2,674

Middletown, IN Homes

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  • /32

    $147,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,195 Sq Ft

    902 Progress St, Middletown, IN 47356

    Welcome home to this updated 3-bedroom, 2 full bath home in Middletown located in the Shenandoah School District. Offering small-town charm with everyday convenience, this move-in ready property is ideal for first-time home buyers, growing families, or investors looking to expand their portfolio. Updates within the last two years include flooring and fresh paint throughout, creating a clean and

    Agent Photo

    Hilary Casstevens

    Epique Inc

    (844) 656-8314

    902 Progress St, Middletown, IN 47356
  • /20

    $1,124 - $1,499 per month

    Crestwood MHC

    3 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

    27 Crestwood Dr, 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 $130,007

    Last Listing Agent Trudy Paige AMR Real Estate LLC

    1208 Cottage Ave, Middletown, IN 47356
    • /47

      Est $243,211 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

      • 8% Above List Price
      • $84/SF
      • 28 Days On Market
      • Last Sold Price $225,055
      • Apr 28, 2025

      Last Listing Agent Caleb Cleek Jeff Boone Realty, LLC

  • /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

    Agent Photo

    Mark Dudley

    RE/MAX Realty Group

    (844) 703-6582

    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
  • /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 $643,990

    Last Listing Agent Michael Lawson Dropped Members

    9247 W 650 N, Middletown, IN 47356
    • /43

      Est $479,129 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

      • 2% Above List Price
      • $117/SF
      • 4 Days On Market
      • Last Sold Price $467,500
      • Apr 23, 2025

      Last Listing Agent Marty Dulworth RE/MAX Real Estate Solutions

  • /40

    $2 Pending

    • 2 Beds
    • 1 Bath
    • 2,268 Sq Ft

    4351 N County Road 575 W, Middletown, IN 47356

    To be sold in an Online Only Auction on Monday, April 6th @ 4 PM EST. Take notice of this great local estate auction! Starting off with this 2 bedroom and 1 bathroom home on 10 +/- acres in Middletown, IN! A must see property ready for its new owners. A large barn for storage and other activities. Large open barn for parking and covered storage. Big pasture space. The home is ready for your ideas

    Agent Photo

    Caleb Cleek

    Jeff Boone Realty, LLC

    (888) 984-7431

    4351 N County Road 575 W, Middletown, IN 47356
  • /17

    $1,400 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • House for Rent

    1257 Congress St, Middletown, IN 47356

    This spacious, newly renovated 3 bedroom, 2 bath home features new paint, new vinyl plank flooring throughout, new kitchencabinets and counter tops.Your family will love the enormous open concept living room and dining room for all of your entertainment needs.This home has plenty of storage throughout including the utility and launry rooms, as well as the outdoor shed.The

    1257 Congress St, 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 $184,293

    Last Listing Agent Dawn Cravens The Taflinger Real Estate Group

    482 N 7th St, Middletown, IN 47356
    • /29

      Est $641,351 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

      • 12% Above List Price
      • $188/SF
      • 53 Days On Market
      • Last Sold Price $575,000
      • Oct 06, 2023

      Last Listing Agent Diana Martin NonMember MEIAR

  • /35

    $335,000

    • 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

    (833) 382-9963

    5579 W US Highway 36, 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
  • /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 $174,333

    Last Listing Agent Sharon Baker Carpenter, REALTORS®

    512 N 5th St, Middletown, IN 47356
    • /16

      Est $179,262 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

      • 19% Above List Price
      • $114/SF
      • 2 Days On Market
      • Last Sold Price $150,500
      • Jul 28, 2023

      Last Listing Agent Mary Cordle Berkshire Hathaway Indiana Realty

  • /14

    $158,900 Pending

    • 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

    1190 Cottage Ave, Middletown, IN 47356
  • /14

    $895 per month

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • 803-807 High Street

    803-807 High St Unit 805 High Street, Middletown, IN 47356

    803-807 High St Unit 805 High Street, 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 $310,177

    Last Listing Agent Shelly Hughes Indy A-Team Realty

    7255 W US Highway 36, Middletown, IN 47356
    • /5

      Est $113,764 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

      • 153% Above List Price
      • $14/SF
      • 73 Days On Market
      • Last Sold Price $45,000
      • Feb 05, 2024

      Last Listing Agent Christina Boyland Rhodes Realty, LLC

  • /41

    $399,900 Pending

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

    4190 W County Road 700 N, Middletown, IN 47356

    COUNTRY LIVING at its best! Sitting on 5 acres, this 2004 built two-story is ready for you to make your HOME! Enjoy 9 ft ceilings throughout the main level. The large Great Room with corner, wood burning fireplace opens into the functional Kitchen with all appliances. A formal Dining Room completes the main level. The primary suite offers an en suite bath with double sinks, a garden tub, full

    Michelle Frazier Keller Williams Indy Metro NE

    4190 W County Road 700 N, Middletown, IN 47356
  • /15

    $895 per month

    • 2 Beds
    • 1 Bath
    • 725 Sq Ft
    • 803-807 High Street

    803-807 High St Unit 807 High Street, Middletown, IN 47356

    803-807 High St Unit 807 High Street, Middletown, IN 47356
  • /6

    $165,000 Sold May 16, 2025

    4078 N Mechanicsburg Rd, Middletown, IN 47356

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

    Last Sold Summary

    • 3% Above List Price
    • $110/SF
    • 5 Days On Market

    Current Estimated Value $174,660

    Last Listing Agent Buster Johnson Buster Johnson, REALTORS®

    4078 N Mechanicsburg Rd, Middletown, IN 47356
    • /59

      Est $290,262 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

      • 17% Below List Price
      • $304/SF
      • 2 Days On Market
      • Last Sold Price $350,000
      • Jul 26, 2024

      Last Listing Agent Schuyler Estes RE/MAX Real Estate Solutions

  • /36

    $319,900

    • 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 RE/MAX At The Crossing

    9124 W Wren Way, 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 $283,055

    Last Listing Agent Christina Boyland Rhodes Realty, LLC

    5571 N Raider Rd, Middletown, IN 47356
    • /30

      Est $208,352 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

      • 11% Above List Price
      • $88/SF
      • 77 Days On Market
      • Last Sold Price $188,000
      • Oct 16, 2024

      Last Listing Agent Rachel Mappes F.C. Tucker Company

  • /27

    $279,000

    • 3 Beds
    • 1 Bath
    • 1,530 Sq Ft

    2533 W US Highway 36, Middletown, IN 47356

    Escape the hustle and embrace the serenity of country living with this charming 3-bedroom, 1-bath home. Step inside and you'll immediately notice the fresh, move-in-ready feel throughout. Brand new carpet and freshly painted walls give every room a crisp, clean start. The kitchen has been thoughtfully updated with new appliances and the spacious laundry features an updated washer and dryer.

    Michael Nauman RE/MAX Advanced Realty

    2533 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 $212,679

    Last Listing Agent Lisa Buckner RE/MAX Real Estate Groups

    11801 S County Road 600 W, Middletown, IN 47356
    • /46

      Est $342,170 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

      • 20% Above List Price
      • $76/SF
      • 43 Days On Market
      • Last Sold Price $285,000
      • Feb 28, 2024

      Last Listing Agent John Rhodes III Indiana Select Realty LLC

  • /27

    $135,000

    • 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
  • /27

    $200,000 Sold May 09, 2025

    602 Liberty St, Middletown, IN 47356

    • 3 Beds
    • 2 Baths
    • 1,423 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Above List Price
    • $141/SF
    • 34 Days On Market

    Current Estimated Value $208,734

    Last Listing Agent Oksana Minkevych Trueblood Real Estate

    602 Liberty St, Middletown, IN 47356
    • /43

      Est $272,537 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

      • 4% Above List Price
      • $149/SF
      • 2 Days On Market
      • Last Sold Price $261,000
      • Sep 29, 2023

      Last Listing Agent Steffanie Hensley RE/MAX At The Crossing

  • /22

    $324,000

    • 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
  • /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 $234,497

    Last Listing Agent Caleb Cleek Jeff Boone Realty, LLC

    5080 S County Road 450 E, Middletown, IN 47356
    • /6

      Est $190,657 Not Listed For Sale

      2121 W County Road 575 N, Middletown, IN 47356

      • 3 Beds
      • 1 Bath
      • 1,788 Sq Ft
      • Built 1955
      2121 W County Road 575 N, Middletown, IN 47356

      Last Sold Summary

      • 25% Above List Price
      • $85/SF
      • 75 Days On Market
      • Last Sold Price $152,000
      • May 22, 2023

      Last Listing Agent Michelle Drumm Rhodes Realty, LLC

  • /32

    $225,000 Pending

    • 2 Beds
    • 2 Baths
    • 1,158 Sq Ft

    4978 E State Road 236, Middletown, IN 47356

    Enjoy peaceful country living in this 2-bedroom, 2-bath ranch home, perfectly situated on a spacious half-acre lot with scenic backyard views and a fully fenced-in backyard-ideal for pets, play, or outdoor entertaining. Conveniently located just minutes from the I-69 exit and nearby shopping, this property offers the perfect balance of rural charm and accessibility. The home features two

    Schuyler Estes RE/MAX Real Estate Solutions

    4978 E 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 $416,708

    Last Listing Agent John Rhodes III Indiana Select Realty LLC

    6755 W County Road 675 N, Middletown, IN 47356
    • /57

      Est $293,950 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

      • 13% Above List Price
      • $135/SF
      • 81 Days On Market
      • Last Sold Price $260,000
      • Dec 27, 2024

      Last Listing Agent Jeff Weightman Weightman Realty Group, LLC

  • /44

    $310,000

    • 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 1.23-acre lot within the Shenandoah School District, this home perfectly balances classic charm with modern updates. We have done the heavy lifting so you do not have to, featuring many

    Dawn McClara F.C. Tucker Company

    8991 W State Road 236, Middletown, IN 47356

Showing Results 1 - 40, Page 1 of 18

Home Trends in Middletown, IN

Housing Trends

Median Sale Price
$190,000
Median Single Family Sale Price
$187,250
Average Price Per Sq Ft
$128
Number of Homes for Sale
10
Last 12 months Home Sales
70
Months of Supply
1.70
Median List Price
$199,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
0%
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