Winterset, IA Homes

• 

  

  

  /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
• 

  

  

  /35

  Est $319,484

  Not Listed For Sale

  522 N 7th Ave, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 1,792 Sq Ft
  • Built 1915

  522 N 7th Ave, Winterset, IA 50273

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  

  /7

  $240,000

  $60K PRICE DROP

  • Land
  • 6.98 Acres
  • $34,384 per Acre

  Lot 16 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 16 114th Ct, Winterset, IA 50273
• 

  

  

  /7

  $420,000

  Sold May 19, 2026

  122 E Jefferson St Unit 1-6, Winterset, IA 50273

  • Studio
  • 5,952 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Below List Price
  • $71/SF
  • 4 Days On Market

  Last Listing Agent Bob Ruby Ruby Realty Group LLC

  122 E Jefferson St Unit 1-6, Winterset, IA 50273
• 

  

  

  /25

  Est $211,510

  Not Listed For Sale

  809 E Benton St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,816 Sq Ft
  • Built 1890

  809 E Benton St, Winterset, IA 50273

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Cody Bilyeu RE/MAX Concepts
• 

  

  /19

  $215,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 848 Sq Ft

  121 E Benton St, Winterset, IA 50273

  If you are looking for a starter home or a nice home to downsize, you need to take a look at this one. This 2 bedroom, 1 bath is handicap accessible, built in 1932 with 848sf, with a living room, dining, hardwood floors and natural woodwork. Included with this home is a full size pool table, bar/chairs. The home has a large garage built in 2004(28x36) with an unfinished attic for additional

  Larry Corkrean Madison County Realty

  121 E Benton St, Winterset, IA 50273
• 

  

  /32

  $330,000

  Sold May 22, 2026

  2817 Carver Rd, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • Built 1993

  Last Sold Summary

  • 13% Below List Price
  • $206/SF
  • 56 Days On Market

  Current Estimated Value $350,494

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  2817 Carver Rd, Winterset, IA 50273
• 

  

  /16

  Est $241,672

  Not Listed For Sale

  602 E Benton St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1974

  602 E Benton St, Winterset, IA 50273

  Last Sold Summary

  • 278 Days On Market

  Last Listing Agent Jamie Adkins RE/MAX Precision
• 

  /2

  $130,000

  • Land
  • 39,204 Sq Ft
  • $144,444 per Acre

  Lot 1 N 4th Ave, Winterset, IA 50273

  New Light Commercial Development. Lots will be ready to build upon in Spring 2025, Street will be in Fall 2024. All utilities to the lots. Great location on north side of Winterset w/ easy access to major highways. Listing agent has ownership in the property.

  Peter Corkrean Madison County Realty

  Lot 1 N 4th Ave, Winterset, IA 50273
• 

  

  /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
• 

  

  /17

  Est $174,349

  Not Listed For Sale

  622 N 7th St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 772 Sq Ft
  • Built 1910

  622 N 7th St, Winterset, IA 50273

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Nicholas Scar Iowa Realty Mills Crossing
• 

  

  /17

  $169,900

  $55K PRICE DROP

  • Land
  • 4.68 Acres
  • $36,303 per Acre

  2215 245 Ln, Winterset, IA 50273

  Beautiful rolling building lot just south of town and on minimal gravel located on a dead end road! This 4.68 acre m/l lot is ready for you to bring your builder and build your dream home! The lot gently rolls to the north for a walk out opportunity and overlooks the neighbor's pristine pond! There will be very minimal covenants (currenty being drawn up by attorney) and the county needs to

  Sarah Cowman Homefront Real Estate, LLC

  2215 245 Ln, Winterset, IA 50273
• 

  

  /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 $364,858

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  309 N 15th Ave, Winterset, IA 50273
• 

  

  /25

  Est $171,555

  Not Listed For Sale

  707 E Buchanan St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,061 Sq Ft
  • Built 1910

  707 E Buchanan St, Winterset, IA 50273

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Jenn Ho Goh GoSynergy Realty
• 

  

  /35

  $325,000

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,470 Sq Ft

  1405 W Jefferson St, Winterset, IA 50273

  Welcome to this well-maintained 4 bedroom, 3 bathroom home offering just under 1,500 square feet of comfortable living space in one of Central Iowa?s most charming communities. This home features a functional layout with spacious living areas, abundant natural light, and plenty of room for both everyday living and entertaining.The main living space offers a warm and inviting feel with an open

  Matt Law RE/MAX Precision

  1405 W Jefferson St, Winterset, IA 50273
• 

  

  /26

  $205,000

  Sold Jun 29, 2026

  406 N 7th St, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft
  • Built 1910

  Last Sold Summary

  • 5% Below List Price
  • $197/SF
  • 9 Days On Market

  Current Estimated Value $210,517

  Last Listing Agent Dakoda Overbeck Iowa Realty Waukee

  406 N 7th St, Winterset, IA 50273
• 

  

  /16

  Est $247,244

  Not Listed For Sale

  908 E Benton St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 796 Sq Ft
  • Built 2006

  908 E Benton St, Winterset, IA 50273

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Tammy Heckart RE/MAX Concepts
• 

  /2

  $2,000,000

  Pending

  • Land
  • 315 Acres
  • $6,349 per Acre

  000 Settler Ave, Winterset, IA 50273

  24-hour sale. Primarily wetlands.

  Heather Helland RE/MAX Precision

  000 Settler Ave, Winterset, IA 50273
• 

  /2

  $658,000

  Sold Jun 15, 2026

  1525 S 4th Ave Unit 2, Winterset, IA 50273

  • 5 Beds
  • 3.5 Baths
  • 2,582 Sq Ft
  • Built 1997

  Last Sold Summary

  • $255/SF
  • 103 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  1525 S 4th Ave Unit 2, Winterset, IA 50273
• 

  

  /20

  Est $221,170

  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

  • 118 Days On Market

  Last Listing Agent Richard Hudnut RE/MAX Concepts
• 

  

  /12

  $206,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,031 Sq Ft

  407 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

  407 W Madison St, Winterset, IA 50273
• 

  

  /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 $193,369

  Last Listing Agent Krymsin Graf Iowa Realty Ankeny

  501 W Hutchings St, Winterset, IA 50273
• 

  

  /18

  Est $227,997

  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

  • 15 Days On Market

  Last Listing Agent Dan Vierling Iowa Realty Mills Crossing
• 

  /2

  $450,000

  • Land
  • 30 Acres
  • $15,000 per Acre

  RR Scott Township None, Winterset, IA 50222

  A great opportunity to add to your existing operation or the perfect acreage to start a small farm, a nice building site or weekend gateway. This is a highly productive farm, all tillable with a CSR 2 rating of 83.

  Patrick Corkrean Madison County Realty

  RR Scott Township None, Winterset, IA 50222
• 

  

  /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 $200,906

  Last Listing Agent Tiffany Ehler Boutique Real Estate

  202 S 7th Ave, Winterset, IA 50273
• 

  

  /18

  Est $300,636

  Not Listed For Sale

  515 E North St, Winterset, IA 50273

  • Studio
  • 2 Baths
  • 995 Sq Ft
  • Built 1994

  515 E North St, Winterset, IA 50273

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Jennifer Stover Madison County Realty
• 

  /2

  $185,000

  • Land
  • 1.14 Acres
  • $161,996 per Acre

  Lot 4 N 4th Ave, Winterset, IA 50273

  New Light Commercial Development. Lots will be ready to be built upon in Spring 2025, road will paved in Fall 2025. All utilities to the lots. Great location for easy access to major highways. Listing agent has ownership in the property.

  Peter Corkrean Madison County Realty

  Lot 4 N 4th Ave, 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
• 

  

  /29

  Est $274,620

  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

  • 228 Days On Market

  Last Listing Agent Ian Sparks Homefront Real Estate, LLC
• 

  

  /31

  $230,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,216 Sq Ft

  1667 195th St, Winterset, IA 50273

  This super cute acreage on just over 3 acres is the affordable hobby farm you have been waiting for! Offering endless possibilities, the property features a cozy 3-bedroom, 2-full-bath home, multiple storage sheds, and a fenced-in pasture on the west side—perfect for horses, cattle, or FFA projects. The highlight for any craftsman or hobbyist is the impressive 30'x48' shop building, providing a

  Ian Sparks Homefront Real Estate, LLC

  1667 195th St, Winterset, IA 50273
• 

  

  /7

  $199,000

  Sold Oct 28, 2025

  Lot 21 112th Ct, Winterset, IA 50273

  • Land
  • 3.37 Acres
  • $59,050 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 326 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 21 112th Ct, Winterset, IA 50273
• 

  

  /15

  Est $215,229

  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

  • 4 Days On Market

  Last Listing Agent Robert Duff Covered Bridge Realty
• 

  

  /34

  $579,900

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,432 Sq Ft

  719 E Washington St, Winterset, IA 50273

  Discover the ultimate "wow factor" in this stunning Winterset property, truly like anything else. It’s been completely rebuilt to marry historic soul with modern luxury. This isn't just a renovation; it’s a turnkey masterpiece designed for entertaining and everyday living; featuring a main-level primary retreat bathed in incredible natural sunlight throughout the home. It includes 3 bedrooms +

  Sarah Cowman Homefront Real Estate, LLC

  719 E Washington St, Winterset, IA 50273
• 

  

  /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 $342,139

  Last Listing Agent Elizabeth Gordon Realty ONE Group Impact

  1541 Nature Ct, Winterset, IA 50273
• 

  

  /25

  Est $227,917

  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

  • 60 Days On Market

  Last Listing Agent Robert Duff Covered Bridge Realty
• 

  

  /34

  $1

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  00 235th St, Winterset, IA 50273

  Madison County, Iowa Land Auction! Presenting the sale of 75.33 surveyed acres m/l of premium recreational land located just southwest of Winterset, Iowa, in Madison County. This unique offering presents an excellent opportunity to purchase quality recreational property, attractive building sites, and a rural acreage in one of Iowa's most desirable counties. The property will be offered in three

  Daran Becker Peoples Company

  00 235th St, Winterset, IA 50273
• 

  

  /3

  $220,000

  Sold Sep 15, 2025

  825 W Fremont St, Winterset, IA 50273

  • 2 Beds
  • 2.5 Baths
  • 1,213 Sq Ft
  • Built 2000

  Last Sold Summary

  • 2% Below List Price
  • $181/SF
  • 3 Days On Market

  Current Estimated Value $218,528

  Last Listing Agent Randall Henry Madison County Realty

  825 W Fremont St, Winterset, IA 50273
• 

  

  /26

  Est $229,693

  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

  • 167 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /29

  $4,938,450

  • Land
  • 451.34 Acres
  • $10,942 per Acre

  0 N River School Rd Unit 745575, Winterset, IA 50273

  We are proud to present the Hogback Farm, an exceptional 451 acre m/l recreational and income-producing property located in the heart of Madison County, Iowa, just a short drive from the Des Moines metro. Tucked into a highly desirable corridor between Winterset and Adel, less than one mile from paved Highway 169, this property offers a rare combination of privacy, natural beauty, and

  Bryan Bergdale Peoples Company

  0 N River School Rd Unit 745575, Winterset, IA 50273
• 

  

  /28

  $250,000

  Sold Jun 16, 2026

  613 E Buchanan St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,878 Sq Ft
  • Built 1890

  Last Sold Summary

  • $133/SF
  • 1 Day On Market

  Current Estimated Value $246,438

  Last Listing Agent Payton Coyle Century 21 Signature

  613 E Buchanan St, Winterset, IA 50273

Showing Results 161 - 200, Page 5 of 18