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.

Towhnhouse for Sale in Chester, MD

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

Showing 26 Towhnhouse 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

Towhnhouse 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%