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
1926 SHERMAN DRIVE CHESTER, MD Photo's on the way !! Welcome to Kent Island. This 4 Bedroom 2 Bath property is move in re...	4 beds \| 2 baths \| 1,560 sq.ft.	$429,900	Airbnb cash on cash: 5.06% Traditional cash on cash: 4.56% Airbnb Rental Income: $3496 Traditional Rental Income: $2522 Airbnb ROI: 5.06% Traditional ROI: 4.56%
1004 AUCKLAND WAY CHESTER, MD WOW! MASSIVE PRICE REDUCTION WATER, WATER EVERYWHERE! Waterfront without the worry! En...	3 beds \| 4 baths \| 2,076 sq.ft.	$564,000	Airbnb cash on cash: 8.42% Traditional cash on cash: 4.01% Airbnb Rental Income: $6709 Traditional Rental Income: $3079 Airbnb ROI: 8.42% Traditional ROI: 4.01%
208 MERGANSER CT CHESTER, MD GREAT OPPORTUNITY to own this first-floor end unit. Which does not often come on the mark...	2 beds \| 2 baths \| N/A	$299,900	Airbnb cash on cash: 9.17% Traditional cash on cash: 5.24% Airbnb Rental Income: $4018 Traditional Rental Income: $2050 Airbnb ROI: 9.17% Traditional ROI: 5.24%
215 MCGUCKIN ST CHESTER, MD PLEASE CLICK ON VIRTUAL TOUR ICON TO VIEW INTERACTIVE FLOOR PLAN**Welcome to 215 McGuckin!...	4 beds \| 3 baths \| N/A	$779,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 2.37% Airbnb Rental Income: $3496 Traditional Rental Income: $3076 Airbnb ROI: 1.89% Traditional ROI: 2.37%
206 PRICES LANE CHESTER, MD Experience the charm and tranquility of country living with this incredibly affordable 4-b...	4 beds \| 2 baths \| 1,782 sq.ft.	$330,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 6.41% Airbnb Rental Income: $3496 Traditional Rental Income: $2554 Airbnb ROI: 6.96% Traditional ROI: 6.41%
104 SUNSET DRIVE CHESTER, MD Dreaming of a home with all the upgrades? This property has it all, including a deeded boa...	4 beds \| 3 baths \| 2,096 sq.ft.	$629,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 3.96% Airbnb Rental Income: $3496 Traditional Rental Income: $3462 Airbnb ROI: 2.7% Traditional ROI: 3.96%
1830 SHERMAN DRIVE CHESTER, MD The expanded ranch you have been waiting for just hit the market. Located in friendly, wat...	4 beds \| 3 baths \| 2,176 sq.ft.	$390,000	Airbnb cash on cash: 5.39% Traditional cash on cash: 6.07% Airbnb Rental Income: $3496 Traditional Rental Income: $2975 Airbnb ROI: 5.39% Traditional ROI: 6.07%
141 SWITCHGRASS WAY #34 CHESTER, MD K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesape...	3 beds \| 3 baths \| 2,600 sq.ft.	$679,500	Airbnb cash on cash: 6.22% Traditional cash on cash: 2.5% Airbnb Rental Income: $6709 Traditional Rental Income: $3044 Airbnb ROI: 6.22% Traditional ROI: 2.5%
108 ELINOR STREET CHESTER, MD Welcome home to this immaculately maintained home in the coveted Gibsonâs Grant communit...	4 beds \| 3 baths \| 2,970 sq.ft.	$899,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 1.88% Airbnb Rental Income: $3496 Traditional Rental Income: $3375 Airbnb ROI: 1.11% Traditional ROI: 1.88%
200 HARRIER WAY #31 CHESTER, MD Luxury Resort Style Living!! Four Seasons at Kent Island is an active 55+ community. When...	3 beds \| 3 baths \| N/A	$689,900	Airbnb cash on cash: 6.48% Traditional cash on cash: 2.26% Airbnb Rental Income: $6709 Traditional Rental Income: $2686 Airbnb ROI: 6.48% Traditional ROI: 2.26%
4000 HERONS NEST WAY #22 CHESTER, MD New Listing! Four Seasons @ Kent Island - 55+ Community - Turn Key & Lovely 2nd Floor Con...	2 beds \| 3 baths \| 1,900 sq.ft.	$599,900	Airbnb cash on cash: 3.3% Traditional cash on cash: 3.15% Airbnb Rental Income: $4018 Traditional Rental Income: $3075 Airbnb ROI: 3.3% Traditional ROI: 3.15%
703 BLENNY LANE CHESTER, MD This beautiful Bayside boasts an open floor plan with gorgeous views. Not ready to buy? R...	3 beds \| 4 baths \| 2,172 sq.ft.	$534,900	Airbnb cash on cash: 8.9% Traditional cash on cash: 5.4% Airbnb Rental Income: $6709 Traditional Rental Income: $3649 Airbnb ROI: 8.9% Traditional ROI: 5.4%
300 DRAKE TAIL PL CHESTER, MD Just reduced $10000 on 10/9/24 Well- Maintained END UNIT CHESTER RIVER TOWNHOME in AMENITY...	2 beds \| 3 baths \| N/A	$305,000	Airbnb cash on cash: 8.9% Traditional cash on cash: 6.83% Airbnb Rental Income: $4018 Traditional Rental Income: $2566 Airbnb ROI: 8.9% Traditional ROI: 6.83%
307 SCHOONER WAY #42 CHESTER, MD Nestled in the heart of the Bayside Community overlooking the pond, this immaculate 2 ( po...	2 beds \| 3 baths \| 1,747 sq.ft.	$364,900	Airbnb cash on cash: 5.37% Traditional cash on cash: 4.22% Airbnb Rental Income: $4018 Traditional Rental Income: $2766 Airbnb ROI: 5.37% Traditional ROI: 4.22%
1501 SAINT MARYS ROAD CHESTER, MD This recently updated colonial is turn key ready for the new owners and sits on a corner l...	4 beds \| 3 baths \| 1,612 sq.ft.	$569,077	Airbnb cash on cash: 3.38% Traditional cash on cash: 3.77% Airbnb Rental Income: $3496 Traditional Rental Income: $2935 Airbnb ROI: 3.38% Traditional ROI: 3.77%
116 KIRWANS LANDING LANE CHESTER, MD This quality built cape has had one owner it's whole life and they have taken care of it w...	5 beds \| 5 baths \| 3,736 sq.ft.	$1,350,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.45% Airbnb Rental Income: $null Traditional Rental Income: $5171 Airbnb ROI: N/A Traditional ROI: 2.45%
15 QUEEN ANNE WAY #E CHESTER, MD If youâre a water enthusiast, this stunning 2.5-level townhome offers the perfect blend ...	2 beds \| 3 baths \| 1,680 sq.ft.	$559,750	Airbnb cash on cash: 4.28% Traditional cash on cash: 3.97% Airbnb Rental Income: $4018 Traditional Rental Income: $2997 Airbnb ROI: 4.28% Traditional ROI: 3.97%
2865 COX NECK RD CHESTER, MD The main level of this custom 4 BR, 3.5BA waterfront residence on 1.9 acres boasts multipl...	4 beds \| 4 baths \| N/A	$2,398,900	Airbnb cash on cash: -0.54% Traditional cash on cash: -0.07% Airbnb Rental Income: $3496 Traditional Rental Income: $3777 Airbnb ROI: -0.54% Traditional ROI: -0.07%
4000 HERONS NEST WAY #44 CHESTER, MD ** SPACIOUS PENTHOUSE CONDO. LOVELY VIEWS OF MACUM CREEK** The Severn model is a s...	3 beds \| 3 baths \| 2,602 sq.ft.	$689,500	Airbnb cash on cash: 6.14% Traditional cash on cash: 2.47% Airbnb Rental Income: $6709 Traditional Rental Income: $3044 Airbnb ROI: 6.14% Traditional ROI: 2.47%
208 WINCHESTER STREET CHESTER, MD Stunning contemporary coastal home in sought-after Gibsons Grant with views of the Chester...	4 beds \| 5 baths \| 3,888 sq.ft.	$1,415,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 1.56% Airbnb Rental Income: $3496 Traditional Rental Income: $4622 Airbnb ROI: 0.12% Traditional ROI: 1.56%
209 HARRIER WAY CHESTER, MD This brand new, custom-built home offers 2791 square feet of luxurious living space, with ...	4 beds \| 3 baths \| 2,791 sq.ft.	$740,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.24% Airbnb Rental Income: $3496 Traditional Rental Income: $3143 Airbnb ROI: 1.63% Traditional ROI: 2.24%
104 CHESTER WAY CHESTER, MD Welcome home to this stunning waterfront home located at the Waters Edge in Gibsonâs Gra...	4 beds \| 3 baths \| 2,904 sq.ft.	$1,215,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 1.09% Airbnb Rental Income: $3496 Traditional Rental Income: $3485 Airbnb ROI: 0.42% Traditional ROI: 1.09%

Real Estate investment in Chester, MD

There are 22 properties for sale in the city of Chester . The median list price in Chester is $569,077 and the average price per square foot is $257. In November 2024, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $3,044.

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

There are 22 investment properties available for sale in Chester.

In 2024, 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 $4,018.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, MD

1926 SHERMAN DRIVE

CHESTER, MD

4 beds | 2 baths | 1,560 sq.ft.

$429,900

Airbnb cash on cash: 5.06%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $3496

Traditional Rental Income: $2522

Airbnb ROI: 5.06%

Traditional ROI: 4.56%

1004 AUCKLAND WAY

CHESTER, MD

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

$564,000

Airbnb cash on cash: 8.42%

Traditional cash on cash: 4.01%

Airbnb Rental Income: $6709

Traditional Rental Income: $3079

Airbnb ROI: 8.42%

Traditional ROI: 4.01%

208 MERGANSER CT

CHESTER, MD

2 beds | 2 baths | N/A

$299,900

Airbnb cash on cash: 9.17%

Traditional cash on cash: 5.24%

Airbnb Rental Income: $4018

Traditional Rental Income: $2050

Airbnb ROI: 9.17%

Traditional ROI: 5.24%

215 MCGUCKIN ST

CHESTER, MD

4 beds | 3 baths | N/A

$779,000

Airbnb cash on cash: 1.89%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $3496

Traditional Rental Income: $3076

Airbnb ROI: 1.89%

Traditional ROI: 2.37%

206 PRICES LANE

CHESTER, MD

4 beds | 2 baths | 1,782 sq.ft.

$330,000

Airbnb cash on cash: 6.96%

Traditional cash on cash: 6.41%

Airbnb Rental Income: $3496

Traditional Rental Income: $2554

Airbnb ROI: 6.96%

Traditional ROI: 6.41%

104 SUNSET DRIVE

CHESTER, MD

4 beds | 3 baths | 2,096 sq.ft.

$629,000

Airbnb cash on cash: 2.7%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $3496

Traditional Rental Income: $3462

Airbnb ROI: 2.7%

Traditional ROI: 3.96%

1830 SHERMAN DRIVE

CHESTER, MD

4 beds | 3 baths | 2,176 sq.ft.

$390,000

Airbnb cash on cash: 5.39%

Traditional cash on cash: 6.07%

Airbnb Rental Income: $3496

Traditional Rental Income: $2975

Airbnb ROI: 5.39%

Traditional ROI: 6.07%

141 SWITCHGRASS WAY #34

CHESTER, MD

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

$679,500

Airbnb cash on cash: 6.22%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $6709

Traditional Rental Income: $3044

Airbnb ROI: 6.22%