Winterset, IA Homes

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  /17

  $235,000 Sold Jun 20, 2025

  2430 Highway 169, Winterset, IA 50273

  • Land
  • 35 Acres
  • $6,714 per Acre

  Last Sold Summary

  • 60% Below List Price
  • 333 Days On Market

  Current Estimated Value $228,924

  Last Listing Agent Keith Soldwisch Zealty Home Advisors

  2430 Highway 169, Winterset, IA 50273
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  /20

  Est $229,639 Not Listed For Sale

  506 E Filmore St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,252 Sq Ft
  • Built 1921

  506 E Filmore St, Winterset, IA 50273

  Last Sold Summary

  • 9% Above List Price
  • $168/SF
  • 118 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Richard Hudnut RE/MAX
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  /12

  $220,000

  • 2 Beds
  • 1 Bath
  • 1,031 Sq Ft

  405 W Madison St, Winterset, IA 50273

  Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower with tile surround and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet

  Alyssa Tadlock Madison County Realty

  405 W Madison St, Winterset, IA 50273
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  /21

  $180,000 Sold Nov 25, 2025

  315 S 5th Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $161/SF
  • 41 Days On Market

  Current Estimated Value $199,484

  Last Listing Agent Dustin Crawford Iowa Home & Land Realty

  315 S 5th Ave, Winterset, IA 50273
• 

  

  

  /18

  Est $222,368 Not Listed For Sale

  510 E Filmore St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1910

  510 E Filmore St, Winterset, IA 50273

  Last Sold Summary

  • 7% Above List Price
  • $167/SF
  • 15 Days On Market

  Last Sold Price $208,000

  Last Listing Agent Dan Vierling Iowa Realty Mills Crossing
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  /35

  $475,000

  • Land
  • 3.9 Acres
  • $121,795 per Acre

  1806 N 8th Ave, Winterset, IA 50273

  Discover peaceful country living just steps from Winterset’s city limits with this beautifully updated acreage. The property is exceptionally neat and well-kept, offering the perfect blend of rural charm and modern convenience.The home features several modern upgrades. Inside, enjoy a a beautiful kitchen with farmhouse charm, quaint dining & living areas, 4 bedrooms and 2 baths.The barn is

  Sarah Cowman Homefront Real Estate, LLC

  1806 N 8th Ave, Winterset, IA 50273
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  /34

  $485,000 Sold Nov 26, 2025

  2340 Holliwell Bridge Rd, Winterset, IA 50273

  • Land
  • 60 Acres
  • $8,083 per Acre

  Last Sold Summary

  • 2% Below List Price
  • 22 Days On Market

  Last Listing Agent Chris Wearmouth Kiloterra

  2340 Holliwell Bridge Rd, Winterset, IA 50273
• 

  

  /29

  Est $266,678 Not Listed For Sale

  311 E Filmore St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 946 Sq Ft
  • Built 1997

  311 E Filmore St, Winterset, IA 50273

  Last Sold Summary

  • 6% Above List Price
  • $266/SF
  • 228 Days On Market

  Last Sold Price $252,000

  Last Listing Agent Ian Sparks Homefront Real Estate, LLC
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  /7

  $250,000

  • Land
  • 5.1 Acres
  • $49,020 per Acre

  2269 205th Ln, Winterset, IA 50273

  Introducing Five Iron Farms - Madison County's newest acreage subdivision. Five Iron Farms offers the best of both world: located in the city limits with city services, but also situated on 3+acres surrounded by farm ground with great views of the countryside. Located on a hard surface road and just down the road from Lakeview Country Club. Bring your own builder. A good reference address to use

  Jennifer Stover Madison County Realty

  2269 205th Ln, Winterset, IA 50273
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  /9

  $213,000 Sold Nov 17, 2025

  413 E Madison St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,031 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $207/SF
  • 183 Days On Market

  Last Listing Agent Alyssa Tadlock Madison County Realty

  413 E Madison St, Winterset, IA 50273
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  /20

  Est $188,549 Not Listed For Sale

  306 E Buchanan St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 986 Sq Ft
  • Built 1880

  306 E Buchanan St, Winterset, IA 50273

  Last Sold Summary

  • 11% Above List Price
  • $172/SF
  • 3 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /18

  $223,000 Pending

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  1221 W Washington St, Winterset, IA 50273

  This super sweet ranch home makes a great starter home. The covered front porch is a great way to relax on the hot summer days. The first floor features a spacious kitchen, comfortable living room, 2 generous sized bedrooms and an updated full bath. The full basement is open and ready finish. The attached garage is heated and has access to the fenced backyard. The backyard features a large patio

  Jennifer Stover Madison County Realty

  1221 W Washington St, Winterset, IA 50273
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  /7

  $159,200 Sold Sep 26, 2025

  Lot 8 114th Ct, Winterset, IA 50273

  • Land
  • 3.02 Acres
  • $52,715 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 307 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 8 114th Ct, Winterset, IA 50273
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  /15

  Est $218,657 Not Listed For Sale

  423 E Benton St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1973

  423 E Benton St, Winterset, IA 50273

  Last Sold Summary

  • 2% Above List Price
  • $213/SF
  • 4 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Robert Duff Covered Bridge Realty
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  /28

  $274,900 Pending

  • 3 Beds
  • 2 Baths
  • 864 Sq Ft

  1509 W South St, Winterset, IA 50273

  Move-in ready and full of charm! This well-cared-for, one owner 3-bedroom, 2-bath home sits in a quiet cul-de-sac and offers comfort and convenience throughout. The kitchen is bright and cheery and comes fully equipped with appliances, plus the washer and dryer are included. Enjoy a spacious basement family room—perfect for entertaining or relaxing—and step out onto the deck overlooking a large,

  Sarah Cowman Homefront Real Estate, LLC

  1509 W South St, Winterset, IA 50273
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  /35

  $580,000 Sold Aug 20, 2025

  926 S 9th Ave, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,987 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $292/SF
  • 65 Days On Market

  Current Estimated Value $605,580

  Last Listing Agent Jennifer Stover Madison County Realty

  926 S 9th Ave, Winterset, IA 50273
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  /19

  Est $182,019 Not Listed For Sale

  715 N 5th St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1999

  715 N 5th St, Winterset, IA 50273

  Last Sold Summary

  • 23% Above List Price
  • $102/SF
  • 10 Days On Market

  Last Sold Price $148,000

  Last Listing Agent Robert Duff Covered Bridge Realty
• 

  

  /18

  $175,000

  • Land
  • 7.14 Acres
  • $24,510 per Acre

  2368 Saint Charles Rd, Winterset, IA 50273

  BRING YOUR OWN BUILDER!!! This 7.14 acres is located right off the St Charles pavement, offering convenience and gorgeous fall views. Schedule a showing today!

  Rachel Eller Summerset Realty

  2368 Saint Charles Rd, Winterset, IA 50273
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  /16

  $199,900 Sold Nov 17, 2025

  520 W Madison St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • Built 2022

  Last Sold Summary

  • 7% Below List Price
  • $194/SF
  • 59 Days On Market

  Last Listing Agent Nicholas Scar Iowa Realty Mills Crossing

  520 W Madison St, Winterset, IA 50273
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  /25

  Est $232,054 Not Listed For Sale

  508 E Lane St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • Built 1998

  508 E Lane St, Winterset, IA 50273

  Last Sold Summary

  • 1% Above List Price
  • $211/SF
  • 60 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Robert Duff Covered Bridge Realty
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  /35

  $825,000 Pending

  • Land
  • 5.67 Acres
  • $145,503 per Acre

  112 S 16th Ave, Winterset, IA 50273

  Don’t miss this one-of-a-kind opportunity to own a private 5+acreage right in town. A picturesque, tree-lined driveway welcomes you to a custom-built totally renovated two-story home surrounded by park-like scenery. With nearly 4,000 sq. ft. of finished living space, this 4-bedroom (plus 2 non conforming) 4-bathroom home offers room to spread out and entertain in style. The upper level features a

  Sarah Cowman Homefront Real Estate, LLC

  112 S 16th Ave, Winterset, IA 50273
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  /29

  $352,500 Sold Feb 02, 2026

  309 N 15th Ave, Winterset, IA 50273

  • 5 Beds
  • 4 Baths
  • 2,110 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Below List Price
  • $167/SF
  • 76 Days On Market

  Current Estimated Value $360,690

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  309 N 15th Ave, Winterset, IA 50273
• 

  

  /26

  Est $240,261 Not Listed For Sale

  622 W Fremont St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1954

  622 W Fremont St, Winterset, IA 50273

  Last Sold Summary

  • 6% Above List Price
  • $176/SF
  • 167 Days On Market

  Last Sold Price $227,500

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /21

  $177,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,222 Sq Ft

  601 E Green St, Winterset, IA 50273

  This beautifully updated 3-bedroom, 1-bath farmhouse at 601 E Green St offers 1,222 sq ft of thoughtfully designed living space. Full of character, the home features an eat-in kitchen, a cozy living room with plenty of natural light, and a bonus room that can easily serve as an office or an extra bedroom. The updated bathroom and fresh flooring throughout the main level add modern convenience.

  Theodore Craig Developers Realty Group LLC

  601 E Green St, Winterset, IA 50273
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  /31

  $187,500 Sold Mar 19, 2026

  501 W Hutchings St, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 988 Sq Ft
  • Built 1963

  Last Sold Summary

  • 13% Below List Price
  • $190/SF
  • 100 Days On Market

  Current Estimated Value $199,205

  Last Listing Agent Krymsin Graf Iowa Realty Ankeny

  501 W Hutchings St, Winterset, IA 50273
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  /12

  Not Listed For Sale

  602 S 2nd St, Winterset, IA 50273

  • Studio
  • 4 Baths
  • 3,600 Sq Ft
  • Built 1998

  602 S 2nd St, Winterset, IA 50273

  Last Sold Summary

  • $77/SF
  • 51 Days On Market

  Last Sold Price $276,000

  Last Listing Agent Toni Tindle Covered Bridge Realty
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  /34

  $349,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,833 Sq Ft

  724 W Buchanan St, Winterset, IA 50273

  Completely renovated 4-bedroom, 2-bath home featuring extensive interior and exterior improvements, along with major structural upgrades that provide long-term peace of mind. Thoughtfully updated from top to bottom, the home offers all new flooring throughout, creating a seamless and modern feel across the main living areas, bedrooms, and finished basement. The bathrooms have been fully remodeled

  Ben Flurey A.I.M. Real Estate & Consultin

  724 W Buchanan St, Winterset, IA 50273
• 

  

  /27

  $204,000 Sold Nov 20, 2025

  202 S 7th Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1953

  Last Sold Summary

  • 3% Below List Price
  • $194/SF
  • 48 Days On Market

  Current Estimated Value $198,296

  Last Listing Agent Tiffany Ehler Boutique Real Estate

  202 S 7th Ave, Winterset, IA 50273
• 

  

  /23

  Est $311,690 Not Listed For Sale

  818 W Washington St, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft
  • Built 2005

  818 W Washington St, Winterset, IA 50273

  Last Sold Summary

  • 16% Above List Price
  • $167/SF
  • 33 Days On Market

  Last Sold Price $268,000

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
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  /7

  $149,000

  • Land
  • 2.93 Acres
  • $50,853 per Acre

  Lot 35 Limestone Ct, Winterset, IA 50273

  Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a

  Julie Baudler RE/MAX Concepts

  Lot 35 Limestone Ct, Winterset, IA 50273
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  /29

  $215,000 Sold Jun 26, 2025

  315 W Washington St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,673 Sq Ft
  • Built 1944

  Last Sold Summary

  • 19% Below List Price
  • $129/SF
  • 27 Days On Market

  Current Estimated Value $236,982

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  315 W Washington St, Winterset, IA 50273
• 

  

  /20

  Est $214,772 Not Listed For Sale

  824 S 4th Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Built 1937

  824 S 4th Ave, Winterset, IA 50273

  Last Sold Summary

  • 8% Above List Price
  • $175/SF
  • 41 Days On Market

  Last Sold Price $198,000

  Last Listing Agent Brady Jackson Iowa Realty South
• 

  

  /35

  $349,900

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

  2197 175th Ct, Winterset, IA 50273

  Want to own a slice of Heaven?! This is it! Fully renovated acreage just off pavement about 3 miles north of charming and growing Winterset and about 7 miles south of DeSoto and I80. Spacious ranch alongside the North River with stunning finishings. Open concept at its finest with vaulted ceilings and daylight everywhere you look! Incredible kitchen that you'll want to show off as you host all

  Ambria Vogt RE/MAX Precision

  2197 175th Ct, Winterset, IA 50273
• 

  

  /23

  $128,000 Sold Dec 30, 2025

  516 W Summit St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1890

  Last Sold Summary

  • 25% Below List Price
  • $107/SF
  • 95 Days On Market

  Last Listing Agent Betsy Breeding Realty ONE Group Impact

  516 W Summit St, Winterset, IA 50273
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  /32

  Est $242,896 Not Listed For Sale

  814 S 4th Ave, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1974

  814 S 4th Ave, Winterset, IA 50273

  Last Sold Summary

  • 2% Below List Price
  • $247/SF
  • 13 Days On Market

  Last Sold Price $248,500

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
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  /7

  $240,000

  • Land
  • 4.19 Acres
  • $57,279 per Acre

  Lot 17 114th Ct, Winterset, IA 50273

  Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a

  Julie Baudler RE/MAX Concepts

  Lot 17 114th Ct, Winterset, IA 50273
• 

  

  /31

  $477,500 Sold Aug 01, 2025

  519 W Mills St, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,597 Sq Ft
  • Built 2023

  Last Sold Summary

  • 2% Below List Price
  • $299/SF
  • 23 Days On Market

  Current Estimated Value $486,104

  Last Listing Agent Renee Dunkel Century 21 Signature

  519 W Mills St, Winterset, IA 50273
• 

  

  /25

  Est $292,314 Not Listed For Sale

  517 W Short St, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1982

  517 W Short St, Winterset, IA 50273

  Last Sold Summary

  • 9% Above List Price
  • $176/SF
  • 126 Days On Market

  Last Sold Price $267,500

  Last Listing Agent Jennifer Stover Madison County Realty
• 

  

  /35

  $340,000

  • 5 Beds
  • 2.5 Baths
  • 2,217 Sq Ft

  621 W Jefferson St, Winterset, IA 50273

  Step into timeless charm with this deceptively spacious 1903 home, perfectly situated on a corner lot along the picturesque, tree-lined W. Jefferson Street—just blocks from the square in Winterset. From the moment you arrive, the inviting front porch sets the tone for relaxed mornings, evening conversations, and a true sense of home. Inside, you’ll find the perfect blend of character and modern

  Jennifer Stover Madison County Realty

  621 W Jefferson St, Winterset, IA 50273
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  /32

  $315,000 Sold Jan 27, 2026

  1541 Nature Ct, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $216/SF
  • 47 Days On Market

  Current Estimated Value $317,677

  Last Listing Agent Elizabeth Gordon Realty ONE Group Impact

  1541 Nature Ct, Winterset, IA 50273

Showing Results 161 - 200, Page 5 of 18