11

Middletown, IN Homes for Sale under $100,000

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  • 27 Crestwood Dr Unit 92, Middletown, IN 47356
    27 Crestwood Dr Unit 92, Middletown, IN 47356
    27 Crestwood Dr Unit 92, Middletown, IN 47356
    /9

    $77,999

    • 3 Beds
    • 2 Baths

    27 Crestwood Dr Unit 92, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR SIZZLING SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent and NO application fees. Offer expires June 30, 2026. Act fast! Restrictions apply. Welcome to this thoughtfully upgraded home located in the heart of Crestwood on a corner lot! LThe 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
  • 27 Crestwood Dr Unit 84, Middletown, IN 47356
    27 Crestwood Dr Unit 84, Middletown, IN 47356
    27 Crestwood Dr Unit 84, Middletown, IN 47356
    /10

    $78,999

    • 3 Beds
    • 2 Baths

    27 Crestwood Dr Unit 84, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR SIZZLING SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent and NO application fees. Offer expires June 30, 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

    Kameron Allen Crestwood

    27 Crestwood Dr Unit 84, Middletown, IN 47356
  • 27 Crestwood Dr Unit 31, Middletown, IN 47356
    27 Crestwood Dr Unit 31, Middletown, IN 47356
    27 Crestwood Dr Unit 31, Middletown, IN 47356
    /26

    $92,999

    • 3 Beds
    • 2 Baths

    27 Crestwood Dr Unit 31, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR SIZZLING SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent and NO application fees. Offer expires June 30, 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
  • 804 High St, Middletown, IN 47356
    804 High St, Middletown, IN 47356
    804 High St, Middletown, IN 47356
    /7

    $75,499

    $17K PRICE DROP
    • 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
  • 27 Crestwood Dr Unit 15, Middletown, IN 47356
    27 Crestwood Dr Unit 15, Middletown, IN 47356
    27 Crestwood Dr Unit 15, Middletown, IN 47356
    /10

    $77,999

    • 3 Beds
    • 2 Baths

    27 Crestwood Dr Unit 15, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR SIZZLING SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent and NO application fees. Offer expires June 30, 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
  • 27 Crestwood Dr Unit 94, Middletown, IN 47356
    27 Crestwood Dr Unit 94, Middletown, IN 47356
    27 Crestwood Dr Unit 94, Middletown, IN 47356
    /9

    $69,999

    • 3 Beds
    • 2 Baths

    27 Crestwood Dr Unit 94, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR SIZZLING SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent and NO application fees. Offer expires June 30, 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
  • 27 Crestwood Dr Unit 86, Middletown, IN 47356
    27 Crestwood Dr Unit 86, Middletown, IN 47356
    27 Crestwood Dr Unit 86, Middletown, IN 47356
    /11

    $77,999

    • 3 Beds
    • 2 Baths

    27 Crestwood Dr Unit 86, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR SIZZLING SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent and NO application fees. Offer expires June 30, 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 86, Middletown, IN 47356
  • 27 Crestwood Dr Unit 98, Middletown, IN 47356
    27 Crestwood Dr Unit 98, Middletown, IN 47356
    27 Crestwood Dr Unit 98, Middletown, IN 47356
    /10

    $68,999

    • 3 Beds
    • 2 Baths

    27 Crestwood Dr Unit 98, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR SIZZLING SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent and NO application fees. Offer expires June 30, 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
  • 27 Crestwood Dr Unit 116, Middletown, IN 47356
    27 Crestwood Dr Unit 116, Middletown, IN 47356
    27 Crestwood Dr Unit 116, Middletown, IN 47356
    /30

    $69,999

    • 3 Beds
    • 2 Baths

    27 Crestwood Dr Unit 116, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR SIZZLING SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent and NO application fees. Offer expires June 30, 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

    Kameron Allen Crestwood

    27 Crestwood Dr Unit 116, Middletown, IN 47356
  • 6671 N County Road 525 W, Middletown, IN 47356
    6671 N County Road 525 W, Middletown, IN 47356
    6671 N County Road 525 W, Middletown, IN 47356
    /14

    $72,300

    $68K PRICE DROP
    • 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
  • 27 Crestwood Dr Unit 80, Middletown, IN 47356
    27 Crestwood Dr Unit 80, Middletown, IN 47356
    27 Crestwood Dr Unit 80, Middletown, IN 47356
    /11

    $68,999

    • 3 Beds
    • 2 Baths

    27 Crestwood Dr Unit 80, Middletown, IN 47356

    TAKE ADVANTAGE OF OUR SIZZLING SUMMER SAVINGS EVENT! If you purchase this home, receive 4 months FREE site rent and NO application fees. Offer expires June 30, 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 80, Middletown, IN 47356
Indiana Henry County Middletown

Real Estate & Homes in Middletown, IN under $100,000

Home Prices in Middletown, IN

The median home sale price in Middletown, IN is $190,000, down 3% year-over-year. Homes in Middletown sell in 32 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$190,000
Median Single Family Sale Price
$191,500
Median 2 Bedroom Sale Price
$164,000
Median 1 Bedroom Sale Price
$94,250
Average Price Per Sq Ft
$133
Number of Homes for Sale
13
Last 12 months Home Sales
69
Months of Supply
2.30
Median List Price
$199,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-3%
How to Buy a Home How to Finance a Home How to Sell a Home

In Middletown, there are currently 11 homes for sale priced under $100,000, providing budget-friendly options for prospective buyers. Whether you're in search of houses for sale under 100k or other property types, there are opportunities to discover your ideal home within your budget in Middletown, IN. From cozy starter homes to properties awaiting your personal touch, these affordable residences offer an entry point into the housing market or an opportunity for real estate investment without stretching your finances.

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