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
1363 Calvert Rd CHESTER, MD A MUST SEE home with complete rehab/remodel in 2017 with crown molding throughout, new ap...	3 beds \| 2 baths \| 1,400 sq.ft.	$469,999	Airbnb cash on cash: 9.66% Traditional cash on cash: 3.09% Airbnb Rental Income: $6279 Traditional Rental Income: $2152 Airbnb ROI: 9.66% Traditional ROI: 3.09%
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: 0.71% Airbnb Rental Income: $4662 Traditional Rental Income: $2646 Airbnb ROI: 2.74% Traditional ROI: 0.71%
402 Blenny Ln CHESTER, MD End-unit three-level townhome overlooking the pond in Bayside community. Freshly painted, ...	3 beds \| 3 baths \| 1,747 sq.ft.	$399,000	Airbnb cash on cash: 9.71% Traditional cash on cash: 5.93% Airbnb Rental Income: $6279 Traditional Rental Income: $3629 Airbnb ROI: 9.71% Traditional ROI: 5.93%
1401 Calvert Rd CHESTER, MD MARLING FARMS -Waterviews of Crab Alley Bay - PRICE REDUCED -Brick Rancher- All on ONE LEV...	2 beds \| 2 baths \| 1,444 sq.ft.	$454,900	Airbnb cash on cash: 6.77% Traditional cash on cash: 3.57% Airbnb Rental Income: $4662 Traditional Rental Income: $2336 Airbnb ROI: 6.77% Traditional ROI: 3.57%
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 \| 2 baths \| 2,602 sq.ft.	$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 #11 CHESTER, MD Luxury 55+ Living at Four Seasons on Kent Island - Move-In Ready & Priced to Sell! Welcome...	2 beds \| 2 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: 2.9% Airbnb Rental Income: $4662 Traditional Rental Income: $1858 Airbnb ROI: 9.87% Traditional ROI: 2.9%
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 #32 CHESTER, MD Move in this May and enjoy low-maintenance living in the sought-after 55+ community of Fou...	2 beds \| 2 baths \| 1,900 sq.ft.	$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%
154 HARRIER WAY CHESTER, MD * WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND* Price Reduced! Lowest pr...	2 beds \| 2 baths \| 1,900 sq.ft.	$639,450	Airbnb cash on cash: 3.73% Traditional cash on cash: 1.11% Airbnb Rental Income: $4662 Traditional Rental Income: $2132 Airbnb ROI: 3.73% Traditional ROI: 1.11%
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%
203 Riverside Dr CHESTER, MD To-be-built 5BR, 3.5BA waterfront home by Laine Street Homes - now under construction and ...	5 beds \| 3 baths \| 3,036 sq.ft.	$1,099,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.28% Airbnb Rental Income: $null Traditional Rental Income: $1588 Airbnb ROI: N/A Traditional ROI: 0.28%
205 Anchor Ln CHESTER, MD OPEN HOUSE, Saturday, 9/27, 11am -1pm...Price Improvement! Need more room? This expansive ...	6 beds \| 3 baths \| 3,500 sq.ft.	$535,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.14% Airbnb Rental Income: $null Traditional Rental Income: $4019 Airbnb ROI: N/A Traditional ROI: 6.14%
807 Auckland Way CHESTER, MD Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier ...	3 beds \| 3 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%
1906 Harbor Dr CHESTER, MD Great opportunity for a savvy investor to buy way below market value. This 3 brm 2 ba ranc...	3 beds \| 2 baths \| 1,750 sq.ft.	$499,900	Airbnb cash on cash: 9.03% Traditional cash on cash: 3.56% Airbnb Rental Income: $6279 Traditional Rental Income: $2487 Airbnb ROI: 9.03% Traditional ROI: 3.56%
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%
Harbor Dr CHESTER, MD New home being built! Act now and pick all your colors! Finished models can be seen! Call ...	3 beds \| 2 baths \| 1,250 sq.ft.	$499,900	Airbnb cash on cash: 9.28% Traditional cash on cash: 3.95% Airbnb Rental Income: $6279 Traditional Rental Income: $2554 Airbnb ROI: 9.28% Traditional ROI: 3.95%
112 Chessie Ct CHESTER, MD Step inside and see this meticulously cared for home! This home features a first floor pri...	3 beds \| 2 baths \| 2,066 sq.ft.	$519,900	Airbnb cash on cash: 8.32% Traditional cash on cash: 4.16% Airbnb Rental Income: $6279 Traditional Rental Income: $3022 Airbnb ROI: 8.32% Traditional ROI: 4.16%
1916 Stevens Dr CHESTER, MD Discover this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a ...	3 beds \| 2 baths \| 1,728 sq.ft.	$495,000	Airbnb cash on cash: 9.05% Traditional cash on cash: 4.38% Airbnb Rental Income: $6279 Traditional Rental Income: $2880 Airbnb ROI: 9.05% Traditional ROI: 4.38%
1704 Bayside Dr CHESTER, MD Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautif...	3 beds \| 2 baths \| 1,830 sq.ft.	$1,100,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 1.49% Airbnb Rental Income: $6279 Traditional Rental Income: $3259 Airbnb ROI: 3.24% Traditional ROI: 1.49%
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 \| 2 baths \| 1,280 sq.ft.	$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 #E CHESTER, MD Escape to the water - without the waterfront price. This Chester River-front townhome in Q...	2 beds \| 2 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: 0.49% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.71% Traditional ROI: 0.49%
259 Redstart Dr CHESTER, MD 259 Redstart Dr, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| 2,791 sq.ft.	$829,990	Airbnb cash on cash: 3.43% Traditional cash on cash: 0.97% Airbnb Rental Income: $5802 Traditional Rental Income: $2745 Airbnb ROI: 3.43% Traditional ROI: 0.97%
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%
109 John Gibson Dr CHESTER, MD 109 John Gibson Dr, CHESTER, MD 21619 \| Single Family Residential	6 beds \| 4 baths \| 4,165 sq.ft.	$915,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.09% Airbnb Rental Income: $null Traditional Rental Income: $3092 Airbnb ROI: N/A Traditional ROI: 1.09%
311 Kingfisher Ln CHESTER, MD 311 Kingfisher Ln, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$969,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.94% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: 0.94%
141 Redstart Dr CHESTER, MD 141 Redstart Dr, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,789 sq.ft.	$1,019,990	Airbnb cash on cash: 2.83% Traditional cash on cash: 0.28% Airbnb Rental Income: $6279 Traditional Rental Income: $2627 Airbnb ROI: 2.83% Traditional ROI: 0.28%
110 Kinglet Ct CHESTER, MD 110 Kinglet Ct, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$969,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.94% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: 0.94%
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%
1757 Harbor Dr CHESTER, MD 1757 Harbor Dr, CHESTER, MD 21619 \| Single Family Residential	4 beds \| 3 baths \| N/A	$1,167,890	Airbnb cash on cash: 2.1% Traditional cash on cash: 0.16% Airbnb Rental Income: $5802 Traditional Rental Income: $2541 Airbnb ROI: 2.1% Traditional ROI: 0.16%
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: 0.72% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 2.41% Traditional ROI: 0.72%
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%
111 Flycatcher Way CHESTER, MD 111 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$1,400,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.01% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: 0.01%
117 Flycatcher Way CHESTER, MD 117 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,930 sq.ft.	$1,400,000	Airbnb cash on cash: 1.5% Traditional cash on cash: -0.36% Airbnb Rental Income: $6279 Traditional Rental Income: $2627 Airbnb ROI: 1.5% Traditional ROI: -0.36%

Real Estate investment in Chester, MD

There are 64 properties for sale in the city of Chester . The median list price in Chester is $619,720 and the average price per square foot is $306. In January 2026, the average monthly cash on cash return in Chester is 1.00%. The average monthly rental income in Chester is $2,537.

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

There are 64 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 $4,662.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, MD

1363 Calvert Rd

CHESTER, MD

3 beds | 2 baths | 1,400 sq.ft.

$469,999

Airbnb cash on cash: 9.66%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $6279

Traditional Rental Income: $2152

Airbnb ROI: 9.66%

Traditional ROI: 3.09%

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: 0.71%

Airbnb Rental Income: $4662

Traditional Rental Income: $2646

Airbnb ROI: 2.74%

Traditional ROI: 0.71%

402 Blenny Ln

CHESTER, MD

3 beds | 3 baths | 1,747 sq.ft.

$399,000

Airbnb cash on cash: 9.71%

Traditional cash on cash: 5.93%

Airbnb Rental Income: $6279

Traditional Rental Income: $3629

Airbnb ROI: 9.71%

Traditional ROI: 5.93%

1401 Calvert Rd

CHESTER, MD

2 beds | 2 baths | 1,444 sq.ft.

$454,900

Airbnb cash on cash: 6.77%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $4662

Traditional Rental Income: $2336

Airbnb ROI: 6.77%

Traditional ROI: 3.57%

170 Harrier Way #34

CHESTER, MD

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

$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 #11

CHESTER, MD

2 beds | 2 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: 2.9%

Airbnb Rental Income: $4662

Traditional Rental Income: $1858

Airbnb ROI: 9.87%

Traditional ROI: 2.9%

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%