Chester, MT Homes

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  $795,000

  • 8,516 Sq Ft

  518 W Jefferson Ave, Chester, MT 59522

  Excellent investment opportunity! This well-maintained 10-plex features 8 units with 2 bedrooms and 1.5 baths, plus 2 units with 1 bedroom and 1.5 baths. Each unit offers functional layouts and comfortable living spaces, making them highly desirable for tenants. The property boasts strong financials, consistent income, and a proven track record of occupancy. Perfect for investors looking for a

  Seth Haak Keller Williams Northern MT

  518 W Jefferson Ave, Chester, MT 59522
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  /13

  $75,000 Last List Price Sold Jun 20, 2025

  509 E Washington Ave, Chester, MT 59522

  • Land
  • 0.48 Acre
  • $155,602 per Acre

  Last Sold Summary

  • 36 Days On Market

  Current Estimated Value $120,153

  Last Listing Agent Derek Fraser Backroad Realty Inc.

  509 E Washington Ave, Chester, MT 59522
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  /19

  Est $152,697 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  19 W Jefferson Ave, Chester, MT 59522

  19 W Jefferson Ave, Chester, MT 59522
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  /24

  $345,000

  • 4 Beds
  • 3 Baths
  • 3,840 Sq Ft

  522 Weldy St, Chester, MT 59522

  Welcome to the last best place, Chester, MT. Nearly 2 acres of country living in city limits is FOR SALE! This 4 bedroom, 3 bathroom home was built in 2010 and spans over 3,840 square feet. It includes an attached 2 car garage, main floor laundry, conveniently located right in from the garage, and underground sprinklers. The main floor has 3 spacious bedrooms, 2 bathrooms, and master

  Derek Fraser Backroad Realty Inc.

  522 Weldy St, Chester, MT 59522
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  /2

  $375,000 Last List Price Sold Jan 09, 2026

  2699 Whitlash Rd, Chester, MT 59522

  • 1 Bed
  • 1 Bath
  • 840 Sq Ft
  • Built 1916

  Last Sold Summary

  • $446/SF
  • 7 Days On Market

  Last Listing Agent Jacob Dickinson Bootlegger Realty, LLP

  2699 Whitlash Rd, Chester, MT 59522
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  /40

  Est $255,710 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,784 Sq Ft

  534 W Monroe Ave, Chester, MT 59522

  534 W Monroe Ave, Chester, MT 59522
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  /20

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,992 Sq Ft

  127 Main St, Chester, MT 59522

  Welcome to this beautifully updated 2-bed, 2-bath home right on Main Street in Chester, Montana! With its bright open floor plan and modern LVT flooring, the space feels fresh, inviting, and easy to love. The primary suite is a true retreat, featuring a relaxing jetted tub, while the second bedroom and full bath offer great flexibility. Enjoy a detached two-stall garage for all your gear and

  Trampus Corder Corder and Associates, LLC

  127 Main St, Chester, MT 59522
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  /2

  $249,000 Last List Price Sold Dec 16, 2025

  510 2nd St W, Chester, MT 59522

  • 5 Beds
  • 3 Baths
  • 3,504 Sq Ft
  • Built 1965

  Last Sold Summary

  • $71/SF
  • 56 Days On Market

  Last Listing Agent Derek Fraser Backroad Realty Inc.

  510 2nd St W, Chester, MT 59522
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  /6

  Est $174,802 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,808 Sq Ft

  525 W Jefferson Ave, Chester, MT 59522

  525 W Jefferson Ave, Chester, MT 59522
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  /3

  $37,500 Under Contract

  • Land
  • 0.19 Acre
  • $194,301 per Acre

  147 W Quincy Ave, Chester, MT 59522

  Two spacious lots located on the heart of the Hi-Line in Chester, Montana for sale. This is a great location just two blocks from CJI Public Schools and two blocks from Logan Health Clinic & Nursing Home. There is currently a house that needs to be tore down at buyer's expense. This property includes a 25' x 32' garage that, with some work, would make a nice storage garage. The utilities on the

  Derek Fraser Backroad Realty Inc.

  147 W Quincy Ave, Chester, MT 59522
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  /2

  $229,000 Last List Price Sold Dec 10, 2025

  418 NE Weldy St, Chester, MT 59522

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1958

  Last Sold Summary

  • $164/SF
  • 2 Days On Market

  Last Listing Agent Derek Fraser Backroad Realty Inc.

  418 NE Weldy St, Chester, MT 59522
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  /2

  Not Listed For Sale

  NHN Hill School Rd, Chester, MT 59522

  NHN Hill School Rd, Chester, MT 59522
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  /30

  $595,000

  • Land
  • 1.03 Acres
  • $577,670 per Acre

  510 Washington Ave, Chester, MT 59522

  This incredible commercial 1.03 Acre property offers a rare opportunity in Chester, MT! Situated along the high-traffic Hwy 2 corridor, property includes 13 city lots, with an existing 5,040 sq. ft. building, spanning across 3 of those lots. With room for future expansion or additional development, this property provides significant potential for growth. The existing building has a flexible

  Alisha Koch Glacier Sotheby's International Realty Bigfork

  510 Washington Ave, Chester, MT 59522
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  /2

  $47,000 Last List Price Sold Aug 25, 2025

  18.5 & 22 W Jefferson Ave, Chester, MT 59522

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1971

  Last Sold Summary

  • $61/SF
  • 6 Days On Market

  Last Listing Agent Derek Fraser Backroad Realty Inc.

  18.5 & 22 W Jefferson Ave, Chester, MT 59522
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  /2

  Est $750,394 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,500 Sq Ft

  735 Hill School Rd, Chester, MT 59522

  735 Hill School Rd, Chester, MT 59522
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  /8

  $50,000

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  11 Main St, Chester, MT 59522

  Investment opportunity available with this cozy 792 sq ft, 2-bedroom, 1-bathroom home, perfectly situated on a manageable 4,060 sq ft lot in town. This could be a great rental investment with a little TLC, you can unlock its full functionality. The home boasts easy access to local amenities, making it convenient for tenants or first-time homeowners. The small lot ensures low maintenance, allowing

  Jacob Dickinson Bootlegger Realty, LLP

  11 Main St, Chester, MT 59522
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  /2

  $210,000 Last List Price Sold Jan 07, 2026

  123 W Jefferson Ave, Chester, MT 59522

  • 5 Beds
  • 2 Baths
  • 1,775 Sq Ft
  • Built 1905

  Last Sold Summary

  • $118/SF
  • 242 Days On Market

  Last Listing Agent John Ditore Live in Montana Real Estate

  123 W Jefferson Ave, Chester, MT 59522
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  /16

  Not Listed For Sale

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

  407 Jackson Ave, Chester, MT 59522

  407 Jackson Ave, Chester, MT 59522
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  /13

  $169,000

  • 1 Bed
  • 1 Bath
  • 1,800 Sq Ft

  318 W Jackson Ave, Chester, MT 59522

  This "Shouse" is for sale! This shop/house is 1800 total sq. ft with no to low maintenance inside and out. It has 900 sq. ft. living area that is a one bedroom, one bathroom home. The shop is 900 sq. ft. with a 10'x20' garage door. This property is the perfect property for one level living folks, single living folks, a rental, or even air bnb. It is located two blocks from the hospital and three

  Derek Fraser Backroad Realty Inc.

  318 W Jackson Ave, Chester, MT 59522
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  /2

  $78,000 Last List Price Sold Jul 30, 2025

  18 W Quincy Ave, Chester, MT 59522

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1971

  Last Sold Summary

  • $74/SF
  • 43 Days On Market

  Last Listing Agent Derek Fraser Backroad Realty Inc.

  18 W Quincy Ave, Chester, MT 59522
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  /15

  Est $143,452 Not Listed For Sale

  • 1 Bed
  • 2 Baths
  • 1,326 Sq Ft

  323 W Monroe Ave, Chester, MT 59522

  323 W Monroe Ave, Chester, MT 59522
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  /30

  $146,500

  • 2 Beds
  • 1 Bath
  • 1,325 Sq Ft

  310 3rd St E, Chester, MT 59522

  Tucked behind fragrant lilac bushes and mature caraganas that offer natural privacy, a charming Chester cottage awaits new ownership. In addition to comfort, the 2-bedroom 1 bathroom home has thoughtful details such as arched entryways. The kitchen features new appliances. Discover the detached double car garage is heated, an invaluable luxury during Montana winters. The home is situated on a

  Trampus Corder Corder and Associates LLC

  310 3rd St E, Chester, MT 59522
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  /20

  $187,000 Last List Price Sold May 29, 2025

  418 W Adams Ave, Chester, MT 59522

  • 3 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 1955

  Last Sold Summary

  • $96/SF
  • 113 Days On Market

  Current Estimated Value $179,168

  Last Listing Agent Jacob Dickinson Bootlegger Realty, LLP

  418 W Adams Ave, Chester, MT 59522
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  /5

  Not Listed For Sale

  680 acres 1700 Rd E, Chester, MT 59522

  680 acres 1700 Rd E, Chester, MT 59522
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  /2

  $235,000 Last List Price Sold Aug 26, 2025

  45 W Monroe Ave, Chester, MT 59522

  • 3 Beds
  • 1 Bath
  • 1,098 Sq Ft
  • Built 1952

  Last Sold Summary

  • $214/SF
  • 102 Days On Market

  Current Estimated Value $198,023

  Last Listing Agent Derek Fraser Backroad Realty Inc.

  45 W Monroe Ave, Chester, MT 59522
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  /27

  Est $155,954 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  326 Main St, Chester, MT 59522

  326 Main St, Chester, MT 59522
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  /46

  $185,000 Last List Price Sold May 27, 2025

  323 2nd St E, Chester, MT 59522

  • 5 Beds
  • 2 Baths
  • 2,960 Sq Ft
  • Built 1920

  Last Sold Summary

  • $62/SF
  • 242 Days On Market

  Current Estimated Value $202,783

  Last Listing Agent Derek Fraser Backroad Realty Inc.

  323 2nd St E, Chester, MT 59522
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  /2

  Est $128,013 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  226 1st St E, Chester, MT 59522

  226 1st St E, Chester, MT 59522
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  /2

  $68,000 Last List Price Sold Oct 06, 2025

  114 1st St E, Chester, MT 59522

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • Built 1975

  Last Sold Summary

  • $69/SF
  • 56 Days On Market

  Last Listing Agent Kaitlyn Lyders Corder and Associates LLC

  114 1st St E, Chester, MT 59522
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  /29

  Est $265,662 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,428 Sq Ft

  410 3rd St W, Chester, MT 59522

  410 3rd St W, Chester, MT 59522
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  /2

  $299,000 Last List Price Sold Sep 23, 2025

  130 W Quincy Ave, Chester, MT 59522

  • 7 Beds
  • 4.5 Baths
  • 4,236 Sq Ft
  • Built 1949

  Last Sold Summary

  • $71/SF
  • 40 Days On Market

  Current Estimated Value $319,379

  Last Listing Agent Derek Fraser Backroad Realty Inc.

  130 W Quincy Ave, Chester, MT 59522
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  /22

  Est $339,961 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 2,486 Sq Ft

  000 Tbd, Chester, MT 59522

  000 Tbd, Chester, MT 59522
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  $210,000 Last List Price Sold Oct 01, 2025

  414 2nd St W, Chester, MT 59522

  • 5 Beds
  • 3 Baths
  • 2,356 Sq Ft
  • Built 1968

  Last Sold Summary

  • $89/SF
  • 294 Days On Market

  Current Estimated Value $191,322

  Last Listing Agent Trampus Corder Corder & Associates

  414 2nd St W, Chester, MT 59522
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  /12

  Est $213,187 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,432 Sq Ft

  10 W Quincy Ave, Chester, MT 59522

  10 W Quincy Ave, Chester, MT 59522
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  /9

  Est $142,639 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,680 Sq Ft

  234 W Monroe Ave, Chester, MT 59522

  234 W Monroe Ave, Chester, MT 59522
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  /49

  Est $278,317 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,444 Sq Ft

  3939 Mt Highway 223, Chester, MT 59522

  3939 Mt Highway 223, Chester, MT 59522
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  /2

  Est $126,000 Not Listed For Sale

  16 W Jefferson Ave, Chester, MT 59522

  16 W Jefferson Ave, Chester, MT 59522
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  /2

  Not Listed For Sale

  Nhn W Monroe Ave, Chester, MT 59522

  Nhn W Monroe Ave, Chester, MT 59522
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  /2

  Not Listed For Sale

  • Studio
  • 3,927 Sq Ft

  113 E Washington Ave, Chester, MT 59522

  113 E Washington Ave, Chester, MT 59522
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  /2

  Not Listed For Sale

  • Studio
  • 3,180 Sq Ft

  10 1st St E, Chester, MT 59522

  10 1st St E, Chester, MT 59522

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