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
312 Blenny Ln CHESTER, MD You do not want to miss this opportunity to enjoy island living in this maintenance free, ...	3 beds \| 2 baths \| 1,899 sq.ft.	$479,000	Airbnb cash on cash: 7.96% Traditional cash on cash: 3.29% Airbnb Rental Income: $6279 Traditional Rental Income: $2950 Airbnb ROI: 7.96% Traditional ROI: 3.29%
3000 Herons Nest Way #11 CHESTER, MD Love Where You Live! Experience resort-style living that blends comfort, luxury, and conve...	2 beds \| 2 baths \| 2,003 sq.ft.	$539,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 1.06% Airbnb Rental Income: $4662 Traditional Rental Income: $2646 Airbnb ROI: 3.08% Traditional ROI: 1.06%
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%
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.	$669,900	Airbnb cash on cash: 5.04% Traditional cash on cash: 1.58% Airbnb Rental Income: $6279 Traditional Rental Income: $2881 Airbnb ROI: 5.04% Traditional ROI: 1.58%
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 \| 2 baths \| 2,003 sq.ft.	$494,900	Airbnb cash on cash: 3.32% Traditional cash on cash: 0.37% Airbnb Rental Income: $4662 Traditional Rental Income: $2331 Airbnb ROI: 3.32% Traditional ROI: 0.37%
1000 Herons Nest Way #32 CHESTER, MD Step into the good life in the sought-after Four Seasons on Kent Island, where low-mainten...	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%
4000 HERONS NEST Way unit: 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: 2.95% Traditional cash on cash: 1.76% Airbnb Rental Income: $4662 Traditional Rental Income: $3075 Airbnb ROI: 2.95% Traditional ROI: 1.76%
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%
1868 Roberta Dr CHESTER, MD This custom built home offers the perfect opportunity to live just minutes away from the C...	5 beds \| 3 baths \| 3,250 sq.ft.	$769,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.62% Airbnb Rental Income: $null Traditional Rental Income: $3937 Airbnb ROI: N/A Traditional ROI: 3.62%
111 Marshgrass Way #22 CHESTER, MD Rare resale condo, turnkey and only one year young! Your dream retreat awaits in this stun...	2 beds \| 2 baths \| 1,900 sq.ft.	$539,000	Airbnb cash on cash: 3.61% Traditional cash on cash: 1.75% Airbnb Rental Income: $4662 Traditional Rental Income: $2761 Airbnb ROI: 3.61% Traditional ROI: 1.75%
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.	$525,000	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.	$489,900	Airbnb cash on cash: 9.23% Traditional cash on cash: 3.65% Airbnb Rental Income: $6279 Traditional Rental Income: $2487 Airbnb ROI: 9.23% Traditional ROI: 3.65%
Harbor Dr CHESTER, MD New home being built! Act now and pick all your colors! Finished models can be seen! Call ...	N/A beds \| N/A baths \| 1,250 sq.ft.	$519,900	Airbnb cash on cash: 5.05% Traditional cash on cash: 3.76% Airbnb Rental Income: $4040 Traditional Rental Income: $2554 Airbnb ROI: 5.05% Traditional ROI: 3.76%
1916 Stevens Dr CHESTER, MD OPEN HOUSE - Sun. March 15 12:00 - 2:00. Come see this beautifully updated 3-bedroom, 2 fu...	3 beds \| 2 baths \| 1,728 sq.ft.	$489,000	Airbnb cash on cash: 9.18% Traditional cash on cash: 4.45% Airbnb Rental Income: $6279 Traditional Rental Income: $2880 Airbnb ROI: 9.18% Traditional ROI: 4.45%
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 OPEN HOUSE 2/21, 11:00 to 1:00... Nothing to do but move in! This roomy 2 bedroom, 2.5 ba...	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 PRICE DROP! Motivated Seller! Escape to the water - without the waterfront price. This Che...	2 beds \| 2 baths \| 1,680 sq.ft.	$465,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 4.01% Airbnb Rental Income: $4662 Traditional Rental Income: $3186 Airbnb ROI: 5.18% Traditional ROI: 4.01%
176 Flagstaff Way #33 CHESTER, MD 176 Flagstaff Way #33, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$829,990	Airbnb cash on cash: 2.58% Traditional cash on cash: 1.08% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 2.58% Traditional ROI: 1.08%
176 Flagstaff Way #43 CHESTER, MD 176 Flagstaff Way #43, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$979,990	Airbnb cash on cash: 1.87% Traditional cash on cash: 0.6% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.87% Traditional ROI: 0.6%
176 Flagstaff Way #2443 CHESTER, MD 176 Flagstaff Way #2443, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$979,900	Airbnb cash on cash: 1.09% Traditional cash on cash: -0.18% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.09% Traditional ROI: -0.18%
176 Flagstaff Way #2433 CHESTER, MD 176 Flagstaff Way #2433, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 1,900 sq.ft.	$799,990	Airbnb cash on cash: 1.66% Traditional cash on cash: 0.16% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 1.66% Traditional ROI: 0.16%
311 Kingfisher Ln CHESTER, MD 311 Kingfisher Ln, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$899,990	Airbnb cash on cash: N/A Traditional cash on cash: 0.97% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: 0.97%
110 Kinglet Ct CHESTER, MD 110 Kinglet Ct, CHESTER, MD 21619 \| Single Family Residential	5 beds \| 4 baths \| 3,225 sq.ft.	$899,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.14% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: 1.14%
176 Flagstaff Way #12 CHESTER, MD 176 Flagstaff Way #12, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$659,990	Airbnb cash on cash: 3.77% Traditional cash on cash: 1.97% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 3.77% Traditional ROI: 1.97%
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 #2412 CHESTER, MD 176 Flagstaff Way #2412, CHESTER, MD 21619 \| Condo/Coop	2 beds \| 2 baths \| 2,003 sq.ft.	$659,990	Airbnb cash on cash: 2.62% Traditional cash on cash: 0.82% Airbnb Rental Income: $4662 Traditional Rental Income: $2590 Airbnb ROI: 2.62% Traditional ROI: 0.82%
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: -0.03% Airbnb Rental Income: $null Traditional Rental Income: $3115 Airbnb ROI: N/A Traditional ROI: -0.03%
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: 1.45% Traditional cash on cash: -0.41% Airbnb Rental Income: $6279 Traditional Rental Income: $2627 Airbnb ROI: 1.45% Traditional ROI: -0.41%
123 Flycatcher Way CHESTER, MD 123 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,789 sq.ft.	$1,300,000	Airbnb cash on cash: 1.72% Traditional cash on cash: -0.28% Airbnb Rental Income: $6279 Traditional Rental Income: $2627 Airbnb ROI: 1.72% Traditional ROI: -0.28%
135 Nauset Ln CHESTER, MD 135 Nauset Ln, CHESTER, MD 21619 \| Single Family Residential	3 beds \| 3 baths \| 2,795 sq.ft.	$814,900	Airbnb cash on cash: 3.99% Traditional cash on cash: 0.76% Airbnb Rental Income: $6279 Traditional Rental Income: $2587 Airbnb ROI: 3.99% Traditional ROI: 0.76%
127 Flycatcher Way CHESTER, MD 127 Flycatcher Way, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 1,993 sq.ft.	$1,100,000	Airbnb cash on cash: 1.1% Traditional cash on cash: -0.44% Airbnb Rental Income: $4662 Traditional Rental Income: $2121 Airbnb ROI: 1.1% Traditional ROI: -0.44%
Tuscaloosa Plan CHESTER, MD	5 beds \| 4 baths \| 3,225 sq.ft.	$848,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $3088 Airbnb ROI: N/A Traditional ROI: 1.6%
Bernstein II Plan CHESTER, MD Bernstein II Plan, CHESTER, MD 21619 \| Single Family Residential	2 beds \| 2 baths \| 1,690 sq.ft.	$636,990	Airbnb cash on cash: 3.76% Traditional cash on cash: 0.77% Airbnb Rental Income: $4662 Traditional Rental Income: $1850 Airbnb ROI: 3.76% Traditional ROI: 0.77%
Taylor Plan CHESTER, MD	2 beds \| 2 baths \| 2,010 sq.ft.	$752,990	Airbnb cash on cash: 2.89% Traditional cash on cash: 0.36% Airbnb Rental Income: $4662 Traditional Rental Income: $1861 Airbnb ROI: 2.89% Traditional ROI: 0.36%
Chester Plan CHESTER, MD	2 beds \| 2 baths \| 1,900 sq.ft.	$499,990	Airbnb cash on cash: 5.62% Traditional cash on cash: 1.8% Airbnb Rental Income: $4662 Traditional Rental Income: $1908 Airbnb ROI: 5.62% Traditional ROI: 1.8%
Magothy Plan CHESTER, MD	2 beds \| 2 baths \| 2,003 sq.ft.	$499,990	Airbnb cash on cash: 5.62% Traditional cash on cash: 1.85% Airbnb Rental Income: $4662 Traditional Rental Income: $1931 Airbnb ROI: 5.62% Traditional ROI: 1.85%
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: 3.96% Traditional cash on cash: 1.48% Airbnb Rental Income: $4662 Traditional Rental Income: $2537 Airbnb ROI: 3.96% Traditional ROI: 1.48%
Severn Plan CHESTER, MD	3 beds \| 2 baths \| 2,602 sq.ft.	$584,990	Airbnb cash on cash: 6.98% Traditional cash on cash: 1.69% Airbnb Rental Income: $6279 Traditional Rental Income: $2155 Airbnb ROI: 6.98% Traditional ROI: 1.69%
Munich ESP Plan CHESTER, MD	4 beds \| 3 baths \| 3,601 sq.ft.	$883,990	Airbnb cash on cash: 3.3% Traditional cash on cash: 0.77% Airbnb Rental Income: $5802 Traditional Rental Income: $2507 Airbnb ROI: 3.3% Traditional ROI: 0.77%

Real Estate investment in Chester, MD

There are 67 properties for sale in the city of Chester . The median list price in Chester is $665,445 and the average price per square foot is $321. In March 2026, the average monthly cash on cash return in Chester is 1.00%. The average monthly rental income in Chester is $2,555.

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

There are 67 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

312 Blenny Ln

CHESTER, MD

3 beds | 2 baths | 1,899 sq.ft.

$479,000

Airbnb cash on cash: 7.96%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $6279

Traditional Rental Income: $2950

Airbnb ROI: 7.96%

Traditional ROI: 3.29%

3000 Herons Nest Way #11

CHESTER, MD

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

$539,000

Airbnb cash on cash: 3.08%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $4662

Traditional Rental Income: $2646

Airbnb ROI: 3.08%

Traditional ROI: 1.06%

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%

200 Harrier Way #21

CHESTER, MD

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

$669,900

Airbnb cash on cash: 5.04%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $6279

Traditional Rental Income: $2881

Airbnb ROI: 5.04%

Traditional ROI: 1.58%

1000 Herons Nest Way #23

CHESTER, MD

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

$494,900

Airbnb cash on cash: 3.32%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $4662

Traditional Rental Income: $2331

Airbnb ROI: 3.32%

Traditional ROI: 0.37%

1000 Herons Nest Way #32

CHESTER, MD

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%

4000 HERONS NEST Way unit: 22

CHESTER, MD

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

$560,000

Airbnb cash on cash: 2.95%

Traditional cash on cash: 1.76%

Airbnb Rental Income: $4662

Traditional Rental Income: $3075

Airbnb ROI: 2.95%

Traditional ROI: 1.76%

203 Riverside Dr

CHESTER, MD

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