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
8 Canterbury Drive Middletown, NY Welcome to one of the cul-de-sacs off Comly on Canterbury Drive. Embrace timeless charm wi...	3 beds \| 3 baths \| 1,814 sq.ft.	$815,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 1.41% Airbnb Rental Income: $8122 Traditional Rental Income: $3427 Airbnb ROI: 5.56% Traditional ROI: 1.41%
Investment Properties for Sale in Other Cities of New-york
467 Keap Street New York , NY Ainslie Tower is a ten-story, thirty-unit elevator apartment building built in 2009. Thi...	N/A beds \| N/A baths \| 65,535 sq.ft.	$27,000,000	Airbnb cash on cash: -1.39% Traditional cash on cash: -1.38% Airbnb Rental Income: $3050 Traditional Rental Income: $2749 Airbnb ROI: -1.39% Traditional ROI: -1.38%
77 Arlington Place New York , NY Presenting a wonderful opportunity in the form of a semi-detached one-family home boasting...	3 beds \| 2 baths \| 1,532 sq.ft.	$548,800	Airbnb cash on cash: 7.42% Traditional cash on cash: 4.14% Airbnb Rental Income: $5856 Traditional Rental Income: $3011 Airbnb ROI: 7.42% Traditional ROI: 4.14%
50 Bradburn Street Rochester , NY Delayed showings/negotiations. Showings to commence on 11/15/24, negotiations begin on 11/...	3 beds \| 1 baths \| 1,772 sq.ft.	$149,900	Airbnb cash on cash: 7.51% Traditional cash on cash: 7.42% Airbnb Rental Income: $2174 Traditional Rental Income: $1610 Airbnb ROI: 7.51% Traditional ROI: 7.42%
139-15 83rd Avenue #127 New York , NY Discover the perfect blend of style and convenience in this beautifully updated 1-bedroom ...	1 beds \| 1 baths \| 709 sq.ft.	$175,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 4.07% Airbnb Rental Income: $3059 Traditional Rental Income: $2261 Airbnb ROI: 4.66% Traditional ROI: 4.07%
16 Mickardan Court New York , NY Price Improved and Cheaper Than a Condo! Welcome to this charming semi-detached single-fam...	3 beds \| 3 baths \| 1,200 sq.ft.	$488,888	Airbnb cash on cash: 8.24% Traditional cash on cash: 4.4% Airbnb Rental Income: $5856 Traditional Rental Income: $2933 Airbnb ROI: 8.24% Traditional ROI: 4.4%
86 Virginia Avenue New York , NY LOCATION is Everything!!! Minutes to the Verrazano Bridge and SI Ferry, this recently reno...	5 beds \| 4 baths \| 2,190 sq.ft.	$859,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.71% Airbnb Rental Income: $null Traditional Rental Income: $3655 Airbnb ROI: N/A Traditional ROI: 2.71%
109-41 164th Street So.Jamaica , NY Welcome to this fully detached single family home located in Jamaica. It has 3 bedroom on ...	3 beds \| 3 baths \| 1,072 sq.ft.	$664,900	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.23% Airbnb Rental Income: $2086 Traditional Rental Income: $3135 Airbnb ROI: 0.8% Traditional ROI: 3.23%
217-14 133rd Road New York , NY REO- HANDYMAN SPECIAL COLONIAL BOASTS 3 BEDROOMS, LR, FDR, EIK, 2 FULL BATHS, AND FULL BAS...	3 beds \| 2 baths \| N/A	$549,000	Airbnb cash on cash: 3.85% Traditional cash on cash: 4.42% Airbnb Rental Income: $3940 Traditional Rental Income: $3388 Airbnb ROI: 3.85% Traditional ROI: 4.42%
151 Ross Avenue New York , NY LOCATION LOCATION! THIS BEAUTIFUL 2 FAMILY OFFERS 3BED 3 BATH IN MAIN UNIT, WITH AN ATTIC ...	5 beds \| 5 baths \| 1,886 sq.ft.	$878,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $4462 Airbnb ROI: N/A Traditional ROI: 3.56%
99-03 207th Street New York , NY , Additional information: Appearance:Excellent	5 beds \| 3 baths \| N/A	$1,450,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $4817 Airbnb ROI: N/A Traditional ROI: 2.16%
142-12 Hook Creek Boulevard New York , NY Welcome to this lovely and exceptionally spacious home featuring beautiful hardwood floors...	4 beds \| 3 baths \| N/A	$699,000	Airbnb cash on cash: 7.89% Traditional cash on cash: 4.83% Airbnb Rental Income: $8065 Traditional Rental Income: $4534 Airbnb ROI: 7.89% Traditional ROI: 4.83%
3229 Glennon Place New York , NY Welcome to 3229 Glennon Place, a charming single-family home in the serene neighborhood of...	2 beds \| 2 baths \| 964 sq.ft.	$559,000	Airbnb cash on cash: 4.81% Traditional cash on cash: 3.41% Airbnb Rental Income: $4530 Traditional Rental Income: $2859 Airbnb ROI: 4.81% Traditional ROI: 3.41%
80 Suffolk Road Island Park , NY Ahoy, water enthusiasts! If you've been dreaming of a waterfront escape that's as refreshi...	5 beds \| 3 baths \| 3,082 sq.ft.	$774,999	Airbnb cash on cash: 5.35% Traditional cash on cash: 3.13% Airbnb Rental Income: $7809 Traditional Rental Income: $4719 Airbnb ROI: 5.35% Traditional ROI: 3.13%
130 Delafield Lane Newburgh , NY Welcome to the Meadow Winds community! This beautiful multi-level townhouse offers 2 bedro...	2 beds \| 3 baths \| 2,206 sq.ft.	$387,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 4.86% Airbnb Rental Income: $3755 Traditional Rental Income: $3086 Airbnb ROI: 4.46% Traditional ROI: 4.86%
179 Reservoir Road Middletown , NY Welcome to the OPPORTUNITY OF A LIFETIME! This one-of-a-kind home with its one-of-a-kind y...	3 beds \| 2 baths \| 3,080 sq.ft.	$699,999	Airbnb cash on cash: 2.65% Traditional cash on cash: 2.51% Airbnb Rental Income: $4464 Traditional Rental Income: $3438 Airbnb ROI: 2.65% Traditional ROI: 2.51%

Real Estate investment in Middletown, NY

There are 1 properties for sale in the city of Middletown . The median list price in Middletown is $382,450 and the average price per square foot is $207. In January 2025, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $3,042.

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

There are 1 investment properties available for sale in Middletown.

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

The ROI for Short-Term is higher than the Long-Term in Middletown with average rental income of $4,464.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, NY

8 Canterbury Drive

Middletown, NY

3 beds | 3 baths | 1,814 sq.ft.

$815,000

Airbnb cash on cash: 5.56%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $8122

Traditional Rental Income: $3427

Airbnb ROI: 5.56%

Traditional ROI: 1.41%

Investment Properties for Sale in Other Cities of New-york

New York , NY

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

$27,000,000

Airbnb cash on cash: -1.39%

Traditional cash on cash: -1.38%

Airbnb Rental Income: $3050

Traditional Rental Income: $2749

Airbnb ROI: -1.39%

Traditional ROI: -1.38%

New York , NY

3 beds | 2 baths | 1,532 sq.ft.

$548,800

Airbnb cash on cash: 7.42%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $5856

Traditional Rental Income: $3011

Airbnb ROI: 7.42%

Traditional ROI: 4.14%

Rochester , NY

3 beds | 1 baths | 1,772 sq.ft.

$149,900

Airbnb cash on cash: 7.51%

Traditional cash on cash: 7.42%

Airbnb Rental Income: $2174

Traditional Rental Income: $1610

Airbnb ROI: 7.51%

Traditional ROI: 7.42%

New York , NY

1 beds | 1 baths | 709 sq.ft.

$175,000

Airbnb cash on cash: 4.66%

Traditional cash on cash: 4.07%

Airbnb Rental Income: $3059

Traditional Rental Income: $2261

Airbnb ROI: 4.66%

Traditional ROI: 4.07%

New York , NY

3 beds | 3 baths | 1,200 sq.ft.

$488,888

Airbnb cash on cash: 8.24%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $5856

Traditional Rental Income: $2933

Airbnb ROI: 8.24%

Traditional ROI: 4.4%

New York , NY

5 beds | 4 baths | 2,190 sq.ft.

$859,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.71%

Airbnb Rental Income: $null

Traditional Rental Income: $3655

Airbnb ROI: N/A

Traditional ROI: 2.71%

So.Jamaica , NY

3 beds | 3 baths | 1,072 sq.ft.

$664,900

Airbnb cash on cash: 0.8%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $2086

Traditional Rental Income: $3135

Airbnb ROI: 0.8%

Traditional ROI: 3.23%

New York , NY

3 beds | 2 baths | N/A

$549,000

Airbnb cash on cash: 3.85%

Traditional cash on cash: 4.42%