Real Estate Investment Properties for Sale in Cortland, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
347 N Aspen Drive CORTLAND, IL A new inventory home at Richland Trails, the popular Basswood II Ranch. This charming sing...	2 beds \| 2 baths \| 1,328 sq.ft.	$365,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 5.45% Airbnb Rental Income: $1112 Traditional Rental Income: $2421 Airbnb ROI: 0.53% Traditional ROI: 5.45%
300 N Aspen Drive CORTLAND, IL A new inventory home at Richland Trails, the popular Hickory IV Ranch. This charming singl...	3 beds \| 2 baths \| 1,613 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.25% Airbnb Rental Income: $null Traditional Rental Income: $2551 Airbnb ROI: N/A Traditional ROI: 5.25%
336 N Charles Street CORTLAND, IL AMAZING, WILLIAMSBURG MODEL RANCH HOME WITH BEAUTIFUL OPEN CONCEPT!!! Another spectacular ...	3 beds \| 2 baths \| 1,435 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.95% Airbnb Rental Income: $null Traditional Rental Income: $2439 Airbnb ROI: N/A Traditional ROI: 5.95%
324 N Blue Jay Street CORTLAND, IL BRAND NEW, CHARLOTTE MODEL RANCH HOME WITH BEAUTIFUL OPEN CONCEPT!!! Another spectacular p...	3 beds \| 2 baths \| 1,522 sq.ft.	$359,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.85% Airbnb Rental Income: $null Traditional Rental Income: $2468 Airbnb ROI: N/A Traditional ROI: 5.85%
348 N Blue Jay Street CORTLAND, IL BRAND NEW WESTCHESTER MODEL, WITH FANTASTIC OPEN FLOOR PLAN!! Another spectacular new cons...	4 beds \| 2 baths \| 1,640 sq.ft.	$374,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.6% Airbnb Rental Income: $null Traditional Rental Income: $2477 Airbnb ROI: N/A Traditional ROI: 5.6%
21 W Winterberry Avenue CORTLAND, IL *SYCAMORE SCHOOL DISTRICT!NO HOA DUES!NO SSA TAX!* Located in the Nature Crossin...	3 beds \| 2 baths \| 1,535 sq.ft.	$377,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $2437 Airbnb ROI: N/A Traditional ROI: 3.73%
511 S Preston Street CORTLAND, IL AMAZING, UNDER CONSTRUCTION 1/2 DUPLEX!! Another spectacular new construction project in t...	2 beds \| 1 baths \| 1,165 sq.ft.	$254,900	Airbnb cash on cash: -0.75% Traditional cash on cash: 5.33% Airbnb Rental Income: $1112 Traditional Rental Income: $2201 Airbnb ROI: -0.75% Traditional ROI: 5.33%
513 S Preston Street CORTLAND, IL AMAZING, UNDER CONSTRUCTION 1/2 DUPLEX!! Another spectacular new construction project in t...	2 beds \| 1 baths \| 1,165 sq.ft.	$254,900	Airbnb cash on cash: -0.75% Traditional cash on cash: 5.33% Airbnb Rental Income: $1112 Traditional Rental Income: $2201 Airbnb ROI: -0.75% Traditional ROI: 5.33%
523 S Preston Street CORTLAND, IL AMAZING, UNDER CONSTRUCTION 1/2 DUPLEX!! Another spectacular new construction project in t...	2 beds \| 1 baths \| 1,120 sq.ft.	$239,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 6.38% Airbnb Rental Income: $1112 Traditional Rental Income: $2319 Airbnb ROI: -0.6% Traditional ROI: 6.38%
529 S Preston Street CORTLAND, IL AMAZING, UNDER CONSTRUCTION 1/2 DUPLEX!! Another spectacular new construction project in t...	2 beds \| 1 baths \| 1,120 sq.ft.	$239,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 5.71% Airbnb Rental Income: $1112 Traditional Rental Income: $2167 Airbnb ROI: -0.6% Traditional ROI: 5.71%
34 W Meadow Drive CORTLAND, IL AMAZING, TWO-STORY HAMILTON MODEL WITH A BEAUTIFUL OPEN CONCEPT!!! Another spectacular pro...	4 beds \| 3 baths \| 2,330 sq.ft.	$414,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.37% Airbnb Rental Income: $null Traditional Rental Income: $3021 Airbnb ROI: N/A Traditional ROI: 6.37%
219 N Hickory Street CORTLAND, IL Rare park-backed privacy meets move-in-ready comfort in this beautifully maintained 3 bedr...	3 beds \| 2 baths \| 1,416 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $2300 Airbnb ROI: N/A Traditional ROI: 4.42%

Real Estate investment in Cortland, IL

There are 19 properties for sale in the city of Cortland . The median list price in Cortland is $324,900 and the average price per square foot is $212. In May 2026, the average monthly cash on cash return in Cortland is 6.00%. The average monthly rental income in Cortland is $2,439.

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

There are 19 investment properties available for sale in Cortland.

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

The ROI for Long-Term is higher than the Short-Term in Cortland with average rental income of $2,439.

Your search for investment property begins and ends here

Investment Property for Sale in Cortland, IL

347 N Aspen Drive

CORTLAND, IL

2 beds | 2 baths | 1,328 sq.ft.

$365,000

Airbnb cash on cash: 0.53%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $1112

Traditional Rental Income: $2421

Airbnb ROI: 0.53%

Traditional ROI: 5.45%

300 N Aspen Drive

CORTLAND, IL

3 beds | 2 baths | 1,613 sq.ft.

$399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.25%

Airbnb Rental Income: $null

Traditional Rental Income: $2551

Airbnb ROI: N/A

Traditional ROI: 5.25%

336 N Charles Street

CORTLAND, IL

3 beds | 2 baths | 1,435 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.95%

Airbnb Rental Income: $null

Traditional Rental Income: $2439

Airbnb ROI: N/A

Traditional ROI: 5.95%

324 N Blue Jay Street

CORTLAND, IL

3 beds | 2 baths | 1,522 sq.ft.

$359,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.85%

Airbnb Rental Income: $null

Traditional Rental Income: $2468

Airbnb ROI: N/A

Traditional ROI: 5.85%

348 N Blue Jay Street

CORTLAND, IL

4 beds | 2 baths | 1,640 sq.ft.

$374,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.6%

Airbnb Rental Income: $null

Traditional Rental Income: $2477

Airbnb ROI: N/A

Traditional ROI: 5.6%

21 W Winterberry Avenue

CORTLAND, IL

3 beds | 2 baths | 1,535 sq.ft.

$377,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2437

Airbnb ROI: N/A

Traditional ROI: 3.73%

511 S Preston Street

CORTLAND, IL

2 beds | 1 baths | 1,165 sq.ft.

$254,900

Airbnb cash on cash: -0.75%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $1112

Traditional Rental Income: $2201

Airbnb ROI: -0.75%

Traditional ROI: 5.33%

513 S Preston Street

CORTLAND, IL

2 beds | 1 baths | 1,165 sq.ft.

$254,900

Airbnb cash on cash: -0.75%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $1112

Traditional Rental Income: $2201

Airbnb ROI: -0.75%