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
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.	$545,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 4.53% Airbnb Rental Income: $3697 Traditional Rental Income: $3814 Airbnb ROI: 2.72% Traditional ROI: 4.53%
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: -1.01% Traditional cash on cash: 2.59% Airbnb Rental Income: $2132 Traditional Rental Income: $4168 Airbnb ROI: -1.01% Traditional ROI: 2.59%
30 Cotter Road Highland, NY INVESTMENT OPPORTUNITY! Welcome to 30 Cotter Road â a unique opportunity to own a versa...	3 beds \| 2 baths \| 1,080 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.5% Airbnb Rental Income: $null Traditional Rental Income: $1958 Airbnb ROI: N/A Traditional ROI: 4.5%
87 Sterling Place Highland, NY Welcome to 87 Sterling Place in Highland, located right over the Mid Hudson Bridge. The h...	2 beds \| 3 baths \| 1,396 sq.ft.	$335,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 5.48% Airbnb Rental Income: $1805 Traditional Rental Income: $2857 Airbnb ROI: 0.58% Traditional ROI: 5.48%
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: -0.23% Traditional cash on cash: 3.55% Airbnb Rental Income: $1107 Traditional Rental Income: $1539 Airbnb ROI: -0.23% Traditional ROI: 3.55%
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: 0.72% Traditional cash on cash: 4.4% Airbnb Rental Income: $2107 Traditional Rental Income: $3120 Airbnb ROI: 0.72% Traditional ROI: 4.4%
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: 2.04% Traditional cash on cash: 4.4% Airbnb Rental Income: $2107 Traditional Rental Income: $2340 Airbnb ROI: 2.04% Traditional ROI: 4.4%
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: 1.96% Traditional cash on cash: 5% Airbnb Rental Income: $2107 Traditional Rental Income: $2508 Airbnb ROI: 1.96% Traditional ROI: 5%
16 Fair Street Highland, NY Pack your bags, you've found the one! With a little TLC this could be your "home sweet ho...	4 beds \| 2 baths \| 1,408 sq.ft.	$325,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 6.91% Airbnb Rental Income: $2132 Traditional Rental Income: $3042 Airbnb ROI: 2.15% Traditional ROI: 6.91%
290 Tuckers Corners Road Highland, NY Discover the perfect blend of comfort, convenience, and potential in this well-maintained ...	3 beds \| 2 baths \| 1,560 sq.ft.	$499,999	Airbnb cash on cash: 0.21% Traditional cash on cash: 3.28% Airbnb Rental Income: $2107 Traditional Rental Income: $3003 Airbnb ROI: 0.21% Traditional ROI: 3.28%
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: 0.7% Traditional cash on cash: 3.74% Airbnb Rental Income: $2107 Traditional Rental Income: $2480 Airbnb ROI: 0.7% Traditional ROI: 3.74%
370 N Elting Corners Road Highland, NY Tucked away on a peaceful hilltop just 7 minutes from the heart of New Paltz, this stunnin...	4 beds \| 2 baths \| 2,176 sq.ft.	$995,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 1.29% Airbnb Rental Income: $2132 Traditional Rental Income: $3360 Airbnb ROI: -0.62% Traditional ROI: 1.29%
27 Salk Drive Highland, NY Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial perfectly blending tim...	4 beds \| 3 baths \| 2,342 sq.ft.	$575,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 3.85% Airbnb Rental Income: $2132 Traditional Rental Income: $3874 Airbnb ROI: -0.41% Traditional ROI: 3.85%
224 Martin Avenue Highland, NY Welcome to this charming ranch style home featuring 3 cozy bedrooms. The primary bedroom h...	3 beds \| 2 baths \| 1,633 sq.ft.	$475,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 4.22% Airbnb Rental Income: $2107 Traditional Rental Income: $3221 Airbnb ROI: 0.5% Traditional ROI: 4.22%
21 Triangle of Clearwater Road Highland, NY 21 Clearwater Rd, Lloyd, NY 12528 - Updated Listing Description Welcome to 21 Clearwater R...	3 beds \| 2 baths \| 1,196 sq.ft.	$395,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 4.11% Airbnb Rental Income: $2107 Traditional Rental Income: $2673 Airbnb ROI: 1.12% Traditional ROI: 4.11%
17 Dogwood Knolls Highland, NY Incredible home with stunning renovations; this one of a kind raised ranch has over 2,200 ...	3 beds \| 3 baths \| 2,284 sq.ft.	$575,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 3.77% Airbnb Rental Income: $2107 Traditional Rental Income: $3585 Airbnb ROI: 0.01% Traditional ROI: 3.77%
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: 1.09% Traditional cash on cash: 6.11% Airbnb Rental Income: $2107 Traditional Rental Income: $3264 Airbnb ROI: 1.09% Traditional ROI: 6.11%
723 New Paltz Road Highland, NY First Time Ever on the Market, this wonderful 4 bedroom home! Welcome to 723 New Paltz Roa...	4 beds \| 2 baths \| 2,121 sq.ft.	$450,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 4.88% Airbnb Rental Income: $2132 Traditional Rental Income: $3420 Airbnb ROI: 0.53% Traditional ROI: 4.88%
16 Orchard Lane Highland, NY Welcome to your next home! This delightful 2-bedroom, 1-bath raised ranch is nestled in on...	2 beds \| 1 baths \| 1,090 sq.ft.	$375,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 2.73% Airbnb Rental Income: $1805 Traditional Rental Income: $2006 Airbnb ROI: 0.77% Traditional ROI: 2.73%
614 Plutarch Road Highland, NY A/O 8/3 NO TRESSPASSING Appointments are a must - camera on premises. A rare opportunity t...	3 beds \| 1 baths \| 1,434 sq.ft.	$175,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 7.21% Airbnb Rental Income: $2107 Traditional Rental Income: $2300 Airbnb ROI: 2.81% Traditional ROI: 7.21%
546 South Street Highland, NY Located in the heart of the Hudson Valley, this spacious 2,500 sq ft home in Highland blen...	5 beds \| 2 baths \| 2,500 sq.ft.	$399,900	Airbnb cash on cash: 4.6% Traditional cash on cash: 6.02% Airbnb Rental Income: $3697 Traditional Rental Income: $3423 Airbnb ROI: 4.6% Traditional ROI: 6.02%
399 New Paltz Road Highland, NY Spacious Raised Ranch with Endless Potential in Highland! Discover this large and versatil...	4 beds \| 3 baths \| 2,700 sq.ft.	$380,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 7.82% Airbnb Rental Income: $2132 Traditional Rental Income: $3995 Airbnb ROI: 1.07% Traditional ROI: 7.82%

Real Estate investment in Highland, NY

There are 22 properties for sale in the city of Highland . The median list price in Highland is $380,000 and the average price per square foot is $214. In September 2025, the average monthly cash on cash return in Highland is 4.00%. The average monthly rental income in Highland is $3,042.

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

There are 22 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 $3,042.

Your search for investment property begins and ends here

Investment Property for Sale in Highland, NY

191 Bedell Avenue

Highland, NY

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

$545,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $3697

Traditional Rental Income: $3814

Airbnb ROI: 2.72%

Traditional ROI: 4.53%

2 Fieldstone Court

Highland, NY

4 beds | 3 baths | 3,253 sq.ft.

$769,000

Airbnb cash on cash: -1.01%

Traditional cash on cash: 2.59%

Airbnb Rental Income: $2132

Traditional Rental Income: $4168

Airbnb ROI: -1.01%

Traditional ROI: 2.59%

30 Cotter Road

Highland, NY

3 beds | 2 baths | 1,080 sq.ft.

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.5%

Airbnb Rental Income: $null

Traditional Rental Income: $1958

Airbnb ROI: N/A

Traditional ROI: 4.5%

87 Sterling Place

Highland, NY

2 beds | 3 baths | 1,396 sq.ft.

$335,000

Airbnb cash on cash: 0.58%

Traditional cash on cash: 5.48%

Airbnb Rental Income: $1805

Traditional Rental Income: $2857

Airbnb ROI: 0.58%

Traditional ROI: 5.48%

534 New Paltz Road

Highland, NY

1 beds | 1 baths | 762 sq.ft.

$225,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $1107

Traditional Rental Income: $1539

Airbnb ROI: -0.23%

Traditional ROI: 3.55%

334 Pancake Hollow Road

Highland, NY

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

$450,000

Airbnb cash on cash: 0.72%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $2107

Traditional Rental Income: $3120

Airbnb ROI: 0.72%

Traditional ROI: 4.4%

283 Hawleys Corners Road

Highland, NY

3 beds | 1 baths | 1,816 sq.ft.

$349,000

Airbnb cash on cash: 2.04%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $2107

Traditional Rental Income: $2340

Airbnb ROI: 2.04%

Traditional ROI: 4.4%

37 Maple Avenue

Highland, NY

3 beds | 3 baths | 1,121 sq.ft.

$329,000

Airbnb cash on cash: 1.96%

Traditional cash on cash: 5%

Airbnb Rental Income: $2107

Traditional Rental Income: $2508

Airbnb ROI: 1.96%