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.

Townhouses for Sale in Chester, MD

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
Other Investment Properties for Sale in Chester
54 QUEEN CAROLINE COURT CHESTER , MD Price Improvement...End Unit in Sought-After Queens Landing A Waterfront Lifestyle Awaits!...	2 beds \| 3 baths \| 1,280 sq.ft.	$415,000	Airbnb cash on cash: 7.85% Traditional cash on cash: 4.52% Airbnb Rental Income: $4662 Traditional Rental Income: $2400 Airbnb ROI: 7.85% Traditional ROI: 4.52%
444 MACUM CREEK DR CHESTER , MD Welcome to 444 Macum Creek DriveEnjoy the Water Views from the Main Level Porch, Upper...	3 beds \| 3 baths \| N/A	$850,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 1.68% Airbnb Rental Income: $6279 Traditional Rental Income: $2751 Airbnb ROI: 4.58% Traditional ROI: 1.68%
34 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%
49 QUEEN GUINEVERE WAY CHESTER , MD Welcome to Queens Landing, where resort-style living meets the comfort of home. This beaut...	2 beds \| 3 baths \| 1,600 sq.ft.	$529,250	Airbnb cash on cash: 5.71% Traditional cash on cash: 4.44% Airbnb Rental Income: $4662 Traditional Rental Income: $3064 Airbnb ROI: 5.71% Traditional ROI: 4.44%
203 BARREN RIDGE ROAD CHESTER , MD Priced to Sell- VERY motivated sellers!!! Nestled in the tranquil community of Chester, Ma...	3 beds \| 2 baths \| 2,072 sq.ft.	$475,000	Airbnb cash on cash: 9.36% Traditional cash on cash: 3.97% Airbnb Rental Income: $6279 Traditional Rental Income: $2647 Airbnb ROI: 9.36% Traditional ROI: 3.97%
1401 CALVERT ROAD CHESTER , MD Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - All on one le...	2 beds \| 2 baths \| 1,444 sq.ft.	$485,000	Airbnb cash on cash: 6.29% Traditional cash on cash: 3.29% Airbnb Rental Income: $4662 Traditional Rental Income: $2336 Airbnb ROI: 6.29% Traditional ROI: 3.29%
208 RINGNECK CT CHESTER , MD 208 Ringneck Court is a great home for the smart buyer! The 2 bedroom, 2 1/2 bathroom G...	2 beds \| 3 baths \| N/A	$339,900	Airbnb cash on cash: 9.08% Traditional cash on cash: 6.02% Airbnb Rental Income: $4662 Traditional Rental Income: $2721 Airbnb ROI: 9.08% Traditional ROI: 6.02%
170 HARRIER WAY #34 CHESTER , MD Open House this Sunday 8/24 from 12-2. New improved price of $795,000 and immediate occupa...	3 beds \| 3 baths \| N/A	$795,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 2.23% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.02% Traditional ROI: 2.23%
170 HARRIER WAY #11 CHESTER , MD *Redfin powered by Rocket Mortgage Preferred Pricing* Enjoy with a 1% lower interest r...	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 #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 #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* The Donegal model is a s...	2 beds \| 2 baths \| 1,900 sq.ft.	$639,500	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%
47 QUEEN ANNE WAY CHESTER , MD Enjoy resort style living every day in the gorgeous waterfront condo. 42' boat slip w/ wat...	2 beds \| 3 baths \| 1,440 sq.ft.	$598,000	Airbnb cash on cash: 4.93% Traditional cash on cash: 2% Airbnb Rental Income: $4662 Traditional Rental Income: $2059 Airbnb ROI: 4.93% Traditional ROI: 2%
15 QUEEN ANNE WAY #E CHESTER , MD The BIGGEST price drop yet!! Wake up to shimmering Chester River views and let every day f...	2 beds \| 3 baths \| 1,680 sq.ft.	$499,000	Airbnb cash on cash: 6.07% Traditional cash on cash: 4.57% Airbnb Rental Income: $4662 Traditional Rental Income: $2997 Airbnb ROI: 6.07% Traditional ROI: 4.57%

Your search for investment property begins and ends here

Townhouses for Sale in Chester, MD

312 BLENNY LANE

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%

Other Investment Properties for Sale in Chester

CHESTER , MD

2 beds | 3 baths | 1,280 sq.ft.

$415,000

Airbnb cash on cash: 7.85%

Traditional cash on cash: 4.52%

Airbnb Rental Income: $4662

Traditional Rental Income: $2400

Airbnb ROI: 7.85%

Traditional ROI: 4.52%

CHESTER , MD

3 beds | 3 baths | N/A

$850,000

Airbnb cash on cash: 4.58%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $6279

Traditional Rental Income: $2751

Airbnb ROI: 4.58%

Traditional ROI: 1.68%

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 | 3 baths | 1,600 sq.ft.

$529,250

Airbnb cash on cash: 5.71%

Traditional cash on cash: 4.44%

Airbnb Rental Income: $4662

Traditional Rental Income: $3064

Airbnb ROI: 5.71%

Traditional ROI: 4.44%

CHESTER , MD

3 beds | 2 baths | 2,072 sq.ft.

$475,000

Airbnb cash on cash: 9.36%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $6279

Traditional Rental Income: $2647

Airbnb ROI: 9.36%

Traditional ROI: 3.97%

CHESTER , MD

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

$485,000

Airbnb cash on cash: 6.29%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $4662

Traditional Rental Income: $2336

Airbnb ROI: 6.29%

Traditional ROI: 3.29%

CHESTER , MD

2 beds | 3 baths | N/A

$339,900

Airbnb cash on cash: 9.08%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $4662

Traditional Rental Income: $2721

Airbnb ROI: 9.08%

Traditional ROI: 6.02%

CHESTER , MD

3 beds | 3 baths | N/A

$795,000

Airbnb cash on cash: 5.02%

Traditional cash on cash: 2.23%