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
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 May16th from 10:00 - 12:00. Fully Remodeled Chester River Waterfront C...	2 beds \| 3 baths \| 1,586 sq.ft.	$549,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 3.25% Airbnb Rental Income: $1710 Traditional Rental Income: $3067 Airbnb ROI: -0.32% Traditional ROI: 3.25%
1906 STEVENS Drive CHESTER, MD Spacious and beautifully updated ranch-style home offering over 2,000 square feet of comfo...	3 beds \| 2 baths \| 2,016 sq.ft.	$464,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 4.12% Airbnb Rental Income: $2190 Traditional Rental Income: $2658 Airbnb ROI: 1.77% Traditional ROI: 4.12%
1025 DUNDEE Court CHESTER, MD OPEN House Sunday May 17, 9-11am! Welcome home to this Amazingly priced townhome on Kent I...	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: -1.75% Traditional cash on cash: 2.21% Airbnb Rental Income: $1710 Traditional Rental Income: $3311 Airbnb ROI: -1.75% Traditional ROI: 2.21%
190 HARRIER Way #21 CHESTER, MD Impeccably finished and immediately available, this corner residence provides the ease and...	3 beds \| 3 baths \| 2,639 sq.ft.	$649,900	Airbnb cash on cash: 0.68% Traditional cash on cash: 2.73% Airbnb Rental Income: $2190 Traditional Rental Income: $2881 Airbnb ROI: 0.68% Traditional ROI: 2.73%
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: 0.68% Traditional cash on cash: 2.73% Airbnb Rental Income: $2190 Traditional Rental Income: $2881 Airbnb ROI: 0.68% Traditional ROI: 2.73%
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: -1.99% Traditional cash on cash: 0.37% Airbnb Rental Income: $1710 Traditional Rental Income: $2331 Airbnb ROI: -1.99% Traditional ROI: 0.37%
134 MCHENNY Court CHESTER, MD Welcome home to this beautifully maintained three-bedroom, two-and-a-half-bath home in the...	3 beds \| 3 baths \| 1,839 sq.ft.	$599,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 2.6% Airbnb Rental Income: $2190 Traditional Rental Income: $2785 Airbnb ROI: 0.55% Traditional ROI: 2.6%
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.	$744,500	Airbnb cash on cash: -1.32% Traditional cash on cash: 3.77% Airbnb Rental Income: $713 Traditional Rental Income: $3937 Airbnb ROI: -1.32% Traditional ROI: 3.77%
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: 2.18% Traditional cash on cash: 4.01% Airbnb Rental Income: $2190 Traditional Rental Income: $2393 Airbnb ROI: 2.18% Traditional ROI: 4.01%
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: 0.36% Traditional cash on cash: 3.44% Airbnb Rental Income: $1710 Traditional Rental Income: $2761 Airbnb ROI: 0.36% Traditional ROI: 3.44%
1916 STEVENS Drive CHESTER, MD Now offered at a new and improved price, this beautifully updated and meticulously maintai...	3 beds \| 3 baths \| 1,728 sq.ft.	$475,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 4.61% Airbnb Rental Income: $2190 Traditional Rental Income: $2880 Airbnb ROI: 1.81% Traditional ROI: 4.61%
54-H QUEEN CAROLINE CT CHESTER, MD OPEN HOUSE, for the public, Sunday, May 17, 11:00 to 1:00! Owners have lowered the price ...	2 beds \| 3 baths \| N/A	$339,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 2.65% Airbnb Rental Income: $1710 Traditional Rental Income: $2064 Airbnb ROI: 0.05% Traditional ROI: 2.65%
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: 2.3% Traditional cash on cash: 3.02% Airbnb Rental Income: $1822 Traditional Rental Income: $1511 Airbnb ROI: 2.3% 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	$247,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 2.51% Airbnb Rental Income: $1822 Traditional Rental Income: $1309 Airbnb ROI: 2.59% Traditional ROI: 2.51%
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%
266 PEREGRINE Drive CHESTER, MD Huge Price Reduction on this beautiful, less than 1 year old home in the sought after comm...	4 beds \| 3 baths \| 2,870 sq.ft.	$712,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 3.18% Airbnb Rental Income: $3181 Traditional Rental Income: $3367 Airbnb ROI: 1.81% Traditional ROI: 3.18%
249 WARBLER Way CHESTER, MD $20,000 Price REDUCTION... make your move NOW! No waiting on the Builder for 8+ months!! T...	2 beds \| 2 baths \| 2,025 sq.ft.	$679,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.78% Airbnb Rental Income: $1710 Traditional Rental Income: $2730 Airbnb ROI: -0.58% Traditional ROI: 1.78%
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: 1.36% Traditional cash on cash: 2.4% Airbnb Rental Income: $1822 Traditional Rental Income: $1670 Airbnb ROI: 1.36% Traditional ROI: 2.4%
215 KINGFISHER Lane CHESTER, MD Price Reduced $50K - Open House Sunday May 3rd 1-3pm Please come see this beautiful home. ...	5 beds \| 5 baths \| 3,225 sq.ft.	$1,049,500	Airbnb cash on cash: -1.72% Traditional cash on cash: 2.76% Airbnb Rental Income: $713 Traditional Rental Income: $4779 Airbnb ROI: -1.72% Traditional ROI: 2.76%
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: -1.34% Traditional cash on cash: 1.26% Airbnb Rental Income: $1710 Traditional Rental Income: $3087 Airbnb ROI: -1.34% 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: -1.74% Traditional cash on cash: 2.58% Airbnb Rental Income: $1710 Traditional Rental Income: $3207 Airbnb ROI: -1.74% 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: -1.05% Traditional cash on cash: 1.68% Airbnb Rental Income: $1710 Traditional Rental Income: $3272 Airbnb ROI: -1.05% Traditional ROI: 1.68%
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 within this beautifully appoi...	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%
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.	$579,000	Airbnb cash on cash: 1% Traditional cash on cash: 3.05% Airbnb Rental Income: $2190 Traditional Rental Income: $2748 Airbnb ROI: 1% Traditional ROI: 3.05%
1719 HARBOR Drive CHESTER, MD Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed fo...	3 beds \| 5 baths \| 4,208 sq.ft.	$1,495,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 2.21% Airbnb Rental Income: $2190 Traditional Rental Income: $5405 Airbnb ROI: -0.5% Traditional ROI: 2.21%
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	$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%
45-G QUEEN NEVA Court CHESTER, MD This charming townhouse in Queens Landing offers a perfect blend of comfort and community ...	2 beds \| 3 baths \| 1,312 sq.ft.	$349,500	Airbnb cash on cash: 1.96% Traditional cash on cash: 5.29% Airbnb Rental Income: $1710 Traditional Rental Income: $2329 Airbnb ROI: 1.96% Traditional ROI: 5.29%
2832 COX NECK Road CHESTER, MD Sited on Cox Creek with 369 feet of waterfront, this elegant contemporary residence offers...	4 beds \| 5 baths \| 4,717 sq.ft.	$2,450,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 0.96% Airbnb Rental Income: $3181 Traditional Rental Income: $6047 Airbnb ROI: -0.61% Traditional ROI: 0.96%
6005 BRIDGEPOINTE Drive CHESTER, MD	3 beds \| 3 baths \| 1,302 sq.ft.	$362,900	Airbnb cash on cash: 2.81% Traditional cash on cash: 5.36% Airbnb Rental Income: $2190 Traditional Rental Income: $2502 Airbnb ROI: 2.81% Traditional ROI: 5.36%

Real Estate investment in Chester, MD

There are 33 properties for sale in the city of Chester . The median list price in Chester is $494,900 and the average price per square foot is $257. In May 2026, the average monthly cash on cash return in Chester is 3.00%. The average monthly rental income in Chester is $2,881.

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

There are 33 investment properties available for sale in Chester.

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

The ROI for Short-Term is higher than the Long-Term in Chester with average rental income of $2,190.

Your search for investment property begins and ends here

Investment Property 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: -0.32%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $1710

Traditional Rental Income: $3067

Airbnb ROI: -0.32%

Traditional ROI: 3.25%

1906 STEVENS Drive

CHESTER, MD

3 beds | 2 baths | 2,016 sq.ft.

$464,000

Airbnb cash on cash: 1.77%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $2190

Traditional Rental Income: $2658

Airbnb ROI: 1.77%

Traditional ROI: 4.12%

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: -1.75%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $1710

Traditional Rental Income: $3311

Airbnb ROI: -1.75%

Traditional ROI: 2.21%

190 HARRIER Way #21

CHESTER, MD

3 beds | 3 baths | 2,639 sq.ft.

$649,900

Airbnb cash on cash: 0.68%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $2190

Traditional Rental Income: $2881

Airbnb ROI: 0.68%

Traditional ROI: 2.73%

190 HARRIER Way #24

CHESTER, MD

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

$650,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $2190

Traditional Rental Income: $2881

Airbnb ROI: 0.68%

Traditional ROI: 2.73%

1000 HERONS NEST WAY #23

CHESTER, MD

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

$494,900

Airbnb cash on cash: -1.99%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $1710

Traditional Rental Income: $2331

Airbnb ROI: -1.99%