Homes in ZIP Code 65588

• 

  

  

  /5

  $49,900 Pending

  • Land
  • 12.91 Acres
  • $3,865 per Acre

  000 Briar Ridge Ln, Winona, MO 65588

  This is the Missouri hunting property everyone wants but rarely finds! Gated, private, and sharing a boundary with Mark Twain National Forest, this 12.91-acre tract gives you walk-in access to thousands of acres of prime public land right from your back door. Loaded with mature hardwoods, strong whitetail movement, existing stands, and cleared shooting lanes, it's a true turn-key setup for the

  Bob McBride United Country Missouri Ozarks Realty Inc.

  

  000 Briar Ridge Ln, Winona, MO 65588
• 

  

  

  /27

  $194,300 Last List Price Sold Aug 22, 2025

  2955 County Road 156, Winona, MO 65588

  • 3 Beds
  • 2 Baths
  • 2,499 Sq Ft
  • Built 1989

  Last Sold Summary

  • $78/SF
  • 59 Days On Market

  Current Estimated Value $233,976

  Last Listing Agent Linda Francis Mossy Oak Properties Mozark Land and Farm

  

  2955 County Road 156, Winona, MO 65588
• 

  

  

  /23

  Est $236,820 Not Listed For Sale

  17861 State Highway F, Eminence, MO 65588

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1957

  17861 State Highway F, Eminence, MO 65588

  Last Sold Summary

  • $0/SF
  • 75 Days On Market

  Last Listing Agent steve willard Ozark Land Exchange
• 

  

  

  /62

  $1,740,000

  • 4 Beds
  • 3 Baths
  • 1,456 Sq Ft

  15406 State Route H, Winona, MO 65588

  178-Acre Livestock Farm with Home, Springs & Shop – Shannon County, MOWelcome to your dream farm in the heart of the Missouri Ozarks! This stunning 178-acre livestock-ready property in Shannon County, MO offers the perfect combination of functionality, natural beauty, and rural tranquility.Nestled among rolling pastures and whistling pine trees, the land boasts multiple year-round springs

  Dale Struemph Sports Afield Real Estate

  15406 State Route H, Winona, MO 65588
• 

  

  

  /18

  $149,499 Last List Price Sold Sep 29, 2025

  000 Dd 585, Winona, MO 65588

  • Land
  • 35 Acres
  • $4,271 per Acre

  Last Sold Summary

  • 113 Days On Market

  Last Listing Agent Angela Needels Ozark Land Exchange

  

  000 Dd 585, Winona, MO 65588
• 

  

  /45

  Not Listed For Sale

  0 County Road Dd-585, Winona, MO 65588

  0 County Road Dd-585, Winona, MO 65588

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Karl Ward Midwest Land Group LLC
• 

  

  /30

  $238,140

  • Land
  • 64 Acres
  • $3,721 per Acre

  000 County Road 106, Eminence, MO 65466

  Discover this stunning 64 +/- acres of versatile land offering a perfect blend of privacy and recreational opportunities. Featuring a private well, lagoon, and electrical service, the property is ready for your new build or weekend retreat. A small unfinished shed/cabin provides a potential hunting getaway, while the land borders public land, opening up endless outdoor adventures.Ideal

  Austin Phillips Midwest Land Group

  000 County Road 106, Eminence, MO 65466
• 

  

  /14

  $59,900 Last List Price Sold Jul 11, 2025

  20001 Clear Lake Terrace, Winona, MO 65588

  • 1 Bed
  • 1 Bath
  • 350 Sq Ft
  • Built 2021

  Last Sold Summary

  • $171/SF
  • 24 Days On Market

  Current Estimated Value $60,746

  Last Listing Agent Leanna Bryson Missouri Home Realty

  

  20001 Clear Lake Terrace, Winona, MO 65588
• 

  

  /45

  Not Listed For Sale

  0000 County Road Dd-585, Winona, MO 65588

  

  0000 County Road Dd-585, Winona, MO 65588

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Karl Ward Midwest Land Group
• 

  

  /36

  $696,000

  00 Tbd Highway H, Winona, MO 65588

  Rare opportunity to own a CAVE and 116 acres of prime timberland in Shannon County, MO, just minutes from Eminence and the Ozark National Scenic Riverways. This unique property features a remarkable cave system running over 1,000 feet underground with both an entrance and exit located entirely on the land. Inside the cave, you'll find two large open chambers, striking rock formations, and

  Dale Struemph Sports Afield Real Estate

  00 Tbd Highway H, Winona, MO 65588
• 

  /2

  $1,137,500 Last List Price Sold Apr 18, 2025

  20184 Cr-F-504, Winona, MO 65588

  • Land
  • 455 Acres
  • $2,500 per Acre

  Last Sold Summary

  • 61 Days On Market

  Current Estimated Value $953,312

  Last Listing Agent Jeremy Meyer Sturdy Real Estate

  

  20184 Cr-F-504, Winona, MO 65588
• 

  

  /17

  Est $63,296 Not Listed For Sale

  8115 Weaver St, Winona, MO 65588

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft
  • Built 1961

  

  8115 Weaver St, Winona, MO 65588

  Last Sold Summary

  • $0/SF
  • 12 Days On Market

  Last Listing Agent Jon Thompson RE/MAX
• 

  

  /61

  $379,900

  • 4 Beds
  • 2 Baths
  • 2,100 Sq Ft

  8969 County Road 445, Winona, MO 65588

  FARMING - HUNTING - PRIVACY - COUNTRY HOME!This property is well-suited for horse and equine enthusiasts, hunters, farmers, and those that are ready to enjoy the outdoors.This 4 bedroom / 2 bath house rests on 58.76 acres of functional Ozarks land and corners the Mark Twain National Forest. In addition to the solid home, it has a 40'x40' shop with reinforced concrete floors, 14 ft. walls,

  Dennis Walton 37 North Realty - West Plains

  

  8969 County Road 445, Winona, MO 65588
• 

  

  /7

  $70,000 Last List Price Sold May 21, 2025

  20290 State Route H, Winona, MO 65588

  • Land
  • 13 Acres
  • $5,385 per Acre

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Carla Johnson Keller Williams Southern Missouri Realty

  

  20290 State Route H, Winona, MO 65588
• 

  

  /43

  Est $188,775 Not Listed For Sale

  22344 County Road 214, Eminence, MO 65466

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1900

  

  22344 County Road 214, Eminence, MO 65466

  Last Sold Summary

  • $0/SF
  • 55 Days On Market

  Last Listing Agent Dennis Walton 37 North Realty - West Plains
• 

  

  /41

  $350,000

  • 2 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  8028 Northway Dr, Winona, MO 65588

  Discover the perfect blend of Country living and thought-out useful space in this 2-bedroom, 2.5 bath barndominium situated on 9 +/- beautiful acres. Designed for the ultimate hobbyist, entrepreneur, or entertainer, the property features a massive attached 60x35 heated and cooled shop with a bathroom and space for an additional bedroom and a commercial grade kitchen ideal for the culinary

  Anthony Rodebush Red Cedar Land Company LLC

  

  8028 Northway Dr, Winona, MO 65588
• 

  

  /43

  $344,900 Last List Price Sold Oct 16, 2025

  7709 Huckleberry Ln, Winona, MO 65588

  • 4 Beds
  • 3.5 Baths
  • 1,159 Sq Ft
  • Built 2008

  Last Sold Summary

  • $298/SF
  • 111 Days On Market

  Current Estimated Value $344,999

  Last Listing Agent Debbie Thomason Property Pros Realty LLC

  7709 Huckleberry Ln, Winona, MO 65588
• 

  

  /48

  Est $280,933 Not Listed For Sale

  19241 County Road 579, Winona, MO 65588

  • 3 Beds
  • 2 Baths
  • 2,132 Sq Ft
  • Built 1997

  

  19241 County Road 579, Winona, MO 65588

  Last Sold Summary

  • $0/SF
  • 34 Days On Market

  Last Listing Agent Sandra Ross United Country-Cozort Realty, Inc.
• 

  

  /12

  $299,900

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

  30120 Hwy 60, Ellsinore, MO 65588

  Nice Earth home sitting on 8.43 acres m/l. With 634 ft. of Hwy 60 frontage. Mostly all fenced and in the Ellsinore school district. The home has been recently remodeled with porcelain tile throughout. The property has 2 ponds, an RV shed, and a small outbuilding. Home can be electric or gas.

  Tonya Carter Century 21 American Realty

  30120 Hwy 60, Ellsinore, MO 65588
• 

  

  /35

  $274,900 Last List Price Sold Apr 09, 2025

  10178 Missouri 19, Winona, MO 65588

  • 4 Beds
  • 2.5 Baths
  • 2,597 Sq Ft
  • Built 1971

  Last Sold Summary

  • $106/SF
  • 196 Days On Market

  Current Estimated Value $241,439

  Last Listing Agent Rockie Dailey United Country Real Estate - Ozark Rivers Realty

  

  10178 Missouri 19, Winona, MO 65588
• 

  

  /15

  Est $170,000 Not Listed For Sale

  000 Blue Lake Hights, Winona, MO 65588

  • Built 2018

  

  000 Blue Lake Hights, Winona, MO 65588

  Last Sold Summary

  • $0/SF
  • 299 Days On Market

  Last Listing Agent Darin Jenkins Whitetail Properties Real Estate
• 

  

  /30

  $299,900

  • 5 Beds
  • 3 Baths
  • 4,352 Sq Ft

  9468 State Highway 19, Winona, MO 65588

  This impressive 5-bedroom, 3-bathroom home offers the perfect blend of space, comfort, and convenience with highway frontage and a generous 1.36-acre lot in Winona, Missouri.The main floor features a large master suite complete with an en suite bath, walk-in closet, and private retreat feel. Enjoy the open-concept kitchen and dining area, highlighted by a walk-in pantry that provides

  Rockie Dailey United Country Real Estate - Ozark Rivers Realty

  

  9468 State Highway 19, Winona, MO 65588
• 

  

  /11

  $75,000 Last List Price Sold Jul 21, 2025

  8602 Sapper St, Winona, MO 65588

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft
  • Built 1960

  Last Sold Summary

  • $72/SF
  • 87 Days On Market

  Current Estimated Value $86,973

  Last Listing Agent Angela Needels Ozark Land Exchange

  

  8602 Sapper St, Winona, MO 65588
• 

  

  /23

  Est $354,743 Not Listed For Sale

  15893 Old Highway 60, Winona, MO 65588

  • 3 Beds
  • 2 Baths
  • Built 1995

  

  15893 Old Highway 60, Winona, MO 65588

  Last Sold Summary

  • $0/SF
  • 134 Days On Market

  Last Listing Agent steve willard Ozark Land Exchange
• 

  

  /37

  $274,900 Pending

  • 4 Beds
  • 2 Baths
  • 3,294 Sq Ft

  9023 State Highway 19, Winona, MO 65588

  Spacious Brick Town Home on 5.71 +/- Acres - Edge of Town Setting This beautiful, large brick home offers the perfect blend of town convenience and country space. Featuring four bedrooms and two full bathrooms, this home is designed for comfortable family living. Inside, you'll find a double fireplace creating warmth and charm in both the living and family rooms, plus a full basement offering

  Rockie Dailey United Country Real Estate - Ozark Rivers Realty

  

  9023 State Highway 19, Winona, MO 65588
• 

  

  /9

  $38,900 Last List Price Sold Jul 17, 2025

  0000 E, Winona Township, MO 65588

  • Land
  • 4.4 Acres
  • $8,841 per Acre

  Last Sold Summary

  • 103 Days On Market

  Last Listing Agent Travis Brake Monark Realty

  

  0000 E, Winona Township, MO 65588
• 

  

  /25

  Est $261,023 Not Listed For Sale

  16283 Old Highway 60, Winona, MO 65588

  • 3 Beds
  • 3 Baths
  • 1,977 Sq Ft
  • Built 1966

  

  16283 Old Highway 60, Winona, MO 65588

  Last Sold Summary

  • $0/SF
  • 27 Days On Market

  Last Listing Agent Laurie Nissen Ozark Kountry Realty, Real Estate & Auctioneering
• 

  

  /20

  $219,900

  • 2 Beds
  • 2 Baths
  • 1,305 Sq Ft

  7922 Old Alton Rd, Winona, MO 65588

  Peaceful country living with convenience! This 2 bedroom, 2 bathroom, laundry room the home sits on approximately 6.21 acres (more or less) in Winona, MO, just minutes from rivers, parks, and outdoor recreation. The property is set back off a blacktop road, offering privacy while maintaining easy access. Features include central air conditioning, electric heat, a durable metal roof, and a one-car

  Cricket Anderson Missouri Home Realty

  

  7922 Old Alton Rd, Winona, MO 65588
• 

  

  /44

  $159,900 Last List Price Sold Apr 23, 2025

  2320 County Road 156, Winona, MO 65588

  • 1 Bed
  • 1 Bath
  • 2,212 Sq Ft
  • Built 1993

  Last Sold Summary

  • $72/SF
  • 191 Days On Market

  Current Estimated Value $79,361

  Last Listing Agent Kristie Rackley Iron Brand Realty LLC

  

  2320 County Road 156, Winona, MO 65588
• 

  

  /32

  Est $256,290 Not Listed For Sale

  8214 Cr 563, Winona, MO 65588

  • 4 Beds
  • 3 Baths
  • Built 1978

  8214 Cr 563, Winona, MO 65588

  Last Sold Summary

  • $0/SF
  • 50 Days On Market

  Last Listing Agent Butch Burch Farm & Home Realty
• 

  

  /41

  $159,900

  • 4 Beds
  • 2 Baths
  • 1,237 Sq Ft

  8612 Sapper St, Winona, MO 65588

  Welcome to a home that truly has it all. This move-in-ready 4-bedroom townhouse stands out from the rest, perched on a desirable large corner lot that offers extra space and breathing room. The heart of this home extends outdoors to a backyard designed for celebration; enjoy a full 6-foot wood privacy fence that ensures your gatherings on the spacious deck remain intimate and secure. From the

  Rockie Dailey United Country Real Estate - Ozark Rivers Realty

  

  8612 Sapper St, Winona, MO 65588
• 

  

  /31

  $149,900 Last List Price Sold Apr 14, 2025

  000 County Road 513a, Eminence, MO 65466

  • Land
  • 40 Acres
  • $3,748 per Acre

  Last Sold Summary

  • 266 Days On Market

  Last Listing Agent Abigail Peterson United Country Real Estate - Ozark Rivers Realty

  

  000 County Road 513a, Eminence, MO 65466
• 

  

  /46

  Est $101,376 Not Listed For Sale

  8291 Missouri 19, Winona, MO 65588

  • 3 Beds
  • 1.5 Baths
  • 1,812 Sq Ft
  • Built 1955

  

  8291 Missouri 19, Winona, MO 65588

  Last Sold Summary

  • $0/SF
  • 56 Days On Market

  Last Listing Agent Denise Cunningham Century 21 Combs & Associates
• 

  

  /29

  $230,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  18387 Proffit Rd, Winona, MO 65588

  Escape to peace and privacy on this beautiful 20-acre property, featuring a spacious 4-bedroom, 2-bath mobile home tucked deep in a quiet, secluded setting. Surrounded by nature and set far off the road, this property offers room to relax, roam, and truly enjoy country living. The home offers a comfortable layout perfect for families or guests, with a large living area, functional kitchen, and

  Rockie Dailey United Country Real Estate - Ozark Rivers Realty

  

  18387 Proffit Rd, Winona, MO 65588
• 

  

  /19

  $620,000 Last List Price Sold Sep 10, 2025

  0 County Road A19-227 Unit MAR24054507, Eminence, MO 65466

  Last Sold Summary

  • 336 Days On Market

  Last Listing Agent Natalie Chatman Missouri Home Realty

  0 County Road A19-227 Unit MAR24054507, Eminence, MO 65466
• 

  

  /31

  Est $205,160 Not Listed For Sale

  18120 Ledgerwood Ln, Winona, MO 65588

  • 3 Beds
  • 2 Baths
  • 2,242 Sq Ft
  • Built 1972

  

  18120 Ledgerwood Ln, Winona, MO 65588

  Last Sold Summary

  • $0/SF
  • 132 Days On Market

  Last Listing Agent Cricket Anderson Missouri Home Realty
• 

  

  /39

  $183,000

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  7815 Trinity Ln, Winona, MO 65588

  This beautiful home is situated on a large, private lot on a dead-end street, ensuring minimal traffic. The property spans nearly one acre and is mostly wooded, offering a serene and secluded environment. The home features three bedrooms and two bathrooms, with a spacious open living room and kitchen. It boasts a vaulted ceiling, enhancing the feeling of space throughout the living area. The main

  Rockie Dailey United Country Real Estate - Ozark Rivers Realty

  

  7815 Trinity Ln, Winona, MO 65588
• 

  

  /11

  $209,900 Last List Price Sold Aug 14, 2025

  17909 Roberts Ln, Winona, MO 65588

  • 5 Beds
  • 3.5 Baths
  • 2,654 Sq Ft
  • Built 1995

  Last Sold Summary

  • $79/SF

  Current Estimated Value $223,643

  Last Listing Agent Peggy Ann Bryce Salem Properties

  17909 Roberts Ln, Winona, MO 65588
• 

  

  /71

  Est $332,911 Not Listed For Sale

  17707 County Road 419, Winona, MO 65588

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1984

  

  17707 County Road 419, Winona, MO 65588

  Last Sold Summary

  • $0/SF
  • 157 Days On Market

  Last Listing Agent Marla Kay Denton 37 North Realty - Mountain View
• 

  

  /20

  $63,900

  • Land
  • 12.8 Acres
  • $4,992 per Acre

  000 Forest Road 3169, Winona, MO 65588

  This picturesque 12.8-acre tract is primarily wooded and features mostly level terrain with a gentle slope, providing numerous excellent sites for building your dream home. The property has county road frontage and electricity available along the road, as well as an easement road on the north side for access. Enjoy the privacy and natural beauty while being within walking distance to thousands of

  Darin Jenkins Whitetail Properties Real Estate

  

  000 Forest Road 3169, Winona, MO 65588

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