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 |
|---|---|---|---|
31 Bendlin LaneMiddletown, NYSituated on its own road in the sought after Minisink Valley School District, this 3 bedro... |
3 beds | 2 baths | 2,024 sq.ft. |
$529,999 |
Airbnb cash on cash: -0.33%
|
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. |
$333,000 |
Airbnb cash on cash: 1.08%
|
1 Brewster DriveMiddletown, NYWelcome to this beautiful 3 bedrooms with one-and-a-half-bath bi-level home nestled in a h... |
3 beds | 2 baths | 2,014 sq.ft. |
$499,000 |
Airbnb cash on cash: -0.95%
|
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%
|
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%
|
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: 0.21%
|
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%
|
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: 1.23%
|
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%
|
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. |
$399,900 |
Airbnb cash on cash: -0.6%
|
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. |
$160,000 |
Airbnb cash on cash: -5.57%
|
89 Prince StreetMiddletown, NYThere is a particular kind of quiet that arrives when a place becomes yours. The last box ... |
2 beds | 2 baths | 1,008 sq.ft. |
$329,900 |
Airbnb cash on cash: 0.07%
|
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: -0.38%
|
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: -2.69%
|
488 Tally Ho RoadMiddletown, NYA charming 1940 bungalow located in the highly desirable Minisink Valley School District, ... |
1 beds | 1 baths | 748 sq.ft. |
$175,000 |
Airbnb cash on cash: -1.61%
|
37 Meadow View DriveMiddletown, NYWelcome to this beautifully updated end-unit townhouse with numerous upgrades completed in... |
3 beds | 3 baths | 1,781 sq.ft. |
$499,900 |
Airbnb cash on cash: -1.21%
|
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%
|
255 Howells RoadMiddletown, NYEnter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom,... |
5 beds | 5 baths | 4,200 sq.ft. |
$899,000 |
Airbnb cash on cash: -0.31%
|
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%
|
744 Mt Hope RoadMiddletown, NYWelcome to this stunning new Colonial home, currently under construction and set on approx... |
4 beds | 3 baths | 2,400 sq.ft. |
$629,000 |
Airbnb cash on cash: 0.64%
|
8 Green CourtMiddletown, NYWelcome to this well-maintained 3-level townhome in The Fairways, a gated community conven... |
3 beds | 3 baths | 2,548 sq.ft. |
$625,000 |
Airbnb cash on cash: -1.31%
|
19 Randall TerraceMiddletown, NYSTUNNING Colonial located in a quiet neighborhood of Middletown minutes from OCC. This hom... |
4 beds | 4 baths | 2,088 sq.ft. |
$535,000 |
Airbnb cash on cash: 1.59%
|
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: -0.77%
|
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%
|
13 Forest AvenueMiddletown, NYFresh 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%
|
238 S Centerville RoadMiddletown, NYSpacious 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: -0.43%
|
2078 Route 6Middletown, NYWelcome to this beautifully maintained contemporary bi-level home set on 2.2 private acres... |
3 beds | 3 baths | 1,332 sq.ft. |
$560,000 |
Airbnb cash on cash: -0.64%
|
29 Parsons LaneMiddletown, NYEndless 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%
|
1 Hulse StreetMiddletown, NY"NEW CONSTRUCTION!" Stunning corner-lot home in a calm suburban setting with beautiful mou... |
4 beds | 3 baths | 2,344 sq.ft. |
$525,000 |
Airbnb cash on cash: 1.61%
|
45 Knapp AvenueMiddletown, NYAttention 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: -1.05%
|
35 Dogwood DriveMiddletown, NYJust pack your bags and move in. Spacious, Comfortable and Cozy 5 bedroom 1 family house f... |
5 beds | 4 baths | 1,911 sq.ft. |
$550,000 |
Airbnb cash on cash: 0.25%
|
1 High Ridge LaneMiddletown, NYWelcome to refined, low maintenance living in one of Middletown's most sought after gated ... |
3 beds | 3 baths | 2,084 sq.ft. |
$485,000 |
Airbnb cash on cash: 0.18%
|
15 N Aspen RoadMiddletown, NYNO HOA FEES! LOW TAXES!! Welcome to easy, effortless living in this turnkey, move-in ready... |
2 beds | 2 baths | 1,144 sq.ft. |
$329,000 |
Airbnb cash on cash: 0.75%
|
22 Atwood DriveMiddletown, NYComing Soon! Beautiful 3 BR, 2.5 baths. |
3 beds | 3 baths | 1,723 sq.ft. |
$470,000 |
Airbnb cash on cash: -0.33%
|
6 Charlotte MewsMiddletown, NYNew renovation, New split air conditioner,New floor ,NEW painting, New toilet on the first... |
3 beds | 2 baths | 1,413 sq.ft. |
$370,000 |
Airbnb cash on cash: 0.61%
|
Real Estate investment in Middletown, NY
There are 148 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 $183. In July 2026, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $3,091.