Middletown, IN Homes

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  $129,900

  • 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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  /25

  $1,199 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 76, Middletown, IN 47356

  FIND A HOME FOR THE HOLIDAYS! 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! Offers expire December 19, 2025. 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 76, Middletown, IN 47356
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  /58

  $407,000 Sold Sep 22, 2025

  6755 W County Road 675 N, Middletown, IN 47356

  • 4 Beds
  • 3 Baths
  • 2,190 Sq Ft
  • Built 1993

  Last Sold Summary

  • $186/SF
  • 1 Day On Market

  Last Listing Agent John Rhodes III Indiana Select Realty LLC

  6755 W County Road 675 N, Middletown, IN 47356
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  /6

  Est $204,263 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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  /56

  $250,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,548 Sq Ft

  9294 W County Road 950 N, Middletown, IN 47356

  Auction - Saturday, November 22nd at 10:00 a.m. Don't miss this once-in-a-lifetime opportunity to own over 12 acres featuring a well-maintained 2,500 sq. ft. home with 3 bedrooms and 2 full baths. This inviting property offers endless potential and serves as the perfect canvas for your updates and personal style. A 1,200 sq. ft. pole barn provides ample space for storage, hobbies, or a workshop,

  Jason Snider J. Snider Real Estate

  9294 W County Road 950 N, Middletown, IN 47356
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  /38

  $1,194 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 70, Middletown, IN 47356

  FIND A HOME FOR THE HOLIDAYS! 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! Offers expire December 19, 2025. 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 70, 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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  /54

  Est $438,461 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
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  /16

  $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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  $1,199 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 97, Middletown, IN 47356

  FIND A HOME FOR THE HOLIDAYS! 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! Offers expire December 19, 2025. Act Fast! Restrictions apply. Looking for your dream home at an unbeatable price? This stunning brand new home offers modern living with all the extras. Features Include: Spacious Open Concept

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 97, Middletown, IN 47356
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  /33

  $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 $280,583

  Last Listing Agent Candy Bair RE/MAX Real Estate Solutions

  914 Maple St, Middletown, IN 47356
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  /12

  Est $228,231 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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  /10

  $45,000 Pending

  • 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
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  $1,194 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 68, Middletown, IN 47356

  FIND A HOME FOR THE HOLIDAYS! 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! Offers expire December 19, 2025. 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 68, Middletown, IN 47356
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  /2

  $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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  /47

  Est $240,976 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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  /23

  $59,900 Pending

  • 3 Beds
  • 1 Bath
  • 939 Sq Ft

  309 N 8th St, Middletown, IN 47356

  Spacious 3-bedroom, 1-bath home in the heart of Middletown! Features include vinyl siding, metal roof, newer gas furnace and water heater, fenced back yard, and two storage sheds. Off-street parking and a convenient small-town location close to schools, shops, and local amenities. Interior will require some TLC, but offers a great opportunity to bring this property back to life and build equity

  Brad Taflinger The Taflinger Real Estate Group

  309 N 8th St, Middletown, IN 47356
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  /28

  $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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  $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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  /39

  Est $404,151 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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  /30

  $1,199 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 28, Middletown, IN 47356

  FIND A HOME FOR THE HOLIDAYS! 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! Offers expire December 19, 2025. 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

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 28, Middletown, IN 47356
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  /25

  $180,000 Sold Jan 03, 2025

  1301 Locust St, Middletown, IN 47356

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft
  • Built 1966

  Last Sold Summary

  • 20% Below List Price
  • $106/SF
  • 98 Days On Market

  Current Estimated Value $194,250

  Last Listing Agent Matthew Wehner Gardner Property Group

  1301 Locust St, Middletown, IN 47356
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  /50

  Est $243,945 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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  /40

  $1,204 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 103, Middletown, IN 47356

  FIND A HOME FOR THE HOLIDAYS! 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! Offers expire December 19, 2025. 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,

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 103, Middletown, IN 47356
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  /31

  $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 $325,646

  Last Listing Agent Laura Wright PPG Real Estate LLC

  2917 W County Road 650 N, Middletown, IN 47356
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  /62

  Est $377,793 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
• 

  

  /23

  $1,199 per month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 24, Middletown, IN 47356

  FIND A HOME FOR THE HOLIDAYS! 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! Offers expire December 19, 2025. 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

  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 $151,264

  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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  /29

  $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 $171,799

  Last Listing Agent Steffanie Hensley RE/MAX At The Crossing

  809 State St, Middletown, IN 47356
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  /37

  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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  /26

  $1,099 per month

  • 2 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 73, Middletown, IN 47356

  FIND A HOME FOR THE HOLIDAYS! 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! Offers expire December 19, 2025. Act Fast! Restrictions apply. Take a look at this charming home coming soon at Crestwood in Middletown, IN! This open concept floor plan offers a warm and inviting flow throughout. The vinyl wood

  Nathan Fles Crestwood

  27 Crestwood Dr Unit 73, Middletown, IN 47356
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  /50

  $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 $144,668

  Last Listing Agent Caleb Cleek Jeff Boone Realty, LLC

  9031 W Us Highway 36, Middletown, IN 47356
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  /36

  Est $288,757 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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  /35

  $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 $161,589

  Last Listing Agent Robyn Breece @properties

  127 N 8th St, Middletown, IN 47356
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  /27

  Est $295,383 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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  /37

  $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 $322,955 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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  /29

  $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 $137,716

  Last Listing Agent Gadi Boukai F.C. Tucker Company

  544 Liberty St, Middletown, IN 47356

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