Real Estate Investment Properties for Sale in Montgomery, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3108 Manchester Drive MONTGOMERY, IL Welcome to your dream home in Huntington Chase, where exceptional craftsmanship and though...	3 beds \| 3 baths \| 1,875 sq.ft.	$410,000	Airbnb cash on cash: -2.04% Traditional cash on cash: 2.22% Airbnb Rental Income: $911 Traditional Rental Income: $2209 Airbnb ROI: -2.04% Traditional ROI: 2.22%
1808 Candlelight Circle MONTGOMERY, IL This stunning end-unit townhome welcomes you with a dramatic vaulted foyer and elegant wro...	2 beds \| 3 baths \| 1,754 sq.ft.	$290,000	Airbnb cash on cash: -2.59% Traditional cash on cash: 4.88% Airbnb Rental Income: $768 Traditional Rental Income: $2490 Airbnb ROI: -2.59% Traditional ROI: 4.88%
2214 Andrew Trail MONTGOMERY, IL Welcome to this stunning 4 bedroom, 2.5 bath and attached 2 car garage. The updated kitche...	4 beds \| 3 baths \| 2,072 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.52% Airbnb Rental Income: $null Traditional Rental Income: $2895 Airbnb ROI: N/A Traditional ROI: 4.52%
1417 Manning Ave MONTGOMERY, IL Absolutely gorgeous townhome in Fieldstone Place! This Beautifull spacious (end unit) town...	2 beds \| 2 baths \| 1,670 sq.ft.	$289,900	Airbnb cash on cash: -1.77% Traditional cash on cash: 6.34% Airbnb Rental Income: $768 Traditional Rental Income: $2665 Airbnb ROI: -1.77% Traditional ROI: 6.34%
215 Fernwood Road MONTGOMERY, IL Welcome to Your Dream Home in Boulder Hill! This rare Cape Cod-style property offers excep...	5 beds \| 3 baths \| 1,976 sq.ft.	$345,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 5.68% Airbnb Rental Income: $1707 Traditional Rental Income: $3015 Airbnb ROI: 0.18% Traditional ROI: 5.68%
19 Wyndham Drive MONTGOMERY, IL Welcome to this fantastic 4-bedroom, 1.5-bathroom raised ranch in a great Montgomery spot!...	3 beds \| 2 baths \| 1,600 sq.ft.	$300,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 5.28% Airbnb Rental Income: $911 Traditional Rental Income: $2423 Airbnb ROI: -1.28% Traditional ROI: 5.28%
2926 Astor Lane MONTGOMERY, IL	3 beds \| 3 baths \| 1,764 sq.ft.	$324,900	Airbnb cash on cash: -1.01% Traditional cash on cash: 5.59% Airbnb Rental Income: $911 Traditional Rental Income: $2585 Airbnb ROI: -1.01% Traditional ROI: 5.59%
1850 Candlelight Cir MONTGOMERY, IL This end unit townhouse in Yorkville District 115 is a true gem, offering three spacious b...	3 beds \| 2 baths \| 1,754 sq.ft.	$309,900	Airbnb cash on cash: -1.62% Traditional cash on cash: 4.31% Airbnb Rental Income: $911 Traditional Rental Income: $2300 Airbnb ROI: -1.62% Traditional ROI: 4.31%
2717 AVALON Lane MONTGOMERY, IL Discover this beautifully renovated and move-in-ready home, perfectly situated just one bl...	4 beds \| 3 baths \| 2,576 sq.ft.	$449,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.81% Airbnb Rental Income: $null Traditional Rental Income: $3020 Airbnb ROI: N/A Traditional ROI: 3.81%
3014 Shetland Ln MONTGOMERY, IL Step inside this 5 bedroom and 3.5 bathroom home. The open-concept main level shines with ...	5 beds \| 3 baths \| 2,459 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $3231 Airbnb ROI: N/A Traditional ROI: 4.61%
117 Boulder Hill Pass unit: 117 #117 MONTGOMERY, IL Welcome to 117 Boulder Hill Pass, a beautifully updated ranch home in "The Gardens", a pre...	2 beds \| 1 baths \| 1,000 sq.ft.	$224,900	Airbnb cash on cash: -2.33% Traditional cash on cash: 3.59% Airbnb Rental Income: $768 Traditional Rental Income: $1712 Airbnb ROI: -2.33% Traditional ROI: 3.59%
2254 Gallant Fox Circle MONTGOMERY, IL Welcome home! This roomy townhome is just what you've been waiting for. Large kitchen with...	3 beds \| 3 baths \| 1,620 sq.ft.	$290,000	Airbnb cash on cash: -2.18% Traditional cash on cash: 4.78% Airbnb Rental Income: $911 Traditional Rental Income: $2473 Airbnb ROI: -2.18% Traditional ROI: 4.78%
119 Garden Drive MONTGOMERY, IL Welcome to The Gardens: Charming Senior Living Discover your new home in this delightf...	2 beds \| 2 baths \| 1,142 sq.ft.	$244,900	Airbnb cash on cash: -2.42% Traditional cash on cash: 4.4% Airbnb Rental Income: $768 Traditional Rental Income: $2027 Airbnb ROI: -2.42% Traditional ROI: 4.4%
28 Seneca Drive MONTGOMERY, IL 2026 IS HERE AND JUST IN TIME TO SEE THIS 4 BEDROOM/ 2 BATH/ 2 CAR GARAGE IN MONTGOMERY! S...	4 beds \| 2 baths \| N/A	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.46% Airbnb Rental Income: $null Traditional Rental Income: $2715 Airbnb ROI: N/A Traditional ROI: 5.46%
9 Cebold Drive MONTGOMERY, IL Spacious Split-Level 4-Bedroom Home. Discover the perfect blend of space, style, and comfo...	4 beds \| 3 baths \| 2,253 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.34% Airbnb Rental Income: $null Traditional Rental Income: $3133 Airbnb ROI: N/A Traditional ROI: 5.34%
1341 Hinckley Street MONTGOMERY, IL Charming 4-bedroom home offering a functional layout and great everyday living space. The ...	4 beds \| 1 baths \| 825 sq.ft.	$205,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.01% Airbnb Rental Income: $null Traditional Rental Income: $1964 Airbnb ROI: N/A Traditional ROI: 7.01%
1931 STEPHEN Drive MONTGOMERY, IL Welcome to your new favorite place to be. This updated ranch has plenty to offer. The main...	3 beds \| 1 baths \| 936 sq.ft.	$295,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 3.69% Airbnb Rental Income: $911 Traditional Rental Income: $1745 Airbnb ROI: -0.54% Traditional ROI: 3.69%
46 Ingleshire Road MONTGOMERY, IL The one you've been waiting for! This 3 bedroom, 1 bath, Boulder Hill ranch home has a det...	3 beds \| 1 baths \| 1,428 sq.ft.	$325,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 2.64% Airbnb Rental Income: $911 Traditional Rental Income: $1815 Airbnb ROI: -1.43% Traditional ROI: 2.64%
1855 Grandview Place MONTGOMERY, IL Welcome home to this bright and charming 3 bedroom, 1.5 bathroom townhome, offering comfor...	2 beds \| 2 baths \| 1,434 sq.ft.	$260,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 5.54% Airbnb Rental Income: $768 Traditional Rental Income: $2172 Airbnb ROI: -1.47% Traditional ROI: 5.54%
2358 Ferdinand Lane MONTGOMERY, IL	4 beds \| 3 baths \| 3,240 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $3122 Airbnb ROI: N/A Traditional ROI: 3.22%

Real Estate investment in Montgomery, IL

There are 21 properties for sale in the city of Montgomery . The median list price in Montgomery is $266,500 and the average price per square foot is $113. In February 2026, the average monthly cash on cash return in Montgomery is 5.00%. The average monthly rental income in Montgomery is $2,490.

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

There are 21 investment properties available for sale in Montgomery.

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

The ROI for Long-Term is higher than the Short-Term in Montgomery with average rental income of $2,490.

Your search for investment property begins and ends here

Investment Property for Sale in Montgomery, IL

3108 Manchester Drive

MONTGOMERY, IL

3 beds | 3 baths | 1,875 sq.ft.

$410,000

Airbnb cash on cash: -2.04%

Traditional cash on cash: 2.22%

Airbnb Rental Income: $911

Traditional Rental Income: $2209

Airbnb ROI: -2.04%

Traditional ROI: 2.22%

1808 Candlelight Circle

MONTGOMERY, IL

2 beds | 3 baths | 1,754 sq.ft.

$290,000

Airbnb cash on cash: -2.59%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $768

Traditional Rental Income: $2490

Airbnb ROI: -2.59%

Traditional ROI: 4.88%

2214 Andrew Trail

MONTGOMERY, IL

4 beds | 3 baths | 2,072 sq.ft.

$390,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.52%

Airbnb Rental Income: $null

Traditional Rental Income: $2895

Airbnb ROI: N/A

Traditional ROI: 4.52%

1417 Manning Ave

MONTGOMERY, IL

2 beds | 2 baths | 1,670 sq.ft.

$289,900

Airbnb cash on cash: -1.77%

Traditional cash on cash: 6.34%

Airbnb Rental Income: $768

Traditional Rental Income: $2665

Airbnb ROI: -1.77%

Traditional ROI: 6.34%

215 Fernwood Road

MONTGOMERY, IL

5 beds | 3 baths | 1,976 sq.ft.

$345,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $1707

Traditional Rental Income: $3015

Airbnb ROI: 0.18%

Traditional ROI: 5.68%

19 Wyndham Drive

MONTGOMERY, IL

3 beds | 2 baths | 1,600 sq.ft.

$300,000

Airbnb cash on cash: -1.28%

Traditional cash on cash: 5.28%

Airbnb Rental Income: $911

Traditional Rental Income: $2423

Airbnb ROI: -1.28%

Traditional ROI: 5.28%

2926 Astor Lane

MONTGOMERY, IL

3 beds | 3 baths | 1,764 sq.ft.

$324,900

Airbnb cash on cash: -1.01%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $911

Traditional Rental Income: $2585

Airbnb ROI: -1.01%

Traditional ROI: 5.59%

1850 Candlelight Cir

MONTGOMERY, IL

3 beds | 2 baths | 1,754 sq.ft.

$309,900

Airbnb cash on cash: -1.62%

Traditional cash on cash: 4.31%

Airbnb Rental Income: $911

Traditional Rental Income: $2300

Airbnb ROI: -1.62%