2,643

Middletown, IN Homes

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  • /30

    $125,000

    • 3 Beds
    • 2 Baths
    • 2,128 Sq Ft

    1317 Cottage Ave, Middletown, IN 47356

    Country Charm just waiting on some finishing touches! This home offers 3 bedrooms, two bathrooms and 2128 square feet of comfortable living space across 1.5 stories. From the newer flooring in the entryway and newer vinyl windows throughout this home has alot to offer. Large sun filled living room with hardwood floors, wood beams and some newer light fixtures to keep the country appeal. Spacious

    Agent Photo

    Aubrey Walters

    eXp Realty LLC

    1317 Cottage Ave, Middletown, IN 47356
  • /11

    $1,205 Per Month

    • 3 Beds
    • 2 Baths
    • Property for Rent

    27 Crestwood Dr Unit 15, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR END OF SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. If you rent this home, enjoy 2 months FREE rent. Plus, no application fees. Offer expires August 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

    Kameron Allen Crestwood

    27 Crestwood Dr Unit 15, Middletown, IN 47356
  • /39

    $125,000

    Sold Feb 20, 2026

    1208 Cottage Ave, Middletown, IN 47356

    • 3 Beds
    • 2 Baths
    • 2,072 Sq Ft
    • Built 1900

    Last Sold Summary

    • 11% Below List Price
    • $60/SF
    • 8 Days On Market

    Current Estimated Value $133,546

    Last Listing Agent Trudy Paige AMR Real Estate LLC

    1208 Cottage Ave, Middletown, IN 47356
    • /22

      Est $213,655

      Not Listed For Sale

      975 Locust St, Middletown, IN 47356

      • 3 Beds
      • 2 Baths
      • 1,765 Sq Ft
      • Built 1972
      975 Locust St, Middletown, IN 47356

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Julie Schnepp RE/MAX Legacy

  • /35

    $335,000

    $110K PRICE INCREASE Pending
    • 3 Beds
    • 1 Bath
    • 1,932 Sq Ft

    5579 W US Highway 36, Middletown, IN 47356

    Step back in time with this turn-of-the-century country farmhouse situated on 11.24 acres just east of Anderson along US HWY 36. Offering a classic rural setting, this spacious home features 10 rooms, including 3 bedrooms, 1 full bath, and a welcoming sunroom that overlooks the surrounding countryside. Recent updates include a newer roof and select replacement windows, while the home retains its

    Agent Photo

    Mark Dudley

    RE/MAX Realty Group

    5579 W US Highway 36, Middletown, IN 47356
  • /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

    Kameron Allen Crestwood

    27 Crestwood Dr Unit 37, Middletown, IN 47356
  • /34

    $179,900

    Sold Aug 27, 2025

    482 N 7th St, Middletown, IN 47356

    • 3 Beds
    • 1 Bath
    • 1,153 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Below List Price
    • $156/SF
    • 59 Days On Market

    Current Estimated Value $187,811

    Last Listing Agent Dawn Cravens The Taflinger Real Estate Group

    482 N 7th St, Middletown, IN 47356
    • /2

      Est $147,596

      Not Listed For Sale

      1256 Locust St, Middletown, IN 47356

      • 4 Beds
      • 2 Baths
      • 1,547 Sq Ft
      • Built 1900
      1256 Locust St, Middletown, IN 47356

  • /54

    $2

    Pending
    • 3 Beds
    • 1 Bath
    • 1,590 Sq Ft

    3793 W US Highway 36, Middletown, IN 47356

    To be sold in an Online Only Auction on Monday, August 3rd @ 6 PM EST. A total of two parcels being offered in separate lots. Lot 1 is the Home, Barns, and 3.09 +/- Acres. Lot 2 is 5.05 +/- Acres that is currently a hay field. Both located in Jefferson Township of Henry County Indiana with Shenandoah Schools. Lot 1 features the 3 Bed / 1 Bath & 1,590 sqft brick ranch home. This home has a wood

    Agent Photo

    Caleb Cleek

    Jeff Boone Realty, LLC

    3793 W US Highway 36, Middletown, IN 47356
  • /27

    $1,205 Per Month

    • 4 Beds
    • 2 Baths
    • Property for Rent

    27 Crestwood Dr Unit 99, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR END OF SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. If you rent this home, enjoy 2 months FREE rent. Plus, no application fees. Offer expires August 31, 2026. Act fast! Restrictions apply. Welcome to this thoughtfully upgraded home in a premier spot located in the heart of Crestwood! The home has vinyl wood flooring throughout making

    Kameron Allen Crestwood

    27 Crestwood Dr Unit 99, Middletown, IN 47356
  • /40

    $315,000

    Sold Mar 20, 2026

    7255 W US Highway 36, Middletown, IN 47356

    • 2 Beds
    • 1 Bath
    • 1,474 Sq Ft
    • Built 1900

    Last Sold Summary

    • $214/SF
    • 20 Days On Market

    Current Estimated Value $315,167

    Last Listing Agent Shelly Hughes Indy A-Team Realty

    7255 W US Highway 36, Middletown, IN 47356
    • /44

      Est $663,813

      Not Listed For Sale

      9247 W 650 N, Middletown, IN 47356

      • 5 Beds
      • 3 Baths
      • 5,516 Sq Ft
      • Built 2005
      9247 W 650 N, Middletown, IN 47356

      Last Sold Summary

      • 65 Days On Market

      Last Listing Agent Michael Lawson Dropped Members

  • /5

    $570,000

    $120K PRICE DROP
    • Land
    • 30.09 Acres
    • $18,943 per Acre

    4998 N County Road 575 W, Middletown, IN 47356

    Situated at the corner of County Road 575 West and State Road 36, this 30.09-acre tract offers a unique combination of productive farm ground and valuable development potential. The corner four acres are zoned for storage buildings and include a 4,000-square-foot central storage building already in place. Drainage has been installed, and zoning and approvals are complete with the county. In

    Agent Photo

    Mark Dudley

    RE/MAX Realty Group

    4998 N County Road 575 W, Middletown, IN 47356
  • /13

    $1,226 Per Month

    • 3 Beds
    • 2 Baths
    • Property for Rent

    27 Crestwood Dr Unit 86, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR END OF SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. If you rent this home, enjoy 2 months FREE rent. Plus, no application fees. Offer expires August 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

    Kameron Allen Crestwood

    27 Crestwood Dr Unit 86, Middletown, IN 47356
  • /2

    $275,000

    Sold Nov 12, 2025

    5571 N Raider Rd, Middletown, IN 47356

    • 3 Beds
    • 1 Bath
    • 1,875 Sq Ft
    • Built 2002

    Last Sold Summary

    • 15% Below List Price
    • $147/SF
    • 72 Days On Market

    Current Estimated Value $294,545

    Last Listing Agent Christina Boyland Rhodes Realty, LLC

    5571 N Raider Rd, Middletown, IN 47356
    • /3

      Not Listed For Sale

      Unlisted Address

      • 4 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1995
      Unlisted Address

      Last Sold Summary

      Last Listing Agent Sherri Humes Dropped Members

  • /29

    $150,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft

    6770 N Rick James Dr, Middletown, IN 47356

    Welcome Home! 1.21 Acre 3 BDR 2.5BA 2CAR. Metal Roof for low maintenance. Windows were replaced within last 10 years. Open concept. Primary BDR has ensuite & His/Hers Closets. Newer 27x24 garage with it's own electrical panel. Lots of storage! Wet bar. Mature trees! Quiet setting. 15 minutes to Pendleton & 15 minutes to shopping in Anderson. Estate.

    Agent Photo

    Shawn Nugent

    Highgarden Real Estate

    6770 N Rick James Dr, Middletown, IN 47356
  • /27

    $1,205 Per Month

    • 4 Beds
    • 2 Baths
    • Property for Rent

    27 Crestwood Dr Unit 102, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR END OF SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. If you rent this home, enjoy 2 months FREE rent. Plus, no application fees. Offer expires August 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

    Kameron Allen Crestwood

    27 Crestwood Dr Unit 102, Middletown, IN 47356
  • /55

    $310,000

    Sold Jul 17, 2026

    5665 N Mechanicsburg Rd, Middletown, IN 47356

    • 3 Beds
    • 2.5 Baths
    • 1,596 Sq Ft
    • Built 1965

    Last Sold Summary

    • 5% Below List Price
    • $194/SF
    • 27 Days On Market

    Current Estimated Value $320,653

    Last Listing Agent Hilary Casstevens Epique Inc

    5665 N Mechanicsburg Rd, Middletown, IN 47356
    • /29

      Est $648,436

      Not Listed For Sale

      7263 N County Road 700 W, Middletown, IN 47356

      • 232 Beds
      • 5 Baths
      • 3,058 Sq Ft
      • Built 2008
      7263 N County Road 700 W, Middletown, IN 47356

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Diana Martin NonMember MEIAR

  • /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
  • /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

    Kameron Allen Crestwood

    27 Crestwood Dr Unit 22, Middletown, IN 47356
  • /21

    $215,000

    Sold Oct 10, 2025

    11801 S County Road 600 W, Middletown, IN 47356

    • 2 Beds
    • 2 Baths
    • 1,502 Sq Ft
    • Built 1941

    Last Sold Summary

    • $143/SF
    • 26 Days On Market

    Current Estimated Value $227,080

    Last Listing Agent Lisa Buckner RE/MAX Real Estate Groups

    11801 S County Road 600 W, Middletown, IN 47356
    • /5

      Est $120,162

      Not Listed For Sale

      1459 Congress St, Middletown, IN 47356

      • 4 Beds
      • 2 Baths
      • 3,248 Sq Ft
      • Built 1970
      1459 Congress St, Middletown, IN 47356

      Last Sold Summary

      • 73 Days On Market

      Last Listing Agent Christina Boyland Rhodes Realty, LLC

  • /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
  • /36

    $285,000

    Sold Aug 10, 2026

    8991 W State Road 236, Middletown, IN 47356

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft
    • Built 1994

    Last Sold Summary

    • 10% Below List Price
    • $110/SF
    • 71 Days On Market

    Current Estimated Value $294,334

    Last Listing Agent Dawn McClara F.C. Tucker Company

    8991 W State Road 236, Middletown, IN 47356
    • /59

      Est $319,328

      Not Listed For Sale

      818 Cossack Dr, Middletown, IN 47356

      • 4 Beds
      • 1,152 Sq Ft
      • Built 1971
      818 Cossack Dr, Middletown, IN 47356

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Schuyler Estes RE/MAX Real Estate Solutions

  • /86

    $459,000

    • 4 Beds
    • 2.5 Baths
    • 2,048 Sq Ft

    8271 W County Road 700 N, Middletown, IN 47356

    Looking for land that's *already set up* for the lifestyle you want? This 10 acre property is a homesteader's dream - huge pole barn with double doors(incl concrete floors and electricity), heated greenhouse, garden space, a fenced area ideal for a potager garden or chicken run, and plenty of cleared areas for walking, projects, or expanding your farm. The home offers 4 bedrooms, 2.5 baths,

    Kristi Covey Real Broker, LLC

    8271 W County Road 700 N, Middletown, IN 47356
  • /17

    $94,250

    Sold May 01, 2026

    1456 Congress St, Middletown, IN 47356

    • 1 Bed
    • 1 Bath
    • 576 Sq Ft
    • Built 1948

    Last Sold Summary

    • 1% Below List Price
    • $164/SF
    • 53 Days On Market

    Current Estimated Value $91,378

    Last Listing Agent Ryan Kramer RE/MAX Real Estate Groups

    1456 Congress St, Middletown, IN 47356
    • /30

      Est $211,083

      Not Listed For Sale

      2483 W County Road 400 N, Middletown, IN 47356

      • 3 Beds
      • 1 Bath
      • 2,127 Sq Ft
      • Built 1915
      2483 W County Road 400 N, Middletown, IN 47356

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent Rachel Mappes F.C. Tucker Company

  • /23

    $149,900

    • 3 Beds
    • 1 Bath
    • 980 Sq Ft

    1318 Cottage Ave, Middletown, IN 47356

    Discover 1318 Cottage AVE, a meticulously maintained single-family residence in MIDDLETOWN, IN, offering 980 square feet of thoughtfully designed living space. Constructed in 1960, this inviting home presents a ready-to-move-in condition, embodying comfort and functionality. The residence features three well-proportioned bedrooms, providing ample private accommodations. A full bathroom serves

    Christina Boyland Rhodes Realty, LLC

    1318 Cottage Ave, Middletown, IN 47356
  • /14

    $158,900

    Sold Apr 10, 2026

    1190 Cottage Ave, Middletown, IN 47356

    • 3 Beds
    • 2 Baths
    • 1,226 Sq Ft
    • Built 1900

    Last Sold Summary

    • $130/SF
    • 88 Days On Market

    Current Estimated Value $156,277

    Last Listing Agent Christina Boyland Rhodes Realty

    1190 Cottage Ave, Middletown, IN 47356
    • /47

      Est $255,995

      Not Listed For Sale

      4396 N County Road 200 W, Middletown, IN 47356

      • 3 Beds
      • 2 Baths
      • 2,695 Sq Ft
      • Built 1924
      4396 N County Road 200 W, Middletown, IN 47356

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Caleb Cleek Jeff Boone Realty, LLC

  • /49

    $599,900

    $25K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 3,236 Sq Ft

    4879 S County Road 350 E, Middletown, IN 47356

    Come see this wonderful 7.3 acre country setting in highly desirable Pendleton Schools! Only minutes from restaurants, shopping and I-69. This well-maintained 100+ year old farmhouse has loads of possibilities with 4 bedrooms, 2 baths, and over 3,000 sf. With only 1 bathroom upstairs w/ tub (no shower), renovations and updating will likely be desired. Lots of main level rooms to spread out and

    Brian Hicks Lawyers Realty, LLC

    4879 S County Road 350 E, Middletown, IN 47356
  • /35

    $233,295

    Sold Nov 07, 2025

    5080 S County Road 450 E, Middletown, IN 47356

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 2002

    Last Sold Summary

    • 23,329,400% Above List Price
    • $168/SF
    • 28 Days On Market

    Current Estimated Value $250,255

    Last Listing Agent Caleb Cleek Jeff Boone Realty, LLC

    5080 S County Road 450 E, Middletown, IN 47356
    • /46

      Est $358,741

      Not Listed For Sale

      4700 N County Road 300 W, Middletown, IN 47356

      • 5 Beds
      • 5 Baths
      • 3,754 Sq Ft
      • Built 1977
      4700 N County Road 300 W, Middletown, IN 47356

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent John Rhodes III Indiana Select Realty LLC

  • /20

    $172,000

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

    512 N 5th St, Middletown, IN 47356

    Ready for a delightful discovery? At 512 N 5th ST in MIDDLETOWN, IN, you'll find a charming 1405 square foot single-family ranch-style residence, built in 2001 and absolutely ready for its next adventure. This inviting home is just waiting to sprinkle a little joy into your everyday. Step into the heart of the home, where the kitchen is practically winking at you with its island - perfect for

    Sam Johnson F.C. Tucker/Prosperity

    512 N 5th St, Middletown, IN 47356
  • /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

    Current Estimated Value $427,052

    Last Listing Agent John Rhodes III Indiana Select Realty LLC

    6755 W County Road 675 N, Middletown, IN 47356
    • /43

      Est $302,611

      Not Listed For Sale

      5431 N County Road 200 W, Middletown, IN 47356

      • 3 Beds
      • 2 Baths
      • 1,749 Sq Ft
      • Built 1965
      5431 N County Road 200 W, Middletown, IN 47356

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Steffanie Hensley REMAX ONE

  • /22

    $324,000

    $15K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 2,219 Sq Ft

    5634 N Quail Ln, Middletown, IN 47356

    Welcome home to this spacious 4-bedroom, 2-bath all-brick ranch situated on 0.78 acres in a quiet, peaceful neighborhood just south of Middletown. With generous living space inside and plenty of room to enjoy outdoors, this property offers comfort, flexibility, and classic ranch-style convenience. The main level features two separate living areas, perfect for relaxing, entertaining, or creating a

    James Shroyer Flesher Brothers Auctioneering & Real Estate Inc.

    5634 N Quail Ln, Middletown, IN 47356

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$191,500
Median Single Family Sale Price
$190,000
Median Townhouse Sale Price
$599,900
Median 2 Bedroom Sale Price
$169,450
Median 1 Bedroom Sale Price
$94,250
Average Price Per Sq Ft
$133
Number of Homes for Sale
12
Last 12 months Home Sales
74
Months of Supply
1.90
Median List Price
$194,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
0%
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