Middletown, IN Homes

• 

  

  

  /21

  $215,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,502 Sq Ft

  11801 S County Road 600 W, Middletown, IN 47356

  Super cute 2 bedroom 2 bath home on 2 acres in Daleville schools! You will love the open fill with large living spaces opening to the kitchen. New paint and flooring throughout.

  

  Lisa Buckner

  RE/MAX Real Estate Groups

  (833) 329-0571

  11801 S County Road 600 W, Middletown, IN 47356
• 

  

  

  /19

  $1,149 - $1,349 per month

  Crestwood MHC

  2 - 3 Beds

  27 Crestwood Dr, Middletown, IN 47356

  Welcome to Crestwood! An all-age, pet-friendly manufactured home community located in Middletown, Indiana. Here, you’ll find the ideal mix of small-town charm and everyday convenience, with a community feel that’s perfect for individuals and families alike.Nestled in a quiet area just minutes from local shopping and dining, Crestwood offers the comfort of community living with easy access

  27 Crestwood Dr, Middletown, IN 47356
• 

  

  

  /31

  $262,200 Sold Sep 10, 2025

  • 1,372 Sq Ft
  • $191/SF
  • 54 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1975

  5411 N County Road 850 W, Middletown, IN 47356

  Welcome to your peaceful retreat in the heart of the countryside! This inviting 3-bedroom, 1-1/2 bath, this two-story home sits on a spacious 1-acre lot, offering the perfect blend of comfort and rural charm. Inside, you'll find a warm, functional layout with plenty of natural light and space to make your own. Step outside to enjoy a spacious yard, ideal for gardening, relaxing, or

  Marty Dulworth RE/MAX Real Estate Solutions

  5411 N County Road 850 W, Middletown, IN 47356
• 

  

  

  /33

  Est $164,355 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 2,252 Sq Ft

  153 N 5th St, Middletown, IN 47356

  153 N 5th St, Middletown, IN 47356
• 

  

  

  /41

  $335,000

  • 4 Beds
  • 2.5 Baths
  • 2,352 Sq Ft

  4573 E State Road 236, Middletown, IN 47356

  A little piece of heaven in Middletown. Check out this sprawling ranch with an ideal layout for multi-generational living, wonderful gathering spaces in the heart of the home and back yard, and plenty of storage in the enormous 4 car garage with attached lean-to shed. The kitchen is open to the living space and close to the covered back patio. The patio is the perfect place to watch legendary

  

  Shelley Hansell

  Keller Williams Indy Metro NE

  (866) 864-3815

  4573 E State Road 236, Middletown, IN 47356
• 

  

  /9

  $1,244 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 116, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Step into comfort and style with this brand-new manufactured home designed for modern living. Featuring an open-concept layout, this home combines functionality with tasteful design elements that make it truly inviting. The bright and airy kitchen comes complete with sleek cabinetry,

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 116, Middletown, IN 47356
• 

  

  /30

  $190,000 Sold Sep 05, 2025

  • 1,352 Sq Ft
  • $141/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1994

  879 Earl Ave, Middletown, IN 47356

  This very nice 3 bedroom, 2 bath ranch home is in great condition and located on a quiet Middletown Street with a country feel! Recent improvements include new flooring, a new patio door, and a newer storm door. The lot is 1/2 acre with a chain link fenced area in the back with plenty more property to enjoy! It's a great private setting with a hay field located to the North of the home. Don't

  Jeff Weightman Weightman Realty Group, LLC

  879 Earl Ave, Middletown, IN 47356
• 

  

  /43

  Est $311,244 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,805 Sq Ft

  5076 S County Road 450 E, Middletown, IN 47356

  5076 S County Road 450 E, Middletown, IN 47356
• 

  

  /21

  $254,900

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft

  511 N 12th St, Middletown, IN 47356

  Discover an inviting home awaiting at 511 N 12th ST, MIDDLETOWN, IN. This ready-to-move-in residence in popular HONNOLDS Addition. Shenandoah School Systems. Within this split level single-family residence, you will find two full bathrooms, providing convenience and privacy for all. The kitchen offers a nice eat in kitchen just off the back patio. With three bedrooms. A laundry room adds

  Doug Rector Doug Rector

  511 N 12th St, Middletown, IN 47356
• 

  

  /12

  $1,249 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 97, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Looking for your dream home at an unbeatable price? This stunning brand new 3 bedroom, 2 bathroom home offers modern living with all the extras. Features Include: Spacious Open Concept living, kitchen, and dining area - perfect for entertaining! Brand New Appliances - including

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 97, Middletown, IN 47356
• 

  

  /33

  $255,000 Sold Sep 04, 2025

  • 2,920 Sq Ft
  • $87/SF
  • 257 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1952

  914 Maple St, Middletown, IN 47356

  Welcome to this stunning one-level ranch home with almost 3000sf, two covered front porches providing welcoming entrances, beautifully situated on a .58 acre corner lot in the Shenandoah School District. Offering an expansive 4-bedroom, 2.5-bathroom layout, this property combines comfort and style with awesome living space and outdoor amenities. As you enter through the foyer, you'll be greeted

  Candy Bair RE/MAX Real Estate Solutions

  914 Maple St, Middletown, IN 47356
• 

  

  /29

  Est $623,294 Not Listed For Sale

  • 232 Beds
  • 5 Baths
  • 3,058 Sq Ft

  7263 N County Road 700 W, Middletown, IN 47356

  7263 N County Road 700 W, Middletown, IN 47356
• 

  

  /56

  $299,900

  • 2 Beds
  • 1 Bath
  • 1,512 Sq Ft

  4863 W County Road 600 N, Middletown, IN 47356

  Nestled at 4863 W County Road 600 N, MIDDLETOWN, IN, this inviting home in Henry County stands ready to welcome you. Imagine mornings spent in the kitchen, where the shaker cabinets and create a space that is both stylish and functional, perfect for preparing everything from simple breakfasts to elaborate weekend brunches. The living room, adorned with original woodwork, offers a touch of

  Marty Dulworth RE/MAX Real Estate Solutions

  4863 W County Road 600 N, Middletown, IN 47356
• 

  

  /23

  $1,249 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 76, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Charming 3 Bed, 2 Bath Home in Crestwood, Middletown IN Welcome to your next home in the beautiful Crestwood community of Middletown, Indiana. This spacious 3 bedroom, 2 bathroom home blends modern convenience with cozy charm. Step into a bright, open-concept living area featuring a

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 76, Middletown, IN 47356
• 

  

  /40

  $229,690 Sold Aug 27, 2025

  • 1,732 Sq Ft
  • $133/SF
  • 23 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  5634 N Quail Ln, Middletown, IN 47356

  To be sold in an online auction on Sunday, August 10th @ 5 PM EST. A 3 bed 2 bath 1,732 sqft house with a beautiful yard, and mature trees! Enjoy the huge porch that wraps around the front and side of the home! Convenient basement access for storage and utilities. Attached garage to park your car inside on a rainy or cold day, or possible workshop/hobby space. Come take a look!

  Caleb Cleek Jeff Boone Realty, LLC

  5634 N Quail Ln, Middletown, IN 47356
• 

  

  /16

  Est $186,287 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,318 Sq Ft

  8084 N County Road 875 W, Middletown, IN 47356

  8084 N County Road 875 W, Middletown, IN 47356
• 

  

  /54

  $484,700

  • 4 Beds
  • 4 Baths
  • 4,016 Sq Ft

  8482 N Cherry Knoll Dr, Middletown, IN 47356

  Custom all-brick home on a generous lot (.86 acres) in the Shenandoah School District. With 2,852 sq. ft. on the main & upper levels plus a finished basement, this home offers plenty of room for family, guests, and home-based work. You begin by greeting your family & guests at the front door with sidelights and a transom window for some added sunshine. Inside, the home office features 15lite

  John Rhodes III Indiana Select Realty LLC

  8482 N Cherry Knoll Dr, Middletown, IN 47356
• 

  

  /6

  $1,349 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 4, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Discover this beautiful 3 bedroom, 2 bathroom home located in the welcoming Crestwood community of Middletown, Indiana. Designed with an open floor plan, this home offers both style and functionality, making it ideal for modern living. Step inside to find durable vinyl wood flooring

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 4, Middletown, IN 47356
• 

  

  /20

  $173,000 Sold Aug 27, 2025

  • 1,286 Sq Ft
  • $135/SF
  • 16 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  663 N 5th St, Middletown, IN 47356

  This adorable 3 bedroom 1 bath home has so much to offer! The large living room is open to the kitchen/dining area. There is an updated bathroom and laundry room with extra storage on the main floor. Not only is it in the Shenandoah School District, it also offers a large back yard that is partially fenced in with a firepit. The detached garage and shed gives you the extra storage space you

  Donna Showalter Legacy Real Estate Partners

  663 N 5th St, Middletown, IN 47356
• 

  

  /5

  Est $100,305 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,248 Sq Ft

  1459 Congress St, Middletown, IN 47356

  1459 Congress St, Middletown, IN 47356
• 

  

  /39

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,875 Sq Ft

  5571 N Raider Rd, Middletown, IN 47356

  Beautiful ranch home offering 3 bedrooms, 1 bathroom, laundry room and attached garage. This property sits on over 4 acres of land with a barn suitable for animals and a lean to, 2.5 acres are fenced. The garage is fully insulated with heating and cooling. Located within miles of Shenandoah School District and less than 3 miles to the town of Middletown.

  Christina Boyland Rhodes Realty, LLC

  5571 N Raider Rd, Middletown, IN 47356
• 

  

  /39

  $1,244 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 70, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Welcome to this thoughtfully upgraded 3 bedroom, 2 bathroom home located in the heart of Crestwood. With wood vinyl flooring extending throughout the entire home, every room feels cohesive, durable, and easy to maintain. The kitchen is equipped with stainless steel appliances, a gas

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 70, Middletown, IN 47356
• 

  

  /34

  $179,900 Sold Aug 27, 2025

  • 1,153 Sq Ft
  • $156/SF
  • 59 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  482 N 7th St, Middletown, IN 47356

  Nestled in Middletown. This home offers a beautifully manicured corner lot with Wisteria Vine, Azaleas, Spireas, Lilacs, Hydrangea, Rhododendron and much more! Greenhouse with power is located on the southeast corner of parcel. The backyard is completely fenced in, connecting to the detached garage and workshop. Home has central air, three bedrooms, one bath and ample amount of storage space.

  Dawn Cravens The Taflinger Real Estate Group

  482 N 7th St, Middletown, IN 47356
• 

  /2

  Est $218,896 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,952 Sq Ft

  802 Cossack Dr, Middletown, IN 47356

  802 Cossack Dr, Middletown, IN 47356
• 

  

  /58

  $407,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,190 Sq Ft

  6755 W County Road 675 N, Middletown, IN 47356

  Charming 4-Bedroom Colonial Home with Spacious Yard in Middletown, IN Nestled in a serene, country setting, this beautifully maintained 2-story colonial home offers 4 bedrooms, 3 bathrooms, and 2,190 square feet of comfortable living space. Built in 1993, the home combines timeless elegance with modern amenities, perfect for family living. The spacious interior features a primary bedroom

  John Rhodes III Indiana Select Realty LLC

  6755 W County Road 675 N, Middletown, IN 47356
• 

  

  /13

  $1,249 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 21, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Step inside this stunning brand new manufactured home where modern design meets everyday comfort. The open-concept floor plan features a bright kitchen with a stylish peninsula that offers extra seating, brand new appliances, and plenty of cabinet space-perfect for entertaining or

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 21, Middletown, IN 47356
• 

  

  /36

  $160,000 Sold Aug 22, 2025

  • 1,404 Sq Ft
  • $114/SF
  • 2 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1937

  1144 Cottage Ave, Middletown, IN 47356

  Nestled at 1144 Cottage AVE, MIDDLETOWN, IN, this single-family residence presents an attractive property in great condition, ready to welcome you home. Imagine preparing meals in the kitchen, which features lots of cabinets and a wood ceiling, with a backsplash that adds a touch of visual interest. The outdoor areas provide a variety of options for relaxation and entertainment, including a

  Marty Dulworth RE/MAX Real Estate Solutions

  1144 Cottage Ave, Middletown, IN 47356
• 

  

  /59

  Est $307,522 Not Listed For Sale

  • 4 Beds
  • 1,152 Sq Ft

  818 Cossack Dr, Middletown, IN 47356

  818 Cossack Dr, Middletown, IN 47356
• 

  

  /36

  $335,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,392 Sq Ft

  9161 N Raider Rd, Middletown, IN 47356

  A spacious 5 bedroom, 2 bath bi-level home sits on 3.72 acres and offers a perfect blend of comfort and functionality. Inside you'll find a large living room, a versatile bonus room, and a huge kitchen/dining area with ample cabinet space ideal for gatherings and everyday living. Recent updates include a new roof, water heater, appliances, carpets, and a renovated primary bath, making this home

  Mary Cordle Berkshire Hathaway Indiana Realty

  9161 N Raider Rd, Middletown, IN 47356
• 

  

  /9

  $1,244 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 114, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Your brand new home awaits at Crestwood! This spacious 3 bedroom, 2 bathroom home offers 1,216 square feet of thoughtfully designed living space. Vinyl wood flooring flows seamlessly throughout the main living areas, creating a warm and inviting feel. The open kitchen is equipped

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 114, Middletown, IN 47356
• 

  

  /25

  $285,000 Sold Aug 21, 2025

  • 5,824 Sq Ft
  • $49/SF
  • 63 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1977

  254 N 7th St, Middletown, IN 47356

  This must see beautiful historic 3 bedroom home with a 3 car garage offers an additional 2 bedroom updated rental property or in-law quarters with split utility and private concrete drive. Inside the home there are 4 original fireplaces, a grand stairway in foyer leading upstairs to a 2 story front porch over looking the town. The upstairs has 3 large bedrooms with walk in closets and a large

  Doug Rector Doug Rector

  254 N 7th St, Middletown, IN 47356
• 

  

  /46

  Est $344,480 Not Listed For Sale

  • 5 Beds
  • 5 Baths
  • 3,754 Sq Ft

  4700 N County Road 300 W, Middletown, IN 47356

  4700 N County Road 300 W, Middletown, IN 47356
• 

  

  /10

  $45,000

  • 3 Beds
  • 1 Bath
  • 840 Sq Ft

  1403 Congress St, Middletown, IN 47356

  Attention investors, rehabbers, and visionaries! This 3-bed, 1-bath home sits on a generous lot with a covered carport and fenced yard. Located in a quiet neighborhood, the property offers a solid foundation and strong bones-ready for your next fix-and-flip or long-term rental. While the home has experienced fire damage, it presents a unique opportunity to rebuild equity quickly. Much of the

  Zachary Erby Hashtag Real Estate

  1403 Congress St, Middletown, IN 47356
• 

  

  /41

  $1,249 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 69, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Welcome to this thoughtfully upgraded 3 bedroom, 2 bathroom home located in the heart of Crestwood. With wood vinyl flooring extending throughout the entire home, every room feels cohesive, durable, and easy to maintain. The kitchen is equipped with stainless steel appliances, a gas

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 69, Middletown, IN 47356
• 

  

  /35

  $165,000 Sold Aug 20, 2025

  • 1,192 Sq Ft
  • $138/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1900

  127 N 8th St, Middletown, IN 47356

  Welcome to 127 N 8th Street in the heart of Middletown. This beautifully updated 2-bedroom home with a loft and basement offers the perfect blend of charm and modern convenience. Nearly every inch of this home has been thoughtfully remodeled including all-new electrical, plumbing, flooring, and lighting throughout. The kitchen features new cabinets, fixtures, and appliances, while the full

  Robyn Breece @properties

  127 N 8th St, Middletown, IN 47356
• 

  

  /43

  Est $277,684 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,749 Sq Ft

  5431 N County Road 200 W, Middletown, IN 47356

  5431 N County Road 200 W, Middletown, IN 47356
• 

  

  /5

  $199,000

  • Land
  • 17.59 Acres
  • $11,313 per Acre

  **** N County Road 400 W, Middletown, IN 47356

  17+ acres. Currently being used as tillable farm ground but could be a beautiful building lot. Great road frontage in a rural setting.

  Perri Trennepohl Keller Williams Realty

  **** N County Road 400 W, Middletown, IN 47356
• 

  

  /38

  $1,220 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 66, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Welcome to Your Dream Home in Crestwood! Step into comfort and style in this beautifully designed 3 bedroom 2 bathroom home located in the desirable Crestwood community. Featuring a spacious open floor plan, this home is perfect for both everyday living and entertaining. The heart of

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 66, Middletown, IN 47356
• 

  

  /22

  $208,000 Sold Aug 11, 2025

  • 1,765 Sq Ft
  • $118/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  975 Locust St, Middletown, IN 47356

  Completely Renovated & Move In Ready! Welcome to 975 Locust Street-a beautifully updated 3 bedroom, 2 bath home situated on a spacious lot in the heart of Middletown. Inside, you'll find fresh paint and new flooring throughout, along with tastefully updated bathrooms and a kitchen that shines with granite countertops. The main level primary suite offers comfort and privacy, while the cozy sunroom

  Julie Schnepp RE/MAX Legacy

  975 Locust St, Middletown, IN 47356
• 

  

  /6

  Est $216,981 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,788 Sq Ft

  2121 W County Road 575 N, Middletown, IN 47356

  2121 W County Road 575 N, Middletown, IN 47356

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