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.	$75,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.48% Airbnb Rental Income: $null Traditional Rental Income: $1022 Airbnb ROI: N/A Traditional ROI: 10.48%
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 Price adjustment, ACT NOW. The sellers are motivated and must move. Open to ALL reasonable...	4 beds \| 2 baths \| 1,936 sq.ft.	$339,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $2555 Airbnb ROI: N/A Traditional ROI: 5.74%
414 High St New Windsor, MD Buy through Auction.com. This foreclosure property is a great opportunity to invest in thi...	3 beds \| 2 baths \| 2,668 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.04% Airbnb Rental Income: $null Traditional Rental Income: $2142 Airbnb ROI: N/A Traditional ROI: 3.04%
2843 TOWN VIEW Circle New Windsor, MD Welcome home to this stunning end unit craftsman townhome in the newer community of Snader...	5 beds \| 3 baths \| 3,740 sq.ft.	$579,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.18% Airbnb Rental Income: $null Traditional Rental Income: $3090 Airbnb ROI: N/A Traditional ROI: 3.18%
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: -0.89% Traditional cash on cash: 0.91% Airbnb Rental Income: $610 Traditional Rental Income: $660 Airbnb ROI: -0.89% Traditional ROI: 0.91%
120 Water St New Windsor, MD 120 Water St, New Windsor, MD 21776 \| Single Family Residential	6 beds \| 5 baths \| 5,242 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.08% Airbnb Rental Income: $null Traditional Rental Income: $4402 Airbnb ROI: N/A Traditional ROI: 4.08%
New Windsor New Windsor, MD New Windsor, New Windsor, MD 21776 \| Other	N/A beds \| N/A baths \| 500 sq.ft.	$675,000	Airbnb cash on cash: -1.72% Traditional cash on cash: -1.18% Airbnb Rental Income: $610 Traditional Rental Income: $660 Airbnb ROI: -1.72% Traditional ROI: -1.18%
3501 Sams Crk New Windsor, MD 3501 Sams Crk, New Windsor, MD 21776 \| Single Family Residential	3 beds \| 2 baths \| 3,688 sq.ft.	$2,350,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.36% Airbnb Rental Income: $null Traditional Rental Income: $1673 Airbnb ROI: N/A Traditional ROI: -1.36%
Parcel #22 Sams Creek Rd New Windsor, MD Parcel #22 Sams Creek Rd, New Windsor, MD 21776 \| Other	N/A beds \| N/A baths \| N/A	$199,900	Airbnb cash on cash: -0.89% Traditional cash on cash: 1.28% Airbnb Rental Income: $610 Traditional Rental Income: $731 Airbnb ROI: -0.89% Traditional ROI: 1.28%
118 S Clear Ridge Rd New Windsor, MD 118 S Clear Ridge Rd, New Windsor, MD 21776 \| Single Family Residential	3 beds \| 2 baths \| 2,050 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.52% Airbnb Rental Income: $null Traditional Rental Income: $2238 Airbnb ROI: N/A Traditional ROI: 2.52%
PARSONAGE Lane lot: 6, South New Windsor, MD Harlow model to be built by Grossnickle Construction. This home features an open living co...	3 beds \| 4 baths \| 2,352 sq.ft.	$733,048	Airbnb cash on cash: N/A Traditional cash on cash: 2.58% Airbnb Rental Income: $null Traditional Rental Income: $3281 Airbnb ROI: N/A Traditional ROI: 2.58%
14746 New Windsor Rd New Windsor, MD 14746 New Windsor Rd, New Windsor, MD 21776 \| Single Family Residential	6 beds \| 4 baths \| 5,020 sq.ft.	$895,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.58% Airbnb Rental Income: $null Traditional Rental Income: $3142 Airbnb ROI: N/A Traditional ROI: 1.58%
2108 DENNINGS Road New Windsor, MD Superior Quality New construction by local builders JP & SB Homes ... Hurry and see this h...	4 beds \| 4 baths \| 3,457 sq.ft.	$874,998	Airbnb cash on cash: N/A Traditional cash on cash: 3.61% Airbnb Rental Income: $null Traditional Rental Income: $3861 Airbnb ROI: N/A Traditional ROI: 3.61%
4036 ROOP Road New Windsor, MD Even though this property has a New Windsor zip code, it is perfectly situated within 1.5 ...	4 beds \| 3 baths \| 2,688 sq.ft.	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $3360 Airbnb ROI: N/A Traditional ROI: 2.91%
3238 ATLEE RIDGE Road New Windsor, MD Welcome to this beautifully updated home in the quiet, charming town of New Windsor, where...	4 beds \| 3 baths \| 1,959 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.22% Airbnb Rental Income: $null Traditional Rental Income: $3425 Airbnb ROI: N/A Traditional ROI: 5.22%
2723 TOWN VIEW CIR New Windsor, MD Welcome to this beautifully maintained townhome, built in 2020 and thoughtfully designed w...	3 beds \| 3 baths \| N/A	$449,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $2580 Airbnb ROI: N/A Traditional ROI: 3.83%
2845 UNION SQUARE RD #66 New Windsor, MD Welcome to 2845 Union Square Road, nestled in the highly sought-after 55+ community of New...	3 beds \| 3 baths \| N/A	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.27% Airbnb Rental Income: $null Traditional Rental Income: $2987 Airbnb ROI: N/A Traditional ROI: 4.27%
15601 WILDROSE CT New Windsor, MD Escape to your own private 5.89-acre wooded retreat. Tucked away among mature trees, this...	3 beds \| 2 baths \| N/A	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.49% Airbnb Rental Income: $null Traditional Rental Income: $2336 Airbnb ROI: N/A Traditional ROI: 2.49%

Real Estate investment in New-windsor, MD

There are 20 properties for sale in the city of New Windsor . The median list price in New Windsor is $479,000 and the average price per square foot is $256. In May 2026, the average monthly cash on cash return in New Windsor is 3.00%. The average monthly rental income in New Windsor is $2,555.

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

There are 20 investment properties available for sale in New-windsor.

In 2026, 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 $2,555.

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.

$75,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.48%

Airbnb Rental Income: $null

Traditional Rental Income: $1022

Airbnb ROI: N/A

Traditional ROI: 10.48%

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.

$339,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.74%

Airbnb Rental Income: $null

Traditional Rental Income: $2555

Airbnb ROI: N/A

Traditional ROI: 5.74%

414 High St

New Windsor, MD

3 beds | 2 baths | 2,668 sq.ft.

$449,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.04%

Airbnb Rental Income: $null

Traditional Rental Income: $2142

Airbnb ROI: N/A

Traditional ROI: 3.04%

2843 TOWN VIEW Circle

New Windsor, MD

5 beds | 3 baths | 3,740 sq.ft.

$579,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.18%

Airbnb Rental Income: $null

Traditional Rental Income: $3090

Airbnb ROI: N/A

Traditional ROI: 3.18%

3816-A Jim Smith Ln

New Windsor, MD

N/A beds | N/A baths | N/A

$199,900

Airbnb cash on cash: -0.89%

Traditional cash on cash: 0.91%

Airbnb Rental Income: $610

Traditional Rental Income: $660

Airbnb ROI: -0.89%

Traditional ROI: 0.91%

120 Water St

New Windsor, MD

6 beds | 5 baths | 5,242 sq.ft.

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.08%

Airbnb Rental Income: $null

Traditional Rental Income: $4402

Airbnb ROI: N/A

Traditional ROI: 4.08%

New Windsor

New Windsor, MD

N/A beds | N/A baths | 500 sq.ft.

$675,000

Airbnb cash on cash: -1.72%

Traditional cash on cash: -1.18%

Airbnb Rental Income: $610

Traditional Rental Income: $660

Airbnb ROI: -1.72%