Real Estate Investment Properties for Sale in New Windsor, NY

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

Explore a variety of short-term homes & houses in New Windsor, NY. Invest wisely with VRBO & New Windsor, NY Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in New Windsor, NY

Search for Single Family Residential for Sale in New Windsor, New York. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 45 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1 Townsend Street New Windsor, NY Welcome to 1 Townsend Street, a well-maintained raised ranch set on a quiet cul-de-sac alo...	4 beds \| 3 baths \| 2,088 sq.ft.	$489,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 4.48% Airbnb Rental Income: $3852 Traditional Rental Income: $3607 Airbnb ROI: 3.2% Traditional ROI: 4.48%
3 Clemence Drive New Windsor, NY Tucked in a quiet cul-de-sac in the sought after Cornwall School District this reimagined ...	4 beds \| 3 baths \| 3,653 sq.ft.	$825,000	Airbnb cash on cash: 0.54% Traditional cash on cash: 1.94% Airbnb Rental Income: $3852 Traditional Rental Income: $4098 Airbnb ROI: 0.54% Traditional ROI: 1.94%
545 Shore Drive New Windsor, NY Discover this stunning 3-level lakefront gem in the heart of the Hudson Valley just a quic...	4 beds \| 3 baths \| 2,695 sq.ft.	$695,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 3.31% Airbnb Rental Income: $3852 Traditional Rental Income: $4074 Airbnb ROI: 1.69% Traditional ROI: 3.31%
155 Erie Avenue New Windsor, NY Home, SWEET home! Step inside this updated Craftsman where natural light pervades througho...	3 beds \| 2 baths \| 1,192 sq.ft.	$389,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 4.88% Airbnb Rental Income: $2604 Traditional Rental Income: $2671 Airbnb ROI: 2.99% Traditional ROI: 4.88%
15 Queen Street New Windsor, NY Check out this charming brick 3 bedroom 1 bath home in the Town of New Windsor. This home ...	3 beds \| 1 baths \| 1,350 sq.ft.	$425,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 2.97% Airbnb Rental Income: $2604 Traditional Rental Income: $2443 Airbnb ROI: 1.81% Traditional ROI: 2.97%
404 Carlton Circle New Windsor, NY Welcome to this Hi-Ranch nestled in a cul-de-sac in the heart of New Windsor. Walk into th...	3 beds \| 3 baths \| 2,146 sq.ft.	$510,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 4.41% Airbnb Rental Income: $2604 Traditional Rental Income: $3497 Airbnb ROI: 1.23% Traditional ROI: 4.41%
6 Barclay Road New Windsor, NY Enjoy seasonal views of the Hudson River from this sprawling 3 bedroom, 3.5 bathroom stone...	3 beds \| 4 baths \| 2,517 sq.ft.	$499,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 5.4% Airbnb Rental Income: $2604 Traditional Rental Income: $4238 Airbnb ROI: 0.56% Traditional ROI: 5.4%
11 Willow Lane New Windsor, NY Welcome home to this charming L- shaped brick ranch in desirable New Windsor! Featuring 3...	3 beds \| 1 baths \| 1,517 sq.ft.	$437,500	Airbnb cash on cash: 1.77% Traditional cash on cash: 3.15% Airbnb Rental Income: $2604 Traditional Rental Income: $2546 Airbnb ROI: 1.77% Traditional ROI: 3.15%
355 Temple Hill Road New Windsor, NY Well-maintained, move-in ready single family home on 1 acre. Finished walk-out basement to...	3 beds \| 3 baths \| 1,920 sq.ft.	$459,900	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.84% Airbnb Rental Income: $2604 Traditional Rental Income: $2762 Airbnb ROI: 2.03% Traditional ROI: 3.84%
70 Meadowbrook Lane New Windsor, NY Welcome to this beautiful home! Located on a private road in Cornwall. This 3 bedroom, 1 b...	3 beds \| 1 baths \| 1,525 sq.ft.	$299,900	Airbnb cash on cash: 3.06% Traditional cash on cash: 3.61% Airbnb Rental Income: $2604 Traditional Rental Income: $2138 Airbnb ROI: 3.06% Traditional ROI: 3.61%
56 Frank Street New Windsor, NY Luxury, Comfort, and Convenience Await at Meadowbrook Estates! Discover the Brook Model,...	4 beds \| 4 baths \| 2,791 sq.ft.	$875,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.85% Airbnb Rental Income: $3852 Traditional Rental Income: $5522 Airbnb ROI: 0.78% Traditional ROI: 3.85%
710 Hewitt Lane New Windsor, NY Step into Your Dream Home Just Steps from the Hudson River! This stunning property in...	2 beds \| 2 baths \| 1,310 sq.ft.	$318,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 5% Airbnb Rental Income: $2118 Traditional Rental Income: $2624 Airbnb ROI: 1.5% Traditional ROI: 5%
108 Parkdale Drive New Windsor, NY Beautiful 3 bedroom Bi Level in the town of New Windsor close to close to schools, shoppi...	3 beds \| 3 baths \| 1,883 sq.ft.	$515,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.78% Airbnb Rental Income: $2604 Traditional Rental Income: $3198 Airbnb ROI: 1.25% Traditional ROI: 3.78%
107 Denniston Drive New Windsor, NY Welcome to this stunning 3,065 square foot estate, nestled on 1.70 acres of beautifully la...	4 beds \| 3 baths \| 3,065 sq.ft.	$849,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 1.93% Airbnb Rental Income: $3852 Traditional Rental Income: $4197 Airbnb ROI: 0.44% Traditional ROI: 1.93%
263 Quassaick Avenue New Windsor, NY Discover the charm and potential of this inviting two-bedroom, one-bathroom home nestled i...	2 beds \| 1 baths \| 1,117 sq.ft.	$385,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 3.21% Airbnb Rental Income: $2118 Traditional Rental Income: $2175 Airbnb ROI: 1.55% Traditional ROI: 3.21%
11 Queen Street New Windsor, NY PRICE IMPROVEMENT! Lots of value for this beautifully renovated, very spacious 5 bedroom, ...	5 beds \| 3 baths \| 2,400 sq.ft.	$469,999	Airbnb cash on cash: 1.85% Traditional cash on cash: 6.01% Airbnb Rental Income: $2731 Traditional Rental Income: $3918 Airbnb ROI: 1.85% Traditional ROI: 6.01%
10 Oakwood Terrace #118 New Windsor, NY Charming, Updated 1-Bedroom Co-Op â Second-Floor End Unit in Prime New Windsor Location ...	1 beds \| 1 baths \| 850 sq.ft.	$149,999	Airbnb cash on cash: -0.6% Traditional cash on cash: 3.75% Airbnb Rental Income: $1614 Traditional Rental Income: $1779 Airbnb ROI: -0.6% Traditional ROI: 3.75%
38 Panorama Drive New Windsor, NY MOTIVATED SELLER - BRING ALL OFFERS! Welcome to an exceptional opportunity to own nearly 3...	4 beds \| 3 baths \| 2,808 sq.ft.	$695,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 3.01% Airbnb Rental Income: $3852 Traditional Rental Income: $4057 Airbnb ROI: 1.41% Traditional ROI: 3.01%
13 Valley View Drive New Windsor, NY Incredible Price Adjustment!! Priced positioned to sell !! Great opportunity to own thi...	3 beds \| 2 baths \| 2,252 sq.ft.	$449,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 4.54% Airbnb Rental Income: $2604 Traditional Rental Income: $3234 Airbnb ROI: 1.56% Traditional ROI: 4.54%
18 Park Hill Drive New Windsor, NY Welcome to 18 Park Hill Driveâa perfect place to start your homeownership journey! This ...	3 beds \| 2 baths \| 2,100 sq.ft.	$479,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 4.51% Airbnb Rental Income: $2604 Traditional Rental Income: $3475 Airbnb ROI: 1.17% Traditional ROI: 4.51%
412 Hawthorn Way New Windsor, NY Welcome to The Grove at New Windsor! This young townhome development offers a wonderful al...	3 beds \| 3 baths \| 2,139 sq.ft.	$475,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 3.22% Airbnb Rental Income: $2604 Traditional Rental Income: $3340 Airbnb ROI: 0.16% Traditional ROI: 3.22%
313 Chestnut Avenue New Windsor, NY Welcome to 313 Chestnut Avenue in New Windsor, NYâan inviting and beautifully maintained...	4 beds \| 3 baths \| 2,821 sq.ft.	$599,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 4.29% Airbnb Rental Income: $3852 Traditional Rental Income: $4011 Airbnb ROI: 2.52% Traditional ROI: 4.29%
14 Cimorelli Drive New Windsor, NY Charming 4-Bedroom Colonial on Quiet Cul-de-Sac with Dream Backyard Tucked away at the en...	4 beds \| 2 baths \| 1,908 sq.ft.	$539,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 3.86% Airbnb Rental Income: $3852 Traditional Rental Income: $3431 Airbnb ROI: 3.05% Traditional ROI: 3.86%
12 Oxford Road New Windsor, NY Welcome to 12 Oxford Road in the sought after area of New Windsor! Tucked away on a peace...	3 beds \| 2 baths \| 1,500 sq.ft.	$489,999	Airbnb cash on cash: 1.63% Traditional cash on cash: 3.37% Airbnb Rental Income: $2604 Traditional Rental Income: $2776 Airbnb ROI: 1.63% Traditional ROI: 3.37%
212 Hawthorn Way New Windsor, NY Welcome to The Grove at New Windsor, a stylish townhome community offering a great alterna...	3 beds \| 3 baths \| 2,139 sq.ft.	$475,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 3.91% Airbnb Rental Income: $2604 Traditional Rental Income: $3648 Airbnb ROI: 0.16% Traditional ROI: 3.91%
60 Creamery Drive New Windsor, NY Welcome to this beautifully maintained 3-bedroom, 2-bath raised ranch in the highly desira...	3 beds \| 2 baths \| 1,980 sq.ft.	$499,999	Airbnb cash on cash: 1.04% Traditional cash on cash: 4.84% Airbnb Rental Income: $2604 Traditional Rental Income: $3758 Airbnb ROI: 1.04% Traditional ROI: 4.84%
323 Sycamore Drive New Windsor, NY Welcome to 323 Sycamore Dr., a spacious colonial in New Windsor offering comfort, versatil...	4 beds \| 4 baths \| 3,512 sq.ft.	$699,999	Airbnb cash on cash: 1.77% Traditional cash on cash: 4.54% Airbnb Rental Income: $3852 Traditional Rental Income: $4830 Airbnb ROI: 1.77% Traditional ROI: 4.54%
1802 Hawthorn Way New Windsor, NY Welcome to 1802 Hawthorn Way, a well-maintained 3-bedroom, 2.5-bath end-unit home located ...	3 beds \| 3 baths \| 2,139 sq.ft.	$474,999	Airbnb cash on cash: 0.16% Traditional cash on cash: 3.18% Airbnb Rental Income: $2604 Traditional Rental Income: $3323 Airbnb ROI: 0.16% Traditional ROI: 3.18%
121 Sycamore Drive New Windsor, NY This three-bedroom, one-bath home offers a wonderful opportunity to create your dream retr...	3 beds \| 1 baths \| 1,074 sq.ft.	$399,900	Airbnb cash on cash: 2.34% Traditional cash on cash: 2.86% Airbnb Rental Income: $2604 Traditional Rental Income: $2175 Airbnb ROI: 2.34% Traditional ROI: 2.86%
35 Guernsey Drive New Windsor, NY BUTTER HILL ESTATES!! SPECTACULAR SPLIT! Prime Corner Lot! Open Floor Plan! 3 Bedrooms! 2 ...	3 beds \| 3 baths \| 1,640 sq.ft.	$474,900	Airbnb cash on cash: 1.6% Traditional cash on cash: 4.46% Airbnb Rental Income: $2604 Traditional Rental Income: $3252 Airbnb ROI: 1.6% Traditional ROI: 4.46%
14 Coffey Avenue New Windsor, NY CALLING ALL BARGAIN HUNTERS & FEARLESS RENOVATORS! This New Windsor home is loaded with po...	2 beds \| 1 baths \| 1,001 sq.ft.	$215,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 7.5% Airbnb Rental Income: $2118 Traditional Rental Income: $2098 Airbnb ROI: 4.94% Traditional ROI: 7.5%
74 Red Maple Way New Windsor, NY Welcome to 74 Red Maple Way at Windsor Woods, one of New Windsor's premier cul-de-sac comm...	5 beds \| 3 baths \| 3,538 sq.ft.	$709,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 2.89% Airbnb Rental Income: $2731 Traditional Rental Income: $3901 Airbnb ROI: 0.15% Traditional ROI: 2.89%
11 Hudson Drive New Windsor, NY BACK ON THE MARKET (Buyers Failed to Perform) ***Missed it the first time?? Here's your do...	4 beds \| 2 baths \| 1,408 sq.ft.	$372,500	Airbnb cash on cash: 5.87% Traditional cash on cash: 6.39% Airbnb Rental Income: $3852 Traditional Rental Income: $3202 Airbnb ROI: 5.87% Traditional ROI: 6.39%
222 Margo Street New Windsor, NY Mid-Century Charm Meets Modern Comfort on Margo Street Step into timeless elegance and eve...	3 beds \| 2 baths \| 1,479 sq.ft.	$435,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 4.81% Airbnb Rental Income: $2604 Traditional Rental Income: $3212 Airbnb ROI: 1.78% Traditional ROI: 4.81%
458 Mount Airy Road New Windsor, NY Wonderful RANCH home in the CORNWALL School District. Situated on a picturesque ONE-ACRE L...	3 beds \| 3 baths \| 1,128 sq.ft.	$450,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 5.21% Airbnb Rental Income: $2604 Traditional Rental Income: $3375 Airbnb ROI: 1.9% Traditional ROI: 5.21%
303 Windsor Highway New Windsor, NY Call listing agent	2 beds \| 1 baths \| 600 sq.ft.	$450,000	Airbnb cash on cash: -1.73% Traditional cash on cash: -1.47% Airbnb Rental Income: $2118 Traditional Rental Income: $1686 Airbnb ROI: -1.73% Traditional ROI: -1.47%
12 Provost Drive New Windsor, NY Welcome to 12 Provost Drive, located in a quiet and established New Windsor neighborhood, ...	3 beds \| 1 baths \| 1,296 sq.ft.	$388,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 3.36% Airbnb Rental Income: $2604 Traditional Rental Income: $2383 Airbnb ROI: 2.25% Traditional ROI: 3.36%
223 Margo Street New Windsor, NY CALLING ALL INVESTORS AND FIRST TIME HOME BUYERS this could be the perfect opportunity for...	3 beds \| 2 baths \| 1,691 sq.ft.	$410,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 5.39% Airbnb Rental Income: $2604 Traditional Rental Income: $3156 Airbnb ROI: 2.33% Traditional ROI: 5.39%
81 Blooming Grove Turnpike New Windsor, NY Welcome to 81 Blooming Grove Turnpike, New Windsor, NY - a spacious and versatile Cape Cod...	3 beds \| 3 baths \| 2,230 sq.ft.	$484,999	Airbnb cash on cash: 1.33% Traditional cash on cash: 5.19% Airbnb Rental Income: $2604 Traditional Rental Income: $3730 Airbnb ROI: 1.33% Traditional ROI: 5.19%
40 Clara Avenue New Windsor, NY Tucked away at the end of the street on a peaceful, level property, 40 Clara Ave offers th...	3 beds \| 2 baths \| 3,070 sq.ft.	$599,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.94% Airbnb Rental Income: $2604 Traditional Rental Income: $2964 Airbnb ROI: 0.18% Traditional ROI: 1.94%

Your search for investment property begins and ends here

Single Family Homes for Sale in New Windsor, NY

1 Townsend Street

New Windsor, NY

4 beds | 3 baths | 2,088 sq.ft.

$489,000

Airbnb cash on cash: 3.2%

Traditional cash on cash: 4.48%

Airbnb Rental Income: $3852

Traditional Rental Income: $3607

Airbnb ROI: 3.2%

Traditional ROI: 4.48%

3 Clemence Drive

New Windsor, NY

4 beds | 3 baths | 3,653 sq.ft.

$825,000

Airbnb cash on cash: 0.54%

Traditional cash on cash: 1.94%

Airbnb Rental Income: $3852

Traditional Rental Income: $4098

Airbnb ROI: 0.54%

Traditional ROI: 1.94%

545 Shore Drive

New Windsor, NY

4 beds | 3 baths | 2,695 sq.ft.

$695,000

Airbnb cash on cash: 1.69%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $3852

Traditional Rental Income: $4074

Airbnb ROI: 1.69%

Traditional ROI: 3.31%

155 Erie Avenue

New Windsor, NY

3 beds | 2 baths | 1,192 sq.ft.

$389,000

Airbnb cash on cash: 2.99%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $2604

Traditional Rental Income: $2671

Airbnb ROI: 2.99%

Traditional ROI: 4.88%

15 Queen Street

New Windsor, NY

3 beds | 1 baths | 1,350 sq.ft.

$425,000

Airbnb cash on cash: 1.81%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $2604

Traditional Rental Income: $2443

Airbnb ROI: 1.81%

Traditional ROI: 2.97%

404 Carlton Circle

New Windsor, NY

3 beds | 3 baths | 2,146 sq.ft.

$510,000

Airbnb cash on cash: 1.23%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $2604

Traditional Rental Income: $3497

Airbnb ROI: 1.23%

Traditional ROI: 4.41%

6 Barclay Road

New Windsor, NY

3 beds | 4 baths | 2,517 sq.ft.

$499,000

Airbnb cash on cash: 0.56%

Traditional cash on cash: 5.4%

Airbnb Rental Income: $2604

Traditional Rental Income: $4238

Airbnb ROI: 0.56%

Traditional ROI: 5.4%

11 Willow Lane

New Windsor, NY

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

$437,500

Airbnb cash on cash: 1.77%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $2604

Traditional Rental Income: $2546

Airbnb ROI: 1.77%