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
4033 CONOWINGO Road DARLINGTON, MD DREAM BIG! $20k PRICE IMPROVEMENT! Step into a storybook! This enchanting 4-bedroom, 2-ful...	4 beds \| 2 baths \| 2,595 sq.ft.	$389,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.57% Airbnb Rental Income: $null Traditional Rental Income: $2847 Airbnb ROI: N/A Traditional ROI: 5.57%
Investment Properties for Sale in Other Cities of Maryland
3029 HUDSON Street Baltimore , MD Welcome to this beautifully reimagined Canton residence, where historic charm meets modern...	4 beds \| 3 baths \| 1,748 sq.ft.	$495,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 3.56% Airbnb Rental Income: $4486 Traditional Rental Income: $2649 Airbnb ROI: 5.5% Traditional ROI: 3.56%
827 LIGHT Street Baltimore , MD ADJUSTED PRICED to sell! Current appraisal in hand! Featuring over $300,000 in improvement...	3 beds \| 4 baths \| 2,328 sq.ft.	$528,700	Airbnb cash on cash: 1.84% Traditional cash on cash: 3.05% Airbnb Rental Income: $2984 Traditional Rental Income: $2894 Airbnb ROI: 1.84% Traditional ROI: 3.05%
675 PRESIDENT Street unit: 2904 #2904 Baltimore , MD Elevated high above Harbor East, this impeccable two-story penthouse at The Vue offers an ...	4 beds \| 4 baths \| 5,071 sq.ft.	$2,695,000	Airbnb cash on cash: -1.57% Traditional cash on cash: -0.5% Airbnb Rental Income: $1948 Traditional Rental Income: $4106 Airbnb ROI: -1.57% Traditional ROI: -0.5%
847 W UNIVERSITY Parkway Baltimore , MD Classic Roland Park Residence of Timeless Quality and Exceptional Care Experience the perf...	4 beds \| 4 baths \| 2,282 sq.ft.	$649,500	Airbnb cash on cash: 1.15% Traditional cash on cash: 3.08% Airbnb Rental Income: $2952 Traditional Rental Income: $3441 Airbnb ROI: 1.15% Traditional ROI: 3.08%
1200 STEUART Street unit: 426 #426 Baltimore , MD Welcome to the largest one-bedroom, one-and-a-half-bath residence at Silo Point. This spac...	1 beds \| 2 baths \| 1,590 sq.ft.	$389,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 3.21% Airbnb Rental Income: $2320 Traditional Rental Income: $2585 Airbnb ROI: 0.91% Traditional ROI: 3.21%
1243 BATTERY Avenue Baltimore , MD Motivated Seller, Back on the Market!! Bonus offered if closed by the end of the month! We...	2 beds \| 2 baths \| 1,730 sq.ft.	$315,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 3.54% Airbnb Rental Income: $2848 Traditional Rental Income: $2216 Airbnb ROI: 3.43% Traditional ROI: 3.54%
3916 CLOVERHILL Road Baltimore , MD Discover your charming retreat in the heart of Tuscany/Canterbury. This delightful 5-bedro...	5 beds \| 2 baths \| 2,016 sq.ft.	$530,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 2.56% Airbnb Rental Income: $2247 Traditional Rental Income: $2612 Airbnb ROI: 0.69% Traditional ROI: 2.56%
16 138TH Street unit: 106 #106 Ocean City , MD Expansive 4-Bedroom Condo with Ocean Views in Island Breeze - Rarely Available! Welcome to...	4 beds \| 3 baths \| 2,570 sq.ft.	$950,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.53% Airbnb Rental Income: $4007 Traditional Rental Income: $3157 Airbnb ROI: 1.52% Traditional ROI: 1.53%
32 EAST Street Annapolis , MD	3 beds \| 3 baths \| 2,100 sq.ft.	$1,200,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 0.14% Airbnb Rental Income: $2680 Traditional Rental Income: $2245 Airbnb ROI: -0.04% Traditional ROI: 0.14%
23 STONEHENGE CIR #8 PIKESVILLE , MD Discover the charm of this beautifully maintained 2-bedroom, 2-bathroom condo in Stevenson...	2 beds \| 2 baths \| N/A	$229,224	Airbnb cash on cash: 2.5% Traditional cash on cash: 6.04% Airbnb Rental Income: $1441 Traditional Rental Income: $1778 Airbnb ROI: 2.5% Traditional ROI: 6.04%
500 FAIRWAY Court Baltimore , MD Welcome to this timeless and completely remodeled split-level home located at 500 Fairway ...	3 beds \| 3 baths \| 1,706 sq.ft.	$514,990	Airbnb cash on cash: 2.13% Traditional cash on cash: 3.99% Airbnb Rental Income: $2608 Traditional Rental Income: $2878 Airbnb ROI: 2.13% Traditional ROI: 3.99%
2933 FAIT Avenue Baltimore , MD Enjoy City life in this fully remolded home in Canton. The open floor plan of the main lev...	3 beds \| 3 baths \| 1,152 sq.ft.	$449,999	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.09% Airbnb Rental Income: $3308 Traditional Rental Income: $2089 Airbnb ROI: 3.23% Traditional ROI: 2.09%
4317 ROLAND SPRING Drive Baltimore , MD Single Family home in Roland Park Area for under $400,000! End of group townhome in Roland...	3 beds \| 4 baths \| 1,702 sq.ft.	$380,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.38% Airbnb Rental Income: $1545 Traditional Rental Income: $2583 Airbnb ROI: -0.79% Traditional ROI: 3.38%
3519 ROYSTON Avenue Baltimore , MD Beautifully Renovated 3-Bedroom, 2-Bath Home Step into modern comfort with this beautifull...	3 beds \| 2 baths \| 1,989 sq.ft.	$299,900	Airbnb cash on cash: 2.15% Traditional cash on cash: 5.68% Airbnb Rental Income: $1891 Traditional Rental Income: $2382 Airbnb ROI: 2.15% Traditional ROI: 5.68%
1433 E FEDERAL Street Baltimore , MD Welcome to your next investment opportunity at 1433 E Federal Street! This fully renovated...	3 beds \| 3 baths \| N/A	$220,000	Airbnb cash on cash: 7.63% Traditional cash on cash: 9.11% Airbnb Rental Income: $2949 Traditional Rental Income: $2577 Airbnb ROI: 7.63% Traditional ROI: 9.11%

Real Estate investment in Darlington, MD

There are 1 properties for sale in the city of Darlington . The median list price in Darlington is $235,000 and the average price per square foot is $145. In October 2025, the average monthly cash on cash return in Darlington is 13.00%. The average monthly rental income in Darlington is $2,386.

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

There are 1 investment properties available for sale in Darlington.

In 2025, 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 $2,386.

Your search for investment property begins and ends here

Investment Property for Sale in Darlington, MD

4033 CONOWINGO Road

DARLINGTON, MD

4 beds | 2 baths | 2,595 sq.ft.

$389,999

Airbnb cash on cash: N/A

Traditional cash on cash: 5.57%

Airbnb Rental Income: $null

Traditional Rental Income: $2847

Airbnb ROI: N/A

Traditional ROI: 5.57%

Investment Properties for Sale in Other Cities of Maryland

Baltimore , MD

4 beds | 3 baths | 1,748 sq.ft.

$495,000

Airbnb cash on cash: 5.5%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $4486

Traditional Rental Income: $2649

Airbnb ROI: 5.5%

Traditional ROI: 3.56%

Baltimore , MD

3 beds | 4 baths | 2,328 sq.ft.

$528,700

Airbnb cash on cash: 1.84%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $2984

Traditional Rental Income: $2894

Airbnb ROI: 1.84%

Traditional ROI: 3.05%

Baltimore , MD

4 beds | 4 baths | 5,071 sq.ft.

$2,695,000

Airbnb cash on cash: -1.57%

Traditional cash on cash: -0.5%

Airbnb Rental Income: $1948

Traditional Rental Income: $4106

Airbnb ROI: -1.57%

Traditional ROI: -0.5%

Baltimore , MD

4 beds | 4 baths | 2,282 sq.ft.

$649,500

Airbnb cash on cash: 1.15%

Traditional cash on cash: 3.08%

Airbnb Rental Income: $2952

Traditional Rental Income: $3441

Airbnb ROI: 1.15%

Traditional ROI: 3.08%

Baltimore , MD

1 beds | 2 baths | 1,590 sq.ft.

$389,000

Airbnb cash on cash: 0.91%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $2320

Traditional Rental Income: $2585

Airbnb ROI: 0.91%

Traditional ROI: 3.21%

Baltimore , MD

2 beds | 2 baths | 1,730 sq.ft.

$315,000

Airbnb cash on cash: 3.43%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $2848

Traditional Rental Income: $2216

Airbnb ROI: 3.43%

Traditional ROI: 3.54%

Baltimore , MD

5 beds | 2 baths | 2,016 sq.ft.

$530,000

Airbnb cash on cash: 0.69%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $2247

Traditional Rental Income: $2612

Airbnb ROI: 0.69%

Traditional ROI: 2.56%

Ocean City , MD

4 beds | 3 baths | 2,570 sq.ft.

$950,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 1.53%