivating single-family residence in Chesterfiel...	4 beds \| 1 baths \| 1,944 sq.ft.	$240,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.95% Airbnb Rental Income: $null Traditional Rental Income: $2542 Airbnb ROI: N/A Traditional ROI: 8.95%
318 Vasbinder Dr Chesterfield, IN Welcome home to this charming 3-4 bedroom property with incredible curb appeal, lush lands...	3 beds \| 1 baths \| 1,561 sq.ft.	$235,500	Airbnb cash on cash: -0.16% Traditional cash on cash: 10.23% Airbnb Rental Income: $667 Traditional Rental Income: $2682 Airbnb ROI: -0.16% Traditional ROI: 10.23%
514 Ellerdale Rd Chesterfield, IN Welcome home to this 3-bedroom property offering the perfect blend of small-town charm and...	3 beds \| 1 baths \| 900 sq.ft.	$120,900	Airbnb cash on cash: 0.85% Traditional cash on cash: 10.59% Airbnb Rental Income: $667 Traditional Rental Income: $1502 Airbnb ROI: 0.85% Traditional ROI: 10.59%
225 North St Chesterfield, IN 225 North St, Anderson, IN 46017 \| Single Family Residential	3 beds \| 1 baths \| 904 sq.ft.	$179,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 6.05% Airbnb Rental Income: $667 Traditional Rental Income: $1443 Airbnb ROI: -0.24% Traditional ROI: 6.05%
113 Mulberry Chesterfield, IN This Bi Level home features the kitchen (with a walk out covered back deck) , (the living ...	3 beds \| 2 baths \| 1,536 sq.ft.	$193,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 9.71% Airbnb Rental Income: $667 Traditional Rental Income: $2174 Airbnb ROI: -0.15% Traditional ROI: 9.71%
3087 S 380 E Chesterfield, IN 3087 S 380 E, Chesterfield, IN 46017 \| Single Family Residential	4 beds \| 2 baths \| 1,590 sq.ft.	$410,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.6% Airbnb Rental Income: $null Traditional Rental Income: $2184 Airbnb ROI: N/A Traditional ROI: 3.6%
106 Eastman Road Chesterfield, IN Charming 3 bedroom, 1 bath in Chesterfield. The property features a private yard, offering...	3 beds \| 1 baths \| 864 sq.ft.	$144,900	Airbnb cash on cash: 0.51% Traditional cash on cash: 8.34% Airbnb Rental Income: $667 Traditional Rental Income: $1454 Airbnb ROI: 0.51% Traditional ROI: 8.34%

Real Estate investment in Chesterfield, IN

There are 8 properties for sale in the city of Chesterfield . The median list price in Chesterfield is $140,916 and the average price per square foot is $54. In July 2026, the average monthly cash on cash return in Chesterfield is 9.00%. The average monthly rental income in Chesterfield is $2,179.

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

There are 8 investment properties available for sale in Chesterfield.

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

The ROI for Short-Term is higher than the Long-Term in Chesterfield with average rental income of $667.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterfield, IN

312 North St

Chesterfield, IN

4 beds | 2 baths | 1,606 sq.ft.

$279,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.47%

Airbnb Rental Income: $null

Traditional Rental Income: $2227

Airbnb ROI: N/A

Traditional ROI: 6.47%

1023 Avalon Ln

Chesterfield, IN

4 beds | 1 baths | 1,944 sq.ft.

$240,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.95%

Airbnb Rental Income: $null

Traditional Rental Income: $2542

Airbnb ROI: N/A

Traditional ROI: 8.95%

318 Vasbinder Dr

Chesterfield, IN

3 beds | 1 baths | 1,561 sq.ft.

$235,500

Airbnb cash on cash: -0.16%

Traditional cash on cash: 10.23%

Airbnb Rental Income: $667

Traditional Rental Income: $2682

Airbnb ROI: -0.16%

Traditional ROI: 10.23%

514 Ellerdale Rd

Chesterfield, IN

3 beds | 1 baths | 900 sq.ft.

$120,900

Airbnb cash on cash: 0.85%

Traditional cash on cash: 10.59%

Airbnb Rental Income: $667

Traditional Rental Income: $1502

Airbnb ROI: 0.85%

Traditional ROI: 10.59%

225 North St

Chesterfield, IN

3 beds | 1 baths | 904 sq.ft.

$179,900

Airbnb cash on cash: -0.24%

Traditional cash on cash: 6.05%

Airbnb Rental Income: $667

Traditional Rental Income: $1443

Airbnb ROI: -0.24%

Traditional ROI: 6.05%

113 Mulberry

Chesterfield, IN

3 beds | 2 baths | 1,536 sq.ft.

$193,000

Airbnb cash on cash: -0.15%

Traditional cash on cash: 9.71%

Airbnb Rental Income: $667

Traditional Rental Income: $2174

Airbnb ROI: -0.15%

Traditional ROI: 9.71%

3087 S 380 E

Chesterfield, IN

4 beds | 2 baths | 1,590 sq.ft.

$410,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.6%

Airbnb Rental Income: $null

Traditional Rental Income: $2184

Airbnb ROI: N/A

Traditional ROI: 3.6%

106 Eastman Road

Chesterfield, IN

3 beds | 1 baths | 864 sq.ft.

$144,900

Airbnb cash on cash: 0.51%

Traditional cash on cash: 8.34%

Airbnb Rental Income: $667

Traditional Rental Income: $1454

Airbnb ROI: 0.51%