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.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.27% Airbnb Rental Income: $null Traditional Rental Income: $3889 Airbnb ROI: N/A Traditional ROI: 3.27%
12931 Westchester Trl Gates Mills, OH This flexible 4-5 bedroom Chesterland colonial is designed to grow and shift with you. it'...	5 beds \| 5 baths \| 2,974 sq.ft.	$535,000	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $2636 Airbnb ROI: N/A Traditional ROI: 3%
8585 Carmichael Dr Chesterland, OH Meticulously Maintained Four-Level Split with Custom Addition on a One-Acre Lot! Updated 3...	3 beds \| 2 baths \| 3,018 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $2578 Airbnb ROI: N/A Traditional ROI: 3.83%
10331 Butternut Road Chesterland, OH Nestled on nearly 3 private acres in Munson Township, this beautifully renovated home comb...	5 beds \| 5 baths \| 5,560 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.66% Airbnb Rental Income: $null Traditional Rental Income: $5309 Airbnb ROI: N/A Traditional ROI: 6.66%
11661 Sherwood Trl Gates Mills, OH LOCATION LOCATION LOCATION! Welcome to your charming, rustic retreat in sought after Chest...	4 beds \| 3 baths \| 3,371 sq.ft.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $3280 Airbnb ROI: N/A Traditional ROI: 3.03%
9471 Sherman Road Chesterland, OH Exquisite log home on 5 serene acres nestled in the heart of Chesterland, OH. This stunnin...	4 beds \| 2 baths \| 3,015 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.81% Airbnb Rental Income: $null Traditional Rental Income: $2779 Airbnb ROI: N/A Traditional ROI: 2.81%
12910 Westchester Trail Chesterland, OH This ranch has beautiful views with large windows and an open floor design for entertainin...	3 beds \| 3 baths \| N/A	$274,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.3% Airbnb Rental Income: $null Traditional Rental Income: $2595 Airbnb ROI: N/A Traditional ROI: 7.3%
12865 Rockhaven Road Chesterland, OH Tucked away on 2.42 private, wooded acres, this charming retreat blends natural beauty wit...	3 beds \| 2 baths \| 2,028 sq.ft.	$439,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $2472 Airbnb ROI: N/A Traditional ROI: 3.83%
9502 Winchester Valley Chesterland, OH Rare find with full first floor in-law or teen suite with large bedroom, full bath, full a...	5 beds \| 3 baths \| 3,326 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $3385 Airbnb ROI: N/A Traditional ROI: 4.64%
10263 Wye Road Chesterland, OH Have you been searching for a Ranch home that is ready to move in? We have one for you now...	3 beds \| 2 baths \| 1,436 sq.ft.	$339,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $2181 Airbnb ROI: N/A Traditional ROI: 4.78%
9613 Kim Drive Chesterland, OH Beautifully renovated 3 bedroom, 1.5 bath Ranch offering just over 1,500 sq ft. of stylish...	3 beds \| 2 baths \| 1,528 sq.ft.	$330,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.47% Airbnb Rental Income: $null Traditional Rental Income: $2351 Airbnb ROI: N/A Traditional ROI: 5.47%
11915 Oak Wood Lane Chesterland, OH Welcome to this beautifully maintained and updated 4 bedroom, 2.5 bath colonial, offering ...	4 beds \| 3 baths \| 3,516 sq.ft.	$539,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.08% Airbnb Rental Income: $null Traditional Rental Income: $3156 Airbnb ROI: N/A Traditional ROI: 4.08%

Real Estate investment in Chesterland, OH

There are 13 properties for sale in the city of Chesterland . The median list price in Chesterland is $500,000 and the average price per square foot is $174. In January 2026, the average monthly cash on cash return in Chesterland is 4.00%. The average monthly rental income in Chesterland is $2,708.

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

There are 13 investment properties available for sale in Chesterland.

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

The ROI for Short-Term is higher than the Long-Term in Chesterland with average rental income of $N/A.

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.

$699,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.27%

Airbnb Rental Income: $null

Traditional Rental Income: $3889

Airbnb ROI: N/A

Traditional ROI: 3.27%

12931 Westchester Trl

Gates Mills, OH

5 beds | 5 baths | 2,974 sq.ft.

$535,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3%

Airbnb Rental Income: $null

Traditional Rental Income: $2636

Airbnb ROI: N/A

Traditional ROI: 3%

8585 Carmichael Dr

Chesterland, OH

3 beds | 2 baths | 3,018 sq.ft.

$450,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.83%

Airbnb Rental Income: $null

Traditional Rental Income: $2578

Airbnb ROI: N/A

Traditional ROI: 3.83%

10331 Butternut Road

Chesterland, OH

5 beds | 5 baths | 5,560 sq.ft.

$650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.66%

Airbnb Rental Income: $null

Traditional Rental Income: $5309

Airbnb ROI: N/A

Traditional ROI: 6.66%

11661 Sherwood Trl

Gates Mills, OH

4 beds | 3 baths | 3,371 sq.ft.

$675,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.03%

Airbnb Rental Income: $null

Traditional Rental Income: $3280

Airbnb ROI: N/A

Traditional ROI: 3.03%

9471 Sherman Road

Chesterland, OH

4 beds | 2 baths | 3,015 sq.ft.

$595,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.81%

Airbnb Rental Income: $null

Traditional Rental Income: $2779

Airbnb ROI: N/A

Traditional ROI: 2.81%

12910 Westchester Trail

Chesterland, OH

3 beds | 3 baths | N/A

$274,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.3%

Airbnb Rental Income: $null

Traditional Rental Income: $2595

Airbnb ROI: N/A

Traditional ROI: 7.3%

12865 Rockhaven Road

Chesterland, OH

3 beds | 2 baths | 2,028 sq.ft.

$439,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.83%

Airbnb Rental Income: $null

Traditional Rental Income: $2472

Airbnb ROI: N/A