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. |
$620,000 |
Airbnb cash on cash: -1.21%
|
14 Kensington WayMiddletown, NYWelcome to this beautifully renovated townhouse-style condo offering 2 bedrooms and 1.5 ba... |
2 beds | 2 baths | 1,115 sq.ft. |
$359,000 |
Airbnb cash on cash: 1.05%
|
295 Lybolt RoadMiddletown, NYA/O 9.1.25 ... Spacious home with large yard on a quiet street - what more could you want?... |
3 beds | 2 baths | 1,222 sq.ft. |
$470,000 |
Airbnb cash on cash: -0.63%
|
115 Vincent DriveMiddletown, NYCheck 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: -1.42%
|
482 Scotchtown AvenueMiddletown, NYClassic 1863 Farmhouse in Mint Condition - Riverfront Property in Goshen School District. ... |
5 beds | 3 baths | 2,828 sq.ft. |
$759,000 |
Airbnb cash on cash: N/A
|
24 Kent CourtMiddletown, NYElegant 2-Bedroom, 3-Bath End Unit in Sought-After Waters Edge Community Welcome to this b... |
2 beds | 3 baths | 1,241 sq.ft. |
$325,000 |
Airbnb cash on cash: 0.27%
|
5 Raleigh CloseMiddletown, NYCANTERBURY KNOLLS of Wallkill now offers this GORGEOUS TURN-KEY Contemporary style home ju... |
3 beds | 2 baths | 1,608 sq.ft. |
$375,000 |
Airbnb cash on cash: -0.56%
|
5 Peace DriveMiddletown, NYCommuter'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: 0%
|
77 Prince StreetMiddletown, NYWelcome to this beautiful well maintained contemporary two story home nestled in the heart... |
3 beds | 3 baths | 1,245 sq.ft. |
$399,000 |
Airbnb cash on cash: -0.56%
|
21 Ridge StreetMiddletown, NYDon't miss this 4-bedroom, 2-bath Colonial located in the City of Middletown near Touro Co... |
4 beds | 2 baths | 1,998 sq.ft. |
$310,000 |
Airbnb cash on cash: 2.28%
|
44 Houston AvenueMiddletown, NYVacant and sold as-is. Inspections for informational purposes only. Prior buyer could not ... |
5 beds | 2 baths | N/A |
$369,900 |
Airbnb cash on cash: N/A
|
350 Concord LaneMiddletown, NYWelcome to this beautiful 2-bedroom, 2-bathroom condo located in the heart of Middletown, ... |
2 beds | 2 baths | 955 sq.ft. |
$213,999 |
Airbnb cash on cash: -0.65%
|
171 High Barney RoadMiddletown, NYWelcome to 171 High Barney a charming three-bedroom, two-bath home tucked away on a quiet ... |
3 beds | 2 baths | 2,056 sq.ft. |
$469,000 |
Airbnb cash on cash: -0.61%
|
565 Prosperous Valley RoadMiddletown, NYYour 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: -0.77%
|
6 Tice LaneMiddletown, NYSet 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: -0.63%
|
121 Sprague AvenueMiddletown, NYWelcome to this inviting 1,200 sq. ft. Cape Cod-style home offering 2 bedrooms and 1.5 bat... |
2 beds | 2 baths | 1,200 sq.ft. |
$274,900 |
Airbnb cash on cash: 1.24%
|
24 Edinburgh RoadMiddletown, NYLooking for something different? This spacious 4 bedroom 2 full bath contemporary raised r... |
4 beds | 2 baths | 1,796 sq.ft. |
$345,000 |
Airbnb cash on cash: 2.16%
|
55 Hulse AvenueMiddletown, NYTown of Wallkill now offers your starter home that can turn into that turn-key investment ... |
3 beds | 1 baths | 914 sq.ft. |
$345,000 |
Airbnb cash on cash: 0.79%
|
8 EburyMiddletown, NYBeautiful 4-Bedroom Home in Canterbury Knolls - Town of Wallkill Welcome to this spacious ... |
4 beds | 3 baths | 1,505 sq.ft. |
$368,800 |
Airbnb cash on cash: 1.84%
|
2 Rivervale RoadMiddletown, NYCharming Corner Townhouse in Middletown - No HOA Fees! Welcome to 2 Riverdale Road, a deli... |
3 beds | 2 baths | 1,484 sq.ft. |
$330,000 |
Airbnb cash on cash: 0.25%
|
17 N Aspen RoadMiddletown, NYThis renovated 2-bedroom, 1.5-bath townhouse in Middletown offers a perfect blend of comfo... |
2 beds | 2 baths | 1,144 sq.ft. |
$258,000 |
Airbnb cash on cash: 1.16%
|
105 Sheffield DriveMiddletown, NYTown 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: 0.72%
|
43 Woodside Knolls DriveMiddletown, NYThis exceptional property at 43 Woodside Knolls, Middletown, NY 10940 offers an effortless... |
3 beds | 3 baths | 2,521 sq.ft. |
$499,000 |
Airbnb cash on cash: -1.05%
|
30 Daly RoadMiddletown, NYNew Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partiall... |
3 beds | 3 baths | 2,205 sq.ft. |
$579,900 |
Airbnb cash on cash: -1.05%
|
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 |
$1,298,000 |
Airbnb cash on cash: -2.17%
|
48 Beacon StreetMiddletown, NYWell-maintained two-family property in the heart of Middletown offering flexibility for ow... |
6 beds | 2 baths | N/A |
$380,000 |
Airbnb cash on cash: N/A
|
147 Ruth CourtMiddletown, NYWelcome to this beautifully maintained 2-bedroom, 2-bathroom condo in Middletown! Featurin... |
2 beds | 2 baths | 880 sq.ft. |
$269,900 |
Airbnb cash on cash: 0.78%
|
91 Mountain AvenueMiddletown, NYLooking for one-story living in a private dead end street, look no further as you have fou... |
3 beds | 1 baths | 892 sq.ft. |
$350,000 |
Airbnb cash on cash: 0.43%
|
242 Derby RoadMiddletown, NYWelcome to 242 Derby Road. |
3 beds | 3 baths | 2,214 sq.ft. |
$419,900 |
Airbnb cash on cash: 0.56%
|
168 S Centerville RoadMiddletown, NYThis is one of the Kind property in the Minisink School District . This Beautiful Colonial... |
4 beds | 3 baths | 3,088 sq.ft. |
$668,900 |
Airbnb cash on cash: 0.01%
|
78 Commonwealth AvenueMiddletown, NYLuxury Post & Beam Contemporary Home with Pool, Gardens & Private Elevator Experience time... |
3 beds | 3 baths | 2,108 sq.ft. |
$558,000 |
Airbnb cash on cash: -1.19%
|
47 Prince StreetMiddletown, NYWelcome 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: 2.47%
|
488 Tally Ho RoadMiddletown, NYA charming 1940 bungalow located in the highly desirable Minisink Valley School District, ... |
1 beds | 1 baths | 748 sq.ft. |
$215,000 |
Airbnb cash on cash: 0.05%
|
104 Elise DriveMiddletown, NYLAST HOME AVAILABLE! Welcome to The Woodlands at Scotchtown Estates! This exquisite pictur... |
5 beds | 4 baths | 3,700 sq.ft. |
$799,000 |
Airbnb cash on cash: N/A
|
71 Commonwealth AvenueMiddletown, NYWelcome to the perfect blend of comfort, character, and location. Nestled in the vibrant h... |
3 beds | 1 baths | 1,344 sq.ft. |
$360,000 |
Airbnb cash on cash: -0.39%
|
225 Van Duzer RoadMiddletown, NYWelcome to a stunning brand new Colonial Home nestled in the heart of the town of Wallkill... |
4 beds | 3 baths | 3,900 sq.ft. |
$749,900 |
Airbnb cash on cash: -0.34%
|
145 Academy AvenueMiddletown, NYCome tour this LOVELY NEWLY REMODELED Middletown Colonial!! This 4 bedroom home is in turn... |
4 beds | 2 baths | 2,545 sq.ft. |
$445,000 |
Airbnb cash on cash: 1.66%
|
390 Hufcut RoadMiddletown, NYLight-filled home offering peace & serenity situated on a large, flat grassy lot. This war... |
2 beds | 1 baths | 1,142 sq.ft. |
$379,000 |
Airbnb cash on cash: 0.67%
|
42 Genung StreetMiddletown, NYBEAUTIFUL turn-key home located in MIDDLETOWN! Do NOT let the ouside fool you as this home... |
4 beds | 3 baths | 1,728 sq.ft. |
$425,000 |
Airbnb cash on cash: 1.78%
|
53 Richmond PlaceMiddletown, NYBeautifully renovated two-story home in Orange County! Featuring a brand-new kitchen with ... |
3 beds | 1 baths | 1,144 sq.ft. |
$349,999 |
Airbnb cash on cash: 0.26%
|
Real Estate investment in Middletown, NY
There are 147 properties for sale in the city of Middletown . The median list price in Middletown is $410,000 and the average price per square foot is $206. In January 2026, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $3,013.