Real Estate Investment Properties for Sale in Jefferson, MD

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2640 JEFFERSON Pike Jefferson, MD NEW PRICE, NEW HVAC SYSTEM. Discover this beautifully updated home offering comfort, space...	3 beds \| 3 baths \| 2,056 sq.ft.	$524,900	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.44% Airbnb Rental Income: $2693 Traditional Rental Income: $2620 Airbnb ROI: 2.29% Traditional ROI: 3.44%
3801 BROOK DR Jefferson, MD Construction completed and move in ready! This Authentic Craftsman Home features an over...	4 beds \| 3 baths \| N/A	$589,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $3101 Airbnb ROI: N/A Traditional ROI: 4.31%
3830 JEFFERSON Pike Jefferson, MD Step into a beautifully renovated gem that seamlessly blends historic charm with modern co...	4 beds \| 2 baths \| 1,638 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.92% Airbnb Rental Income: $null Traditional Rental Income: $2442 Airbnb ROI: N/A Traditional ROI: 4.92%
3805 BEDFORD DR. Jefferson, MD Welcome to this beautifully updated gem, perfectly positioned on a spacious corner lot! Fr...	3 beds \| 3 baths \| 2,037 sq.ft.	$449,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 4.92% Airbnb Rental Income: $2693 Traditional Rental Income: $2931 Airbnb ROI: 2.84% Traditional ROI: 4.92%
4805 BENNINGTON Place E Jefferson, MD This stately yet inviting colonial home sits in the cozy town of Jefferson, nestled within...	4 beds \| 3 baths \| 3,946 sq.ft.	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $3270 Airbnb ROI: N/A Traditional ROI: 2.9%
3855 SHADYWOOD Drive unit: 2D #2D Jefferson, MD Welcome Home!! 2 Bedroom 2 Full Bath 2nd Floor Condo Nestled in the Private Briercrest Com...	2 beds \| 2 baths \| 930 sq.ft.	$245,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 5.11% Airbnb Rental Income: $1297 Traditional Rental Income: $1726 Airbnb ROI: 1.51% Traditional ROI: 5.11%
3856 SHADYWOOD unit: 3D #3D Jefferson, MD Welcome home to this beautifully updated 2-bedroom, 2-bath third-level condo in the desira...	2 beds \| 2 baths \| 1,100 sq.ft.	$270,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 5.35% Airbnb Rental Income: $1297 Traditional Rental Income: $1930 Airbnb ROI: 1.28% Traditional ROI: 5.35%
3707 COOL CREST Drive Jefferson, MD Offer deadline Tuesday 12/9 12pm. A picturesque drive down rolling hills, family farms, an...	5 beds \| 3 baths \| 2,004 sq.ft.	$640,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.19% Airbnb Rental Income: $null Traditional Rental Income: $3172 Airbnb ROI: N/A Traditional ROI: 3.19%
3856 SHADYWOOD DR #2B Jefferson, MD Welcome home to this beautifully updated 2-bedroom, 2-bath second-level condo located in t...	2 beds \| 2 baths \| N/A	$299,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 4.59% Airbnb Rental Income: $1297 Traditional Rental Income: $1853 Airbnb ROI: 1.18% Traditional ROI: 4.59%

Real Estate investment in Jefferson, MD

There are 9 properties for sale in the city of Jefferson . The median list price in Jefferson is $449,000 and the average price per square foot is $229. In December 2025, the average monthly cash on cash return in Jefferson is 5.00%. The average monthly rental income in Jefferson is $2,620.

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

There are 9 investment properties available for sale in Jefferson.

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

The ROI for Long-Term is higher than the Short-Term in Jefferson with average rental income of $2,620.

Your search for investment property begins and ends here

Investment Property for Sale in Jefferson, MD

2640 JEFFERSON Pike

Jefferson, MD

3 beds | 3 baths | 2,056 sq.ft.

$524,900

Airbnb cash on cash: 2.29%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $2693

Traditional Rental Income: $2620

Airbnb ROI: 2.29%

Traditional ROI: 3.44%

3801 BROOK DR

Jefferson, MD

4 beds | 3 baths | N/A

$589,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.31%

Airbnb Rental Income: $null

Traditional Rental Income: $3101

Airbnb ROI: N/A

Traditional ROI: 4.31%

3830 JEFFERSON Pike

Jefferson, MD

4 beds | 2 baths | 1,638 sq.ft.

$389,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2442

Airbnb ROI: N/A

Traditional ROI: 4.92%

3805 BEDFORD DR.

Jefferson, MD

3 beds | 3 baths | 2,037 sq.ft.

$449,000

Airbnb cash on cash: 2.84%

Traditional cash on cash: 4.92%

Airbnb Rental Income: $2693

Traditional Rental Income: $2931

Airbnb ROI: 2.84%

Traditional ROI: 4.92%

4805 BENNINGTON Place E

Jefferson, MD

4 beds | 3 baths | 3,946 sq.ft.

$695,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.9%

Airbnb Rental Income: $null

Traditional Rental Income: $3270

Airbnb ROI: N/A

Traditional ROI: 2.9%

3855 SHADYWOOD Drive unit: 2D #2D

Jefferson, MD

2 beds | 2 baths | 930 sq.ft.

$245,000

Airbnb cash on cash: 1.51%

Traditional cash on cash: 5.11%

Airbnb Rental Income: $1297

Traditional Rental Income: $1726

Airbnb ROI: 1.51%

Traditional ROI: 5.11%

3856 SHADYWOOD unit: 3D #3D

Jefferson, MD

2 beds | 2 baths | 1,100 sq.ft.

$270,000

Airbnb cash on cash: 1.28%

Traditional cash on cash: 5.35%

Airbnb Rental Income: $1297

Traditional Rental Income: $1930

Airbnb ROI: 1.28%

Traditional ROI: 5.35%

3707 COOL CREST Drive

Jefferson, MD

5 beds | 3 baths | 2,004 sq.ft.

$640,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.19%

Airbnb Rental Income: $null

Traditional Rental Income: $3172

Airbnb ROI: N/A