Winona County, MN Homes

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  /53

  $495,000

  • 4 Beds
  • 2 Baths
  • 2,453 Sq Ft

  398 Pleasant Hill Dr, Winona, MN 55987

  Welcome to this beautifully updated multi-level home in the highly desirable Knopp Valley. Offering 4 bedrooms and 2 bathrooms, the home features a bright and open layout with multiple living spaces designed for comfort and flexibility. A 2-car attached garage completes this exceptional property.Major exterior updates include a new roof, vinyl siding, windows, exterior and interior doors, and

  Eric Nustad Key Real Estate

  398 Pleasant Hill Dr, Winona, MN 55987
• 

  $190,000

  Sold Nov 24, 2025

  752 E 2nd St, Winona, MN 55987

  • 3 Beds
  • 2.5 Baths
  • 1,558 Sq Ft

  Last Sold Summary

  • $122/SF
  • 11 Days On Market

  Current Estimated Value $188,801

  Last Listing Agent Celeste Liesch Edina Realty, Inc

  752 E 2nd St, Winona, MN 55987
• 

  

  

  /28

  Est $215,959

  Not Listed For Sale

  1071 Gilmore Ave, Winona, MN 55987

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1952

  1071 Gilmore Ave, Winona, MN 55987

  Last Sold Summary

  • 2% Above List Price
  • $170/SF
  • 45 Days On Market

  • Last Sold Price $212,500
  • Jul 12, 2024

  Last Listing Agent Tristyn Hutchins Coffee House Real Estate LLC
• 

  

  

  /13

  $55,000

  • Land
  • 8,712 Sq Ft
  • $275,000 per Acre

  225 Pheasant Run, Rollingstone, MN 55969

  Have you ever dreamed of building your own home? Rollingstone, MN is the perfect place to make this dream a reality. This beautiful town is approximately 20 minutes from the East end and approximately 10 minutes from the West end of Winona. They are ready-to-build lots with all the amenities, including city water and sewer, electric, two internet providers, and natural gas. All assessments are

  Gile Gibbons Edina Realty, Inc.

  225 Pheasant Run, Rollingstone, MN 55969
• 

  

  

  /30

  $225,000

  Sold Jan 09, 2026

  512 E Wabasha St, Winona, MN 55987

  • 3 Beds
  • 2 Baths
  • 1,468 Sq Ft
  • Built 1875

  Last Sold Summary

  • $153/SF
  • 151 Days On Market

  Last Listing Agent Tim Tlougan Edina Realty, Inc.

  512 E Wabasha St, Winona, MN 55987
• 

  

  /30

  Est $264,882

  Not Listed For Sale

  626 Clarks Ln, Winona, MN 55987

  • 4 Beds
  • 2.5 Baths
  • 2,329 Sq Ft
  • Built 1935

  626 Clarks Ln, Winona, MN 55987

  Last Sold Summary

  • 13% Above List Price
  • $101/SF
  • 59 Days On Market

  • Last Sold Price $235,000
  • Nov 13, 2024

  Last Listing Agent Tim Tlougan Edina Realty, Inc.
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  /39

  $249,900

  Open Sun 1:30PM - 3PM $100K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,056 Sq Ft

  1231 Church Ave, Saint Charles, MN 55972

  Step into timeless character with this charming 1915 home located in the heart of Saint Charles. Full of original charm and warmth, this home blends historic appeal with thoughtful updates throughout. A kitchen addition completed in 2005 provides added space and functionality, making it perfect for everyday living and entertaining. Recent improvements offer peace of mind, including a beautifully

  Camille Hanson Edina Realty, Inc.

  1231 Church Ave, Saint Charles, MN 55972
• 

  /2

  $735,000

  Sold Mar 18, 2026

  150 2nd St S, Lewiston, MN 55952

  • 2 Beds
  • 1 Bath
  • 6,944 Sq Ft
  • Built 1972

  Last Sold Summary

  • 8% Below List Price
  • $106/SF
  • 37 Days On Market

  Last Listing Agent Cherie Burke Keller Williams Premier Realty

  150 2nd St S, Lewiston, MN 55952
• 

  

  /48

  Est $623,785

  Not Listed For Sale

  121 W Lake Blvd, Winona, MN 55987

  • 4 Beds
  • 3.5 Baths
  • 3,608 Sq Ft
  • Built 1975

  121 W Lake Blvd, Winona, MN 55987

  Last Sold Summary

  • 4% Above List Price
  • $166/SF
  • 84 Days On Market

  • Last Sold Price $600,000
  • Jun 28, 2024

  Last Listing Agent Wendy Killen Keller Williams Premier Realty
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  /37

  $485,000

  Open Sat 10AM - 12PM $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,880 Sq Ft

  15107 County Road 25, Rollingstone, MN 55969

  Welcome to this 4-bedroom, 2 bath split level home set on 11.06 beautiful acres in a peaceful area, offering the perfect blend of comfort, space, and outdoor opportunity. This well-maintained property features a functional layout with room to grow, both inside and out. Enjoy expansive land ideal for hunting, recreation and all your outdoor hobbies. Whether you're looking for privacy, adventure,

  Kendra Speltz Edina Realty, Inc.

  15107 County Road 25, Rollingstone, MN 55969
• 

  

  /31

  $345,500

  Sold Dec 04, 2025

  42671 Lisa Ln, Winona, MN 55987

  • 3 Beds
  • 2 Baths
  • 2,268 Sq Ft
  • Built 1976

  Last Sold Summary

  • $152/SF
  • 16 Days On Market

  Current Estimated Value $342,774

  Last Listing Agent Hannah Schmidt eXp Realty

  42671 Lisa Ln, Winona, MN 55987
• 

  

  /30

  Est $221,129

  Not Listed For Sale

  512 Junction St, Winona, MN 55987

  • 2 Beds
  • 1 Bath
  • 975 Sq Ft
  • Built 1933

  512 Junction St, Winona, MN 55987

  Last Sold Summary

  • 11% Above List Price
  • $205/SF
  • 11 Days On Market

  • Last Sold Price $200,000
  • Sep 28, 2023

  Last Listing Agent Angela Thompson Coldwell Banker River Valley, REALTORS
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  /4

  $178,365

  • Land
  • 32,234 Sq Ft
  • $241,034 per Acre

  211 Industrial Park Dr, Saint Charles, MN 55972

  Great lot to build your future business.

  Dan Pearson Coldwell Banker River Valley,

  211 Industrial Park Dr, Saint Charles, MN 55972
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  /42

  $592,000

  Sold Jul 08, 2025

  131 Jay Bee Dr, Winona, MN 55987

  • 4 Beds
  • 4 Baths
  • 4,356 Sq Ft
  • Built 1984

  Last Sold Summary

  • $136/SF
  • 11 Days On Market

  Current Estimated Value $596,174

  Last Listing Agent Sonja Kunce Coldwell Banker River Valley, REALTORS

  131 Jay Bee Dr, Winona, MN 55987
• 

  

  /24

  Est $218,868

  Not Listed For Sale

  851 W Wabasha St, Winona, MN 55987

  • 3 Beds
  • 1.5 Baths
  • 1,592 Sq Ft
  • Built 1886

  851 W Wabasha St, Winona, MN 55987

  Last Sold Summary

  • 11% Above List Price
  • $124/SF
  • 5 Days On Market

  • Last Sold Price $197,500
  • Jun 27, 2023

  Last Listing Agent Angela Thompson Coldwell Banker River Valley, REALTORS
• 

  /2

  $250,000

  • Land
  • 1.5 Acres
  • $166,667 per Acre

  tbd Roberts St, Saint Charles, MN 55972

  Next development right on the edge of the desirable St. Charles. Asking price consists of 1.5 acres for 6 twin homes currently going through the plat process. May split up, developer could choose another route, multiple opportunities.

  Mitchell Walch Coffee House Real Estate LLC

  tbd Roberts St, Saint Charles, MN 55972
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  /42

  $359,900

  Sold Oct 17, 2025

  611 Clarks Ln, Winona, MN 55987

  • 5 Beds
  • 2.5 Baths
  • 2,066 Sq Ft
  • Built 1926

  Last Sold Summary

  • $174/SF
  • 85 Days On Market

  Current Estimated Value $361,389

  Last Listing Agent Brent Kimmerle Real Broker, LLC.

  611 Clarks Ln, Winona, MN 55987
• 

  

  /22

  Est $183,103

  Not Listed For Sale

  972 W 2nd St, Winona, MN 55987

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

  972 W 2nd St, Winona, MN 55987

  Last Sold Summary

  • 11% Above List Price
  • $173/SF
  • 36 Days On Market

  • Last Sold Price $165,050
  • Nov 22, 2024

  Last Listing Agent Nathaniel McEntaffer Edina Realty, Inc.
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  /34

  $620,000

  $30K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,831 Sq Ft

  1397 Soppa Dr, Saint Charles, MN 55972

  Discover the incredible opportunity to own this expansive custom-built home nestled on 2.25 scenic acres in Saint Charles. Built in 1989, this one-of-a-kind property offers over 6000 finished square feet of living space, providing endless possibilities to update, personalize, and create your dream home. Inside, you'll find generous living areas, spacious rooms, and a thoughtful custom design that

  Camille Hanson Edina Realty, Inc.

  1397 Soppa Dr, Saint Charles, MN 55972
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  /40

  $580,000

  Sold Jan 16, 2026

  41084 Big Trout Ln, Winona, MN 55987

  • 3 Beds
  • 3 Baths
  • 2,428 Sq Ft
  • Built 1993

  Last Sold Summary

  • $239/SF
  • 31 Days On Market

  Current Estimated Value $580,287

  Last Listing Agent Matt Loos Real Broker, LLC.

  41084 Big Trout Ln, Winona, MN 55987
• 

  Est $239,821

  Not Listed For Sale

  1728 Gilmore Ave, Winona, MN 55987

  • 2 Beds
  • 1.5 Baths
  • 2,108 Sq Ft
  • Built 1955

  1728 Gilmore Ave, Winona, MN 55987

  Last Sold Summary

  • 2% Above List Price
  • $112/SF
  • 5 Days On Market

  • Last Sold Price $235,500
  • Mar 28, 2025

  Last Listing Agent Jenny Cisewski Edina Realty, Inc
• 

  

  /24

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,548 Sq Ft

  205 Whitten St, Winona, MN 55987

  Charming ranch-style home on a desirable corner lot! This well-maintained property features three main-floor bedrooms, an inviting living room with a cozy fireplace—perfect for relaxing evenings, and a deck for relaxing outdoors. Downstairs, you’ll find a spacious lower-level family room, ideal for entertaining, hobbies, or movie nights. With a functional layout, comfortable living spaces, and

  Jason Hubbard Real Broker, LLC.

  205 Whitten St, Winona, MN 55987
• 

  

  /27

  $330,000

  Sold Mar 31, 2026

  628 Main St, Winona, MN 55987

  • 4 Beds
  • 3.5 Baths
  • 2,562 Sq Ft
  • Built 1931

  Last Sold Summary

  • 6% Below List Price
  • $129/SF
  • 21 Days On Market

  Current Estimated Value $313,215

  Last Listing Agent Camille Hanson Edina Realty, Inc.

  628 Main St, Winona, MN 55987
• 

  

  /14

  Est $185,690

  Not Listed For Sale

  1729 W 5th St, Winona, MN 55987

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Built 1890

  1729 W 5th St, Winona, MN 55987

  Last Sold Summary

  • 1% Below List Price
  • $144/SF
  • 44 Days On Market

  • Last Sold Price $187,000
  • Mar 03, 2025

  Last Listing Agent Rachel Jacobs Key Real Estate
• 

  /2

  $141,637

  Pending

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  30810 Highway 74, Saint Charles, MN 55972

  2 bedroom home in a private country setting. Newer well, metal roof

  Lynn Franko Coldwell Banker River Valley,

  30810 Highway 74, Saint Charles, MN 55972
• 

  

  /44

  $288,000

  Sold Mar 27, 2026

  81010 E Main St, Winona, MN 55987

  • 3 Beds
  • 1 Bath
  • 2,747 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $105/SF
  • 23 Days On Market

  Current Estimated Value $294,310

  Last Listing Agent John Nelson RE/MAX Results

  81010 E Main St, Winona, MN 55987
• 

  

  /24

  Est $198,394

  Not Listed For Sale

  1614 W 5th St, Winona, MN 55987

  • 3 Beds
  • 1.5 Baths
  • 1,088 Sq Ft
  • Built 1900

  1614 W 5th St, Winona, MN 55987

  Last Sold Summary

  • 48% Above List Price
  • $123/SF
  • 76 Days On Market

  • Last Sold Price $134,000
  • Jan 08, 2024

  Last Listing Agent Christopher Jacobson Richard L. Jacobson Real Estate
• 

  

  /17

  $125,000

  Pending

  • 2 Beds
  • 1 Bath
  • 772 Sq Ft

  959 W 2nd St, Winona, MN 55987

  Charming and cozy 2-bedroom home offering comfortable main-level living! This well-maintained property features an inviting layout with all essential spaces conveniently located on one floor. Enjoy a partially fenced yard—perfect for relaxing, entertaining, or pets. Rental certified for added peace of mind, making it a great option for homeowners or investors alike.

  Jason Hubbard Real Broker, LLC.

  959 W 2nd St, Winona, MN 55987
• 

  

  /25

  $255,000

  Sold May 07, 2026

  1565 W King St, Winona, MN 55987

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1951

  Last Sold Summary

  • 4% Above List Price
  • $163/SF
  • 2 Days On Market

  Current Estimated Value $238,458

  Last Listing Agent Brianna Peck Real Broker, LLC.

  1565 W King St, Winona, MN 55987
• 

  

  /16

  Est $235,102

  Not Listed For Sale

  273 Sebo St, Winona, MN 55987

  • 3 Beds
  • 1 Bath
  • 1,604 Sq Ft
  • Built 1977

  273 Sebo St, Winona, MN 55987

  Last Sold Summary

  • 15% Above List Price
  • $128/SF
  • 0 Days On Market

  • Last Sold Price $205,000
  • Jul 14, 2023

  Last Listing Agent Jilaine Schmidt Edina Realty, Inc.
• 

  

  /5

  $35,000

  • Land
  • 13,939 Sq Ft
  • $109,375 per Acre

  1113 Oakview Dr, Saint Charles, MN 55972

  Go and Show.

  Dan Pearson Coldwell Banker River Valley,

  1113 Oakview Dr, Saint Charles, MN 55972
• 

  

  /15

  $210,000

  Sold Dec 05, 2025

  207 E Sanborn St, Winona, MN 55987

  • 5 Beds
  • 2 Baths
  • 2,028 Sq Ft
  • Built 1882

  Last Sold Summary

  • $104/SF
  • 23 Days On Market

  Current Estimated Value $208,805

  Last Listing Agent Laura Slavey Keller Williams Premier Realty

  207 E Sanborn St, Winona, MN 55987
• 

  

  /39

  Est $254,777

  Not Listed For Sale

  1858 Gilmore Ave, Winona, MN 55987

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft
  • Built 1880

  1858 Gilmore Ave, Winona, MN 55987

  Last Sold Summary

  • 13% Above List Price
  • $136/SF
  • 1 Day On Market

  • Last Sold Price $226,000
  • Oct 14, 2023

  Last Listing Agent Angela Thompson Coldwell Banker River Valley, REALTORS
• 

  

  /80

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,392 Sq Ft

  33303 County Road 29, Peterson, MN 55962

  Premier Country Home on 4.5 Acres. Beautifully designed ranch-style home offering 3+ bedrooms and 2.5 baths, featuring vaulted ceilings and large windows that fill the space with natural light. The open-concept layout seamlessly connects the living and formal dining areas, highlighted by a striking double-sided fireplace—perfect for both everyday living and entertaining. The well-appointed

  Roxanne Johnson RE/MAX Select Properties

  33303 County Road 29, Peterson, MN 55962
• 

  

  /28

  $193,500

  Sold May 08, 2026

  469 E 7th St, Winona, MN 55987

  • 2 Beds
  • 1 Bath
  • 1,062 Sq Ft
  • Built 1884

  Last Sold Summary

  • 5% Above List Price
  • $182/SF
  • 3 Days On Market

  Last Listing Agent Laura Slavey Keller Williams Premier Realty

  469 E 7th St, Winona, MN 55987
• 

  

  /18

  Est $187,140

  Not Listed For Sale

  67 W Sarnia St, Winona, MN 55987

  • 2 Beds
  • 1 Bath
  • 953 Sq Ft
  • Built 1954

  67 W Sarnia St, Winona, MN 55987

  Last Sold Summary

  • 9% Above List Price
  • $180/SF
  • 5 Days On Market

  • Last Sold Price $172,000
  • Oct 02, 2023

  Last Listing Agent DeAnne Forsythe Coldwell Banker River Valley, REALTORS
• 

  

  /26

  $279,900

  Open Sun 11AM - 1PM $10K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 1,132 Sq Ft

  1304 Mcnally Dr, Winona, MN 55987

  Enjoy easy one-level living in this beautifully remodeled 2-bedroom, 1-bath townhome with an attached 2-car garage and private patio. Thoughtfully redesigned with an open floor plan, this home features heated floors in the kitchen and bathroom, adding everyday comfort and luxury. The kitchen is a true highlight with granite countertops, soft-close cabinetry, and high-end appliances, seamlessly

  Angela Thompson Coldwell Banker River Valley, REALTORS

  1304 Mcnally Dr, Winona, MN 55987
• 

  

  /25

  $215,000

  Sold Jul 25, 2025

  759 E Howard St, Winona, MN 55987

  • 4 Beds
  • 1.5 Baths
  • 2,000 Sq Ft
  • Built 1900

  Last Sold Summary

  • $108/SF
  • 11 Days On Market

  Current Estimated Value $218,827

  Last Listing Agent Matt Loos Real Broker, LLC.

  759 E Howard St, Winona, MN 55987
• 

  

  /25

  Est $323,221

  Not Listed For Sale

  706 Johnson St, Winona, MN 55987

  • 2 Beds
  • 1.5 Baths
  • 1,513 Sq Ft
  • Built 1925

  706 Johnson St, Winona, MN 55987

  Last Sold Summary

  • 5% Below List Price
  • $224/SF
  • 3 Days On Market

  • Last Sold Price $338,500
  • Dec 06, 2024

  Last Listing Agent Nikki Heilman Edina Realty, Inc.
• 

  

  /35

  $619,900

  $50K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 4,068 Sq Ft

  1955 Brownell St, Saint Charles, MN 55972

  Step into this custom built 5 bed 4 bath home, vaulted ceilings, quartz counters, tile work, secondary unit could be perfect for an air bnb, and garage space (6 car attached, rv bay) that is perfect for all of the toys even an rv. Sitting on a private corner lot with a level back yard you can feel like you are in the country with all of the close amenities to town.

  Mitchell Walch Coffee House Real Estate LLC

  1955 Brownell St, Saint Charles, MN 55972

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