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 47 Condo 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 WATERFRONT Condo! Open House dates scheduled. Beautifully renovated 2BR/2.5BA waterfront c...	2 beds \| 2 baths \| 1,586 sq.ft.	$515,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.53% Airbnb Rental Income: $1989 Traditional Rental Income: $3067 Airbnb ROI: 0.21% Traditional ROI: 3.53%
3000 Herons Nest Way #11 CHESTER, MD A price improvement has been made, making this unit the best value in the entire community...	2 beds \| 2 baths \| 2,003 sq.ft.	$479,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 1.39% Airbnb Rental Income: $1989 Traditional Rental Income: $2646 Airbnb ROI: -1.24% Traditional ROI: 1.39%
4000 Herons Nest Way #22 CHESTER, MD Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 to...	2 beds \| 2 baths \| 1,900 sq.ft.	$515,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 2.37% Airbnb Rental Income: $1989 Traditional Rental Income: $3311 Airbnb ROI: -1.35% Traditional ROI: 2.37%
190 Harrier Way #24 CHESTER, MD Built for low-maintenance living, this beautiful 3-bedroom, 2.5-bath condo offers 2,600 sq...	3 beds \| 2 baths \| 2,602 sq.ft.	$650,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 1.47% Airbnb Rental Income: $3321 Traditional Rental Income: $2881 Airbnb ROI: 0.97% Traditional ROI: 1.47%
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.	$639,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 1.63% Airbnb Rental Income: $3321 Traditional Rental Income: $2881 Airbnb ROI: 1.13% Traditional ROI: 1.63%
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.	$490,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 0.37% Airbnb Rental Income: $1989 Traditional Rental Income: $2331 Airbnb ROI: -1.51% Traditional ROI: 0.37%
302 Merganser Ct #A CHESTER, MD FIRST FLOOR END UNIT IN BAYSIDE!! Kitchen w/Granite counters, breakfast bar, Laminate woo...	2 beds \| 2 baths \| 1,073 sq.ft.	$299,900	Airbnb cash on cash: 1.25% Traditional cash on cash: 2.63% Airbnb Rental Income: $1989 Traditional Rental Income: $1871 Airbnb ROI: 1.25% Traditional ROI: 2.63%
Chester Plan CHESTER, MD Chester Plan, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$544,990	Airbnb cash on cash: 0.83% Traditional cash on cash: 1.76% Airbnb Rental Income: $1989 Traditional Rental Income: $1908 Airbnb ROI: 0.83% Traditional ROI: 1.76%
Magothy Plan CHESTER, MD Magothy Plan, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$544,990	Airbnb cash on cash: 0.83% Traditional cash on cash: 1.81% Airbnb Rental Income: $1989 Traditional Rental Income: $1931 Airbnb ROI: 0.83% Traditional ROI: 1.81%
Severn Plan CHESTER, MD Severn Plan, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$629,990	Airbnb cash on cash: 2.43% Traditional cash on cash: 1.66% Airbnb Rental Income: $3321 Traditional Rental Income: $2155 Airbnb ROI: 2.43% Traditional ROI: 1.66%
110 Boatswain Way #3044 CHESTER, MD 110 Boatswain Way #3044, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$999,990	Airbnb cash on cash: -0.18% Traditional cash on cash: -0.16% Airbnb Rental Income: $3321 Traditional Rental Income: $2592 Airbnb ROI: -0.18% Traditional ROI: -0.16%
110 Boatswain Way #3042 CHESTER, MD 110 Boatswain Way #3042, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$749,990	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.42% Airbnb Rental Income: $1989 Traditional Rental Income: $2555 Airbnb ROI: -1.13% Traditional ROI: 0.42%
110 Boatswain Way #44 CHESTER, MD 110 Boatswain Way #44, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$999,990	Airbnb cash on cash: 0.59% Traditional cash on cash: 0.69% Airbnb Rental Income: $3321 Traditional Rental Income: $2673 Airbnb ROI: 0.59% Traditional ROI: 0.69%
110 Boatswain Way #42 CHESTER, MD 110 Boatswain Way #42, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$749,990	Airbnb cash on cash: -0.11% Traditional cash on cash: 1.55% Airbnb Rental Income: $1989 Traditional Rental Income: $2635 Airbnb ROI: -0.11% Traditional ROI: 1.55%
2000 Herons Nest Way #401 CHESTER, MD Newly adjusted price. Please visit me at the OPEN HOUSE this Sunday from 1-3pm. Rarely ava...	3 beds \| 2 baths \| 2,602 sq.ft.	$700,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 1.42% Airbnb Rental Income: $3321 Traditional Rental Income: $3328 Airbnb ROI: 0.27% Traditional ROI: 1.42%
111 Marshgrass Way #43 CHESTER, MD Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floo...	2 beds \| 2 baths \| N/A	$765,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 1.26% Airbnb Rental Income: $1989 Traditional Rental Income: $3087 Airbnb ROI: -1.01% Traditional ROI: 1.26%
1000 Herons Nest Way #22 CHESTER, MD BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, season...	2 beds \| 2 baths \| 1,900 sq.ft.	$485,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 2.6% Airbnb Rental Income: $1989 Traditional Rental Income: $3207 Airbnb ROI: -1.23% Traditional ROI: 2.6%
132 Wheelhouse Way #11 CHESTER, MD Priced to sell at just $700,000, this is an exceptional opportunity. With a $160,000 lot p...	2 beds \| 2 baths \| 2,003 sq.ft.	$700,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 2.06% Airbnb Rental Income: $1989 Traditional Rental Income: $3272 Airbnb ROI: -0.7% Traditional ROI: 2.06%
102 Boatswain Way #2933 CHESTER, MD 102 Boatswain Way #2933, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$829,990	Airbnb cash on cash: -1.22% Traditional cash on cash: 0.25% Airbnb Rental Income: $1989 Traditional Rental Income: $2610 Airbnb ROI: -1.22% Traditional ROI: 0.25%
102 Boatswain Way #11 CHESTER, MD 102 Boatswain Way #11, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$629,990	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.33% Airbnb Rental Income: $1989 Traditional Rental Income: $2688 Airbnb ROI: 0.26% Traditional ROI: 2.33%
102 Boatswain Way #2911 CHESTER, MD 102 Boatswain Way #2911, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$629,990	Airbnb cash on cash: -0.95% Traditional cash on cash: 1.08% Airbnb Rental Income: $1989 Traditional Rental Income: $2663 Airbnb ROI: -0.95% Traditional ROI: 1.08%
102 Boatswain Way #2912 CHESTER, MD 102 Boatswain Way #2912, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$609,990	Airbnb cash on cash: -0.92% Traditional cash on cash: 1.18% Airbnb Rental Income: $1989 Traditional Rental Income: $2663 Airbnb ROI: -0.92% Traditional ROI: 1.18%
102 Boatswain Way #2921 CHESTER, MD 102 Boatswain Way #2921, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$869,990	Airbnb cash on cash: 0.11% Traditional cash on cash: 0.19% Airbnb Rental Income: $3321 Traditional Rental Income: $2648 Airbnb ROI: 0.11% Traditional ROI: 0.19%
102 Boatswain Way #21 CHESTER, MD 102 Boatswain Way #21, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$869,990	Airbnb cash on cash: 0.99% Traditional cash on cash: 1.1% Airbnb Rental Income: $3321 Traditional Rental Income: $2673 Airbnb ROI: 0.99% Traditional ROI: 1.1%
114 Merganser Ct CHESTER, MD 114 Merganser Ct, CHESTER, MD 21619 \| Townhouse	2 beds \| 2 baths \| 1,069 sq.ft.	$287,500	Airbnb cash on cash: 0.86% Traditional cash on cash: 1.88% Airbnb Rental Income: $1989 Traditional Rental Income: $1754 Airbnb ROI: 0.86% Traditional ROI: 1.88%
102 Boatswain Way #33 CHESTER, MD 102 Boatswain Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$829,990	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.2% Airbnb Rental Income: $1989 Traditional Rental Income: $2635 Airbnb ROI: -0.3% Traditional ROI: 1.2%
102 Boatswain Way #32 CHESTER, MD 102 Boatswain Way #32, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$829,990	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.23% Airbnb Rental Income: $1989 Traditional Rental Income: $2656 Airbnb ROI: -0.3% Traditional ROI: 1.23%
102 Boatswain Way #24 CHESTER, MD 102 Boatswain Way #24, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$819,990	Airbnb cash on cash: 1.17% Traditional cash on cash: 1.33% Airbnb Rental Income: $3321 Traditional Rental Income: $2704 Airbnb ROI: 1.17% Traditional ROI: 1.33%
102 Boatswain Way #43 CHESTER, MD 102 Boatswain Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$929,990	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.89% Airbnb Rental Income: $1989 Traditional Rental Income: $2666 Airbnb ROI: -0.49% Traditional ROI: 0.89%
129 Wheelhouse Way #11 CHESTER, MD Buyers got cold feet- Back on Market but won't last long! Priced well below market value! ...	2 beds \| 2 baths \| N/A	$585,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.86% Airbnb Rental Income: $1989 Traditional Rental Income: $2827 Airbnb ROI: -0.63% Traditional ROI: 1.86%
1000 Herons Nest Way #43 CHESTER, MD Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring ...	2 beds \| 2 baths \| 1,832 sq.ft.	$595,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 2.52% Airbnb Rental Income: $1989 Traditional Rental Income: $3218 Airbnb ROI: -0.63% Traditional ROI: 2.52%
111 Marshgrass Way CHESTER, MD 111 Marshgrass Way, CHESTER, MD 21619 \| Condo/Coop	3 beds \| N/A baths \| 2,602 sq.ft.	$960,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 0.3% Airbnb Rental Income: $3321 Traditional Rental Income: $2223 Airbnb ROI: 0.7% Traditional ROI: 0.3%
830 Warbler Way #21 CHESTER, MD 830 Warbler Way #21, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$749,990	Airbnb cash on cash: 1.47% Traditional cash on cash: 1.63% Airbnb Rental Income: $3321 Traditional Rental Income: $2686 Airbnb ROI: 1.47% Traditional ROI: 1.63%
830 Warbler Way #24 CHESTER, MD 830 Warbler Way #24, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$749,990	Airbnb cash on cash: 1.47% Traditional cash on cash: 1.63% Airbnb Rental Income: $3321 Traditional Rental Income: $2686 Airbnb ROI: 1.47% Traditional ROI: 1.63%
830 Warbler Way #32 CHESTER, MD 830 Warbler Way #32, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$719,815	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.72% Airbnb Rental Income: $1989 Traditional Rental Income: $2648 Airbnb ROI: -0.03% Traditional ROI: 1.72%
830 Warbler Way #34 CHESTER, MD 830 Warbler Way #34, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$849,990	Airbnb cash on cash: 1.06% Traditional cash on cash: 1.19% Airbnb Rental Income: $3321 Traditional Rental Income: $2686 Airbnb ROI: 1.06% Traditional ROI: 1.19%
830 Warbler Way #33 CHESTER, MD 830 Warbler Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$689,990	Airbnb cash on cash: 0.05% Traditional cash on cash: 1.89% Airbnb Rental Income: $1989 Traditional Rental Income: $2648 Airbnb ROI: 0.05% Traditional ROI: 1.89%
830 Warbler Way #43 CHESTER, MD 830 Warbler Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$789,990	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.39% Airbnb Rental Income: $1989 Traditional Rental Income: $2648 Airbnb ROI: -0.21% Traditional ROI: 1.39%
830 Warbler Way #42 CHESTER, MD 830 Warbler Way #42, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$789,990	Airbnb cash on cash: -0.21% Traditional cash on cash: 1.39% Airbnb Rental Income: $1989 Traditional Rental Income: $2648 Airbnb ROI: -0.21% Traditional ROI: 1.39%
830 Warbler Way #31 CHESTER, MD 830 Warbler Way #31, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$849,990	Airbnb cash on cash: 1.06% Traditional cash on cash: 1.19% Airbnb Rental Income: $3321 Traditional Rental Income: $2686 Airbnb ROI: 1.06% Traditional ROI: 1.19%

Your search for investment property begins and ends here

Condos for Sale in Chester, MD

34-E Queen Anne Way

CHESTER, MD

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

$515,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $1989

Traditional Rental Income: $3067

Airbnb ROI: 0.21%

Traditional ROI: 3.53%

3000 Herons Nest Way #11

CHESTER, MD

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

$479,000

Airbnb cash on cash: -1.24%

Traditional cash on cash: 1.39%

Airbnb Rental Income: $1989

Traditional Rental Income: $2646

Airbnb ROI: -1.24%

Traditional ROI: 1.39%

4000 Herons Nest Way #22

CHESTER, MD

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

$515,000

Airbnb cash on cash: -1.35%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $1989

Traditional Rental Income: $3311

Airbnb ROI: -1.35%

Traditional ROI: 2.37%

190 Harrier Way #24

CHESTER, MD

3 beds | 2 baths | 2,602 sq.ft.

$650,000

Airbnb cash on cash: 0.97%

Traditional cash on cash: 1.47%

Airbnb Rental Income: $3321

Traditional Rental Income: $2881

Airbnb ROI: 0.97%

Traditional ROI: 1.47%

200 Harrier Way #21

CHESTER, MD

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

$639,900

Airbnb cash on cash: 1.13%

Traditional cash on cash: 1.63%

Airbnb Rental Income: $3321

Traditional Rental Income: $2881

Airbnb ROI: 1.13%

Traditional ROI: 1.63%

1000 Herons Nest Way #23

CHESTER, MD

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

$490,000

Airbnb cash on cash: -1.51%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $1989

Traditional Rental Income: $2331

Airbnb ROI: -1.51%

Traditional ROI: 0.37%

302 Merganser Ct #A

CHESTER, MD

2 beds | 2 baths | 1,073 sq.ft.

$299,900

Airbnb cash on cash: 1.25%

Traditional cash on cash: 2.63%

Airbnb Rental Income: $1989

Traditional Rental Income: $1871

Airbnb ROI: 1.25%

Traditional ROI: 2.63%

Chester Plan

CHESTER, MD

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

$544,990

Airbnb cash on cash: 0.83%

Traditional cash on cash: 1.76%

Airbnb Rental Income: $1989

Traditional Rental Income: $1908

Airbnb ROI: 0.83%