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.

Condos for Sale in Chester, MD

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

Showing 29 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
3000 Herons Nest Way #11 CHESTER, MD Love Where You Live! Experience resort-style living that blends comfort, luxury, and conve...	2 beds \| 2 baths \| 2,003 sq.ft.	$555,800	Airbnb cash on cash: 3.08% Traditional cash on cash: 1.06% Airbnb Rental Income: $4662 Traditional Rental Income: $2646 Airbnb ROI: 3.08% Traditional ROI: 1.06%
200 Harrier Way #21 CHESTER, MD The stunning Severn home design is loaded with designer options and includes 3 bedrooms, 2...	3 beds \| 2 baths \| 2,600 sq.ft.	$669,900	Airbnb cash on cash: 5.04% Traditional cash on cash: 1.58% Airbnb Rental Income: $6279 Traditional Rental Income: $2881 Airbnb ROI: 5.04% Traditional ROI: 1.58%
1000 Herons Nest Way #23 CHESTER, MD Welcome to 1000 Herons Nest Way, where you can live the good life at an great price. This ...	2 beds \| 2 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 #32 CHESTER, MD Step into the good life in the sought-after Four Seasons on Kent Island, where low-mainten...	2 beds \| 2 baths \| 1,900 sq.ft.	$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%
111 Marshgrass Way #22 CHESTER, MD Rare resale condo, turnkey and only one year young! Your dream retreat awaits in this stun...	2 beds \| 2 baths \| 1,900 sq.ft.	$539,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 1.75% Airbnb Rental Income: $4662 Traditional Rental Income: $2761 Airbnb ROI: 3.61% Traditional ROI: 1.75%
176 Flagstaff Way #33 CHESTER, MD 176 Flagstaff Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$829,990	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.08% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 2.58% Traditional ROI: 1.08%
176 Flagstaff Way #43 CHESTER, MD 176 Flagstaff Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$979,990	Airbnb cash on cash: 1.87% Traditional cash on cash: 0.6% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.87% Traditional ROI: 0.6%
176 Flagstaff Way #2443 CHESTER, MD 176 Flagstaff Way #2443, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$979,900	Airbnb cash on cash: 1.09% Traditional cash on cash: -0.18% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.09% Traditional ROI: -0.18%
176 Flagstaff Way #2433 CHESTER, MD 176 Flagstaff Way #2433, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$829,990	Airbnb cash on cash: 1.66% Traditional cash on cash: 0.16% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.66% Traditional ROI: 0.16%
176 Flagstaff Way #12 CHESTER, MD 176 Flagstaff Way #12, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$659,990	Airbnb cash on cash: 3.77% Traditional cash on cash: 1.97% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 3.77% Traditional ROI: 1.97%
176 Flagstaff Way #2412 CHESTER, MD 176 Flagstaff Way #2412, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$659,990	Airbnb cash on cash: 2.62% Traditional cash on cash: 0.82% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 2.62% Traditional ROI: 0.82%
Chester Plan CHESTER, MD	2 beds \| 2 baths \| 1,900 sq.ft.	$499,990	Airbnb cash on cash: 5.62% Traditional cash on cash: 1.8% Airbnb Rental Income: $4662 Traditional Rental Income: $1908 Airbnb ROI: 5.62% Traditional ROI: 1.8%
Magothy Plan CHESTER, MD	2 beds \| 2 baths \| 2,003 sq.ft.	$499,990	Airbnb cash on cash: 5.62% Traditional cash on cash: 1.85% Airbnb Rental Income: $4662 Traditional Rental Income: $1931 Airbnb ROI: 5.62% Traditional ROI: 1.85%
170 Harrier Way #22 CHESTER, MD 170 Harrier Way #22, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$499,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 1.48% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 3.96% Traditional ROI: 1.48%
Severn Plan CHESTER, MD	3 beds \| 2 baths \| 2,602 sq.ft.	$584,990	Airbnb cash on cash: 6.98% Traditional cash on cash: 1.69% Airbnb Rental Income: $6279 Traditional Rental Income: $2155 Airbnb ROI: 6.98% Traditional ROI: 1.69%
110 Boatswain Way #3021 CHESTER, MD 110 Boatswain Way #3021, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$789,990	Airbnb cash on cash: 3.68% Traditional cash on cash: 0.35% Airbnb Rental Income: $6279 Traditional Rental Income: $2592 Airbnb ROI: 3.68% Traditional ROI: 0.35%
110 Boatswain Way #3031 CHESTER, MD 110 Boatswain Way #3031, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$889,990	Airbnb cash on cash: 3.03% Traditional cash on cash: 0.07% Airbnb Rental Income: $6279 Traditional Rental Income: $2592 Airbnb ROI: 3.03% Traditional ROI: 0.07%
110 Boatswain Way #3032 CHESTER, MD 110 Boatswain Way #3032, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$759,990	Airbnb cash on cash: 2% Traditional cash on cash: 0.39% Airbnb Rental Income: $4662 Traditional Rental Income: $2555 Airbnb ROI: 2% Traditional ROI: 0.39%
110 Boatswain Way #3033 CHESTER, MD 110 Boatswain Way #3033, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$759,990	Airbnb cash on cash: 2% Traditional cash on cash: 0.39% Airbnb Rental Income: $4662 Traditional Rental Income: $2555 Airbnb ROI: 2% Traditional ROI: 0.39%
110 Boatswain Way #21 CHESTER, MD 110 Boatswain Way #21, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$789,990	Airbnb cash on cash: 4.64% Traditional cash on cash: 1.54% Airbnb Rental Income: $6279 Traditional Rental Income: $2760 Airbnb ROI: 4.64% Traditional ROI: 1.54%
110 Boatswain Way #31 CHESTER, MD 110 Boatswain Way #31, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$889,990	Airbnb cash on cash: 3.89% Traditional cash on cash: 0.96% Airbnb Rental Income: $6279 Traditional Rental Income: $2611 Airbnb ROI: 3.89% Traditional ROI: 0.96%
110 Boatswain Way #32 CHESTER, MD 110 Boatswain Way #32, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$759,990	Airbnb cash on cash: 3% Traditional cash on cash: 1.42% Airbnb Rental Income: $4662 Traditional Rental Income: $2574 Airbnb ROI: 3% Traditional ROI: 1.42%
110 Boatswain Way #33 CHESTER, MD 110 Boatswain Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$759,990	Airbnb cash on cash: 3% Traditional cash on cash: 1.36% Airbnb Rental Income: $4662 Traditional Rental Income: $2530 Airbnb ROI: 3% Traditional ROI: 1.36%
110 Boatswain Way #3041 CHESTER, MD 110 Boatswain Way #3041, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$1,039,990	Airbnb cash on cash: 2.3% Traditional cash on cash: -0.24% Airbnb Rental Income: $6279 Traditional Rental Income: $2592 Airbnb ROI: 2.3% Traditional ROI: -0.24%
110 Boatswain Way #3044 CHESTER, MD 110 Boatswain Way #3044, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$1,134,990	Airbnb cash on cash: 1.93% Traditional cash on cash: -0.39% Airbnb Rental Income: $6279 Traditional Rental Income: $2592 Airbnb ROI: 1.93% Traditional ROI: -0.39%
110 Boatswain Way #3043 CHESTER, MD 110 Boatswain Way #3043, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$859,990	Airbnb cash on cash: 1.53% Traditional cash on cash: 0.1% Airbnb Rental Income: $4662 Traditional Rental Income: $2555 Airbnb ROI: 1.53% Traditional ROI: 0.1%
110 Boatswain Way #3042 CHESTER, MD 110 Boatswain Way #3042, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$859,990	Airbnb cash on cash: 1.53% Traditional cash on cash: 0.1% Airbnb Rental Income: $4662 Traditional Rental Income: $2555 Airbnb ROI: 1.53% Traditional ROI: 0.1%

Your search for investment property begins and ends here

Condos for Sale in Chester, MD

3000 Herons Nest Way #11

CHESTER, MD

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

$555,800

Airbnb cash on cash: 3.08%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $4662

Traditional Rental Income: $2646

Airbnb ROI: 3.08%

Traditional ROI: 1.06%

200 Harrier Way #21

CHESTER, MD

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

$669,900

Airbnb cash on cash: 5.04%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $6279

Traditional Rental Income: $2881

Airbnb ROI: 5.04%

Traditional ROI: 1.58%

1000 Herons Nest Way #23

CHESTER, MD

2 beds | 2 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 #32

CHESTER, MD

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

$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%

111 Marshgrass Way #22

CHESTER, MD

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

$539,000

Airbnb cash on cash: 3.61%

Traditional cash on cash: 1.75%

Airbnb Rental Income: $4662

Traditional Rental Income: $2761

Airbnb ROI: 3.61%

Traditional ROI: 1.75%

176 Flagstaff Way #33

CHESTER, MD

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

$829,990

Airbnb cash on cash: 2.58%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $4662

Traditional Rental Income: $2537

Airbnb ROI: 2.58%

Traditional ROI: 1.08%

176 Flagstaff Way #43

CHESTER, MD

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

$979,990

Airbnb cash on cash: 1.87%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $4662

Traditional Rental Income: $2537

Airbnb ROI: 1.87%