Winterset, IA Homes

• 

  

  

  /29

  Est $285,969

  Not Listed For Sale

  602 N 1st Ave, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 2,146 Sq Ft
  • Built 1894

  602 N 1st Ave, Winterset, IA 50273

  Last Sold Summary

  • 58 Days On Market
• 

  

  

  /26

  $259,000

  $11K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,859 Sq Ft

  319 S 7th Ave, Winterset, IA 50273

  WELCOME HOME to this beautiful 3 bed/1 bath home on .32 ac lot. You will LOVE walking into the large living room, with plenty of NATURAL LIGHT and nice sized dining area. The kitchen has plenty of COUNTER SPACE and also a nice sized ISLAND. Off of the kitchen is the large 4 SEASON PORCH/family room (12'x33') with plenty of windows and natural light. The perfect area for ENTERTAINING! Two bedrooms

  Betsy Breeding Realty ONE Group Impact

  319 S 7th Ave, Winterset, IA 50273
• 

  

  

  /7

  $120,000

  Sold Mar 06, 2026

  Lot 38 Limestone Ct, Winterset, IA 50273

  • Land
  • 3.57 Acres
  • $33,613 per Acre

  Last Sold Summary

  • 19% Below List Price
  • 459 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 38 Limestone Ct, Winterset, IA 50273
• 

  

  

  /35

  Est $328,460

  Not Listed For Sale

  119 E Buchanan St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,984 Sq Ft
  • Built 1925

  119 E Buchanan St, Winterset, IA 50273

  Last Sold Summary

  • 103 Days On Market
• 

  

  

  /31

  $274,900

  $40K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,880 Sq Ft

  804 N 4th Ave, Winterset, IA 50273

  Welcome to a truly extraordinary home where timeless craftsmanship, modern luxury, and stunningnatural beauty come together in perfect harmony. Rarely does a property offer such a unique blend of old-world artisan detail and contemporary design, all set against the backdrop of gardens so exquisite! From the moment you arrive, the lush landscaping captures your attention, showcasing a level of

  Sarah Cowman Homefront Real Estate, LLC

  804 N 4th Ave, Winterset, IA 50273
• 

  

  /28

  $260,000

  Sold Jun 10, 2026

  1509 W South St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 864 Sq Ft
  • Built 1982

  Last Sold Summary

  • 5% Below List Price
  • $301/SF
  • 56 Days On Market

  Current Estimated Value $268,649

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  1509 W South St, Winterset, IA 50273
• 

  

  /16

  Est $160,192

  Not Listed For Sale

  215 E Buchanan St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • Built 1941

  215 E Buchanan St, Winterset, IA 50273

  Last Sold Summary

  • 20 Days On Market
• 

  /2

  $395,000

  • Land
  • 3 Acres
  • $131,667 per Acre

  Lot 5 N 4th Ave, Winterset, IA 50273

  New Light Commercial Development. Lots will be ready to be built upon in Spring 2025, road pave in Fall 2024. 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 5 N 4th Ave, Winterset, IA 50273
• 

  

  /35

  $775,000

  Sold May 21, 2026

  112 S 16th Ave, Winterset, IA 50273

  • 4 Beds
  • 4 Baths
  • 2,826 Sq Ft
  • Built 1964

  Last Sold Summary

  • 6% Below List Price
  • $274/SF
  • 23 Days On Market

  Current Estimated Value $801,852

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  112 S 16th Ave, Winterset, IA 50273
• 

  

  /19

  Est $184,684

  Not Listed For Sale

  65 E North St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft
  • Built 1870

  65 E North St, Winterset, IA 50273

  Last Sold Summary

  • 182 Days On Market
• 

  

  /34

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,396 Sq Ft

  302 W Court Ave, Winterset, IA 50273

  Timeless charm meets thoughtful updates in this classic 2-story home built in 1890, ideally located on historic Court Ave just one block from the town square. Offering 2,396 square feet, 3 bedrooms, and 2.5 baths, this beautifully maintained home blends original character with modern functionality in all the right ways. The showstopping custom-designed kitchen is truly the heart of the home,

  Jennifer Stover Madison County Realty

  302 W Court Ave, Winterset, IA 50273
• 

  

  /29

  $285,000

  Sold Jul 16, 2025

  311 W North St, Winterset, IA 50273

  • 3 Beds
  • 3 Baths
  • 1,388 Sq Ft
  • Built 2004

  Last Sold Summary

  • $205/SF
  • 47 Days On Market

  Current Estimated Value $296,762

  Last Listing Agent Abbey Robertson Century 21 Signature

  311 W North St, Winterset, IA 50273
• 

  

  /24

  Est $135,680

  Not Listed For Sale

  510 N 1st Ave, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 624 Sq Ft
  • Built 1950

  510 N 1st Ave, Winterset, IA 50273

  Last Sold Summary

  • 29 Days On Market
• 

  

  /17

  $229,900

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,270 Sq Ft

  1413 W Washington St, Winterset, IA 50273

  Beautifully maintained, this 4-bedroom ranch offers easy single-level living with an inviting open floor plan. A rare oversized 3-car garage with additional storage is a dream for car enthusiasts or hobbyists, and the deck off the kitchen provides the perfect backdrop for outdoor dining and entertaining!

  Sarah Cowman Homefront Real Estate, LLC

  1413 W Washington St, Winterset, IA 50273
• 

  

  /31

  $107,500

  Sold Nov 20, 2025

  59 E Washington St, Winterset, IA 50273

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

  Last Sold Summary

  • 19% Below List Price
  • $114/SF
  • 113 Days On Market

  Current Estimated Value $117,936

  Last Listing Agent John Brummett RE/MAX Precision

  59 E Washington St, Winterset, IA 50273
• 

  

  /24

  Est $278,786

  Not Listed For Sale

  719 W Washington St, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 1,456 Sq Ft
  • Built 1903

  719 W Washington St, Winterset, IA 50273

  Last Sold Summary

  • 109 Days On Market
• 

  

  /26

  $330,000

  • 4 Beds
  • 3 Baths
  • 1,990 Sq Ft

  1706 W Summit St, Winterset, IA 50273

  This two-story brick home, built in 1923, has all of the character and charm that goes with a 1920s house. Original built-ins, woodwork, hardwood floors and glass doorknobs still remain in the house. With 1990 sf, 4 bedroom and 3 baths, there is plenty of room for everyone. The first floor features a large family room with beautiful built-ins surrounding the fireplace. French doors from the

  Larry Corkrean Madison County Realty

  1706 W Summit St, Winterset, IA 50273
• 

  

  /29

  $325,000

  Sold Nov 19, 2025

  916 W Filmore St, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2014

  Last Sold Summary

  • $242/SF
  • 4 Days On Market

  Current Estimated Value $276,365

  Last Listing Agent Jennifer Stover Madison County Realty

  916 W Filmore St, Winterset, IA 50273
• 

  

  /20

  Est $306,711

  Not Listed For Sale

  316 S 7th Ave, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft
  • Built 2021

  316 S 7th Ave, Winterset, IA 50273

  Last Sold Summary

  • 24 Days On Market
• 

  

  /14

  $285,000

  $32K PRICE DROP Pending

  • Land
  • 13.5 Acres
  • $21,111 per Acre

  2571 250th Ln, Winterset, IA 50273

  A stunning piece of ground at the end of a dead end road! Aproximately 13.5 acres to be surveyed off. This would make a beautiful executive building lot, or a fun place to go camp on the weekends! The pond is stocked for all of you who like to fish. There will be some restrctive covenants but horses and some farm animals will be allowed. Final price will be per acre based on the survey. Come

  Sarah Cowman Homefront Real Estate, LLC

  2571 250th Ln, Winterset, IA 50273
• 

  

  /25

  $180,000

  Sold Apr 08, 2026

  4922 Cedar Ln, Winterset, IA 50273

  • Land
  • 4.88 Acres
  • $36,885 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 7 Days On Market

  Current Estimated Value $178,567

  Last Listing Agent Will Cooper Midwest Land Group LLC

  4922 Cedar Ln, Winterset, IA 50273
• 

  

  /21

  Est $186,284

  Not Listed For Sale

  608 W South St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,072 Sq Ft
  • Built 1926

  608 W South St, Winterset, IA 50273

  Last Sold Summary

  • 164 Days On Market
• 

  

  /29

  $242,000

  Sold Dec 12, 2025

  120 S 8th Ave, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft
  • Built 1967

  Last Sold Summary

  • 7% Below List Price
  • $155/SF
  • 52 Days On Market

  Current Estimated Value $264,512

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  120 S 8th Ave, Winterset, IA 50273
• 

  

  /32

  Est $319,558

  Not Listed For Sale

  612 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 1,976 Sq Ft
  • Built 1905

  612 W Jefferson St, Winterset, IA 50273

  Last Sold Summary

  • 77 Days On Market
• 

  

  /34

  $655,000

  Sold Mar 23, 2026

  1821 Millstream Ct, Winterset, IA 50273

  • 4 Beds
  • 3.5 Baths
  • 2,200 Sq Ft
  • Built 2005

  Last Sold Summary

  • 6% Below List Price
  • $298/SF
  • 219 Days On Market

  Current Estimated Value $642,347

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  1821 Millstream Ct, Winterset, IA 50273
• 

  

  /18

  Est $203,795

  Not Listed For Sale

  212 N 4th Ave, Winterset, IA 50273

  • 2 Beds
  • 1.5 Baths
  • 884 Sq Ft
  • Built 1959

  212 N 4th Ave, Winterset, IA 50273

  Last Sold Summary

  • 11 Days On Market
• 

  /2

  $155,000

  Sold Jan 15, 2026

  00 Roseman Bridge Rd, Winterset, IA 50273

  • Land
  • 10 Acres
  • $15,500 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Lauren Moore Agency Iowa

  00 Roseman Bridge Rd, Winterset, IA 50273
• 

  

  /35

  Est $449,371

  Not Listed For Sale

  218 S 2nd Ave, Winterset, IA 50273

  • 4 Beds
  • 6 Baths
  • 3,325 Sq Ft
  • Built 1949

  218 S 2nd Ave, Winterset, IA 50273

  Last Sold Summary

  • 395 Days On Market
• 

  

  /27

  $203,750

  Sold Mar 06, 2026

  821 W Fremont St, Winterset, IA 50273

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

  Last Sold Summary

  • 5% Below List Price
  • $168/SF
  • 16 Days On Market

  Current Estimated Value $208,138

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  821 W Fremont St, Winterset, IA 50273
• 

  

  /34

  Est $316,187

  Not Listed For Sale

  211 W South St, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft
  • Built 1880

  211 W South St, Winterset, IA 50273

  Last Sold Summary

  • 13 Days On Market
• 

  

  /17

  $170,000

  Sold Feb 02, 2026

  1022 W Washington St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $182/SF
  • 4 Days On Market

  Current Estimated Value $180,080

  Last Listing Agent Matt Cole RE/MAX Concepts

  1022 W Washington St, Winterset, IA 50273
• 

  

  /35

  Est $425,068

  Not Listed For Sale

  220 W Washington St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 4,315 Sq Ft
  • Built 1910

  220 W Washington St, Winterset, IA 50273

  Last Sold Summary

  • 616 Days On Market
• 

  

  /25

  $157,800

  Sold Aug 20, 2025

  702 N 2nd Ave, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 1,336 Sq Ft
  • Built 1870

  Last Sold Summary

  • 12% Below List Price
  • $118/SF
  • 59 Days On Market

  Current Estimated Value $171,115

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  702 N 2nd Ave, Winterset, IA 50273
• 

  

  /35

  Est $269,693

  Not Listed For Sale

  223 S 1st Ave, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 1,058 Sq Ft
  • Built 1948

  223 S 1st Ave, Winterset, IA 50273

  Last Sold Summary

  • 10 Days On Market
• 

  

  /35

  $570,000

  Sold Mar 03, 2026

  1694 McBride Ridge Ct, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,878 Sq Ft
  • Built 2003

  Last Sold Summary

  • 12% Below List Price
  • $304/SF
  • 202 Days On Market

  Current Estimated Value $588,027

  Last Listing Agent Michelle Price Realty ONE Group Impact

  1694 McBride Ridge Ct, Winterset, IA 50273
• 

  

  /21

  Est $145,137

  Not Listed For Sale

  215 S 2nd St, Winterset, IA 50273

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

  215 S 2nd St, Winterset, IA 50273

  Last Sold Summary

  • 5 Days On Market
• 

  

  /22

  $212,000

  Sold Sep 29, 2025

  1424 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,088 Sq Ft
  • Built 1993

  Last Sold Summary

  • $195/SF
  • 3 Days On Market

  Current Estimated Value $207,557

  Last Listing Agent Rachel Eller Summerset Realty

  1424 W Jefferson St, Winterset, IA 50273
• 

  

  /23

  Est $199,774

  Not Listed For Sale

  323 E Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 992 Sq Ft
  • Built 1947

  323 E Jefferson St, Winterset, IA 50273

  Last Sold Summary

  • 6 Days On Market
• 

  

  /35

  $620,000

  Sold Jun 18, 2026

  2378 Cumming Rd, Winterset, IA 50273

  • 4 Beds
  • 3.5 Baths
  • 1,912 Sq Ft
  • Built 2017

  Last Sold Summary

  • 1% Below List Price
  • $324/SF
  • 10 Days On Market

  Current Estimated Value $618,094

  Last Listing Agent Abbey Robertson Century 21 Signature

  2378 Cumming Rd, Winterset, IA 50273
• 

  

  /20

  Est $310,488

  Not Listed For Sale

  2626 Fieldstone Ave, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft
  • Built 2006

  2626 Fieldstone Ave, Winterset, IA 50273

  Last Sold Summary

  • 13 Days On Market

Showing Results 281 - 320, Page 8 of 18