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: 3.75% Traditional cash on cash: 4.64% Airbnb Rental Income: $2211 Traditional Rental Income: $1871 Airbnb ROI: 3.75% 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: N/A Traditional cash on cash: 7.55% Airbnb Rental Income: $null Traditional Rental Income: $2491 Airbnb ROI: N/A Traditional ROI: 7.55%
815 W 187th Street GLENWOOD, IL Make this Glenwood ranch your own! Located in the highly regarded Homewood Flossmoor schoo...	3 beds \| 2 baths \| 1,080 sq.ft.	$199,900	Airbnb cash on cash: 3.16% Traditional cash on cash: 4.95% Airbnb Rental Income: $2211 Traditional Rental Income: $1993 Airbnb ROI: 3.16% Traditional ROI: 4.95%
110 N Oak Lane GLENWOOD, IL Turnkey Investment Opportunity! Part of a single-family portfolio with an average 8 cap ra...	3 beds \| 1 baths \| 950 sq.ft.	$195,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 4.71% Airbnb Rental Income: $2211 Traditional Rental Income: $1681 Airbnb ROI: 4.56% Traditional ROI: 4.71%
123 N Glenwood Avenue GLENWOOD, IL Solid three bedroom home with one bathroom freshly painted and beautiful hardwood floors,...	2 beds \| 1 baths \| 900 sq.ft.	$190,000	Airbnb cash on cash: -1.74% Traditional cash on cash: 3.31% Airbnb Rental Income: $992 Traditional Rental Income: $1551 Airbnb ROI: -1.74% Traditional ROI: 3.31%
113 N Rebecca Street GLENWOOD, IL MAJOR UPDATES IN 2025: NEW ROOF, NEW WINDOWS, NEW HEATING, NEW CENTRAL A/C, AND NEW GARAGE...	3 beds \| 2 baths \| 964 sq.ft.	$202,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 5.67% Airbnb Rental Income: $2211 Traditional Rental Income: $2015 Airbnb ROI: 3.78% Traditional ROI: 5.67%
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: 2.24% Traditional cash on cash: 9.17% Airbnb Rental Income: $992 Traditional Rental Income: $1369 Airbnb ROI: 2.24% 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: 1.97% Traditional cash on cash: 3.39% Airbnb Rental Income: $2211 Traditional Rental Income: $2047 Airbnb ROI: 1.97% Traditional ROI: 3.39%
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.	$288,900	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.01% Airbnb Rental Income: $2211 Traditional Rental Income: $2298 Airbnb ROI: 1.64% Traditional ROI: 4.01%
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: -0.58% Traditional cash on cash: 5.31% Airbnb Rental Income: $992 Traditional Rental Income: $1915 Airbnb ROI: -0.58% Traditional ROI: 5.31%
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: -3.3% Traditional cash on cash: 8.43% Airbnb Rental Income: $992 Traditional Rental Income: $1930 Airbnb ROI: -3.3% Traditional ROI: 8.43%
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.	$205,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.62% Airbnb Rental Income: $null Traditional Rental Income: $2327 Airbnb ROI: N/A Traditional ROI: 5.62%
553 N Carroll Parkway #1-D GLENWOOD, IL Welcome to 553 N. Carroll Parkway, Unit 1-D in Glenwood, IL - a beautifully maintained, in...	2 beds \| 1 baths \| 800 sq.ft.	$115,000	Airbnb cash on cash: -1.86% Traditional cash on cash: 6.53% Airbnb Rental Income: $992 Traditional Rental Income: $1570 Airbnb ROI: -1.86% Traditional ROI: 6.53%
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.	$256,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 4.66% Airbnb Rental Income: $2211 Traditional Rental Income: $2183 Airbnb ROI: 2.47% Traditional ROI: 4.66%
127 N Cedar Lane GLENWOOD, IL This well-maintained split-level home offers a spacious and flexible layout, featuring thr...	3 beds \| 3 baths \| 917 sq.ft.	$190,000	Airbnb cash on cash: 4.7% Traditional cash on cash: 8.93% Airbnb Rental Income: $2211 Traditional Rental Income: $2418 Airbnb ROI: 4.7% Traditional ROI: 8.93%
555 N Cherry Drive GLENWOOD, IL This 3-bed, 2-bath split-level offers a bright sunroom, patio, and spacious yard-perfect f...	3 beds \| 2 baths \| 1,378 sq.ft.	$200,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 5.87% Airbnb Rental Income: $2211 Traditional Rental Income: $2209 Airbnb ROI: 2.94% Traditional ROI: 5.87%
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.	$228,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 4.55% Airbnb Rental Income: $2211 Traditional Rental Income: $2141 Airbnb ROI: 2.29% Traditional ROI: 4.55%
702 W Fitzhenry Court GLENWOOD, IL ALL VILLAGE REQUIREMENTS COMPLETED. WE CAN CLOSE QUICKY PRICE JUST REDUCED. WOW! WHAT...	4 beds \| 3 baths \| 2,000 sq.ft.	$289,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.3% Airbnb Rental Income: $null Traditional Rental Income: $2941 Airbnb ROI: N/A Traditional ROI: 6.3%
417 S Glenwoodie Drive GLENWOOD, IL This Residence located on the 18th fairway of Glenwoodie Golf course with direct view of t...	2 beds \| 2 baths \| 2,193 sq.ft.	$429,900	Airbnb cash on cash: -2.51% Traditional cash on cash: 1.9% Airbnb Rental Income: $992 Traditional Rental Income: $2416 Airbnb ROI: -2.51% Traditional ROI: 1.9%
130 N Oak Lane GLENWOOD, IL Get ready to fall in love with this lively 4-bedroom, 2-bathroom home in the heart of Glen...	4 beds \| 2 baths \| 1,675 sq.ft.	$212,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.36% Airbnb Rental Income: $null Traditional Rental Income: $2466 Airbnb ROI: N/A Traditional ROI: 8.36%
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.	$228,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.43% Airbnb Rental Income: $null Traditional Rental Income: $2448 Airbnb ROI: N/A Traditional ROI: 7.43%
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.	$232,000	Airbnb cash on cash: 2.3% Traditional cash on cash: 4.28% Airbnb Rental Income: $2211 Traditional Rental Income: $2088 Airbnb ROI: 2.3% Traditional ROI: 4.28%
19119 S Saint Lawrence Avenue GLENWOOD, IL Fabulous oversized home in unincorporated Glenwood! This spacious 4-bedroom, 3-bath reside...	4 beds \| 3 baths \| 2,494 sq.ft.	$239,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.52% Airbnb Rental Income: $null Traditional Rental Income: $3294 Airbnb ROI: N/A Traditional ROI: 10.52%
242 S Harper Avenue GLENWOOD, IL Tucked away in the delightful community of Glenwood, Illinois, this beautifully reimagined...	3 beds \| 2 baths \| 1,476 sq.ft.	$332,700	Airbnb cash on cash: 1.49% Traditional cash on cash: 3.67% Airbnb Rental Income: $2211 Traditional Rental Income: $2334 Airbnb ROI: 1.49% Traditional ROI: 3.67%
404 E Maple Drive GLENWOOD, IL Nestled in the heart of Glenwood, this spacious raised ranch offers the perfect blend of s...	4 beds \| 2 baths \| 1,938 sq.ft.	$230,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.32% Airbnb Rental Income: $null Traditional Rental Income: $2527 Airbnb ROI: N/A Traditional ROI: 8.32%
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.	$310,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.28% Airbnb Rental Income: $null Traditional Rental Income: $2746 Airbnb ROI: N/A Traditional ROI: 4.28%
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.	$234,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.19% Airbnb Rental Income: $null Traditional Rental Income: $2433 Airbnb ROI: N/A Traditional ROI: 7.19%
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.	$312,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 3.57% Airbnb Rental Income: $2211 Traditional Rental Income: $2546 Airbnb ROI: 0.53% Traditional ROI: 3.57%
511 W Arquilla Drive GLENWOOD, IL This light, bright, and inviting 3 bedroom, 1.5 bath tri-level home is ready for you now! ...	3 beds \| 2 baths \| 2,100 sq.ft.	$269,999	Airbnb cash on cash: 2.53% Traditional cash on cash: 6.28% Airbnb Rental Income: $2211 Traditional Rental Income: $2608 Airbnb ROI: 2.53% Traditional ROI: 6.28%
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.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.96% Airbnb Rental Income: $null Traditional Rental Income: $2131 Airbnb ROI: N/A Traditional ROI: 3.96%
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: 2.94% Traditional cash on cash: 5.55% Airbnb Rental Income: $2211 Traditional Rental Income: $2270 Airbnb ROI: 2.94% Traditional ROI: 5.55%

Real Estate investment in Glenwood, IL

There are 40 properties for sale in the city of Glenwood . The median list price in Glenwood is $231,000 and the average price per square foot is $155. In October 2025, the average monthly cash on cash return in Glenwood is 6.00%. The average monthly rental income in Glenwood is $2,265.

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

There are 40 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 $2,265.

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: 3.75%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $2211

Traditional Rental Income: $1871

Airbnb ROI: 3.75%

Traditional ROI: 4.64%

304 E Birch Drive

GLENWOOD, IL

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

$235,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.55%

Airbnb Rental Income: $null

Traditional Rental Income: $2491

Airbnb ROI: N/A

Traditional ROI: 7.55%

815 W 187th Street

GLENWOOD, IL

3 beds | 2 baths | 1,080 sq.ft.

$199,900

Airbnb cash on cash: 3.16%

Traditional cash on cash: 4.95%

Airbnb Rental Income: $2211

Traditional Rental Income: $1993

Airbnb ROI: 3.16%

Traditional ROI: 4.95%

110 N Oak Lane

GLENWOOD, IL

3 beds | 1 baths | 950 sq.ft.

$195,000

Airbnb cash on cash: 4.56%

Traditional cash on cash: 4.71%

Airbnb Rental Income: $2211

Traditional Rental Income: $1681

Airbnb ROI: 4.56%

Traditional ROI: 4.71%

123 N Glenwood Avenue

GLENWOOD, IL

2 beds | 1 baths | 900 sq.ft.

$190,000

Airbnb cash on cash: -1.74%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $992

Traditional Rental Income: $1551

Airbnb ROI: -1.74%

Traditional ROI: 3.31%

113 N Rebecca Street

GLENWOOD, IL

3 beds | 2 baths | 964 sq.ft.

$202,000

Airbnb cash on cash: 3.78%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $2211

Traditional Rental Income: $2015

Airbnb ROI: 3.78%

Traditional ROI: 5.67%

557 N CARROLL PKWY 1G

GLENWOOD, IL

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

$109,000

Airbnb cash on cash: 2.24%

Traditional cash on cash: 9.17%

Airbnb Rental Income: $992

Traditional Rental Income: $1369

Airbnb ROI: 2.24%

Traditional ROI: 9.17%

214 N Gay Court

GLENWOOD, IL

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

$292,700

Airbnb cash on cash: 1.97%

Traditional cash on cash: 3.39%

Airbnb Rental Income: $2211

Traditional Rental Income: $2047

Airbnb ROI: 1.97%