Middletown, MO Homes

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  $265,000

  • Land
  • 26.5 Acres
  • $10,000 per Acre

  0 Bales Rd (26 50+ - Acres), Middletown, MO 63359

  26.5+/- acres of scenic land with excellent homesite potential! This gently rolling property is located just 18 miles south of Bowling Green and 3 miles east of Middletown, Missouri. It features 21.5+/- tillable acres, abundant wildlife, and a small pond. Taxes are currently based on the original 81+/-acre parent tract. Additional acreage is also available. For additional information, please

  Bret Martin Bret Martin - Meyer & Company Real Estate

  0 Bales Rd (26 50+ - Acres), Middletown, MO 63359
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  $649,900 Last List Price Sold Jul 14, 2025

  8124 Highway K, Middletown, MO 63359

  • 3 Beds
  • 2 Baths
  • 2,241 Sq Ft
  • Built 2022

  Last Sold Summary

  • $290/SF
  • 3 Days On Market

  Last Listing Agent Cassandra Magruder Trophy Properties & Auction

  8124 Highway K, Middletown, MO 63359
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  Not Listed For Sale

  0 Audrain Road 689 (45+ - Acres), Middletown, MO 63359

  0 Audrain Road 689 (45+ - Acres), Middletown, MO 63359
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  $736,200

  • Land
  • 81.8 Acres
  • $9,000 per Acre

  0 Bales Rd (81 80+ Ac), Middletown, MO 63359

  This 81.8+/- acre property is located just east of Middletown, MO, offering approximately 70+/- acres of tillable land. The western border is lined by Sandy Creek, adding a scenic water feature to the property. Its a haven for wildlife, with numerous deer sightings. While there is some floodplain along the western and southern edges, the northeastern part of the property offers an excellent

  Meyer Auctions Meyer & Company Real Estate and Auctions

  0 Bales Rd (81 80+ Ac), Middletown, MO 63359
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  $20,000 Last List Price Sold May 01, 2025

  403 Missouri 161, Middletown, MO 63359

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  Last Sold Summary

  • $17/SF
  • 154 Days On Market

  Last Listing Agent Jessica Lawson Real Broker LLC

  403 Missouri 161, Middletown, MO 63359
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  /20

  Est $72,473 Not Listed For Sale

  • 1 Bed
  • 1 Bath

  629 Highway A, Middletown, MO 63359

  629 Highway A, Middletown, MO 63359
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  $497,700 Pending

  0 Bales Rd (55 3+ - Acres), Middletown, MO 63359

  55.3+/- acre parcel located just east of Middletown, MO, offering approximately 44+/- acres of tillable land. The western border is lined by Sandy Creek, adding a scenic water feature. Abundant deer activity is evident throughout the property. Includes some floodplain areas along the western and southern boundaries. Additional acreage options are available.

  Bret Martin Meyer & Company Real Estate

  0 Bales Rd (55 3+ - Acres), Middletown, MO 63359
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  $320,000 Last List Price Sold Nov 21, 2025

  0 Highway T Unit MIS25053724, Middletown, MO 63359

  • Built 2025

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Travis Owen Trophy Properties & Auction

  0 Highway T Unit MIS25053724, Middletown, MO 63359
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  Not Listed For Sale

  0 Highway K (79+ - Acres), Middletown, MO 63359

  0 Highway K (79+ - Acres), Middletown, MO 63359
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  /8

  $40,000

  • 4 Beds
  • 1 Bath
  • 1,938 Sq Ft

  301 Main St, Middletown, MO 63359

  Vintage 2-sty with large rooms. Beautiful wood staircase, most rooms have 10 inch wood trim. Upstairs rooms have 9 ft ceilings and 10 ft ceilings downstairs Needs work to restore it to original beauty. Large yard on 4 lots. Sold as-is.

  Jude Turner WJRJR LLC

  301 Main St, Middletown, MO 63359
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  /15

  $700,700 Last List Price Sold Oct 03, 2025

  77 Acres Highway Ac, Middletown, MO 63359

  • Land
  • 77 Acres
  • $9,100 per Acre

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Julie Worsham Milner Agency

  77 Acres Highway Ac, Middletown, MO 63359
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  /4

  Not Listed For Sale

  0 Mo-M Unit MAR24026690, Middletown, MO 63359

  0 Mo-M Unit MAR24026690, Middletown, MO 63359
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  /44

  $103,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  103 N Cherry N, Middletown, MO 63384

  Welcome to this beautiful country style farmhouse home. Postcard perfect !! This 3 bedroom 1 bath house boasts tall ceilings and old time country charm. Beautiful wood trim and stairway are true to the era of when this home was built. Picket white fence surrounds mature seasonal flowers and plants. Detached 2 car oversized garage with work room and half bath and an additional carport.

  Laura Wille Wille Real Estate LLC

  103 N Cherry N, Middletown, MO 63384
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  $70,000 Last List Price Sold Sep 04, 2025

  5139 Pike 427, Middletown, MO 63359

  • 3 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1880

  Last Sold Summary

  • $33/SF
  • 5 Days On Market

  Current Estimated Value $69,639

  Last Listing Agent Patrick Stumbaugh Stumbaugh Realty, LLC

  5139 Pike 427, Middletown, MO 63359
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  /13

  Not Listed For Sale

  • Studio

  0 Highway T Unit 23066330, Middletown, MO 63359

  0 Highway T Unit 23066330, Middletown, MO 63359
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  /24

  $265,000

  0 Bales Rd (26 5+ - Acres), Middletown, MO 63359

  26.5+/- acres of scenic land with excellent homesite potential! This gently rolling property is located just 18 miles south of Bowling Green and 3 miles east of Middletown, Missouri. It features 21.5+/- tillable acres, abundant wildlife, and a small pond. Taxes are currently based on the original 81+/-acre parent tract. Additional acreage is also available.

  Bret Martin Meyer & Company Real Estate

  0 Bales Rd (26 5+ - Acres), Middletown, MO 63359
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  $175,000 Last List Price Sold Jul 18, 2025

  56 Berger Rd, Middletown, MO 63359

  • 3 Beds
  • 1 Bath
  • 1,333 Sq Ft
  • Built 1983

  Last Sold Summary

  • $131/SF
  • 59 Days On Market

  Current Estimated Value $205,727

  Last Listing Agent Chelsey Van Horn Milner Agency

  56 Berger Rd, Middletown, MO 63359
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  /11

  Est $224,953 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,072 Sq Ft

  11393 Pike 410, Middletown, MO 63359

  11393 Pike 410, Middletown, MO 63359
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  /49

  $736,200 Pending

  0 Bales Rd (81 8+ - Acres), Middletown, MO 63359

  This 81.8+/- acre property is located just east of Middletown, MO, offering approximately 70+/- acres of tillable land. The western border is lined by Sandy Creek, adding a scenic water feature to the property. It’s a haven for wildlife, with numerous deer sightings. While there is some floodplain along the western and southern edges, the northeastern part of the property offers an excellent

  Bret Martin Meyer & Company Real Estate

  0 Bales Rd (81 8+ - Acres), Middletown, MO 63359
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  $379,900 Last List Price Sold Apr 01, 2025

  52 Berger Rd, Middletown, MO 63359

  • 4 Beds
  • 4 Baths
  • 1,836 Sq Ft
  • Built 1983

  Last Sold Summary

  • $207/SF
  • 15 Days On Market

  Current Estimated Value $354,162

  Last Listing Agent Chelsey Van Horn Milner Agency

  52 Berger Rd, Middletown, MO 63359
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  Not Listed For Sale

  0 Highway Bb (10+ - Acres), Middletown, MO 63359

  0 Highway Bb (10+ - Acres), Middletown, MO 63359
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  /51

  $414,999 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,441 Sq Ft

  27057 Pike 434, Middletown, MO 63359

  Enjoy peaceful country living just minutes from town in rural Pike County. This 4-bedroom, 2.5-bath home offers over 2,400 sq ft of living space on 8 unrestricted acres with a mix of pasture and scattered trees. The open floor plan features a custom country kitchen, separate dining area, newer flooring throughout, hardwood accents, and a full masonry gas fireplace. Three bedrooms and spacious

  Tabitha White Inspiring Real Estate

  27057 Pike 434, Middletown, MO 63359
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  $470,000 Last List Price Sold Nov 07, 2025

  89 Kern Rd, Middletown, MO 63359

  • Built 1975

  Last Sold Summary

  • 189 Days On Market

  Current Estimated Value $432,600

  Last Listing Agent Jason Cleveland Trophy Properties & Auction

  89 Kern Rd, Middletown, MO 63359
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  Not Listed For Sale

  • Studio

  0 Pike Co Rd 340 (75+ - Acres), Middletown, MO 63359

  0 Pike Co Rd 340 (75+ - Acres), Middletown, MO 63359
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  $545,000 Last List Price Sold Apr 11, 2025

  13840 Highway Pp, Middletown, MO 63359

  • Land
  • 46 Acres
  • $11,848 per Acre

  Last Sold Summary

  • 43 Days On Market

  Current Estimated Value $515,138

  Last Listing Agent Tyler Wilmsmeyer Sports Afield Real Estate

  13840 Highway Pp, Middletown, MO 63359
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,703 Sq Ft

  96 Evergreen Rd, Middletown, MO 63359

  96 Evergreen Rd, Middletown, MO 63359
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  $255,000 Last List Price Sold Oct 02, 2025

  42 Berger Rd, Middletown, MO 63359

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 2001

  Last Sold Summary

  • $170/SF
  • 142 Days On Market

  Current Estimated Value $268,563

  Last Listing Agent Chelsey Van Horn Milner Agency

  42 Berger Rd, Middletown, MO 63359
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  /93

  Est $351,491 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft

  30 Angel Ln, Middletown, MO 63359

  30 Angel Ln, Middletown, MO 63359
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  $325,000 Last List Price Sold May 05, 2025

  26969 Highway M, Middletown, MO 63359

  • Land
  • 9.51 Acres
  • $34,185 per Acre

  Last Sold Summary

  • 149 Days On Market

  Current Estimated Value $286,420

  Last Listing Agent Travis Owen Trophy Properties & Auction

  26969 Highway M, Middletown, MO 63359
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  Est $181,898 Not Listed For Sale

  • 2 Beds
  • 1 Bath

  59 Pond Bottom Rd, Middletown, MO 63359

  59 Pond Bottom Rd, Middletown, MO 63359
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  /10

  $350,000 Last List Price Sold Jan 23, 2026

  00 Highway T, Middletown, MO 63359

  • Built 2025

  Last Sold Summary

  • 87 Days On Market

  Last Listing Agent Travis Owen Trophy Properties & Auction

  00 Highway T, Middletown, MO 63359
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  /14

  Not Listed For Sale

  • Studio

  32 Whit Sydnor Rd, Middletown, MO 63359

  32 Whit Sydnor Rd, Middletown, MO 63359
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  /43

  $85,000 Last List Price Sold Aug 15, 2025

  610 N Caldwell St, Middletown, MO 63359

  • 4 Beds
  • 2.5 Baths
  • 2,052 Sq Ft
  • Built 1997

  Last Sold Summary

  • $41/SF
  • 327 Days On Market

  Current Estimated Value $44,745

  Last Listing Agent Chelsey Van Horn Milner Agency

  610 N Caldwell St, Middletown, MO 63359
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  /18

  Not Listed For Sale

  • 2 Beds
  • 1 Bath

  1963 Highway E, Middletown, MO 63359

  1963 Highway E, Middletown, MO 63359
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  /22

  $369,000 Last List Price Sold Sep 26, 2025

  0 Flint Rd (41+ - Ac) Unit MAR25028459, Middletown, MO 63359

  Last Sold Summary

  • 99 Days On Market

  Last Listing Agent Danielle Ryker Blondin Group, Inc

  0 Flint Rd (41+ - Ac) Unit MAR25028459, Middletown, MO 63359
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  /18

  Est $252,728 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,261 Sq Ft

  5182 Pike 427, Middletown, MO 63359

  5182 Pike 427, Middletown, MO 63359
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  $291,200 Last List Price Sold Feb 19, 2026

  36 +/- Acres Hwy Mm, Middletown, MO 63359

  • Built 1701

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Phil Reid Westbound Real Estate LLC

  36 +/- Acres Hwy Mm, Middletown, MO 63359
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  Est $271,156 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,446 Sq Ft

  33 Main St, Middletown, MO 63359

  33 Main St, Middletown, MO 63359
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  $410,900 Last List Price Sold Jul 17, 2025

  24496 Pike 439, Middletown, MO 63359

  • 3 Beds
  • 2.5 Baths
  • 2,550 Sq Ft
  • Built 2015

  Last Sold Summary

  • $161/SF
  • 281 Days On Market

  Current Estimated Value $391,809

  Last Listing Agent Angela Peters Century 21 Broughton Team

  24496 Pike 439, Middletown, MO 63359
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  /42

  Est $140,104 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  111 N Caldwell St, Middletown, MO 63359

  111 N Caldwell St, Middletown, MO 63359

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