Osceola, WI Homes

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  $435,000 Sold Oct 15, 2025

  N3049 B & B Ct, Osceola, WI 53010

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft

  Last Sold Summary

  • 9% Above List Price
  • $177/SF
  • 1 Day On Market

  Current Estimated Value $441,837

  Last Listing Agent Becky Bednarek Keller Williams Prestige

  N3049 B & B Ct, Osceola, WI 53010
• 

  Est $328,286 Not Listed For Sale

  700 Deer Path, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 2005

  700 Deer Path, Osceola, WI 54020

  Last Sold Summary

  • 6% Above List Price
  • $175/SF
  • 46 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Jean Lundgren Keller Williams Integrity WI/MN
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  /35

  $284,900

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

  890 Maple Dr, Osceola, WI 54020

  Located in a desirable in-town neighborhood within walking distance to parks, trails, and schools. This well-maintained 4-bedroom, 3-bath walk-out ranch offers comfort, convenience, and space. The beautifully landscaped yard features an inviting backyard patio, garden, pergola, and a deck added just four years ago—perfect for relaxing or entertaining.Inside, enjoy a freshly painted interior,

  Jean Lundgren Keller Williams Integrity WI/MN

  890 Maple Dr, Osceola, WI 54020
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  /73

  $590,000 Sold May 22, 2025

  2379 50th Ave, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 3,262 Sq Ft
  • Built 1988

  Last Sold Summary

  • $181/SF
  • 68 Days On Market

  Current Estimated Value $595,301

  Last Listing Agent Jaclyn Butcher Edina Realty, Inc.

  2379 50th Ave, Osceola, WI 54020
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  /24

  Est $319,645 Not Listed For Sale

  300 Deer Path, Osceola, WI 54020

  • 2 Beds
  • 2 Baths
  • 1,720 Sq Ft
  • Built 2003

  300 Deer Path, Osceola, WI 54020

  Last Sold Summary

  • 3% Above List Price
  • $180/SF
  • 46 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Todd Franck Keller Williams Premier Realty
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  /54

  $549,900 Pending

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

  48 279th St, Osceola, WI 54020

  A retreat in Nature – Secluded, Private 3BD, 3BA home is nestled in 3.8 wooded acres with pond views. This meticulously well-kept home is comfortable with main-level primary living. The ML features wood flooring throughout, fresh paint, maple doors and trim, a large foyer, a kitchen, and a dining room with a patio door to access a deck overlooking the backyard. Enjoy an afternoon relaxing on the

  Michael Germain RE/MAX Team 1 Realty

  48 279th St, Osceola, WI 54020
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  /3

  $296,900 Sold Sep 19, 2025

  340 Mill St, Osceola, WI 54020

  • 2 Beds
  • 1.5 Baths
  • 1,185 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $251/SF
  • 12 Days On Market

  Current Estimated Value $305,345

  Last Listing Agent Candice Mueller RE/MAX Synergy/Osceola

  340 Mill St, Osceola, WI 54020
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  /28

  Est $365,991 Not Listed For Sale

  303 Meadow Lark Ln, Osceola, WI 54020

  • 3 Beds
  • 3.5 Baths
  • 1,797 Sq Ft
  • Built 2003

  303 Meadow Lark Ln, Osceola, WI 54020

  Last Sold Summary

  • 15% Below List Price
  • $239/SF
  • 17 Days On Market

  Last Sold Price $430,000

  Last Listing Agent Leslie Boyea Quorum Enterprises, Inc.
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  /2

  $59,000 Pending

  • Land
  • 1.14 Acres
  • $51,754 per Acre

  Lt12 Red Oak Dr, Osceola, WI 53010

  Elizabeth Augustyn Birchwood Properties LLC

  Lt12 Red Oak Dr, Osceola, WI 53010
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  /73

  $332,700 Sold Jun 06, 2025

  2239 75th Ave Unit M, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 2,520 Sq Ft
  • Built 1977

  Last Sold Summary

  • $132/SF
  • 11 Days On Market

  Current Estimated Value $352,012

  Last Listing Agent Joshua Leonhardt Coldwell Banker Realty

  2239 75th Ave Unit M, Osceola, WI 54020
• 

  Est $377,492 Not Listed For Sale

  406 Smith Ave, Osceola, WI 54020

  • 4 Beds
  • 3 Baths
  • Built 2004

  406 Smith Ave, Osceola, WI 54020

  Last Sold Summary

  • 3% Above List Price
  • 47 Days On Market

  Last Sold Price $365,000

  Last Listing Agent Mary Griesbach Property Executives Realty
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  /74

  $539,900

  • 6,000 Sq Ft

  W498 Elm St, Osceola, WI 53010

  Investment Opportunity in the Heart of the Kettle Moraine ( Dundee ). A church, parsonage, and parking lot all included. Make this beautiful church into your dream business. The church offers a great space, stained glass windows, front entry, & balcony. The LL includes a kitchen and 2 bathrooms. Rent or live in the multi level parsonage with 4 bedrooms, 2.5 Baths, living room, family room, & open

  Sarah Voss Adashun Jones Real Estate

  W498 Elm St, Osceola, WI 53010
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  /27

  $188,000 Sold May 16, 2025

  914 Geiger St, Osceola, WI 54020

  • 3 Beds
  • 1 Bath
  • 865 Sq Ft
  • Built 1953

  Last Sold Summary

  • 4% Below List Price
  • $217/SF
  • 167 Days On Market

  Current Estimated Value $198,321

  Last Listing Agent James Tinman Re/Max Cornerstone

  914 Geiger St, Osceola, WI 54020
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  Est $328,600 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

  Last Sold Summary

  • $195/SF
  • 15 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Jean Lundgren Keller Williams Rlty Integrity*
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  /5

  $249,900 New Construction

  • 2 Beds
  • 1 Bath
  • 834 Sq Ft

  301 Ladd Ln, Osceola, WI 54020

  The Teton Plan. One level living! Experience the joy and ease of owning a NEW home! Located in the appealing neighborhood of Gateway Meadows in the charming river town, Osceola. Other plans/lots to choose from.

  Candice Mueller RE/MAX Synergy

  301 Ladd Ln, Osceola, WI 54020
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  /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 $317,321

  Last Listing Agent Ryan Berner Realty Executives Top Results

  912 Maple Dr, Osceola, WI 54020
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  /24

  Est $337,991 Not Listed For Sale

  501 Delmar Ave, Osceola, WI 54020

  • 4 Beds
  • 2 Baths
  • 2,269 Sq Ft
  • Built 1992

  501 Delmar Ave, Osceola, WI 54020

  Last Sold Summary

  • 9% Above List Price
  • $137/SF
  • 3 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Jennifer Martin Edina Realty, Inc.
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  /40

  $305,000 New Construction

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

  290 Spring St, Osceola, WI 54020

  New Construction! The Princeton B plan: Experience the joy of owning a NEW home. Located in the appealing neighborhood of Gateway Meadows in the charming river town, Osceola. Other plans/lots to choose from.

  Candice Mueller RE/MAX Synergy

  290 Spring St, Osceola, WI 54020
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  /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 $383,901

  Last Listing Agent Michelle Austad EXP Realty, LLC

  881 217th St, Osceola, WI 54020
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  /42

  Est $322,798 Not Listed For Sale

  115 Belmont St, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • Built 1996

  115 Belmont St, Osceola, WI 54020

  Last Sold Summary

  • 9% Above List Price
  • $162/SF
  • 3 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Tracy Shalander LPT Realty, LLC
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  /2

  $249,900

  • 2 Beds
  • 1 Bath

  300 Ladd Ln, Osceola, WI 54020

  One-Level Living! Experience the joy and ease of owning a NEW home! Located in the appealing neighborhood of Gateway Meadows in the charming river town, Osceola. Other plans/lots to choose from.

  Candice Mueller RE/MAX Synergy

  300 Ladd Ln, Osceola, WI 54020
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  /32

  $312,000 Sold Aug 14, 2025

  2293 57th Ave, Osceola, WI 54020

  • 1 Bed
  • 1.5 Baths
  • 576 Sq Ft
  • Built 2019

  Last Sold Summary

  • $542/SF
  • 19 Days On Market

  Current Estimated Value $303,502

  Last Listing Agent Mara Bowman Coldwell Banker Realty

  2293 57th Ave, Osceola, WI 54020
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  /11

  Est $229,925 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

  • 7% Above List Price
  • $173/SF
  • 40 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Jean Lundgren Keller Williams Integrity WI/MN
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  /50

  $565,000 Under Contract

  • 4 Beds
  • 3 Baths

  624 62nd Ave, Osceola, WI 54020

  This 4-bedroom, 3-bathroom log home is the perfect blend of rustic charm and modern comfort. Situated on 1.6 acres of land with mature trees, it offers plenty of outdoor space and privacy. You also have deeded access to Big Lake with a shared dock?ideal for water enthusiasts to enjoy boating, fishing and water sports. Inside the home, you'll love the vaulted open-concept living room, kitchen and

  Tony Johnson Edina Realty, Inc.

  624 62nd Ave, Osceola, WI 54020
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  /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 $427,279

  Last Listing Agent Joshua Leonhardt Coldwell Banker Realty

  106 Prairie Grass Dr, Osceola, WI 54020
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  Est $219,375 Not Listed For Sale

  826 Oak Ct, Osceola, WI 54020

  • 2 Beds
  • 2 Baths
  • Built 1990

  826 Oak Ct, Osceola, WI 54020

  Last Sold Summary

  • 6% Above List Price
  • 21 Days On Market

  Last Sold Price $206,000

  Last Listing Agent Alison Blanchard Compass Realty Group
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  /10

  $159,990

  • Land
  • 261,360 Acres
  • $1 per Acre

  369 240th St, Osceola, WI 54020

  6-Acre Build-Ready Lot with Privacy and Convenience This stunning 6-acre lot offers a perfect blend of nature and readiness for your dream home. With a Certificate of Survey and a completed Soil Evaluation Report, all the groundwork has been done. The potential building site is already cleared, making it ideal for constructing a spacious home. Surrounded by mature trees, the property boasts a

  Michael Giese Century 21 Affiliated

  369 240th St, Osceola, WI 54020
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  /30

  $389,900 Sold Aug 13, 2025

  559 Wisconsin 35, Osceola, WI 54020

  • 4 Beds
  • 1 Bath
  • 1,872 Sq Ft
  • Built 1975

  Last Sold Summary

  • $208/SF
  • 50 Days On Market

  Current Estimated Value $387,859

  Last Listing Agent Melissa Jones Century 21 Affiliated

  559 Wisconsin 35, Osceola, WI 54020
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  /22

  Est $265,585 Not Listed For Sale

  506 Saratoga Ave, Osceola, WI 54020

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1986

  506 Saratoga Ave, Osceola, WI 54020

  Last Sold Summary

  • 11% Above List Price
  • $250/SF
  • 11 Days On Market

  Last Sold Price $239,900

  Last Listing Agent Nathaniel Pettis RE/MAX Advantage Plus
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  /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
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  /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 $332,840

  Last Listing Agent Cory Vanover Keller Williams Realty Diversified

  618 Nokomis Dr, Osceola, WI 54020
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  /19

  Est $283,977 Not Listed For Sale

  109 Hialeah St, Osceola, WI 54020

  • 3 Beds
  • 3 Baths
  • 1,505 Sq Ft
  • Built 1993

  109 Hialeah St, Osceola, WI 54020

  Last Sold Summary

  • 32% Above List Price
  • $143/SF
  • 18 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Jason Lange RE/MAX Results
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  /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
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  $82,000 Sold Jun 27, 2025

  0 Helen Ln Unit 50298323, Osceola, WI 53010

  • Land
  • 1.92 Acres
  • $42,708 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 279 Days On Market

  Last Listing Agent Sarah Voss Adashun Jones, Inc.

  0 Helen Ln Unit 50298323, Osceola, WI 53010
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  Est $336,874 Not Listed For Sale

  922 Circle Ct, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • Built 1989

  922 Circle Ct, Osceola, WI 54020

  Last Sold Summary

  • 4% Above List Price
  • 75 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Jean Lundgren Keller Williams Rlty Integrity*
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  /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
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  /49

  $210,000 Sold Jul 18, 2025

  303A 235th St, Osceola, WI 54020

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1960

  Last Sold Summary

  • $210/SF
  • 5 Days On Market

  Current Estimated Value $206,551

  Last Listing Agent Jennifer Groff Real Broker, LLC

  303A 235th St, Osceola, WI 54020
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  /33

  Est $348,019 Not Listed For Sale

  912 Martys Way, Osceola, WI 54020

  • 5 Beds
  • 1.5 Baths
  • 2,000 Sq Ft
  • Built 1937

  912 Martys Way, Osceola, WI 54020

  Last Sold Summary

  • 4% Above List Price
  • $168/SF
  • 76 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Peggy Weber Keller Williams Integrity WI/MN
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  /11

  $89,900

  • 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
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  /41

  $575,000 Sold Sep 16, 2025

  21 279th St, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft
  • Built 2023

  Last Sold Summary

  • $302/SF
  • 2 Days On Market

  Current Estimated Value $575,168

  Last Listing Agent Jamie Fahrenkrug EXP Realty, LLC

  21 279th St, Osceola, WI 54020

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