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 RdMiddletown, 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 | 1 baths | 1,115 sq.ft. |
$349,000 |
Airbnb cash on cash: 1.05%
|
65 Monhagen AveMiddletown, NYThis beautifully updated Cape Cod-style single-family home offers 3 bedrooms and 2.5 baths... |
3 beds | 2 baths | 930 sq.ft. |
$350,000 |
Airbnb cash on cash: 0.01%
|
57 Boorman RdMiddletown, NYHOT Deal Alert: This property deal has a high potential return. Make sure you strike while... |
3 beds | 3 baths | 1,674 sq.ft. |
$475,000 |
Airbnb cash on cash: -0.39%
|
171 High Barney RdMiddletown, 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 RdMiddletown, NYYour dream countryside retreat located in Orange County NY. This custom-built 4,000 sq. ft... |
4 beds | 2 baths | 4,000 sq.ft. |
$1,600,000 |
Airbnb cash on cash: -0.77%
|
22 Red Barn LnMiddletown, NYInvestor opportunity! This property is being offered at Public Auction on 09-23-2019. Visi... |
3 beds | 2 baths | 1,408 sq.ft. |
$319,000 |
Airbnb cash on cash: -0.1%
|
121 Sprague AveMiddletown, NYWelcome to this inviting 1,200 sq. ft. Cape Cod-style home offering 2 bedrooms and 1.5 bat... |
2 beds | 1 baths | 1,200 sq.ft. |
$274,900 |
Airbnb cash on cash: 1.24%
|
55 Hulse AveMiddletown, NYTown of Wallkill now offers your starter home that can turn into that turn-key investment ... |
3 beds | 1 baths | 914 sq.ft. |
$335,000 |
Airbnb cash on cash: 0.79%
|
2 Rivervale RdMiddletown, 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%
|
43 Woodside Knolls DrMiddletown, NYThis exceptional property at 43 Woodside Knolls, Middletown, NY 10940 offers an effortless... |
3 beds | 2 baths | 2,521 sq.ft. |
$499,000 |
Airbnb cash on cash: -1.05%
|
30 Daly RdMiddletown, NYNew Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partiall... |
3 beds | 2 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 |
$1,298,000 |
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 AveMiddletown, 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%
|
71 Commonwealth AveMiddletown, NYWelcome to the perfect blend of comfort, character, and location. Nestled in the vibrant h... |
3 beds | 1 baths | 1,344 sq.ft. |
$330,000 |
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%
|
9 Genung StMiddletown, NYCharming two-story home in the heart of Middletown! This spacious residence offers a welco... |
3 beds | 2 baths | 1,240 sq.ft. |
$314,999 |
Airbnb cash on cash: 0.58%
|
9 Fairview AveMiddletown, NYA must see home! This beautiful colonial home will have everything brand new - from the ex... |
3 beds | 2 baths | 1,056 sq.ft. |
$319,900 |
Airbnb cash on cash: 0.35%
|
255 Howells RdMiddletown, NYEnter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom,... |
5 beds | 4 baths | 4,200 sq.ft. |
$979,880 |
Airbnb cash on cash: N/A
|
708 Kirbytown RoadMiddletown, NYSuch a peaceful setting for this immaculate 4 BR, 2.5 bath Colonial in the heart of The Mi... |
4 beds | 3 baths | 2,292 sq.ft. |
$575,000 |
Airbnb cash on cash: 0.35%
|
744 Mt Hope RoadMiddletown, NYA beautiful colonial home sitting on 3 acres with open layout is being built in the town o... |
4 beds | 3 baths | 2,444 sq.ft. |
$649,900 |
Airbnb cash on cash: 0.02%
|
5 Mills AveMiddletown, NYLOCATION, LOCATION, LOCATION! Don't miss this charming 3 Bedroom, 1.5 Bathroom Two-Story H... |
3 beds | 1 baths | 1,160 sq.ft. |
$339,999 |
Airbnb cash on cash: 0.38%
|
100 Academy AvenueMiddletown, NYWELCOME HOME!!! A lovely and spacious single family property, with an extra large backyard... |
4 beds | 2 baths | 1,634 sq.ft. |
$385,000 |
Airbnb cash on cash: 1.82%
|
5 Magar StMiddletown, NYHuge Price Reduction! Welcome Home! This beautifully maintained Split -Level residence off... |
3 beds | 3 baths | 1,645 sq.ft. |
$515,000 |
Airbnb cash on cash: -1%
|
458 County Route 50Middletown, NYWelcome to 458 County Route 50! Discover the perfect blend of elegance and functionality i... |
4 beds | 3 baths | 2,200 sq.ft. |
$599,900 |
Airbnb cash on cash: -0.05%
|
15 Lindentree LnMiddletown, NYAlmost new Townhome in Maples Field is waiting for you! Welcome to our Spacious 3 bedroom,... |
3 beds | 2 baths | 1,827 sq.ft. |
$489,900 |
Airbnb cash on cash: -0.71%
|
326 Concord LnMiddletown, NYButtonwood Hills Condominiums now offers a 2 bedroom/2 bath unit for your purchase & to ca... |
2 beds | 2 baths | 924 sq.ft. |
$215,000 |
Airbnb cash on cash: 2.47%
|
21 N Aspen RdMiddletown, NYMove-in ready 3-bedroom, 2-bath townhouse in the Middletown School District. Home features... |
3 beds | 1 baths | 1,528 sq.ft. |
$304,999 |
Airbnb cash on cash: 0.43%
|
6 Eaton CtMiddletown, NYWelcome to 6?Eaton Court, a bright and comfortable 3-bed, 1.5-bath townhouse nestled in a ... |
3 beds | 1 baths | 1,248 sq.ft. |
$299,999 |
Airbnb cash on cash: 0.49%
|
13 Forest AveMiddletown, NYWelcome to 13 Forest Ave, a spacious and versatile home located in the heart of Middletown... |
3 beds | 2 baths | 1,748 sq.ft. |
$429,999 |
Airbnb cash on cash: -0.19%
|
17 Woodrose CtMiddletown, NYDiscover the perfect blend of classic charm and modern comfort in this beautiful Colonial-... |
3 beds | 2 baths | 2,763 sq.ft. |
$515,000 |
Airbnb cash on cash: -0.73%
|
238 S Centerville RdMiddletown, NYSpacious Country Retreat on 22.6 Acres in Minisink Valley School District This exceptional... |
5 beds | 2 baths | 3,764 sq.ft. |
$849,000 |
Airbnb cash on cash: N/A
|
104 North StreetMiddletown, NYCompletely updated 8-apartment, 3-retail-unit mixed-use building located next to the bus t... |
N/A beds | N/A baths | N/A |
$2,550,000 |
Airbnb cash on cash: -1.84%
|
39 W Main StreetMiddletown, NYDiscover endless potential in this mixed-use standalone building, ideally located in the h... |
N/A beds | N/A baths | N/A |
$1,360,000 |
Airbnb cash on cash: -1.68%
|
1 Weather Vane WayMiddletown, NYWelcome to the one that finally checks all the boxes at 1 Weather Vane Way, Middletown, NY... |
4 beds | 2 baths | 1,955 sq.ft. |
$499,000 |
Airbnb cash on cash: 1.25%
|
1065 Dolsontown RdMiddletown, NYWelcome to this private and spacious raised ranch located in the Town of Wawayanda within ... |
3 beds | 2 baths | 1,184 sq.ft. |
$425,000 |
Airbnb cash on cash: -0.1%
|
6 Deer Ct DriveMiddletown, NYBright and well-maintained 2-bedroom, 2.5-bath unit located in the desirable Deer Run comm... |
2 beds | 3 baths | 1,831 sq.ft. |
$325,000 |
Airbnb cash on cash: 0.43%
|
Real Estate investment in Middletown, NY
There are 168 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 $208. In March 2026, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $3,038.