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.

Single Family Homes for Sale in Chester, MD

Search for Single Family Residential for Sale in Chester, Maryland. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 15 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
444 MACUM CREEK DR CHESTER, MD Welcome to 444 Macum Creek DriveEnjoy the Water Views from the Main Level Porch, Upper...	3 beds \| 3 baths \| N/A	$850,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 1.68% Airbnb Rental Income: $6279 Traditional Rental Income: $2751 Airbnb ROI: 4.58% Traditional ROI: 1.68%
203 BARREN RIDGE ROAD CHESTER, MD Priced to Sell- VERY motivated sellers!!! Nestled in the tranquil community of Chester, Ma...	3 beds \| 2 baths \| 2,072 sq.ft.	$475,000	Airbnb cash on cash: 9.36% Traditional cash on cash: 3.97% Airbnb Rental Income: $6279 Traditional Rental Income: $2647 Airbnb ROI: 9.36% Traditional ROI: 3.97%
1401 CALVERT ROAD CHESTER, MD Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - All on one le...	2 beds \| 2 baths \| 1,444 sq.ft.	$485,000	Airbnb cash on cash: 6.29% Traditional cash on cash: 3.29% Airbnb Rental Income: $4662 Traditional Rental Income: $2336 Airbnb ROI: 6.29% Traditional ROI: 3.29%
154 HARRIER WAY CHESTER, MD * WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND* The Donegal model is a s...	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%
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.	$469,900	Airbnb cash on cash: 9.72% Traditional cash on cash: 3.7% Airbnb Rental Income: $6279 Traditional Rental Income: $2393 Airbnb ROI: 9.72% Traditional ROI: 3.7%
114 ADDISON COURT CHESTER, MD REDUCED "Shiny and new" might be the best way to describe the feel of this lovely 3 ...	3 beds \| 3 baths \| 2,342 sq.ft.	$575,000	Airbnb cash on cash: 7.44% Traditional cash on cash: 3.84% Airbnb Rental Income: $6279 Traditional Rental Income: $3111 Airbnb ROI: 7.44% Traditional ROI: 3.84%
132 CLAIBORNE STREET CHESTER, MD Sitting pretty on one of the largest, level lots in the prestigious Gibson's Grant Communi...	3 beds \| 4 baths \| 2,400 sq.ft.	$725,000	Airbnb cash on cash: 5.1% Traditional cash on cash: 2.35% Airbnb Rental Income: $6279 Traditional Rental Income: $3180 Airbnb ROI: 5.1% Traditional ROI: 2.35%
307 SKIPPER LANE CHESTER, MD Welcome to Your Refreshing New Home with First-Floor Living! This beautifully updated resi...	3 beds \| 2 baths \| 2,180 sq.ft.	$525,000	Airbnb cash on cash: 8.46% Traditional cash on cash: 3.46% Airbnb Rental Income: $6279 Traditional Rental Income: $2587 Airbnb ROI: 8.46% Traditional ROI: 3.46%
205 ANCHOR LANE CHESTER, MD Price Improvement! Need more room? This expansive home is ready to welcome your whole fami...	5 beds \| 3 baths \| 3,500 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.94% Airbnb Rental Income: $null Traditional Rental Income: $4019 Airbnb ROI: N/A Traditional ROI: 5.94%
1872 HARBOR DRIVE CHESTER, MD Harbor View Community \| Corner Lot \| Renovated Rancher with Room to Grow Welcome to 1872 H...	3 beds \| 2 baths \| 1,486 sq.ft.	$495,000	Airbnb cash on cash: 9.14% Traditional cash on cash: 3.9% Airbnb Rental Income: $6279 Traditional Rental Income: $2614 Airbnb ROI: 9.14% Traditional ROI: 3.9%
2723 COX NECK RD CHESTER, MD Harbor View - 100% Financing is Available!!!This newly constructed home features 4 bedroom...	4 beds \| 3 baths \| N/A	$473,900	Airbnb cash on cash: 8.98% Traditional cash on cash: 4.97% Airbnb Rental Income: $5802 Traditional Rental Income: $2870 Airbnb ROI: 8.98% Traditional ROI: 4.97%
224 BAYBERRY DRIVE CHESTER, MD Welcome to Easy Living on the Eastern Shore! *** Discover the perfect blend of comfort, s...	2 beds \| 2 baths \| 1,913 sq.ft.	$624,900	Airbnb cash on cash: 4.42% Traditional cash on cash: 2.63% Airbnb Rental Income: $4662 Traditional Rental Income: $2652 Airbnb ROI: 4.42% Traditional ROI: 2.63%
315 CROSS CREEK CT CHESTER, MD You are going to love this bright and spacious home providing almost 2400 feet of living s...	4 beds \| 3 baths \| N/A	$585,000	Airbnb cash on cash: 6.66% Traditional cash on cash: 4.03% Airbnb Rental Income: $5802 Traditional Rental Income: $3208 Airbnb ROI: 6.66% Traditional ROI: 4.03%
104 WOODS ROAD CHESTER, MD PERFECT MULTI GENERATIONAL HOME!!!! LIST PRICE ADJUSTED !!FANTASTIC HOME! THE COMPLETE PAC...	5 beds \| 4 baths \| 3,065 sq.ft.	$800,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.82% Airbnb Rental Income: $null Traditional Rental Income: $4174 Airbnb ROI: N/A Traditional ROI: 3.82%
124 NAUSET LANE CHESTER, MD NEW UPDATED PHOTOS!! Take another look! Turnkey Luxury with Over $175K in Upgrades Four Se...	3 beds \| 3 baths \| 2,583 sq.ft.	$847,500	Airbnb cash on cash: 4.17% Traditional cash on cash: 1.74% Airbnb Rental Income: $6279 Traditional Rental Income: $3129 Airbnb ROI: 4.17% Traditional ROI: 1.74%

Your search for investment property begins and ends here

Single Family Homes for Sale in Chester, MD

444 MACUM CREEK DR

CHESTER, MD

3 beds | 3 baths | N/A

$850,000

Airbnb cash on cash: 4.58%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $6279

Traditional Rental Income: $2751

Airbnb ROI: 4.58%

Traditional ROI: 1.68%

203 BARREN RIDGE ROAD

CHESTER, MD

3 beds | 2 baths | 2,072 sq.ft.

$475,000

Airbnb cash on cash: 9.36%

Traditional cash on cash: 3.97%

Airbnb Rental Income: $6279

Traditional Rental Income: $2647

Airbnb ROI: 9.36%

Traditional ROI: 3.97%

1401 CALVERT ROAD

CHESTER, MD

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

$485,000

Airbnb cash on cash: 6.29%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $4662

Traditional Rental Income: $2336

Airbnb ROI: 6.29%

Traditional ROI: 3.29%

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%

Traditional ROI: 1.13%

1340 QUEEN ANNE DRIVE

CHESTER, MD

3 beds | 2 baths | 1,248 sq.ft.

$469,900

Airbnb cash on cash: 9.72%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $6279

Traditional Rental Income: $2393

Airbnb ROI: 9.72%

Traditional ROI: 3.7%

114 ADDISON COURT

CHESTER, MD

3 beds | 3 baths | 2,342 sq.ft.

$575,000

Airbnb cash on cash: 7.44%

Traditional cash on cash: 3.84%

Airbnb Rental Income: $6279

Traditional Rental Income: $3111

Airbnb ROI: 7.44%

Traditional ROI: 3.84%

132 CLAIBORNE STREET

CHESTER, MD

3 beds | 4 baths | 2,400 sq.ft.

$725,000

Airbnb cash on cash: 5.1%

Traditional cash on cash: 2.35%

Airbnb Rental Income: $6279

Traditional Rental Income: $3180

Airbnb ROI: 5.1%

Traditional ROI: 2.35%

307 SKIPPER LANE

CHESTER, MD

3 beds | 2 baths | 2,180 sq.ft.

$525,000

Airbnb cash on cash: 8.46%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $6279

Traditional Rental Income: $2587

Airbnb ROI: 8.46%