Real Estate Investment Properties for Sale in Pittsfield, IL

Looking for investment property in Pittsfield, IL with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
226 S Jackson Street Pittsfield, IL This charming 3-bedroom, 2-bath home has plenty to offer! Step inside to find beautiful ha...	3 beds \| 2 baths \| 1,180 sq.ft.	$188,500	Airbnb cash on cash: 3.13% Traditional cash on cash: 8.51% Airbnb Rental Income: $1706 Traditional Rental Income: $2196 Airbnb ROI: 3.13% Traditional ROI: 8.51%
702 W Jefferson Street Pittsfield, IL Welcome to 702 W. Jefferson Street in Pittsfield! This well-maintained 3-bedroom, 1.5 bath...	3 beds \| 1 baths \| 1,248 sq.ft.	$159,900	Airbnb cash on cash: 5.38% Traditional cash on cash: 10.68% Airbnb Rental Income: $1706 Traditional Rental Income: $2043 Airbnb ROI: 5.38% Traditional ROI: 10.68%
316 N MONROE Street Pittsfield, IL Prepare to be impressed by the size and versatility of this beautifully maintained five-be...	5 beds \| 2 baths \| 3,389 sq.ft.	$219,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.41% Airbnb Rental Income: $null Traditional Rental Income: $2676 Airbnb ROI: N/A Traditional ROI: 10.41%
425 E NORTH Street Pittsfield, IL Enjoy the best of convenient living! This well-maintained home offers 4-5 bedrooms and 2 b...	4 beds \| 2 baths \| 2,028 sq.ft.	$144,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.51% Airbnb Rental Income: $null Traditional Rental Income: $1770 Airbnb ROI: N/A Traditional ROI: 9.51%
420 N Illinois St Pittsfield, IL Skip the renovations and move right into this beautifully updated 3-bedroom, 1-bathroom ho...	3 beds \| 1 baths \| N/A	$135,000	Airbnb cash on cash: 6.11% Traditional cash on cash: 10.66% Airbnb Rental Income: $1706 Traditional Rental Income: $1823 Airbnb ROI: 6.11% Traditional ROI: 10.66%
812 E Washington Street Pittsfield, IL Welcome to this impressive four-bedroom, two-bath home on beautiful East Washington Street...	4 beds \| 2 baths \| 1,965 sq.ft.	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $2296 Airbnb ROI: N/A Traditional ROI: 5.74%
327 W Adams Street Pittsfield, IL Built in 2020, this 2-bedroom, 1.5-bath duplex offers an open and functional floor plan wi...	2 beds \| 2 baths \| 1,008 sq.ft.	$180,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.35% Airbnb Rental Income: $null Traditional Rental Income: $1563 Airbnb ROI: N/A Traditional ROI: 5.35%
622 N Jackson Street Pittsfield, IL Welcome home to this charming 3-bedroom, 1-bath home with great curb appeal and plenty of ...	3 beds \| 1 baths \| 1,264 sq.ft.	$124,900	Airbnb cash on cash: 7.32% Traditional cash on cash: 10.46% Airbnb Rental Income: $1706 Traditional Rental Income: $1611 Airbnb ROI: 7.32% Traditional ROI: 10.46%
515 Piper Lane Pittsfield, IL Classic Traditional Home on Large Lot with Detached 2-Car Garage This 3-bedroom, 2-bathroo...	3 beds \| 2 baths \| 1,970 sq.ft.	$214,000	Airbnb cash on cash: 2.39% Traditional cash on cash: 8.24% Airbnb Rental Income: $1706 Traditional Rental Income: $2420 Airbnb ROI: 2.39% Traditional ROI: 8.24%
220 W Jefferson St. Pittsfield, IL Well-maintained 3-bedroom, 2-bath home built in 2021. Features a functional, open layout w...	3 beds \| 2 baths \| N/A	$260,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 6.78% Airbnb Rental Income: $1706 Traditional Rental Income: $2253 Airbnb ROI: 2.62% Traditional ROI: 6.78%
317 W Adams St Pittsfield, IL Turn-key perfection meets timeless charm in this beautifully renovated 4-bedroom, 2-bathro...	4 beds \| 2 baths \| 2,507 sq.ft.	$248,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.1% Airbnb Rental Income: $null Traditional Rental Income: $2498 Airbnb ROI: N/A Traditional ROI: 8.1%
660 S MEMORIAL Street Pittsfield, IL Convenience is key with this 3 bedroom, 1 bathroom home situated in an adorable Pittsfield...	3 beds \| 1 baths \| 1,042 sq.ft.	$119,000	Airbnb cash on cash: 7.47% Traditional cash on cash: 11.16% Airbnb Rental Income: $1706 Traditional Rental Income: $1657 Airbnb ROI: 7.47% Traditional ROI: 11.16%

Real Estate investment in Pittsfield, IL

There are 13 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $129,938 and the average price per square foot is $60. In November 2026, the average monthly cash on cash return in Pittsfield is 10.00%. The average monthly rental income in Pittsfield is $2,133.

Pittsfield, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 13 investment properties available for sale in Pittsfield.

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

The ROI for Short-Term is higher than the Long-Term in Pittsfield with average rental income of $1,706.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsfield, IL

226 S Jackson Street

Pittsfield, IL

3 beds | 2 baths | 1,180 sq.ft.

$188,500

Airbnb cash on cash: 3.13%

Traditional cash on cash: 8.51%

Airbnb Rental Income: $1706

Traditional Rental Income: $2196

Airbnb ROI: 3.13%

Traditional ROI: 8.51%

702 W Jefferson Street

Pittsfield, IL

3 beds | 1 baths | 1,248 sq.ft.

$159,900

Airbnb cash on cash: 5.38%

Traditional cash on cash: 10.68%

Airbnb Rental Income: $1706

Traditional Rental Income: $2043

Airbnb ROI: 5.38%

Traditional ROI: 10.68%

316 N MONROE Street

Pittsfield, IL

5 beds | 2 baths | 3,389 sq.ft.

$219,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.41%

Airbnb Rental Income: $null

Traditional Rental Income: $2676

Airbnb ROI: N/A

Traditional ROI: 10.41%

425 E NORTH Street

Pittsfield, IL

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

$144,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.51%

Airbnb Rental Income: $null

Traditional Rental Income: $1770

Airbnb ROI: N/A

Traditional ROI: 9.51%

420 N Illinois St

Pittsfield, IL

3 beds | 1 baths | N/A

$135,000

Airbnb cash on cash: 6.11%

Traditional cash on cash: 10.66%

Airbnb Rental Income: $1706

Traditional Rental Income: $1823

Airbnb ROI: 6.11%

Traditional ROI: 10.66%

812 E Washington Street

Pittsfield, IL

4 beds | 2 baths | 1,965 sq.ft.

$259,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.74%

Airbnb Rental Income: $null

Traditional Rental Income: $2296

Airbnb ROI: N/A

Traditional ROI: 5.74%

327 W Adams Street

Pittsfield, IL

2 beds | 2 baths | 1,008 sq.ft.

$180,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.35%

Airbnb Rental Income: $null

Traditional Rental Income: $1563

Airbnb ROI: N/A

Traditional ROI: 5.35%

622 N Jackson Street

Pittsfield, IL

3 beds | 1 baths | 1,264 sq.ft.

$124,900

Airbnb cash on cash: 7.32%

Traditional cash on cash: 10.46%

Airbnb Rental Income: $1706

Traditional Rental Income: $1611

Airbnb ROI: 7.32%