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
350 E Tulip Dr GLENWOOD, IL SELLER WILL PAY 3% OF THE SALE PRICE TOWARDS THE BUYER'S CLOSINGS COSTS! You must see this...	3 beds \| 1 baths \| 1,750 sq.ft.	$154,900	Airbnb cash on cash: 4.37% Traditional cash on cash: 4.87% Airbnb Rental Income: $1779 Traditional Rental Income: $1368 Airbnb ROI: 4.37% Traditional ROI: 4.87%
415 W Holly Ct GLENWOOD, IL PRICED TO SELL! Homewood/Flossmoor High School District! Huge potential for growing famil...	3 beds \| 2 baths \| 1,088 sq.ft.	$220,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 3.32% Airbnb Rental Income: $1779 Traditional Rental Income: $1547 Airbnb ROI: 2.11% Traditional ROI: 3.32%
147 E Maple Dr GLENWOOD, IL Great investment opportunity, tenant occupied $1550 monthly income. Tenant on 1 year lease...	3 beds \| 2 baths \| 1,550 sq.ft.	$244,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 6.45% Airbnb Rental Income: $1779 Traditional Rental Income: $2204 Airbnb ROI: 2.51% Traditional ROI: 6.45%
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%
815 W 187th St GLENWOOD, IL Make this Glenwood ranch your own! Located in the highly regarded Homewood Flossmoor schoo...	3 beds \| 2 baths \| 1,080 sq.ft.	$191,900	Airbnb cash on cash: 1.35% Traditional cash on cash: 5.19% Airbnb Rental Income: $1779 Traditional Rental Income: $1993 Airbnb ROI: 1.35% Traditional ROI: 5.19%
123 N Glenwood Ave GLENWOOD, IL Solid 3 bedroom home with one bathroom newly painted and beautiful hardwood floors, New si...	3 beds \| 1 baths \| 900 sq.ft.	$174,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 3.7% Airbnb Rental Income: $1779 Traditional Rental Income: $1551 Airbnb ROI: 2.15% Traditional ROI: 3.7%
308 S Walnut St GLENWOOD, IL Invest with success and buy through Auction.com. This foreclosure investment property is a...	3 beds \| 1 baths \| 1,230 sq.ft.	$245,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 2.36% Airbnb Rental Income: $1779 Traditional Rental Income: $1388 Airbnb ROI: 1.95% Traditional ROI: 2.36%
520 N Roberts Dr #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 Ct GLENWOOD, IL This beautifully updated home is ready for its new owners and is situated in the highly so...	4 beds \| 2 baths \| 1,088 sq.ft.	$290,700	Airbnb cash on cash: -2.6% Traditional cash on cash: 3.42% Airbnb Rental Income: $705 Traditional Rental Income: $2047 Airbnb ROI: -2.6% Traditional ROI: 3.42%
251 N Pleasant Dr GLENWOOD, IL Bring your qualified buyer, Seller can close quick! Price just reduced. Beautifully rehabb...	3 beds \| 1 baths \| 1,500 sq.ft.	$272,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 4.31% Airbnb Rental Income: $1779 Traditional Rental Income: $2298 Airbnb ROI: 0.4% Traditional ROI: 4.31%
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.	$246,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.88% Airbnb Rental Income: $1779 Traditional Rental Income: $2183 Airbnb ROI: 1.05% Traditional ROI: 4.88%
821 W Manor Ct GLENWOOD, IL Don't judge a book by its cover-this original-owner home has been lovingly maintained and ...	4 beds \| 2 baths \| 1,950 sq.ft.	$347,900	Airbnb cash on cash: -2.47% Traditional cash on cash: 3.91% Airbnb Rental Income: $705 Traditional Rental Income: $2481 Airbnb ROI: -2.47% Traditional ROI: 3.91%
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.	$210,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 5.02% Airbnb Rental Income: $1779 Traditional Rental Income: $2141 Airbnb ROI: 0.76% Traditional ROI: 5.02%
330 W Holly Ct GLENWOOD, IL Bright & Spacious 3-Bedroom Home in Glenwood - Step into this beautiful 3-bedroom, 1.5-bat...	3 beds \| 1 baths \| 1,269 sq.ft.	$220,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 4.56% Airbnb Rental Income: $1779 Traditional Rental Income: $2088 Airbnb ROI: 0.75% Traditional ROI: 4.56%
242 S Harper Ave GLENWOOD, IL Just reduced! Make an offer! Tucked away in a delightful community, this beautifully reima...	3 beds \| 2 baths \| 1,476 sq.ft.	$309,700	Airbnb cash on cash: 0.44% Traditional cash on cash: 4.01% Airbnb Rental Income: $1779 Traditional Rental Income: $2334 Airbnb ROI: 0.44% Traditional ROI: 4.01%
1122 W Iowa St GLENWOOD, IL Nestled on a charming corner lot, this Glenwood home sits in a community with undeniable p...	4 beds \| 1 baths \| 2,176 sq.ft.	$275,000	Airbnb cash on cash: -4.11% Traditional cash on cash: 4.94% Airbnb Rental Income: $705 Traditional Rental Income: $2746 Airbnb ROI: -4.11% Traditional ROI: 4.94%
51 N Pine Ln 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.	$205,000	Airbnb cash on cash: -2.14% Traditional cash on cash: 8.32% Airbnb Rental Income: $705 Traditional Rental Income: $2433 Airbnb ROI: -2.14% Traditional ROI: 8.32%
340 N Illinois Ave 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.	$265,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 4.36% Airbnb Rental Income: $1779 Traditional Rental Income: $2546 Airbnb ROI: -0.65% Traditional ROI: 4.36%
511 W Arquilla Drive GLENWOOD, IL This light, bright, and inviting 3 bedroom, 1.5 bath tri-level home with BIG ADDITION is r...	3 beds \| 2 baths \| 2,100 sq.ft.	$255,999	Airbnb cash on cash: 1.23% Traditional cash on cash: 6.67% Airbnb Rental Income: $1779 Traditional Rental Income: $2608 Airbnb ROI: 1.23% Traditional ROI: 6.67%
313 N Park Dr 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.	$220,000	Airbnb cash on cash: -3.69% Traditional cash on cash: 4.62% Airbnb Rental Income: $705 Traditional Rental Income: $2131 Airbnb ROI: -3.69% Traditional ROI: 4.62%
40 N Elm Ln GLENWOOD, IL Welcome home to this stately and spacious split-level residence, perfectly situated on a q...	5 beds \| 2 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 Dr 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.	$210,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 7.47% Airbnb Rental Income: $1779 Traditional Rental Income: $2267 Airbnb ROI: 2.58% Traditional ROI: 7.47%
500 N Illinois Ave GLENWOOD, IL START THE NEW YEAR OFF IN A NEW HOME!! This 3 bed/2 bath split-level in Glenwood Estates i...	3 beds \| 2 baths \| 1,794 sq.ft.	$260,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 3.31% Airbnb Rental Income: $1779 Traditional Rental Income: $2423 Airbnb ROI: -1.3% Traditional ROI: 3.31%
528 E 191st Pl GLENWOOD, IL Absolutely beautiful, fully renovated, over-sized, brick split level with over 2,200 squar...	4 beds \| 2 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%
1033 W Ohio St GLENWOOD, IL Welcome to this beautifully maintained 3-bedroom, 2-bathroom home in the heart of Glenwood...	3 beds \| 2 baths \| 1,566 sq.ft.	$270,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 4.77% Airbnb Rental Income: $1779 Traditional Rental Income: $2307 Airbnb ROI: 0.79% Traditional ROI: 4.77%
629 N Carroll Pkwy #208 GLENWOOD, IL Open floor plan and designed for easy living, this beautifully maintained 2-bedroom, 1-bat...	2 beds \| 1 baths \| 1,000 sq.ft.	$110,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 7.65% Airbnb Rental Income: $1097 Traditional Rental Income: $1623 Airbnb ROI: -0.78% Traditional ROI: 7.65%
450 E Mulberry Ct GLENWOOD, IL Extra large floor plan, renewed & improved raised ranch w/oversize enclosed screen balcony...	4 beds \| 2 baths \| 2,360 sq.ft.	$245,000	Airbnb cash on cash: -2.46% Traditional cash on cash: 7.25% Airbnb Rental Income: $705 Traditional Rental Income: $2646 Airbnb ROI: -2.46% Traditional ROI: 7.25%
37 N Cedar Ln GLENWOOD, IL 37 N Cedar Ln, GLENWOOD, IL 60425 \| Single Family Residential	4 beds \| 1 baths \| 775 sq.ft.	$184,900	Airbnb cash on cash: -1.49% Traditional cash on cash: 3.85% Airbnb Rental Income: $705 Traditional Rental Income: $1338 Airbnb ROI: -1.49% Traditional ROI: 3.85%
240 N Park Dr GLENWOOD, IL	4 beds \| 2 baths \| 1,088 sq.ft.	$240,000	Airbnb cash on cash: -1.89% Traditional cash on cash: 3.16% Airbnb Rental Income: $705 Traditional Rental Income: $1544 Airbnb ROI: -1.89% Traditional ROI: 3.16%
931 W Arquilla Dr #133 GLENWOOD, IL 931 W Arquilla Dr #133, GLENWOOD, IL 60425 \| Condo/Coop	2 beds \| 2 baths \| 1,100 sq.ft.	$130,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 4% Airbnb Rental Income: $1097 Traditional Rental Income: $1390 Airbnb ROI: -1.32% Traditional ROI: 4%
830 E 191st Pl #709 GLENWOOD, IL 830 E 191st Pl #709, GLENWOOD, IL 60425 \| Condo/Coop	2 beds \| 1 baths \| 809 sq.ft.	$119,700	Airbnb cash on cash: -0.61% Traditional cash on cash: 3.67% Airbnb Rental Income: $1097 Traditional Rental Income: $1220 Airbnb ROI: -0.61% Traditional ROI: 3.67%
931 Arquilla Dr #314 GLENWOOD, IL 931 Arquilla Dr #314, GLENWOOD, IL 60425 \| Condo/Coop	2 beds \| 2 baths \| 900 sq.ft.	$160,000	Airbnb cash on cash: -1.53% Traditional cash on cash: 2.18% Airbnb Rental Income: $1097 Traditional Rental Income: $1291 Airbnb ROI: -1.53% Traditional ROI: 2.18%
326 S Minerva Ave GLENWOOD, IL 326 S Minerva Ave, GLENWOOD, IL 60425 \| Single Family Residential	4 beds \| 1 baths \| 1,971 sq.ft.	$180,000	Airbnb cash on cash: -1.44% Traditional cash on cash: 4.23% Airbnb Rental Income: $705 Traditional Rental Income: $1370 Airbnb ROI: -1.44% Traditional ROI: 4.23%
827 E 194th St #827 GLENWOOD, IL	2 beds \| 1 baths \| 1,100 sq.ft.	$135,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 3.49% Airbnb Rental Income: $1097 Traditional Rental Income: $1248 Airbnb ROI: -0.54% Traditional ROI: 3.49%
335 E Mulberry Dr GLENWOOD, IL 335 E Mulberry Dr, GLENWOOD, IL 60425 \| Single Family Residential	4 beds \| 2 baths \| 1,585 sq.ft.	$226,000	Airbnb cash on cash: -1.81% Traditional cash on cash: 4.93% Airbnb Rental Income: $705 Traditional Rental Income: $1839 Airbnb ROI: -1.81% Traditional ROI: 4.93%
700 N Bruce Ln #312 GLENWOOD, IL 700 N Bruce Ln #312, GLENWOOD, IL 60425 \| Condo/Coop	2 beds \| 2 baths \| 1,200 sq.ft.	$150,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 5.76% Airbnb Rental Income: $1097 Traditional Rental Income: $1809 Airbnb ROI: -1.79% Traditional ROI: 5.76%
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%
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.	$199,000	Airbnb cash on cash: -4.39% Traditional cash on cash: 5.82% Airbnb Rental Income: $705 Traditional Rental Income: $2327 Airbnb ROI: -4.39% Traditional ROI: 5.82%
900 W Sunset Drive unit: 405 #405 GLENWOOD, IL Step into the modernized, functional and spacious condo featuring updates throughout. The ...	2 beds \| 2 baths \| 1,000 sq.ft.	$160,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 8.21% Airbnb Rental Income: $1097 Traditional Rental Income: $1660 Airbnb ROI: 2.1% Traditional ROI: 8.21%

Real Estate investment in Glenwood, IL

There are 41 properties for sale in the city of Glenwood . The median list price in Glenwood is $220,000 and the average price per square foot is $155. In February 2026, the average monthly cash on cash return in Glenwood is 5.00%. The average monthly rental income in Glenwood is $2,088.

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

There are 41 investment properties available for sale in Glenwood.

In 2026, 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 $2,088.

Your search for investment property begins and ends here

Investment Property for Sale in Glenwood, IL

350 E Tulip Dr

GLENWOOD, IL

3 beds | 1 baths | 1,750 sq.ft.

$154,900

Airbnb cash on cash: 4.37%

Traditional cash on cash: 4.87%

Airbnb Rental Income: $1779

Traditional Rental Income: $1368

Airbnb ROI: 4.37%

Traditional ROI: 4.87%

415 W Holly Ct

GLENWOOD, IL

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

$220,000

Airbnb cash on cash: 2.11%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $1779

Traditional Rental Income: $1547

Airbnb ROI: 2.11%

Traditional ROI: 3.32%

147 E Maple Dr

GLENWOOD, IL

3 beds | 2 baths | 1,550 sq.ft.

$244,000

Airbnb cash on cash: 2.51%

Traditional cash on cash: 6.45%

Airbnb Rental Income: $1779

Traditional Rental Income: $2204

Airbnb ROI: 2.51%

Traditional ROI: 6.45%

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%

815 W 187th St

GLENWOOD, IL

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

$191,900

Airbnb cash on cash: 1.35%

Traditional cash on cash: 5.19%

Airbnb Rental Income: $1779

Traditional Rental Income: $1993

Airbnb ROI: 1.35%

Traditional ROI: 5.19%

123 N Glenwood Ave

GLENWOOD, IL

3 beds | 1 baths | 900 sq.ft.

$174,000

Airbnb cash on cash: 2.15%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $1779

Traditional Rental Income: $1551

Airbnb ROI: 2.15%

Traditional ROI: 3.7%

308 S Walnut St

GLENWOOD, IL

3 beds | 1 baths | 1,230 sq.ft.

$245,000

Airbnb cash on cash: 1.95%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $1779

Traditional Rental Income: $1388

Airbnb ROI: 1.95%

Traditional ROI: 2.36%

520 N Roberts Dr #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%