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
31 Bendlin Ln Middletown, NY Situated on its own road in the sought after Minisink Valley School District, this 3 bedro...	3 beds \| 2 baths \| 2,024 sq.ft.	$529,999	Airbnb cash on cash: -0.33% Traditional cash on cash: 4.08% Airbnb Rental Income: $1592 Traditional Rental Income: $3325 Airbnb ROI: -0.33% Traditional ROI: 4.08%
179 Reservoir Rd Middletown, NY Warmth, comfort & space in the Hudson Valley. Welcome home to this spacious Colonial on 2....	3 beds \| 2 baths \| 3,080 sq.ft.	$550,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 3.11% Airbnb Rental Income: $1592 Traditional Rental Income: $3438 Airbnb ROI: -0.99% Traditional ROI: 3.11%
5 Kendal Ln Middletown, NY Modern Comfort & Lake Access - The Best of Waters Edge! Welcome to this beautifully mainta...	2 beds \| 2 baths \| 1,241 sq.ft.	$337,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 6.22% Airbnb Rental Income: $1479 Traditional Rental Income: $2651 Airbnb ROI: 1.08% Traditional ROI: 6.22%
5 Oak Ridge Rd Middletown, NY Built in 2020, this spacious 2,392 sq ft home offers 4 bedrooms, 3 full bathrooms, and a 2...	4 beds \| 3 baths \| 2,392 sq.ft.	$563,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.81% Airbnb Rental Income: $2881 Traditional Rental Income: $3865 Airbnb ROI: 0.79% Traditional ROI: 3.81%
217-219 Highland Ave Middletown, NY Spacious and charming 3-bedroom, 2.5-bath home featuring a welcoming wraparound porch and ...	3 beds \| 2 baths \| 2,228 sq.ft.	$479,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 5.12% Airbnb Rental Income: $1592 Traditional Rental Income: $3651 Airbnb ROI: -0.49% Traditional ROI: 5.12%
568 County Route 49 #2C Middletown, NY Privately set in a quiet and intimate four-unit HOA community, this bright and welcoming h...	3 beds \| 2 baths \| 1,593 sq.ft.	$399,900	Airbnb cash on cash: -1.07% Traditional cash on cash: 4.06% Airbnb Rental Income: $1592 Traditional Rental Income: $3061 Airbnb ROI: -1.07% Traditional ROI: 4.06%
15 Kendal Ln Middletown, NY Beautifully maintained end-unit townhouse in the highly desirable Water's Edge community! ...	2 beds \| 2 baths \| 1,241 sq.ft.	$349,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 4.78% Airbnb Rental Income: $1479 Traditional Rental Income: $2540 Airbnb ROI: 0.21% Traditional ROI: 4.78%
512 County Route 49 Middletown, NY Welcome to this stunning, meticulously maintained Chesterfield Colonial offering breathtak...	4 beds \| 2 baths \| 2,906 sq.ft.	$699,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 2.97% Airbnb Rental Income: $2881 Traditional Rental Income: $3963 Airbnb ROI: 0.47% Traditional ROI: 2.97%
129 Concord Ln Middletown, NY An exceptional opportunity for homeowners and savvy investors, this sun-drenched, southeas...	2 beds \| 1 baths \| 1,230 sq.ft.	$259,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 7.7% Airbnb Rental Income: $1479 Traditional Rental Income: $2626 Airbnb ROI: 1.23% Traditional ROI: 7.7%
57 Boorman Rd Middletown, NY Renovated Dutch Colonial on 5+ private acres in the Minisink school district, just minutes...	3 beds \| 3 baths \| 2,074 sq.ft.	$425,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 4.4% Airbnb Rental Income: $1592 Traditional Rental Income: $2968 Airbnb ROI: -0.2% Traditional ROI: 4.4%
83 Deer Ct Dr Middletown, NY Beautifully renovated 3-bedroom, 2.5-bathroom, 1-car garage, two-story townhouse located i...	3 beds \| 2 baths \| 1,919 sq.ft.	$399,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 5.25% Airbnb Rental Income: $1592 Traditional Rental Income: $3329 Airbnb ROI: -0.6% Traditional ROI: 5.25%
59 Woodside Knolls Dr Middletown, NY Welcome home to this impeccably maintained, tri-level townhouse nestled in the heart of th...	3 beds \| 2 baths \| 2,427 sq.ft.	$489,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 4.52% Airbnb Rental Income: $1592 Traditional Rental Income: $3656 Airbnb ROI: -0.99% Traditional ROI: 4.52%
89 Prince St Middletown, NY There is a particular kind of quiet that arrives when a place becomes yours. The last box ...	2 beds \| 1 baths \| 1,008 sq.ft.	$329,900	Airbnb cash on cash: 0.07% Traditional cash on cash: 5.28% Airbnb Rental Income: $1479 Traditional Rental Income: $2660 Airbnb ROI: 0.07% Traditional ROI: 5.28%
36 Wallkill Avenue Middletown, NY Excellent mixed-use investment opportunity! Conveniently located on a high-visibility corn...	N/A beds \| N/A baths \| N/A	$550,000	Airbnb cash on cash: -2.69% Traditional cash on cash: 2.21% Airbnb Rental Income: $441 Traditional Rental Income: $2700 Airbnb ROI: -2.69% Traditional ROI: 2.21%
488 Tally Ho Rd Middletown, NY A charming 1940 bungalow located in the highly desirable Minisink Valley School District, ...	1 beds \| 1 baths \| 748 sq.ft.	$150,000	Airbnb cash on cash: -1.61% Traditional cash on cash: 6.07% Airbnb Rental Income: $560 Traditional Rental Income: $1558 Airbnb ROI: -1.61% Traditional ROI: 6.07%
60 Peach Pl Middletown, NY Welcome to Swan Village Estates conveniently located just minutes from Highways, stores an...	3 beds \| 3 baths \| 2,041 sq.ft.	$435,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 5.51% Airbnb Rental Income: $1592 Traditional Rental Income: $3560 Airbnb ROI: -0.44% Traditional ROI: 5.51%
1 Chestnut St Middletown, NY Beautifully renovated 3 bedroom 1 bathroom, everything is brand new, electrical, plumbing ...	3 beds \| 1 baths \| 1,100 sq.ft.	$375,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.55% Airbnb Rental Income: $1592 Traditional Rental Income: $2260 Airbnb ROI: 0.5% Traditional ROI: 3.55%
255 Howells Rd Middletown, NY Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom,...	5 beds \| 4 baths \| 4,200 sq.ft.	$899,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 4.72% Airbnb Rental Income: $2221 Traditional Rental Income: $5869 Airbnb ROI: -0.31% Traditional ROI: 4.72%
2 S Aspen Rd Middletown, NY Say hello to possibility! A Middletown townhouse with space, flexibility, and room to make...	3 beds \| 1 baths \| 1,884 sq.ft.	$299,900	Airbnb cash on cash: 0.52% Traditional cash on cash: 7.25% Airbnb Rental Income: $1592 Traditional Rental Income: $3039 Airbnb ROI: 0.52% Traditional ROI: 7.25%
744 Mt Hope Rd Middletown, NY Welcome to this stunning new Colonial home, currently under construction and set on approx...	4 beds \| 3 baths \| 2,400 sq.ft.	$609,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.59% Airbnb Rental Income: $2881 Traditional Rental Income: $3943 Airbnb ROI: 0.64% Traditional ROI: 3.59%
8 Green Ct Middletown, NY Welcome to this well-maintained 3-level townhome in The Fairways, a gated community conven...	3 beds \| 2 baths \| 2,548 sq.ft.	$625,000	Airbnb cash on cash: -1.31% Traditional cash on cash: 2.8% Airbnb Rental Income: $1592 Traditional Rental Income: $3533 Airbnb ROI: -1.31% Traditional ROI: 2.8%
13 Forest Ave Middletown, NY Fresh updates. New improvements. New opportunity. 13 Forest Avenue is officially back on t...	3 beds \| 2 baths \| 1,748 sq.ft.	$399,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 4.54% Airbnb Rental Income: $1592 Traditional Rental Income: $3013 Airbnb ROI: 0.08% Traditional ROI: 4.54%
238 S Centerville Rd Middletown, NY Spacious Country Retreat on 22.6 Acres in Minisink Valley School District This exceptional...	5 beds \| 2 baths \| 3,764 sq.ft.	$834,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 2.87% Airbnb Rental Income: $2221 Traditional Rental Income: $4257 Airbnb ROI: -0.43% Traditional ROI: 2.87%
2078 Route 6 Middletown, NY Welcome to this beautifully maintained contemporary bi-level home set on 2.2 private acres...	3 beds \| 3 baths \| 1,332 sq.ft.	$530,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 2.84% Airbnb Rental Income: $1592 Traditional Rental Income: $2958 Airbnb ROI: -0.64% Traditional ROI: 2.84%
11 Philcox Rd Middletown, NY Rare opportunity to own two homes next door to each other in the Pine Bush School District...	2 beds \| 1 baths \| 802 sq.ft.	$250,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 6.2% Airbnb Rental Income: $1479 Traditional Rental Income: $2106 Airbnb ROI: 1.87% Traditional ROI: 6.2%
1 Hulse St Middletown, NY "NEW CONSTRUCTION!" Stunning corner-lot home in a calm suburban setting with beautiful mou...	4 beds \| 2 baths \| 2,388 sq.ft.	$499,000	Airbnb cash on cash: 1.61% Traditional cash on cash: 5.15% Airbnb Rental Income: $2881 Traditional Rental Income: $3948 Airbnb ROI: 1.61% Traditional ROI: 5.15%
35 Dogwood Dr Middletown, NY Just pack your bags and move in. Spacious, Comfortable and Cozy 5 bedroom 1 family house f...	5 beds \| 2 baths \| 1,911 sq.ft.	$530,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 4.5% Airbnb Rental Income: $2221 Traditional Rental Income: $3844 Airbnb ROI: 0.25% Traditional ROI: 4.5%
1 High Ridge Ln Middletown, NY Welcome to refined, low maintenance living in one of Middletown's most sought after gated ...	3 beds \| 2 baths \| 2,084 sq.ft.	$469,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 4.89% Airbnb Rental Income: $1592 Traditional Rental Income: $3276 Airbnb ROI: 0.18% Traditional ROI: 4.89%
65 Maureen Dr Middletown, NY Welcome to the perfect place to purchase your home in the highly sought-after Minisink Val...	3 beds \| 2 baths \| 2,200 sq.ft.	$499,900	Airbnb cash on cash: -0.59% Traditional cash on cash: 4.23% Airbnb Rental Income: $1592 Traditional Rental Income: $3388 Airbnb ROI: -0.59% Traditional ROI: 4.23%
15 N Aspen Rd Middletown, NY NO HOA FEES! LOW TAXES!! Welcome to easy, effortless living in this turnkey, move-in ready...	2 beds \| 1 baths \| 1,144 sq.ft.	$299,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 5.35% Airbnb Rental Income: $1479 Traditional Rental Income: $2465 Airbnb ROI: 0.75% Traditional ROI: 5.35%
22 Atwood Dr Middletown, NY Coming Soon! Beautiful 3 BR, 2.5 baths.	3 beds \| 2 baths \| 1,723 sq.ft.	$484,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 4.59% Airbnb Rental Income: $1592 Traditional Rental Income: $3301 Airbnb ROI: -0.33% Traditional ROI: 4.59%
6 Charlotte Mews Middletown, NY New renovation, New split air conditioner,New floor ,NEW painting, New toilet on the first...	3 beds \| 2 baths \| 1,413 sq.ft.	$360,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 5.55% Airbnb Rental Income: $1592 Traditional Rental Income: $2854 Airbnb ROI: 0.61% Traditional ROI: 5.55%
571 Route 17m Middletown, NY Steeped in character and timeless appeal, this 1930 Colonial invites you in with its strik...	4 beds \| 2 baths \| 3,340 sq.ft.	$699,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 5.5% Airbnb Rental Income: $2881 Traditional Rental Income: $5122 Airbnb ROI: 1.03% Traditional ROI: 5.5%
66 Deer Ct Dr Middletown, NY Well-maintained 2-bedroom, 2-bath condo in the Deer Run Community with an open layout and ...	2 beds \| 2 baths \| 1,146 sq.ft.	$278,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 6.46% Airbnb Rental Income: $1479 Traditional Rental Income: $2440 Airbnb ROI: 1.26% Traditional ROI: 6.46%
430 Kirbytown Rd Middletown, NY PRIVATE ONE OF A KIND RANCH!! 16 Acres! One Level Living! 4 Bedrooms! 2 1/2 Bathrooms! 2 C...	4 beds \| 2 baths \| 2,774 sq.ft.	$1,600,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 0.92% Airbnb Rental Income: $2881 Traditional Rental Income: $3917 Airbnb ROI: -0.23% Traditional ROI: 0.92%
20 John St Middletown, NY For Sale: Income-Producing Mixed-Use Building in Prime Downtown Middletown Take advantage ...	3 beds \| 3 baths \| 5,157 sq.ft.	$575,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.75% Airbnb Rental Income: $1592 Traditional Rental Income: $3434 Airbnb ROI: -0.53% Traditional ROI: 3.75%
45 Randall Hts Middletown, NY PRESIDENTIAL HEIGHTS welcomes you to make this LUXURY CONTEMPORARY home yours today! Set i...	3 beds \| 2 baths \| 2,053 sq.ft.	$549,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 3.8% Airbnb Rental Income: $1592 Traditional Rental Income: $3516 Airbnb ROI: -0.63% Traditional ROI: 3.8%
153 Ridgewood Ave Middletown, NY Welcome to 153 Ridgewood Avenue, a beautifully maintained 2021 built ranch offering the ea...	3 beds \| 2 baths \| 1,577 sq.ft.	$450,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 4.44% Airbnb Rental Income: $1592 Traditional Rental Income: $3091 Airbnb ROI: -0.19% Traditional ROI: 4.44%
29 Murray Rd Middletown, NY 3 PRIVATE ACRES + ULTIMATE VERSATILITY + POSSIBLE INCOME POTENTIAL = A RARE MIDDLETOWN OPP...	5 beds \| 3 baths \| 2,202 sq.ft.	$555,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 4.27% Airbnb Rental Income: $2221 Traditional Rental Income: $3738 Airbnb ROI: 0.27% Traditional ROI: 4.27%
81 Silver Lake Sctn Rd Middletown, NY Experience modern living in this newly built 3-bedroom, 2.5-bath home designed with comfor...	3 beds \| 2 baths \| 1,660 sq.ft.	$499,999	Airbnb cash on cash: 0.12% Traditional cash on cash: 4.04% Airbnb Rental Income: $1592 Traditional Rental Income: $3333 Airbnb ROI: 0.12% Traditional ROI: 4.04%

Real Estate investment in Middletown, NY

There are 163 properties for sale in the city of Middletown . The median list price in Middletown is $374,776 and the average price per square foot is $183. In October 2026, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $3,091.

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

There are 163 investment properties available for sale in Middletown.

In 2026, 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 $1,592.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, NY

31 Bendlin Ln

Middletown, NY

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

$529,999

Airbnb cash on cash: -0.33%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $1592

Traditional Rental Income: $3325

Airbnb ROI: -0.33%

Traditional ROI: 4.08%

179 Reservoir Rd

Middletown, NY

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

$550,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: 3.11%

Airbnb Rental Income: $1592

Traditional Rental Income: $3438

Airbnb ROI: -0.99%

Traditional ROI: 3.11%

5 Kendal Ln

Middletown, NY

2 beds | 2 baths | 1,241 sq.ft.

$337,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $1479

Traditional Rental Income: $2651

Airbnb ROI: 1.08%

Traditional ROI: 6.22%

5 Oak Ridge Rd

Middletown, NY

4 beds | 3 baths | 2,392 sq.ft.

$563,000

Airbnb cash on cash: 0.79%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $2881

Traditional Rental Income: $3865

Airbnb ROI: 0.79%

Traditional ROI: 3.81%

217-219 Highland Ave

Middletown, NY

3 beds | 2 baths | 2,228 sq.ft.

$479,000

Airbnb cash on cash: -0.49%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $1592

Traditional Rental Income: $3651

Airbnb ROI: -0.49%

Traditional ROI: 5.12%

568 County Route 49 #2C

Middletown, NY

3 beds | 2 baths | 1,593 sq.ft.

$399,900

Airbnb cash on cash: -1.07%

Traditional cash on cash: 4.06%

Airbnb Rental Income: $1592

Traditional Rental Income: $3061

Airbnb ROI: -1.07%

Traditional ROI: 4.06%

15 Kendal Ln

Middletown, NY

2 beds | 2 baths | 1,241 sq.ft.

$349,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $1479

Traditional Rental Income: $2540

Airbnb ROI: 0.21%

Traditional ROI: 4.78%

512 County Route 49

Middletown, NY

4 beds | 2 baths | 2,906 sq.ft.

$699,900

Airbnb cash on cash: 0.47%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $2881

Traditional Rental Income: $3963

Airbnb ROI: 0.47%