3,899

Osceola, WI Homes

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  • 32 256th St, Osceola, WI 54020
    32 256th St, Osceola, WI 54020
    32 256th St, Osceola, WI 54020
    /47

    $525,000

    New Construction Open Sat 2PM - 4PM
    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    32 256th St, Osceola, WI 54020

    Enjoy the ease of single level living in this beautifully finished new construction home situated on 2 peaceful acres. Designed with both comfort and functionality in mind, the home offers 3 bedrooms, 3 bathrooms and a bright, open layout enhanced by impressive 10 foot ceilings. The kitchen features Whirlpool stainless steel appliances and flows effortlessly into the generous dining and living

    Stephanie Checkley Keller Williams Premier Realty

    32 256th St, Osceola, WI 54020
  • 2146 84th Ave, Osceola, WI 54020
    2146 84th Ave, Osceola, WI 54020
    /2

    $439,000

    Sold Apr 09, 2026

    2146 84th Ave, Osceola, WI 54020

    • 4 Beds
    • 3 Baths
    • 2,800 Sq Ft
    • Built 2001

    Last Sold Summary

    • $157/SF
    • 131 Days On Market

    Current Estimated Value $449,185

    Last Listing Agent Mark Kovatch Coldwell Banker Realty

    2146 84th Ave, Osceola, WI 54020
    • 406 Delmar Ave, Osceola, WI 54020
      406 Delmar Ave, Osceola, WI 54020
      /2

      Est $332,244

      Not Listed For Sale

      406 Delmar Ave, Osceola, WI 54020

      • 4 Beds
      • 2 Baths
      • 1,689 Sq Ft
      • Built 1998
      406 Delmar Ave, Osceola, WI 54020

  • Lot 61 Simmon Dr, Osceola, WI 54020
    Lot 61 Simmon Dr, Osceola, WI 54020
    Lot 61 Simmon Dr, Osceola, WI 54020
    /18

    $650,000

    • Land
    • 4.37 Acres
    • $148,741 per Acre

    Lot 61 Simmon Dr, Osceola, WI 54020

    Commercial site in Osceola, that is part of the Gateway Meadows Development. Now that the development is getting built out, this is prime for a gas station and convenience store.

    Michael Muske RE/MAX Synergy

    Lot 61 Simmon Dr, Osceola, WI 54020
  • 912 Maple Dr, Osceola, WI 54020
    912 Maple Dr, Osceola, WI 54020
    912 Maple Dr, Osceola, WI 54020
    /43

    $318,000

    Sold Oct 20, 2025

    912 Maple Dr, Osceola, WI 54020

    • 3 Beds
    • 2 Baths
    • 2,210 Sq Ft
    • Built 1977

    Last Sold Summary

    • $144/SF
    • 12 Days On Market

    Current Estimated Value $336,889

    Last Listing Agent Ryan Berner Realty Executives Top Results

    912 Maple Dr, Osceola, WI 54020
    • 410 Delmar Ave, Osceola, WI 54020
      410 Delmar Ave, Osceola, WI 54020
      410 Delmar Ave, Osceola, WI 54020
      /40

      Est $335,667

      Not Listed For Sale

      410 Delmar Ave, Osceola, WI 54020

      • 3 Beds
      • 2 Baths
      • 1,804 Sq Ft
      • Built 1998
      410 Delmar Ave, Osceola, WI 54020

      Last Sold Summary

      • 117 Days On Market

      Last Listing Agent Sheri Rude Edina Realty, Corp. - St Croix Falls

  • xxx 65th Ave, Osceola, WI 54020
    xxx 65th Ave, Osceola, WI 54020
    xxx 65th Ave, Osceola, WI 54020
    /21

    $1,789,000

    • Land
    • 162.64 Acres
    • $11,000 per Acre

    xxx 65th Ave, Osceola, WI 54020

    Currently the parcel is high quality tillable acrss consisting on mainly Dakota Loam with 0-3% slope. However the parcel has a very high development potential by being adjacent to the Village of Osceola. Currently there is a village road on north boundary with municipal water installed. There has been extensive engineer work done and partial approval from Village for development.

    Brent Wernlund Edina Realty, Inc.

    xxx 65th Ave, Osceola, WI 54020
  • 881 217th St, Osceola, WI 54020
    881 217th St, Osceola, WI 54020
    881 217th St, Osceola, WI 54020
    /20

    $379,000

    Sold Aug 28, 2025

    881 217th St, Osceola, WI 54020

    • 3 Beds
    • 3 Baths
    • 1,908 Sq Ft
    • Built 2001

    Last Sold Summary

    • $199/SF
    • 19 Days On Market

    Current Estimated Value $398,014

    Last Listing Agent Michelle Austad 715 Real Estate

    881 217th St, Osceola, WI 54020
    • 834 Oak Ct, Osceola, WI 54020
      834 Oak Ct, Osceola, WI 54020
      834 Oak Ct, Osceola, WI 54020
      /11

      Est $232,090

      Not Listed For Sale

      834 Oak Ct, Osceola, WI 54020

      • 2 Beds
      • 2 Baths
      • 1,240 Sq Ft
      • Built 1992
      834 Oak Ct, Osceola, WI 54020

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Jean Lundgren Keller Williams Integrity WI/MN

  • 601 3rd Ave E, Osceola, WI 54020
    601 3rd Ave E, Osceola, WI 54020
    601 3rd Ave E, Osceola, WI 54020
    /60

    $400,000

    $25K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,762 Sq Ft

    601 3rd Ave E, Osceola, WI 54020

    This property includes the 4 bedroom home located on .37-acre parcel, and also the adjoining .48-acre vacant land lot! This is a great investment opportunity to keep the second lot for space (no neighbor!) or sell the lot in the future. Perhaps build a new home on it while you live in the existing home; or build a mother-in-law home next door, or build your dream garage! Step inside to a

    Tony Johnson Edina Realty, Corp. - St Croix Falls

    601 3rd Ave E, Osceola, WI 54020
  • 650 Deer Path, Osceola, WI 54020
    650 Deer Path, Osceola, WI 54020
    650 Deer Path, Osceola, WI 54020
    /28

    $295,000

    Sold Aug 06, 2026

    650 Deer Path, Osceola, WI 54020

    • 2 Beds
    • 2 Baths
    • 1,720 Sq Ft
    • Built 2004

    Last Sold Summary

    • 6% Below List Price
    • $172/SF
    • 90 Days On Market

    Current Estimated Value $309,544

    Last Listing Agent Jean Lundgren Keller Williams Integrity WI/MN

    650 Deer Path, Osceola, WI 54020
    • 826 Oak Ct, Osceola, WI 54020
      826 Oak Ct, Osceola, WI 54020
      826 Oak Ct, Osceola, WI 54020
      /29

      Est $225,829

      Not Listed For Sale

      826 Oak Ct, Osceola, WI 54020

      • 2 Beds
      • 1.5 Baths
      • 1,160 Sq Ft
      • Built 1990
      826 Oak Ct, Osceola, WI 54020

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Candice Mueller RE/MAX Synergy/Osceola

  • 298 Zindaus St, Osceola, WI 54020
    298 Zindaus St, Osceola, WI 54020
    298 Zindaus St, Osceola, WI 54020
    /8

    $689,000

    • Land
    • 2.27 Acres
    • $303,524 per Acre

    298 Zindaus St, Osceola, WI 54020

    Fabulous commercial opportunity in Osceola! 2.27 acres with endless possibilities!

    Teri Kampmeyer Coldwell Banker Realty

    298 Zindaus St, Osceola, WI 54020
  • 890 Maple Dr, Osceola, WI 54020
    890 Maple Dr, Osceola, WI 54020
    890 Maple Dr, Osceola, WI 54020
    /35

    $260,000

    Sold Apr 10, 2026

    890 Maple Dr, Osceola, WI 54020

    • 4 Beds
    • 2.5 Baths
    • 2,852 Sq Ft
    • Built 1982

    Last Sold Summary

    • 12% Below List Price
    • $91/SF
    • 72 Days On Market

    Current Estimated Value $296,374

    Last Listing Agent Jean Lundgren Keller Williams Integrity WI/MN

    890 Maple Dr, Osceola, WI 54020
    • 502 Seminole Ave, Osceola, WI 54020
      502 Seminole Ave, Osceola, WI 54020
      502 Seminole Ave, Osceola, WI 54020
      /25

      Est $358,985

      Not Listed For Sale

      502 Seminole Ave, Osceola, WI 54020

      • 4 Beds
      • 4 Baths
      • 2,740 Sq Ft
      • Built 1982
      502 Seminole Ave, Osceola, WI 54020

      Last Sold Summary

      • 94 Days On Market

      Last Listing Agent Lisa Hansen Epique Realty

  • 0 Helen Ln Unit 50298327, Osceola, WI 53010
    0 Helen Ln Unit 50298327, Osceola, WI 53010
    0 Helen Ln Unit 50298327, Osceola, WI 53010
    /11

    $89,900

    Under Contract
    • Land
    • 2.13 Acres
    • $42,207 per Acre

    0 Helen Ln Unit 50298327, Osceola, WI 53010

    Build your dream home now or later, with your choice of builder. Choose the address now in the beautiful Oak Ridge Estates subdivision. Located in the desirable Kettle Moraine area close to several lakes & trails. Minutes away from 45 and 41 for easy travel. Minimal subdivision restrictions apply. A beautiful place to call your own! Perk tests included.

    Sarah Voss Adashun Jones, Inc.

    0 Helen Ln Unit 50298327, Osceola, WI 53010
  • 48 279th St, Osceola, WI 54020
    48 279th St, Osceola, WI 54020
    48 279th St, Osceola, WI 54020
    /54

    $580,000

    Sold Mar 25, 2026

    48 279th St, Osceola, WI 54020

    • 3 Beds
    • 2.5 Baths
    • 2,956 Sq Ft
    • Built 2006

    Last Sold Summary

    • 5% Above List Price
    • $196/SF
    • 10 Days On Market

    Current Estimated Value $671,426

    Last Listing Agent Michael Germain RE/MAX Team 1 Realty

    48 279th St, Osceola, WI 54020
    • 411 Ridge Rd Unit C, Osceola, WI 54020
      411 Ridge Rd Unit C, Osceola, WI 54020
      411 Ridge Rd Unit C, Osceola, WI 54020
      /70

      Est $633,272

      Not Listed For Sale

      411 Ridge Rd Unit C, Osceola, WI 54020

      • 4 Beds
      • 4.5 Baths
      • 3,914 Sq Ft
      • Built 2004
      411 Ridge Rd Unit C, Osceola, WI 54020

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Sheri Rude Edina Realty, Inc.

  • 909 N Cascade St, Osceola, WI 54020
    909 N Cascade St, Osceola, WI 54020
    909 N Cascade St, Osceola, WI 54020
    /26

    $799,000

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,253 Sq Ft

    909 N Cascade St, Osceola, WI 54020

    166 feet of St Croix River frontage and 2.93 Acres, with a waterfall on the path to the river. First time available since the home was custom built in 2005. Heavily wooded, with massive white pine and maple trees. Three bedrooms, three baths. The 3 car heated garage has a finished ceiling, and a separate entrance to the lower level of the house.Vaulted ceilings, cherry woodwork for kitchen

    Ralph Peterson Coldwell Banker Realty

    909 N Cascade St, Osceola, WI 54020
  • Lt12 Red Oak Dr, Osceola, WI 53010

    $58,000

    Sold Mar 06, 2026

    Lt12 Red Oak Dr, Osceola, WI 53010

    • Land
    • 1.14 Acres
    • $50,877 per Acre

    Last Sold Summary

    • 2% Below List Price
    • 27 Days On Market

    Last Listing Agent Elizabeth Augustyn Birchwood Properties LLC

    Lt12 Red Oak Dr, Osceola, WI 53010
    • 922 Circle Ct, Osceola, WI 54020
      922 Circle Ct, Osceola, WI 54020
      /2

      Est $347,830

      Not Listed For Sale

      922 Circle Ct, Osceola, WI 54020

      • 3 Beds
      • 2 Baths
      • 2,089 Sq Ft
      • Built 1989
      922 Circle Ct, Osceola, WI 54020

  • 0 Helen Ln Unit 50298328, Osceola, WI 53010
    0 Helen Ln Unit 50298328, Osceola, WI 53010
    0 Helen Ln Unit 50298328, Osceola, WI 53010
    /11

    $89,900

    • Land
    • 2.13 Acres
    • $42,207 per Acre

    0 Helen Ln Unit 50298328, Osceola, WI 53010

    Build your dream home now or later, with your choice of builder. Choose the address now in the beautiful Oak Ridge Estates subdivision. Located in the desirable Kettle Moraine area close to several lakes & trails. Minutes away from 45 and 41 for easy travel. Minimal subdivision restrictions apply. A beautiful place to call your own! Perk tests included.

    Sarah Voss Adashun Jones, Inc.

    0 Helen Ln Unit 50298328, Osceola, WI 53010
  • 106 Prairie Grass Dr, Osceola, WI 54020
    106 Prairie Grass Dr, Osceola, WI 54020
    106 Prairie Grass Dr, Osceola, WI 54020
    /82

    $425,000

    Sold Sep 12, 2025

    106 Prairie Grass Dr, Osceola, WI 54020

    • 4 Beds
    • 3 Baths
    • 2,776 Sq Ft
    • Built 2014

    Last Sold Summary

    • $153/SF
    • 20 Days On Market

    Current Estimated Value $451,058

    Last Listing Agent Joshua Leonhardt Coldwell Banker Realty

    106 Prairie Grass Dr, Osceola, WI 54020
    • 909 Martys Way, Osceola, WI 54020
      909 Martys Way, Osceola, WI 54020
      909 Martys Way, Osceola, WI 54020
      /9

      Est $296,518

      Not Listed For Sale

      909 Martys Way, Osceola, WI 54020

      • 2 Beds
      • 1 Bath
      • 1,092 Sq Ft
      • Built 1993
      909 Martys Way, Osceola, WI 54020

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Cheryl Retterath Edina Realty, Inc.

  • 853 217th St, Osceola, WI 54020
    853 217th St, Osceola, WI 54020
    853 217th St, Osceola, WI 54020
    /30

    $449,900

    Pending
    • 5 Beds
    • 3 Baths
    • 2,595 Sq Ft

    853 217th St, Osceola, WI 54020

    Molly Irish Keller Williams Premier Realty

    853 217th St, Osceola, WI 54020
  • 2519 86th Ave, Osceola, WI 54020
    2519 86th Ave, Osceola, WI 54020
    2519 86th Ave, Osceola, WI 54020
    /53

    $595,000

    Sold Aug 04, 2026

    2519 86th Ave, Osceola, WI 54020

    • 4 Beds
    • 3.5 Baths
    • 3,037 Sq Ft
    • Built 2000

    Last Sold Summary

    • $196/SF
    • 34 Days On Market

    Current Estimated Value $584,654

    Last Listing Agent Peggy Weber Keller Williams Integrity WI/MN

    2519 86th Ave, Osceola, WI 54020
    • 898 Maple Dr, Osceola, WI 54020
      898 Maple Dr, Osceola, WI 54020
      898 Maple Dr, Osceola, WI 54020
      /28

      Est $291,204

      Not Listed For Sale

      898 Maple Dr, Osceola, WI 54020

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1979
      898 Maple Dr, Osceola, WI 54020

      Last Sold Summary

      • 119 Days On Market

      Last Listing Agent Katherine Demulling Marathon Realty

  • 342 Paulsen Lake Ct, Osceola, WI 54020
    342 Paulsen Lake Ct, Osceola, WI 54020
    342 Paulsen Lake Ct, Osceola, WI 54020
    /29

    $375,000

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    342 Paulsen Lake Ct, Osceola, WI 54020

    Built in 2023, this inviting lakeside home on the shores of Paulsen Lake offers comfort, style, and beautiful water views. Featuring 2 bedrooms, a full bath, and an additional loft space ideal for extra sleeping accommodations, the home is designed for both relaxation and entertaining. Large vaulted ceilings and expansive windows fill the interior with natural light while framing views of the

    Kyle Hinrichs RE/MAX Team 1 Realty

    342 Paulsen Lake Ct, Osceola, WI 54020
  • 290 Spring St, Osceola, WI 54020
    290 Spring St, Osceola, WI 54020
    /2

    $305,000

    Sold May 29, 2026

    290 Spring St, Osceola, WI 54020

    • 2 Beds
    • 2 Baths
    • 1,185 Sq Ft
    • Built 2026

    Last Sold Summary

    • $257/SF
    • 148 Days On Market

    Current Estimated Value $301,675

    Last Listing Agent Candice Mueller RE/MAX Synergy

    290 Spring St, Osceola, WI 54020
    • 893 Maple Dr, Osceola, WI 54020
      893 Maple Dr, Osceola, WI 54020
      893 Maple Dr, Osceola, WI 54020
      /35

      Est $298,230

      Not Listed For Sale

      893 Maple Dr, Osceola, WI 54020

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1985
      893 Maple Dr, Osceola, WI 54020

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Jamie Fahrenkrug EXP Realty, LLC

  • Lt2 Happy Hollow Rd, Osceola, WI 54020
    Lt2 Happy Hollow Rd, Osceola, WI 54020
    Lt2 Happy Hollow Rd, Osceola, WI 54020
    /12

    $149,900

    • Land
    • 6 Acres
    • $24,983 per Acre

    Lt2 Happy Hollow Rd, Osceola, WI 54020

    Discover the perfect canvas for your dream home on a sprawling 6.0 acre lot, nestled in the tranquil embrace of nature. Create a private oasis on this level, partially wooded lot, with frequent wildlife sightings. Near the Kettle Moraine State Forest, adventure and relaxation await with ten spring-fed lakes within a ten-minute drive.

    Frank Adashun Adashun Jones Real Estate

    Lt2 Happy Hollow Rd, Osceola, WI 54020
  • 908 Martys Way, Osceola, WI 54020
    908 Martys Way, Osceola, WI 54020
    908 Martys Way, Osceola, WI 54020
    /44

    $415,000

    Sold Aug 03, 2026

    908 Martys Way, Osceola, WI 54020

    • 4 Beds
    • 3 Baths
    • 2,749 Sq Ft
    • Built 1996

    Last Sold Summary

    • 2% Below List Price
    • $151/SF
    • 59 Days On Market

    Current Estimated Value $401,961

    Last Listing Agent Jean Lundgren Keller Williams Integrity WI/MN

    908 Martys Way, Osceola, WI 54020
    • 897 Maple Dr, Osceola, WI 54020
      897 Maple Dr, Osceola, WI 54020
      897 Maple Dr, Osceola, WI 54020
      /16

      Est $296,139

      Not Listed For Sale

      897 Maple Dr, Osceola, WI 54020

      • 2 Beds
      • 2 Baths
      • 1,631 Sq Ft
      • Built 1980
      897 Maple Dr, Osceola, WI 54020

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Alyssa Auten Real Broker, LLC

  • Lt4 Helen Ln, Osceola, WI 53010
    Lt4 Helen Ln, Osceola, WI 53010
    Lt4 Helen Ln, Osceola, WI 53010
    /11

    $84,900

    • Land
    • 1.92 Acres
    • $44,219 per Acre

    Lt4 Helen Ln, Osceola, WI 53010

    Build your dream home now or later, with your choice of builder. Choose the address now in the beautiful Oak Ridge Estates subdivision. Located in the desirable Kettle Moraine area close to several lakes & trails. Minutes away from 45 and 41 for easy travel. Minimal subdivision restrictions apply. A beautiful place to call your own! Perk tests included.

    Sarah Voss Adashun Jones Real Estate

    Lt4 Helen Ln, Osceola, WI 53010
  • 301 Ladd Ln, Osceola, WI 54020
    301 Ladd Ln, Osceola, WI 54020
    /2

    $30,000

    Sold Jun 12, 2026

    301 Ladd Ln, Osceola, WI 54020

    • Land
    • 4,356 Sq Ft
    • $300,000 per Acre

    Last Sold Summary

    • 0 Days On Market

    Current Estimated Value $249,000

    Last Listing Agent Michael Muske RE/MAX Synergy

    301 Ladd Ln, Osceola, WI 54020
    • 806 Oak Ridge Dr, Osceola, WI 54020
      806 Oak Ridge Dr, Osceola, WI 54020
      806 Oak Ridge Dr, Osceola, WI 54020
      /28

      Est $270,610

      Not Listed For Sale

      806 Oak Ridge Dr, Osceola, WI 54020

      • 3 Beds
      • 2 Baths
      • 1,684 Sq Ft
      • Built 1973
      806 Oak Ridge Dr, Osceola, WI 54020

      Last Sold Summary

      • 101 Days On Market

      Last Listing Agent Kyle Hinrichs RE/MAX Team 1 Realty

  • 0 Happy Hollow Rd Unit 50315018, Osceola, WI 53010
    0 Happy Hollow Rd Unit 50315018, Osceola, WI 53010
    0 Happy Hollow Rd Unit 50315018, Osceola, WI 53010
    /12

    $149,900

    • Land
    • 6 Acres
    • $24,983 per Acre

    0 Happy Hollow Rd Unit 50315018, Osceola, WI 53010

    Discover the perfect canvas for your dream home on a sprawling 6.0 acre lot, nestled in the tranquil embrace of nature. Create a private oasis on this level, partially wooded lot, with frequent wildlife sightings. Near the Kettle Moraine State Forest, adventure and relaxation await with ten spring-fed lakes within a ten-minute drive. Signature Homes by Adashun Jones is the preferred builder, but

    Frank Adashun Adashun Jones, Inc.

    0 Happy Hollow Rd Unit 50315018, Osceola, WI 53010
  • 618 Nokomis Dr, Osceola, WI 54020
    618 Nokomis Dr, Osceola, WI 54020
    618 Nokomis Dr, Osceola, WI 54020
    /33

    $333,000

    Sold Sep 26, 2025

    618 Nokomis Dr, Osceola, WI 54020

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Built 1988

    Last Sold Summary

    • 5% Below List Price
    • $222/SF
    • 5 Days On Market

    Current Estimated Value $365,397

    Last Listing Agent Cory Vanover Keller Williams Realty Diversified

    618 Nokomis Dr, Osceola, WI 54020
    • 611 N Cascade St, Osceola, WI 54020
      611 N Cascade St, Osceola, WI 54020
      611 N Cascade St, Osceola, WI 54020
      /28

      Est $292,814

      Not Listed For Sale

      611 N Cascade St, Osceola, WI 54020

      • 3 Beds
      • 2 Baths
      • 1,839 Sq Ft
      • Built 1880
      611 N Cascade St, Osceola, WI 54020

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Bridgette Anderson Edina Realty, Inc.

  • 1898 60th Ave, Osceola, WI 54020
    1898 60th Ave, Osceola, WI 54020
    1898 60th Ave, Osceola, WI 54020
    /36

    $989,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 3.5 Baths
    • 3,452 Sq Ft

    1898 60th Ave, Osceola, WI 54020

    Located just 30 minutes from Stillwater, less than 60 minutes from the Twin Cities, you can experience refined Northwoods living in this architecturally distinctive 4-bedroom, 4-bath residence set along the highly sought-after shores of Big Lake. Thoughtfully positioned within a serene and private setting, the home is designed to frame peaceful lake views and convenient lake access from the

    Wanda Wickenhauser White Oaks Real Estate, LLC

    1898 60th Ave, Osceola, WI 54020

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