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 82 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
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%
214 Brown Road Middletown, NY Sitting perfectly on 5.3 acres with a 2+ acre spring-fed, fully aerated pond, "Fair Oaks R...	3 beds \| 4 baths \| 2,240 sq.ft.	$695,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 3.23% Airbnb Rental Income: $4661 Traditional Rental Income: $3765 Airbnb ROI: 3.12% Traditional ROI: 3.23%
600 Goshen Turnpike Middletown, NY Goshen turpike now offers you this turnkey 3 bedrrom/2.5 bath home that sits on 4 acres of...	3 beds \| 3 baths \| 2,000 sq.ft.	$490,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 4.1% Airbnb Rental Income: $4661 Traditional Rental Income: $3278 Airbnb ROI: 5.01% Traditional ROI: 4.1%
19 W Conkling Avenue Middletown, NY BEAUTIFUL home located in a quiet neighborhood of Middletown! Enter into an inclosed deck...	2 beds \| 1 baths \| 840 sq.ft.	$299,900	Airbnb cash on cash: 5.39% Traditional cash on cash: 4.66% Airbnb Rental Income: $3101 Traditional Rental Income: $2190 Airbnb ROI: 5.39% Traditional ROI: 4.66%
24 Rhode Island Avenue Middletown, NY Major renovation project in the works. House being sold As Is, Where Is. Bare studs insi...	2 beds \| 2 baths \| 1,248 sq.ft.	$249,900	Airbnb cash on cash: 7.01% Traditional cash on cash: 6% Airbnb Rental Income: $3101 Traditional Rental Income: $2157 Airbnb ROI: 7.01% Traditional ROI: 6%
18 Pennsylvania Avenue Middletown, NY Nestled at the end of a serene cul-de-sac, this charming 3-bedroom, 2-bath ranch offers 1,...	3 beds \| 2 baths \| 1,008 sq.ft.	$350,000	Airbnb cash on cash: 7.84% Traditional cash on cash: 5.02% Airbnb Rental Income: $4464 Traditional Rental Income: $2601 Airbnb ROI: 7.84% Traditional ROI: 5.02%
25 Meyer Road Middletown, NY A-Frame home in the town of Wallkill within the Minisink School District. The home is nest...	3 beds \| 2 baths \| 1,335 sq.ft.	$390,000	Airbnb cash on cash: 6.84% Traditional cash on cash: 5.54% Airbnb Rental Income: $4464 Traditional Rental Income: $3056 Airbnb ROI: 6.84% Traditional ROI: 5.54%
26 Mills Avenue Middletown, NY Looking for a Large home for the extended family or Inlaw-suite/Mother Daughter setup? Loo...	5 beds \| 3 baths \| 2,200 sq.ft.	$319,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.9% Airbnb Rental Income: $null Traditional Rental Income: $3675 Airbnb ROI: N/A Traditional ROI: 8.9%
121 Rockwell Avenue Middletown, NY Well maintained and updated home located in the heart of Middletown. This home offers 3 be...	3 beds \| 1 baths \| 1,019 sq.ft.	$345,000	Airbnb cash on cash: 8.62% Traditional cash on cash: 4.78% Airbnb Rental Income: $4464 Traditional Rental Income: $2288 Airbnb ROI: 8.62% Traditional ROI: 4.78%
27 Restorative Lane Middletown, NY As you approach the property down a long, well-maintained driveway, youâre guided throug...	4 beds \| 4 baths \| 2,189 sq.ft.	$650,000	Airbnb cash on cash: 4.64% Traditional cash on cash: 3.87% Airbnb Rental Income: $5817 Traditional Rental Income: $4189 Airbnb ROI: 4.64% Traditional ROI: 3.87%
16 Beth Place Middletown, NY Welcome to Beth Place. This charming, fully detached, raised ranch is near everything that...	3 beds \| 3 baths \| 1,814 sq.ft.	$429,000	Airbnb cash on cash: 5.49% Traditional cash on cash: 4.98% Airbnb Rental Income: $4464 Traditional Rental Income: $3328 Airbnb ROI: 5.49% Traditional ROI: 4.98%
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.	$550,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 3.64% Airbnb Rental Income: $4464 Traditional Rental Income: $3404 Airbnb ROI: 3.89% Traditional ROI: 3.64%
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.	$699,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 3.41% Airbnb Rental Income: $5817 Traditional Rental Income: $3991 Airbnb ROI: 4.43% Traditional ROI: 3.41%
14 Sunrise Drive Middletown, NY NEW CONSTRUCTION RANCH ON A LOVELY DEAD END STREET! ONE LEVEL LIVING, WITH 3 BEDROOMS, PRI...	3 beds \| 2 baths \| 1,536 sq.ft.	$445,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 3.72% Airbnb Rental Income: $4464 Traditional Rental Income: $2987 Airbnb ROI: 5.03% Traditional ROI: 3.72%
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.	$675,000	Airbnb cash on cash: 4.29% Traditional cash on cash: 3.32% Airbnb Rental Income: $5817 Traditional Rental Income: $4051 Airbnb ROI: 4.29% Traditional ROI: 3.32%
62 New York Avenue Middletown, NY STUNNING home located in a quiet neighborhood of the Town of Wallkill! This home is in min...	5 beds \| 3 baths \| 2,200 sq.ft.	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.12% Airbnb Rental Income: $null Traditional Rental Income: $3609 Airbnb ROI: N/A Traditional ROI: 6.12%
116 Wawayanda Avenue Middletown, NY A perfect colonial home with a Mother - Daughter set up is now under construction in the c...	5 beds \| 4 baths \| 2,850 sq.ft.	$569,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.65% Airbnb Rental Income: $null Traditional Rental Income: $4009 Airbnb ROI: N/A Traditional ROI: 4.65%
29 Oliver Avenue Middletown, NY Completely renovated in 2023, this move-in ready house boasts a prime location across from...	3 beds \| 2 baths \| 2,013 sq.ft.	$379,000	Airbnb cash on cash: 6.91% Traditional cash on cash: 6.07% Airbnb Rental Income: $4464 Traditional Rental Income: $3232 Airbnb ROI: 6.91% Traditional ROI: 6.07%
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.	$410,000	Airbnb cash on cash: 9.96% Traditional cash on cash: 5.81% Airbnb Rental Income: $5817 Traditional Rental Income: $3063 Airbnb ROI: 9.96% Traditional ROI: 5.81%
39 Hanford Street Middletown, NY Newly renovated 1 Family Home with 5 Bedrooms, and 2,634 SQ.FT, on a quiet and peaceful st...	5 beds \| 2 baths \| 2,634 sq.ft.	$399,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.93% Airbnb Rental Income: $null Traditional Rental Income: $3493 Airbnb ROI: N/A Traditional ROI: 6.93%
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: N/A Traditional cash on cash: -1.08% Airbnb Rental Income: $null Traditional Rental Income: $3405 Airbnb ROI: N/A Traditional ROI: -1.08%
104 Elise Drive Middletown, NY Welcome to The Woodlands at Scotchtown Estates! This exquisite picturesque community sits ...	5 beds \| 4 baths \| 3,700 sq.ft.	$869,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $4169 Airbnb ROI: N/A Traditional ROI: 2.15%
102 Elise Drive Middletown, NY Welcome to The Woodlands at Scotchtown Estates! This exquisite picturesque community sits ...	5 beds \| 4 baths \| 3,700 sq.ft.	$869,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $4169 Airbnb ROI: N/A Traditional ROI: 2.15%
197 Elise Drive Middletown, NY Welcome to Scotchtown Estates! This exquisite picturesque community sits in the highly sou...	4 beds \| 3 baths \| 3,217 sq.ft.	$779,900	Airbnb cash on cash: 3.6% Traditional cash on cash: 2.03% Airbnb Rental Income: $6131 Traditional Rental Income: $3776 Airbnb ROI: 3.6% Traditional ROI: 2.03%
258 Phillipsburg Road Middletown, NY Attention all investors! Donât miss this incredible opportunity to own a sprawling acrea...	2 beds \| 2 baths \| 1,092 sq.ft.	$345,000	Airbnb cash on cash: 4.39% Traditional cash on cash: 4.39% Airbnb Rental Income: $3101 Traditional Rental Income: $2395 Airbnb ROI: 4.39% Traditional ROI: 4.39%
4 Cherry Street Middletown, NY Classic Large Brick Cape Cod-Style Home for Sale This mother-daughter home sits on a 100 ...	5 beds \| 3 baths \| 2,445 sq.ft.	$390,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.52% Airbnb Rental Income: $null Traditional Rental Income: $3162 Airbnb ROI: N/A Traditional ROI: 5.52%
225 Van Duzer Road Middletown, NY Brand-new construction that blends modern design w functionality. The picturesque porch, i...	4 beds \| 3 baths \| 2,900 sq.ft.	$709,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 2.71% Airbnb Rental Income: $5817 Traditional Rental Income: $3676 Airbnb ROI: 4.2% Traditional ROI: 2.71%
22 1/2 Royce Avenue Middletown, NY GORGEOUS Turn-key Middletown home minutes from Presidential schools and YMCA. Front deck w...	3 beds \| 2 baths \| 1,648 sq.ft.	$415,000	Airbnb cash on cash: 6.68% Traditional cash on cash: 3.97% Airbnb Rental Income: $4464 Traditional Rental Income: $2480 Airbnb ROI: 6.68% Traditional ROI: 3.97%
141 Elise Drive Middletown, NY Welcome to Scotchtown Estates! This exquisite picturesque community sits in the highly sou...	4 beds \| 3 baths \| 2,641 sq.ft.	$799,900	Airbnb cash on cash: 3.36% Traditional cash on cash: 1.67% Airbnb Rental Income: $6131 Traditional Rental Income: $3659 Airbnb ROI: 3.36% Traditional ROI: 1.67%
123 Elise Drive Middletown, NY Welcome to The Woodlands at Scotchtown Estates! This exquisite picturesque community sits ...	5 beds \| 5 baths \| 3,759 sq.ft.	$950,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $5419 Airbnb ROI: N/A Traditional ROI: 3.14%
10 Todd Drive Middletown, NY Nestled in the heart of Middletown, NY, awaits an exquisite colonial-style residence at 10...	4 beds \| 3 baths \| 2,352 sq.ft.	$450,000	Airbnb cash on cash: 8.55% Traditional cash on cash: 5.76% Airbnb Rental Income: $6131 Traditional Rental Income: $3747 Airbnb ROI: 8.55% Traditional ROI: 5.76%
125 Overhill Road Middletown, NY Explore the perfect blend of comfort and convenience at 125 Overhill Rd. in Middletown, Ne...	3 beds \| 1 baths \| 1,408 sq.ft.	$299,000	Airbnb cash on cash: 9.14% Traditional cash on cash: 5.38% Airbnb Rental Income: $4464 Traditional Rental Income: $2472 Airbnb ROI: 9.14% Traditional ROI: 5.38%
335 Shawangunk Road Middletown, NY Welcome to your dream home! Nestled in a serene, park-like atmosphere, this stunning 5-bed...	5 beds \| 3 baths \| 2,660 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.61% Airbnb Rental Income: $null Traditional Rental Income: $4167 Airbnb ROI: N/A Traditional ROI: 6.61%
53 Richmond Place Middletown, NY	3 beds \| 1 baths \| 1,144 sq.ft.	$290,000	Airbnb cash on cash: 9.78% Traditional cash on cash: 5.36% Airbnb Rental Income: $4464 Traditional Rental Income: $2324 Airbnb ROI: 9.78% Traditional ROI: 5.36%
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%
13 Canterbury Drive Middletown, NY Welcome Home to this unusually oversized large almost 2700 sq ft home. Upon entering a lov...	4 beds \| 2 baths \| 2,668 sq.ft.	$469,999	Airbnb cash on cash: 7.22% Traditional cash on cash: 4.43% Airbnb Rental Income: $5817 Traditional Rental Income: $3432 Airbnb ROI: 7.22% Traditional ROI: 4.43%
1097 W Route 211 Middletown, NY Welcome to this gorgeous, NEW construction ready to move in 2100+ sqft single-family home ...	4 beds \| 3 baths \| 2,101 sq.ft.	$575,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 3.43% Airbnb Rental Income: $5817 Traditional Rental Income: $3526 Airbnb ROI: 5.54% Traditional ROI: 3.43%
225 Upper Road Middletown, NY Here we have a raised ranch style home, located on a 1.4 acre lot. The home is located in...	2 beds \| 2 baths \| 1,200 sq.ft.	$278,250	Airbnb cash on cash: 5.08% Traditional cash on cash: 5.35% Airbnb Rental Income: $3101 Traditional Rental Income: $2467 Airbnb ROI: 5.08% Traditional ROI: 5.35%
7 Forest Avenue #9 Middletown, NY This 4 bedrooms, 2 bathrooms Capecod offers lots of space for the entire household. The fi...	4 beds \| 2 baths \| 1,883 sq.ft.	$399,900	Airbnb cash on cash: 9.24% Traditional cash on cash: 5.54% Airbnb Rental Income: $5817 Traditional Rental Income: $3271 Airbnb ROI: 9.24% Traditional ROI: 5.54%
24 Kirbytown Road Middletown, NY *Accepted Offer* Spacious 3 bedrooms, 1.5 bathrooms, 2 car garage Capecod. Home offers...	3 beds \| 2 baths \| 1,536 sq.ft.	$339,900	Airbnb cash on cash: 8.18% Traditional cash on cash: 6.29% Airbnb Rental Income: $4464 Traditional Rental Income: $2926 Airbnb ROI: 8.18% Traditional ROI: 6.29%

Your search for investment property begins and ends here

Single Family Homes for Sale in Middletown, NY

179 Reservoir Road

Middletown, NY

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%

214 Brown Road

Middletown, NY

3 beds | 4 baths | 2,240 sq.ft.

$695,000

Airbnb cash on cash: 3.12%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $4661

Traditional Rental Income: $3765

Airbnb ROI: 3.12%

Traditional ROI: 3.23%

600 Goshen Turnpike

Middletown, NY

3 beds | 3 baths | 2,000 sq.ft.

$490,000

Airbnb cash on cash: 5.01%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $4661

Traditional Rental Income: $3278

Airbnb ROI: 5.01%

Traditional ROI: 4.1%

19 W Conkling Avenue

Middletown, NY

2 beds | 1 baths | 840 sq.ft.

$299,900

Airbnb cash on cash: 5.39%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $3101

Traditional Rental Income: $2190

Airbnb ROI: 5.39%

Traditional ROI: 4.66%

24 Rhode Island Avenue

Middletown, NY

2 beds | 2 baths | 1,248 sq.ft.

$249,900

Airbnb cash on cash: 7.01%

Traditional cash on cash: 6%

Airbnb Rental Income: $3101

Traditional Rental Income: $2157

Airbnb ROI: 7.01%

Traditional ROI: 6%

18 Pennsylvania Avenue

Middletown, NY

3 beds | 2 baths | 1,008 sq.ft.

$350,000

Airbnb cash on cash: 7.84%

Traditional cash on cash: 5.02%

Airbnb Rental Income: $4464

Traditional Rental Income: $2601

Airbnb ROI: 7.84%

Traditional ROI: 5.02%

25 Meyer Road

Middletown, NY

3 beds | 2 baths | 1,335 sq.ft.

$390,000

Airbnb cash on cash: 6.84%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $4464

Traditional Rental Income: $3056

Airbnb ROI: 6.84%

Traditional ROI: 5.54%

26 Mills Avenue

Middletown, NY

5 beds | 3 baths | 2,200 sq.ft.

$319,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.9%

Airbnb Rental Income: $null

Traditional Rental Income: $3675

Airbnb ROI: N/A