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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
179 Reservoir RoadMiddletown, NYWarmth, 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%
|
5 Kendal LaneMiddletown, NYModern Comfort & Lake Access - The Best of Waters Edge! Welcome to this beautifully mainta... |
2 beds | 3 baths | 1,241 sq.ft. |
$337,000 |
Airbnb cash on cash: 6.12%
|
13 Brewster DriveMiddletown, NYWelcome 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%
|
1 Brewster DriveMiddletown, NYWelcome 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%
|
482 Scotchtown AvenueMiddletown, NYClassic 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
|
5 Oak Ridge RoadMiddletown, NYBuilt 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%
|
19 Hulse AvenueMiddletown, NYOpportunities 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%
|
217-219 Highland AvenueMiddletown, NYSpacious 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%
|
47 Brick Pond RoadMiddletown, NYWelcome to this charming 2-story townhouse-style condo located in the Spring Hollow commun... |
2 beds | 2 baths | 1,460 sq.ft. |
$315,000 |
Airbnb cash on cash: 4.93%
|
82 California AvenueMiddletown, NYWelcome 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%
|
568 County Route 49 #2CMiddletown, NYPrivately 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%
|
15 Kendal LaneMiddletown, NYBeautifully maintained end-unit townhouse in the highly desirable Water's Edge community! ... |
2 beds | 3 baths | 1,241 sq.ft. |
$349,000 |
Airbnb cash on cash: 5.1%
|
512 County Route 49Middletown, NYWelcome 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%
|
145 Wawayanda AvenueMiddletown, NYNestled 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%
|
428 Prosperous Valley RoadMiddletown, NYTucked 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%
|
129 Concord LaneMiddletown, NYAn exceptional opportunity for homeowners and savvy investors, this sun-drenched, southeas... |
2 beds | 2 baths | 1,230 sq.ft. |
$259,000 |
Airbnb cash on cash: 7.79%
|
57 Boorman RoadMiddletown, NYRenovated 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%
|
215 Linden AvenueMiddletown, NYExcellent investment opportunity in the City of Middletown! This well-maintained duplex fe... |
6 beds | 2 baths | N/A |
$599,900 |
Airbnb cash on cash: N/A
|
83 Deer Ct DriveMiddletown, NYBeautifully renovated 3-bedroom, 2.5-bathroom, 1-car garage, two-story townhouse located i... |
3 beds | 3 baths | 1,919 sq.ft. |
$425,000 |
Airbnb cash on cash: -0.62%
|
59 Woodside Knolls DriveMiddletown, NYWelcome 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%
|
226 Concord LaneMiddletown, NYRenovated in 2021 is this first floor 1 bedroom condo in Buttonwood conveniently located c... |
1 beds | 1 baths | 735 sq.ft. |
$165,000 |
Airbnb cash on cash: -4.92%
|
38 Putters WayMiddletown, NYWell-maintained 3-bedroom, 2.5-bath townhome with a finished basement in the gated communi... |
3 beds | 3 baths | 3,013 sq.ft. |
$615,000 |
Airbnb cash on cash: -1.25%
|
4 Hulse StreetMiddletown, NYWelcome 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%
|
51 Deer Ct DriveMiddletown, NYWelcome to this townhouse-style condo in Middletown, offering 2 bedrooms and 2.5 bathrooms... |
2 beds | 3 baths | 1,473 sq.ft. |
$333,000 |
Airbnb cash on cash: 4.74%
|
1 Royal Acres DriveMiddletown, NYOne-of-a-kind 7-building residential rental property with 36 acres of land in the town of ... |
N/A beds | N/A baths | N/A |
$1,399,000 |
Airbnb cash on cash: -2.23%
|
36 Wallkill AvenueMiddletown, NYExcellent 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: -2.86%
|
53 Cornwall LaneMiddletown, NYBeautifully 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%
|
18 Jordan LaneMiddletown, NYMountainside Hills in Middletown offers this townhouse-style condo featuring 3 bedrooms an... |
3 beds | 3 baths | 1,345 sq.ft. |
$359,000 |
Airbnb cash on cash: 0.2%
|
225 Van Duzer RoadMiddletown, NYDiscover 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%
|
60 Peach PlaceMiddletown, NYWelcome 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%
|
1 Chestnut StreetMiddletown, NYBeautifully 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%
|
225 Upper RoadMiddletown, NYCompletely 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%
|
2 S Aspen RoadMiddletown, NYSay hello to possibility! A Middletown townhouse with space, flexibility, and room to make... |
3 beds | 2 baths | 1,884 sq.ft. |
$299,900 |
Airbnb cash on cash: 0.52%
|
120 Prospect AvenueMiddletown, NYBeautiful 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%
|
580 Van Burenville RoadMiddletown, NYWelcome to 580 Van Burenville Rd. |
3 beds | 1 baths | 1,056 sq.ft. |
$299,900 |
Airbnb cash on cash: 0.93%
|
744 Mt Hope RoadMiddletown, NYWelcome 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%
|
29 Beth DriveMiddletown, NYWelcome 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%
|
34 Poplar LaneMiddletown, NYThis well-maintained home offers comfort, space, and convenience in a desirable location c... |
2 beds | 2 baths | 1,240 sq.ft. |
$250,000 |
Airbnb cash on cash: 6.89%
|
326 Concord LaneMiddletown, NYPRICED TO SELL!!! Buttonwood Hills Condominiums now offers a 2 bedroom/2 bath unit for you... |
2 beds | 2 baths | 924 sq.ft. |
$185,000 |
Airbnb cash on cash: 8.34%
|
4 Eaton CourtMiddletown, NYWelcome 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%
|
Real Estate investment in Middletown, NY
There are 135 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 $182. In July 2026, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $3,096.