Real Estate Investment Properties for Sale in Chester, MD

Looking for investment property in Chester, MD with high ROI ?

Explore a variety of short-term homes & houses in Chester, MD. Invest wisely with VRBO & Chester, MD Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Chester, MD

Search for Single Family Residential for Sale in Chester, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 1 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
203 RIVERSIDE DR CHESTER, MD To-be-built 5BR, 3.5BA waterfront home by Laine Street Homes - now under construction and ...	5 beds \| 4 baths \| N/A	$1,099,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.28% Airbnb Rental Income: $null Traditional Rental Income: $1588 Airbnb ROI: N/A Traditional ROI: 0.28%
Other Investment Properties for Sale in Chester
34-E QUEEN ANNE Way CHESTER , MD Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water...	2 beds \| 3 baths \| 1,104 sq.ft.	$469,000	Airbnb cash on cash: 6% Traditional cash on cash: 4.56% Airbnb Rental Income: $4662 Traditional Rental Income: $3067 Airbnb ROI: 6% Traditional ROI: 4.56%
312 BLENNY Lane CHESTER , MD You do not want to miss this opportunity to enjoy island living in this maintenance free, ...	3 beds \| 4 baths \| 1,899 sq.ft.	$479,000	Airbnb cash on cash: 9.44% Traditional cash on cash: 4.77% Airbnb Rental Income: $6279 Traditional Rental Income: $2950 Airbnb ROI: 9.44% Traditional ROI: 4.77%
1401 CALVERT Road CHESTER , MD Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - PRICE REDUCED...	2 beds \| 2 baths \| 1,444 sq.ft.	$454,900	Airbnb cash on cash: 6.77% Traditional cash on cash: 3.57% Airbnb Rental Income: $4662 Traditional Rental Income: $2336 Airbnb ROI: 6.77% Traditional ROI: 3.57%
141 SWITCHGRASS Way unit: 34 #34 CHESTER , MD ** NICE VIEWS OF THE CHESTER RIVER * LOWEST PRICED SEVERN MODEL** K Hovnanian'...	3 beds \| 3 baths \| 2,600 sq.ft.	$684,950	Airbnb cash on cash: 5.57% Traditional cash on cash: 2.44% Airbnb Rental Income: $6279 Traditional Rental Income: $3044 Airbnb ROI: 5.57% Traditional ROI: 2.44%
170 HARRIER WAY #34 CHESTER , MD Recently reduced by $55,000 to $740,000 with immediate availability. This is one of only t...	3 beds \| 3 baths \| N/A	$740,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 2.47% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.46% Traditional ROI: 2.47%
170 HARRIER Way unit: 11 #11 CHESTER , MD Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bed...	2 beds \| 3 baths \| 2,003 sq.ft.	$499,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.02% Airbnb Rental Income: $4662 Traditional Rental Income: $3099 Airbnb ROI: 5.3% Traditional ROI: 4.02%
190 HARRIER Way unit: 11 #11 CHESTER , MD Luxury 55+ Living at Four Seasons on Kent Island - Move-In Ready & Priced to Sell! Welcome...	2 beds \| 3 baths \| 2,003 sq.ft.	$540,000	Airbnb cash on cash: 4.83% Traditional cash on cash: 2.17% Airbnb Rental Income: $4662 Traditional Rental Income: $2354 Airbnb ROI: 4.83% Traditional ROI: 2.17%
1000 HERONS NEST Way unit: 32 #32 CHESTER , MD Move in this May and enjoy low-maintenance living in the sought-after 55+ community of Fou...	2 beds \| 2 baths \| N/A	$499,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 2.75% Airbnb Rental Income: $4662 Traditional Rental Income: $2521 Airbnb ROI: 5.26% Traditional ROI: 2.75%
154 HARRIER WAY CHESTER , MD * WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND* Price Reduced! Better th...	2 beds \| 2 baths \| 1,900 sq.ft.	$639,545	Airbnb cash on cash: 3.75% Traditional cash on cash: 1.13% Airbnb Rental Income: $4662 Traditional Rental Income: $2132 Airbnb ROI: 3.75% Traditional ROI: 1.13%
1340 QUEEN ANNE Drive CHESTER , MD Discover the charm of this fully updated ranch in a serene, water-privileged community! Wi...	3 beds \| 2 baths \| 1,248 sq.ft.	$464,900	Airbnb cash on cash: 9.84% Traditional cash on cash: 3.75% Airbnb Rental Income: $6279 Traditional Rental Income: $2393 Airbnb ROI: 9.84% Traditional ROI: 3.75%
114 ADDISON Court CHESTER , MD REDUCED "Shiny and new" might be the best way to describe the feel of this lovely 3 be...	3 beds \| 3 baths \| 2,342 sq.ft.	$549,900	Airbnb cash on cash: 7.82% Traditional cash on cash: 4.06% Airbnb Rental Income: $6279 Traditional Rental Income: $3111 Airbnb ROI: 7.82% Traditional ROI: 4.06%
132 CLAIBORNE Street CHESTER , MD Discover exceptional living on an oversized fenced lot in the sought-after community of Gi...	3 beds \| 4 baths \| 2,400 sq.ft.	$659,000	Airbnb cash on cash: 5.66% Traditional cash on cash: 2.63% Airbnb Rental Income: $6279 Traditional Rental Income: $3180 Airbnb ROI: 5.66% Traditional ROI: 2.63%
1000 HERONS NEST Way unit: 22 #22 CHESTER , MD Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum C...	2 beds \| 3 baths \| 1,900 sq.ft.	$488,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.47% Airbnb Rental Income: $4662 Traditional Rental Income: $3249 Airbnb ROI: 5.44% Traditional ROI: 4.47%
30-C QUEEN MARY Court CHESTER , MD OPEN HOUSE SUN 12/7 11a-1p! Settlement possible for the Holidays & New Year! Enjoy low-mai...	2 beds \| 3 baths \| 1,440 sq.ft.	$339,900	Airbnb cash on cash: 9.59% Traditional cash on cash: 5.9% Airbnb Rental Income: $4662 Traditional Rental Income: $2518 Airbnb ROI: 9.59% Traditional ROI: 5.9%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chester, MD

203 RIVERSIDE DR

CHESTER, MD

5 beds | 4 baths | N/A

$1,099,900

Airbnb cash on cash: N/A

Traditional cash on cash: 0.28%

Airbnb Rental Income: $null

Traditional Rental Income: $1588

Airbnb ROI: N/A

Traditional ROI: 0.28%

Other Investment Properties for Sale in Chester

CHESTER , MD

2 beds | 3 baths | 1,104 sq.ft.

$469,000

Airbnb cash on cash: 6%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $4662

Traditional Rental Income: $3067

Airbnb ROI: 6%

Traditional ROI: 4.56%

CHESTER , MD

3 beds | 4 baths | 1,899 sq.ft.

$479,000

Airbnb cash on cash: 9.44%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $6279

Traditional Rental Income: $2950

Airbnb ROI: 9.44%

Traditional ROI: 4.77%

CHESTER , MD

2 beds | 2 baths | 1,444 sq.ft.

$454,900

Airbnb cash on cash: 6.77%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $4662

Traditional Rental Income: $2336

Airbnb ROI: 6.77%

Traditional ROI: 3.57%

CHESTER , MD

3 beds | 3 baths | 2,600 sq.ft.

$684,950

Airbnb cash on cash: 5.57%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $6279

Traditional Rental Income: $3044

Airbnb ROI: 5.57%

Traditional ROI: 2.44%

CHESTER , MD

3 beds | 3 baths | N/A

$740,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $6279

Traditional Rental Income: $2981

Airbnb ROI: 5.46%

Traditional ROI: 2.47%

CHESTER , MD

2 beds | 3 baths | 2,003 sq.ft.

$499,000

Airbnb cash on cash: 5.3%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $4662

Traditional Rental Income: $3099

Airbnb ROI: 5.3%

Traditional ROI: 4.02%

CHESTER , MD

2 beds | 3 baths | 2,003 sq.ft.

$540,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $4662

Traditional Rental Income: $2354

Airbnb ROI: 4.83%

Traditional ROI: 2.17%

CHESTER , MD

2 beds | 2 baths | N/A

$499,000

Airbnb cash on cash: 5.26%

Traditional cash on cash: 2.75%