Real Estate Investment Properties for Sale in Darlington, MD

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2454 Castleton Rd DARLINGTON, MD A beautiful high elevation and leveled private 3.5 acre lot that offers the potential to b...	N/A beds \| N/A baths \| 2,186 sq.ft.	$367,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $2361 Airbnb ROI: N/A Traditional ROI: 5.02%
2604 Castleton Rd DARLINGTON, MD 2604 Castleton Rd, DARLINGTON, MD 21034 \| Other	N/A beds \| N/A baths \| N/A	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.5% Airbnb Rental Income: $null Traditional Rental Income: $1053 Airbnb ROI: N/A Traditional ROI: -0.5%
3909 River Rd DARLINGTON, MD 3909 River Rd, DARLINGTON, MD 21034 \| Other	N/A beds \| N/A baths \| N/A	$285,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.5% Airbnb Rental Income: $null Traditional Rental Income: $1053 Airbnb ROI: N/A Traditional ROI: 1.5%
Jennings Ln DARLINGTON, MD Jennings Ln, DARLINGTON, MD 21034 \| Single Family Residential	1 beds \| 1 baths \| 1,200 sq.ft.	$134,900	Airbnb cash on cash: 0.33% Traditional cash on cash: 7.39% Airbnb Rental Income: $713 Traditional Rental Income: $1319 Airbnb ROI: 0.33% Traditional ROI: 7.39%
2302 Castleton Rd DARLINGTON, MD 2302 Castleton Rd, DARLINGTON, MD 21034 \| Other	N/A beds \| N/A baths \| N/A	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $1053 Airbnb ROI: N/A Traditional ROI: 2.98%
1959 Glen Cove Rd DARLINGTON, MD Welcome to peaceful country living at 1959 Glen Cove Road! Situated on a lovely .68-acre c...	2 beds \| 1 baths \| 1,008 sq.ft.	$205,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 7.12% Airbnb Rental Income: $1198 Traditional Rental Income: $1808 Airbnb ROI: 1.98% Traditional ROI: 7.12%
1642B Trappe Church Rd DARLINGTON, MD 1642B Trappe Church Rd, DARLINGTON, MD 21034 \| Single Family Residential	6 beds \| 3 baths \| 4,572 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.32% Airbnb Rental Income: $null Traditional Rental Income: $3101 Airbnb ROI: N/A Traditional ROI: 1.32%
3719 Dublin Rd DARLINGTON, MD 3719 Dublin Rd, DARLINGTON, MD 21034 \| Single Family Residential	4 beds \| 2 baths \| 2,090 sq.ft.	$439,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.63% Airbnb Rental Income: $null Traditional Rental Income: $2441 Airbnb ROI: N/A Traditional ROI: 3.63%
1636 Trappe Church Rd DARLINGTON, MD 1636 Trappe Church Rd, DARLINGTON, MD 21034 \| Multi Family	5 beds \| N/A baths \| 1,710 sq.ft.	$299,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.49% Airbnb Rental Income: $null Traditional Rental Income: $2230 Airbnb ROI: N/A Traditional ROI: 5.49%

Real Estate investment in Darlington, MD

There are 11 properties for sale in the city of Darlington . The median list price in Darlington is $1,361,685 and the average price per square foot is $764. In October 2026, the average monthly cash on cash return in Darlington is 3.00%. The average monthly rental income in Darlington is $1,808.

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

There are 11 investment properties available for sale in Darlington.

In 2026, the best neighborhood to buy investment property is DARLINGTON.

The ROI for Long-Term is higher than the Short-Term in Darlington with average rental income of $1,808.

Your search for investment property begins and ends here

Investment Property for Sale in Darlington, MD

2454 Castleton Rd

DARLINGTON, MD

N/A beds | N/A baths | 2,186 sq.ft.

$367,999

Airbnb cash on cash: N/A

Traditional cash on cash: 5.02%

Airbnb Rental Income: $null

Traditional Rental Income: $2361

Airbnb ROI: N/A

Traditional ROI: 5.02%

2604 Castleton Rd

DARLINGTON, MD

N/A beds | N/A baths | N/A

$650,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.5%

Airbnb Rental Income: $null

Traditional Rental Income: $1053

Airbnb ROI: N/A

Traditional ROI: -0.5%

3909 River Rd

DARLINGTON, MD

N/A beds | N/A baths | N/A

$285,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.5%

Airbnb Rental Income: $null

Traditional Rental Income: $1053

Airbnb ROI: N/A

Traditional ROI: 1.5%

Jennings Ln

DARLINGTON, MD

1 beds | 1 baths | 1,200 sq.ft.

$134,900

Airbnb cash on cash: 0.33%

Traditional cash on cash: 7.39%

Airbnb Rental Income: $713

Traditional Rental Income: $1319

Airbnb ROI: 0.33%

Traditional ROI: 7.39%

2302 Castleton Rd

DARLINGTON, MD

N/A beds | N/A baths | N/A

$199,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.98%

Airbnb Rental Income: $null

Traditional Rental Income: $1053

Airbnb ROI: N/A

Traditional ROI: 2.98%

1959 Glen Cove Rd

DARLINGTON, MD

2 beds | 1 baths | 1,008 sq.ft.

$205,000

Airbnb cash on cash: 1.98%

Traditional cash on cash: 7.12%

Airbnb Rental Income: $1198

Traditional Rental Income: $1808

Airbnb ROI: 1.98%

Traditional ROI: 7.12%

1642B Trappe Church Rd

DARLINGTON, MD

6 beds | 3 baths | 4,572 sq.ft.

$950,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.32%

Airbnb Rental Income: $null

Traditional Rental Income: $3101

Airbnb ROI: N/A

Traditional ROI: 1.32%

3719 Dublin Rd

DARLINGTON, MD

4 beds | 2 baths | 2,090 sq.ft.

$439,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.63%

Airbnb Rental Income: $null

Traditional Rental Income: $2441

Airbnb ROI: N/A