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.

Single Family Homes for Sale in Middletown, NY

Search for Single Family Residential for Sale in Middletown, New York. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 92 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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: 6.57% Traditional cash on cash: 9.12% Airbnb Rental Income: $3381 Traditional Rental Income: $3302 Airbnb ROI: 6.57% Traditional ROI: 9.12%
295 Lybolt Road Middletown, NY Spacious home with large yard on a quiet street - what more could you want? This beautiful...	3 beds \| 2 baths \| 1,222 sq.ft.	$470,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 3.44% Airbnb Rental Income: $2124 Traditional Rental Income: $2800 Airbnb ROI: 0.67% 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: 0.48% Traditional cash on cash: 5.66% Airbnb Rental Income: $2124 Traditional Rental Income: $3141 Airbnb ROI: 0.48% Traditional ROI: 5.66%
482 Scotchtown Avenue Middletown, NY Mint condition, classic, fully-restored 1863 farmhouse. This 4-bedroom, 2 1/2-bathroom hom...	4 beds \| 3 baths \| 2,828 sq.ft.	$829,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.5% Airbnb Rental Income: $2984 Traditional Rental Income: $3892 Airbnb ROI: 0.43% Traditional ROI: 2.5%
12 Briarwood Drive Middletown, NY This well-maintained home is located in a peaceful neighborhood with a pleasant environmen...	3 beds \| 3 baths \| 2,184 sq.ft.	$450,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 5.13% Airbnb Rental Income: $2124 Traditional Rental Income: $3520 Airbnb ROI: 0.52% Traditional ROI: 5.13%
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: 1.54% Traditional cash on cash: 3.85% Airbnb Rental Income: $2124 Traditional Rental Income: $2437 Airbnb ROI: 1.54% 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.	$418,999	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.93% Airbnb Rental Income: $2124 Traditional Rental Income: $2783 Airbnb ROI: 0.87% Traditional ROI: 3.93%
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: 3.2% Traditional cash on cash: 7.62% Airbnb Rental Income: $2984 Traditional Rental Income: $4018 Airbnb ROI: 3.2% Traditional ROI: 7.62%
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: -0.4% Traditional cash on cash: 0.74% Airbnb Rental Income: $2984 Traditional Rental Income: $3993 Airbnb ROI: -0.4% 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: 0.73% Traditional cash on cash: 4.49% Airbnb Rental Income: $2124 Traditional Rental Income: $3160 Airbnb ROI: 0.73% 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.	$375,000	Airbnb cash on cash: 3.47% Traditional cash on cash: 6.56% Airbnb Rental Income: $2984 Traditional Rental Income: $3385 Airbnb ROI: 3.47% Traditional ROI: 6.56%
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: 1.1% Traditional cash on cash: 6.26% Airbnb Rental Income: $2124 Traditional Rental Income: $3660 Airbnb ROI: 1.1% Traditional ROI: 6.26%
184 Highland Avenue Middletown, NY Here you have a beautiful Victorian style home, centrally located in Middletown NY. This h...	4 beds \| 2 baths \| 1,486 sq.ft.	$355,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 6.88% Airbnb Rental Income: $2984 Traditional Rental Income: $3381 Airbnb ROI: 3.63% Traditional ROI: 6.88%
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: 2.78% Traditional cash on cash: 6.88% Airbnb Rental Income: $2124 Traditional Rental Income: $2722 Airbnb ROI: 2.78% Traditional ROI: 6.88%
15 Rowan Street #13 Middletown, NY Discover the perfect blend of comfort and charm in this beautifully updated home, nestled ...	5 beds \| 2 baths \| 1,920 sq.ft.	$415,789	Airbnb cash on cash: 3.84% Traditional cash on cash: 5.92% Airbnb Rental Income: $3381 Traditional Rental Income: $3441 Airbnb ROI: 3.84% Traditional ROI: 5.92%
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: 2.33% Traditional cash on cash: 4.65% Airbnb Rental Income: $2124 Traditional Rental Income: $2289 Airbnb ROI: 2.33% 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: 0.04% Traditional cash on cash: 3.41% Airbnb Rental Income: $2124 Traditional Rental Income: $3404 Airbnb ROI: 0.04% Traditional ROI: 3.41%
14 Laddie Road Middletown, NY Charming Renovated Split-Level Home in Pine Bush School District! Welcome to your dre...	3 beds \| 2 baths \| 1,702 sq.ft.	$439,900	Airbnb cash on cash: 1.15% Traditional cash on cash: 4.79% Airbnb Rental Income: $2124 Traditional Rental Income: $3079 Airbnb ROI: 1.15% Traditional ROI: 4.79%
200 Mt Orange Road Middletown, NY Welcome to this most charming 1870's farmhouse situated on idyllic 6.4 level pastoral acr...	4 beds \| 4 baths \| 3,432 sq.ft.	$699,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 3.18% Airbnb Rental Income: $2984 Traditional Rental Income: $4051 Airbnb ROI: 0.49% Traditional ROI: 3.18%
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: 3.95% Traditional cash on cash: 5.99% Airbnb Rental Income: $2984 Traditional Rental Income: $3063 Airbnb ROI: 3.95% Traditional ROI: 5.99%
40 Camp Orange Road Middletown, NY This versatile and lucrative investment or user property sits on one of the largest open l...	5 beds \| 2 baths \| 2,092 sq.ft.	$2,995,000	Airbnb cash on cash: -1.36% Traditional cash on cash: -1.08% Airbnb Rental Income: $3381 Traditional Rental Income: $3405 Airbnb ROI: -1.36% Traditional ROI: -1.08%
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.	$825,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 2.32% Airbnb Rental Income: $3381 Traditional Rental Income: $4169 Airbnb ROI: 0.31% Traditional ROI: 2.32%
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.	$405,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 3.44% Airbnb Rental Income: $2124 Traditional Rental Income: $2489 Airbnb ROI: 1.05% Traditional ROI: 3.44%
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: 0.32% Traditional cash on cash: 2.22% Airbnb Rental Income: $2984 Traditional Rental Income: $3676 Airbnb ROI: 0.32% 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.	$499,999	Airbnb cash on cash: 0.1% Traditional cash on cash: 3.83% Airbnb Rental Income: $2124 Traditional Rental Income: $3329 Airbnb ROI: 0.1% Traditional ROI: 3.83%
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.	$389,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 3.58% Airbnb Rental Income: $2124 Traditional Rental Income: $2260 Airbnb ROI: 1.72% Traditional ROI: 3.58%
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: 5.28% Traditional cash on cash: 6.86% Airbnb Rental Income: $3381 Traditional Rental Income: $3149 Airbnb ROI: 5.28% Traditional ROI: 6.86%
214 Phillips Street Middletown, NY Welcome to this beautiful newly built 4-bedroom, 3.5-bath home featuring a spacious 2,760 ...	4 beds \| 4 baths \| 2,760 sq.ft.	$625,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.43% Airbnb Rental Income: $2984 Traditional Rental Income: $3784 Airbnb ROI: 0.89% Traditional ROI: 3.43%
149 Brown Road Middletown, NY Looking for house to make your own, look no further! This adorable 2 bed 2 bath home situa...	2 beds \| 2 baths \| 1,631 sq.ft.	$399,900	Airbnb cash on cash: 0.52% Traditional cash on cash: 4.07% Airbnb Rental Income: $1558 Traditional Rental Income: $2438 Airbnb ROI: 0.52% Traditional ROI: 4.07%
9 Fairview Avenue Middletown, NY A must see home! This beautiful colonial home will have everything brand new - from the e...	3 beds \| 2 baths \| 1,056 sq.ft.	$329,900	Airbnb cash on cash: 2.1% Traditional cash on cash: 5.38% Airbnb Rental Income: $2124 Traditional Rental Income: $2598 Airbnb ROI: 2.1% Traditional ROI: 5.38%
255 Howells Road Middletown, NY Enter the gates of this grand estate, where you'll find a stunning 5-bedroom, 5-bathroom h...	5 beds \| 5 baths \| 4,200 sq.ft.	$999,900	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.98% Airbnb Rental Income: $3381 Traditional Rental Income: $5869 Airbnb ROI: 0.5% Traditional ROI: 3.98%
36 Karen Drive Middletown, NY This cozy 3-bedroom, 1-bathroom home is packed with features and surrounded by natural bea...	3 beds \| 1 baths \| 1,436 sq.ft.	$379,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 4.06% Airbnb Rental Income: $2124 Traditional Rental Income: $2489 Airbnb ROI: 1.51% Traditional ROI: 4.06%
4 Langton Mews Middletown, NY Welcome to 4 Langton Mews!This contemporary home offers an open-concept layout with a brig...	3 beds \| 2 baths \| 1,604 sq.ft.	$318,250	Airbnb cash on cash: 1.41% Traditional cash on cash: 6% Airbnb Rental Income: $2124 Traditional Rental Income: $2955 Airbnb ROI: 1.41% Traditional ROI: 6%
54 Brewster Drive Middletown, NY Welcome to this charming 3 bedroom, 1 and 1/2 bath raised ranch in the heart of Middletown...	3 beds \| 2 baths \| 1,914 sq.ft.	$409,900	Airbnb cash on cash: 0.38% Traditional cash on cash: 4.1% Airbnb Rental Income: $2124 Traditional Rental Income: $3011 Airbnb ROI: 0.38% Traditional ROI: 4.1%
120 Prospect Avenue Middletown, NY Back on market! Buyer lost financing!! What a complete honor to represent this home, the...	3 beds \| 2 baths \| 1,382 sq.ft.	$389,000	Airbnb cash on cash: 1.62% Traditional cash on cash: 5.22% Airbnb Rental Income: $2124 Traditional Rental Income: $2895 Airbnb ROI: 1.62% Traditional ROI: 5.22%
13 Smith Street Middletown, NY Looking to add a rental property to your porfolio? This 3 bedroom, 1 bathroom home might b...	3 beds \| 1 baths \| 1,120 sq.ft.	$250,000	Airbnb cash on cash: 3.62% Traditional cash on cash: 6.41% Airbnb Rental Income: $2124 Traditional Rental Income: $2241 Airbnb ROI: 3.62% Traditional ROI: 6.41%
727 Route 17M Middletown, NY Single Family home and mix-use property in prime location. Live on the property and have ...	1 beds \| 1 baths \| 1,088 sq.ft.	$535,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 1.96% Airbnb Rental Income: $1320 Traditional Rental Income: $2012 Airbnb ROI: -0.25% Traditional ROI: 1.96%
94 Fair Oaks Road Middletown, NY AVAILABLE NEW CONSTRUCTION BILONIAL BEAUTY ON 10+ ACRES! Welcome to your dream home â...	4 beds \| 3 baths \| 2,434 sq.ft.	$599,900	Airbnb cash on cash: 1.12% Traditional cash on cash: 4.04% Airbnb Rental Income: $2984 Traditional Rental Income: $3938 Airbnb ROI: 1.12% Traditional ROI: 4.04%
10 Willow Place Middletown, NY Move right into this charming 3 bedroom 2 bath split level home. The property offers bonus...	3 beds \| 2 baths \| 1,430 sq.ft.	$410,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 5.71% Airbnb Rental Income: $2124 Traditional Rental Income: $3339 Airbnb ROI: 1.13% Traditional ROI: 5.71%
129 Foster Road Middletown, NY Tucked away in the woods, this cozy 1-bedroom cottage offers the perfect escape into natur...	1 beds \| 1 baths \| 512 sq.ft.	$199,999	Airbnb cash on cash: 2.1% Traditional cash on cash: 6.73% Airbnb Rental Income: $1320 Traditional Rental Income: $1790 Airbnb ROI: 2.1% Traditional ROI: 6.73%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middletown, NY

30 East Avenue

Middletown, NY

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

$280,000

Airbnb cash on cash: 6.57%

Traditional cash on cash: 9.12%

Airbnb Rental Income: $3381

Traditional Rental Income: $3302

Airbnb ROI: 6.57%

Traditional ROI: 9.12%

295 Lybolt Road

Middletown, NY

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

$470,000

Airbnb cash on cash: 0.67%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $2124

Traditional Rental Income: $2800

Airbnb ROI: 0.67%

Traditional ROI: 3.44%

115 Vincent Drive

Middletown, NY

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

$320,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 5.66%

Airbnb Rental Income: $2124

Traditional Rental Income: $3141

Airbnb ROI: 0.48%

Traditional ROI: 5.66%

482 Scotchtown Avenue

Middletown, NY

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

$829,000

Airbnb cash on cash: 0.43%

Traditional cash on cash: 2.5%

Airbnb Rental Income: $2984

Traditional Rental Income: $3892

Airbnb ROI: 0.43%

Traditional ROI: 2.5%

12 Briarwood Drive

Middletown, NY

3 beds | 3 baths | 2,184 sq.ft.

$450,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $2124

Traditional Rental Income: $3520

Airbnb ROI: 0.52%

Traditional ROI: 5.13%

5 Peace Drive

Middletown, NY

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

$395,000

Airbnb cash on cash: 1.54%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $2124

Traditional Rental Income: $2437

Airbnb ROI: 1.54%

Traditional ROI: 3.85%

77 Prince Street

Middletown, NY

3 beds | 3 baths | 1,245 sq.ft.

$418,999

Airbnb cash on cash: 0.87%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $2124

Traditional Rental Income: $2783

Airbnb ROI: 0.87%

Traditional ROI: 3.93%

167 Rockwell Avenue

Middletown, NY

4 beds | 3 baths | 2,040 sq.ft.

$415,000

Airbnb cash on cash: 3.2%

Traditional cash on cash: 7.62%

Airbnb Rental Income: $2984

Traditional Rental Income: $4018

Airbnb ROI: 3.2%