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 Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Chester, MD

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

Showing 26 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory 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
34-E QUEEN ANNE Way CHESTER, MD Open House Saturday April 4th 12:15- 1:30. Fully Remodeled Chester River Waterfront Condo!...	2 beds \| 3 baths \| 1,586 sq.ft.	$549,000	Airbnb cash on cash: 4.48% Traditional cash on cash: 3.25% Airbnb Rental Income: $4662 Traditional Rental Income: $3067 Airbnb ROI: 4.48% Traditional ROI: 3.25%
402 BLENNY LN CHESTER, MD End-unit three-level townhome overlooking the pond in Bayside community. Freshly painted, ...	3 beds \| 4 baths \| N/A	$399,000	Airbnb cash on cash: 9.71% Traditional cash on cash: 5.93% Airbnb Rental Income: $6279 Traditional Rental Income: $3629 Airbnb ROI: 9.71% Traditional ROI: 5.93%
1000 HERONS NEST WAY unit: 23 CHESTER, MD Welcome to 1000 Herons Nest Way, where you can live the good life at an great price. This ...	2 beds \| 3 baths \| 2,003 sq.ft.	$494,900	Airbnb cash on cash: 3.32% Traditional cash on cash: 0.37% Airbnb Rental Income: $4662 Traditional Rental Income: $2331 Airbnb ROI: 3.32% Traditional ROI: 0.37%
1000 HERONS NEST Way unit: 32 #32 CHESTER, MD Step into the good life in the sought-after Four Seasons on Kent Island, where low-mainten...	2 beds \| 2 baths \| N/A	$499,000	Airbnb cash on cash: 3.51% Traditional cash on cash: 0.99% Airbnb Rental Income: $4662 Traditional Rental Income: $2521 Airbnb ROI: 3.51% Traditional ROI: 0.99%
4000 HERONS NEST Way unit: 22 CHESTER, MD ** New Listing! Four Seasons @ Kent Island - 55+ Community - Turnkey & Lovely 2nd Floor Co...	2 beds \| 3 baths \| 1,900 sq.ft.	$560,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 1.76% Airbnb Rental Income: $4662 Traditional Rental Income: $3075 Airbnb ROI: 2.95% Traditional ROI: 1.76%
1868 ROBERTA Drive CHESTER, MD This custom built home offers the perfect opportunity to live just minutes away from the C...	5 beds \| 4 baths \| 3,250 sq.ft.	$749,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.74% Airbnb Rental Income: $null Traditional Rental Income: $3937 Airbnb ROI: N/A Traditional ROI: 3.74%
111 MARSHGRASS WAY #22 CHESTER, MD Rare resale condo, turnkey! Your dream retreat awaits in this stunning luxury condo, where...	2 beds \| 3 baths \| N/A	$539,000	Airbnb cash on cash: 5.22% Traditional cash on cash: 3.36% Airbnb Rental Income: $4662 Traditional Rental Income: $2761 Airbnb ROI: 5.22% Traditional ROI: 3.36%
807 AUCKLAND Way CHESTER, MD Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier ...	3 beds \| 4 baths \| 2,100 sq.ft.	$425,000	Airbnb cash on cash: 8.67% Traditional cash on cash: 4.76% Airbnb Rental Income: $6279 Traditional Rental Income: $3486 Airbnb ROI: 8.67% Traditional ROI: 4.76%
1872 HARBOR Drive CHESTER, MD Harbor View Community \| Corner Lot \| Renovated Rancher with Room to Grow Welcome to 1872 H...	3 beds \| 2 baths \| 1,486 sq.ft.	$485,000	Airbnb cash on cash: 9.35% Traditional cash on cash: 4% Airbnb Rental Income: $6279 Traditional Rental Income: $2614 Airbnb ROI: 9.35% Traditional ROI: 4%
1916 STEVENS Drive CHESTER, MD Come see this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a ...	3 beds \| 2 baths \| 1,728 sq.ft.	$489,000	Airbnb cash on cash: 9.18% Traditional cash on cash: 4.45% Airbnb Rental Income: $6279 Traditional Rental Income: $2880 Airbnb ROI: 9.18% Traditional ROI: 4.45%
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: 3.24% Traditional cash on cash: 1.49% Airbnb Rental Income: $6279 Traditional Rental Income: $3259 Airbnb ROI: 3.24% Traditional ROI: 1.49%
54-H QUEEN CAROLINE CT CHESTER, MD Nothing to do but move in! This roomy 2 bedroom, 2.5 bathroom end unit has been completel...	2 beds \| 3 baths \| N/A	$349,000	Airbnb cash on cash: 7.53% Traditional cash on cash: 2.55% Airbnb Rental Income: $4662 Traditional Rental Income: $2064 Airbnb ROI: 7.53% Traditional ROI: 2.55%
6-G QUEEN VICTORIA Way CHESTER, MD Price Improvement!! Marina-front and perfectly sized for easy living or a weekend escape. ...	1 beds \| 1 baths \| 724 sq.ft.	$295,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 3.2% Airbnb Rental Income: $3572 Traditional Rental Income: $1681 Airbnb ROI: 7.19% Traditional ROI: 3.2%
3-D QUEEN VICTORIA Court CHESTER, MD Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living roo...	1 beds \| 1 baths \| 724 sq.ft.	$269,000	Airbnb cash on cash: 8.05% Traditional cash on cash: 3.02% Airbnb Rental Income: $3572 Traditional Rental Income: $1511 Airbnb ROI: 8.05% Traditional ROI: 3.02%
27 QUEEN MARY CT #F CHESTER, MD Fabulous Adriatic Grande unit ( largest end unit and 1 of 4) in the desirable Queens Landi...	2 beds \| 2 baths \| N/A	$419,000	Airbnb cash on cash: 6.07% Traditional cash on cash: 1.71% Airbnb Rental Income: $4662 Traditional Rental Income: $1984 Airbnb ROI: 6.07% Traditional ROI: 1.71%
1337 QUEEN ANNE DR CHESTER, MD Charming Renovated Ranch in Marling Farms This updated three-bedroom, two-and-a-half-bath ...	3 beds \| 3 baths \| N/A	$485,000	Airbnb cash on cash: 9.22% Traditional cash on cash: 4.45% Airbnb Rental Income: $6279 Traditional Rental Income: $2878 Airbnb ROI: 9.22% Traditional ROI: 4.45%
230 SWITCHGRASS WAY #21 CHESTER, MD --------------------------------------EXCEPTIONAL PANORAMIC VIEWS -----------------------...	3 beds \| 3 baths \| N/A	$694,500	Airbnb cash on cash: 5.84% Traditional cash on cash: 2.41% Airbnb Rental Income: $6279 Traditional Rental Income: $2820 Airbnb ROI: 5.84% Traditional ROI: 2.41%
8-F QUEEN VICTORIA WAY CHESTER, MD Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertai...	1 beds \| 1 baths \| N/A	$249,000	Airbnb cash on cash: 8.77% Traditional cash on cash: 2.48% Airbnb Rental Income: $3572 Traditional Rental Income: $1309 Airbnb ROI: 8.77% Traditional ROI: 2.48%
2000 HERONS NEST Way unit: 401 CHESTER, MD HERE IT IS! This Rare Luxurious Severn Penthouse, available immediately, offers a lifestyl...	3 beds \| 3 baths \| 2,602 sq.ft.	$750,000	Airbnb cash on cash: 3.71% Traditional cash on cash: 0.87% Airbnb Rental Income: $6279 Traditional Rental Income: $3059 Airbnb ROI: 3.71% Traditional ROI: 0.87%
266 PEREGRINE Drive CHESTER, MD Huge Price Reduction on this beautiful, less than 1 year old home in the sought after comm...	4 beds \| 3 baths \| 2,870 sq.ft.	$728,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 3.09% Airbnb Rental Income: $5802 Traditional Rental Income: $3367 Airbnb ROI: 4.97% Traditional ROI: 3.09%
249 WARBLER Way CHESTER, MD OPEN HOUSE SATURDAY 3/28/26! 10am to 12pm No waiting on the Builder here! This almost ...	2 beds \| 2 baths \| 2,025 sq.ft.	$699,000	Airbnb cash on cash: 3.72% Traditional cash on cash: 2% Airbnb Rental Income: $4662 Traditional Rental Income: $2576 Airbnb ROI: 3.72% Traditional ROI: 2%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Chester, MD

34-E QUEEN ANNE Way

CHESTER, MD

2 beds | 3 baths | 1,586 sq.ft.

$549,000

Airbnb cash on cash: 4.48%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $4662

Traditional Rental Income: $3067

Airbnb ROI: 4.48%

Traditional ROI: 3.25%

402 BLENNY LN

CHESTER, MD

3 beds | 4 baths | N/A

$399,000

Airbnb cash on cash: 9.71%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $6279

Traditional Rental Income: $3629

Airbnb ROI: 9.71%

Traditional ROI: 5.93%

1000 HERONS NEST WAY unit: 23

CHESTER, MD

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

$494,900

Airbnb cash on cash: 3.32%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $4662

Traditional Rental Income: $2331

Airbnb ROI: 3.32%

Traditional ROI: 0.37%

1000 HERONS NEST Way unit: 32 #32

CHESTER, MD

2 beds | 2 baths | N/A

$499,000

Airbnb cash on cash: 3.51%

Traditional cash on cash: 0.99%

Airbnb Rental Income: $4662

Traditional Rental Income: $2521

Airbnb ROI: 3.51%

Traditional ROI: 0.99%

4000 HERONS NEST Way unit: 22

CHESTER, MD

2 beds | 3 baths | 1,900 sq.ft.

$560,000

Airbnb cash on cash: 2.95%

Traditional cash on cash: 1.76%

Airbnb Rental Income: $4662

Traditional Rental Income: $3075

Airbnb ROI: 2.95%

Traditional ROI: 1.76%

1868 ROBERTA Drive

CHESTER, MD

5 beds | 4 baths | 3,250 sq.ft.

$749,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.74%

Airbnb Rental Income: $null

Traditional Rental Income: $3937

Airbnb ROI: N/A

Traditional ROI: 3.74%

111 MARSHGRASS WAY #22

CHESTER, MD

2 beds | 3 baths | N/A

$539,000

Airbnb cash on cash: 5.22%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $4662

Traditional Rental Income: $2761

Airbnb ROI: 5.22%

Traditional ROI: 3.36%

807 AUCKLAND Way

CHESTER, MD

3 beds | 4 baths | 2,100 sq.ft.

$425,000

Airbnb cash on cash: 8.67%

Traditional cash on cash: 4.76%

Airbnb Rental Income: $6279

Traditional Rental Income: $3486

Airbnb ROI: 8.67%