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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
321 S Washington Street Chesterfield, IN Nestled on a quaint and charming street in Chesterfield, this utterly delightful 1915 bung...	2 beds \| 2 baths \| 877 sq.ft.	$144,900	Airbnb cash on cash: 2.02% Traditional cash on cash: 9.93% Airbnb Rental Income: $906 Traditional Rental Income: $1664 Airbnb ROI: 2.02% Traditional ROI: 9.93%
407 Crestview Court Chesterfield, IN Welcome to this beautifully updated ranch home offering modern comfort and convenience thr...	3 beds \| 1 baths \| 1,500 sq.ft.	$182,500	Airbnb cash on cash: 1.42% Traditional cash on cash: 9.26% Airbnb Rental Income: $850 Traditional Rental Income: $1881 Airbnb ROI: 1.42% Traditional ROI: 9.26%
66 Circle Drive Chesterfield, IN Nestled at 66 Circle DR, CHESTERFIELD, IN, this single-family residence in Madison County ...	3 beds \| 2 baths \| 1,437 sq.ft.	$159,900	Airbnb cash on cash: 0.78% Traditional cash on cash: 11.46% Airbnb Rental Income: $850 Traditional Rental Income: $2150 Airbnb ROI: 0.78% Traditional ROI: 11.46%
519 Hampton Lane Chesterfield, IN Nestled in the heart of Chesterfield, this charming 3-bedroom, 1-bath home has been comple...	3 beds \| 1 baths \| 1,372 sq.ft.	$150,000	Airbnb cash on cash: 0.8% Traditional cash on cash: 10.45% Airbnb Rental Income: $850 Traditional Rental Income: $1905 Airbnb ROI: 0.8% Traditional ROI: 10.45%
Investment Properties for Sale in Other Cities of Indiana
10655 Eric Court Fishers , IN Check this one out! Perfectly located on a private cul-de-sac, in a very desirable neighbo...	3 beds \| 3 baths \| 1,957 sq.ft.	$359,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 4.98% Airbnb Rental Income: $1452 Traditional Rental Income: $2299 Airbnb ROI: 1.19% Traditional ROI: 4.98%
824 E Minnesota Street Indianapolis , IN This home screams modern charm! Welcome to this updated 4 bedroom, 2 bath home in Bates-He...	4 beds \| 2 baths \| 2,122 sq.ft.	$370,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 5.01% Airbnb Rental Income: $954 Traditional Rental Income: $2267 Airbnb ROI: 0.22% Traditional ROI: 5.01%
15675 Wescott Drive Noblesville , IN Say goodbye to all the weekend yard chores. This Olthof home merges the convenience of con...	2 beds \| 2 baths \| 1,718 sq.ft.	$369,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 3.61% Airbnb Rental Income: $1345 Traditional Rental Income: $2230 Airbnb ROI: -0.14% Traditional ROI: 3.61%
201 Walnut Street Advance , IN Welcome home to this charming 2 bedroom, 2 bath property sitting on almost half an acre (....	2 beds \| 2 baths \| 1,056 sq.ft.	$184,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.58% Airbnb Rental Income: $null Traditional Rental Income: $1851 Airbnb ROI: N/A Traditional ROI: 8.58%
8660 Fawn Way McCordsville , IN Better than new! This beautifully updated home near Geist Reservoir features upgraded floo...	3 beds \| 3 baths \| 2,263 sq.ft.	$379,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.12% Airbnb Rental Income: $1186 Traditional Rental Income: $2283 Airbnb ROI: -0.05% Traditional ROI: 4.12%
1066 Reserve Way Indianapolis , IN Spacious 2 bedroom condo with vaulted ceilings located right in the heart of Broad Ripple....	2 beds \| 2 baths \| 2,000 sq.ft.	$340,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 4.11% Airbnb Rental Income: $1354 Traditional Rental Income: $2289 Airbnb ROI: -0.12% Traditional ROI: 4.11%
2028 Burch Drive Indianapolis , IN Charming Cape Cod Style home, just one block from Broad Ripple Park's tennis courts, trail...	4 beds \| 2 baths \| 2,289 sq.ft.	$310,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 6.26% Airbnb Rental Income: $1778 Traditional Rental Income: $2413 Airbnb ROI: 2.42% Traditional ROI: 6.26%
206 N Beville Avenue Indianapolis , IN Be the first to live in this fully renovated 5-bedroom, 3-bath home just minutes from the ...	5 beds \| 3 baths \| 2,850 sq.ft.	$270,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.84% Airbnb Rental Income: $null Traditional Rental Income: $2814 Airbnb ROI: N/A Traditional ROI: 8.84%
17 N Randolph Street Indianapolis , IN Step into this beautifully maintained classic Four Square home offering timeless charm wit...	3 beds \| 2 baths \| 1,822 sq.ft.	$249,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 6.44% Airbnb Rental Income: $815 Traditional Rental Income: $2041 Airbnb ROI: -0.15% Traditional ROI: 6.44%
2016 N Glenridge Drive Indianapolis , IN Charming "Updated" Bungalow will have you at Hello! This spacious 4-bedroom home offers un...	4 beds \| 1 baths \| 1,492 sq.ft.	$190,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $1205 Airbnb ROI: N/A Traditional ROI: 4.31%
1526 N Sherman Drive Indianapolis , IN Newly updated 1-bedroom, 1-bath home located right across from Brookside Park! Enjoy conve...	1 beds \| 1 baths \| 576 sq.ft.	$70,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 9.37% Airbnb Rental Income: $548 Traditional Rental Income: $872 Airbnb ROI: 0.67% Traditional ROI: 9.37%
6650 Page Boulevard #402 Indianapolis , IN Welcome home to this incredible corner-unit penthouse offering panoramic views and abundan...	3 beds \| 3 baths \| 2,738 sq.ft.	$550,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 1.68% Airbnb Rental Income: $1541 Traditional Rental Income: $2794 Airbnb ROI: -1.62% Traditional ROI: 1.68%
1444 E Elbert Street Indianapolis , IN This 2-bedroom, 1-bath bungalow offers the rare combination of a private, secluded lot wit...	2 beds \| 1 baths \| 912 sq.ft.	$180,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 3.84% Airbnb Rental Income: $1190 Traditional Rental Income: $1193 Airbnb ROI: 1.56% Traditional ROI: 3.84%
3822 Limelight Lane Whitestown , IN Nestled in Whitestown's desirable Walker Farms community, this 3-bedroom, 2.5-bath home of...	3 beds \| 3 baths \| 1,912 sq.ft.	$315,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 5.39% Airbnb Rental Income: $1530 Traditional Rental Income: $2195 Airbnb ROI: 1.65% Traditional ROI: 5.39%

Real Estate investment in Chesterfield, IN

There are 4 properties for sale in the city of Chesterfield . The median list price in Chesterfield is $154,950 and the average price per square foot is $119. In December 2025, the average monthly cash on cash return in Chesterfield is 10.00%. The average monthly rental income in Chesterfield is $1,893.

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

There are 4 investment properties available for sale in Chesterfield.

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

The ROI for Long-Term is higher than the Short-Term in Chesterfield with average rental income of $1,893.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterfield, IN

321 S Washington Street

Chesterfield, IN

2 beds | 2 baths | 877 sq.ft.

$144,900

Airbnb cash on cash: 2.02%

Traditional cash on cash: 9.93%

Airbnb Rental Income: $906

Traditional Rental Income: $1664

Airbnb ROI: 2.02%

Traditional ROI: 9.93%

407 Crestview Court

Chesterfield, IN

3 beds | 1 baths | 1,500 sq.ft.

$182,500

Airbnb cash on cash: 1.42%

Traditional cash on cash: 9.26%

Airbnb Rental Income: $850

Traditional Rental Income: $1881

Airbnb ROI: 1.42%

Traditional ROI: 9.26%

66 Circle Drive

Chesterfield, IN

3 beds | 2 baths | 1,437 sq.ft.

$159,900

Airbnb cash on cash: 0.78%

Traditional cash on cash: 11.46%

Airbnb Rental Income: $850

Traditional Rental Income: $2150

Airbnb ROI: 0.78%

Traditional ROI: 11.46%

519 Hampton Lane

Chesterfield, IN

3 beds | 1 baths | 1,372 sq.ft.

$150,000

Airbnb cash on cash: 0.8%

Traditional cash on cash: 10.45%

Airbnb Rental Income: $850

Traditional Rental Income: $1905

Airbnb ROI: 0.8%

Traditional ROI: 10.45%

Investment Properties for Sale in Other Cities of Indiana

Fishers , IN

3 beds | 3 baths | 1,957 sq.ft.

$359,000

Airbnb cash on cash: 1.19%

Traditional cash on cash: 4.98%

Airbnb Rental Income: $1452

Traditional Rental Income: $2299

Airbnb ROI: 1.19%

Traditional ROI: 4.98%

Indianapolis , IN

4 beds | 2 baths | 2,122 sq.ft.

$370,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 5.01%

Airbnb Rental Income: $954

Traditional Rental Income: $2267

Airbnb ROI: 0.22%

Traditional ROI: 5.01%

Noblesville , IN

2 beds | 2 baths | 1,718 sq.ft.

$369,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $1345

Traditional Rental Income: $2230

Airbnb ROI: -0.14%

Traditional ROI: 3.61%

Advance , IN

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

$184,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.58%

Airbnb Rental Income: $null

Traditional Rental Income: $1851

Airbnb ROI: N/A

Traditional ROI: 8.58%

McCordsville , IN

3 beds | 3 baths | 2,263 sq.ft.