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
812 E Washington Pittsfield, IL This stunning home is the epitome of modern living and comfort that is designed for both r...	4 beds \| 2 baths \| 1,965 sq.ft.	$269,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.93% Airbnb Rental Income: $null Traditional Rental Income: $2157 Airbnb ROI: N/A Traditional ROI: 5.93%
130 S Monroe St Pittsfield, IL Welcome to your dream home at 130 S Monroe St, Pittsfield, perfectly combining modern comf...	4 beds \| 2 baths \| 2,345 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.86% Airbnb Rental Income: $null Traditional Rental Income: $2937 Airbnb ROI: N/A Traditional ROI: 8.86%
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.	$239,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.44% Airbnb Rental Income: $null Traditional Rental Income: $2676 Airbnb ROI: N/A Traditional ROI: 9.44%
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 \| N/A	$134,500	Airbnb cash on cash: N/A Traditional cash on cash: 9.88% Airbnb Rental Income: $null Traditional Rental Income: $1593 Airbnb ROI: N/A Traditional ROI: 9.88%
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%
425 E North St Pittsfield, IL Spacious 4-bedroom, 2-bath home on a 0.55-acre corner lot with plenty of room inside and o...	4 beds \| 2 baths \| N/A	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.55% Airbnb Rental Income: $null Traditional Rental Income: $1770 Airbnb ROI: N/A Traditional ROI: 8.55%
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	$169,000	Airbnb cash on cash: 0.66% Traditional cash on cash: 8.38% Airbnb Rental Income: $921 Traditional Rental Income: $1823 Airbnb ROI: 0.66% Traditional ROI: 8.38%
210 W Crane St Pittsfield, IL 210 W Crane St, Pittsfield, IL 62363 \| Single Family Residential	3 beds \| 1 baths \| 1,404 sq.ft.	$135,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 9.21% Airbnb Rental Income: $921 Traditional Rental Income: $1703 Airbnb ROI: 0.54% Traditional ROI: 9.21%
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: -0.35% Traditional cash on cash: 7.63% Airbnb Rental Income: $921 Traditional Rental Income: $2380 Airbnb ROI: -0.35% Traditional ROI: 7.63%
615 N Memorial Pittsfield, IL This inviting one-story home offers comfortable living with flexible space and plenty of r...	2 beds \| 2 baths \| N/A	$159,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.68% Airbnb Rental Income: $null Traditional Rental Income: $1900 Airbnb ROI: N/A Traditional ROI: 8.68%
1802 Lakeview Heights Pittsfield, IL Charming and fully updated 2bed, 1bath home set on 2.18 acres within the Pittsfield city l...	2 beds \| 1 baths \| 1,078 sq.ft.	$189,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $1578 Airbnb ROI: N/A Traditional ROI: 6.02%
422 W Perry St Pittsfield, IL Adorable and updated 3 bedroom, 1 bath home with detached garage. This recently renovated ...	3 beds \| 1 baths \| 1,144 sq.ft.	$150,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 10% Airbnb Rental Income: $921 Traditional Rental Income: $1793 Airbnb ROI: 1.54% Traditional ROI: 10%
725 W Fayette Street Pittsfield, IL Located at 725 W Fayette St in Pittsfield, Illinois, this 1,040 square foot home offers a ...	2 beds \| 1 baths \| 2,080 sq.ft.	$150,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.35% Airbnb Rental Income: $null Traditional Rental Income: $1473 Airbnb ROI: N/A Traditional ROI: 7.35%
210 Crane St Pittsfield, IL 210 Crane St, Pittsfield, IL 63017 \| Single Family Residential	3 beds \| 1 baths \| 1,404 sq.ft.	$135,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 6.06% Airbnb Rental Income: $921 Traditional Rental Income: $1295 Airbnb ROI: 0.54% Traditional ROI: 6.06%

Real Estate investment in Pittsfield, IL

There are 20 properties for sale in the city of Pittsfield . The median list price in Pittsfield is $84,949 and the average price per square foot is $40. In August 2026, the average monthly cash on cash return in Pittsfield is 9.00%. The average monthly rental income in Pittsfield is $1,810.

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

There are 20 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 $1,810.

Your search for investment property begins and ends here

Investment Property for Sale in Pittsfield, IL

812 E Washington

Pittsfield, IL

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

$269,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.93%

Airbnb Rental Income: $null

Traditional Rental Income: $2157

Airbnb ROI: N/A

Traditional ROI: 5.93%

130 S Monroe St

Pittsfield, IL

4 beds | 2 baths | 2,345 sq.ft.

$249,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.86%

Airbnb Rental Income: $null

Traditional Rental Income: $2937

Airbnb ROI: N/A

Traditional ROI: 8.86%

316 N Monroe St

Pittsfield, IL

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

$239,900

Airbnb cash on cash: N/A

Traditional cash on cash: 9.44%

Airbnb Rental Income: $null

Traditional Rental Income: $2676

Airbnb ROI: N/A

Traditional ROI: 9.44%

124 S Illinois St.

Pittsfield, IL

2 beds | 2 baths | N/A

$134,500

Airbnb cash on cash: N/A

Traditional cash on cash: 9.88%

Airbnb Rental Income: $null

Traditional Rental Income: $1593

Airbnb ROI: N/A

Traditional ROI: 9.88%

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%

425 E North St

Pittsfield, IL

4 beds | 2 baths | N/A

$159,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.55%

Airbnb Rental Income: $null

Traditional Rental Income: $1770

Airbnb ROI: N/A

Traditional ROI: 8.55%

420 N Illinois St

Pittsfield, IL

3 beds | 1 baths | N/A

$169,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 8.38%

Airbnb Rental Income: $921

Traditional Rental Income: $1823

Airbnb ROI: 0.66%

Traditional ROI: 8.38%

210 W Crane St

Pittsfield, IL

3 beds | 1 baths | 1,404 sq.ft.

$135,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 9.21%

Airbnb Rental Income: $921

Traditional Rental Income: $1703

Airbnb ROI: 0.54%