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 St New Windsor, MD Look at this gorgeous Colonial home featuring stunning craftsmanship and beautiful woodwor...	4 beds \| 1 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%
2140 Marston Rd New Windsor, MD Custom built 4 bedroom 3 bath home on a private 2 acre lot surrounded by farmland with ama...	4 beds \| 2 baths \| 3,209 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.34% Airbnb Rental Income: $null Traditional Rental Income: $2636 Airbnb ROI: N/A Traditional ROI: 2.34%
1183 JO APTER PL New Windsor, MD Welcome to 1183 Jo Apter Place, nestled in this quiet neighborhood in New Windsor, MD. Th...	3 beds \| 2 baths \| N/A	$414,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.48% Airbnb Rental Income: $null Traditional Rental Income: $2266 Airbnb ROI: N/A Traditional ROI: 3.48%
3788 Roop Rd New Windsor, MD Welcome to 3788 Roop Road, where quiet, serene country living meets everyday convenience. ...	3 beds \| 2 baths \| 2,343 sq.ft.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $2764 Airbnb ROI: N/A Traditional ROI: 2.57%
124 Church St New Windsor, MD Tucked back from the road and unlike anything nearby, 124 Church St blends the charm of a ...	3 beds \| 3 baths \| 1,736 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.79% Airbnb Rental Income: $null Traditional Rental Income: $2331 Airbnb ROI: N/A Traditional ROI: 4.79%
2812 Town View Cir New Windsor, MD Beautifully updated villa-style townhouse residence offering 3 bedrooms and 2.5 bathrooms ...	3 beds \| 2 baths \| 2,224 sq.ft.	$510,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $2407 Airbnb ROI: N/A Traditional ROI: 2.64%
1604 Old New Windsor Rd New Windsor, MD Welcome home to this charming single-family, split foyer residence nestled on a spacious t...	5 beds \| 2 baths \| 2,074 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.21% Airbnb Rental Income: $null Traditional Rental Income: $2579 Airbnb ROI: N/A Traditional ROI: 3.21%
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: -0.52% Traditional cash on cash: 0.91% Airbnb Rental Income: $693 Traditional Rental Income: $660 Airbnb ROI: -0.52% 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.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $4402 Airbnb ROI: N/A Traditional ROI: 4.29%
New Windsor New Windsor, MD New Windsor, New Windsor, MD 21776 \| Other	N/A beds \| N/A baths \| 500 sq.ft.	$625,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -1.11% Airbnb Rental Income: $693 Traditional Rental Income: $660 Airbnb ROI: -1.58% Traditional ROI: -1.11%
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	$174,900	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.75% Airbnb Rental Income: $693 Traditional Rental Income: $731 Airbnb ROI: -0.3% Traditional ROI: 1.75%
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.	$485,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.64% Airbnb Rental Income: $null Traditional Rental Income: $2238 Airbnb ROI: N/A Traditional ROI: 2.64%
Lot 6, South Parsonage Ln 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%
2108 Dennings Rd New Windsor, MD Superior Quality New construction by local builders JP & SB Homes ... Hurry and see this h...	4 beds \| 3 baths \| 3,457 sq.ft.	$874,997	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 Rd New Windsor, MD Price Improvement -This home is perfectly situated within 1.5 miles of the Taylorsville in...	4 beds \| 2 baths \| 2,688 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.27% Airbnb Rental Income: $null Traditional Rental Income: $3360 Airbnb ROI: N/A Traditional ROI: 3.27%
307 Church St New Windsor, MD Discover this magnificently unique "Painted Lady" Victorian nestled in the heart of histor...	3 beds \| 2 baths \| 2,366 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 4% Airbnb Rental Income: $null Traditional Rental Income: $2637 Airbnb ROI: N/A Traditional ROI: 4%
3235 Old Liberty Rd New Windsor, MD 3235 Old Liberty Rd, New Windsor, MD 21776 \| Single Family Residential	3 beds \| 2 baths \| 2,688 sq.ft.	$559,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.89% Airbnb Rental Income: $null Traditional Rental Income: $2170 Airbnb ROI: N/A Traditional ROI: 1.89%
2788 Town View Cir New Windsor, MD 2788 Town View Cir, New Windsor, MD 21776 \| Single Family Residential	5 beds \| 3 baths \| 2,770 sq.ft.	$629,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.46% Airbnb Rental Income: $null Traditional Rental Income: $2847 Airbnb ROI: N/A Traditional ROI: 2.46%
204 Church St New Windsor, MD	3 beds \| 2 baths \| 1,408 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.47% Airbnb Rental Income: $null Traditional Rental Income: $932 Airbnb ROI: N/A Traditional ROI: 0.47%
9855 Mckinstry Mill Rd New Windsor, MD You'll notice immediately as you approach this home that it is the perfect setting for rel...	5 beds \| 4 baths \| 3,952 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $5179 Airbnb ROI: N/A Traditional ROI: 4.8%
3300 Hawks Hill Rd New Windsor, MD Rare Opportunity! Single-Story Home on a Spacious 3-Acre Homesite Rarely available, this b...	2 beds \| 3 baths \| 2,714 sq.ft.	$565,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.2% Airbnb Rental Income: $null Traditional Rental Income: $3246 Airbnb ROI: N/A Traditional ROI: 4.2%
1216 Western Chapel Rd New Windsor, MD 1216 Western Chapel Rd, New Windsor, MD 21776 \| Single Family Residential	4 beds \| 3 baths \| 2,023 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.31% Airbnb Rental Income: $null Traditional Rental Income: $2655 Airbnb ROI: N/A Traditional ROI: 2.31%

Real Estate investment in New-windsor, MD

There are 26 properties for sale in the city of New Windsor . The median list price in New Windsor is $444,770 and the average price per square foot is $236. In June 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 26 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 St

New Windsor, MD

4 beds | 1 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%

2140 Marston Rd

New Windsor, MD

4 beds | 2 baths | 3,209 sq.ft.

$699,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.34%

Airbnb Rental Income: $null

Traditional Rental Income: $2636

Airbnb ROI: N/A

Traditional ROI: 2.34%

1183 JO APTER PL

New Windsor, MD

3 beds | 2 baths | N/A

$414,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.48%

Airbnb Rental Income: $null

Traditional Rental Income: $2266

Airbnb ROI: N/A

Traditional ROI: 3.48%

3788 Roop Rd

New Windsor, MD

3 beds | 2 baths | 2,343 sq.ft.

$639,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.57%

Airbnb Rental Income: $null

Traditional Rental Income: $2764

Airbnb ROI: N/A

Traditional ROI: 2.57%

124 Church St

New Windsor, MD

3 beds | 3 baths | 1,736 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.79%

Airbnb Rental Income: $null

Traditional Rental Income: $2331

Airbnb ROI: N/A

Traditional ROI: 4.79%

2812 Town View Cir

New Windsor, MD

3 beds | 2 baths | 2,224 sq.ft.

$510,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.64%

Airbnb Rental Income: $null

Traditional Rental Income: $2407

Airbnb ROI: N/A