Real Estate Investment Properties for Sale in Glenwood, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
440 E CLARK STREET GLENWOOD, IL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	3 beds \| 1 baths \| 1,258 sq.ft.	$261,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 4.64% Airbnb Rental Income: $1779 Traditional Rental Income: $1871 Airbnb ROI: 2.29% Traditional ROI: 4.64%
304 E Birch Drive GLENWOOD, IL Turnkey Investment Opportunity! Part of a single-family portfolio with an average 8 cap ra...	4 beds \| 2 baths \| 1,800 sq.ft.	$235,000	Airbnb cash on cash: -1.87% Traditional cash on cash: 7.55% Airbnb Rental Income: $705 Traditional Rental Income: $2491 Airbnb ROI: -1.87% Traditional ROI: 7.55%
520 N Roberts Drive #1C GLENWOOD, IL VERY NICE AND CLEAN FIRST FLOOR CONDO. NO STAIRS FOR YOU. 1 BEDROOM 1 BATHROOM. NEW CARPET...	1 beds \| 1 baths \| 800 sq.ft.	$89,999	Airbnb cash on cash: -5.68% Traditional cash on cash: 8.3% Airbnb Rental Income: $480 Traditional Rental Income: $1441 Airbnb ROI: -5.68% Traditional ROI: 8.3%
557 N CARROLL PKWY 1G GLENWOOD, IL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	2 beds \| 1 baths \| 1,000 sq.ft.	$109,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 9.17% Airbnb Rental Income: $1097 Traditional Rental Income: $1369 Airbnb ROI: 3.07% Traditional ROI: 9.17%
214 N Gay Court GLENWOOD, IL This beautifully updated home is ready for its new owners and is situated in the highly so...	3 beds \| 2 baths \| 1,088 sq.ft.	$292,700	Airbnb cash on cash: 0.66% Traditional cash on cash: 3.39% Airbnb Rental Income: $1779 Traditional Rental Income: $2047 Airbnb ROI: 0.66% Traditional ROI: 3.39%
250 E Maple Drive GLENWOOD, IL	4 beds \| 2 baths \| N/A	$195,000	Airbnb cash on cash: -2.14% Traditional cash on cash: 9.72% Airbnb Rental Income: $705 Traditional Rental Income: $2595 Airbnb ROI: -2.14% Traditional ROI: 9.72%
251 N Pleasant Drive GLENWOOD, IL Bring your qualified buyer, Seller can close quick! Price just reduced. Beautifully rehabb...	3 beds \| 2 baths \| 1,500 sq.ft.	$273,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 4.29% Airbnb Rental Income: $1779 Traditional Rental Income: $2298 Airbnb ROI: 0.39% Traditional ROI: 4.29%
40 N Sycamore Lane GLENWOOD, IL Turnkey Investment Opportunity! Part of a single-family portfolio with an average 8 cap ra...	2 beds \| 2 baths \| 763 sq.ft.	$229,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 5.31% Airbnb Rental Income: $1097 Traditional Rental Income: $1915 Airbnb ROI: -0.18% Traditional ROI: 5.31%
436 N PLEASANT Drive GLENWOOD, IL Welcome to this beautifully maintained ranch-style home offering 1,700 sq ft on the main f...	4 beds \| 2 baths \| 1,690 sq.ft.	$201,000	Airbnb cash on cash: -4.36% Traditional cash on cash: 5.75% Airbnb Rental Income: $705 Traditional Rental Income: $2327 Airbnb ROI: -4.36% Traditional ROI: 5.75%
424 E Clark Street GLENWOOD, IL Don't miss this bright and inviting split-level gem! Featuring cathedral ceilings that fil...	3 beds \| 2 baths \| 1,276 sq.ft.	$251,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 4.77% Airbnb Rental Income: $1779 Traditional Rental Income: $2183 Airbnb ROI: 1.02% Traditional ROI: 4.77%
900 W Strieff Lane GLENWOOD, IL Welcome to this 3-bedroom, 1.5-bathrooms split-level home in the Glenwood neighborhood. St...	3 beds \| 2 baths \| 1,269 sq.ft.	$216,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.85% Airbnb Rental Income: $1779 Traditional Rental Income: $2141 Airbnb ROI: 0.71% Traditional ROI: 4.85%
349 E Maple Drive GLENWOOD, IL Tucked against the wooded edge of a forest preserve, this raised ranch delivers a peaceful...	4 beds \| 2 baths \| 1,650 sq.ft.	$217,000	Airbnb cash on cash: -2.13% Traditional cash on cash: 7.84% Airbnb Rental Income: $705 Traditional Rental Income: $2448 Airbnb ROI: -2.13% Traditional ROI: 7.84%
330 W Holly Court GLENWOOD, IL Bright & Spacious 3-Bedroom Home in Glenwood - Step into this beautiful 3-bedroom, 1.5-bat...	3 beds \| 2 baths \| 1,269 sq.ft.	$227,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 4.4% Airbnb Rental Income: $1779 Traditional Rental Income: $2088 Airbnb ROI: 0.7% Traditional ROI: 4.4%
1122 W Iowa Street GLENWOOD, IL Nestled on a charming corner lot, this Glenwood home sits in a community with undeniable p...	4 beds \| 2 baths \| 2,176 sq.ft.	$292,000	Airbnb cash on cash: -3.93% Traditional cash on cash: 4.6% Airbnb Rental Income: $705 Traditional Rental Income: $2746 Airbnb ROI: -3.93% Traditional ROI: 4.6%
330 N Illinois Avenue GLENWOOD, IL Buyers could not secure financing! Now is your chance. Welcome to this beautifully maintai...	3 beds \| 2 baths \| 1,309 sq.ft.	$241,500	Airbnb cash on cash: 0.46% Traditional cash on cash: 4.29% Airbnb Rental Income: $1779 Traditional Rental Income: $2168 Airbnb ROI: 0.46% Traditional ROI: 4.29%
51 N Pine Lane GLENWOOD, IL Classic split-level offering 4 bedrooms, 2 bathrooms, and a den. Main level features a sun...	4 beds \| 2 baths \| 1,800 sq.ft.	$222,000	Airbnb cash on cash: -2.05% Traditional cash on cash: 7.63% Airbnb Rental Income: $705 Traditional Rental Income: $2433 Airbnb ROI: -2.05% Traditional ROI: 7.63%
340 N Illinois Avenue GLENWOOD, IL Welcome to this inviting 3 bed, 2 bath split-level home in Glenwood. Step inside to a larg...	3 beds \| 2 baths \| 1,963 sq.ft.	$294,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 3.84% Airbnb Rental Income: $1779 Traditional Rental Income: $2546 Airbnb ROI: -0.68% Traditional ROI: 3.84%
313 N Park Drive GLENWOOD, IL Move right in and enjoy this freshly updated 4-bedroom, 2-bathroom split-level home. Step ...	4 beds \| 2 baths \| 1,064 sq.ft.	$232,000	Airbnb cash on cash: -3.56% Traditional cash on cash: 4.34% Airbnb Rental Income: $705 Traditional Rental Income: $2131 Airbnb ROI: -3.56% Traditional ROI: 4.34%
40 N Elm Lane GLENWOOD, IL Welcome home to this stately and spacious split-level residence, perfectly situated on a q...	5 beds \| 3 baths \| 1,700 sq.ft.	$255,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.38% Airbnb Rental Income: $null Traditional Rental Income: $2716 Airbnb ROI: N/A Traditional ROI: 7.38%
231 E Tulip Drive GLENWOOD, IL This well-maintained 3-bedroom, 2-bath split-level home offers 1,375 square feet of functi...	3 beds \| 2 baths \| 1,375 sq.ft.	$221,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 7.06% Airbnb Rental Income: $1779 Traditional Rental Income: $2267 Airbnb ROI: 2.41% Traditional ROI: 7.06%
528 E 191st Place GLENWOOD, IL Absolutely beautiful, fully renovated, over-sized, brick split level with over 2,200 squar...	4 beds \| 3 baths \| 2,200 sq.ft.	$359,900	Airbnb cash on cash: -2.56% Traditional cash on cash: 4.97% Airbnb Rental Income: $705 Traditional Rental Income: $2943 Airbnb ROI: -2.56% Traditional ROI: 4.97%
1028 W Strieff Lane GLENWOOD, IL Brick home in a prime Glenwood location within the Homewood-Flossmoor School District. Thi...	4 beds \| 3 baths \| 1,776 sq.ft.	$250,000	Airbnb cash on cash: -3.96% Traditional cash on cash: 6.05% Airbnb Rental Income: $705 Traditional Rental Income: $2764 Airbnb ROI: -3.96% Traditional ROI: 6.05%
900 W Sunset Drive #505 GLENWOOD, IL Good size 2 bedroom ,large living room with dining area ,2 bath looking for a buyer that s...	2 beds \| 2 baths \| 1,100 sq.ft.	$114,000	Airbnb cash on cash: -2.51% Traditional cash on cash: 8.43% Airbnb Rental Income: $1097 Traditional Rental Income: $1930 Airbnb ROI: -2.51% Traditional ROI: 8.43%
225 S Willow Street GLENWOOD, IL We have adjusted our price so take another look! This is a MUST SEE!!! Nice open concep...	3 beds \| 2 baths \| 1,500 sq.ft.	$249,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 5.55% Airbnb Rental Income: $1779 Traditional Rental Income: $2270 Airbnb ROI: 1.41% Traditional ROI: 5.55%

Real Estate investment in Glenwood, IL

There are 31 properties for sale in the city of Glenwood . The median list price in Glenwood is $222,000 and the average price per square foot is $149. In December 2025, the average monthly cash on cash return in Glenwood is 6.00%. The average monthly rental income in Glenwood is $2,298.

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

There are 31 investment properties available for sale in Glenwood.

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

The ROI for Long-Term is higher than the Short-Term in Glenwood with average rental income of $2,298.

Your search for investment property begins and ends here

Investment Property for Sale in Glenwood, IL

440 E CLARK STREET

GLENWOOD, IL

3 beds | 1 baths | 1,258 sq.ft.

$261,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $1779

Traditional Rental Income: $1871

Airbnb ROI: 2.29%

Traditional ROI: 4.64%

304 E Birch Drive

GLENWOOD, IL

4 beds | 2 baths | 1,800 sq.ft.

$235,000

Airbnb cash on cash: -1.87%

Traditional cash on cash: 7.55%

Airbnb Rental Income: $705

Traditional Rental Income: $2491

Airbnb ROI: -1.87%

Traditional ROI: 7.55%

520 N Roberts Drive #1C

GLENWOOD, IL

1 beds | 1 baths | 800 sq.ft.

$89,999

Airbnb cash on cash: -5.68%

Traditional cash on cash: 8.3%

Airbnb Rental Income: $480

Traditional Rental Income: $1441

Airbnb ROI: -5.68%

Traditional ROI: 8.3%

557 N CARROLL PKWY 1G

GLENWOOD, IL

2 beds | 1 baths | 1,000 sq.ft.

$109,000

Airbnb cash on cash: 3.07%

Traditional cash on cash: 9.17%

Airbnb Rental Income: $1097

Traditional Rental Income: $1369

Airbnb ROI: 3.07%

Traditional ROI: 9.17%

214 N Gay Court

GLENWOOD, IL

3 beds | 2 baths | 1,088 sq.ft.

$292,700

Airbnb cash on cash: 0.66%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $1779

Traditional Rental Income: $2047

Airbnb ROI: 0.66%

Traditional ROI: 3.39%

250 E Maple Drive

GLENWOOD, IL

4 beds | 2 baths | N/A

$195,000

Airbnb cash on cash: -2.14%

Traditional cash on cash: 9.72%

Airbnb Rental Income: $705

Traditional Rental Income: $2595

Airbnb ROI: -2.14%

Traditional ROI: 9.72%

251 N Pleasant Drive

GLENWOOD, IL

3 beds | 2 baths | 1,500 sq.ft.

$273,000

Airbnb cash on cash: 0.39%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $1779

Traditional Rental Income: $2298

Airbnb ROI: 0.39%

Traditional ROI: 4.29%

40 N Sycamore Lane

GLENWOOD, IL

2 beds | 2 baths | 763 sq.ft.

$229,000

Airbnb cash on cash: -0.18%

Traditional cash on cash: 5.31%

Airbnb Rental Income: $1097

Traditional Rental Income: $1915

Airbnb ROI: -0.18%