Real Estate Investment Properties for Sale in New Windsor, MD

Looking for investment property in New Windsor, MD with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
4205 SAMS CREEK RD New Windsor, MD Approximately 120 acres comprised of two parcels including Land in Frederick and Carroll C...	3 beds \| 3 baths \| N/A	$1,600,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.77% Airbnb Rental Income: $null Traditional Rental Income: $2968 Airbnb ROI: N/A Traditional ROI: 0.77%
DENNINGS Road New Windsor, MD "Why buy someone else's dream when you can build your own? This stunning JP&Sb Homes custo...	4 beds \| 3 baths \| 3,457 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $3320 Airbnb ROI: N/A Traditional ROI: 2.91%
2823 GRAYBILL Court New Windsor, MD Surrounded by rolling hills and beautiful farmland but just minutes from shopping and ente...	4 beds \| 4 baths \| 3,037 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $3718 Airbnb ROI: N/A Traditional ROI: 4.72%
2613 LIBERTY Road New Windsor, MD Welcome to 2613 liberty road. Situated on over a quarter acre of land in the desirable tow...	2 beds \| 1 baths \| N/A	$100,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.26% Airbnb Rental Income: $null Traditional Rental Income: $1343 Airbnb ROI: N/A Traditional ROI: 10.26%
2807 CARLISLE Drive unit: 29 #29 New Windsor, MD Easy Living at its Best! Everything on one level with no steps. This detached home feature...	2 beds \| 2 baths \| 1,517 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $2363 Airbnb ROI: N/A Traditional ROI: 3.45%
2810 UNION SQUARE Road New Windsor, MD Welcome to The Reserves at New Windsor! This is a 55+ community that offers country living...	3 beds \| 3 baths \| 2,044 sq.ft.	$379,999	Airbnb cash on cash: N/A Traditional cash on cash: 7.29% Airbnb Rental Income: $null Traditional Rental Income: $3486 Airbnb ROI: N/A Traditional ROI: 7.29%
2995 SAMS CREEK Road New Windsor, MD This property is amazing!! The home has Luxurious features throughout. The moment you walk...	5 beds \| 5 baths \| 7,732 sq.ft.	$2,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.94% Airbnb Rental Income: $null Traditional Rental Income: $5457 Airbnb ROI: N/A Traditional ROI: 0.94%
3263 HAWKS HILL RD New Windsor, MD Nestled in the charming Walnut Hill subdivision, this delightful split foyer home offers a...	3 beds \| 2 baths \| N/A	$290,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.34% Airbnb Rental Income: $null Traditional Rental Income: $2053 Airbnb ROI: N/A Traditional ROI: 5.34%
14695 OAK ORCHARD Road New Windsor, MD Welcome Home! This grand brick colonial stands proudly on a beautifully landscaped rolling...	4 beds \| 3 baths \| 2,618 sq.ft.	$659,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.69% Airbnb Rental Income: $null Traditional Rental Income: $3454 Airbnb ROI: N/A Traditional ROI: 3.69%
3204 HOOPER Road New Windsor, MD THIS HOME IS LOADED WITH AMENITIES. OVERSIZED KITCHEN WITH GRANITE COUNTERTOPS, HARDWOOD F...	3 beds \| 4 baths \| 3,246 sq.ft.	$799,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.83% Airbnb Rental Income: $null Traditional Rental Income: $3414 Airbnb ROI: N/A Traditional ROI: 2.83%
216 MAIN Street New Windsor, MD Income-Producing Multi-Unit Gem with Endless Potential! Welcome to this versatile multi-un...	N/A beds \| N/A baths \| 2,016 sq.ft.	$239,900	Airbnb cash on cash: -2.26% Traditional cash on cash: 5.56% Airbnb Rental Income: $359 Traditional Rental Income: $1882 Airbnb ROI: -2.26% Traditional ROI: 5.56%
2824 GRAYBILL CT New Windsor, MD Updated rancher in a beautiful community. Picturesque views yet just minutes from shopping...	3 beds \| 2 baths \| N/A	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.28% Airbnb Rental Income: $null Traditional Rental Income: $2175 Airbnb ROI: N/A Traditional ROI: 3.28%
3720 BUFFALO RD New Windsor, MD Welcome to 3720 Buffalo Road, a distinguished residence where timeless elegance meets mode...	4 beds \| 4 baths \| N/A	$729,900	Airbnb cash on cash: N/A Traditional cash on cash: 3% Airbnb Rental Income: $null Traditional Rental Income: $3255 Airbnb ROI: N/A Traditional ROI: 3%
2851 UNION SQUARE Road unit: 68 #68 New Windsor, MD *OPEN HOUSE - SATURDAY OCTOBER 18 FROM 11AM-1PM* Welcome to 2851 Union Square Rd-where...	2 beds \| 3 baths \| 2,003 sq.ft.	$405,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.74% Airbnb Rental Income: $null Traditional Rental Income: $3478 Airbnb ROI: N/A Traditional ROI: 6.74%

Real Estate investment in New-windsor, MD

There are 14 properties for sale in the city of New Windsor . The median list price in New Windsor is $505,000 and the average price per square foot is $164. In October 2025, the average monthly cash on cash return in New Windsor is 4.00%. The average monthly rental income in New Windsor is $3,288.

New-windsor, MD Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 14 investment properties available for sale in New-windsor.

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

The ROI for Long-Term is higher than the Short-Term in New-windsor with average rental income of $3,288.

Your search for investment property begins and ends here

Investment Property for Sale in New Windsor, MD

4205 SAMS CREEK RD

New Windsor, MD

3 beds | 3 baths | N/A

$1,600,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.77%

Airbnb Rental Income: $null

Traditional Rental Income: $2968

Airbnb ROI: N/A

Traditional ROI: 0.77%

DENNINGS Road

New Windsor, MD

4 beds | 3 baths | 3,457 sq.ft.

$850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.91%

Airbnb Rental Income: $null

Traditional Rental Income: $3320

Airbnb ROI: N/A

Traditional ROI: 2.91%

2823 GRAYBILL Court

New Windsor, MD

4 beds | 4 baths | 3,037 sq.ft.

$575,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.72%

Airbnb Rental Income: $null

Traditional Rental Income: $3718

Airbnb ROI: N/A

Traditional ROI: 4.72%

2613 LIBERTY Road

New Windsor, MD

2 beds | 1 baths | N/A

$100,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.26%

Airbnb Rental Income: $null

Traditional Rental Income: $1343

Airbnb ROI: N/A

Traditional ROI: 10.26%

2807 CARLISLE Drive unit: 29 #29

New Windsor, MD

2 beds | 2 baths | 1,517 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.45%

Airbnb Rental Income: $null

Traditional Rental Income: $2363

Airbnb ROI: N/A

Traditional ROI: 3.45%

2810 UNION SQUARE Road

New Windsor, MD

3 beds | 3 baths | 2,044 sq.ft.

$379,999

Airbnb cash on cash: N/A

Traditional cash on cash: 7.29%

Airbnb Rental Income: $null

Traditional Rental Income: $3486

Airbnb ROI: N/A

Traditional ROI: 7.29%

2995 SAMS CREEK Road

New Windsor, MD

5 beds | 5 baths | 7,732 sq.ft.

$2,399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.94%

Airbnb Rental Income: $null

Traditional Rental Income: $5457

Airbnb ROI: N/A

Traditional ROI: 0.94%

3263 HAWKS HILL RD

New Windsor, MD

3 beds | 2 baths | N/A

$290,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.34%

Airbnb Rental Income: $null

Traditional Rental Income: $2053

Airbnb ROI: N/A