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: 8.41% Traditional cash on cash: 4.37% Airbnb Rental Income: $5202 Traditional Rental Income: $2522 Airbnb ROI: 8.41% Traditional ROI: 4.37%
1004 AUCKLAND WAY CHESTER, MD Enjoy this stunning home for the weekend getaway or enjoy full time with views of WATER, W...	3 beds \| 4 baths \| 2,076 sq.ft.	$564,000	Airbnb cash on cash: 7.78% Traditional cash on cash: 3.98% Airbnb Rental Income: $6321 Traditional Rental Income: $3079 Airbnb ROI: 7.78% Traditional ROI: 3.98%
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	$289,900	Airbnb cash on cash: 6.84% Traditional cash on cash: 5.45% Airbnb Rental Income: $3143 Traditional Rental Income: $2050 Airbnb ROI: 6.84% Traditional ROI: 5.45%
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: 3.85% Traditional cash on cash: 2.37% Airbnb Rental Income: $5202 Traditional Rental Income: $3076 Airbnb ROI: 3.85% Traditional ROI: 2.37%
214 CLAIBORNE STREET CHESTER, MD Discover refined coastal living in this meticulously maintained contemporary home in the s...	3 beds \| 3 baths \| 1,852 sq.ft.	$599,000	Airbnb cash on cash: 6.77% Traditional cash on cash: 2.94% Airbnb Rental Income: $6321 Traditional Rental Income: $2938 Airbnb ROI: 6.77% Traditional ROI: 2.94%
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: 2.81% Traditional cash on cash: 1.88% Airbnb Rental Income: $5202 Traditional Rental Income: $3375 Airbnb ROI: 2.81% Traditional ROI: 1.88%
200 HARRIER WAY #42 CHESTER, MD Welcome to 200 Harrier Way. This gorgeous fourth floor, penthouse Chester model has scen...	2 beds \| 3 baths \| 1,900 sq.ft.	$674,500	Airbnb cash on cash: 1.62% Traditional cash on cash: 1.46% Airbnb Rental Income: $3143 Traditional Rental Income: $2331 Airbnb ROI: 1.62% Traditional ROI: 1.46%
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: 2% Traditional cash on cash: 3.15% Airbnb Rental Income: $3143 Traditional Rental Income: $3075 Airbnb ROI: 2% 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: 8.26% Traditional cash on cash: 5.4% Airbnb Rental Income: $6321 Traditional Rental Income: $3649 Airbnb ROI: 8.26% Traditional ROI: 5.4%
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: 6.05% Traditional cash on cash: 3.77% Airbnb Rental Income: $5202 Traditional Rental Income: $2935 Airbnb ROI: 6.05% 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%
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.	$479,900	Airbnb cash on cash: 9.58% Traditional cash on cash: 3.6% Airbnb Rental Income: $6321 Traditional Rental Income: $2393 Airbnb ROI: 9.58% Traditional ROI: 3.6%
105 BARREN RIDGE ROAD CHESTER, MD Kent Island-Introducing 105 Barren Ridge Rd., Chester. Meticulously maintained and recent...	4 beds \| 5 baths \| 3,016 sq.ft.	$649,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 6.51% Airbnb Rental Income: $5202 Traditional Rental Income: $5000 Airbnb ROI: 5.1% Traditional ROI: 6.51%
602 DOMINION ROAD CHESTER, MD INVESTOR ALERT!! Under Contract but accepting Back-Up Offers! Multi-unit home. First f...	2 beds \| 2 baths \| 1,800 sq.ft.	$250,000	Airbnb cash on cash: 7.91% Traditional cash on cash: 8.01% Airbnb Rental Income: $3143 Traditional Rental Income: $2454 Airbnb ROI: 7.91% Traditional ROI: 8.01%
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: 3.69% Traditional cash on cash: 2.24% Airbnb Rental Income: $5202 Traditional Rental Income: $3143 Airbnb ROI: 3.69% 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: 1.68% Traditional cash on cash: 1.09% Airbnb Rental Income: $5202 Traditional Rental Income: $3485 Airbnb ROI: 1.68% Traditional ROI: 1.09%
1602 CALVERT ROAD CHESTER, MD You don't want to miss this one - Waterview 4 bedroom 2 1/2 bath home in Marling Farms on...	4 beds \| 3 baths \| 2,184 sq.ft.	$611,550	Airbnb cash on cash: 5.47% Traditional cash on cash: 3.86% Airbnb Rental Income: $5202 Traditional Rental Income: $3226 Airbnb ROI: 5.47% Traditional ROI: 3.86%
135 BROADWATER DRIVE CHESTER, MD The Donegal model is a spacious and airy 2 bedroom, 2 bath home boasting an expansive open...	2 beds \| 2 baths \| 1,913 sq.ft.	$669,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.79% Airbnb Rental Income: $3143 Traditional Rental Income: $2600 Airbnb ROI: 1.52% Traditional ROI: 1.79%
166 WARBLER WAY #32 CHESTER, MD Rare condo resale in Four Seasons. Built in 2024 lived in only 6 months. This coastal in...	2 beds \| 3 baths \| N/A	$750,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 2.12% Airbnb Rental Income: $3143 Traditional Rental Income: $2789 Airbnb ROI: 1.61% Traditional ROI: 2.12%
502 DOMINION ROAD CHESTER, MD Charming Home with Endless Potential on Spacious .8-Acre Lot! Discover this unique opport...	4 beds \| 3 baths \| 2,682 sq.ft.	$425,000	Airbnb cash on cash: 8.28% Traditional cash on cash: 6.99% Airbnb Rental Income: $5202 Traditional Rental Income: $3632 Airbnb ROI: 8.28% Traditional ROI: 6.99%
170 HARRIER WAY #33 CHESTER, MD Welcome to 170 Harrier Way. This Chester model has scenic views of the Chester River, be...	2 beds \| 3 baths \| N/A	$645,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 2.43% Airbnb Rental Income: $3143 Traditional Rental Income: $2853 Airbnb ROI: 1.73% Traditional ROI: 2.43%

Real Estate investment in Chester, MD

There are 21 properties for sale in the city of Chester . The median list price in Chester is $599,000 and the average price per square foot is $285. In December 2024, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,935.

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

There are 21 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 $5,202.

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: 8.41%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $5202

Traditional Rental Income: $2522

Airbnb ROI: 8.41%

Traditional ROI: 4.37%

1004 AUCKLAND WAY

CHESTER, MD

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

$564,000

Airbnb cash on cash: 7.78%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $6321

Traditional Rental Income: $3079

Airbnb ROI: 7.78%

Traditional ROI: 3.98%

208 MERGANSER CT

CHESTER, MD

2 beds | 2 baths | N/A

$289,900

Airbnb cash on cash: 6.84%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $3143

Traditional Rental Income: $2050

Airbnb ROI: 6.84%

Traditional ROI: 5.45%

215 MCGUCKIN ST

CHESTER, MD

4 beds | 3 baths | N/A

$779,000

Airbnb cash on cash: 3.85%

Traditional cash on cash: 2.37%

Airbnb Rental Income: $5202

Traditional Rental Income: $3076

Airbnb ROI: 3.85%

Traditional ROI: 2.37%

214 CLAIBORNE STREET

CHESTER, MD

3 beds | 3 baths | 1,852 sq.ft.

$599,000

Airbnb cash on cash: 6.77%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $6321

Traditional Rental Income: $2938

Airbnb ROI: 6.77%

Traditional ROI: 2.94%

108 ELINOR STREET

CHESTER, MD

4 beds | 3 baths | 2,970 sq.ft.

$899,900

Airbnb cash on cash: 2.81%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $5202

Traditional Rental Income: $3375

Airbnb ROI: 2.81%

Traditional ROI: 1.88%

200 HARRIER WAY #42

CHESTER, MD

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

$674,500

Airbnb cash on cash: 1.62%

Traditional cash on cash: 1.46%

Airbnb Rental Income: $3143

Traditional Rental Income: $2331

Airbnb ROI: 1.62%

Traditional ROI: 1.46%

4000 HERONS NEST WAY #22

CHESTER, MD

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

$599,900

Airbnb cash on cash: 2%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $3143

Traditional Rental Income: $3075

Airbnb ROI: 2%