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 |
|---|---|---|---|
30 East AvenueMiddletown, NYCALLING ALL INVESTORS! Turn of the century charmer located right in the heart of Middletow... |
5 beds | 2 baths | 1,941 sq.ft. |
$280,000 |
Airbnb cash on cash: 6.57%
|
38 Woodside Knolls DriveMiddletown, NYWelcome to Woodside Knolls! Discover this stunning tri-level townhouse located in one of t... |
3 beds | 4 baths | 1,899 sq.ft. |
$479,000 |
Airbnb cash on cash: 0.04%
|
295 Lybolt RoadMiddletown, NYSpacious home with large yard on a quiet street - what more could you want? This beautiful... |
3 beds | 2 baths | 1,222 sq.ft. |
$470,000 |
Airbnb cash on cash: 0.67%
|
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: 0.48%
|
482 Scotchtown AvenueMiddletown, NYMint condition, classic, fully-restored 1863 farmhouse. This 4-bedroom, 2 1/2-bathroom hom... |
4 beds | 3 baths | 2,828 sq.ft. |
$829,000 |
Airbnb cash on cash: 0.43%
|
12 Briarwood DriveMiddletown, NYThis well-maintained home is located in a peaceful neighborhood with a pleasant environmen... |
3 beds | 3 baths | 2,184 sq.ft. |
$450,000 |
Airbnb cash on cash: 0.52%
|
936 Tower Ridge CircleMiddletown, NYLooking for resort lifestyle living, Welcome to Tower Ridge Grande. Lovely Evergreen model... |
2 beds | 2 baths | 1,216 sq.ft. |
$314,900 |
Airbnb cash on cash: -0.14%
|
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: 1.54%
|
568 County Route 49 #2CMiddletown, NYLooking for a solid investment in the Minisink Valley School District? This newer townhous... |
3 beds | 3 baths | 1,593 sq.ft. |
$379,000 |
Airbnb cash on cash: 0.17%
|
224 Concord LaneMiddletown, NYDiscover this 2-bedroom, 2-bathroom second-floor unit in Middletown, NY! Flooded with abun... |
2 beds | 2 baths | 924 sq.ft. |
$199,900 |
Airbnb cash on cash: -0.55%
|
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. |
$418,999 |
Airbnb cash on cash: 0.87%
|
167 Rockwell AvenueMiddletown, NYCharming Single-Family Home for Sale Welcome to this beautifully designed, spacious single... |
4 beds | 3 baths | 2,040 sq.ft. |
$415,000 |
Airbnb cash on cash: 3.2%
|
44 Houston AvenueMiddletown, NYExcellent opportunity to own a 2 family house whether you are an investor or want to live ... |
5 beds | 2 baths | 2,440 sq.ft. |
$369,900 |
Airbnb cash on cash: 3.55%
|
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: -0.43%
|
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: -0.4%
|
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: 0.73%
|
354 Concord LaneMiddletown, NYWelcome to 354 Concord Lane! Renovated 2 bedroom 2 full bath condo in Buttonwood Hills wit... |
2 beds | 2 baths | 924 sq.ft. |
$205,000 |
Airbnb cash on cash: -0.81%
|
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. |
$375,000 |
Airbnb cash on cash: 3.47%
|
90 Inwood RoadMiddletown, NYWelcome to this fully renovated townhouse in Inwood Hills Condominiums. This Home is a fir... |
2 beds | 1 baths | 940 sq.ft. |
$199,000 |
Airbnb cash on cash: 1.03%
|
411 Fair Oaks RoadMiddletown, NYWelcome Home! Solid Raised Ranch located in the Town of Wallkill/Pine Bush School District... |
3 beds | 3 baths | 2,496 sq.ft. |
$429,900 |
Airbnb cash on cash: 1.1%
|
34 Jimal DriveMiddletown, NYBeautifully cared and maintained 2 bedrooms, 1.5 bathrooms townhouhse in the desirable Hig... |
2 beds | 2 baths | 1,082 sq.ft. |
$259,900 |
Airbnb cash on cash: -0.37%
|
184 Highland AvenueMiddletown, NYHere you have a beautiful Victorian style home, centrally located in Middletown NY. This h... |
4 beds | 2 baths | 1,486 sq.ft. |
$355,000 |
Airbnb cash on cash: 3.63%
|
5 Cornwall LaneMiddletown, NYWelcome to this ending unit townhouse nestled in the community of Woodside Knolls. This be... |
3 beds | 3 baths | 2,491 sq.ft. |
$489,000 |
Airbnb cash on cash: 0%
|
2 Rivervale RoadMiddletown, NYCharming Corner Townhouse in Middletown â No HOA Fees! Welcome to 2 Riverdale Road, a de... |
3 beds | 2 baths | 1,484 sq.ft. |
$350,000 |
Airbnb cash on cash: 1.92%
|
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: 2.78%
|
15 Rowan Street #13Middletown, NYDiscover the perfect blend of comfort and charm in this beautifully updated home, nestled ... |
5 beds | 2 baths | 1,920 sq.ft. |
$415,789 |
Airbnb cash on cash: 3.84%
|
24 Crescent PlaceMiddletown, NYAttention all investors and home buyers! Look no further, This amazing colonial is in grea... |
3 beds | 1 baths | 1,196 sq.ft. |
$325,000 |
Airbnb cash on cash: 2.33%
|
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. |
$579,000 |
Airbnb cash on cash: 0.04%
|
324 Concord LaneMiddletown, NYWelcome to this beautiful condo in the Buttonwood Hills complex! This bright and spacious ... |
1 beds | 1 baths | 735 sq.ft. |
$169,000 |
Airbnb cash on cash: -1.32%
|
14 Laddie RoadMiddletown, NY**Charming Renovated Split-Level Home in Pine Bush School District!** Welcome to your dre... |
3 beds | 2 baths | 1,702 sq.ft. |
$439,900 |
Airbnb cash on cash: 1.15%
|
17 Sterling StreetMiddletown, NYTurnkey Two-Family Investment Opportunity. Fully renovated from the studs up just two year... |
6 beds | 2 baths | 1,400 sq.ft. |
$459,999 |
Airbnb cash on cash: 1.08%
|
147 Ruth CourtMiddletown, NYWelcome to this beautifully maintained 2-bedroom, 2-bathroom condo in Middletown! Featurin... |
2 beds | 3 baths | 880 sq.ft. |
$269,900 |
Airbnb cash on cash: 0.96%
|
200 Mt Orange RoadMiddletown, NYWelcome to this most charming 1870's farmhouse situated on idyllic 6.4 level pastoral acr... |
4 beds | 4 baths | 3,432 sq.ft. |
$699,000 |
Airbnb cash on cash: 0.49%
|
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: 3.95%
|
49 Ruth CourtMiddletown, NYSmart Buy â Ideal for Investors or Future Homeowners! This well-maintained 2-bedroom, 1-... |
2 beds | 1 baths | 1,006 sq.ft. |
$207,000 |
Airbnb cash on cash: 1.74%
|
40 Camp Orange RoadMiddletown, NYThis versatile and lucrative investment or user property sits on one of the largest open l... |
5 beds | 2 baths | 2,092 sq.ft. |
$2,995,000 |
Airbnb cash on cash: -1.36%
|
104 Elise DriveMiddletown, NYLAST HOME AVAILABLE! Welcome to The Woodlands at Scotchtown Estates! This exquisite pictur... |
5 beds | 4 baths | 3,700 sq.ft. |
$825,000 |
Airbnb cash on cash: 0.31%
|
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. |
$405,000 |
Airbnb cash on cash: 1.05%
|
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. |
$779,900 |
Airbnb cash on cash: 0.32%
|
7 Avoncroft LaneMiddletown, NYDiscover the perfect balance of modern design and everyday comfort in this beautifully upd... |
3 beds | 3 baths | 2,567 sq.ft. |
$499,999 |
Airbnb cash on cash: 0.1%
|
Real Estate investment in Middletown, NY
There are 135 properties for sale in the city of Middletown . The median list price in Middletown is $405,000 and the average price per square foot is $221. In September 2025, the average monthly cash on cash return in Middletown is 5.00%. The average monthly rental income in Middletown is $3,103.