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 30 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
3000 Herons Nest Way #11 CHESTER, MD Call today to find out the details and start living the life you want. Welcome to a new a...	2 beds \| 2 baths \| 2,003 sq.ft.	$555,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 0.49% Airbnb Rental Income: $4662 Traditional Rental Income: $2530 Airbnb ROI: 2.74% Traditional ROI: 0.49%
170 HARRIER WAY #34 CHESTER, MD New year, new price!! This is one of only two 3-bedroom condos on the market in Four Seas...	3 beds \| 3 baths \| N/A	$699,900	Airbnb cash on cash: 5.77% Traditional cash on cash: 2.61% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.77% Traditional ROI: 2.61%
190 HARRIER Way unit: 11 #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: 3.92% Traditional cash on cash: 1.26% Airbnb Rental Income: $4662 Traditional Rental Income: $2354 Airbnb ROI: 3.92% Traditional ROI: 1.26%
306 Teal Ct #C CHESTER, MD	2 beds \| 2 baths \| 1,073 sq.ft.	$279,900	Airbnb cash on cash: 9.87% Traditional cash on cash: 5.45% Airbnb Rental Income: $4662 Traditional Rental Income: $2530 Airbnb ROI: 9.87% Traditional ROI: 5.45%
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.	$674,900	Airbnb cash on cash: 4.99% Traditional cash on cash: 1.56% Airbnb Rental Income: $6279 Traditional Rental Income: $2881 Airbnb ROI: 4.99% Traditional ROI: 1.56%
1000 HERONS NEST Way unit: 32 #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: 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 #22 CHESTER, MD Four Seasons @ Kent Island - 55+ Community - $10,000 Closing Cost Assistance Available - T...	2 beds \| 2 baths \| 1,900 sq.ft.	$560,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 1.79% Airbnb Rental Income: $4662 Traditional Rental Income: $3075 Airbnb ROI: 2.98% Traditional ROI: 1.79%
201 Golden Eye Ct CHESTER, MD Bright, welcoming lower level end unit condo in a water-oriented community on Kent Island...	2 beds \| 2 baths \| 1,073 sq.ft.	$285,000	Airbnb cash on cash: 9.86% Traditional cash on cash: 3.09% Airbnb Rental Income: $4662 Traditional Rental Income: $1878 Airbnb ROI: 9.86% Traditional ROI: 3.09%
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%
3000 HERONS NEST Way unit: 11 #11 CHESTER, MD Love Where You Live! Experience resort-style living that blends comfort, luxury, and conve...	2 beds \| 3 baths \| 2,003 sq.ft.	$555,900	Airbnb cash on cash: 5.2% Traditional cash on cash: 4% Airbnb Rental Income: $4662 Traditional Rental Income: $3069 Airbnb ROI: 5.2% Traditional ROI: 4%
10-B QUEEN ELIZABETH CT CHESTER, MD EXCELLENT PRICE IMPROVEMENT ON THIS CHESTER RIVER WATERFRONT !!! Spectacular sunrise views...	1 beds \| 1 baths \| N/A	$310,000	Airbnb cash on cash: 6.67% Traditional cash on cash: 2.02% Airbnb Rental Income: $3572 Traditional Rental Income: $1430 Airbnb ROI: 6.67% Traditional ROI: 2.02%
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%
15-E QUEEN ANNE Way unit: E #E CHESTER, MD Escape to the water - without the waterfront price. This Chester River-front townhome in Q...	2 beds \| 3 baths \| 1,680 sq.ft.	$480,000	Airbnb cash on cash: 4.99% Traditional cash on cash: 3.85% Airbnb Rental Income: $4662 Traditional Rental Income: $3186 Airbnb ROI: 4.99% Traditional ROI: 3.85%
4000 HERONS NEST Way unit: 22 #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: 5.1% Traditional cash on cash: 3.83% Airbnb Rental Income: $4662 Traditional Rental Income: $3029 Airbnb ROI: 5.1% Traditional ROI: 3.83%
176 Flagstaff Way #33 CHESTER, MD 176 Flagstaff Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$869,990	Airbnb cash on cash: 2.36% Traditional cash on cash: 0.93% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 2.36% Traditional ROI: 0.93%
176 Flagstaff Way #43 CHESTER, MD 176 Flagstaff Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$1,021,990	Airbnb cash on cash: 1.71% Traditional cash on cash: 0.48% Airbnb Rental Income: $4662 Traditional Rental Income: $2530 Airbnb ROI: 1.71% Traditional ROI: 0.48%
176 Flagstaff Way #2443 CHESTER, MD 176 Flagstaff Way #2443, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$1,021,990	Airbnb cash on cash: 1% Traditional cash on cash: -0.22% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1% Traditional ROI: -0.22%
176 Flagstaff Way #2433 CHESTER, MD 176 Flagstaff Way #2433, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$869,990	Airbnb cash on cash: 1.54% Traditional cash on cash: 0.11% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.54% Traditional ROI: 0.11%
176 Flagstaff Way #24 CHESTER, MD 176 Flagstaff Way #24, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$935,990	Airbnb cash on cash: 3.6% Traditional cash on cash: 0.77% Airbnb Rental Income: $6279 Traditional Rental Income: $2582 Airbnb ROI: 3.6% Traditional ROI: 0.77%
176 Flagstaff Way #2424 CHESTER, MD 176 Flagstaff Way #2424, CHESTER, MD 21619 \| Condo/Coop	3 beds \| 2 baths \| 2,602 sq.ft.	$935,990	Airbnb cash on cash: 2.83% Traditional cash on cash: 0.01% Airbnb Rental Income: $6279 Traditional Rental Income: $2582 Airbnb ROI: 2.83% Traditional ROI: 0.01%
176 Flagstaff Way #12 CHESTER, MD 176 Flagstaff Way #12, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$699,990	Airbnb cash on cash: 3.44% Traditional cash on cash: 1.74% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 3.44% Traditional ROI: 1.74%
176 Flagstaff Way #2411 CHESTER, MD 176 Flagstaff Way #2411, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$699,990	Airbnb cash on cash: 2.41% Traditional cash on cash: 0.63% Airbnb Rental Income: $4662 Traditional Rental Income: $2530 Airbnb ROI: 2.41% Traditional ROI: 0.63%
176 Flagstaff Way #11 CHESTER, MD 176 Flagstaff Way #11, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$699,990	Airbnb cash on cash: 3.44% Traditional cash on cash: 1.74% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 3.44% Traditional ROI: 1.74%
176 Flagstaff Way #2412 CHESTER, MD 176 Flagstaff Way #2412, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$699,990	Airbnb cash on cash: 2.41% Traditional cash on cash: 0.72% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 2.41% Traditional ROI: 0.72%
132 Wheelhouse Way #43 CHESTER, MD 132 Wheelhouse Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$1,350,000	Airbnb cash on cash: 0.79% Traditional cash on cash: -0.14% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 0.79% Traditional ROI: -0.14%
132 Wheelhouse Way CHESTER, MD 132 Wheelhouse Way, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$1,299,990	Airbnb cash on cash: 0.35% Traditional cash on cash: -0.62% Airbnb Rental Income: $4662 Traditional Rental Income: $2530 Airbnb ROI: 0.35% Traditional ROI: -0.62%
Chester Plan CHESTER, MD	2 beds \| 2 baths \| 1,900 sq.ft.	$489,990	Airbnb cash on cash: 5.78% Traditional cash on cash: 3.24% Airbnb Rental Income: $4662 Traditional Rental Income: $2530 Airbnb ROI: 5.78% Traditional ROI: 3.24%
Magothy Plan CHESTER, MD	2 beds \| 2 baths \| 2,003 sq.ft.	$489,990	Airbnb cash on cash: 5.78% Traditional cash on cash: 1.93% Airbnb Rental Income: $4662 Traditional Rental Income: $1931 Airbnb ROI: 5.78% Traditional ROI: 1.93%
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: 4.04% Traditional cash on cash: 1.56% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 4.04% Traditional ROI: 1.56%
Severn Plan CHESTER, MD	3 beds \| 2 baths \| 2,602 sq.ft.	$574,990	Airbnb cash on cash: 7.14% Traditional cash on cash: 1.76% Airbnb Rental Income: $6279 Traditional Rental Income: $2155 Airbnb ROI: 7.14% Traditional ROI: 1.76%

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.

$555,900

Airbnb cash on cash: 2.74%

Traditional cash on cash: 0.49%

Airbnb Rental Income: $4662

Traditional Rental Income: $2530

Airbnb ROI: 2.74%

Traditional ROI: 0.49%

170 HARRIER WAY #34

CHESTER, MD

3 beds | 3 baths | N/A

$699,900

Airbnb cash on cash: 5.77%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $6279

Traditional Rental Income: $2981

Airbnb ROI: 5.77%

Traditional ROI: 2.61%

190 HARRIER Way unit: 11 #11

CHESTER, MD

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

$540,000

Airbnb cash on cash: 3.92%

Traditional cash on cash: 1.26%

Airbnb Rental Income: $4662

Traditional Rental Income: $2354

Airbnb ROI: 3.92%

Traditional ROI: 1.26%

306 Teal Ct #C

CHESTER, MD

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

$279,900

Airbnb cash on cash: 9.87%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $4662

Traditional Rental Income: $2530

Airbnb ROI: 9.87%

Traditional ROI: 5.45%

200 Harrier Way #21

CHESTER, MD

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

$674,900

Airbnb cash on cash: 4.99%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $6279

Traditional Rental Income: $2881

Airbnb ROI: 4.99%

Traditional ROI: 1.56%

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 #22

CHESTER, MD

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

$560,000

Airbnb cash on cash: 2.98%

Traditional cash on cash: 1.79%

Airbnb Rental Income: $4662

Traditional Rental Income: $3075

Airbnb ROI: 2.98%

Traditional ROI: 1.79%

201 Golden Eye Ct

CHESTER, MD

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

$285,000

Airbnb cash on cash: 9.86%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $4662

Traditional Rental Income: $1878

Airbnb ROI: 9.86%