Real Estate Investment Properties for Sale in Middletown, NY

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
669 Mountain Rd Middletown, NY 669 Mountain Rd, Middletown, NY 10940 \| Single Family Residential	6 beds \| 3 baths \| 2,948 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.54% Airbnb Rental Income: $null Traditional Rental Income: $4154 Airbnb ROI: N/A Traditional ROI: 4.54%
32 Dudley Lane Middletown, NY All you need is a moving van! Move right into this beautifully renovated 3-bedroom Nantuck...	3 beds \| 2 baths \| 1,984 sq.ft.	$419,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 5.13% Airbnb Rental Income: $1260 Traditional Rental Income: $3138 Airbnb ROI: -0.67% Traditional ROI: 5.13%
2478 Mt Hope Rd Middletown, NY Welcome to this beautifully maintained contemporary bi-level nestled in the Minisink Valle...	3 beds \| 3 baths \| 2,096 sq.ft.	$550,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 4.04% Airbnb Rental Income: $1260 Traditional Rental Income: $3515 Airbnb ROI: -1.13% Traditional ROI: 4.04%
Investment Properties for Sale in Other Cities of New-york
467 Keap Street New York , NY Ten-story mixed-use elevator building built in 2009 29 residential lofts with 20' ceiling...	N/A beds \| N/A baths \| 65,535 sq.ft.	$24,000,000	Airbnb cash on cash: -1.53% Traditional cash on cash: -1.43% Airbnb Rental Income: $705 Traditional Rental Income: $2749 Airbnb ROI: -1.53% Traditional ROI: -1.43%
15 Brookscrest Way Rochester , NY Welcome to 15 Brookscrest Way, a newer build (2013) located in a highly desirable area in ...	3 beds \| 3 baths \| 1,562 sq.ft.	$319,900	Airbnb cash on cash: -0.93% Traditional cash on cash: 5.05% Airbnb Rental Income: $1119 Traditional Rental Income: $2544 Airbnb ROI: -0.93% Traditional ROI: 5.05%
33 N Plymouth Avenue Rochester , NY Welcome to 33 N Plymouth Avenue-NOT A CONDO- NO HOA. an exceptional townhouse offering the...	4 beds \| 4 baths \| 1,796 sq.ft.	$249,900	Airbnb cash on cash: -0.22% Traditional cash on cash: 6.83% Airbnb Rental Income: $1498 Traditional Rental Income: $2722 Airbnb ROI: -0.22% Traditional ROI: 6.83%
842 Flower City Park Rochester , NY Another Rockin' Rochester Property!!! Beautiful Maplewood single-family home offering 3 be...	3 beds \| 2 baths \| 1,300 sq.ft.	$99,900	Airbnb cash on cash: 3.08% Traditional cash on cash: 8.52% Airbnb Rental Income: $1183 Traditional Rental Income: $1325 Airbnb ROI: 3.08% Traditional ROI: 8.52%
1570 Prospect Place #2 New York , NY Welcome to this beautifully maintained 2-bedroom 2-bath condo at 1570 Prospect Place in th...	2 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 0.91% Airbnb Rental Income: $2278 Traditional Rental Income: $2905 Airbnb ROI: -1.32% Traditional ROI: 0.91%
563 Glenmore Ave New York , NY Live. Work. Earn. Repeat. This is the kind of opportunity that rarely hits the market-a hi...	N/A beds \| N/A baths \| 2,400 sq.ft.	$1,350,000	Airbnb cash on cash: 0.3% Traditional cash on cash: 1.75% Airbnb Rental Income: $2549 Traditional Rental Income: $3753 Airbnb ROI: 0.3% Traditional ROI: 1.75%
1633 E 91st St New York , NY 1633 E 91st St, New York, NY 11236 \| Single Family Residential	3 beds \| 3 baths \| 1,216 sq.ft.	$750,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 2.46% Airbnb Rental Income: $2727 Traditional Rental Income: $3703 Airbnb ROI: 0.14% Traditional ROI: 2.46%
123 Avenue J New York , NY Exceptional Opportunity - Single-Family Home in Prime Location Presenting the most competi...	4 beds \| 2 baths \| 1,950 sq.ft.	$1,659,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 0.47% Airbnb Rental Income: $2278 Traditional Rental Income: $2880 Airbnb ROI: -0.29% Traditional ROI: 0.47%
123 Rounds Ave Buffalo , NY 123 Rounds Ave, Buffalo, NY 14215 \| Single Family Residential	4 beds \| 1 baths \| 1,476 sq.ft.	$179,123	Airbnb cash on cash: 0.68% Traditional cash on cash: 5.72% Airbnb Rental Income: $1027 Traditional Rental Income: $1526 Airbnb ROI: 0.68% Traditional ROI: 5.72%
2410 Grand Ave New York , NY 2410 Grand Ave, New York, NY 10468 \| Single Family Residential	4 beds \| 1 baths \| 1,710 sq.ft.	$750,000	Airbnb cash on cash: 6.97% Traditional cash on cash: 1.9% Airbnb Rental Income: $8454 Traditional Rental Income: $3313 Airbnb ROI: 6.97% Traditional ROI: 1.9%
61-41 Maspeth Ave New York , NY Welcome to this stunning, fully detached single-family home in the heart of Maspeth, Queen...	2 beds \| 2 baths \| 1,000 sq.ft.	$699,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 2.04% Airbnb Rental Income: $2859 Traditional Rental Income: $2847 Airbnb ROI: 1.04% Traditional ROI: 2.04%
140-07 68th Dr New York , NY Beautiful 3br house located in the heart of Kew Gardens Hills near all transportation and ...	3 beds \| 2 baths \| 1,296 sq.ft.	$997,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 2.25% Airbnb Rental Income: $2413 Traditional Rental Income: $3728 Airbnb ROI: 0.2% Traditional ROI: 2.25%
3034 Brighton 1 St #5 New York , NY Prime Brighton Beach Condominium! Discover this bright and spacious 2-bedroom, 2-bathroom ...	2 beds \| 2 baths \| 950 sq.ft.	$579,998	Airbnb cash on cash: 0.26% Traditional cash on cash: 3.07% Airbnb Rental Income: $2020 Traditional Rental Income: $3014 Airbnb ROI: 0.26% Traditional ROI: 3.07%
109 Madsen Avenue New York , NY Modern 2-Family Home in Tottenville - Built in 2015! Welcome to this beautiful and spaciou...	5 beds \| 5 baths \| 2,604 sq.ft.	$1,349,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.94% Airbnb Rental Income: $null Traditional Rental Income: $4805 Airbnb ROI: N/A Traditional ROI: 1.94%
1787 Randall Avenue New York , NY Welcome to 1787 Randall Avenue in Soundview, Bronx! This beautifully maintained detached s...	4 beds \| 2 baths \| 1,800 sq.ft.	$815,000	Airbnb cash on cash: 7.35% Traditional cash on cash: 2.55% Airbnb Rental Income: $8530 Traditional Rental Income: $3274 Airbnb ROI: 7.35% Traditional ROI: 2.55%

Real Estate investment in Middletown, NY

There are 3 properties for sale in the city of Middletown . The median list price in Middletown is $439,990 and the average price per square foot is $212. In May 2026, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $2,901.

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

There are 3 investment properties available for sale in Middletown.

In 2026, the best neighborhood to buy investment property is Middletown.

The ROI for Long-Term is higher than the Short-Term in Middletown with average rental income of $2,901.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, NY

669 Mountain Rd

Middletown, NY

6 beds | 3 baths | 2,948 sq.ft.

$599,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.54%

Airbnb Rental Income: $null

Traditional Rental Income: $4154

Airbnb ROI: N/A

Traditional ROI: 4.54%

32 Dudley Lane

Middletown, NY

3 beds | 2 baths | 1,984 sq.ft.

$419,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $1260

Traditional Rental Income: $3138

Airbnb ROI: -0.67%

Traditional ROI: 5.13%

2478 Mt Hope Rd

Middletown, NY

3 beds | 3 baths | 2,096 sq.ft.

$550,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $1260

Traditional Rental Income: $3515

Airbnb ROI: -1.13%

Traditional ROI: 4.04%

Investment Properties for Sale in Other Cities of New-york

New York , NY

N/A beds | N/A baths | 65,535 sq.ft.

$24,000,000

Airbnb cash on cash: -1.53%

Traditional cash on cash: -1.43%

Airbnb Rental Income: $705

Traditional Rental Income: $2749

Airbnb ROI: -1.53%

Traditional ROI: -1.43%

Rochester , NY

3 beds | 3 baths | 1,562 sq.ft.

$319,900

Airbnb cash on cash: -0.93%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $1119

Traditional Rental Income: $2544

Airbnb ROI: -0.93%

Traditional ROI: 5.05%

Rochester , NY

4 beds | 4 baths | 1,796 sq.ft.

$249,900

Airbnb cash on cash: -0.22%

Traditional cash on cash: 6.83%

Airbnb Rental Income: $1498

Traditional Rental Income: $2722

Airbnb ROI: -0.22%

Traditional ROI: 6.83%

Rochester , NY

3 beds | 2 baths | 1,300 sq.ft.

$99,900

Airbnb cash on cash: 3.08%

Traditional cash on cash: 8.52%

Airbnb Rental Income: $1183

Traditional Rental Income: $1325

Airbnb ROI: 3.08%

Traditional ROI: 8.52%

New York , NY

2 beds | 2 baths | N/A

$575,000

Airbnb cash on cash: -1.32%

Traditional cash on cash: 0.91%

Airbnb Rental Income: $2278

Traditional Rental Income: $2905

Airbnb ROI: -1.32%

Traditional ROI: 0.91%

New York , NY

N/A beds | N/A baths | 2,400 sq.ft.

$1,350,000