Real Estate Investment Properties for Sale in Middletown, IN
Looking for investment property in Middletown, IN with high ROI ?
Explore a variety of short-term homes & houses in Middletown, IN. Invest wisely with VRBO & Middletown, IN 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, IN
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
9161 N Raider RoadMiddletown, INCharming Homestead on nearly 4 acres-Ultimate Mini-Farm and country Living! The spacious i... |
4 beds | 2 baths | 2,392 sq.ft. |
$379,000 |
Airbnb cash on cash: N/A
|
118 N 8th StMiddletown, INThis adorable home is located in-town Middletown. Cozy cottage feel includes shiplap, lar... |
2 beds | 1 baths | 1,503 sq.ft. |
$125,000 |
Airbnb cash on cash: N/A
|
558 Central AveMiddletown, INMove in ready 2 bed/ 1 bath home in a quiet neighborhood. Upstairs has a separate office/ ... |
2 beds | 1 baths | 1,521 sq.ft. |
$209,900 |
Airbnb cash on cash: N/A
|
5579 W US Highway 36Middletown, INStep back in time with this turn-of-the-century country farmhouse situated on 11.24 acres ... |
3 beds | 1 baths | 1,932 sq.ft. |
$335,000 |
Airbnb cash on cash: N/A
|
4998 N County Road 575 WMiddletown, IN4998 N County Road 575 W, Middletown, IN 47356 | Other |
N/A beds | N/A baths | N/A |
$570,000 |
Airbnb cash on cash: N/A
|
8271 W County Road 700 NMiddletown, INIf privacy is what you're looking for, this exceptional property delivers. Set approximate... |
4 beds | 2 baths | 3,072 sq.ft. |
$435,000 |
Airbnb cash on cash: N/A
|
9161 N Raider RdMiddletown, IN9161 N Raider Rd, Middletown, IN 47356 | Single Family Residential |
4 beds | 2 baths | 2,392 sq.ft. |
$362,000 |
Airbnb cash on cash: N/A
|
4879 S County Road 350 EMiddletown, IN4879 S County Road 350 E, Middletown, IN 47356 | Single Family Residential |
4 beds | 2 baths | 3,401 sq.ft. |
$599,900 |
Airbnb cash on cash: N/A
|
3977 N County Road 575 WMiddletown, IN3977 N County Road 575 W, Middletown, IN 47356 | Single Family Residential |
3 beds | 1 baths | 1,296 sq.ft. |
$249,900 |
Airbnb cash on cash: N/A
|
1253 Congress StMiddletown, IN1253 Congress St, Middletown, IN 47356 | Single Family Residential |
3 beds | 1 baths | 1,458 sq.ft. |
$114,900 |
Airbnb cash on cash: N/A
|
1257 Congress StMiddletown, IN1257 Congress St, Middletown, IN 47356 | Single Family Residential |
3 beds | 2 baths | 1,820 sq.ft. |
$164,900 |
Airbnb cash on cash: N/A
|
512 N 5th StMiddletown, IN512 N 5th St, Middletown, IN 47356 | Single Family Residential |
2 beds | 1 baths | 1,405 sq.ft. |
$170,000 |
Airbnb cash on cash: N/A
|
1318 Cottage AveMiddletown, IN1318 Cottage Ave, Middletown, IN 47356 | Single Family Residential |
3 beds | 1 baths | 980 sq.ft. |
$134,900 |
Airbnb cash on cash: N/A
|
814 Earl AveMiddletown, IN814 Earl Ave, Middletown, IN 47356 | Single Family Residential |
3 beds | 1 baths | 1,168 sq.ft. |
$254,900 |
Airbnb cash on cash: N/A
|
8262 N Mechanicsburg RdMiddletown, IN8262 N Mechanicsburg Rd, Middletown, IN 47356 | Single Family Residential |
4 beds | 2 baths | 2,212 sq.ft. |
$375,000 |
Airbnb cash on cash: N/A
|
4681 E State Road 236Middletown, IN
|
2 beds | 1 baths | 1,269 sq.ft. |
$74,900 |
Airbnb cash on cash: N/A
|
890 Columbia AveMiddletown, IN890 Columbia Ave, Middletown, IN 47356 | Single Family Residential |
2 beds | 1 baths | 1,000 sq.ft. |
$134,900 |
Airbnb cash on cash: N/A
|
503 N 10th StreetMiddletown, INWelcome to this beautifully updated 4-bedroom, 1-bathroom ranch home nestled in the highly... |
4 beds | 1 baths | 1,608 sq.ft. |
$240,000 |
Airbnb cash on cash: N/A
|
687 W Mill StreetMiddletown, INDiscover the charm of 687 W Mill ST, MIDDLETOWN, IN. This single-family residence, situate... |
2 beds | 1 baths | 1,268 sq.ft. |
$135,000 |
Airbnb cash on cash: N/A
|
4326 E County Road 500 SMiddletown, INCompletely updated and move-in ready, this 3-bedroom, 2-bath home offers 2,132 finished sq... |
3 beds | 2 baths | 2,132 sq.ft. |
$279,900 |
Airbnb cash on cash: N/A
|
900 Maple StreetMiddletown, INWelcome to 900 Maple ST in MIDDLETOWN, IN, a charming single-family residence built in 196... |
3 beds | 2 baths | 1,554 sq.ft. |
$249,900 |
Airbnb cash on cash: N/A
|
6803 N County Road 700 WMiddletown, INSituated on 1.75 acres, this tri-level home offers space, functionality, and peaceful coun... |
2 beds | 1 baths | 1,584 sq.ft. |
$246,000 |
Airbnb cash on cash: N/A
|
1396 Congress StreetMiddletown, INWelcome home to this inviting 3-bedroom, 1-bath property situated on a spacious corner lot... |
3 beds | 1 baths | 1,334 sq.ft. |
$160,000 |
Airbnb cash on cash: N/A
|
269 N 8th StMiddletown, INA welcoming single-family residence built in 1900, offering 1384 square feet. This invitin... |
3 beds | 1 baths | 2,404 sq.ft. |
$164,900 |
Airbnb cash on cash: N/A
|
7121 W County Road 700Middletown, IN
|
3 beds | 2 baths | 1,512 sq.ft. |
$184,900 |
Airbnb cash on cash: N/A
|
850 Progress StreetMiddletown, INDiscover the inviting charm of 850 Progress ST in MIDDLETOWN, IN, a single-family residenc... |
3 beds | 2 baths | 1,040 sq.ft. |
$169,900 |
Airbnb cash on cash: N/A
|
Real Estate investment in Middletown, IN
There are 26 properties for sale in the city of Middletown . The median list price in Middletown is $168,349 and the average price per square foot is $103. In October 2026, the average monthly cash on cash return in Middletown is 9.00%. The average monthly rental income in Middletown is $1,479.