Middletown, IN Homes

• 

  

  

  /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

  

  Aubrey Walters

  eXp Realty, LLC

  1317 Cottage Ave, Middletown, IN 47356
• 

  

  

  /9

  $1,099 Per Month

  • 3 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 108, Middletown, IN 47356

  TAKE ADVANTAGE OF OUR CELEBRATE SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. If you rent this home, enjoy 1 month FREE 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

  Kameron Allen Crestwood

  27 Crestwood Dr Unit 108, 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 $129,575

  Last Listing Agent Trudy Paige AMR Real Estate LLC

  1208 Cottage Ave, Middletown, IN 47356
• 

  

  

  /29

  Est $634,023

  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
• 

  

  

  /55

  $325,700

  Pending

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

  5665 N Mechanicsburg Rd, Middletown, IN 47356

  Set on a spacious lot surrounded by mature trees, this well-maintained brick home with nearly 1600 square feet of finished living space along with multiple indoor and outdoor areas designed for both everyday living and entertaining. Located in the Shenandoah School District with convenient access to Pendleton, Anderson, Muncie, and Indianapolis, this property combines a peaceful setting with

  

  Hilary Casstevens

  Epique Inc

  5665 N Mechanicsburg Rd, Middletown, IN 47356
• 

  

  /20

  Starting at $1,004 Per Month

  • 3 - 4 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

  Crestwood MHC

  

  27 Crestwood Dr, Middletown, IN 47356
• 

  

  /44

  $649,900

  Sold Aug 11, 2025

  9247 W 650 N, Middletown, IN 47356

  • 5 Beds
  • 3 Baths
  • 5,516 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $118/SF
  • 65 Days On Market

  Current Estimated Value $662,662

  Last Listing Agent Michael Lawson Dropped Members

  9247 W 650 N, Middletown, IN 47356
• 

  

  /16

  Est $195,477

  Not Listed For Sale

  8084 N County Road 875 W, Middletown, IN 47356

  • 3 Beds
  • 1 Bath
  • 1,318 Sq Ft
  • Built 1955

  8084 N County Road 875 W, Middletown, IN 47356

  Last Sold Summary

  • 2 Days On Market
• 

  

  /5

  $690,000

  • Land
  • 30.09 Acres
  • $22,931 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

  

  Mark Dudley

  RE/MAX Realty Group

  4998 N County Road 575 W, 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 $185,491

  Last Listing Agent Dawn Cravens The Taflinger Real Estate Group

  482 N 7th St, Middletown, IN 47356
• 

  

  /5

  Est $113,894

  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
• 

  

  /39

  $189,700

  Pending

  • 2 Beds
  • 2 Baths
  • 1,280 Sq Ft

  421 Columbia Ave, Middletown, IN 47356

  Located in the Shenandoah School District, this updated 2-bedroom, 2-bath home offers nearly 1,300 square feet of living space plus a full unfinished basement and an exceptional 28' x 40' detached garage/workshop. Recent improvements include HVAC, water heater, kitchen appliances, updated flooring, paint, solid-core interior doors, updated bathrooms, and portions of the plumbing and electrical.

  

  Hilary Casstevens

  Epique Inc

  421 Columbia Ave, Middletown, IN 47356
• 

  

  /10

  $1,231 Per Month

  • 4 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 99, Middletown, IN 47356

  TAKE ADVANTAGE OF OUR CELEBRATE SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. If you rent this home, enjoy 1 month FREE rent. Plus, no application fees. Offer expires July 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
• 

  

  /13

  $168,900

  Sold Sep 23, 2025

  512 N 5th St, Middletown, IN 47356

  • 2 Beds
  • 1.5 Baths
  • 1,405 Sq Ft
  • Built 2001

  Last Sold Summary

  • $120/SF
  • 27 Days On Market

  Current Estimated Value $169,133

  Last Listing Agent Sharon Baker Carpenter, REALTORS®

  512 N 5th St, Middletown, IN 47356
• 

  

  /59

  Est $273,199

  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
• 

  

  /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.

  

  Shawn Nugent

  Highgarden Real Estate

  6770 N Rick James Dr, Middletown, IN 47356
• 

  

  /10

  $1,224 Per Month

  • 4 Beds
  • 2 Baths
  • Property for Rent

  27 Crestwood Dr Unit 102, Middletown, IN 47356

  TAKE ADVANTAGE OF OUR CELEBRATE SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent. If you rent this home, enjoy 1 month FREE 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

  Kameron Allen Crestwood

  27 Crestwood Dr Unit 102, 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 $309,492

  Last Listing Agent Shelly Hughes Indy A-Team Realty

  7255 W US Highway 36, Middletown, IN 47356
• 

  

  /30

  Est $206,021

  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
• 

  

  /22

  $199,900

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  508 N 11th St, Middletown, IN 47356

  Discover the charm of small town living at 508 N 11th ST, a single-family residence built in 1959, offering 1092 square feet of thoughtfully designed living space in MIDDLETOWN, IN. This delightful one-story home sits on an expansive 15202 square foot lot, providing ample outdoor potential. Featuring plenty of extra storage with a one car attached garage and a 24x40 detached heated garage

  

  Jon Ash

  Arc Realty

  508 N 11th St, 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
• 

  /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 $289,638

  Last Listing Agent Christina Boyland Rhodes Realty, LLC

  5571 N Raider Rd, Middletown, IN 47356
• 

  

  /47

  Est $252,127

  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
• 

  

  /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

  

  Mark Dudley

  RE/MAX Realty Group

  5579 W US Highway 36, 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 $220,116

  Last Listing Agent Lisa Buckner RE/MAX Real Estate Groups

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

  

  /46

  Est $365,472

  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
• 

  

  /30

  $246,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,584 Sq Ft

  6803 N County Road 700 W, Middletown, IN 47356

  Situated on 1.75 acres, this tri-level home offers space, functionality, and peaceful country views. Inside you’ll find 2 bedrooms, 1.5 baths, multiple living areas, a bright main living room, and a lower-level family room with fireplace. Detached garage offers extra storage and flexibility. Water heater replaced in 2024 and septic pumped in October 2025. Plenty of opportunity to make this

  

  Rachel Tucker

  RE/MAX Real Estate Groups

  6803 N County Road 700 W, 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 $91,298

  Last Listing Agent Ryan Kramer RE/MAX Real Estate Groups

  1456 Congress St, Middletown, IN 47356
• 

  

  /43

  Est $307,151

  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
• 

  

  /54

  $1

  • 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

  

  Caleb Cleek

  Jeff Boone Realty, LLC

  3793 W US Highway 36, 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 $156,799

  Last Listing Agent Christina Boyland Rhodes Realty

  1190 Cottage Ave, Middletown, IN 47356
• 

  

  /57

  Est $302,966

  Not Listed For Sale

  6221 N County Road 200 W, Middletown, IN 47356

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1949

  6221 N County Road 200 W, Middletown, IN 47356

  Last Sold Summary

  • 81 Days On Market
• 

  

  /9

  $77,999

  • 3 Beds
  • 2 Baths

  27 Crestwood Dr Unit 92, 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 on a corner lot! The home has vinyl wood flooring throughout making cleaning a breeze and a sleek finish. The kitchen is

  Kameron Allen Crestwood

  27 Crestwood Dr Unit 92, 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 $237,493

  Last Listing Agent Caleb Cleek Jeff Boone Realty, LLC

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

  

  /54

  Est $444,415

  Not Listed For Sale

  2801 W County Road 650 N, Middletown, IN 47356

  • 4 Beds
  • 2.5 Baths
  • 2,799 Sq Ft
  • Built 2002

  2801 W County Road 650 N, Middletown, IN 47356

  Last Sold Summary

  • 103 Days On Market
• 

  

  /36

  $290,000

  $25K PRICE DROP Pending

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

  8991 W State Road 236, Middletown, IN 47356

  Pack your bags and clear your calendar because it is time to stop searching and start living. This spacious three-bedroom, 2.5-bath Cape Cod is the perfect backdrop for your best summer yet. Situated on a lush 1 + acre lot within the sought-after Shenandoah School District, this home perfectly balances classic charm with modern updates. We have done the heavy lifting so you do not have to,

  Dawn McClara F.C. Tucker Company

  8991 W State Road 236, 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 $423,292

  Last Listing Agent John Rhodes III Indiana Select Realty LLC

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

  

  /31

  Est $361,330

  Not Listed For Sale

  2917 W County Road 650 N, Middletown, IN 47356

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

  2917 W County Road 650 N, Middletown, IN 47356

  Last Sold Summary

  • 49 Days On Market
• 

  

  /10

  $78,999

  • 3 Beds
  • 2 Baths

  27 Crestwood Dr Unit 84, 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. Your brand new home awaits at Crestwood and is now ready for move in! This spacious home offers vinyl wood flooring that flows seamlessly throughout the main living areas, creating a warm and inviting feel. The open kitchen is

  Kameron Allen Crestwood

  27 Crestwood Dr Unit 84, Middletown, IN 47356

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