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.

Investment Property for Sale in Chester, MD

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1012 AUCKLAND Way CHESTER, MD Experience the best of Kent Island waterfront living in this beautifully appointed home lo...	3 beds \| 4 baths \| 2,076 sq.ft.	$599,900	Airbnb cash on cash: 0.51% Traditional cash on cash: 4.17% Airbnb Rental Income: $2714 Traditional Rental Income: $4122 Airbnb ROI: 0.51% Traditional ROI: 4.17%
34-E QUEEN ANNE Way CHESTER, MD WATERFRONT Condo! Open House to be scheduled soon! Beautifully renovated 2BR/2.5BA waterfr...	2 beds \| 3 baths \| 1,586 sq.ft.	$515,000	Airbnb cash on cash: 0.24% Traditional cash on cash: 3.53% Airbnb Rental Income: $2009 Traditional Rental Income: $3067 Airbnb ROI: 0.24% Traditional ROI: 3.53%
115 GIBSON CIR CHESTER, MD Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxu...	2 beds \| 3 baths \| N/A	$575,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 2.79% Airbnb Rental Income: $2009 Traditional Rental Income: $2534 Airbnb ROI: 0.84% Traditional ROI: 2.79%
2008 BRIDGEPOINTE Drive CHESTER, MD Welcome to this gorgeous end unit townhouse offering low-maintenance living in a highly co...	2 beds \| 2 baths \| 1,804 sq.ft.	$380,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 4.97% Airbnb Rental Income: $2009 Traditional Rental Income: $2725 Airbnb ROI: 1.5% Traditional ROI: 4.97%
5011 BRIDGEPOINTE Drive CHESTER, MD Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome wit...	3 beds \| 3 baths \| 1,302 sq.ft.	$374,900	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.63% Airbnb Rental Income: $2714 Traditional Rental Income: $2543 Airbnb ROI: 3.3% Traditional ROI: 4.63%
1025 DUNDEE Court CHESTER, MD Estate Sale! Motivated Seller offering $5,000.00 in closing costs help! OPEN House this Sa...	3 beds \| 3 baths \| 1,400 sq.ft.	$324,900	Airbnb cash on cash: 4.02% Traditional cash on cash: 5.77% Airbnb Rental Income: $2714 Traditional Rental Income: $2606 Airbnb ROI: 4.02% Traditional ROI: 5.77%
4000 HERONS NEST Way #22 CHESTER, MD Four Seasons @ Kent Island - 55+ Community - Price Improvement + Seller to Credit $4000 to...	2 beds \| 3 baths \| 1,900 sq.ft.	$530,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 2.37% Airbnb Rental Income: $2009 Traditional Rental Income: $3311 Airbnb ROI: -1.32% Traditional ROI: 2.37%
106 BODYS NECK Road CHESTER, MD Welcome to Bayside, where coastal living and resort-style amenities come together in one o...	3 beds \| 3 baths \| 1,595 sq.ft.	$435,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.33% Airbnb Rental Income: $2714 Traditional Rental Income: $2829 Airbnb ROI: 1.47% Traditional ROI: 3.33%
124 RIVERSIDE Drive CHESTER, MD Gorgeous, like-new home on Kent Island! VA ASSUMABLE at 2.75% Interest!! Call for details!...	4 beds \| 3 baths \| 1,979 sq.ft.	$545,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 4.28% Airbnb Rental Income: $3976 Traditional Rental Income: $3150 Airbnb ROI: 4.23% Traditional ROI: 4.28%
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 \| 3 baths \| 2,602 sq.ft.	$650,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 1.47% Airbnb Rental Income: $2714 Traditional Rental Income: $2881 Airbnb ROI: 0.14% Traditional ROI: 1.47%
134 MCHENNY Court CHESTER, MD Just Reduced! Best value in Gibsons Grant. Welcome home to this beautifully maintained thr...	3 beds \| 3 baths \| 1,839 sq.ft.	$579,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 2.72% Airbnb Rental Income: $2714 Traditional Rental Income: $2785 Airbnb ROI: 1.41% Traditional ROI: 2.72%
1868 ROBERTA Drive CHESTER, MD Price improvement! Motivated sellers. This custom built home offers the perfect opportunit...	5 beds \| 4 baths \| 3,250 sq.ft.	$724,500	Airbnb cash on cash: -1.87% Traditional cash on cash: 3.9% Airbnb Rental Income: $267 Traditional Rental Income: $3937 Airbnb ROI: -1.87% Traditional ROI: 3.9%
1340 QUEEN ANNE Drive CHESTER, MD PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-priv...	3 beds \| 2 baths \| 1,248 sq.ft.	$439,900	Airbnb cash on cash: 3.24% Traditional cash on cash: 4.01% Airbnb Rental Income: $2714 Traditional Rental Income: $2393 Airbnb ROI: 3.24% Traditional ROI: 4.01%
1916 STEVENS Drive CHESTER, MD This beautifully updated and well maintained home delivers exceptional value in the highly...	3 beds \| 3 baths \| 1,728 sq.ft.	$475,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 4.61% Airbnb Rental Income: $2714 Traditional Rental Income: $2880 Airbnb ROI: 2.79% Traditional ROI: 4.61%
54-H QUEEN CAROLINE CT CHESTER, MD DON""T MISS OUT on this super deal!! Owners have lowered the price by $10,000 and are will...	2 beds \| 3 baths \| N/A	$329,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 2.76% Airbnb Rental Income: $2009 Traditional Rental Income: $2064 Airbnb ROI: 0.89% Traditional ROI: 2.76%
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: 0.93% Traditional cash on cash: 3.02% Airbnb Rental Income: $1403 Traditional Rental Income: $1511 Airbnb ROI: 0.93% Traditional ROI: 3.02%
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	$240,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 2.61% Airbnb Rental Income: $1403 Traditional Rental Income: $1309 Airbnb ROI: 1.16% Traditional ROI: 2.61%
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 \| 3 baths \| 2,602 sq.ft.	$700,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 1.42% Airbnb Rental Income: $2714 Traditional Rental Income: $3328 Airbnb ROI: -0.51% Traditional ROI: 1.42%
215 KINGFISHER Lane CHESTER, MD Price Reduced $50K - Check out the Virtual Tour! Exceptional Value in Four Seasons at Kent...	5 beds \| 5 baths \| 3,225 sq.ft.	$1,049,500	Airbnb cash on cash: -2.1% Traditional cash on cash: 2.76% Airbnb Rental Income: $267 Traditional Rental Income: $4779 Airbnb ROI: -2.1% Traditional ROI: 2.76%
111 MARSHGRASS WAY #43 CHESTER, MD Penthouse Unit! Seller offering closing cost assistance to qualified buyers! Rare top floo...	2 beds \| 3 baths \| N/A	$765,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 1.26% Airbnb Rental Income: $2009 Traditional Rental Income: $3087 Airbnb ROI: -0.99% 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.	$485,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 2.6% Airbnb Rental Income: $2009 Traditional Rental Income: $3207 Airbnb ROI: -1.19% Traditional ROI: 2.6%
132 WHEELHOUSE WAY #11 CHESTER, MD Adjusted price and ready for new owners!! Experience everything Four Seasons has to offer ...	2 beds \| 3 baths \| 2,003 sq.ft.	$729,999	Airbnb cash on cash: -0.69% Traditional cash on cash: 1.93% Airbnb Rental Income: $2009 Traditional Rental Income: $3272 Airbnb ROI: -0.69% Traditional ROI: 1.93%
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: 1.53% Traditional cash on cash: 4.6% Airbnb Rental Income: $2714 Traditional Rental Income: $3322 Airbnb ROI: 1.53% Traditional ROI: 4.6%
111 MARSHGRASS Way #21 CHESTER, MD A rare blend of coastal proximity and refined living unfolds within this beautifully appoi...	3 beds \| 3 baths \| 2,602 sq.ft.	$680,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 1.94% Airbnb Rental Income: $2714 Traditional Rental Income: $3249 Airbnb ROI: 0.08% Traditional ROI: 1.94%
126 WATERMANS COVE Lane CHESTER, MD Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman's Cove...	3 beds \| 3 baths \| 1,536 sq.ft.	$559,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 3.2% Airbnb Rental Income: $2714 Traditional Rental Income: $2748 Airbnb ROI: 1.9% Traditional ROI: 3.2%
54F 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	$359,900	Airbnb cash on cash: 2.4% Traditional cash on cash: 2.2% Airbnb Rental Income: $2714 Traditional Rental Income: $2006 Airbnb ROI: 2.4% Traditional ROI: 2.2%
45-G QUEEN NEVA Court CHESTER, MD Seller is offering closing cost assistance for qualified buyers! This charming townhouse i...	2 beds \| 3 baths \| 1,312 sq.ft.	$349,500	Airbnb cash on cash: 0.9% Traditional cash on cash: 3.47% Airbnb Rental Income: $2009 Traditional Rental Income: $2329 Airbnb ROI: 0.9% Traditional ROI: 3.47%
6005 BRIDGEPOINTE Drive CHESTER, MD Low maintenance island living at its best! 6005 Bridgepointe Dr is freshly painted, deep c...	3 beds \| 3 baths \| 1,302 sq.ft.	$357,900	Airbnb cash on cash: 3.5% Traditional cash on cash: 4.78% Airbnb Rental Income: $2714 Traditional Rental Income: $2502 Airbnb ROI: 3.5% Traditional ROI: 4.78%
108 CARRIAGE HEATH CHESTER, MD Price improvement. A rare opportunity to own one of the largest and most beautiful homes i...	5 beds \| 4 baths \| 4,334 sq.ft.	$1,249,000	Airbnb cash on cash: -1.99% Traditional cash on cash: 1.46% Airbnb Rental Income: $267 Traditional Rental Income: $4034 Airbnb ROI: -1.99% Traditional ROI: 1.46%
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 \| 3 baths \| N/A	$585,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.73% Airbnb Rental Income: $2009 Traditional Rental Income: $2827 Airbnb ROI: -0.73% Traditional ROI: 1.73%
134 RICHARD INGLE Way CHESTER, MD Nestled in the sought-after Gibson's Grant at Waters Edge community on Kent Island, this b...	4 beds \| 4 baths \| 2,185 sq.ft.	$780,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 2.28% Airbnb Rental Income: $3976 Traditional Rental Income: $3344 Airbnb ROI: 1.98% Traditional ROI: 2.28%

Real Estate investment in Chester, MD

There are 43 properties for sale in the city of Chester . The median list price in Chester is $442,235 and the average price per square foot is $221. In July 2026, the average monthly cash on cash return in Chester is 3.00%. The average monthly rental income in Chester is $2,880.

Chester, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 43 investment properties available for sale in Chester.

In 2026, the best neighborhood to buy investment property is CHESTER.

The ROI for Long-Term is higher than the Short-Term in Chester with average rental income of $2,880.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, MD

1012 AUCKLAND Way

CHESTER, MD

3 beds | 4 baths | 2,076 sq.ft.

$599,900

Airbnb cash on cash: 0.51%

Traditional cash on cash: 4.17%

Airbnb Rental Income: $2714

Traditional Rental Income: $4122

Airbnb ROI: 0.51%

Traditional ROI: 4.17%

34-E QUEEN ANNE Way

CHESTER, MD

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

$515,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 3.53%

Airbnb Rental Income: $2009

Traditional Rental Income: $3067

Airbnb ROI: 0.24%

Traditional ROI: 3.53%

115 GIBSON CIR

CHESTER, MD

2 beds | 3 baths | N/A

$575,000

Airbnb cash on cash: 0.84%

Traditional cash on cash: 2.79%

Airbnb Rental Income: $2009

Traditional Rental Income: $2534

Airbnb ROI: 0.84%

Traditional ROI: 2.79%

2008 BRIDGEPOINTE Drive

CHESTER, MD

2 beds | 2 baths | 1,804 sq.ft.

$380,000

Airbnb cash on cash: 1.5%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $2009

Traditional Rental Income: $2725

Airbnb ROI: 1.5%

Traditional ROI: 4.97%

5011 BRIDGEPOINTE Drive

CHESTER, MD

3 beds | 3 baths | 1,302 sq.ft.

$374,900

Airbnb cash on cash: 3.3%

Traditional cash on cash: 4.63%

Airbnb Rental Income: $2714

Traditional Rental Income: $2543

Airbnb ROI: 3.3%

Traditional ROI: 4.63%

1025 DUNDEE Court

CHESTER, MD

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

$324,900

Airbnb cash on cash: 4.02%

Traditional cash on cash: 5.77%

Airbnb Rental Income: $2714

Traditional Rental Income: $2606

Airbnb ROI: 4.02%

Traditional ROI: 5.77%

4000 HERONS NEST Way #22

CHESTER, MD

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

$530,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $2009

Traditional Rental Income: $3311

Airbnb ROI: -1.32%

Traditional ROI: 2.37%

106 BODYS NECK Road

CHESTER, MD

3 beds | 3 baths | 1,595 sq.ft.

$435,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $2714

Traditional Rental Income: $2829

Airbnb ROI: 1.47%