Osceola, WI Homes

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  /106

  $998,000

  $202K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,452 Sq Ft

  1898 60th Ave, Osceola, WI 54020

  Experience refined Northwoods living in this impressive 4-bed, 4-bath log home on much desired Big Lake. Beautifully designed home set in a serene and private setting, the home captures peaceful lake view and lake access from the front of the home and a beautiful wooded backdrop in the back, creating the perfect balance of scenery and seclusion. Inside, you'll find spacious living areas designed

  Wanda Wickenhauser White Oaks Real Estate, LLC

  1898 60th Ave, 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 $215,082

  Last Listing Agent Jennifer Groff Real Broker, LLC

  303A 235th St, Osceola, WI 54020
• 

  

  

  /27

  Est $267,731

  Not Listed For Sale

  430 Tony St, Osceola, WI 54020

  • 2 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • Built 2000

  430 Tony St, Osceola, WI 54020

  Last Sold Summary

  • 24 Days On Market
• 

  

  

  /13

  $315,000

  New Construction $10K PRICE INCREASE

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

  330 Mill 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

  330 Mill St, Osceola, WI 54020
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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 $586,896

  Last Listing Agent Jamie Fahrenkrug EXP Realty, LLC

  21 279th St, Osceola, WI 54020
• 

  /2

  Est $276,373

  Not Listed For Sale

  708 Chieftain St, Osceola, WI 54020

  • 2 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1920

  708 Chieftain St, Osceola, WI 54020
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  /66

  $995,000

  • 1 Bed
  • 2 Baths
  • 1,895 Sq Ft

  1984 35th Ave, Osceola, WI 54020

  Nestled on nearly 40 acres, this country property blends vast views with mature hardwoods and a network of trails through the woods. The single-level home sits back from the road for privacy and features natural hardwood floors and an open kitchen centered around a large island. A den and a sitting room flank the kitchen, while a spacious living room with a gas fireplace provides a comfortable

  Kyle Hinrichs RE/MAX Team 1 Realty

  1984 35th Ave, Osceola, WI 54020
• 

  

  /17

  $399,900

  Sold Mar 13, 2026

  2383 84th Ave, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Built 2025

  Last Sold Summary

  • $308/SF
  • 120 Days On Market

  Current Estimated Value $407,915

  Last Listing Agent Jennifer Kling A Hometown Realty

  2383 84th Ave, Osceola, WI 54020
• 

  

  /43

  Est $254,616

  Not Listed For Sale

  602 N Cascade St, Osceola, WI 54020

  • 5 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • Built 1850

  602 N Cascade St, Osceola, WI 54020

  Last Sold Summary

  • 54 Days On Market
• 

  

  /46

  $475,000

  • 5 Beds
  • 2 Baths
  • 1,770 Sq Ft

  2416 20th Ave, Osceola, WI 54020

  Experience the best of country living on this beautifully updated 10-acre hobby farm just outside Osceola. Surrounded by peaceful farmland and expansive views, this property offers the perfect blend of privacy, modern comfort, and the freedom to enjoy the lifestyle you’ve been looking for. Whether your vision includes gardening, raising animals, outdoor recreation, a workshop, or simply relaxing

  Ryan Bretzel RE/MAX Results

  2416 20th Ave, Osceola, WI 54020
• 

  

  /17

  $350,000

  Sold Apr 17, 2026

  2523 40th Ave, Osceola, WI 54020

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $321/SF
  • 55 Days On Market

  Current Estimated Value $350,144

  2523 40th Ave, Osceola, WI 54020
• 

  /2

  Est $249,580

  Not Listed For Sale

  709 N Cascade St, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft
  • Built 1915

  709 N Cascade St, Osceola, WI 54020
• 

  

  /11

  $84,900

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

  0 Helen Ln Unit 50298326, 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 50298326, Osceola, WI 53010
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  /66

  $700,000

  Sold Jul 22, 2025

  840 250th St, Osceola, WI 54020

  • 4 Beds
  • 3.5 Baths
  • 4,094 Sq Ft
  • Built 2000

  Last Sold Summary

  • $171/SF
  • 53 Days On Market

  Current Estimated Value $766,921

  Last Listing Agent Dawn Bell Realty ONE Group Choice

  840 250th St, Osceola, WI 54020
• 

  

  /11

  Est $311,036

  Not Listed For Sale

  715 N Cascade St, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 1900

  715 N Cascade St, Osceola, WI 54020

  Last Sold Summary

  • 159 Days On Market
• 

  

  /51

  $759,000

  • 4 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  619 Nokomis Dr, Osceola, WI 54020

  Located on Big Lake in Osceola, this four-bedroom, three-bath home offers a modern interior with extensive updates and direct access to one of the area’s connected lake systems. Big Lake is part of a three-lake chain that links Big Lake, Round Lake, and Church Pine Lake, giving owners additional room to explore. fish, paddle, or spend the day on the water. The lake is known for its natural

  Katherine Matzek Keller Williams Premier Realty

  619 Nokomis Dr, Osceola, WI 54020
• 

  

  /25

  $293,000

  Sold Jun 30, 2026

  440 Tony St, Osceola, WI 54020

  • 2 Beds
  • 2 Baths
  • 1,441 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $203/SF
  • 21 Days On Market

  Current Estimated Value $296,276

  Last Listing Agent Melissa Jones Century 21 Affiliated

  440 Tony St, Osceola, WI 54020
• 

  /2

  Est $241,171

  Not Listed For Sale

  717 N Cascade St, Osceola, WI 54020

  • 3 Beds
  • 1 Bath
  • 1,504 Sq Ft
  • Built 1900

  717 N Cascade St, Osceola, WI 54020
• 

  

  /11

  $89,900

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

  Lt3B 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

  Lt3B Helen Ln, Osceola, WI 53010
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  /16

  $129,000

  Sold May 11, 2026

  Lot 7 Big Lake Dr, Osceola, WI 54020

  • Land
  • 4.31 Acres
  • $29,930 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 25 Days On Market

  Last Listing Agent David Strassman Riverbend Realty Group, LLC

  Lot 7 Big Lake Dr, Osceola, WI 54020
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  /36

  Est $263,606

  Not Listed For Sale

  907 N Cascade St, Osceola, WI 54020

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Built 1958

  907 N Cascade St, Osceola, WI 54020

  Last Sold Summary

  • 20 Days On Market
• 

  

  /42

  $549,900

  • 4 Beds
  • 3 Baths
  • 3,121 Sq Ft

  729 220th St, Osceola, WI 54020

  This 4-bed, 3-bath home is set on nearly 2.5 acres and offers a thoughtful layout with plenty of room to spread out, both inside and out. Inside you'll find beautiful hardwood floors, an abundance of natural light, and an updated kitchen that's ready for everything from busy mornings to holiday gatherings. The cozy living room fireplace creates a warm and welcoming focal point, while charming

  Jacob Rivard Red Key Realty

  729 220th St, Osceola, WI 54020
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  /33

  $241,500

  Sold May 12, 2026

  414 3rd Ave E, Osceola, WI 54020

  • 2 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Above List Price
  • $171/SF
  • 21 Days On Market

  Current Estimated Value $240,834

  Last Listing Agent Jean Lundgren Keller Williams Integrity WI/MN

  414 3rd Ave E, Osceola, WI 54020
• 

  

  /36

  Est $400,705

  Not Listed For Sale

  403 8th Ave E, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 1,980 Sq Ft
  • Built 1940

  403 8th Ave E, Osceola, WI 54020

  Last Sold Summary

  • 20 Days On Market
• 

  

  /27

  $417,000

  • 4 Beds
  • 3 Baths
  • 2,640 Sq Ft

  2538 86th Ave, Osceola, WI 54020

  Nestled on a beautiful rural setting of 1.7 acres, this spacious 4 bedroom, 3 bath home offers the perfect blend of privacy, comfort, and room to grow. Enjoy peaceful country views while being part of a well-established neighborhood. Inside, you'll find flexible living spaces designed for today's lifestyle, including multiple areas ideal for home offices, hobby rooms, workout space, or a game

  Jackie Kumm Edina Realty, Inc.

  2538 86th Ave, Osceola, WI 54020
• 

  

  /25

  $255,000

  Sold Nov 21, 2025

  701 N Cascade St, Osceola, WI 54020

  • 4 Beds
  • 1.5 Baths
  • 2,245 Sq Ft
  • Built 1960

  Last Sold Summary

  • $114/SF
  • 58 Days On Market

  Current Estimated Value $296,049

  Last Listing Agent Chelsea Kruse Saphire Realty

  701 N Cascade St, Osceola, WI 54020
• 

  

  /30

  Est $276,578

  Not Listed For Sale

  409 8th Ave E, Osceola, WI 54020

  • 3 Beds
  • 2 Baths
  • 1,860 Sq Ft
  • Built 1985

  409 8th Ave E, Osceola, WI 54020

  Last Sold Summary

  • 51 Days On Market
• 

  

  /88

  $525,000

  • 3 Beds
  • 3 Baths
  • 2,269 Sq Ft

  2485 50th Ave, Osceola, WI 54020

  Escape to the peace and privacy of country living on this beautiful 2.41-acre property! Surrounded by nature yet conveniently located for an easy commute, this inviting home offers the perfect blend of comfort, character, and functionality. The charming log-sided front exterior and welcoming porch set the stage for what's inside. The open-concept floor plan features vaulted ceilings, natural

  Tony Johnson Edina Realty, Inc.

  2485 50th Ave, Osceola, WI 54020
• 

  $157,500

  Sold Mar 06, 2026

  Lt1 Happy Hollow Rd, Osceola, WI 54020

  • Land
  • 5.28 Acres
  • $29,830 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 123 Days On Market

  Last Listing Agent Frank Adashun Adashun Jones Real Estate

  Lt1 Happy Hollow Rd, Osceola, WI 54020
• 

  

  /25

  Est $321,986

  Not Listed For Sale

  516 Eric Dr, Osceola, WI 54020

  • 4 Beds
  • 2 Baths
  • 1,930 Sq Ft
  • Built 1977

  516 Eric Dr, Osceola, WI 54020

  Last Sold Summary

  • 16 Days On Market
• 

  

  /27

  $284,900

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  344 Paulsen Lake Ct, Osceola, WI 54020

  Year-round lake home or cabin on Paulsen lake. Fully remodeled in 2006 including septic and addition of two spacious bedrooms. Water heater and roof new in 2017. Enjoy the views from the top deck of your boat house or backyard deck surrounded by natures treasures. Fire pit, sauna, boat house, dock and manageable size lake home are great perks of this property!

  Vanessa Ross Northern Realty Co.

  344 Paulsen Lake Ct, Osceola, WI 54020
• 

  /2

  $422,650

  Sold Aug 21, 2025

  0 230th St, Osceola, WI 54020

  • Land
  • 56.5 Acres
  • $7,481 per Acre

  Last Sold Summary

  • 42,264,900% Above List Price
  • 77 Days On Market

  Last Listing Agent Jerry Bates Hansen Real Estate Group

  0 230th St, Osceola, WI 54020
• 

  

  /39

  Est $316,039

  Not Listed For Sale

  502 Gerald St, Osceola, WI 54020

  • 3 Beds
  • 1.5 Baths
  • 2,178 Sq Ft
  • Built 1968

  502 Gerald St, Osceola, WI 54020

  Last Sold Summary

  • 70 Days On Market
• 

  

  /23

  $383,000

  $8K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft

  2192 90th Ave, Osceola, WI 54020

  More photos coming soon. Move-in ready rambler on a 1-acre lot! This meticulously cared-for home is located in a nice, quiet setting with room to stretch. The laundry room is conveniently located on the main level next to the bedrooms. Two bedrooms are located upstairs. New Bosch stainless steel appliances are still under warranty. Mechanicals were updated in 2025 and are also under warranty. The

  Laura Baker Apple River Realty LLC

  2192 90th Ave, Osceola, WI 54020
• 

  

  /28

  $405,000

  Sold Jun 18, 2026

  730 170th St, Osceola, WI 54020

  • 5 Beds
  • 2 Baths
  • 2,570 Sq Ft
  • Built 1910

  Last Sold Summary

  • 9% Below List Price
  • $158/SF
  • 93 Days On Market

  Current Estimated Value $433,547

  Last Listing Agent Greg Koshiol Property Executives Realty

  730 170th St, Osceola, WI 54020
• 

  /2

  Est $282,583

  Not Listed For Sale

  508 Gerald St, Osceola, WI 54020

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • Built 1968

  508 Gerald St, Osceola, WI 54020
• 

  

  /40

  $950,000

  $50K PRICE INCREASE Pending

  • 3 Beds
  • 4 Baths
  • 3,040 Sq Ft

  901 N Cascade St, Osceola, WI 54020

  Charming and peaceful 1930's St Croix riverfront property featuring a long private drive, a primary big house and a guest cottage. 6.59 acres, with 215 feet of owned river frontage. New tram and a walkway to the river. Long private driveway lined with White Pine, Maple, Cedar and Oak. The Great Room with stone fireplace and large panoramic windows. Recently re-designed kitchen with a large

  Ralph Peterson Coldwell Banker Realty

  901 N Cascade St, Osceola, WI 54020
• 

  

  /40

  $640,000

  Sold Jul 25, 2025

  411C Ridge Rd, Osceola, WI 54020

  • 4 Beds
  • 4.5 Baths
  • 3,914 Sq Ft
  • Built 2004

  Last Sold Summary

  • $164/SF
  • 93 Days On Market

  Current Estimated Value $622,999

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

  411C Ridge Rd, Osceola, WI 54020
• 

  /2

  Est $263,699

  Not Listed For Sale

  403 Caroll St, Osceola, WI 54020

  • 3 Beds
  • 1 Bath
  • 1,512 Sq Ft
  • Built 1963

  403 Caroll St, Osceola, WI 54020
• 

  

  /11

  $399,000

  • Land
  • 28,314 Sq Ft
  • $613,846 per Acre

  254 S Cascade, Osceola, WI 54020

  Ben Bruno The Terrace Group

  254 S Cascade, Osceola, WI 54020

Showing Results 81 - 120, Page 3 of 18