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 40 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
200 SCHOONER WAY CHESTER, MD Just minutes over the Chesapeake Bay Bridge, this beautifully maintained end-unit townhome...	3 beds \| 4 baths \| N/A	$550,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.75% Airbnb Rental Income: $2190 Traditional Rental Income: $3663 Airbnb ROI: -0.2% Traditional ROI: 3.75%
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: 0.2% Traditional cash on cash: 3.25% Airbnb Rental Income: $2028 Traditional Rental Income: $3067 Airbnb ROI: 0.2% Traditional ROI: 3.25%
1025 DUNDEE Court CHESTER, MD Welcome home to this Amazingly priced townhome on Kent Island! Square foot pricing like th...	3 beds \| 3 baths \| 1,400 sq.ft.	$350,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 5.29% Airbnb Rental Income: $2190 Traditional Rental Income: $2606 Airbnb ROI: 2.34% Traditional ROI: 5.29%
4000 HERONS NEST Way #22 CHESTER, MD Four Seasons @ Kent Island - 55+ Community - Turn-key & Lovely 2nd Floor Condo in Elevator...	2 beds \| 3 baths \| 1,900 sq.ft.	$560,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.21% Airbnb Rental Income: $2028 Traditional Rental Income: $3311 Airbnb ROI: -1.25% Traditional ROI: 2.21%
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.	$649,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 1.66% Airbnb Rental Income: $2190 Traditional Rental Income: $2881 Airbnb ROI: -0.4% Traditional ROI: 1.66%
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 \| 3 baths \| 2,003 sq.ft.	$494,900	Airbnb cash on cash: -1.42% Traditional cash on cash: 0.37% Airbnb Rental Income: $2028 Traditional Rental Income: $2331 Airbnb ROI: -1.42% Traditional ROI: 0.37%
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	$529,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.44% Airbnb Rental Income: $2028 Traditional Rental Income: $2761 Airbnb ROI: 0.89% Traditional ROI: 3.44%
54-H QUEEN CAROLINE CT CHESTER, MD Owners have lowered the price by $10,000 and are willing to look at offers! Nothing to do ...	2 beds \| 3 baths \| N/A	$339,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 2.65% Airbnb Rental Income: $2028 Traditional Rental Income: $2064 Airbnb ROI: 0.88% Traditional ROI: 2.65%
Chester Plan CHESTER, MD	2 beds \| 2 baths \| 1,900 sq.ft.	$504,990	Airbnb cash on cash: 0.9% Traditional cash on cash: 1.76% Airbnb Rental Income: $2028 Traditional Rental Income: $1908 Airbnb ROI: 0.9% Traditional ROI: 1.76%
Magothy Plan CHESTER, MD	2 beds \| 2 baths \| 2,003 sq.ft.	$504,990	Airbnb cash on cash: 0.9% Traditional cash on cash: 1.81% Airbnb Rental Income: $2028 Traditional Rental Income: $1931 Airbnb ROI: 0.9% Traditional ROI: 1.81%
Severn Plan CHESTER, MD	3 beds \| 2 baths \| 2,602 sq.ft.	$589,990	Airbnb cash on cash: 0.72% Traditional cash on cash: 1.66% Airbnb Rental Income: $2190 Traditional Rental Income: $2155 Airbnb ROI: 0.72% Traditional ROI: 1.66%
110 Boatswain Way #3032 CHESTER, MD 110 Boatswain Way #3032, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$699,990	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.6% Airbnb Rental Income: $2028 Traditional Rental Income: $2555 Airbnb ROI: -1.02% Traditional ROI: 0.6%
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: -0.44% Traditional cash on cash: 3.02% Airbnb Rental Income: $988 Traditional Rental Income: $1511 Airbnb ROI: -0.44% Traditional ROI: 3.02%
110 Boatswain Way #32 CHESTER, MD 110 Boatswain Way #32, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$699,990	Airbnb cash on cash: 0.07% Traditional cash on cash: 1.72% Airbnb Rental Income: $2028 Traditional Rental Income: $2574 Airbnb ROI: 0.07% Traditional ROI: 1.72%
110 Boatswain Way #3042 CHESTER, MD 110 Boatswain Way #3042, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$799,990	Airbnb cash on cash: -1.15% Traditional cash on cash: 0.27% Airbnb Rental Income: $2028 Traditional Rental Income: $2555 Airbnb ROI: -1.15% Traditional ROI: 0.27%
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	$247,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 2.51% Airbnb Rental Income: $988 Traditional Rental Income: $1309 Airbnb ROI: -0.38% Traditional ROI: 2.51%
110 Boatswain Way #42 CHESTER, MD 110 Boatswain Way #42, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$799,990	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.33% Airbnb Rental Income: $2028 Traditional Rental Income: $2635 Airbnb ROI: -0.19% Traditional ROI: 1.33%
2000 HERONS NEST Way #401 CHESTER, MD This rare, luxurious Severn penthouse in Four Seasons at Kent Island is available immediat...	3 beds \| 3 baths \| 2,602 sq.ft.	$750,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 1.26% Airbnb Rental Income: $2190 Traditional Rental Income: $3328 Airbnb ROI: -1.16% Traditional ROI: 1.26%
34 QUEEN ANNE Way #F CHESTER, MD Rare Opportunity in Queen's Landing with Stunning Chester River Views Welcome to one of th...	1 beds \| 1 baths \| 724 sq.ft.	$349,900	Airbnb cash on cash: -0.75% Traditional cash on cash: 2.4% Airbnb Rental Income: $988 Traditional Rental Income: $1670 Airbnb ROI: -0.75% Traditional ROI: 2.4%
1000 HERONS NEST Way #402 CHESTER, MD Rarely on the market Penthouse level Chester model available immediately! Balcony views fr...	2 beds \| 3 baths \| 1,900 sq.ft.	$599,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 1.72% Airbnb Rental Income: $2028 Traditional Rental Income: $3142 Airbnb ROI: -1.21% Traditional ROI: 1.72%
111 MARSHGRASS WAY #43 CHESTER, MD Rare penthouse unit with year-round water views perfectly positioned to capture stunning s...	2 beds \| 3 baths \| N/A	$765,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 1.26% Airbnb Rental Income: $2028 Traditional Rental Income: $3087 Airbnb ROI: -0.96% 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 \| 3 baths \| 1,900 sq.ft.	$488,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 2.58% Airbnb Rental Income: $2028 Traditional Rental Income: $3207 Airbnb ROI: -1.16% Traditional ROI: 2.58%
132 WHEELHOUSE Way #11 CHESTER, MD Experience refined coastal living at 132 Wheelhouse Way #11, where the highly desirable Ma...	2 beds \| 3 baths \| 2,003 sq.ft.	$799,900	Airbnb cash on cash: -0.7% Traditional cash on cash: 1.68% Airbnb Rental Income: $2028 Traditional Rental Income: $3272 Airbnb ROI: -0.7% Traditional ROI: 1.68%
102 Boatswain Way #2933 CHESTER, MD 102 Boatswain Way #2933, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$849,990	Airbnb cash on cash: -1.2% Traditional cash on cash: 0.2% Airbnb Rental Income: $2028 Traditional Rental Income: $2610 Airbnb ROI: -1.2% Traditional ROI: 0.2%
102 Boatswain Way #11 CHESTER, MD 102 Boatswain Way #11, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$649,990	Airbnb cash on cash: 0.24% Traditional cash on cash: 2.2% Airbnb Rental Income: $2028 Traditional Rental Income: $2688 Airbnb ROI: 0.24% Traditional ROI: 2.2%
102 Boatswain Way #2934 CHESTER, MD 102 Boatswain Way #2934, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$989,990	Airbnb cash on cash: -1.18% Traditional cash on cash: -0.08% Airbnb Rental Income: $2190 Traditional Rental Income: $2648 Airbnb ROI: -1.18% Traditional ROI: -0.08%
102 Boatswain Way #34 CHESTER, MD 102 Boatswain Way #34, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$989,990	Airbnb cash on cash: -0.41% Traditional cash on cash: 0.72% Airbnb Rental Income: $2190 Traditional Rental Income: $2673 Airbnb ROI: -0.41% Traditional ROI: 0.72%
102 Boatswain Way #12 CHESTER, MD 102 Boatswain Way #12, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$649,990	Airbnb cash on cash: 0.24% Traditional cash on cash: 2.2% Airbnb Rental Income: $2028 Traditional Rental Income: $2688 Airbnb ROI: 0.24% Traditional ROI: 2.2%
102 Boatswain Way #2911 CHESTER, MD 102 Boatswain Way #2911, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$649,990	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.98% Airbnb Rental Income: $2028 Traditional Rental Income: $2663 Airbnb ROI: -0.93% Traditional ROI: 0.98%
102 Boatswain Way #2912 CHESTER, MD 102 Boatswain Way #2912, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$649,990	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.98% Airbnb Rental Income: $2028 Traditional Rental Income: $2663 Airbnb ROI: -0.93% Traditional ROI: 0.98%
102 Boatswain Way #2921 CHESTER, MD 102 Boatswain Way #2921, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$889,990	Airbnb cash on cash: -1.08% Traditional cash on cash: 0.14% Airbnb Rental Income: $2190 Traditional Rental Income: $2648 Airbnb ROI: -1.08% Traditional ROI: 0.14%
102 Boatswain Way #21 CHESTER, MD 102 Boatswain Way #21, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$889,990	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.03% Airbnb Rental Income: $2190 Traditional Rental Income: $2673 Airbnb ROI: -0.22% Traditional ROI: 1.03%
208 BLENNY Lane CHESTER, MD PRICE REDUCTION! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Tow...	3 beds \| 4 baths \| 1,899 sq.ft.	$434,900	Airbnb cash on cash: 0.46% Traditional cash on cash: 4.6% Airbnb Rental Income: $2190 Traditional Rental Income: $3322 Airbnb ROI: 0.46% Traditional ROI: 4.6%
111 MARSHGRASS Way #21 CHESTER, MD A rare blend of coastal proximity and refined living unfolds approximately 500 feet from a...	3 beds \| 3 baths \| 2,602 sq.ft.	$680,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 1.64% Airbnb Rental Income: $2190 Traditional Rental Income: $3249 Airbnb ROI: -0.91% Traditional ROI: 1.64%
114 Merganser Ct CHESTER, MD 114 Merganser Ct, CHESTER, MD 21619 \| Townhouse	2 beds \| 2 baths \| 1,069 sq.ft.	$299,500	Airbnb cash on cash: 0.93% Traditional cash on cash: 1.83% Airbnb Rental Income: $2028 Traditional Rental Income: $1754 Airbnb ROI: 0.93% Traditional ROI: 1.83%
102 Boatswain Way #33 CHESTER, MD 102 Boatswain Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$849,990	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.13% Airbnb Rental Income: $2028 Traditional Rental Income: $2635 Airbnb ROI: -0.3% Traditional ROI: 1.13%
102 Boatswain Way #42 CHESTER, MD 102 Boatswain Way #42, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$949,990	Airbnb cash on cash: -0.49% Traditional cash on cash: 0.82% Airbnb Rental Income: $2028 Traditional Rental Income: $2656 Airbnb ROI: -0.49% Traditional ROI: 0.82%
102 Boatswain Way #41 CHESTER, MD 102 Boatswain Way #41, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$1,139,990	Airbnb cash on cash: -0.63% Traditional cash on cash: 0.37% Airbnb Rental Income: $2190 Traditional Rental Income: $2694 Airbnb ROI: -0.63% Traditional ROI: 0.37%
102 Boatswain Way #32 CHESTER, MD 102 Boatswain Way #32, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$849,990	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.15% Airbnb Rental Income: $2028 Traditional Rental Income: $2656 Airbnb ROI: -0.3% Traditional ROI: 1.15%
54-F QUEEN CAROLINE CT CHESTER, MD Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters...	3 beds \| 3 baths \| N/A	$375,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 2.07% Airbnb Rental Income: $2190 Traditional Rental Income: $2006 Airbnb ROI: 1.02% Traditional ROI: 2.07%

Your search for investment property begins and ends here

Condos for Sale in Chester, MD

200 SCHOONER WAY

CHESTER, MD

3 beds | 4 baths | N/A

$550,000

Airbnb cash on cash: -0.2%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2190

Traditional Rental Income: $3663

Airbnb ROI: -0.2%

Traditional ROI: 3.75%

34-E QUEEN ANNE Way

CHESTER, MD

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

$549,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $2028

Traditional Rental Income: $3067

Airbnb ROI: 0.2%

Traditional ROI: 3.25%

1025 DUNDEE Court

CHESTER, MD

3 beds | 3 baths | 1,400 sq.ft.

$350,000

Airbnb cash on cash: 2.34%

Traditional cash on cash: 5.29%

Airbnb Rental Income: $2190

Traditional Rental Income: $2606

Airbnb ROI: 2.34%

Traditional ROI: 5.29%

4000 HERONS NEST Way #22

CHESTER, MD

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

$560,000

Airbnb cash on cash: -1.25%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $2028

Traditional Rental Income: $3311

Airbnb ROI: -1.25%

Traditional ROI: 2.21%

200 Harrier Way #21

CHESTER, MD

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

$649,900

Airbnb cash on cash: -0.4%

Traditional cash on cash: 1.66%

Airbnb Rental Income: $2190

Traditional Rental Income: $2881

Airbnb ROI: -0.4%

Traditional ROI: 1.66%

1000 HERONS NEST WAY #23

CHESTER, MD

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

$494,900

Airbnb cash on cash: -1.42%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $2028

Traditional Rental Income: $2331

Airbnb ROI: -1.42%

Traditional ROI: 0.37%

111 MARSHGRASS WAY #22

CHESTER, MD

2 beds | 3 baths | N/A

$529,900

Airbnb cash on cash: 0.89%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $2028

Traditional Rental Income: $2761

Airbnb ROI: 0.89%

Traditional ROI: 3.44%

54-H QUEEN CAROLINE CT

CHESTER, MD

2 beds | 3 baths | N/A

$339,000

Airbnb cash on cash: 0.88%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $2028

Traditional Rental Income: $2064

Airbnb ROI: 0.88%