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 104 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 Warmth, comfort & space in the Hudson Valley. Welcome home to this spacious Colonial on 2....	3 beds \| 2 baths \| 3,080 sq.ft.	$599,900	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%
13 Brewster Drive Middletown, NY Welcome home to this beautifully updated 3-bedroom, 1-bath split-level offering approximat...	3 beds \| 1 baths \| 1,456 sq.ft.	$374,900	Airbnb cash on cash: -0.16% Traditional cash on cash: 3.35% Airbnb Rental Income: $1592 Traditional Rental Income: $2375 Airbnb ROI: -0.16% Traditional ROI: 3.35%
1 Brewster Drive Middletown, NY Welcome to this beautiful 3 bedrooms plus possibly an office or den, one-and-a-half-bath b...	3 beds \| 2 baths \| 2,014 sq.ft.	$499,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 3.9% Airbnb Rental Income: $1592 Traditional Rental Income: $3400 Airbnb ROI: -0.95% Traditional ROI: 3.9%
482 Scotchtown Avenue Middletown, NY Classic 1863 Farmhouse in Mint Condition - Riverfront Property in Goshen School District. ...	5 beds \| 3 baths \| 2,828 sq.ft.	$719,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $3892 Airbnb ROI: N/A Traditional ROI: 3.03%
5 Oak Ridge Road 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.	$587,000	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%
19 Hulse Avenue Middletown, NY Opportunities like this don't come around often! Welcome to 19 Hulse Avenue, a charming an...	2 beds \| 1 baths \| 1,200 sq.ft.	$279,000	Airbnb cash on cash: 7.6% Traditional cash on cash: 6.18% Airbnb Rental Income: $3402 Traditional Rental Income: $2271 Airbnb ROI: 7.6% Traditional ROI: 6.18%
217-219 Highland Avenue Middletown, NY Spacious and charming 3-bedroom, 2.5-bath home featuring a welcoming wraparound porch and ...	3 beds \| 3 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%
82 California Avenue Middletown, NY Welcome to 82 California Ave in Middletown, where flexibility, space, and everyday conveni...	4 beds \| 2 baths \| 1,376 sq.ft.	$375,000	Airbnb cash on cash: 3.1% Traditional cash on cash: 5.37% Airbnb Rental Income: $2881 Traditional Rental Income: $3011 Airbnb ROI: 3.1% Traditional ROI: 5.37%
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 \| 3 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%
512 County Route 49 Middletown, NY Welcome to this stunning, meticulously maintained Chesterfield Colonial offering breathtak...	4 beds \| 3 baths \| 2,906 sq.ft.	$749,900	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%
145 Wawayanda Avenue Middletown, NY Nestled in one of Middletown's most convenient residential neighborhoods. This property bl...	3 beds \| 2 baths \| 1,248 sq.ft.	$369,900	Airbnb cash on cash: 0.08% Traditional cash on cash: 4.71% Airbnb Rental Income: $1592 Traditional Rental Income: $2743 Airbnb ROI: 0.08% Traditional ROI: 4.71%
428 Prosperous Valley Road Middletown, NY Tucked away on 16 private acres, 428 Prosperous Valley Road offers the space, privacy, and...	3 beds \| 3 baths \| 2,678 sq.ft.	$725,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 2.4% Airbnb Rental Income: $1592 Traditional Rental Income: $3634 Airbnb ROI: -1.29% Traditional ROI: 2.4%
57 Boorman Road 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%
59 Woodside Knolls Drive Middletown, NY Welcome home to this impeccably maintained, tri-level townhouse nestled in the heart of th...	3 beds \| 3 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%
4 Hulse Street Middletown, NY Welcome to 4 Hulse Street, where charm, value, and convenience come together in one irresi...	2 beds \| 1 baths \| 806 sq.ft.	$289,000	Airbnb cash on cash: 7.58% Traditional cash on cash: 4.97% Airbnb Rental Income: $3402 Traditional Rental Income: $1936 Airbnb ROI: 7.58% Traditional ROI: 4.97%
53 Cornwall Lane Middletown, NY Beautifully renovated 3-bedroom, 3.5-bathroom townhouse with a 2-car garage, located in th...	3 beds \| 4 baths \| 2,521 sq.ft.	$483,900	Airbnb cash on cash: -1.03% Traditional cash on cash: 3.33% Airbnb Rental Income: $1592 Traditional Rental Income: $3114 Airbnb ROI: -1.03% Traditional ROI: 3.33%
225 Van Duzer Road Middletown, NY Discover A stunning Brand New Colonial Home over 3900 SQFT. This gorgeous home is now offe...	4 beds \| 4 baths \| 3,900 sq.ft.	$799,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 2.1% Airbnb Rental Income: $2881 Traditional Rental Income: $3676 Airbnb ROI: 0.14% Traditional ROI: 2.1%
60 Peach Place Middletown, NY Welcome to Swan Village Estates conveniently located just minutes from Highways, stores an...	3 beds \| 4 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 Street Middletown, NY Beautifully renovated 3 bedroom 1 bathroom, everything is brand new, electrical, plumbing ...	3 beds \| 1 baths \| 1,100 sq.ft.	$393,000	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%
225 Upper Road Middletown, NY Completely renovated ranch situated on 1.44 acres in the Minisink Valley School District. ...	3 beds \| 2 baths \| 2,065 sq.ft.	$525,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 2.44% Airbnb Rental Income: $1592 Traditional Rental Income: $2467 Airbnb ROI: -0.27% Traditional ROI: 2.44%
120 Prospect Avenue Middletown, NY Beautiful 1900 Colonial - Turnkey & Full of Character, blending historic detail with moder...	3 beds \| 2 baths \| 1,382 sq.ft.	$385,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 5.29% Airbnb Rental Income: $1592 Traditional Rental Income: $2895 Airbnb ROI: 0.42% Traditional ROI: 5.29%
580 Van Burenville Road Middletown, NY Welcome to 580 Van Burenville Rd.	3 beds \| 1 baths \| 1,056 sq.ft.	$299,900	Airbnb cash on cash: 0.93% Traditional cash on cash: 5.63% Airbnb Rental Income: $1592 Traditional Rental Income: $2464 Airbnb ROI: 0.93% Traditional ROI: 5.63%
744 Mt Hope Road Middletown, NY Welcome to this stunning new Colonial home, currently under construction and set on approx...	4 beds \| 3 baths \| 2,600 sq.ft.	$629,000	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%
29 Beth Drive Middletown, NY Welcome to this spacious raised ranch in Scotchtown neighborhood within the highly sought-...	4 beds \| 2 baths \| 1,716 sq.ft.	$525,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 4.26% Airbnb Rental Income: $2881 Traditional Rental Income: $3262 Airbnb ROI: 2.12% Traditional ROI: 4.26%
4 Eaton Court Middletown, NY Welcome to Canterbury Knolls! This beautifully maintained 3-bedroom, 1.5-bathroom home is ...	3 beds \| 2 baths \| 1,470 sq.ft.	$375,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 5.66% Airbnb Rental Income: $1592 Traditional Rental Income: $2879 Airbnb ROI: 0.71% Traditional ROI: 5.66%
6 Eaton Court Middletown, NY This end unit Townhouse located in the Desirable Canterbury Knolls just took an interior r...	3 beds \| 2 baths \| 1,248 sq.ft.	$384,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 4.1% Airbnb Rental Income: $1592 Traditional Rental Income: $2608 Airbnb ROI: 0.02% Traditional ROI: 4.1%
13 Forest Avenue Middletown, NY Fresh updates. New improvements. New opportunity. 13 Forest Avenue is officially back on t...	3 beds \| 2 baths \| 1,748 sq.ft.	$449,000	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%
17 Woodrose Court Middletown, NY Discover the perfect blend of classic charm and modern comfort in this beautiful Colonial-...	3 beds \| 3 baths \| 2,763 sq.ft.	$505,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 4.18% Airbnb Rental Income: $1592 Traditional Rental Income: $3664 Airbnb ROI: -1.17% Traditional ROI: 4.18%
238 S Centerville Road Middletown, NY Spacious Country Retreat on 22.6 Acres in Minisink Valley School District This exceptional...	5 beds \| 3 baths \| 3,764 sq.ft.	$844,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.87% Airbnb Rental Income: $null Traditional Rental Income: $4257 Airbnb ROI: N/A Traditional ROI: 2.87%
50 Brola Road Middletown, NY Bring your vision to life at 50 Brola Road. Perfectly situated in the picturesque countrys...	3 beds \| 1 baths \| 1,196 sq.ft.	$325,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 4.83% Airbnb Rental Income: $1592 Traditional Rental Income: $2461 Airbnb ROI: 0.5% Traditional ROI: 4.83%
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.	$585,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 2.68% Airbnb Rental Income: $1592 Traditional Rental Income: $2958 Airbnb ROI: -0.66% Traditional ROI: 2.68%
32 Woodstock Lane Middletown, NY Charming 3 bedroom, 2.5 bath home close to everything with Pine Bush Schools! Perfectly po...	3 beds \| 3 baths \| 2,198 sq.ft.	$479,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 4.72% Airbnb Rental Income: $1592 Traditional Rental Income: $3506 Airbnb ROI: -0.56% Traditional ROI: 4.72%
11 Philcox Road 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.	$260,000	Airbnb cash on cash: 8.4% Traditional cash on cash: 6.2% Airbnb Rental Income: $3402 Traditional Rental Income: $2106 Airbnb ROI: 8.4% Traditional ROI: 6.2%
21 Philcox Road Middletown, NY Rare opportunity to own two homes next door to each other in the Pine Bush School District...	3 beds \| 2 baths \| 1,314 sq.ft.	$379,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 4.64% Airbnb Rental Income: $1592 Traditional Rental Income: $2680 Airbnb ROI: 0.31% Traditional ROI: 4.64%
331 Highland Ave Extension Middletown, NY Tucked away on approximately .40 peaceful acres in the Town of Wallkill, just outside the ...	1 beds \| 2 baths \| 960 sq.ft.	$259,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 6.72% Airbnb Rental Income: $657 Traditional Rental Income: $2317 Airbnb ROI: -1.3% Traditional ROI: 6.72%
5 Loch Invar Lane Middletown, NY .	3 beds \| 2 baths \| 1,646 sq.ft.	$369,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 5.98% Airbnb Rental Income: $1592 Traditional Rental Income: $3158 Airbnb ROI: 0.14% Traditional ROI: 5.98%
29 Parsons Lane Middletown, NY Endless Potential - Discover the possibilities at 29 Parsons Lane - a private country prop...	4 beds \| 1 baths \| 1,140 sq.ft.	$259,999	Airbnb cash on cash: 6.69% Traditional cash on cash: 8.67% Airbnb Rental Income: $2881 Traditional Rental Income: $2698 Airbnb ROI: 6.69% Traditional ROI: 8.67%
28 Magnolia Park Middletown, NY Lifestyle and Location without all the work- this home has all the perks of homeownership ...	3 beds \| 3 baths \| 2,211 sq.ft.	$490,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 3.96% Airbnb Rental Income: $1592 Traditional Rental Income: $3587 Airbnb ROI: -1.38% Traditional ROI: 3.96%
1 Hulse Street Middletown, NY "NEW CONSTRUCTION!" Stunning corner-lot home in a calm suburban setting with beautiful mou...	4 beds \| 3 baths \| 2,344 sq.ft.	$550,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 4.8% Airbnb Rental Income: $2881 Traditional Rental Income: $3948 Airbnb ROI: 1.42% Traditional ROI: 4.8%
45 Knapp Avenue Middletown, NY Attention investors! This is a true "what you see is what you get" opportunity. Bring your...	1 beds \| 1 baths \| 784 sq.ft.	$155,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 8.89% Airbnb Rental Income: $657 Traditional Rental Income: $1751 Airbnb ROI: -0.51% Traditional ROI: 8.89%

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.

$599,900

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%

13 Brewster Drive

Middletown, NY

3 beds | 1 baths | 1,456 sq.ft.

$374,900

Airbnb cash on cash: -0.16%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $1592

Traditional Rental Income: $2375

Airbnb ROI: -0.16%

Traditional ROI: 3.35%

1 Brewster Drive

Middletown, NY

3 beds | 2 baths | 2,014 sq.ft.

$499,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $1592

Traditional Rental Income: $3400

Airbnb ROI: -0.95%

Traditional ROI: 3.9%

482 Scotchtown Avenue

Middletown, NY

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

$719,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.03%

Airbnb Rental Income: $null

Traditional Rental Income: $3892

Airbnb ROI: N/A

Traditional ROI: 3.03%

5 Oak Ridge Road

Middletown, NY

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

$587,000

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%

19 Hulse Avenue

Middletown, NY

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

$279,000

Airbnb cash on cash: 7.6%

Traditional cash on cash: 6.18%

Airbnb Rental Income: $3402

Traditional Rental Income: $2271

Airbnb ROI: 7.6%

Traditional ROI: 6.18%

217-219 Highland Avenue

Middletown, NY

3 beds | 3 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%

82 California Avenue

Middletown, NY

4 beds | 2 baths | 1,376 sq.ft.

$375,000

Airbnb cash on cash: 3.1%

Traditional cash on cash: 5.37%

Airbnb Rental Income: $2881

Traditional Rental Income: $3011

Airbnb ROI: 3.1%