Middletown, IN Homes

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  $140,000

  • 2 Beds
  • 1 Bath
  • 1,268 Sq Ft

  687 W Mill St, Middletown, IN 47356

  Discover the charm of 687 W Mill ST, MIDDLETOWN, IN. This single-family residence, situated in the heart of the USA, presents an exciting opportunity to reimagine a piece of history. With 1268 square feet of living area, the residence offers a comfortable layout that includes two bedrooms. The generous 11108 square foot lot provides ample space for outdoor activities. Imagine creating your own

  Marty Dulworth RE/MAX Real Estate Solutions

  687 W Mill St, Middletown, IN 47356
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  $1,129 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 97, Middletown, IN 47356

  FIND A NEW HOME FOR THE NEW YEAR! If you purchase this home, enjoy 4 months free site rent. If you rent this home, receive 3 months free rent. Plus, pay no application fees! Offer expires 1/31/26! Act Fast! Restrictions apply. Step into this well-appointed home designed with both style and function in mind. Located in the welcoming Crestwood community, this residence offers a smart layout with

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 97, Middletown, IN 47356
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  $180,000 Sold Jul 09, 2025

  8970 N County Road 500 W, Middletown, IN 47356

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Below List Price
  • $144/SF
  • 2 Days On Market

  Last Listing Agent Hilary Casstevens Epique Inc

  8970 N County Road 500 W, Middletown, IN 47356
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  Est $242,930 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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  $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
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  $1,149 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 68, Middletown, IN 47356

  FIND A NEW HOME FOR THE NEW YEAR! If you purchase this home, enjoy 4 months free site rent. If you rent this home, receive 3 months free rent. Plus, pay no application fees! Offer expires 1/31/26! 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,

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 68, Middletown, IN 47356
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  $255,000 Sold Sep 04, 2025

  914 Maple St, Middletown, IN 47356

  • 4 Beds
  • 2.5 Baths
  • 2,920 Sq Ft
  • Built 1952

  Last Sold Summary

  • 15% Below List Price
  • $87/SF
  • 257 Days On Market

  Current Estimated Value $268,342

  Last Listing Agent Candy Bair RE/MAX Real Estate Solutions

  914 Maple St, Middletown, IN 47356
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  Est $241,598 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,305 Sq Ft

  8542 W Us Highway 36, Middletown, IN 47356

  8542 W Us Highway 36, Middletown, IN 47356
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  /10

  $135,000 Pending

  • 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
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  $1,149 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 37, Middletown, IN 47356

  FALL INTO SAVINGS! 2 MONTHS FREE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Welcome to your new home in the beautiful Crestwood community! This inviting 3 bedroom, 2 bathroom property offers a perfect blend of comfort, space, and convenience! This home is all set on a generous lot with plenty of lush green space to enjoy. Inside, the open kitchen shines with

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 37, Middletown, IN 47356
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  $183,855 Sold Oct 30, 2025

  5708 N County Road 700 W, Middletown, IN 47356

  • 3 Beds
  • 1 Bath
  • 1,199 Sq Ft
  • Built 1959

  Last Sold Summary

  • 18,385,400% Above List Price
  • $153/SF
  • 22 Days On Market

  Last Listing Agent Caleb Cleek Jeff Boone Realty, LLC

  5708 N County Road 700 W, Middletown, IN 47356
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  Est $413,950 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,448 Sq Ft

  5109 N County Road 850 W, Middletown, IN 47356

  5109 N County Road 850 W, Middletown, IN 47356
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  $70,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,863 Sq Ft

  5313 W County Road 700 N, Middletown, IN 47356

  This home will need work, but it provides a good country living lifestyle with over 1800 Sq Ft of living space and sitting on just under a half-acre of land. There is a covered porch to enjoy the evenings and a fenced side yard. There is a wood burning fireplace to allow for that extra heat source on those cold winter days. The home is located in the Shenandoah school district and priced to allow

  Marty Dulworth RE/MAX Real Estate Solutions

  5313 W County Road 700 N, Middletown, IN 47356
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  $1,129 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 28, Middletown, IN 47356

  FIND A NEW HOME FOR THE NEW YEAR! If you purchase this home, enjoy 4 months free site rent. If you rent this home, receive 3 months free rent. Plus, pay no application fees! Offer expires 1/31/26! Act Fast! Restrictions apply. Discover this inviting home located in the welcoming community of Crestwood. Designed for both style and practicality, the home features wood vinyl flooring in the main

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 28, Middletown, IN 47356
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  $195,000 Sold Nov 05, 2025

  1213 W Mill St, Middletown, IN 47356

  • 3 Beds
  • 1 Bath
  • 1,107 Sq Ft
  • Built 1959

  Last Sold Summary

  • 3% Above List Price
  • $176/SF
  • 3 Days On Market

  Last Listing Agent Jenny Shopp Berkshire Hathaway Home

  1213 W Mill St, Middletown, IN 47356
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  Est $249,679 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,006 Sq Ft

  5098 N Mechanicsburg Rd, Middletown, IN 47356

  5098 N Mechanicsburg Rd, Middletown, IN 47356
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  $119,500

  • 3 Beds
  • 1 Bath
  • 1,880 Sq Ft

  6671 N County Road 525 W, Middletown, IN 47356

  Nestled on the outskirts of a small town, this spacious 3-bedroom, 1-bath home offers 1,880 sq ft of living space on just over half an acre. With a little vision and updating, this property has the potential to truly shine. Inside, you’ll find generous room sizes and a comfortable layout ready to be customized to your taste. Outside, enjoy the benefits of a large lot and a 2-car detached

  Bryce Conyers Starr Real Estate LLC

  6671 N County Road 525 W, Middletown, IN 47356
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  $1,134 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 103, Middletown, IN 47356

  FIND A NEW HOME FOR THE NEW YEAR! If you purchase this home, enjoy 4 months free site rent. If you rent this home, receive 3 months free rent. Plus, pay no application fees! Offer expires 1/31/26! Act Fast! Restrictions apply. Welcome to this beautifully updated 3 bedroom, 2 bathroom home nestled in the charming Crestwood community. With a warm, modern design and smart features throughout, this

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 103, Middletown, IN 47356
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  $363,000 Sold May 30, 2025

  2917 W County Road 650 N, Middletown, IN 47356

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Below List Price
  • $187/SF
  • 49 Days On Market

  Current Estimated Value $366,980

  Last Listing Agent Laura Wright PPG Real Estate LLC

  2917 W County Road 650 N, Middletown, IN 47356
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  Est $384,820 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,088 Sq Ft

  5584 N County Road 850 W, Middletown, IN 47356

  5584 N County Road 850 W, Middletown, IN 47356
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  $158,900

  • 3 Beds
  • 2 Baths
  • 1,226 Sq Ft

  1190 Cottage Ave, Middletown, IN 47356

  Nestled at 1190 Cottage AVE, MIDDLETOWN, IN, this single-family residence in a desirable part of the town offers an inviting home ready for its residents. The living room becomes a haven of warmth and character with its beautiful fireplace, ready to create cozy evenings and memorable moments. The kitchen is equipped with shaker cabinets, offering a blend of classic design and practical storage.

  Christina Boyland Rhodes Realty, LLC

  1190 Cottage Ave, Middletown, IN 47356
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  $1,129 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 24, Middletown, IN 47356

  FIND A NEW HOME FOR THE NEW YEAR! If you purchase this home, enjoy 4 months free site rent. If you rent this home, receive 3 months free rent. Plus, pay no application fees! Offer expires 1/31/26! Act Fast! Restrictions apply. Step into this well-appointed home designed with both style and function in mind. Located in the welcoming Crestwood community, this residence offers a smart layout with

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 24, Middletown, IN 47356
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  /16

  $156,500 Sold May 15, 2025

  11851 S Co Road 600 W, Middletown, IN 47356

  • 2 Beds
  • 1 Bath
  • 855 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Above List Price
  • $183/SF
  • 3 Days On Market

  Current Estimated Value $152,658

  Last Listing Agent Laura Wright PPG Real Estate LLC

  11851 S Co Road 600 W, Middletown, IN 47356
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  /60

  Est $537,508 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,070 Sq Ft

  8450 W County Road 575 N, Middletown, IN 47356

  8450 W County Road 575 N, Middletown, IN 47356
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  $24,900

  • 2 Beds
  • 1 Bath
  • 1,278 Sq Ft

  6875 N Spruce St, Middletown, IN 47356

  Fixer upper in Middletown. Lot is over 1/2 acre. Home could be converted into a 3/1. Includes detached garage and storage shed. Needs significant repairs, but priced accordingly.

  Barry Hines Realty Wealth Advisors

  6875 N Spruce St, Middletown, IN 47356
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  $1,209 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 22, Middletown, IN 47356

  FALL INTO SAVINGS! 4 MONTHS FREE SITE RENT & NO APPLICATION FEES*! EXPIRES 9/30/25! ACT FAST! *Restrictions Apply. Modern Comfort Meets Community Living in Crestwood! Welcome to this beautifully designed 3 bedroom, 2 bathroom home located in the desirable Crestwood community! With wood vinyl flooring throughout, the home offers a seamless blend of modern style, durability, and low-maintenance

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 22, Middletown, IN 47356
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  $174,000 Sold Jul 11, 2025

  809 State St, Middletown, IN 47356

  • 4 Beds
  • 2.5 Baths
  • 1,944 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $90/SF
  • 8 Days On Market

  Current Estimated Value $174,441

  Last Listing Agent Steffanie Hensley RE/MAX At The Crossing

  809 State St, Middletown, IN 47356
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  Est $507,689 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,662 Sq Ft

  8632 W County Road 550 N, Middletown, IN 47356

  8632 W County Road 550 N, Middletown, IN 47356
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  $136,000 Sold Apr 14, 2025

  9031 W Us Highway 36, Middletown, IN 47356

  • 3 Beds
  • 1 Bath
  • 1,606 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $85/SF
  • 24 Days On Market

  Current Estimated Value $151,057

  Last Listing Agent Caleb Cleek Jeff Boone Realty, LLC

  9031 W Us Highway 36, Middletown, IN 47356
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  Est $278,031 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft

  7780 W County Road 625 N, Middletown, IN 47356

  7780 W County Road 625 N, Middletown, IN 47356
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  $220,000 Sold Jan 16, 2026

  815 Maple St, Middletown, IN 47356

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $110/SF
  • 39 Days On Market

  Last Listing Agent Steffanie Hensley RE/MAX At The Crossing

  815 Maple St, Middletown, IN 47356
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  Est $244,180 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,544 Sq Ft

  5036 N Raider Rd, Middletown, IN 47356

  5036 N Raider Rd, Middletown, IN 47356
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  $165,000 Sold Aug 20, 2025

  127 N 8th St, Middletown, IN 47356

  • 2 Beds
  • 1 Bath
  • 1,192 Sq Ft
  • Built 1900

  Last Sold Summary

  • $138/SF
  • 5 Days On Market

  Current Estimated Value $165,081

  Last Listing Agent Robyn Breece @properties

  127 N 8th St, Middletown, IN 47356
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  Est $281,335 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,592 Sq Ft

  5223 N County Road 450 W, Middletown, IN 47356

  5223 N County Road 450 W, Middletown, IN 47356
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  $138,400 Sold Oct 30, 2025

  829 High St, Middletown, IN 47356

  • 3 Beds
  • 1 Bath
  • 1,074 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Below List Price
  • $129/SF
  • 6 Days On Market

  Last Listing Agent Christina Boyland Rhodes Realty, LLC

  829 High St, Middletown, IN 47356
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  /14

  Est $337,748 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,338 Sq Ft

  5937 N County Road 400 W, Middletown, IN 47356

  5937 N County Road 400 W, Middletown, IN 47356
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  $125,000 Sold Feb 28, 2025

  544 Liberty St, Middletown, IN 47356

  • 3 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • Built 1955

  Last Sold Summary

  • 19% Below List Price
  • $71/SF
  • 48 Days On Market

  Current Estimated Value $141,077

  Last Listing Agent Gadi Boukai F.C. Tucker Company

  544 Liberty St, Middletown, IN 47356
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  Est $225,349 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 3,678 Sq Ft

  6930 N Spruce St, Middletown, IN 47356

  6930 N Spruce St, Middletown, IN 47356
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  $141,175 Sold Dec 19, 2025

  0 W County Road 600 N, Middletown, IN 47356

  • Land
  • 10.13 Acres
  • $13,936 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 8 Days On Market

  Last Listing Agent Marty Dulworth RE/MAX Real Estate Solutions

  0 W County Road 600 N, Middletown, IN 47356
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  Est $322,000 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft

  6653 W County Road 675 N, Middletown, IN 47356

  6653 W County Road 675 N, Middletown, IN 47356

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