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.

Golden Highlands Investment Property for Sale in New Windsor, NY

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

Showing 49 Golden Highlands Investment Property 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
601 Crab Apple Lane New Windsor, NY Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom townhouse nestled in the he...	3 beds \| 3 baths \| 1,673 sq.ft.	$439,999	Airbnb cash on cash: 1.02% Traditional cash on cash: 4.62% Airbnb Rental Income: $2422 Traditional Rental Income: $3312 Airbnb ROI: 1.02% Traditional ROI: 4.62%
276 Temple Hill Road #704 New Windsor, NY AS-IS SALE. Inspections are for buyer's informational purposes only. Seller will not make ...	2 beds \| 2 baths \| 1,296 sq.ft.	$310,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 4.41% Airbnb Rental Income: $1867 Traditional Rental Income: $2318 Airbnb ROI: 1.15% Traditional ROI: 4.41%
43 Lafayette Drive New Windsor, NY Whether you're looking for your first home or a smart investment opportunity, this propert...	2 beds \| 1 baths \| 715 sq.ft.	$274,900	Airbnb cash on cash: 2.72% Traditional cash on cash: 5.12% Airbnb Rental Income: $1867 Traditional Rental Income: $1989 Airbnb ROI: 2.72% Traditional ROI: 5.12%
1010 Pine View New Windsor, NY Tucked away on a private street within the desirable Forest Glen community, this tastefull...	5 beds \| 4 baths \| 4,366 sq.ft.	$850,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.72% Airbnb Rental Income: $2823 Traditional Rental Income: $4854 Airbnb ROI: -0.68% Traditional ROI: 2.72%
2041 Independence Drive New Windsor, NY Welcome to 2041 Independence Drive, a beautifully maintained extended colonial-the largest...	5 beds \| 3 baths \| 3,452 sq.ft.	$799,999	Airbnb cash on cash: -0.15% Traditional cash on cash: 2.42% Airbnb Rental Income: $2823 Traditional Rental Income: $4076 Airbnb ROI: -0.15% Traditional ROI: 2.42%
10 Oakwood Terrace #65 New Windsor, NY Welcome to this beautifully maintained 1-bedroom co-op located in the desirable Oakwood Te...	1 beds \| 1 baths \| 750 sq.ft.	$139,000	Airbnb cash on cash: -4.26% Traditional cash on cash: 4.1% Airbnb Rental Income: $970 Traditional Rental Income: $1735 Airbnb ROI: -4.26% Traditional ROI: 4.1%
60 Trafalgar Road #1 New Windsor, NY Welcome Home! Newly remodeled 1 Bed and 1 Bath apartment in Squire Village of New Windsor....	1 beds \| 1 baths \| 700 sq.ft.	$165,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 7.49% Airbnb Rental Income: $970 Traditional Rental Income: $1636 Airbnb ROI: 1.04% Traditional ROI: 7.49%
9 Benedict Lane #5-7 New Windsor, NY Income-producing multi-property asset offered at approximately an 8% cap rate with $75,900...	8 beds \| 4 baths \| N/A	$949,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 2.53% Airbnb Rental Income: $2823 Traditional Rental Income: $4761 Airbnb ROI: -0.41% Traditional ROI: 2.53%
16 McDonald Court New Windsor, NY Exceptional new construction in sought-after Meadowbrook Estates, located in the award win...	4 beds \| 3 baths \| N/A	$835,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 2.08% Airbnb Rental Income: $3238 Traditional Rental Income: $3736 Airbnb ROI: 0.5% Traditional ROI: 2.08%
70 Bethlehem Road New Windsor, NY NEW CONSTRUCTION CORNWALL CENTRAL SCHOOL DISTRICT! Nestled on a private and expansive 1.47...	4 beds \| 3 baths \| 3,098 sq.ft.	$899,999	Airbnb cash on cash: -0.11% Traditional cash on cash: 1.68% Airbnb Rental Income: $3238 Traditional Rental Income: $4011 Airbnb ROI: -0.11% Traditional ROI: 1.68%
64 Bethlehem Road New Windsor, NY Nestled in the heart of the Town of New Windsor within the Cornwall School District, this ...	4 beds \| 3 baths \| 2,668 sq.ft.	$849,999	Airbnb cash on cash: 0.03% Traditional cash on cash: 1.88% Airbnb Rental Income: $3238 Traditional Rental Income: $3978 Airbnb ROI: 0.03% Traditional ROI: 1.88%
23 Swan Hollow New Windsor, NY Discover the perfect blend of modern construction, privacy, and scenic beauty in this cust...	3 beds \| 3 baths \| 2,353 sq.ft.	$899,999	Airbnb cash on cash: -0.44% Traditional cash on cash: 1.99% Airbnb Rental Income: $2422 Traditional Rental Income: $3862 Airbnb ROI: -0.44% Traditional ROI: 1.99%
276 Temple Hill Road #1305 New Windsor, NY Welcome to Continental Manor, where comfort meets convenience in this well maintained 3-be...	3 beds \| 2 baths \| 1,512 sq.ft.	$265,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 5.74% Airbnb Rental Income: $2422 Traditional Rental Income: $2802 Airbnb ROI: 1.85% Traditional ROI: 5.74%
276 Temple Hill Road #2808 New Windsor, NY Welcome Home to this beautiful 3 bedroom, 1.5 bath end unit! Next to new everything! Washe...	3 beds \| 2 baths \| 1,530 sq.ft.	$337,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 4.69% Airbnb Rental Income: $2422 Traditional Rental Income: $2962 Airbnb ROI: 1.12% Traditional ROI: 4.69%
305 Gazebo Court New Windsor, NY This beautifully maintained 2 bedroom, 2 full bath ground-floor condo offers comfort, conv...	2 beds \| 2 baths \| 1,222 sq.ft.	$330,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.76% Airbnb Rental Income: $1867 Traditional Rental Income: $2569 Airbnb ROI: -0.12% Traditional ROI: 3.76%
3002 Molly Pitcher Drive New Windsor, NY Located in the highly sought-after Reserve neighborhood of New Windsor and within the awar...	5 beds \| 4 baths \| 3,510 sq.ft.	$850,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 2.99% Airbnb Rental Income: $2823 Traditional Rental Income: $4770 Airbnb ROI: -0.31% Traditional ROI: 2.99%
18 Coach House Court New Windsor, NY Welcome to this stunning 4-bedroom, 3-full-bath Colonial tucked away on a quiet cul-de-sac...	5 beds \| 3 baths \| 2,923 sq.ft.	$765,000	Airbnb cash on cash: 0.21% Traditional cash on cash: N/A Airbnb Rental Income: $2823 Traditional Rental Income: $0 Airbnb ROI: 0.21% Traditional ROI: N/A
3014 Patrick Henry Court #43 New Windsor, NY Meticulously maintained townhouse in the coveted "Patriot Ridge" community, tucked away on...	3 beds \| 3 baths \| 2,592 sq.ft.	$419,900	Airbnb cash on cash: 2.14% Traditional cash on cash: 6.5% Airbnb Rental Income: $2422 Traditional Rental Income: $3544 Airbnb ROI: 2.14% Traditional ROI: 6.5%
91 Myrtle Avenue New Windsor, NY **Multiple offer situation. Seller requesting highest, best and final offers 8am 4/20/2026...	3 beds \| 1 baths \| 1,056 sq.ft.	$270,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 5.62% Airbnb Rental Income: $2422 Traditional Rental Income: $2250 Airbnb ROI: 3.97% Traditional ROI: 5.62%
804 Hawthorn Way New Windsor, NY Welcome to this meticulously maintained townhouse in the sought-after community of The Gro...	3 beds \| 3 baths \| 1,910 sq.ft.	$474,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 4% Airbnb Rental Income: $2422 Traditional Rental Income: $3212 Airbnb ROI: 0.89% Traditional ROI: 4%
62 Union Avenue New Windsor, NY Welcome to 62 Union Ave in New Windsor - a beautifully renovated home that's move-in ready...	3 beds \| 2 baths \| 1,436 sq.ft.	$399,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 5.74% Airbnb Rental Income: $2422 Traditional Rental Income: $3033 Airbnb ROI: 2.52% Traditional ROI: 5.74%
1 San Giacomo Drive New Windsor, NY What an opportunity! Living in a community that has a park directly steps away from the fr...	5 beds \| 3 baths \| 1,967 sq.ft.	$565,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 4.96% Airbnb Rental Income: $2823 Traditional Rental Income: $4137 Airbnb ROI: 1.22% Traditional ROI: 4.96%
610 Mount Airy Road New Windsor, NY If you are looking for a project, and enjoy pastoral and water views, then this raised ran...	3 beds \| 2 baths \| 1,184 sq.ft.	$299,900	Airbnb cash on cash: 0.98% Traditional cash on cash: 4.1% Airbnb Rental Income: $2422 Traditional Rental Income: $2708 Airbnb ROI: 0.98% Traditional ROI: 4.1%
84 Guernsey Drive New Windsor, NY Welcome to 84 Guernsey Drive in Butterhill Estates of New Windsor, NY! This well-maintaine...	3 beds \| 3 baths \| 1,736 sq.ft.	$549,000	Airbnb cash on cash: 0.84% Traditional cash on cash: 3.59% Airbnb Rental Income: $2422 Traditional Rental Income: $3242 Airbnb ROI: 0.84% Traditional ROI: 3.59%
69 Cedar Avenue New Windsor, NY Here's your chance to grab a piece of the Fastly-Growing Orange County, presenting 69 Ceda...	3 beds \| 3 baths \| 1,350 sq.ft.	$349,999	Airbnb cash on cash: 2.1% Traditional cash on cash: 6.18% Airbnb Rental Income: $2422 Traditional Rental Income: $3170 Airbnb ROI: 2.1% Traditional ROI: 6.18%
276 TEMPLE HILL ROAD #103 New Windsor, NY This beautifully updated 2 bedroom, 1.5 bath condo is located in the much desired Continen...	2 beds \| 2 baths \| 1,176 sq.ft.	$295,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 5.45% Airbnb Rental Income: $1867 Traditional Rental Income: $2357 Airbnb ROI: 1.89% Traditional ROI: 5.45%
532 Shore Drive New Windsor, NY Welcome to the highly sought-after Beaver Dam community within the Cornwall Central School...	4 beds \| 2 baths \| 1,424 sq.ft.	$449,900	Airbnb cash on cash: 4.65% Traditional cash on cash: 7.94% Airbnb Rental Income: $3238 Traditional Rental Income: $3895 Airbnb ROI: 4.65% Traditional ROI: 7.94%
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.	$480,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 4.58% Airbnb Rental Income: $3238 Traditional Rental Income: $3607 Airbnb ROI: 2.14% Traditional ROI: 4.58%
24 Quassaick Avenue New Windsor, NY This well-maintained and updated 2-bedroom, 1-bath home is truly move-in ready. Situated o...	2 beds \| 2 baths \| 575 sq.ft.	$235,000	Airbnb cash on cash: 3.54% Traditional cash on cash: 7.46% Airbnb Rental Income: $1867 Traditional Rental Income: $2239 Airbnb ROI: 3.54% Traditional ROI: 7.46%
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.	$805,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.01% Airbnb Rental Income: $3238 Traditional Rental Income: $4098 Airbnb ROI: -0.11% Traditional ROI: 2.01%
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.	$405,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 3.17% Airbnb Rental Income: $2422 Traditional Rental Income: $2443 Airbnb ROI: 1.55% Traditional ROI: 3.17%
404 Carlton Circle New Windsor, NY Major Price Improvement. Seller Motivated! Step into a sun-filled living room and enjoy th...	3 beds \| 3 baths \| 2,146 sq.ft.	$475,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.8% Airbnb Rental Income: $2422 Traditional Rental Income: $3497 Airbnb ROI: 1.05% Traditional ROI: 4.8%
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: -0.2% Traditional cash on cash: 1.93% Airbnb Rental Income: $3238 Traditional Rental Income: $4197 Airbnb ROI: -0.2% Traditional ROI: 1.93%
400 Philo Street New Windsor, NY Welcome to this beautifully maintained 3-bedroom, 1.5-bathroom residence, ideally located ...	3 beds \| 2 baths \| 1,762 sq.ft.	$460,000	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.79% Airbnb Rental Income: $2422 Traditional Rental Income: $2910 Airbnb ROI: 1.28% Traditional ROI: 3.79%
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: 2.02% Traditional cash on cash: 6.01% Airbnb Rental Income: $2823 Traditional Rental Income: $3918 Airbnb ROI: 2.02% Traditional ROI: 6.01%
810 Blooming Grove Turnpike #88 New Windsor, NY Welcome to this spacious and sun-filled 2-bedroom, 1-bath condo offering 1,260 square feet...	2 beds \| 1 baths \| 1,260 sq.ft.	$229,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 4.58% Airbnb Rental Income: $1867 Traditional Rental Income: $2209 Airbnb ROI: 0.69% Traditional ROI: 4.58%
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.	$679,900	Airbnb cash on cash: 0.33% Traditional cash on cash: 3.06% Airbnb Rental Income: $2823 Traditional Rental Income: $3901 Airbnb ROI: 0.33% Traditional ROI: 3.06%
10 Oakwood Terrace #110 New Windsor, NY Top floor, Spacious and sun-filled 1-bedroom, 1-bath end unit co-op offering 960 square fe...	1 beds \| 1 baths \| 960 sq.ft.	$134,900	Airbnb cash on cash: -4.51% Traditional cash on cash: 4.69% Airbnb Rental Income: $970 Traditional Rental Income: $1811 Airbnb ROI: -4.51% Traditional ROI: 4.69%
1404 Hawthorn Way New Windsor, NY Price improved! Refreshed and ready for the selective buyer this lovely one owner town hom...	3 beds \| 3 baths \| 1,910 sq.ft.	$469,999	Airbnb cash on cash: -0.13% Traditional cash on cash: 3.29% Airbnb Rental Income: $2422 Traditional Rental Income: $3333 Airbnb ROI: -0.13% Traditional ROI: 3.29%
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% Traditional cash on cash: 5.19% Airbnb Rental Income: $2422 Traditional Rental Income: $3730 Airbnb ROI: 1% Traditional ROI: 5.19%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in New Windsor, NY

601 Crab Apple Lane

New Windsor, NY

3 beds | 3 baths | 1,673 sq.ft.

$439,999

Airbnb cash on cash: 1.02%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $2422

Traditional Rental Income: $3312

Airbnb ROI: 1.02%

Traditional ROI: 4.62%

276 Temple Hill Road #704

New Windsor, NY

2 beds | 2 baths | 1,296 sq.ft.

$310,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $1867

Traditional Rental Income: $2318

Airbnb ROI: 1.15%

Traditional ROI: 4.41%

43 Lafayette Drive

New Windsor, NY

2 beds | 1 baths | 715 sq.ft.

$274,900

Airbnb cash on cash: 2.72%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $1867

Traditional Rental Income: $1989

Airbnb ROI: 2.72%

Traditional ROI: 5.12%

1010 Pine View

New Windsor, NY

5 beds | 4 baths | 4,366 sq.ft.

$850,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 2.72%

Airbnb Rental Income: $2823

Traditional Rental Income: $4854

Airbnb ROI: -0.68%

Traditional ROI: 2.72%

2041 Independence Drive

New Windsor, NY

5 beds | 3 baths | 3,452 sq.ft.

$799,999

Airbnb cash on cash: -0.15%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $2823

Traditional Rental Income: $4076

Airbnb ROI: -0.15%

Traditional ROI: 2.42%

10 Oakwood Terrace #65

New Windsor, NY

1 beds | 1 baths | 750 sq.ft.

$139,000

Airbnb cash on cash: -4.26%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $970

Traditional Rental Income: $1735

Airbnb ROI: -4.26%

Traditional ROI: 4.1%

60 Trafalgar Road #1

New Windsor, NY

1 beds | 1 baths | 700 sq.ft.

$165,000

Airbnb cash on cash: 1.04%

Traditional cash on cash: 7.49%

Airbnb Rental Income: $970

Traditional Rental Income: $1636

Airbnb ROI: 1.04%

Traditional ROI: 7.49%

9 Benedict Lane #5-7

New Windsor, NY

8 beds | 4 baths | N/A

$949,000

Airbnb cash on cash: -0.41%

Traditional cash on cash: 2.53%

Airbnb Rental Income: $2823

Traditional Rental Income: $4761

Airbnb ROI: -0.41%