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
30 East Avenue Middletown, NY CALLING ALL INVESTORS! Turn of the century charmer located right in the heart of Middletow...	5 beds \| 2 baths \| 1,941 sq.ft.	$280,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.12% Airbnb Rental Income: $null Traditional Rental Income: $3302 Airbnb ROI: N/A Traditional ROI: 9.12%
38 Woodside Knolls Drive Middletown, NY Welcome to Woodside Knolls! Discover this stunning tri-level townhouse located in one of t...	3 beds \| 4 baths \| 1,899 sq.ft.	$479,000	Airbnb cash on cash: -1.56% Traditional cash on cash: 5.09% Airbnb Rental Income: $1260 Traditional Rental Income: $3844 Airbnb ROI: -1.56% Traditional ROI: 5.09%
295 Lybolt Road Middletown, NY A/O 9.1.25 ... Spacious home with large yard on a quiet street - what more could you want?...	3 beds \| 2 baths \| 1,222 sq.ft.	$470,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 3.44% Airbnb Rental Income: $1260 Traditional Rental Income: $2800 Airbnb ROI: -0.97% Traditional ROI: 3.44%
115 Vincent Drive Middletown, NY Check out 115 Vincent Drive, a unique split ranch in Middletown, NY. Itâs close to every...	3 beds \| 2 baths \| 1,964 sq.ft.	$320,000	Airbnb cash on cash: -1.92% Traditional cash on cash: 5.66% Airbnb Rental Income: $1260 Traditional Rental Income: $3141 Airbnb ROI: -1.92% Traditional ROI: 5.66%
482 Scotchtown Avenue Middletown, NY Classic 1863 Farmhouse in Mint Condition â Riverfront Property in Goshen School District...	5 beds \| 3 baths \| 2,828 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.62% Airbnb Rental Income: $null Traditional Rental Income: $3892 Airbnb ROI: N/A Traditional ROI: 2.62%
24 Kent Court Middletown, NY Elegant 2-Bedroom, 3-Bath End Unit in Sought-After Waters Edge Community Welcome to this ...	2 beds \| 3 baths \| 1,241 sq.ft.	$349,900	Airbnb cash on cash: 0.44% Traditional cash on cash: 5.86% Airbnb Rental Income: $1606 Traditional Rental Income: $2931 Airbnb ROI: 0.44% Traditional ROI: 5.86%
5 Raleigh Close Middletown, NY CANTERBURY KNOLLS of Wallkill now offers this GORGEOUS TURN-KEY Contemporary style home ju...	3 beds \| 2 baths \| 1,608 sq.ft.	$375,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 5.09% Airbnb Rental Income: $1260 Traditional Rental Income: $2999 Airbnb ROI: -0.99% Traditional ROI: 5.09%
5 Peace Drive Middletown, NY Commuter's Dream in the Town Of Wallkill ! This 3 Bedroom Raised Ranch offers hardwood flo...	3 beds \| 1 baths \| 1,144 sq.ft.	$395,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 3.85% Airbnb Rental Income: $1260 Traditional Rental Income: $2437 Airbnb ROI: -0.4% Traditional ROI: 3.85%
77 Prince Street Middletown, NY Welcome to this beautiful well maintained contemporary two story home nestled in the heart...	3 beds \| 3 baths \| 1,245 sq.ft.	$409,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 4.05% Airbnb Rental Income: $1260 Traditional Rental Income: $2783 Airbnb ROI: -0.96% Traditional ROI: 4.05%
167 Rockwell Avenue Middletown, NY Charming Single-Family Home for Sale Welcome to this beautifully designed, spacious single...	4 beds \| 3 baths \| 2,040 sq.ft.	$415,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 7.62% Airbnb Rental Income: $2396 Traditional Rental Income: $4018 Airbnb ROI: 1.94% Traditional ROI: 7.62%
44 Houston Avenue Middletown, NY Excellent opportunity to own a 2 family house whether you are an investor or want to live ...	5 beds \| 2 baths \| 2,440 sq.ft.	$369,900	Airbnb cash on cash: 2.14% Traditional cash on cash: 6.72% Airbnb Rental Income: $2396 Traditional Rental Income: $3397 Airbnb ROI: 2.14% Traditional ROI: 6.72%
350 Concord Lane Middletown, NY Welcome to this beautiful 2-bedroom, 2-bathroom condo located in the heart of Middletown, ...	2 beds \| 2 baths \| 955 sq.ft.	$213,999	Airbnb cash on cash: -0.23% Traditional cash on cash: 4.94% Airbnb Rental Income: $1606 Traditional Rental Income: $2198 Airbnb ROI: -0.23% Traditional ROI: 4.94%
565 Prosperous Valley Road Middletown, NY Your dream countryside retreat located in Orange County NY. This custom-built 4,000 sq. ft...	4 beds \| 3 baths \| 4,000 sq.ft.	$1,600,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.74% Airbnb Rental Income: $2396 Traditional Rental Income: $3993 Airbnb ROI: -0.73% Traditional ROI: 0.74%
6 Tice Lane Middletown, NY Set on 3 peaceful acres in a private country setting, this well-maintained raised ranch of...	3 beds \| 2 baths \| 2,070 sq.ft.	$449,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 4.49% Airbnb Rental Income: $1260 Traditional Rental Income: $3160 Airbnb ROI: -0.98% Traditional ROI: 4.49%
24 Edinburgh Road Middletown, NY Looking for something different? This spacious 4 bedroom 2 full bath contemporary raised r...	4 beds \| 2 baths \| 1,796 sq.ft.	$360,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 6.87% Airbnb Rental Income: $2396 Traditional Rental Income: $3385 Airbnb ROI: 2.21% Traditional ROI: 6.87%
411 Fair Oaks Road Middletown, NY Welcome Home! Solid Raised Ranch located in the Town of Wallkill/Pine Bush School District...	3 beds \| 3 baths \| 2,496 sq.ft.	$429,900	Airbnb cash on cash: -0.69% Traditional cash on cash: 6.26% Airbnb Rental Income: $1260 Traditional Rental Income: $3660 Airbnb ROI: -0.69% Traditional ROI: 6.26%
8 Ebury Middletown, NY Spacious 4-Bedroom Retreat in Canterbury Knolls â Town of Wallkill Experience the perfe...	4 beds \| 3 baths \| 1,505 sq.ft.	$378,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 5.53% Airbnb Rental Income: $2396 Traditional Rental Income: $3080 Airbnb ROI: 1.94% Traditional ROI: 5.53%
2 Rivervale Road Middletown, NY Charming Corner Townhouse in Middletown â No HOA Fees! Welcome to 2 Riverdale Road, a de...	3 beds \| 2 baths \| 1,484 sq.ft.	$350,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 5.51% Airbnb Rental Income: $1260 Traditional Rental Income: $2763 Airbnb ROI: -0.27% Traditional ROI: 5.51%
17 N Aspen Road Middletown, NY This renovated 2-bedroom, 1.5-bath townhouse in Middletown offers a perfect blend of comfo...	2 beds \| 2 baths \| 1,144 sq.ft.	$269,900	Airbnb cash on cash: 1.4% Traditional cash on cash: 6.11% Airbnb Rental Income: $1606 Traditional Rental Income: $2348 Airbnb ROI: 1.4% Traditional ROI: 6.11%
105 Sheffield Drive Middletown, NY Town of Wallkill Townhouse - Low Taxes - Great Investment This charming 3-bedroom, 1.5-ba...	3 beds \| 2 baths \| 1,400 sq.ft.	$295,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 6.88% Airbnb Rental Income: $1260 Traditional Rental Income: $2722 Airbnb ROI: 0.19% Traditional ROI: 6.88%
841 Howells Turnpike Middletown, NY Welcome to 841 Howells Turnpike â Your Private Retreat in the Pine Bush School District ...	3 beds \| 3 baths \| 2,200 sq.ft.	$549,900	Airbnb cash on cash: -1.52% Traditional cash on cash: 3.66% Airbnb Rental Income: $1260 Traditional Rental Income: $3525 Airbnb ROI: -1.52% Traditional ROI: 3.66%
24 Crescent Place Middletown, NY Attention all investors and home buyers! Look no further, This amazing colonial is in grea...	3 beds \| 1 baths \| 1,196 sq.ft.	$325,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 4.65% Airbnb Rental Income: $1260 Traditional Rental Income: $2289 Airbnb ROI: -0.02% Traditional ROI: 4.65%
30 Daly Road Middletown, NY New Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partiall...	3 beds \| 3 baths \| 2,205 sq.ft.	$579,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 3.38% Airbnb Rental Income: $1260 Traditional Rental Income: $3404 Airbnb ROI: -1.32% Traditional ROI: 3.38%
324 Concord Lane Middletown, NY Welcome to this beautiful condo in the Buttonwood Hills complex! This bright and spacious ...	1 beds \| 1 baths \| 735 sq.ft.	$168,500	Airbnb cash on cash: -2.29% Traditional cash on cash: 1.85% Airbnb Rental Income: $1133 Traditional Rental Income: $1420 Airbnb ROI: -2.29% Traditional ROI: 1.85%
17 Sterling Street Middletown, NY Turnkey Two-Family Investment Opportunity. Fully renovated from the studs up just two year...	6 beds \| 2 baths \| 1,400 sq.ft.	$459,999	Airbnb cash on cash: -0.84% Traditional cash on cash: 5.99% Airbnb Rental Income: $1133 Traditional Rental Income: $3694 Airbnb ROI: -0.84% Traditional ROI: 5.99%
147 Ruth Court Middletown, NY Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in Middletown! Featurin...	2 beds \| 3 baths \| 880 sq.ft.	$269,900	Airbnb cash on cash: 1.12% Traditional cash on cash: 4.08% Airbnb Rental Income: $1606 Traditional Rental Income: $1905 Airbnb ROI: 1.12% Traditional ROI: 4.08%
242 Derby Road Middletown, NY Some homes simply check the boxes. Others feel like they were built with care from the gro...	3 beds \| 3 baths \| 2,214 sq.ft.	$419,900	Airbnb cash on cash: 0.18% Traditional cash on cash: 2.85% Airbnb Rental Income: $1260 Traditional Rental Income: $1912 Airbnb ROI: 0.18% Traditional ROI: 2.85%
168 S Centerville Road Middletown, NY This is one of the Kind property in the Minisink School District . This Beautiful Colonial...	4 beds \| 3 baths \| 3,088 sq.ft.	$668,900	Airbnb cash on cash: 0.11% Traditional cash on cash: 3.6% Airbnb Rental Income: $2396 Traditional Rental Income: $3991 Airbnb ROI: 0.11% Traditional ROI: 3.6%
47 Prince Street Middletown, NY Welcome to this lovely, renovated. Formerly a 3 bedroom/2-bathroom house, this home has be...	4 beds \| 3 baths \| 1,620 sq.ft.	$399,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 5.99% Airbnb Rental Income: $2396 Traditional Rental Income: $3063 Airbnb ROI: 2.64% Traditional ROI: 5.99%
49 Ruth Court Middletown, NY Smart Buy â Ideal for Investors or Future Homeowners! This well-maintained 2-bedroom, 1-...	2 beds \| 1 baths \| 1,006 sq.ft.	$207,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 5.11% Airbnb Rental Income: $1606 Traditional Rental Income: $1772 Airbnb ROI: 1.94% Traditional ROI: 5.11%
104 Elise Drive Middletown, NY LAST HOME AVAILABLE! Welcome to The Woodlands at Scotchtown Estates! This exquisite pictur...	5 beds \| 4 baths \| 3,700 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.49% Airbnb Rental Income: $null Traditional Rental Income: $4169 Airbnb ROI: N/A Traditional ROI: 2.49%
71 Commonwealth Avenue Middletown, NY Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant h...	3 beds \| 1 baths \| 1,344 sq.ft.	$375,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 3.79% Airbnb Rental Income: $1260 Traditional Rental Income: $2489 Airbnb ROI: -0.84% Traditional ROI: 3.79%
225 Van Duzer Road Middletown, NY Welcome to a stunning brand new Colonial Home nestled in the heart of the town of Wallkill...	4 beds \| 3 baths \| 3,900 sq.ft.	$779,900	Airbnb cash on cash: -0.35% Traditional cash on cash: 2.22% Airbnb Rental Income: $2396 Traditional Rental Income: $3676 Airbnb ROI: -0.35% Traditional ROI: 2.22%
7 Avoncroft Lane Middletown, NY Discover the perfect balance of modern design and everyday comfort in this beautifully upd...	3 beds \| 3 baths \| 2,567 sq.ft.	$489,999	Airbnb cash on cash: -1.45% Traditional cash on cash: 3.93% Airbnb Rental Income: $1260 Traditional Rental Income: $3329 Airbnb ROI: -1.45% Traditional ROI: 3.93%
19 - 20 Lake Claire Drive Middletown, NY TWO FOR THE PRICE OF ONE! Escape the hustle and bustle of city life to enjoy nature at its...	2 beds \| 2 baths \| 1,308 sq.ft.	$229,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 6.21% Airbnb Rental Income: $1260 Traditional Rental Income: $1900 Airbnb ROI: 1.44% Traditional ROI: 6.21%
42 Genung Street Middletown, NY BEAUTIFUL turn-key home located in MIDDLETOWN! Do NOT let the ouside fool you as this home...	4 beds \| 3 baths \| 1,728 sq.ft.	$425,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 2.87% Airbnb Rental Income: $2396 Traditional Rental Income: $2179 Airbnb ROI: 1.94% Traditional ROI: 2.87%
1 Chestnut Street Middletown, NY A must see home! This beautiful corner lot home has everything brand new inside - from the...	3 beds \| 1 baths \| 1,100 sq.ft.	$379,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.7% Airbnb Rental Income: $1260 Traditional Rental Income: $2260 Airbnb ROI: -0.24% Traditional ROI: 3.7%
53 Richmond Place Middletown, NY Beautifully renovated two-story home in Orange County! Featuring a brand-new kitchen with ...	3 beds \| 1 baths \| 1,144 sq.ft.	$349,999	Airbnb cash on cash: -0.19% Traditional cash on cash: 4.26% Airbnb Rental Income: $1260 Traditional Rental Income: $2324 Airbnb ROI: -0.19% Traditional ROI: 4.26%
17 Little Avenue Middletown, NY Fully Available...Opportunity Knocks to acquire this fully detached One family home in the...	5 beds \| 2 baths \| 1,670 sq.ft.	$349,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $3149 Airbnb ROI: N/A Traditional ROI: 6.86%
9 Genung Street Middletown, NY Charming two-story home in the heart of Middletown! This spacious residence offers a welco...	3 beds \| 2 baths \| 1,240 sq.ft.	$349,990	Airbnb cash on cash: -0.1% Traditional cash on cash: 5% Airbnb Rental Income: $1260 Traditional Rental Income: $2538 Airbnb ROI: -0.1% Traditional ROI: 5%

Real Estate investment in Middletown, NY

There are 135 properties for sale in the city of Middletown . The median list price in Middletown is $399,450 and the average price per square foot is $212. In October 2025, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $3,113.

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

There are 135 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 $1,260.

Your search for investment property begins and ends here

Investment Property for Sale in Middletown, NY

30 East Avenue

Middletown, NY

5 beds | 2 baths | 1,941 sq.ft.

$280,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.12%

Airbnb Rental Income: $null

Traditional Rental Income: $3302

Airbnb ROI: N/A

Traditional ROI: 9.12%

38 Woodside Knolls Drive

Middletown, NY

3 beds | 4 baths | 1,899 sq.ft.

$479,000

Airbnb cash on cash: -1.56%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $1260

Traditional Rental Income: $3844

Airbnb ROI: -1.56%

Traditional ROI: 5.09%

295 Lybolt Road

Middletown, NY

3 beds | 2 baths | 1,222 sq.ft.

$470,000

Airbnb cash on cash: -0.97%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $1260

Traditional Rental Income: $2800

Airbnb ROI: -0.97%

Traditional ROI: 3.44%

115 Vincent Drive

Middletown, NY

3 beds | 2 baths | 1,964 sq.ft.

$320,000

Airbnb cash on cash: -1.92%

Traditional cash on cash: 5.66%

Airbnb Rental Income: $1260

Traditional Rental Income: $3141

Airbnb ROI: -1.92%

Traditional ROI: 5.66%

482 Scotchtown Avenue

Middletown, NY

5 beds | 3 baths | 2,828 sq.ft.

$799,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.62%

Airbnb Rental Income: $null

Traditional Rental Income: $3892

Airbnb ROI: N/A

Traditional ROI: 2.62%

24 Kent Court

Middletown, NY

2 beds | 3 baths | 1,241 sq.ft.

$349,900

Airbnb cash on cash: 0.44%

Traditional cash on cash: 5.86%

Airbnb Rental Income: $1606

Traditional Rental Income: $2931

Airbnb ROI: 0.44%

Traditional ROI: 5.86%

5 Raleigh Close

Middletown, NY

3 beds | 2 baths | 1,608 sq.ft.

$375,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $1260

Traditional Rental Income: $2999

Airbnb ROI: -0.99%

Traditional ROI: 5.09%

5 Peace Drive

Middletown, NY

3 beds | 1 baths | 1,144 sq.ft.

$395,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $1260

Traditional Rental Income: $2437

Airbnb ROI: -0.4%