Middletown, IN Homes

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  /37

  $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
• 

  

  

  /12

  Est $274,620

  Not Listed For Sale

  3701 N County Road 575 W, Middletown, IN 47356

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 2000

  3701 N County Road 575 W, Middletown, IN 47356

  Last Sold Summary

  • 19 Days On Market
• 

  

  

  /11

  $89,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,312 Sq Ft

  8137 N Raider Rd, Middletown, IN 47356

  Buster Johnson Buster Johnson, REALTORS®

  8137 N Raider Rd, Middletown, IN 47356
• 

  

  

  /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 $276,676

  Last Listing Agent Candy Bair RE/MAX Real Estate Solutions

  914 Maple St, Middletown, IN 47356
• 

  

  

  /6

  Est $175,174

  Not Listed For Sale

  4078 N Mechanicsburg Rd, Middletown, IN 47356

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Built 1953

  4078 N Mechanicsburg Rd, Middletown, IN 47356

  Last Sold Summary

  • 5 Days On Market
• 

  

  /36

  $279,900

  Pending

  • 3 Beds
  • 2 Baths
  • 2,132 Sq Ft

  4326 E County Road 500 S, Middletown, IN 47356

  Completely updated and move-in ready, this 3-bedroom, 2-bath home offers 2,132 finished square feet of thoughtfully renovated living space in a peaceful rural setting. Nearly every major component has been improved, giving buyers the confidence of modern systems with the charm of a well-established home. Step inside to find all new flooring throughout, including luxury vinyl plank and new carpet,

  Austin Rich NextHome Elite Real Estate

  4326 E County Road 500 S, Middletown, IN 47356
• 

  /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

  Current Estimated Value $192,719

  Last Listing Agent Caleb Cleek Jeff Boone Realty, LLC

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

  

  /47

  Est $272,742

  Not Listed For Sale

  8542 W Us Highway 36, Middletown, IN 47356

  • 4 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1957

  8542 W Us Highway 36, Middletown, IN 47356

  Last Sold Summary

  • 1 Day On Market
• 

  

  /32

  $88,999

  • 3 Beds
  • 2 Baths

  27 Crestwood Dr Unit 31, Middletown, IN 47356

  TAKE ADVANTAGE OF OUR CELEBRATE SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. Plus, no application fees. Offer expires July 31, 2026. Act fast! Restrictions apply. This spacious home offers comfortable living space. The open floor plan features attractive vinyl wood flooring throughout and a kitchen equipped with stainless steel appliances and ample cabinet

  Kameron Allen Crestwood

  27 Crestwood Dr Unit 31, Middletown, IN 47356
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  /29

  $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

  Current Estimated Value $196,440

  Last Listing Agent Jenny Shopp Berkshire Hathaway Home

  1213 W Mill St, Middletown, IN 47356
• 

  

  /53

  Est $204,427

  Not Listed For Sale

  8874 W Us Highway 36, Middletown, IN 47356

  • 3 Beds
  • 2 Baths
  • 3,408 Sq Ft
  • Built 2005

  8874 W Us Highway 36, Middletown, IN 47356

  Last Sold Summary

  • 9 Days On Market
• 

  

  /22

  $174,900

  • 3 Beds
  • 1 Bath
  • 1,864 Sq Ft

  269 N 8th St, Middletown, IN 47356

  A welcoming single-family residence built in 1900, offering 1384 square feet. This inviting home, ready for you to move in. This delightful residence features three well-proportioned bedrooms, with an additional 2 rooms upstairs that could be used as bedrooms. The home also includes a full bathroom, designed for everyday convenience. A charming porch invites you to enjoy quiet mornings or

  Christina Boyland Rhodes Realty

  269 N 8th St, Middletown, IN 47356
• 

  

  /34

  $170,000

  Sold Mar 17, 2026

  508 N 5th St, Middletown, IN 47356

  • 2 Beds
  • 1.5 Baths
  • 1,405 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $121/SF
  • 39 Days On Market

  Current Estimated Value $169,818

  Last Listing Agent Travis Smith eXp Realty LLC

  508 N 5th St, Middletown, IN 47356
• 

  

  /62

  Est $404,001

  Not Listed For Sale

  5584 N County Road 850 W, Middletown, IN 47356

  • 4 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • Built 1959

  5584 N County Road 850 W, Middletown, IN 47356

  Last Sold Summary

  • 1 Day On Market
• 

  

  /7

  $59,900

  $33K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  804 High St, Middletown, IN 47356

  Expand or jumpstart your real estate portfolio with this prime investment opportunity where the true value lies in the land with no Major work needed. Centrally located in Middletown, this property features a spacious footprint originally configured as a 2 story, 3-bedroom, 2-bathroom home. This is a true blank canvas for ambitious renovators looking to create a custom masterpiece from the ground

  Keri Hir Keri Hir

  804 High St, Middletown, IN 47356
• 

  

  /41

  $345,000

  Sold Apr 10, 2026

  6912 N County Road 700 W, Middletown, IN 47356

  • 5 Beds
  • 1.5 Baths
  • 3,782 Sq Ft
  • Built 1900

  Last Sold Summary

  • 13% Below List Price
  • $91/SF
  • 150 Days On Market

  Current Estimated Value $342,293

  Last Listing Agent Marty Dulworth RE/MAX Real Estate Solutions

  6912 N County Road 700 W, Middletown, IN 47356
• 

  

  /60

  Est $527,586

  Not Listed For Sale

  8450 W County Road 575 N, Middletown, IN 47356

  • 3 Beds
  • 3.5 Baths
  • 4,070 Sq Ft
  • Built 2002

  8450 W County Road 575 N, Middletown, IN 47356

  Last Sold Summary

  • 60 Days On Market
• 

  

  /32

  $160,000

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  1396 Congress St, Middletown, IN 47356

  Welcome home to this inviting 3-bedroom, 1-bath property situated on a spacious corner lot with a fully fenced backyard, offering both privacy and room to enjoy the outdoors. The thoughtfully designed split floorplan features two cozy bedrooms positioned on either side of the full bathroom, which was tastefully renovated in 2019. You'll appreciate the large tub with tile shower surround blending

  Heather Upton Keller Williams Indy Metro NE

  1396 Congress St, Middletown, IN 47356
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  /26

  $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 $183,823

  Last Listing Agent Steffanie Hensley REMAX ONE

  809 State St, Middletown, IN 47356
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  /37

  Est $500,773

  Not Listed For Sale

  8632 W County Road 550 N, Middletown, IN 47356

  • 3 Beds
  • 2.5 Baths
  • 2,662 Sq Ft
  • Built 2018

  8632 W County Road 550 N, Middletown, IN 47356

  Last Sold Summary

  • 26 Days On Market
• 

  

  /36

  $299,900

  $25K PRICE DROP Pending

  • 3 Beds
  • 3 Baths
  • 2,296 Sq Ft

  9124 W Wren Way, Middletown, IN 47356

  This beautifully maintained brick ranch home offers single-level living with the added versatility of a fully finished walk-out basement. Featuring 3 bedrooms and 3 full bathrooms, it provides comfortable space for both daily living and entertaining. On the main level, you'll find a spacious living room that flows into the updated kitchen (2021), complete with modern finishes and ample cabinetry.

  Steffanie Hensley REMAX ONE

  9124 W Wren Way, Middletown, IN 47356
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  /41

  $399,900

  Sold Jun 03, 2026

  4190 W County Road 700 N, Middletown, IN 47356

  • 4 Beds
  • 2.5 Baths
  • 2,068 Sq Ft
  • Built 2004

  Last Sold Summary

  • $193/SF
  • 2 Days On Market

  Current Estimated Value $396,403

  Last Listing Agent Michelle Frazier Keller Williams Indy Metro NE

  4190 W County Road 700 N, Middletown, IN 47356
• 

  

  /36

  Est $288,476

  Not Listed For Sale

  7780 W County Road 625 N, Middletown, IN 47356

  • 3 Beds
  • 2 Baths
  • 1,864 Sq Ft
  • Built 1972

  7780 W County Road 625 N, Middletown, IN 47356

  Last Sold Summary

  • 23 Days On Market
• 

  

  /33

  $240,000

  Pending

  • 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 windows

  Megan Silva RE/MAX Real Estate Solutions

  503 N 10th St, Middletown, IN 47356
• 

  

  /28

  $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

  Current Estimated Value $221,757

  Last Listing Agent Steffanie Hensley REMAX ONE

  815 Maple St, Middletown, IN 47356
• 

  

  /30

  Est $241,218

  Not Listed For Sale

  5036 N Raider Rd, Middletown, IN 47356

  • 3 Beds
  • 1.5 Baths
  • 1,544 Sq Ft
  • Built 1950

  5036 N Raider Rd, Middletown, IN 47356

  Last Sold Summary

  • 69 Days On Market
• 

  

  /10

  $77,999

  • 3 Beds
  • 2 Baths

  27 Crestwood Dr Unit 15, Middletown, IN 47356

  TAKE ADVANTAGE OF OUR CELEBRATE SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. Plus, no application fees. Offer expires July 31, 2026. Act fast! Restrictions apply. Welcome to this thoughtfully upgraded home located in the heart of Crestwood! The home has vinyl wood flooring throughout making cleaning a breeze and a sleek finish. The kitchen is equipped with

  Kameron Allen Crestwood

  27 Crestwood Dr Unit 15, Middletown, IN 47356
• 

  

  /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 $161,812

  Last Listing Agent Robyn Breece @properties

  127 N 8th St, Middletown, IN 47356
• 

  

  /43

  Est $460,105

  Not Listed For Sale

  5863 W County Road 600 N, Middletown, IN 47356

  • 4 Beds
  • 2.5 Baths
  • 4,011 Sq Ft
  • Built 1991

  5863 W County Road 600 N, Middletown, IN 47356

  Last Sold Summary

  • 4 Days On Market
• 

  

  /9

  $69,999

  • 3 Beds
  • 2 Baths

  27 Crestwood Dr Unit 94, Middletown, IN 47356

  TAKE ADVANTAGE OF OUR CELEBRATE SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. Plus, no application fees. Offer expires July 31, 2026. Act fast! Restrictions apply. Welcome to this thoughtfully upgraded home located in the heart of Crestwood! The home has vinyl wood flooring throughout making cleaning a breeze and a sleek finish. The kitchen is equipped with

  Kameron Allen Crestwood

  27 Crestwood Dr Unit 94, Middletown, IN 47356
• 

  

  /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

  Current Estimated Value $144,860

  Last Listing Agent Christina Boyland Rhodes Realty, LLC

  829 High St, Middletown, IN 47356
• 

  

  /14

  Est $337,384

  Not Listed For Sale

  5937 N County Road 400 W, Middletown, IN 47356

  • 4 Beds
  • 2 Baths
  • 2,338 Sq Ft
  • Built 1977

  5937 N County Road 400 W, Middletown, IN 47356

  Last Sold Summary

  • 57 Days On Market
• 

  

  /11

  $77,999

  • 3 Beds
  • 2 Baths

  27 Crestwood Dr Unit 86, Middletown, IN 47356

  TAKE ADVANTAGE OF OUR CELEBRATE SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. Offer expires July 31, 2026. Act fast! Restrictions apply. Welcome to this thoughtfully upgraded home located in the heart of Crestwood! The home has vinyl wood flooring throughout making cleaning a breeze and a sleek finish. The kitchen is equipped with upgraded smart stainless steel

  Kameron Allen Crestwood

  27 Crestwood Dr Unit 86, Middletown, IN 47356
• 

  

  /22

  $229,000

  Sold Apr 15, 2026

  683 N 5th St, Middletown, IN 47356

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • Built 1995

  Last Sold Summary

  • 8% Below List Price
  • $116/SF
  • 12 Days On Market

  Current Estimated Value $236,262

  Last Listing Agent Marty Dulworth RE/MAX Real Estate Solutions

  683 N 5th St, Middletown, IN 47356
• 

  

  /50

  Est $280,559

  Not Listed For Sale

  6653 W County Road 675 N, Middletown, IN 47356

  • 3 Beds
  • 1 Bath
  • 1,420 Sq Ft
  • Built 1930

  6653 W County Road 675 N, Middletown, IN 47356

  Last Sold Summary

  • 2 Days On Market
• 

  

  /10

  $68,999

  • 3 Beds
  • 2 Baths

  27 Crestwood Dr Unit 98, Middletown, IN 47356

  TAKE ADVANTAGE OF OUR CELEBRATE SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. Plus, no application fees. Offer expires July 31, 2026. Act fast! Restrictions apply. Welcome to this thoughtfully upgraded home located in the heart of Crestwood! The home has vinyl wood flooring throughout making cleaning a breeze and a sleek finish. The kitchen is equipped with

  Kameron Allen Crestwood

  27 Crestwood Dr Unit 98, Middletown, IN 47356
• 

  

  /80

  $805,000

  Sold Mar 31, 2026

  5333 S County Road 450 E, Middletown, IN 47356

  • 3 Beds
  • 2.5 Baths
  • 2,706 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Above List Price
  • $297/SF
  • 2 Days On Market

  Current Estimated Value $809,354

  Last Listing Agent Michelle Frazier Keller Williams Indy Metro NE

  5333 S County Road 450 E, Middletown, IN 47356
• 

  

  /26

  Est $314,221

  Not Listed For Sale

  6925 N Rick James Dr, Middletown, IN 47356

  • 3 Beds
  • 2.5 Baths
  • 2,320 Sq Ft
  • Built 1981

  6925 N Rick James Dr, Middletown, IN 47356

  Last Sold Summary

  • 0 Days On Market
• 

  

  /27

  $135,000

  $5K PRICE DROP Pending

  • 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
• 

  

  /23

  $209,900

  Sold May 08, 2026

  803 High St, Middletown, IN 47356

  • 6 Beds
  • 3 Baths
  • 2,864 Sq Ft
  • Built 1900

  Last Sold Summary

  • $73/SF
  • 10 Days On Market

  Current Estimated Value $204,926

  Last Listing Agent Lucero Vargas RE/MAX Complete

  803 High St, Middletown, IN 47356

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