Real Estate Investment Properties for Sale in Darien, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
321 Janet Avenue DARIEN, IL Completely remodeled cozy starter home, 3-bed, 2-baths Cape Cod on a large corner lot. Ope...	3 beds \| 2 baths \| 1,372 sq.ft.	$395,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 3.63% Airbnb Rental Income: $2680 Traditional Rental Income: $2421 Airbnb ROI: 2.61% Traditional ROI: 3.63%
1052 Hinswood Drive DARIEN, IL Welcome to this beautifully updated, open-concept 2-story townhome offering modern eleganc...	2 beds \| 3 baths \| 1,273 sq.ft.	$348,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 1.45% Airbnb Rental Income: $1835 Traditional Rental Income: $1598 Airbnb ROI: 0.67% Traditional ROI: 1.45%
8581 Sandalwood Drive DARIEN, IL Welcome to this fabulous end unit ranch town home in Water Tower Courts, home to elegant, ...	2 beds \| 2 baths \| 1,400 sq.ft.	$400,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 1.51% Airbnb Rental Income: $1835 Traditional Rental Income: $2108 Airbnb ROI: -0.54% Traditional ROI: 1.51%
2605 Oxford Court DARIEN, IL Welcome to this stunning custom-renovated townhome, perfectly nestled in a beautiful cul-d...	3 beds \| 4 baths \| 2,263 sq.ft.	$550,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 2.67% Airbnb Rental Income: $2680 Traditional Rental Income: $2991 Airbnb ROI: 0.83% Traditional ROI: 2.67%
6722 Sweetbriar Lane DARIEN, IL Financing fell through!!! A quiet and friendly neighborhood convenient to shopping, highwa...	4 beds \| 5 baths \| 5,566 sq.ft.	$997,500	Airbnb cash on cash: 0.51% Traditional cash on cash: 2.6% Airbnb Rental Income: $3775 Traditional Rental Income: $4893 Airbnb ROI: 0.51% Traditional ROI: 2.6%
2004 Oldfield Road DARIEN, IL TO BE BUILT...Offering a Rare and Special New Build Opportunity in Darien's Gleneagles sub...	4 beds \| 4 baths \| 3,200 sq.ft.	$989,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 3.01% Airbnb Rental Income: $3775 Traditional Rental Income: $3927 Airbnb ROI: 1.96% Traditional ROI: 3.01%
7706 WARWICK Avenue DARIEN, IL Highest and Best called for due to multiple offers. Due date by 6/26 by noon. Amazing new ...	3 beds \| 2 baths \| 1,682 sq.ft.	$346,750	Airbnb cash on cash: 3.33% Traditional cash on cash: 4.82% Airbnb Rental Income: $2680 Traditional Rental Income: $2528 Airbnb ROI: 3.33% Traditional ROI: 4.82%
2713 Whitlock Drive DARIEN, IL Welcome to this beautifully maintained 3 bedroom, 2.5 bath townhome in the desirable Woodm...	3 beds \| 3 baths \| 1,704 sq.ft.	$399,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 2.93% Airbnb Rental Income: $2680 Traditional Rental Income: $2445 Airbnb ROI: 1.86% Traditional ROI: 2.93%
7113 Clarendon Hills Road DARIEN, IL Welcome home to this fully updated beautiful gem on a 0.3+ acre lot! Offering 4 bedrooms a...	4 beds \| 3 baths \| 2,024 sq.ft.	$509,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 3.7% Airbnb Rental Income: $3775 Traditional Rental Income: $2847 Airbnb ROI: 3.93% Traditional ROI: 3.7%
1120 Ponderosa Court DARIEN, IL Located in the sought after Woodlands community, this beautiful, home offers serene and na...	2 beds \| 2 baths \| 1,860 sq.ft.	$399,900	Airbnb cash on cash: -0.21% Traditional cash on cash: 2.79% Airbnb Rental Income: $1835 Traditional Rental Income: $2462 Airbnb ROI: -0.21% Traditional ROI: 2.79%
709 79TH Street #404 DARIEN, IL Rare opportunity to own a spacious 3-bedroom, 2-bath condo in a desirable Darien location ...	3 beds \| 2 baths \| 1,358 sq.ft.	$290,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 3.66% Airbnb Rental Income: $2680 Traditional Rental Income: $2288 Airbnb ROI: 2.76% Traditional ROI: 3.66%
2845 Water Tower Lane DARIEN, IL Welcome home to this beautifully maintained and move-in-ready 2-bedroom, 2.5-bath townhome...	2 beds \| 3 baths \| 1,600 sq.ft.	$400,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 2.88% Airbnb Rental Income: $1835 Traditional Rental Income: $2429 Airbnb ROI: -0.02% Traditional ROI: 2.88%
7730 BROOKHAVEN Avenue DARIEN, IL This Ranch Home must be seen to fully appreciate its beauty! It is located on a quiet stre...	3 beds \| 3 baths \| 2,106 sq.ft.	$599,900	Airbnb cash on cash: 1.53% Traditional cash on cash: 3.34% Airbnb Rental Income: $2680 Traditional Rental Income: $3058 Airbnb ROI: 1.53% Traditional ROI: 3.34%
7932 Stewart Drive DARIEN, IL Live and Enjoy Bailey's Park at such an affordable price ... Conveniently located to expre...	3 beds \| 3 baths \| 1,356 sq.ft.	$355,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 3.04% Airbnb Rental Income: $2680 Traditional Rental Income: $2352 Airbnb ROI: 2.12% Traditional ROI: 3.04%
7810 Del Court DARIEN, IL	4 beds \| 3 baths \| 2,554 sq.ft.	$625,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 2.61% Airbnb Rental Income: $3775 Traditional Rental Income: $3155 Airbnb ROI: 2.27% Traditional ROI: 2.61%
8044 Wildwood Lane DARIEN, IL Popular Sawmill Creek Townhome - Featuring Cathedral Ceilings in Living Rm / Dining Rm, Va...	2 beds \| 3 baths \| 1,352 sq.ft.	$389,900	Airbnb cash on cash: -0.05% Traditional cash on cash: 2.33% Airbnb Rental Income: $1835 Traditional Rental Income: $2214 Airbnb ROI: -0.05% Traditional ROI: 2.33%
7926 Stewart Drive DARIEN, IL Impeccably maintained original owner end unit townhome in highly sought after Bailey Park....	3 beds \| 3 baths \| 1,356 sq.ft.	$410,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 1.3% Airbnb Rental Income: $2680 Traditional Rental Income: $1870 Airbnb ROI: 1.75% Traditional ROI: 1.3%
7706 Hayenga Lane DARIEN, IL Welcome to 7706 Hayenga Lane in Darien! This beautifully maintained split-level home offer...	3 beds \| 2 baths \| 1,300 sq.ft.	$465,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 2.1% Airbnb Rental Income: $2680 Traditional Rental Income: $1851 Airbnb ROI: 2.54% Traditional ROI: 2.1%
18W088 Claremont Drive DARIEN, IL Move in ready Darien split level on large lot in a picturesque quiet neighborhood! First f...	3 beds \| 2 baths \| 1,950 sq.ft.	$499,999	Airbnb cash on cash: 1.53% Traditional cash on cash: 1.72% Airbnb Rental Income: $2680 Traditional Rental Income: $2132 Airbnb ROI: 1.53% Traditional ROI: 1.72%
8334 Portsmouth Drive #B DARIEN, IL Welcome home to this well-maintained 2-bedroom, 1-bath residence in the sought-after Ports...	2 beds \| 1 baths \| 956 sq.ft.	$249,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 1.52% Airbnb Rental Income: $1835 Traditional Rental Income: $1359 Airbnb ROI: 1.44% Traditional ROI: 1.52%
7806 Regency Grove Drive DARIEN, IL It's finally here! The home you've been waiting for, featuring one of the most spectacular...	4 beds \| 3 baths \| 2,452 sq.ft.	$775,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 2.1% Airbnb Rental Income: $3775 Traditional Rental Income: $3057 Airbnb ROI: 1.96% Traditional ROI: 2.1%
3252 87TH Street DARIEN, IL Welcome to this beautifully maintained tri-level home, offering an exceptional amount of l...	3 beds \| 2 baths \| 2,176 sq.ft.	$550,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 2.66% Airbnb Rental Income: $2680 Traditional Rental Income: $2632 Airbnb ROI: 1.52% Traditional ROI: 2.66%

Real Estate investment in Darien, IL

There are 44 properties for sale in the city of Darien . The median list price in Darien is $449,268 and the average price per square foot is $125. In June 2026, the average monthly cash on cash return in Darien is 3.00%. The average monthly rental income in Darien is $2,462.

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

There are 44 investment properties available for sale in Darien.

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

The ROI for Long-Term is higher than the Short-Term in Darien with average rental income of $2,462.

Your search for investment property begins and ends here

Investment Property for Sale in Darien, IL

321 Janet Avenue

DARIEN, IL

3 beds | 2 baths | 1,372 sq.ft.

$395,000

Airbnb cash on cash: 2.61%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $2680

Traditional Rental Income: $2421

Airbnb ROI: 2.61%

Traditional ROI: 3.63%

1052 Hinswood Drive

DARIEN, IL

2 beds | 3 baths | 1,273 sq.ft.

$348,000

Airbnb cash on cash: 0.67%

Traditional cash on cash: 1.45%

Airbnb Rental Income: $1835

Traditional Rental Income: $1598

Airbnb ROI: 0.67%

Traditional ROI: 1.45%

8581 Sandalwood Drive

DARIEN, IL

2 beds | 2 baths | 1,400 sq.ft.

$400,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $1835

Traditional Rental Income: $2108

Airbnb ROI: -0.54%

Traditional ROI: 1.51%

2605 Oxford Court

DARIEN, IL

3 beds | 4 baths | 2,263 sq.ft.

$550,000

Airbnb cash on cash: 0.83%

Traditional cash on cash: 2.67%

Airbnb Rental Income: $2680

Traditional Rental Income: $2991

Airbnb ROI: 0.83%

Traditional ROI: 2.67%

6722 Sweetbriar Lane

DARIEN, IL

4 beds | 5 baths | 5,566 sq.ft.

$997,500

Airbnb cash on cash: 0.51%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $3775

Traditional Rental Income: $4893

Airbnb ROI: 0.51%

Traditional ROI: 2.6%

2004 Oldfield Road

DARIEN, IL

4 beds | 4 baths | 3,200 sq.ft.

$989,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $3775

Traditional Rental Income: $3927

Airbnb ROI: 1.96%

Traditional ROI: 3.01%

7706 WARWICK Avenue

DARIEN, IL

3 beds | 2 baths | 1,682 sq.ft.

$346,750

Airbnb cash on cash: 3.33%

Traditional cash on cash: 4.82%

Airbnb Rental Income: $2680

Traditional Rental Income: $2528

Airbnb ROI: 3.33%

Traditional ROI: 4.82%

2713 Whitlock Drive

DARIEN, IL

3 beds | 3 baths | 1,704 sq.ft.

$399,000

Airbnb cash on cash: 1.86%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $2680

Traditional Rental Income: $2445

Airbnb ROI: 1.86%