Montgomery, MO Homes

• 

  

  

  /47

  $500,500

  89 Kern Rd, Middletown, MO 63359

  Escape to this stunning 77± acre property just 2.7 miles from Middletown, MO. This gently rolling, hilly land features scattered timber and wooded areas, perfect for outdoor enthusiasts and hunters alike. With existing trails and access to electric and county water, it's ideal for a hunting cabin or full-time residence. This family-owned land, rich in history, is ready for its next chapter.

  Jason Cleveland Trophy Properties & Auction

  89 Kern Rd, Middletown, MO 63359
• 

  

  

  /53

  $175,000 Last List Price Sold Jul 18, 2025

  • 1,333 Sq Ft
  • $131/SF
  • 59 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1983

  56 Berger Rd, Middletown, MO 63359

  Rural home on 9.9 +/- acres! A nice mixed of open and wooded land ready for you. Perfect for horses, cattle, other livestock. Four-wheeler trails winding back to the back of the property, wet creek, great hunting with lots of wildlife roaming through the area. 3 bedroom, 1 bath earth contact home. Metal roof & siding installed in 2019, as well as new bathtub, toilet. Galley kitchen with new

  Chelsey Van Horn Milner Agency

  56 Berger Rd, Middletown, MO 63359
• 

  

  

  /14

  Not Listed For Sale

  • Studio

  32 Whit Sydnor Rd, Middletown, MO 63359

  32 Whit Sydnor Rd, Middletown, MO 63359
• 

  

  

  /23

  $265,000

  • Land
  • 26 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
• 

  

  

  /45

  $410,900 Last List Price Sold Jul 17, 2025

  • 2,550 Sq Ft
  • $161/SF
  • 281 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2015

  24496 Pike 439, Middletown, MO 63359

  Nestled on 15 picturesque acres, this charming 1.5-story cabin offers serene lakeside living with a stocked 5-acre lake right at your doorstep. The cabin features 3 spacious bedrooms, 2.5 bathrooms, and is beautifully appointed with custom hickory cabinets throughout. Enjoy the convenience of an in-home elevator, providing easy access to all levels.Step outside to relax on the expansive

  Angela Peters Century 21 Broughton Team

  24496 Pike 439, Middletown, MO 63359
• 

  

  /4

  Not Listed For Sale

  0 Mo-M Unit MAR24026690, Middletown, MO 63359

  0 Mo-M Unit MAR24026690, Middletown, MO 63359
• 

  

  /49

  $736,200

  • Land
  • 82 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
• 

  

  /69

  $649,900 Last List Price Sold Jul 14, 2025

  • 2,241 Sq Ft
  • $290/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2022

  8124 Highway K, Middletown, MO 63359

  Nestled on approximately 5± unrestricted acres, this 3-bed, 2-bath home spans 2,200 sq ft and was built in 2022, seamlessly combining modern amenities with timeless craftsmanship. The thoughtfully designed interior features high-quality finishes, including a dream kitchen with a spacious pantry, black stainless steel KitchenAid appliances, Amish-built custom cabinets, and gorgeous granite

  Cassandra Magruder Trophy Properties & Auction

  8124 Highway K, Middletown, MO 63359
• 

  

  /13

  Not Listed For Sale

  • Studio

  0 Highway T Unit 23066330, Middletown, MO 63359

  0 Highway T Unit 23066330, Middletown, MO 63359
• 

  

  /43

  $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
• 

  

  /38

  $325,000 Last List Price Sold May 05, 2025

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

  • 149 Days On Market

  26969 Highway M, Middletown, MO 63359

  This Pike county homestead is a 9.503-acre estate at the junction of Hwy M and Hwy K. With ample space for livestock or gardening, the property features a hayed field, fruit trees, and several outbuildings. The 3-bed, 1.5-bath home, built in 1966 and expanded in 1990, is in great shape with a well-kept basement and a new roof (2023). A 30x50 pole barn, workshops, and sheds offer plenty of

  Travis Owen High Point Land Company, LLC

  26969 Highway M, Middletown, MO 63359
• 

  

  /11

  Est $87,184 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,072 Sq Ft

  11393 Pike 410, Middletown, MO 63359

  11393 Pike 410, Middletown, MO 63359
• 

  

  /18

  $70,000

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

  5139 Pike 427, Middletown, MO 63359

  Hidden Gem Alert!! Secluded Fixer-Upper on a Sprawling 1-acre Oasis!Escape the hustle and unleash your inner visionary with thisone-of-a-kind fixer-upper, tucked away on a lush, private 1-acreretreat! Surrounded by towering trees and whispering breezes, thisdiamond in the rough is begging for your creative touch to transformit into the home of your dreams- or a

  Patrick Stumbaugh Stumbaugh Realty, LLC

  5139 Pike 427, Middletown, MO 63359
• 

  /2

  $20,000 Last List Price Sold May 01, 2025

  • 1,200 Sq Ft
  • $17/SF
  • 154 Days On Market

  • 3 Beds
  • 1 Bath

  403 Missouri 161, Middletown, MO 63359

  Investor special! While this property requires significant attention, the possibilities are endless for those with a vision and a keen eye for transformation. This is a great opportunity to create a personalized space or add to your investment portfolio. This sale includes 2 lots totaling 0.74 +/- acre. Being sold in AS-IS condition and will include any personal property left at the residence.

  Jessica Lawson Real Broker LLC

  403 Missouri 161, Middletown, MO 63359
• 

  

  /26

  Not Listed For Sale

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

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

  

  /15

  $700,700

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

  77 Acres Highway Ac, Middletown, MO 63359

  This beautiful plot of rolling land would be beautiful with your new home sitting on it. Layout of the land would be perfect for a walkout basement that overlooks your crops. 72 Acres are now leased for farming. There is a well on the 40 acre peice that was from the previous farmhouse. Black top frontage with a county road splitting the property. Seller will divide property, see listing

  Julie Worsham Milner Agency

  77 Acres Highway Ac, Middletown, MO 63359
• 

  

  /33

  $545,000 Last List Price Sold Apr 11, 2025

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

  • 43 Days On Market

  13840 Highway Pp, Middletown, MO 63359

  This country home on 46+/- acres in Pike County, MO is the perfect mix of space, privacy, and country living. With over 2,300 sq. ft., it features 2 bedrooms, 1 bath, and a bonus room in the basement that could make a non-conventional bedroom. Out back, there’s a large two-car garage with power and a separate shop for extra storage or workspace.The property includes 20+/- tillable acres, ideal

  Tyler Wilmsmeyer Sports Afield Real Estate

  13840 Highway Pp, Middletown, MO 63359
• 

  

  /51

  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
• 

  

  /22

  $369,000

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

  Versatile 41-acre property in Montgomery County, MO, featuring 27 acres of productive tillable ground and the balance in mature timber. With mostly level terrain and county road frontage on two sides, it’s ideal for farming, recreation, or investment. Enjoy income potential and excellent hunting or outdoor opportunities. Located just 20 minutes from I-70 and under an hour from Wentzville, this

  Danielle Ryker Blondin Group, Inc

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

  

  /53

  $379,900 Last List Price Sold Apr 01, 2025

  • 1,836 Sq Ft
  • $207/SF
  • 15 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1983

  52 Berger Rd, Middletown, MO 63359

  Newer construction with lots of space for a family! All on 6.76+/- acres with no restrictions. This incredible home offers 4 main level bedrooms with 3 full baths. Large primary bedroom suite with back deck access and 12x12 primary closet with full bath attached. Jack & Jill bathroom shared between 2 of the 3 other bedrooms. Main floor laundry just off the dining room. Spacious kitchen offering

  Chelsey Van Horn Milner Agency

  52 Berger Rd, Middletown, MO 63359
• 

  

  /24

  Not Listed For Sale

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

  96 Evergreen Rd, Middletown, MO 63359

  96 Evergreen Rd, Middletown, MO 63359
• 

  

  /49

  $260,000

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

  42 Berger Rd, Middletown, MO 63359

  One owner home with excellent maintenance kept! This earth contact home offers 3 bedrooms, 2 full baths. Beautiful 50x8 front, covered porch with view of the yard and surrounding woods. Very private, wet creek, walking/ four-wheeler trail that takes you to the back property line. Open floor concept with kitchen/dining combo. TONS of custom oak cabinetry with lifetime warranty, large pantry. All

  Chelsey Van Horn Milner Agency

  42 Berger Rd, Middletown, MO 63359
• 

  

  /35

  $269,000 Last List Price Sold Nov 01, 2024

  • Land
  • 45 Acres
  • $5,978 per Acre

  • 3 Days On Market

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

  Discover this exceptional 45+/- acre property located on Audrain Road 689, just outside of Middletown, Missouri. Perfect for hunting enthusiasts and nature lovers, this affordable parcel offers a diverse landscape with a balanced mix of open fields and wooded areas. The Cuivre River winds through the property, providing a natural habitat for wildlife, enhancing the property's appeal for hunting

  Rick Meyer Meyer & Company Real Estate

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

  

  /26

  Est $172,464 Not Listed For Sale

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

  33 Main St, Middletown, MO 63359

  33 Main St, Middletown, MO 63359
• 

  

  /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
• 

  

  /20

  $79,900 Last List Price Sold Oct 01, 2024

  • Land

  • 65 Days On Market

  629 Highway A, Middletown, MO 63359

  5 acre nice little retreat approx. half woods and half open great homesite or weekend getaway with a 48' x 93' older pole barn with concrete floor and small living quarters that needs some TLC, county water connected to the building also has a deep well. electric and plumbing in the building. Property has camper connections.

  Jackie Brower Milner Agency

  629 Highway A, Middletown, MO 63359
• 

  

  /42

  Est $137,090 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
• 

  

  /7

  $372,000

  40, Middletown, MO 63359

  This rolling piece of land would work perfect for your new home. The land slopes to make it perfect for a walkout basement. Black top frontage on West side and gravel on East and South Side. Privacy is all around you! Peaceful and Quiet and Beautiful Sunsets. Land is being farmed and the new buyer will receive amount from lease in fall. Call for more information on who's farming it

  Julie Worsham Milner Agency

  40, Middletown, MO 63359
• 

  

  /45

  $671,500 Last List Price Sold Sep 06, 2024

  • Land
  • 79 Acres
  • $8,500 per Acre

  • 44 Days On Market

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

  Imagine your dream escape on this extraordinary 79+/- acre property. The property includes tillable acres, lush mature timber, wooded draws, good home sites and an excellent potential pond site, making it the perfect location for your rural retreat. A hunter's paradise, this property boasts a rich history of successful hunts. With 46+/- tillable acres, you have ideal space for food plots or row

  Bret Martin Meyer & Company Real Estate

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

  

  /30

  Est $171,723 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,209 Sq Ft

  27006 Pike 413, Middletown, MO 63359

  27006 Pike 413, Middletown, MO 63359
• 

  

  /43

  $85,000 Pending

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

  610 N Caldwell St, Middletown, MO 63359

  4 bedroom, 2.5 bath manufactured home on the edge of town! Quiet street. Attached, oversized carport for multiple vehicles, circle driveway. Large primary bedroom with separate vanities prior to entering the primary bath with stand-in shower and tub. Most all faucets have been updated as well. Comfortable kitchen with plenty of cabinets and countertops. All kitchen appliances convey. Fridge and

  Chelsey Van Horn Milner Agency

  610 N Caldwell St, Middletown, MO 63359
• 

  

  /93

  Est $321,835 Not Listed For Sale

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

  30 Angel Ln, Middletown, MO 63359

  30 Angel Ln, Middletown, MO 63359
• 

  

  /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
• 

  

  /41

  Est $232,794 Not Listed For Sale

  • 2 Beds
  • 1 Bath

  59 Pond Bottom Rd, Middletown, MO 63359

  59 Pond Bottom Rd, Middletown, MO 63359
• 

  

  /18

  Not Listed For Sale

  • 2 Beds
  • 1 Bath

  1963 Highway E, Middletown, MO 63359

  1963 Highway E, Middletown, MO 63359
• 

  

  /18

  Est $132,086 Not Listed For Sale

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

  5182 Pike 427, Middletown, MO 63359

  5182 Pike 427, Middletown, MO 63359
• 

  

  /24

  Not Listed For Sale

  • Studio

  Unlisted Address

  Unlisted Address
• 

  

  /11

  Est $59,681 Not Listed For Sale

  • Studio
  • 2,016 Sq Ft

  602 N Cherry St, Middletown, MO 63359

  602 N Cherry St, Middletown, MO 63359
• 

  

  /3

  Not Listed For Sale

  7 Missouri 161, Middletown, MO 63359

  7 Missouri 161, Middletown, MO 63359
• 

  

  /31

  Est $94,470 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft

  218 Johnson, Middletown, MO 63359

  218 Johnson, Middletown, MO 63359

Showing Results 1 - 40, Page 1 of 13