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 3 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%
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.	$459,900	Airbnb cash on cash: 9.95% Traditional cash on cash: 3.8% Airbnb Rental Income: $6279 Traditional Rental Income: $2393 Airbnb ROI: 9.95% Traditional ROI: 3.8%
1704 BAYSIDE Drive CHESTER, MD Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautif...	3 beds \| 3 baths \| 1,830 sq.ft.	$1,100,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 1.5% Airbnb Rental Income: $6279 Traditional Rental Income: $3259 Airbnb ROI: 3.25% Traditional ROI: 1.5%
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%
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 Just reduced by $30,000 to $710,000 with immediate availability. This is one of only two ...	3 beds \| 3 baths \| N/A	$710,000	Airbnb cash on cash: 5.73% Traditional cash on cash: 2.61% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.73% Traditional ROI: 2.61%
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! Lowest pr...	2 beds \| 2 baths \| 1,900 sq.ft.	$639,450	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%
3000 HERONS NEST Way unit: 11 #11 CHESTER , MD Love Where You Live! Experience resort-style living that blends comfort, luxury, and conve...	2 beds \| 3 baths \| 2,003 sq.ft.	$555,900	Airbnb cash on cash: 5.2% Traditional cash on cash: 4% Airbnb Rental Income: $4662 Traditional Rental Income: $3069 Airbnb ROI: 5.2% Traditional ROI: 4%
202 MCHENNY Court CHESTER , MD Beautiful Home in Gibson's Grant with Elevator, Open Floor Plan & Two-Car Garage Welcome t...	3 beds \| 3 baths \| 2,520 sq.ft.	$825,000	Airbnb cash on cash: 4.74% Traditional cash on cash: 2.23% Airbnb Rental Income: $6279 Traditional Rental Income: $3114 Airbnb ROI: 4.74% Traditional ROI: 2.23%
162 KIRWANS LANDING Lane CHESTER , MD BIG PRICE IMPROVEMENT. Private Waterfront Living in Kirwans Landing!Nestled on 1.4 acres i...	4 beds \| 3 baths \| 2,404 sq.ft.	$869,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 3.1% Airbnb Rental Income: $5802 Traditional Rental Income: $3870 Airbnb ROI: 4.06% Traditional ROI: 3.1%
HARBOR Drive CHESTER , MD New home being built! Act now and pick all your colors! Finished models can be seen! Call ...	3 beds \| 2 baths \| 1,250 sq.ft.	$499,900	Airbnb cash on cash: 9.29% Traditional cash on cash: 3.96% Airbnb Rental Income: $6279 Traditional Rental Income: $2554 Airbnb ROI: 9.29% Traditional ROI: 3.96%
112 CHESSIE Court CHESTER , MD Step inside and see this meticulously cared for home! This home features a first floor pri...	3 beds \| 3 baths \| 2,066 sq.ft.	$519,900	Airbnb cash on cash: 8.45% Traditional cash on cash: 4.29% Airbnb Rental Income: $6279 Traditional Rental Income: $3022 Airbnb ROI: 8.45% Traditional ROI: 4.29%
1916 STEVENS Drive CHESTER , MD Discover this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a ...	3 beds \| 2 baths \| 1,728 sq.ft.	$495,000	Airbnb cash on cash: 9.06% Traditional cash on cash: 4.39% Airbnb Rental Income: $6279 Traditional Rental Income: $2880 Airbnb ROI: 9.06% Traditional ROI: 4.39%

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%

1340 QUEEN ANNE Drive

CHESTER, MD

3 beds | 2 baths | 1,248 sq.ft.

$459,900

Airbnb cash on cash: 9.95%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $6279

Traditional Rental Income: $2393

Airbnb ROI: 9.95%

Traditional ROI: 3.8%

1704 BAYSIDE Drive

CHESTER, MD

3 beds | 3 baths | 1,830 sq.ft.

$1,100,000

Airbnb cash on cash: 3.25%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $6279

Traditional Rental Income: $3259

Airbnb ROI: 3.25%

Traditional ROI: 1.5%

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

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

$710,000

Airbnb cash on cash: 5.73%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $6279

Traditional Rental Income: $2981

Airbnb ROI: 5.73%

Traditional ROI: 2.61%

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