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. |
$349,000 |
Airbnb cash on cash: 0.26%
|
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. |
$749,000 |
Airbnb cash on cash: N/A
|
47 Brick Pond RoadMiddletown, NYWelcome to this charming 2-story townhouse-style condo nestled in the Spring Hollow commun... |
2 beds | 2 baths | 1,460 sq.ft. |
$318,000 |
Airbnb cash on cash: -0.41%
|
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%
|
599 Guymard TurnpikeMiddletown, NYTIMELESS ELEGANCE - MODERN COMFORT - EFFORTLESS LIVING Nestled within the highly regarded ... |
3 beds | 2 baths | 1,852 sq.ft. |
$499,000 |
Airbnb cash on cash: -0.82%
|
65 Monhagen AvenueMiddletown, NYThis beautifully updated Cape Cod-style single-family home offers 3 bedrooms and 2.5 baths... |
3 beds | 3 baths | 930 sq.ft. |
$350,000 |
Airbnb cash on cash: 0.01%
|
57 Boorman RoadMiddletown, NYThis nicely renovated Dutch Colonial is located on 5+ acres surrounded by mature trees jus... |
3 beds | 3 baths | 2,074 sq.ft. |
$475,000 |
Airbnb cash on cash: -0.57%
|
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%
|
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. |
$330,000 |
Airbnb cash on cash: 2.3%
|
55 Hulse AvenueMiddletown, NYCute as a Button! Town of Wallkill now offers this starter home that can turn into that tu... |
3 beds | 1 baths | 914 sq.ft. |
$335,000 |
Airbnb cash on cash: 0.85%
|
572 Greenville TurnpikeMiddletown, NYSet back from the road, where life feels just a little more private and peaceful, there is... |
4 beds | 4 baths | 2,072 sq.ft. |
$570,000 |
Airbnb cash on cash: 0.19%
|
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: -1.27%
|
14 Rdean PlaceMiddletown, NYNestled in a quiet Residential neighborhood of Middletown sits this spacious 3 bedroom, 2.... |
3 beds | 3 baths | 2,016 sq.ft. |
$499,000 |
Airbnb cash on cash: -1.54%
|
164 Brookline AvenueMiddletown, NYMove-in ready 3-bedroom home featuring a great blend of updates and classic charm. Enjoy p... |
3 beds | 1 baths | 1,050 sq.ft. |
$350,000 |
Airbnb cash on cash: 0.4%
|
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%
|
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. |
$335,000 |
Airbnb cash on cash: -0.31%
|
43 Woodside Knolls DriveMiddletown, NY?? FHA & VA Approved | Move-In Ready 3BR/2.5BA Townhouse | Woodside Knolls Welcome to this... |
3 beds | 3 baths | 2,521 sq.ft. |
$493,000 |
Airbnb cash on cash: -1.12%
|
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. |
$579,990 |
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 |
$1,298,800 |
Airbnb cash on cash: -2.17%
|
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%
|
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: -1.32%
|
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%
|
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: -0.18%
|
86 Linden AvenueMiddletown, NYThe possibilities are ENDLESS with this one. Come check out the biggest bang for your buck... |
4 beds | 1 baths | 1,316 sq.ft. |
$299,999 |
Airbnb cash on cash: 3.39%
|
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, NYMiddletown Gem: Updated Home, Unbeatable Location, Finally Priced Right. Welcome to 70 mil... |
3 beds | 1 baths | 1,344 sq.ft. |
$330,000 |
Airbnb cash on cash: -0.34%
|
19 Red Barn LaneMiddletown, NYInvestment Opportunity! This conveniently located 3-level townhouse. Located on a cul de s... |
4 beds | 4 baths | 1,692 sq.ft. |
$369,000 |
Airbnb cash on cash: 2.08%
|
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%
|
Real Estate investment in Middletown, NY
There are 151 properties for sale in the city of Middletown . The median list price in Middletown is $399,900 and the average price per square foot is $198. In March 2026, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $2,744.