Real Estate Investment Properties for Sale in Highland, NY

Looking for investment property in Highland, NY with high ROI ?

Explore a variety of short-term homes & houses in Highland, NY. Invest wisely with VRBO & Highland, NY 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 Highland, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
22 Woodside Place Highland, NY Welcome to 22 Woodside Place, a beautifully updated 2-bedroom home full of charm and moder...	2 beds \| 1 baths \| 1,336 sq.ft.	$299,999	Airbnb cash on cash: 0.27% Traditional cash on cash: 4.38% Airbnb Rental Income: $1479 Traditional Rental Income: $2205 Airbnb ROI: 0.27% Traditional ROI: 4.38%
98 North Road Highland, NY This charming 1900 farmhouse in Highland, New York, offers a comfortable and spacious livi...	4 beds \| 2 baths \| 2,640 sq.ft.	$550,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 3.56% Airbnb Rental Income: $2956 Traditional Rental Income: $3302 Airbnb ROI: 1.56% Traditional ROI: 3.56%
534 New Paltz Road Highland, NY Move-in Ready Gem-Perfect for Easy Living in Highland, NY Step into this completely renova...	1 beds \| 1 baths \| 762 sq.ft.	$225,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 3.55% Airbnb Rental Income: $1466 Traditional Rental Income: $1539 Airbnb ROI: 1.17% Traditional ROI: 3.55%
191 Bedell Avenue Highland, NY Welcome to 191 Bedell Ave in Highland, a move-in ready gem blending classic charm with mod...	5 beds \| 3 baths \| 2,024 sq.ft.	$525,000	Airbnb cash on cash: 2.82% Traditional cash on cash: 4.74% Airbnb Rental Income: $3674 Traditional Rental Income: $3814 Airbnb ROI: 2.82% Traditional ROI: 4.74%
334 Pancake Hollow Road Highland, NY With 3 bedrooms, 2 full bathrooms, and 2,715 square feet of flexible living space, this tu...	3 beds \| 2 baths \| 2,715 sq.ft.	$450,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 4.4% Airbnb Rental Income: $2187 Traditional Rental Income: $3120 Airbnb ROI: 0.88% Traditional ROI: 4.4%
1 Janine Place Highland, NY Just 90 minutes from New York City, this extraordinary turnkey farmhouse has been complete...	4 beds \| 3 baths \| 2,600 sq.ft.	$899,999	Airbnb cash on cash: 0.25% Traditional cash on cash: 2.16% Airbnb Rental Income: $2956 Traditional Rental Income: $3875 Airbnb ROI: 0.25% Traditional ROI: 2.16%
41 Penny Lane Highland, NY Welcome to 41 Penny Lane, this ranch style home is situated on a quiet dead-end road named...	3 beds \| 3 baths \| 1,844 sq.ft.	$479,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 4.33% Airbnb Rental Income: $2187 Traditional Rental Income: $3484 Airbnb ROI: 0.2% Traditional ROI: 4.33%
123 Vineyard Avenue Highland, NY Charming 1900s Home with Character and Versatility! Step into timeless elegance with this ...	4 beds \| 2 baths \| 2,368 sq.ft.	$550,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 3.36% Airbnb Rental Income: $2956 Traditional Rental Income: $3374 Airbnb ROI: 1.22% Traditional ROI: 3.36%
2 Fieldstone Court Highland, NY Stunning colonial with contemporary flair gem boasts 4 large spacious bedrooms and 2.5 lux...	4 beds \| 3 baths \| 3,253 sq.ft.	$769,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 2.59% Airbnb Rental Income: $2956 Traditional Rental Income: $4168 Airbnb ROI: -0.06% Traditional ROI: 2.59%
37 Maple Avenue Highland, NY Freshly redone, Colonial style house 1,000 feet to the Hudson & Highland Landing Park. The...	3 beds \| 3 baths \| 1,121 sq.ft.	$329,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 5% Airbnb Rental Income: $2187 Traditional Rental Income: $2508 Airbnb ROI: 2.18% Traditional ROI: 5%
39 Sunnybrook Circle Highland, NY Move right in to this bright and refreshing 3 bedroom townhouse with many new upgrades! Br...	3 beds \| N/A baths \| 1,220 sq.ft.	$315,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 4.9% Airbnb Rental Income: $2187 Traditional Rental Income: $2416 Airbnb ROI: 2.26% Traditional ROI: 4.9%
422 Gregory Court Highland, NY TRULY NOTHING TO DO BUT MOVE IN! Welcome to this meticulously maintained upper-level end u...	2 beds \| 2 baths \| 1,027 sq.ft.	$315,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 3.89% Airbnb Rental Income: $1479 Traditional Rental Income: $2314 Airbnb ROI: -0.4% Traditional ROI: 3.89%
38 Sunny Brook Circle Highland, NY Move-In Ready 3 Bedroom Townhouse in Highpoint! Move right into this beautifully updated ...	3 beds \| 2 baths \| 1,220 sq.ft.	$319,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.74% Airbnb Rental Income: $2187 Traditional Rental Income: $2480 Airbnb ROI: 0.92% Traditional ROI: 3.74%
224 Martin Avenue Highland, NY Welcome to this charming ranch style home featuring 3 cozy bedrooms. The primary bedroom h...	1 beds \| 1.5 baths \| 1,633 sq.ft.	$475,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 4.22% Airbnb Rental Income: $2187 Traditional Rental Income: $3221 Airbnb ROI: 0.65% Traditional ROI: 4.22%
59 South Street Highland, NY Charming 1900 Two-Story Farmhouse with Vintage Character... Step into timeless charm with ...	2 beds \| 1 baths \| 1,365 sq.ft.	$425,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 2.28% Airbnb Rental Income: $1479 Traditional Rental Income: $2145 Airbnb ROI: -0.49% Traditional ROI: 2.28%
2 Cambridge Court Highland, NY Offering a beautifully maintained 3-bedroom, 2.5-bathroom townhouse with garage in a highl...	3 beds \| 3 baths \| 1,808 sq.ft.	$360,000	Airbnb cash on cash: 1.29% Traditional cash on cash: 6.11% Airbnb Rental Income: $2187 Traditional Rental Income: $3264 Airbnb ROI: 1.29% Traditional ROI: 6.11%
283 Hawleys Corners Road Highland, NY Nestled on a quiet country road in Highland, this inviting old-style home offers peaceful ...	3 beds \| 1 baths \| 1,816 sq.ft.	$349,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 4.4% Airbnb Rental Income: $2187 Traditional Rental Income: $2340 Airbnb ROI: 2.25% Traditional ROI: 4.4%
365 Crescent Avenue Highland, NY Welcome to this charming and beautifully updated home, nestled in a spacious corner lot in...	3 beds \| 1 baths \| 1,372 sq.ft.	$329,999	Airbnb cash on cash: 1.99% Traditional cash on cash: 3.94% Airbnb Rental Income: $2187 Traditional Rental Income: $2238 Airbnb ROI: 1.99% Traditional ROI: 3.94%
4 Salk Drive Highland, NY Welcome Home to Comfort, Style & Mountain Views This beautifully renovated split-level hom...	3 beds \| 2 baths \| 1,934 sq.ft.	$399,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 4.86% Airbnb Rental Income: $2187 Traditional Rental Income: $3142 Airbnb ROI: 0.83% Traditional ROI: 4.86%
39 Sunny Brook Circle Highland, NY Move right in to this bright and refreshing 3 bedroom townhouse with many new upgrades! Br...	3 beds \| 2 baths \| 1,220 sq.ft.	$315,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 4.19% Airbnb Rental Income: $2187 Traditional Rental Income: $2567 Airbnb ROI: 1.04% Traditional ROI: 4.19%

Real Estate investment in Highland, NY

There are 20 properties for sale in the city of Highland . The median list price in Highland is $360,000 and the average price per square foot is $207. In October 2025, the average monthly cash on cash return in Highland is 4.00%. The average monthly rental income in Highland is $2,638.

Highland, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 20 investment properties available for sale in Highland.

In 2025, the best neighborhood to buy investment property is Highland.

The ROI for Long-Term is higher than the Short-Term in Highland with average rental income of $2,638.

Your search for investment property begins and ends here

Investment Property for Sale in Highland, NY

22 Woodside Place

Highland, NY

2 beds | 1 baths | 1,336 sq.ft.

$299,999

Airbnb cash on cash: 0.27%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $1479

Traditional Rental Income: $2205

Airbnb ROI: 0.27%

Traditional ROI: 4.38%

98 North Road

Highland, NY

4 beds | 2 baths | 2,640 sq.ft.

$550,000

Airbnb cash on cash: 1.56%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $2956

Traditional Rental Income: $3302

Airbnb ROI: 1.56%

Traditional ROI: 3.56%

534 New Paltz Road

Highland, NY

1 beds | 1 baths | 762 sq.ft.

$225,000

Airbnb cash on cash: 1.17%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $1466

Traditional Rental Income: $1539

Airbnb ROI: 1.17%

Traditional ROI: 3.55%

191 Bedell Avenue

Highland, NY

5 beds | 3 baths | 2,024 sq.ft.

$525,000

Airbnb cash on cash: 2.82%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $3674

Traditional Rental Income: $3814

Airbnb ROI: 2.82%

Traditional ROI: 4.74%

334 Pancake Hollow Road

Highland, NY

3 beds | 2 baths | 2,715 sq.ft.

$450,000

Airbnb cash on cash: 0.88%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $2187

Traditional Rental Income: $3120

Airbnb ROI: 0.88%

Traditional ROI: 4.4%

1 Janine Place

Highland, NY

4 beds | 3 baths | 2,600 sq.ft.

$899,999

Airbnb cash on cash: 0.25%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $2956

Traditional Rental Income: $3875

Airbnb ROI: 0.25%

Traditional ROI: 2.16%

41 Penny Lane

Highland, NY

3 beds | 3 baths | 1,844 sq.ft.

$479,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $2187

Traditional Rental Income: $3484

Airbnb ROI: 0.2%

Traditional ROI: 4.33%

123 Vineyard Avenue

Highland, NY

4 beds | 2 baths | 2,368 sq.ft.

$550,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $2956

Traditional Rental Income: $3374

Airbnb ROI: 1.22%