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%
221 MAIN STREET New Windsor, MD Priced to sell dont miss this opportunity! Here's your chance to own a piece of history in...	4 beds \| 2 baths \| 1,936 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.84% Airbnb Rental Income: $null Traditional Rental Income: $2555 Airbnb ROI: N/A Traditional ROI: 4.84%
DENNINGS ROAD New Windsor, MD "Why buy someone elses dream when you can build your own? This stunning JP&Sb Homes custom...	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	$115,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.85% Airbnb Rental Income: $null Traditional Rental Income: $1343 Airbnb ROI: N/A Traditional ROI: 8.85%
2820 UNION SQUARE ROAD #5 New Windsor, MD Stunning 3-Bedroom, 3-Bathroom Home with Finished Lower Level, Loft, and More! Welcome to ...	3 beds \| 4 baths \| 2,236 sq.ft.	$399,990	Airbnb cash on cash: N/A Traditional cash on cash: 6.55% Airbnb Rental Income: $null Traditional Rental Income: $3399 Airbnb ROI: N/A Traditional ROI: 6.55%
14958 NEW WINDSOR RD New Windsor, MD Welcome to your new cozy, quiet, comfortable home settled at 14958 New Windsor Rd! Nestled...	3 beds \| 1 baths \| 1,916 sq.ft.	$589,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $2053 Airbnb ROI: N/A Traditional ROI: 1.71%
2807 CARLISLE DRIVE #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.	$388,800	Airbnb cash on cash: N/A Traditional cash on cash: 3.01% Airbnb Rental Income: $null Traditional Rental Income: $2363 Airbnb ROI: N/A Traditional ROI: 3.01%
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.	$2,750,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.69% Airbnb Rental Income: $null Traditional Rental Income: $5457 Airbnb ROI: N/A Traditional ROI: 0.69%
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	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.27% Airbnb Rental Income: $null Traditional Rental Income: $2053 Airbnb ROI: N/A Traditional ROI: 4.27%
3169 VISTA COURT New Windsor, MD Atlee Ridge-Charming 4 Bedroom, 2 Fullbath Home with modern finishes. Welcome to this bea...	4 beds \| 2 baths \| 1,268 sq.ft.	$430,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.03% Airbnb Rental Income: $null Traditional Rental Income: $2465 Airbnb ROI: N/A Traditional ROI: 4.03%
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.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.58% Airbnb Rental Income: $null Traditional Rental Income: $3454 Airbnb ROI: N/A Traditional ROI: 3.58%
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%
2822 TOWN VIEW CIRCLE New Windsor, MD Fall in love with this absolutely stunning 5 bedroom / 3.5 bath masterpiece in the highly ...	5 beds \| 4 baths \| 4,024 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.31% Airbnb Rental Income: $null Traditional Rental Income: $3877 Airbnb ROI: N/A Traditional ROI: 4.31%
216 MAIN STREET New Windsor, MD Income-Producing Multi-Unit Gem with Endless Potential! Welcome to this versatile multi-...	N/A beds \| N/A baths \| 2,016 sq.ft.	$249,900	Airbnb cash on cash: -2.21% Traditional cash on cash: 5.3% Airbnb Rental Income: $359 Traditional Rental Income: $1882 Airbnb ROI: -2.21% Traditional ROI: 5.3%

Real Estate investment in New-windsor, MD

There are 16 properties for sale in the city of New Windsor . The median list price in New Windsor is $502,500 and the average price per square foot is $176. In September 2025, the average monthly cash on cash return in New Windsor is 4.00%. The average monthly rental income in New Windsor is $3,144.

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

There are 16 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 $3,144.

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%

221 MAIN STREET

New Windsor, MD

4 beds | 2 baths | 1,936 sq.ft.

$399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2555

Airbnb ROI: N/A

Traditional ROI: 4.84%

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

$115,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.85%

Airbnb Rental Income: $null

Traditional Rental Income: $1343

Airbnb ROI: N/A

Traditional ROI: 8.85%

2820 UNION SQUARE ROAD #5

New Windsor, MD

3 beds | 4 baths | 2,236 sq.ft.

$399,990

Airbnb cash on cash: N/A

Traditional cash on cash: 6.55%

Airbnb Rental Income: $null

Traditional Rental Income: $3399

Airbnb ROI: N/A

Traditional ROI: 6.55%

14958 NEW WINDSOR RD

New Windsor, MD

3 beds | 1 baths | 1,916 sq.ft.

$589,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.71%

Airbnb Rental Income: $null

Traditional Rental Income: $2053

Airbnb ROI: N/A

Traditional ROI: 1.71%

2807 CARLISLE DRIVE #29

New Windsor, MD

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

$388,800

Airbnb cash on cash: N/A

Traditional cash on cash: 3.01%

Airbnb Rental Income: $null

Traditional Rental Income: $2363

Airbnb ROI: N/A