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
220 E Fayette St Pittsfield, IL Welcome to this beautifully remodeled home that perfectly blends timeless character with m...	3 beds \| 2 baths \| 1,864 sq.ft.	$239,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 7.63% Airbnb Rental Income: $1770 Traditional Rental Income: $2380 Airbnb ROI: 2.79% Traditional ROI: 7.63%
316 N. Monroe St Pittsfield, IL Experience the timeless beauty of this 1890 Victorian home, where historic character meets...	4 beds \| 2 baths \| 3,082 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.68% Airbnb Rental Income: $null Traditional Rental Income: $2676 Airbnb ROI: N/A Traditional ROI: 8.68%
1110 Lowry St. Pittsfield, IL This immaculate, move-in-ready two-story home offers 1,900 square feet of pristine living ...	4 beds \| 3 baths \| 1,900 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.76% Airbnb Rental Income: $null Traditional Rental Income: $2842 Airbnb ROI: N/A Traditional ROI: 7.76%
1401 E. Washington St Pittsfield, IL 1401 E. Washington St., Pittsfield, IL 62363 5 Bedrooms \| 3 Full Baths \| 2 Half Baths \| 6...	5 beds \| 5 baths \| 3,442 sq.ft.	$429,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.74% Airbnb Rental Income: $null Traditional Rental Income: $6116 Airbnb ROI: N/A Traditional ROI: 11.74%
1241 Sunset Dr. Pittsfield, IL Well-maintained 2-bedroom, 2-bath brick ranch located on a 1/2-acre lot in a quiet cul-de-...	2 beds \| 2 baths \| 1,289 sq.ft.	$220,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.06% Airbnb Rental Income: $null Traditional Rental Income: $1821 Airbnb ROI: N/A Traditional ROI: 5.06%
124 S. Illinois St. Pittsfield, IL What a beautiful home just minutes from downtown! This fully updated, move-in ready proper...	2 beds \| 2 baths \| 887 sq.ft.	$137,500	Airbnb cash on cash: N/A Traditional cash on cash: 9.65% Airbnb Rental Income: $null Traditional Rental Income: $1593 Airbnb ROI: N/A Traditional ROI: 9.65%
418 E. Fayette St. Pittsfield, IL This charming two-bedroom, one-bath home offers comfort, convenience, and great potential ...	2 beds \| 1 baths \| N/A	$122,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.27% Airbnb Rental Income: $null Traditional Rental Income: $1423 Airbnb ROI: N/A Traditional ROI: 9.27%
913 N. Orchard Pittsfield, IL This move-in ready ranch-style 1,040 s.f. home offers comfort and convenience. Featuring 3...	3 beds \| 2 baths \| 1,040 sq.ft.	$179,500	Airbnb cash on cash: 4.51% Traditional cash on cash: 7.57% Airbnb Rental Income: $1770 Traditional Rental Income: $1810 Airbnb ROI: 4.51% Traditional ROI: 7.57%
1033 W. Lowry Street Pittsfield, IL Welcome home to this beautifully updated ranch-style retreat that perfectly balances indoo...	3 beds \| 1 baths \| 1,625 sq.ft.	$260,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 6.26% Airbnb Rental Income: $1770 Traditional Rental Income: $1977 Airbnb ROI: 3.44% Traditional ROI: 6.26%
402 W WASHINGTON Street Pittsfield, IL Whether you're a growing family needing more space or an Abe Lincoln fanatic, this remarka...	4 beds \| 2 baths \| 2,576 sq.ft.	$230,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.89% Airbnb Rental Income: $null Traditional Rental Income: $2595 Airbnb ROI: N/A Traditional ROI: 9.89%
26438 Lake Pittsfield Drive Pittsfield, IL Nestled on nearly two private acres at Lake Pittsfield, this inviting 3-bedroom, 2-bath ho...	3 beds \| 2 baths \| 1,378 sq.ft.	$269,000	Airbnb cash on cash: 2.56% Traditional cash on cash: 5.18% Airbnb Rental Income: $1770 Traditional Rental Income: $1950 Airbnb ROI: 2.56% Traditional ROI: 5.18%

Real Estate investment in Pittsfield, IL

There are 12 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $279,900 and the average price per square foot is $129. In May 2026, the average monthly cash on cash return in Pittsfield is 9.00%. The average monthly rental income in Pittsfield is $2,214.

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

There are 12 investment properties available for sale in Pittsfield.

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

The ROI for Long-Term is higher than the Short-Term in Pittsfield with average rental income of $2,214.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsfield, IL

220 E Fayette St

Pittsfield, IL

3 beds | 2 baths | 1,864 sq.ft.

$239,000

Airbnb cash on cash: 2.79%

Traditional cash on cash: 7.63%

Airbnb Rental Income: $1770

Traditional Rental Income: $2380

Airbnb ROI: 2.79%

Traditional ROI: 7.63%

316 N. Monroe St

Pittsfield, IL

4 beds | 2 baths | 3,082 sq.ft.

$259,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.68%

Airbnb Rental Income: $null

Traditional Rental Income: $2676

Airbnb ROI: N/A

Traditional ROI: 8.68%

1110 Lowry St.

Pittsfield, IL

4 beds | 3 baths | 1,900 sq.ft.

$265,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.76%

Airbnb Rental Income: $null

Traditional Rental Income: $2842

Airbnb ROI: N/A

Traditional ROI: 7.76%

1401 E. Washington St

Pittsfield, IL

5 beds | 5 baths | 3,442 sq.ft.

$429,000

Airbnb cash on cash: N/A

Traditional cash on cash: 11.74%

Airbnb Rental Income: $null

Traditional Rental Income: $6116

Airbnb ROI: N/A

Traditional ROI: 11.74%

1241 Sunset Dr.

Pittsfield, IL

2 beds | 2 baths | 1,289 sq.ft.

$220,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.06%

Airbnb Rental Income: $null

Traditional Rental Income: $1821

Airbnb ROI: N/A

Traditional ROI: 5.06%

124 S. Illinois St.

Pittsfield, IL

2 beds | 2 baths | 887 sq.ft.

$137,500

Airbnb cash on cash: N/A

Traditional cash on cash: 9.65%

Airbnb Rental Income: $null

Traditional Rental Income: $1593

Airbnb ROI: N/A

Traditional ROI: 9.65%

418 E. Fayette St.

Pittsfield, IL

2 beds | 1 baths | N/A

$122,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.27%

Airbnb Rental Income: $null

Traditional Rental Income: $1423

Airbnb ROI: N/A

Traditional ROI: 9.27%

913 N. Orchard

Pittsfield, IL

3 beds | 2 baths | 1,040 sq.ft.

$179,500

Airbnb cash on cash: 4.51%

Traditional cash on cash: 7.57%

Airbnb Rental Income: $1770

Traditional Rental Income: $1810

Airbnb ROI: 4.51%