Real Estate Investment Properties for Sale in Woodbine, MD

Looking for investment property in Woodbine, MD with high ROI ?

Explore a variety of short-term homes & houses in Woodbine, MD. Invest wisely with VRBO & Woodbine, 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 Woodbine, MD

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
15300 DOE HILL CT WOODBINE, MD Welcome to 15300 Doe Hill Court, a spectacular Colonial residence tucked away in the prest...	4 beds \| 5 baths \| N/A	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $4802 Airbnb ROI: N/A Traditional ROI: 2.57%
14816 BUSHY PARK Road WOODBINE, MD Welcome to this stunning 5-BR, 3-FB home in the heart of Woodbine! This turn-key residence...	5 beds \| 3 baths \| 3,431 sq.ft.	$774,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.83% Airbnb Rental Income: $null Traditional Rental Income: $3706 Airbnb ROI: N/A Traditional ROI: 2.83%
7330 WOODBINE Road WOODBINE, MD BUYER FINANCING FELL THROUGH: Here's your second chance!! Move in before the end of the ye...	3 beds \| 2 baths \| 1,482 sq.ft.	$459,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $2225 Airbnb ROI: N/A Traditional ROI: 3.03%
7326 JOHN PICKETT Road WOODBINE, MD What an incredible price for this single-family home! Another great listing in Woodbine! T...	3 beds \| 2 baths \| 1,996 sq.ft.	$370,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.04% Airbnb Rental Income: $null Traditional Rental Income: $2942 Airbnb ROI: N/A Traditional ROI: 6.04%
869 MORGAN STATION Road WOODBINE, MD Nestled on a picturesque 1.15-acre lot, this to-be-built custom home by Catonsville Homes ...	5 beds \| 6 baths \| 4,960 sq.ft.	$1,799,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.93% Airbnb Rental Income: $null Traditional Rental Income: $6927 Airbnb ROI: N/A Traditional ROI: 2.93%
2686 -B JENNINGS CHAPEL RD WOODBINE, MD 2686 Jennings Chapel Rd, Woodbine, MD 21797 3.36 Acres \| Private Well \| No HOA \| Adjacent ...	5 beds \| 5 baths \| 4,813 sq.ft.	$1,480,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.84% Airbnb Rental Income: $null Traditional Rental Income: $5511 Airbnb ROI: N/A Traditional ROI: 2.84%
2698 JENNINGS CHAPEL Road WOODBINE, MD MAGNIFICENT 63-ACRE EQUESTRIAN ESTATE Located in Western Howard County, Maryland Whether y...	3 beds \| 2 baths \| 2,233 sq.ft.	$4,750,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.61% Airbnb Rental Income: $null Traditional Rental Income: $2461 Airbnb ROI: N/A Traditional ROI: -0.61%
16005 FIELDS END Court WOODBINE, MD A true Southern Living gem! Designed by renowned architect William Poole, this exquisite s...	4 beds \| 3 baths \| 3,226 sq.ft.	$1,099,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.28% Airbnb Rental Income: $null Traditional Rental Income: $3387 Airbnb ROI: N/A Traditional ROI: 1.28%
15521 FOXPAW TRL NW WOODBINE, MD Welcome to 15521 Foxpaw NW Trail, a spectacular Colonial nestled in the prestigious Foxpor...	5 beds \| 4 baths \| N/A	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.55% Airbnb Rental Income: $null Traditional Rental Income: $3767 Airbnb ROI: N/A Traditional ROI: 1.55%
16020 FIELDS END Court WOODBINE, MD Beautiful ranch-style residence offering 3 bedrooms, 2.5 bathrooms, and 2,124 finished squ...	3 beds \| 3 baths \| 2,124 sq.ft.	$829,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.65% Airbnb Rental Income: $null Traditional Rental Income: $2977 Airbnb ROI: N/A Traditional ROI: 1.65%
863 MORGAN STATION Road WOODBINE, MD Introducing Catonsville Homes in Woodbine! Construction is set to commence in January with...	5 beds \| 6 baths \| 4,535 sq.ft.	$1,599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.21% Airbnb Rental Income: $null Traditional Rental Income: $6552 Airbnb ROI: N/A Traditional ROI: 3.21%
3211 HAYLOFT Court WOODBINE, MD Beautifully Updated 4 Bedroom, 3 Bath Home with 2-Car Garage. Welcome home to this charmin...	4 beds \| 3 baths \| 2,444 sq.ft.	$775,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.39% Airbnb Rental Income: $null Traditional Rental Income: $3305 Airbnb ROI: N/A Traditional ROI: 2.39%
3751 JENNINGS CHAPEL RD WOODBINE, MD Discover the promise of your dream home in this stunning new construction, thoughtfully de...	4 beds \| 4 baths \| 1,620 sq.ft.	$1,789,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.56% Airbnb Rental Income: $null Traditional Rental Income: $2836 Airbnb ROI: N/A Traditional ROI: 0.56%

Real Estate investment in Woodbine, MD

There are 13 properties for sale in the city of Woodbine . The median list price in Woodbine is $1,100,000 and the average price per square foot is $368. In December 2025, the average monthly cash on cash return in Woodbine is 3.00%. The average monthly rental income in Woodbine is $3,387.

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

There are 13 investment properties available for sale in Woodbine.

In 2025, the best neighborhood to buy investment property is WOODBINE.

The ROI for Short-Term is higher than the Long-Term in Woodbine with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Woodbine, MD

15300 DOE HILL CT

WOODBINE, MD

4 beds | 5 baths | N/A

$1,100,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.57%

Airbnb Rental Income: $null

Traditional Rental Income: $4802

Airbnb ROI: N/A

Traditional ROI: 2.57%

14816 BUSHY PARK Road

WOODBINE, MD

5 beds | 3 baths | 3,431 sq.ft.

$774,999

Airbnb cash on cash: N/A

Traditional cash on cash: 2.83%

Airbnb Rental Income: $null

Traditional Rental Income: $3706

Airbnb ROI: N/A

Traditional ROI: 2.83%

7330 WOODBINE Road

WOODBINE, MD

3 beds | 2 baths | 1,482 sq.ft.

$459,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.03%

Airbnb Rental Income: $null

Traditional Rental Income: $2225

Airbnb ROI: N/A

Traditional ROI: 3.03%

7326 JOHN PICKETT Road

WOODBINE, MD

3 beds | 2 baths | 1,996 sq.ft.

$370,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.04%

Airbnb Rental Income: $null

Traditional Rental Income: $2942

Airbnb ROI: N/A

Traditional ROI: 6.04%

869 MORGAN STATION Road

WOODBINE, MD

5 beds | 6 baths | 4,960 sq.ft.

$1,799,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.93%

Airbnb Rental Income: $null

Traditional Rental Income: $6927

Airbnb ROI: N/A

Traditional ROI: 2.93%

2686 -B JENNINGS CHAPEL RD

WOODBINE, MD

5 beds | 5 baths | 4,813 sq.ft.

$1,480,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.84%

Airbnb Rental Income: $null

Traditional Rental Income: $5511

Airbnb ROI: N/A

Traditional ROI: 2.84%

2698 JENNINGS CHAPEL Road

WOODBINE, MD

3 beds | 2 baths | 2,233 sq.ft.

$4,750,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.61%

Airbnb Rental Income: $null

Traditional Rental Income: $2461

Airbnb ROI: N/A

Traditional ROI: -0.61%

16005 FIELDS END Court

WOODBINE, MD

4 beds | 3 baths | 3,226 sq.ft.

$1,099,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.28%

Airbnb Rental Income: $null

Traditional Rental Income: $3387

Airbnb ROI: N/A