Middletown, IN Homes

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  /66

  $2 Pending

  • 3 Beds
  • 1 Bath
  • 1,199 Sq Ft

  5708 N County Road 700 W, Middletown, IN 47356

  To be sold in an Online Only Auction on Tuesday, October 14th @ 5 PM EST. This auction brings to you a beautiful property on just over 1 acre in Middletown, IN being sold ABSOLUTE No-Reserve! Come check out this ranch home that has been well taken care of. 3 bedrooms, 1 bathroom, and 1,199 sqft of space to make your own. The main level offers a living area with a cozy gas fireplace, convenient

  

  Caleb Cleek

  Jeff Boone Realty, LLC

  (855) 768-4708

  5708 N County Road 700 W, Middletown, IN 47356
• 

  

  

  /20

  $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
• 

  

  

  /41

  $325,000 Sold Oct 24, 2025

  • 2,352 Sq Ft
  • $138/SF
  • 45 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1975

  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

  4573 E State Road 236, Middletown, IN 47356
• 

  

  

  /29

  Est $645,485 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
• 

  

  

  /35

  $2 Pending

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  5080 S County Road 450 E, Middletown, IN 47356

  To be sold in an Online Only Auction on Sunday, October 12th @ 3 PM EST. Don't miss this 1 acre property in Middletown, IN being sold at auction! A 1,392 sqft brick ranch home in Pendleton School Systems with a rural setting! This home offers an eat-in kitchen with dishwasher, spacious living areas with vaulted ceilings, and a non-working fireplace that adds charm. Enjoy a fully fenced backyard,

  

  Caleb Cleek

  Jeff Boone Realty, LLC

  (866) 619-3723

  5080 S County Road 450 E, Middletown, IN 47356
• 

  

  /25

  $1,249 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 76, Middletown, IN 47356

  ENJOY SPOOKTACULAR SAVINGS! 2 MONTHS FREE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! ACT FAST! *Restrictions Apply. Welcome to your next home in the beautiful Crestwood community of Middletown, Indiana. This spacious home blends modern convenience with cozy charm. Step into a bright, open-concept living area featuring a built-in entertainment center, perfect for movie nights or hosting

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 76, Middletown, IN 47356
• 

  

  /24

  $163,000 Sold Oct 14, 2025

  • 1,002 Sq Ft
  • $163/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  553 Liberty St, Middletown, IN 47356

  Small town living. This nicely updated two bedroom one bath home is ready for you. Kitchen includes all stainless steel appliances and the center island. Both bedrooms are very nice sized with large closets. Main bathroom has been completely updated! Large lot with a back gravel driveway leading to the oversize two car garage! Front gravel driveway has plenty of room for guest parking.

  Rachel Ellis RE/MAX Real Estate Solutions

  553 Liberty St, Middletown, IN 47356
• 

  

  /16

  Est $180,881 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
• 

  

  /10

  $135,000

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  1458 Congress St, Middletown, IN 47356

  Welcome home to this cozy and inviting bungalow, perfectly blending charm and comfort in every detail. Featuring 2 bedrooms, a bright and functional kitchen, and a detached 1-car garage, this home is ideal for first-time buyers, downsizers, or anyone seeking an easy-to-maintain space in a convenient location. Step inside to find a warm, welcoming living area filled with natural light and a

  Phillip Whitaker Asher Real Estate Agency

  1458 Congress St, Middletown, IN 47356
• 

  

  /38

  $1,244 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 70, Middletown, IN 47356

  ENJOY SPOOKTACULAR SAVINGS IN OCTOBER! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! ACT FAST! *Restrictions Apply. Welcome to this thoughtfully upgraded 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
• 

  

  /21

  $215,000 Sold Oct 10, 2025

  • 1,502 Sq Ft
  • $143/SF
  • 26 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1941

  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

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

  

  /5

  Est $94,263 Not Listed For Sale

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

  1459 Congress St, Middletown, IN 47356

  1459 Congress St, Middletown, IN 47356
• 

  

  /19

  $239,900

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  7137 N County Road 600 W, Middletown, IN 47356

  Nestled at 7137 N County Road 600 W, MIDDLETOWN, IN, this single-family residence in Henry County presents an attractive property in great condition. Imagine crafting culinary masterpieces in the kitchen, complete with a stylish kitchen bar and a kitchen peninsula, both adorned with shaker cabinets and elegant countertops. The property features a fenced backyard, offering a private outdoor space.

  Marty Dulworth RE/MAX Real Estate Solutions

  7137 N County Road 600 W, Middletown, IN 47356
• 

  

  /9

  $1,244 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 116, Middletown, IN 47356

  ENJOY SPOOKTACULAR SAVINGS! 2 MONTHS FREE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 116, Middletown, IN 47356
• 

  

  /21

  $254,900 Sold Oct 08, 2025

  • 1,464 Sq Ft
  • $174/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  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
• 

  

  /59

  Est $308,336 Not Listed For Sale

  • 4 Beds
  • 1,152 Sq Ft

  818 Cossack Dr, Middletown, IN 47356

  818 Cossack Dr, Middletown, IN 47356
• 

  

  /41

  $395,000

  • 5 Beds
  • 1.5 Baths
  • 3,782 Sq Ft

  6912 N County Road 700 W, Middletown, IN 47356

  Welcome to country living at its best! This spacious farmhouse sits on 2.4 beautiful acres and offers plenty of room both inside and out. Step inside to a large great room perfect for family gatherings, a generous kitchen and dining area, and five total bedrooms providing space for everyone. Enjoy peaceful mornings on the covered front porch, and appreciate the convenience of a two-car attached

  Marty Dulworth RE/MAX Real Estate Solutions

  6912 N County Road 700 W, Middletown, IN 47356
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  /36

  $1,249 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 97, Middletown, IN 47356

  ENJOY SPOOKTACULAR SAVINGS! 2 MONTHS FREE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! 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
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  /44

  $159,000 Sold Sep 24, 2025

  • 2,568 Sq Ft
  • $62/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  168 N 7th St, Middletown, IN 47356

  Inviting 3-bed, 2-bath home with over 2,500 sq ft of living space in the heart of downtown Middletown. This spacious and character-filled home has so much to offer. From the enclosed front porch and original solid wood entry doors to the beautiful original hardwood floors, you'll find charm and craftsmanship throughout. The main floor features a large living area that flows into a cozy sitting

  Schuyler Estes RE/MAX Real Estate Solutions

  168 N 7th St, Middletown, IN 47356
• 

  

  /30

  Est $196,841 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 2,127 Sq Ft

  2483 W County Road 400 N, Middletown, IN 47356

  2483 W County Road 400 N, Middletown, IN 47356
• 

  

  /28

  $200,000

  • 3 Beds
  • 1 Bath
  • 1,025 Sq Ft

  8525 W State Road 236, Middletown, IN 47356

  Welcome home to this charming brick ranch on nearly three-quarters of an acre in the highly sought-after Shenandoah School District! This well-kept property offers the perfect mix of comfort and convenience with a fully fenced backyard, enclosed patio for year-round enjoyment, and plenty of extra storage with a 2-car attached garage and backyard shed. Inside, you'll love the timeless hardwood

  Adam Hartley RE/MAX Edge

  8525 W State Road 236, Middletown, IN 47356
• 

  

  /27

  $1,299 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 4, Middletown, IN 47356

  ENJOY SPOOKTACULAR SAVINGS IN OCTOBER! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 4, Middletown, IN 47356
• 

  

  /13

  $168,900 Sold Sep 23, 2025

  • 1,405 Sq Ft
  • $120/SF
  • 27 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2001

  512 N 5th St, Middletown, IN 47356

  Located at 512 N 5th ST, MIDDLETOWN, IN, this single-family residence in the heart of Indiana offers a unique opportunity to embrace comfortable living. The residence features two bedrooms, offering ample space for relaxation and personalization. The configuration includes a full handicap tiled walk in Shower that can be used by all. bathroom, designed for both efficiency and comfort, as well

  Sharon Baker Carpenter, REALTORS®

  512 N 5th St, Middletown, IN 47356
• 

  

  /46

  Est $357,160 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
• 

  

  /15

  $279,900

  • 4 Beds
  • 1.5 Baths
  • 2,205 Sq Ft

  579 N 5th St, Middletown, IN 47356

  579 N 5th Street offers four bedrooms with two full custom bathrooms - thoughtfully designed for both style and functionality. Situated on a corner lot, the property includes an oversized 2.5 car garage, two-story detached garage. Recent updates include a new roof, new AC unit, and all new appliances within the last 5 years - offering peace of mind and move-in-ready comfort. The home has been

  Danielle Bryant RE/MAX Integrity Real Estate

  579 N 5th St, Middletown, IN 47356
• 

  

  /13

  $1,214 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 21, Middletown, IN 47356

  ENJOY SPOOKTACULAR SAVINGS! 2 MONTHS FREE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 21, Middletown, IN 47356
• 

  

  /58

  $407,000 Sold Sep 22, 2025

  • 2,190 Sq Ft
  • $186/SF
  • 1 Day On Market

  • 4 Beds
  • 3 Baths
  • Built 1993

  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
• 

  

  /43

  Est $281,621 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
• 

  

  /32

  $259,900

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  5636 N Mechanicsburg Rd, Middletown, IN 47356

  Get your own slice of country living on this 1.2-acre lot with mature trees, beautiful views, and all the privacy you could want. Start your mornings with coffee on the deck while watching deer and other wildlife right in your backyard. The large kitchen offers plenty of space, the cozy wood burning fireplace warms the spacious living room, and the basement provides endless possibilities. It

  Kimberly Goodwin RE/MAX At The Crossing

  5636 N Mechanicsburg Rd, Middletown, IN 47356
• 

  

  /9

  $1,244 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 114, Middletown, IN 47356

  ENJOY SPOOKTACULAR SAVINGS IN OCTOBER! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 114, 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
• 

  

  /6

  Est $206,222 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
• 

  

  /24

  $240,000

  • 4 Beds
  • 1 Bath
  • 1,608 Sq Ft

  503 N 10th St, Middletown, IN 47356

  Welcome to this beautifully updated 4-bedroom, 1-bathroom ranch home nestled in the highly sought-after Shenandoah School Corporation. With tasteful updates throughout, this home offers a perfect blend of modern comfort and classic charm. As you step inside, you'll immediately notice the spacious and inviting family room, offering plenty of room for relaxation and entertainment. The large

  Megan Silva RE/MAX Real Estate Solutions

  503 N 10th St, Middletown, IN 47356
• 

  

  /36

  $1,249 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 69, Middletown, IN 47356

  ENJOY SPOOKTACULAR SAVINGS! 2 MONTHS FREE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 69, 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
• 

  

  /54

  Est $440,553 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,799 Sq Ft

  2801 W County Road 650 N, Middletown, IN 47356

  2801 W County Road 650 N, Middletown, IN 47356
• 

  

  /56

  $289,900

  • 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
• 

  

  /38

  $1,220 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 66, Middletown, IN 47356

  ENJOY SPOOKTACULAR SAVINGS! 2 MONTHS FREE RENT & NO APPLICATION FEES*! EXPIRES 10/31/25! 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 66, 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
• 

  

  /12

  Est $222,911 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft

  3701 N County Road 575 W, Middletown, IN 47356

  3701 N County Road 575 W, Middletown, IN 47356

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