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
34-E QUEEN ANNE Way CHESTER, MD Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water...	2 beds \| 3 baths \| 1,104 sq.ft.	$469,000	Airbnb cash on cash: 6% Traditional cash on cash: 4.56% Airbnb Rental Income: $4662 Traditional Rental Income: $3067 Airbnb ROI: 6% Traditional ROI: 4.56%
312 BLENNY Lane CHESTER, MD You do not want to miss this opportunity to enjoy island living in this maintenance free, ...	3 beds \| 4 baths \| 1,899 sq.ft.	$479,000	Airbnb cash on cash: 9.44% Traditional cash on cash: 4.77% Airbnb Rental Income: $6279 Traditional Rental Income: $2950 Airbnb ROI: 9.44% Traditional ROI: 4.77%
1401 CALVERT Road CHESTER, MD Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - PRICE REDUCED...	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%
141 SWITCHGRASS Way unit: 34 #34 CHESTER, MD ** NICE VIEWS OF THE CHESTER RIVER * LOWEST PRICED SEVERN MODEL** K Hovnanian'...	3 beds \| 3 baths \| 2,600 sq.ft.	$684,950	Airbnb cash on cash: 5.57% Traditional cash on cash: 2.44% Airbnb Rental Income: $6279 Traditional Rental Income: $3044 Airbnb ROI: 5.57% Traditional ROI: 2.44%
170 HARRIER WAY #34 CHESTER, MD Recently reduced by $55,000 to $740,000 with immediate availability. This is one of only t...	3 beds \| 3 baths \| N/A	$740,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 2.47% Airbnb Rental Income: $6279 Traditional Rental Income: $2981 Airbnb ROI: 5.46% Traditional ROI: 2.47%
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: 4.83% Traditional cash on cash: 2.17% Airbnb Rental Income: $4662 Traditional Rental Income: $2354 Airbnb ROI: 4.83% Traditional ROI: 2.17%
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: 5.26% Traditional cash on cash: 2.75% Airbnb Rental Income: $4662 Traditional Rental Income: $2521 Airbnb ROI: 5.26% Traditional ROI: 2.75%
154 HARRIER WAY CHESTER, MD * WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND* Price Reduced! Better th...	2 beds \| 2 baths \| 1,900 sq.ft.	$639,500	Airbnb cash on cash: 3.75% Traditional cash on cash: 1.13% Airbnb Rental Income: $4662 Traditional Rental Income: $2132 Airbnb ROI: 3.75% Traditional ROI: 1.13%
203 RIVERSIDE DR CHESTER, MD To-be-built 5BR, 3.5BA waterfront home by Laine Street Homes - now under construction and ...	5 beds \| 4 baths \| N/A	$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%
1340 QUEEN ANNE Drive CHESTER, MD Discover the charm of this fully updated ranch in a serene, water-privileged community! Wi...	3 beds \| 2 baths \| 1,248 sq.ft.	$459,900	Airbnb cash on cash: 9.95% Traditional cash on cash: 3.8% Airbnb Rental Income: $6279 Traditional Rental Income: $2393 Airbnb ROI: 9.95% Traditional ROI: 3.8%
132 CLAIBORNE Street CHESTER, MD Discover exceptional living on an oversized fenced lot in the sought-after community of Gi...	3 beds \| 4 baths \| 2,400 sq.ft.	$659,000	Airbnb cash on cash: 5.66% Traditional cash on cash: 2.63% Airbnb Rental Income: $6279 Traditional Rental Income: $3180 Airbnb ROI: 5.66% Traditional ROI: 2.63%
1000 HERONS NEST Way unit: 22 #22 CHESTER, MD Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum C...	2 beds \| 3 baths \| 1,900 sq.ft.	$488,000	Airbnb cash on cash: 5.44% Traditional cash on cash: 4.47% Airbnb Rental Income: $4662 Traditional Rental Income: $3249 Airbnb ROI: 5.44% Traditional ROI: 4.47%
224 BAYBERRY Drive CHESTER, MD Welcome to Easy Living on the Eastern Shore! *** Discover the perfect blend of comfort, st...	2 beds \| 2 baths \| 1,913 sq.ft.	$599,900	Airbnb cash on cash: 4.64% Traditional cash on cash: 2.78% Airbnb Rental Income: $4662 Traditional Rental Income: $2652 Airbnb ROI: 4.64% Traditional ROI: 2.78%
30-C QUEEN MARY Court CHESTER, MD OPEN HOUSE SUN 12/7 11a-1p! Settlement possible for the Holidays & New Year! Enjoy low-mai...	2 beds \| 3 baths \| 1,440 sq.ft.	$339,900	Airbnb cash on cash: 9.59% Traditional cash on cash: 5.9% Airbnb Rental Income: $4662 Traditional Rental Income: $2518 Airbnb ROI: 9.59% Traditional ROI: 5.9%
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%
202 MCHENNY Court CHESTER, MD Beautiful Home in Gibson's Grant with Elevator, Open Floor Plan & Two-Car Garage Welcome t...	3 beds \| 3 baths \| 2,520 sq.ft.	$825,000	Airbnb cash on cash: 4.74% Traditional cash on cash: 2.23% Airbnb Rental Income: $6279 Traditional Rental Income: $3114 Airbnb ROI: 4.74% Traditional ROI: 2.23%
162 KIRWANS LANDING Lane CHESTER, MD BIG PRICE IMPROVEMENT. Private Waterfront Living in Kirwans Landing!Nestled on 1.4 acres i...	4 beds \| 3 baths \| 2,404 sq.ft.	$869,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 3.1% Airbnb Rental Income: $5802 Traditional Rental Income: $3870 Airbnb ROI: 4.06% Traditional ROI: 3.1%
HARBOR Drive 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: 9.29% Traditional cash on cash: 3.96% Airbnb Rental Income: $6279 Traditional Rental Income: $2554 Airbnb ROI: 9.29% Traditional ROI: 3.96%
112 CHESSIE Court CHESTER, MD Step inside and see this meticulously cared for home! This home features a first floor pri...	3 beds \| 3 baths \| 2,066 sq.ft.	$519,900	Airbnb cash on cash: 8.45% Traditional cash on cash: 4.29% Airbnb Rental Income: $6279 Traditional Rental Income: $3022 Airbnb ROI: 8.45% Traditional ROI: 4.29%
1916 STEVENS Drive 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: 9.06% Traditional cash on cash: 4.39% Airbnb Rental Income: $6279 Traditional Rental Income: $2880 Airbnb ROI: 9.06% Traditional ROI: 4.39%
1704 BAYSIDE Drive CHESTER, MD Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautif...	3 beds \| 3 baths \| 1,830 sq.ft.	$1,100,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 1.5% Airbnb Rental Income: $6279 Traditional Rental Income: $3259 Airbnb ROI: 3.25% Traditional ROI: 1.5%
10-B QUEEN ELIZABETH CT CHESTER, MD WATERFRONT !!! Spectacular sunrise views on display over the Chester River from this cozy ...	1 beds \| 1 baths \| 1,620 sq.ft.	$330,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 2.81% Airbnb Rental Income: $3572 Traditional Rental Income: $1430 Airbnb ROI: 7.19% Traditional ROI: 2.81%

Real Estate investment in Chester, MD

There are 23 properties for sale in the city of Chester . The median list price in Chester is $497,000 and the average price per square foot is $275. In December 2025, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,871.

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

There are 23 investment properties available for sale in Chester.

In 2025, 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 $5,802.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, MD

34-E QUEEN ANNE Way

CHESTER, MD

2 beds | 3 baths | 1,104 sq.ft.

$469,000

Airbnb cash on cash: 6%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $4662

Traditional Rental Income: $3067

Airbnb ROI: 6%

Traditional ROI: 4.56%

312 BLENNY Lane

CHESTER, MD

3 beds | 4 baths | 1,899 sq.ft.

$479,000

Airbnb cash on cash: 9.44%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $6279

Traditional Rental Income: $2950

Airbnb ROI: 9.44%

Traditional ROI: 4.77%

1401 CALVERT Road

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%

141 SWITCHGRASS Way unit: 34 #34

CHESTER, MD

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

$684,950

Airbnb cash on cash: 5.57%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $6279

Traditional Rental Income: $3044

Airbnb ROI: 5.57%

Traditional ROI: 2.44%

170 HARRIER WAY #34

CHESTER, MD

3 beds | 3 baths | N/A

$740,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $6279

Traditional Rental Income: $2981

Airbnb ROI: 5.46%

Traditional ROI: 2.47%

190 HARRIER Way unit: 11 #11

CHESTER, MD

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

$540,000

Airbnb cash on cash: 4.83%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $4662

Traditional Rental Income: $2354

Airbnb ROI: 4.83%

Traditional ROI: 2.17%

1000 HERONS NEST Way unit: 32 #32

CHESTER, MD

2 beds | 2 baths | N/A

$499,000

Airbnb cash on cash: 5.26%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $4662

Traditional Rental Income: $2521

Airbnb ROI: 5.26%

Traditional ROI: 2.75%

154 HARRIER WAY

CHESTER, MD

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

$639,500

Airbnb cash on cash: 3.75%

Traditional cash on cash: 1.13%

Airbnb Rental Income: $4662

Traditional Rental Income: $2132

Airbnb ROI: 3.75%