Real Estate Investment Properties for Sale in Chesterland, OH

Looking for investment property in Chesterland, OH with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
10640 Butternut Rd Chesterland, OH Architecturally striking, 4 bedroom, 3.5 bath, multi-level home sits on over 9 acres of pr...	4 beds \| 3 baths \| 2,324 sq.ft.	$679,900	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.44% Airbnb Rental Income: $2298 Traditional Rental Income: $3889 Airbnb ROI: 0.03% Traditional ROI: 3.44%
7981 Mulberry Rd Chesterland, OH Beautifully updated 4 bedroom, 2.5 bathroom colonial situated on 3.05 picturesque acres. T...	4 beds \| 2 baths \| 2,300 sq.ft.	$529,900	Airbnb cash on cash: 1.12% Traditional cash on cash: 4.13% Airbnb Rental Income: $2298 Traditional Rental Income: $3216 Airbnb ROI: 1.12% Traditional ROI: 4.13%
7775 Woodlands Trl Chesterland, OH Nestled on three wooded acres on a quiet street, this extraordinary estate combines refine...	5 beds \| 4 baths \| 5,158 sq.ft.	$995,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 3.32% Airbnb Rental Income: $2637 Traditional Rental Income: $5200 Airbnb ROI: -0.13% Traditional ROI: 3.32%
12791 Morning Glory Trl Chesterland, OH 12791 Morning Glory Trl, Chesterland, OH 44026 \| Single Family Residential	4 beds \| 2 baths \| 0 sq.ft.	$425,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 4.05% Airbnb Rental Income: $2298 Traditional Rental Income: $2720 Airbnb ROI: 1.55% Traditional ROI: 4.05%
7885 Pear Tree Dr Chesterland, OH Set amidst over 5 acres of breathtaking, manicured grounds, this exceptional estate offers...	5 beds \| 4 baths \| 3,244 sq.ft.	$1,295,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 2.86% Airbnb Rental Income: $2637 Traditional Rental Income: $5516 Airbnb ROI: -0.06% Traditional ROI: 2.86%
9087 Ranch Dr Chesterland, OH Full general home inspection, septic and well inspections, along with a third-party apprai...	3 beds \| 1 baths \| 2,504 sq.ft.	$250,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 5.03% Airbnb Rental Income: $2257 Traditional Rental Income: $1818 Airbnb ROI: 4.5% Traditional ROI: 5.03%
13099 Dorothy Dr Chesterland, OH Welcome to 13099 Dorothy Drive, a beautifully maintained 4-bedroom, 2.5-bath ranch nestled...	4 beds \| 2 baths \| 1,638 sq.ft.	$299,900	Airbnb cash on cash: 3.68% Traditional cash on cash: 7.19% Airbnb Rental Income: $2298 Traditional Rental Income: $2718 Airbnb ROI: 3.68% Traditional ROI: 7.19%
11535 Blackberry Lane Chesterland, OH Set on 5 sprawling acres, this beautifully remodeled home offers the perfect blend of priv...	4 beds \| 3 baths \| 3,022 sq.ft.	$635,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 3.13% Airbnb Rental Income: $2298 Traditional Rental Income: $3327 Airbnb ROI: 0.43% Traditional ROI: 3.13%
12145 Reserve Ln Chesterland, OH 12145 Reserve Ln, Chesterland, OH 44026 \| Single Family Residential	4 beds \| 3 baths \| 3,350 sq.ft.	$750,000	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.54% Airbnb Rental Income: $2298 Traditional Rental Income: $2952 Airbnb ROI: -0.21% Traditional ROI: 1.54%
12513 Chillicothe Rd Chesterland, OH 12513 Chillicothe Rd, Chesterland, OH 44026 \| Other	N/A beds \| N/A baths \| N/A	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.84% Airbnb Rental Income: $null Traditional Rental Income: $887 Airbnb ROI: N/A Traditional ROI: -1.84%
13419 Sperry Rd Chesterland, OH 13419 Sperry Rd, Chesterland, OH 44026 \| Single Family Residential	3 beds \| 2 baths \| 2,132 sq.ft.	$379,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 3.66% Airbnb Rental Income: $2257 Traditional Rental Income: $2299 Airbnb ROI: 1.95% Traditional ROI: 3.66%
8264 Cedar Rd Chesterland, OH 8264 Cedar Rd, Chesterland, OH 44026 \| Single Family Residential	3 beds \| 1 baths \| 1,360 sq.ft.	$305,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.1% Airbnb Rental Income: $2257 Traditional Rental Income: $1714 Airbnb ROI: 3.03% Traditional ROI: 3.1%
8525 Kirkwood Dr Chesterland, OH 8525 Kirkwood Dr, Chesterland, OH 44026 \| Single Family Residential	3 beds \| 1 baths \| 2,129 sq.ft.	$325,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 4.92% Airbnb Rental Income: $2257 Traditional Rental Income: $2375 Airbnb ROI: 2.69% Traditional ROI: 4.92%
13037 Stratford Trl Chesterland, OH 13037 Stratford Trl, Chesterland, OH 44026 \| Single Family Residential	4 beds \| 2 baths \| 1,645 sq.ft.	$334,900	Airbnb cash on cash: 2.65% Traditional cash on cash: 4.32% Airbnb Rental Income: $2298 Traditional Rental Income: $2253 Airbnb ROI: 2.65% Traditional ROI: 4.32%
9284 Mayfield Rd Chesterland, OH 9284 Mayfield Rd, Chesterland, OH 44026 \| Single Family Residential	5 beds \| 3 baths \| 2,704 sq.ft.	$400,000	Airbnb cash on cash: 2.56% Traditional cash on cash: N/A Airbnb Rental Income: $2637 Traditional Rental Income: $0 Airbnb ROI: 2.56% Traditional ROI: N/A
12157 Sperry Rd Chesterland, OH 12157 Sperry Rd, Chesterland, OH 44026 \| Single Family Residential	5 beds \| 4 baths \| 5,754 sq.ft.	$2,750,000	Airbnb cash on cash: -1.8% Traditional cash on cash: -1.15% Airbnb Rental Income: $2637 Traditional Rental Income: $3675 Airbnb ROI: -1.8% Traditional ROI: -1.15%
10435 Cedar Rd Chesterland, OH 10435 Cedar Rd, Chesterland, OH 44026 \| Single Family Residential	3 beds \| 2 baths \| 1,386 sq.ft.	$340,000	Airbnb cash on cash: 2.46% Traditional cash on cash: 3.44% Airbnb Rental Income: $2257 Traditional Rental Income: $2005 Airbnb ROI: 2.46% Traditional ROI: 3.44%
7415 Avon Ln Chesterland, OH 7415 Avon Ln, Chesterland, OH 44026 \| Single Family Residential	3 beds \| 1 baths \| 1,512 sq.ft.	$299,900	Airbnb cash on cash: 3.12% Traditional cash on cash: 3.27% Airbnb Rental Income: $2257 Traditional Rental Income: $1734 Airbnb ROI: 3.12% Traditional ROI: 3.27%
11710 Sherwood Trail Chesterland, OH Tucked away on a quiet, picturesque cul-de-sac and set back along a stunning tree-lined dr...	4 beds \| 4 baths \| N/A	$674,900	Airbnb cash on cash: -0.1% Traditional cash on cash: 3.31% Airbnb Rental Income: $2298 Traditional Rental Income: $3875 Airbnb ROI: -0.1% Traditional ROI: 3.31%
10506 Mayfield Road Chesterland, OH Welcome to a truly one-of-a-kind custom log home nestled in the natural beauty of Chesterl...	3 beds \| 3 baths \| 3,228 sq.ft.	$625,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.25% Airbnb Rental Income: $2257 Traditional Rental Income: $2702 Airbnb ROI: 0.52% Traditional ROI: 2.25%

Real Estate investment in Chesterland, OH

There are 22 properties for sale in the city of Chesterland . The median list price in Chesterland is $406,757 and the average price per square foot is $180. In September 2026, the average monthly cash on cash return in Chesterland is 4.00%. The average monthly rental income in Chesterland is $2,718.

Chesterland, OH Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 22 investment properties available for sale in Chesterland.

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

The ROI for Long-Term is higher than the Short-Term in Chesterland with average rental income of $2,718.

Your search for investment property begins and ends here

Investment Property for Sale in Chesterland, OH

10640 Butternut Rd

Chesterland, OH

4 beds | 3 baths | 2,324 sq.ft.

$679,900

Airbnb cash on cash: 0.03%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $2298

Traditional Rental Income: $3889

Airbnb ROI: 0.03%

Traditional ROI: 3.44%

7981 Mulberry Rd

Chesterland, OH

4 beds | 2 baths | 2,300 sq.ft.

$529,900

Airbnb cash on cash: 1.12%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $2298

Traditional Rental Income: $3216

Airbnb ROI: 1.12%

Traditional ROI: 4.13%

7775 Woodlands Trl

Chesterland, OH

5 beds | 4 baths | 5,158 sq.ft.

$995,000

Airbnb cash on cash: -0.13%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $2637

Traditional Rental Income: $5200

Airbnb ROI: -0.13%

Traditional ROI: 3.32%

12791 Morning Glory Trl

Chesterland, OH

4 beds | 2 baths | 0 sq.ft.

$425,000

Airbnb cash on cash: 1.55%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $2298

Traditional Rental Income: $2720

Airbnb ROI: 1.55%

Traditional ROI: 4.05%

7885 Pear Tree Dr

Chesterland, OH

5 beds | 4 baths | 3,244 sq.ft.

$1,295,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $2637

Traditional Rental Income: $5516

Airbnb ROI: -0.06%

Traditional ROI: 2.86%

9087 Ranch Dr

Chesterland, OH

3 beds | 1 baths | 2,504 sq.ft.

$250,000

Airbnb cash on cash: 4.5%

Traditional cash on cash: 5.03%

Airbnb Rental Income: $2257

Traditional Rental Income: $1818

Airbnb ROI: 4.5%

Traditional ROI: 5.03%

13099 Dorothy Dr

Chesterland, OH

4 beds | 2 baths | 1,638 sq.ft.

$299,900

Airbnb cash on cash: 3.68%

Traditional cash on cash: 7.19%

Airbnb Rental Income: $2298

Traditional Rental Income: $2718

Airbnb ROI: 3.68%

Traditional ROI: 7.19%

11535 Blackberry Lane

Chesterland, OH

4 beds | 3 baths | 3,022 sq.ft.

$635,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $2298

Traditional Rental Income: $3327

Airbnb ROI: 0.43%