Winterset, IA Homes

• 

  

  

  /19

  $162,250

  Sold Jun 23, 2026

  703 W North St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1947

  Last Sold Summary

  • 5% Below List Price
  • $171/SF
  • 20 Days On Market

  Current Estimated Value $157,655

  Last Listing Agent Tina Knox Iowa Realty Mills Crossing

  703 W North St, Winterset, IA 50273
• 

  

  

  /26

  Est $356,303

  Not Listed For Sale

  925 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 2,267 Sq Ft
  • Built 1972

  925 W Jefferson St, Winterset, IA 50273

  Last Sold Summary

  • 1 Day On Market
• 

  

  

  /11

  $210,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,031 Sq Ft

  409 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

  409 W Madison St, Winterset, IA 50273
• 

  

  

  /33

  $647,499

  Sold Mar 27, 2026

  1634 170th St, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,895 Sq Ft
  • Built 2001

  Last Sold Summary

  • 4% Below List Price
  • $342/SF
  • 268 Days On Market

  Current Estimated Value $648,902

  Last Listing Agent Kate Carlson Realty ONE Group Impact

  1634 170th St, Winterset, IA 50273
• 

  

  

  /35

  Est $255,646

  Not Listed For Sale

  901 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 1958

  901 W Jefferson St, Winterset, IA 50273

  Last Sold Summary

  • 11 Days On Market
• 

  

  /23

  $229,900

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,006 Sq Ft

  113 S 3rd St, Winterset, IA 50273

  Move-in ready and totally remodeled 3-bed 2.5-bath ranch! Everything you need is on the main level. This home has been thoughtfully renovated, utilizing every square inch. Walk in, and you will appreciate the large entry way ready for your locker system or bench area. The living room is bright and spacious and is open to the kitchen. The kitchen has nice counter and cabinet space with a pantry

  Sarah Cowman Homefront Real Estate, LLC

  113 S 3rd St, Winterset, IA 50273
• 

  

  /28

  $870,000

  Sold Jan 02, 2026

  2176 148th St, Winterset, IA 50273

  • 4 Beds
  • 2.5 Baths
  • 1,534 Sq Ft
  • Built 2005

  Last Sold Summary

  • 8% Below List Price
  • $567/SF
  • 85 Days On Market

  Current Estimated Value $840,943

  Last Listing Agent Jason Russell Realty ONE Group Impact

  2176 148th St, Winterset, IA 50273
• 

  

  /25

  Est $483,832

  Not Listed For Sale

  614 W Benton St, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 2,595 Sq Ft
  • Built 2001

  614 W Benton St, Winterset, IA 50273

  Last Sold Summary

  • 11 Days On Market
• 

  

  /35

  $350,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  2381 Adair Madison Ave, Winterset, IA 50273

  Discover the perfect blend of country living, outdoor recreation, and modern updates with this exceptional 10-acre hobby farm, located just one mile off Highway 92. Step inside the beautifully updated 3-bedroom, 1-bathroom home featuring a comfortable, flowing floor plan. The heart of the home is a large country kitchen with abundant cabinet space and room for a dining table, which seamlessly

  Ian Sparks Homefront Real Estate, LLC

  2381 Adair Madison Ave, Winterset, IA 50273
• 

  

  /35

  $749,900

  Sold Aug 15, 2025

  4726 Cherrywood Ln, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,742 Sq Ft
  • Built 2016

  Last Sold Summary

  • $430/SF
  • 5 Days On Market

  Current Estimated Value $765,854

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  4726 Cherrywood Ln, Winterset, IA 50273
• 

  

  /20

  Est $251,884

  Not Listed For Sale

  501 W Buchanan St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1963

  501 W Buchanan St, Winterset, IA 50273

  Last Sold Summary

  • 34 Days On Market
• 

  

  /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
• 

  

  /35

  $295,000

  Sold Sep 22, 2025

  522 N 10th St, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,972 Sq Ft
  • Built 1991

  Last Sold Summary

  • 5% Below List Price
  • $150/SF
  • 25 Days On Market

  Current Estimated Value $297,716

  Last Listing Agent Kristen Stehli Real Broker, LLC

  522 N 10th St, Winterset, IA 50273
• 

  

  /28

  Est $271,489

  Not Listed For Sale

  421 W Buchanan St, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,500 Sq Ft
  • Built 1964

  421 W Buchanan St, Winterset, IA 50273

  Last Sold Summary

  • 19 Days On Market
• 

  /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
• 

  

  /7

  $160,000

  Sold Jan 08, 2026

  Lot 23 112th Ct, Winterset, IA 50273

  • Land
  • 3.34 Acres
  • $47,904 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 413 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 23 112th Ct, Winterset, IA 50273
• 

  

  /22

  Est $216,905

  Not Listed For Sale

  618 N 4th Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1970

  618 N 4th Ave, Winterset, IA 50273

  Last Sold Summary

  • 6 Days On Market
• 

  

  /16

  $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
• 

  

  /19

  $210,000

  Sold Feb 27, 2026

  2236 Carver Rd, Winterset, IA 50273

  • 1 Bed
  • 1 Sq Ft
  • Built 2021

  Last Sold Summary

  • 9% Below List Price
  • $210,000/SF
  • 12 Days On Market

  Current Estimated Value $216,261

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  2236 Carver Rd, Winterset, IA 50273
• 

  

  /24

  Est $227,206

  Not Listed For Sale

  1104 W South St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 912 Sq Ft
  • Built 1961

  1104 W South St, Winterset, IA 50273

  Last Sold Summary

  • 58 Days On Market
• 

  

  /35

  $330,000

  $5K 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
• 

  

  /35

  $569,900

  Sold Sep 24, 2025

  1713 Merriam Ct, Winterset, IA 50273

  • 3 Beds
  • 3 Baths
  • 1,493 Sq Ft
  • Built 2017

  Last Sold Summary

  • $382/SF
  • 3 Days On Market

  Current Estimated Value $556,130

  Last Listing Agent Connie Ridgway Iowa Realty Mills Crossing

  1713 Merriam Ct, Winterset, IA 50273
• 

  

  /25

  Est $223,373

  Not Listed For Sale

  1016 W South St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1960

  1016 W South St, Winterset, IA 50273

  Last Sold Summary

  • 4 Days On Market
• 

  /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
• 

  

  /35

  $310,000

  Sold Aug 07, 2025

  522 N 7th Ave, Winterset, IA 50273

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

  Last Sold Summary

  • $173/SF
  • 10 Days On Market

  Current Estimated Value $321,102

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  522 N 7th Ave, Winterset, IA 50273
• 

  

  /31

  Est $292,492

  Not Listed For Sale

  926 W Court Ave, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,387 Sq Ft
  • Built 1959

  926 W Court Ave, Winterset, IA 50273

  Last Sold Summary

  • 25 Days On Market
• 

  

  /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
• 

  

  /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 $205,003

  Last Listing Agent Dustin Crawford Iowa Home & Land Realty

  315 S 5th Ave, Winterset, IA 50273
• 

  

  /28

  Est $232,849

  Not Listed For Sale

  902 W Court Ave, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,268 Sq Ft
  • Built 1959

  902 W Court Ave, Winterset, IA 50273

  Last Sold Summary

  • 4 Days On Market
• 

  /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
• 

  

  /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
• 

  

  /24

  Est $260,625

  Not Listed For Sale

  906 W Court Ave, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,260 Sq Ft
  • Built 1959

  906 W Court Ave, Winterset, IA 50273

  Last Sold Summary

  • 20 Days On Market
• 

  

  /35

  $365,000

  • 4 Beds
  • 3 Baths
  • 1,524 Sq Ft

  1405 W Court Ave, Winterset, IA 50273

  Step inside and you'll be welcomed by a spacious entry that opens into the vaulted living room, where a cozy fireplace creates the perfect gathering space. This well-maintained ranch offers over 2,500 finished square feet, 4 bedrooms, and 3 bathrooms. The spacious kitchen features maple cabinetry, newer granite countertops, updated appliances, and large windows that showcase views of the

  Lauren Moore Agency Iowa

  1405 W Court Ave, Winterset, IA 50273
• 

  

  /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
• 

  

  /35

  Est $245,954

  Not Listed For Sale

  815 W Court Ave, Winterset, IA 50273

  • 2 Beds
  • 1.5 Baths
  • 1,254 Sq Ft
  • Built 1958

  815 W Court Ave, Winterset, IA 50273

  Last Sold Summary

  • 201 Days On Market
• 

  /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
• 

  

  /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
• 

  

  /26

  Est $276,202

  Not Listed For Sale

  708 N 4th Ave, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,830 Sq Ft
  • Built 1917

  708 N 4th Ave, Winterset, IA 50273

  Last Sold Summary

  • 10 Days On Market
• 

  

  /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
• 

  

  /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

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