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
4328 Ridge Rd #13 New Windsor, MD 4328 Ridge Rd #13, New Windsor, MD 21771 \| Single Family Residential	1 beds \| 1 baths \| 850 sq.ft.	$79,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.88% Airbnb Rental Income: $null Traditional Rental Income: $1022 Airbnb ROI: N/A Traditional ROI: 9.88%
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 BRAND NEW Luxury SPA/HotTub has been installed and Gallagher Pools and Spas will teach new...	4 beds \| 4 baths \| 3,037 sq.ft.	$565,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.82% Airbnb Rental Income: $null Traditional Rental Income: $3718 Airbnb ROI: N/A Traditional ROI: 4.82%
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%
15030 NEW WINDSOR Road New Windsor, MD Custom built craftsman home nestled on 1.7 acres in rural Frederick County. Experience the...	4 beds \| 4 baths \| 2,962 sq.ft.	$1,051,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.33% Airbnb Rental Income: $null Traditional Rental Income: $3792 Airbnb ROI: N/A Traditional ROI: 2.33%
14695 OAK ORCHARD RD New Windsor, MD Gorgeous all-brick Colonial in a prime location offering timeless curb appeal and three fi...	4 beds \| 3 baths \| N/A	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.9% Airbnb Rental Income: $null Traditional Rental Income: $3454 Airbnb ROI: N/A Traditional ROI: 3.9%
1037 WESTERN CHAPEL New Windsor, MD Nicely landscaped corner-lot home in good condition. The home was updated a few years ago ...	3 beds \| 2 baths \| 2,344 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $2649 Airbnb ROI: N/A Traditional ROI: 3.84%
3816-A Jim Smith Ln New Windsor, MD 3816-A Jim Smith Ln, New Windsor, MD 21776 \| Other	N/A beds \| N/A baths \| N/A	$199,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 4.02% Airbnb Rental Income: $845 Traditional Rental Income: $1250 Airbnb ROI: 0.15% Traditional ROI: 4.02%
14695 Oak Orchard Rd New Windsor, MD 14695 Oak Orchard Rd, New Windsor, MD 21776 \| Single Family Residential	4 beds \| 2 baths \| 2,088 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.55% Airbnb Rental Income: $null Traditional Rental Income: $2215 Airbnb ROI: N/A Traditional ROI: 1.55%
2461 Old New Windsor Pike New Windsor, MD 2461 Old New Windsor Pike, New Windsor, MD 21776 \| Single Family Residential	3 beds \| 2 baths \| 1,817 sq.ft.	$714,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.91% Airbnb Rental Income: $null Traditional Rental Income: $2087 Airbnb ROI: N/A Traditional ROI: 0.91%
New Windsor New Windsor, MD New Windsor, New Windsor, MD 21776 \| Other	1 beds \| 1 baths \| 500 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.32% Airbnb Rental Income: $null Traditional Rental Income: $660 Airbnb ROI: N/A Traditional ROI: 0.32%
10015 Parsonage Ln New Windsor, MD 10015 Parsonage Ln, New Windsor, MD 21776 \| Other	N/A beds \| N/A baths \| N/A	$189,900	Airbnb cash on cash: 0.27% Traditional cash on cash: 1.07% Airbnb Rental Income: $845 Traditional Rental Income: $660 Airbnb ROI: 0.27% Traditional ROI: 1.07%

Real Estate investment in New-windsor, MD

There are 12 properties for sale in the city of New Windsor . The median list price in New Windsor is $479,999 and the average price per square foot is $229. In January 2026, the average monthly cash on cash return in New Windsor is 3.00%. The average monthly rental income in New Windsor is $2,151.

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

There are 12 investment properties available for sale in New-windsor.

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

The ROI for Short-Term is higher than the Long-Term in New-windsor with average rental income of $845.

Your search for investment property begins and ends here

Investment Property for Sale in New Windsor, MD

4328 Ridge Rd #13

New Windsor, MD

1 beds | 1 baths | 850 sq.ft.

$79,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.88%

Airbnb Rental Income: $null

Traditional Rental Income: $1022

Airbnb ROI: N/A

Traditional ROI: 9.88%

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.

$565,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.82%

Airbnb Rental Income: $null

Traditional Rental Income: $3718

Airbnb ROI: N/A

Traditional ROI: 4.82%

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%

15030 NEW WINDSOR Road

New Windsor, MD

4 beds | 4 baths | 2,962 sq.ft.

$1,051,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.33%

Airbnb Rental Income: $null

Traditional Rental Income: $3792

Airbnb ROI: N/A

Traditional ROI: 2.33%

14695 OAK ORCHARD RD

New Windsor, MD

4 beds | 3 baths | N/A

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.9%

Airbnb Rental Income: $null

Traditional Rental Income: $3454

Airbnb ROI: N/A

Traditional ROI: 3.9%

1037 WESTERN CHAPEL

New Windsor, MD

3 beds | 2 baths | 2,344 sq.ft.

$475,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2649

Airbnb ROI: N/A