Winterset, IA Homes

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  /31

  $254,000

  • 4 Beds
  • 2 Baths
  • 1,104 Sq Ft

  609 E Filmore St, Winterset, IA 50273

  Recently updated ranch style home with 4 bedrooms and 2 baths. Interior includes three BR’s on the main floor, living room, and kitchen just off attached one car garage. One bedroom on the main level would also make a perfect office space and was previously used as a sewing room. All bedrooms have generous sized closets. Updated kitchen with bright over the sink window facing south, included

  

  Toni Tindle

  Covered Bridge Realty

  (515) 373-5687

  609 E Filmore St, Winterset, IA 50273
• Explore Winterset

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  /20

  $995 per month

  Cherry Creek

  3 Beds

  1407 W Mills St, Winterset, IA 50273

  1407 W Mills St, Winterset, IA 50273
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  /28

  $120,000 Sold Feb 27, 2026

  207 E Buchanan St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft
  • Built 1920

  Last Sold Summary

  • 19% Below List Price
  • $96/SF
  • 125 Days On Market

  Current Estimated Value $151,628

  Last Listing Agent Toni Tindle Covered Bridge Realty

  207 E Buchanan St, Winterset, IA 50273
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  /29

  Not Listed For Sale

  808 S 5th Ave, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1890

  808 S 5th Ave, Winterset, IA 50273

  Last Sold Summary

  • 280% Above List Price
  • $69/SF
  • 95 Days On Market

  Last Sold Price $85,000

  Last Listing Agent Roger Queck Pro Team Realty
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  /2

  $285,000 Pending

  • Studio
  • 1,385 Sq Ft

  816 N 3rd Ave, Winterset, IA 50273

  24 HOUR SALE

  

  Toni Tindle

  Covered Bridge Realty

  (515) 762-6726

  816 N 3rd Ave, Winterset, IA 50273
• 

  /2

  $950 per month

  • 1 Bed
  • 600 Sq Ft
  • House for Rent

  59 W Jefferson St, Winterset, IA 50273

  Available immediately is a large sunny apartment located on the square in Winterset, above the US Cellular store. The best part of this quiet unit is the stunning view of the Madison County Courthouse out of the two large front windows. There is an extra-large eat-in kitchen with a pantry, large bathroom and a huge storage closet. The beautiful hardwood floors and the unique antique pocket doors

  Rachel Eller Summerset Realty

  59 W Jefferson St, Winterset, IA 50273
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  /35

  $299,000 Sold Feb 03, 2026

  724 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 1898

  Last Sold Summary

  • 15% Below List Price
  • $123/SF
  • 228 Days On Market

  Current Estimated Value $309,959

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  724 W Jefferson St, Winterset, IA 50273
• 

  

  /35

  Est $330,571 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

  • 5% Above List Price
  • $159/SF
  • 103 Days On Market

  Last Sold Price $315,000

  Last Listing Agent Adam Bugbee Real Broker, LLC
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  /35

  $440,000

  • 3 Beds
  • 3 Baths
  • 2,389 Sq Ft

  1913 N 1st St, Winterset, IA 50273

  Hard to find home on this parcel just N of Winterset 4-way intersection of Hwy 92 & 169. This home has 3BR's & 3 baths sitting proudly on nearly 1 acre. Kitchen has had a complete remodel including adding a convenient island & farm sink. Master/BR on 1st floor has large walk-in closet, & tiled walk-in shower. Main floor laundry off the kitchen. Other features on the 1st level include a formal

  

  Toni Tindle

  Covered Bridge Realty

  (515) 824-5239

  1913 N 1st St, Winterset, IA 50273
• 

  

  /10

  $545 - $790 per month

  Historic Winterset High School Apartments 55+

  Studio - 2 Beds

  110 W Washington St, Winterset, IA 50273

  Call today to learn more about Historic Winterset High School Apartments Senior 55+ , NOW LEASING for June 1, 2024!

  110 W Washington St, Winterset, IA 50273
• 

  /2

  $85,000 Sold Nov 13, 2025

  315 E Green St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1938

  Last Sold Summary

  • 15% Below List Price
  • $118/SF
  • 0 Days On Market

  Current Estimated Value $93,601

  Last Listing Agent Betsy Breeding Realty ONE Group Impact

  315 E Green St, Winterset, IA 50273
• 

  

  /31

  Est $771,843 Not Listed For Sale

  2990 214th Trail, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • Built 2002

  2990 214th Trail, Winterset, IA 50273

  Last Sold Summary

  • 6% Above List Price
  • $425/SF
  • 73 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Julianna Cullen RE/MAX
• 

  

  /26

  $205,000 Pending

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

  827 W Fremont St, Winterset, IA 50273

  Just listed . . . . townhome in the West End Townhomes located off W Fremont Street in Winterset. E-Z access as you enter the quiet cul-de-sac with circle drive designed with room for additional parking. Two-bedroom two bath home with 1,213 square feet of finish on the main level. Large well-lit living room has gas log fireplace as a focal point. An adjacent walk-in coat closet with shelving is

  

  Toni Tindle

  Covered Bridge Realty

  (515) 575-2601

  827 W Fremont St, Winterset, IA 50273
• 

  

  /10

  $1,300 per month

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • House for Rent

  1202 W South St, Winterset, IA 50273

  Property Id: 1608183In this adorable home you will find peace and privacy while still reaping all the benefits of small-town life! Located in a quiet neighborhood, this property's southern border runs along the fence of a neighboring horse pasture; and there is space for a garden in the beautiful back yard. The house has original hard wood floors, and new carpet in the two

  1202 W South St, Winterset, IA 50273
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  /30

  $181,000 Sold May 12, 2025

  712 N 2nd Ave, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,358 Sq Ft
  • Built 1905

  Last Sold Summary

  • 19% Below List Price
  • $133/SF
  • 207 Days On Market

  Current Estimated Value $182,815

  Last Listing Agent Toni Tindle Covered Bridge Realty

  712 N 2nd Ave, Winterset, IA 50273
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  /5

  Not Listed For Sale

  301 Maple Point, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2024

  301 Maple Point, Winterset, IA 50273

  Last Sold Summary

  • $264/SF
  • 99 Days On Market

  Last Sold Price $369,555

  Last Listing Agent Robert D. Weeks Iowa Realty Waukee
• 

  

  /23

  $169,900

  • 3 Beds
  • 1.5 Baths
  • 1,306 Sq Ft

  604 E Jefferson St, Winterset, IA 50273

  Story and 1/2, 3BR 1.5 bath affordable home located in Winterset. Large eat-in kitchen, huge living room with staircase on one end. Staircase leads to 3 bedrooms on the second floor with 1/2 bath. Main floor laundry. Bath on second floor can be entered from the hall or access through SW bedroom. Enclosed rear porch off kitchen attached one car garage with entrance on both ends totals 544 sq feet.

  

  Toni Tindle

  Covered Bridge Realty

  (515) 361-3110

  604 E Jefferson St, Winterset, IA 50273
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  /4

  $1,074 total monthly price

  • 1 - 2 Beds
  • 2 Baths
  • 640 Sq Ft
  • Condo for Rent

  428 W Mills St, Winterset, IA 50273

  Rent is based on income if rental assistance is available. Section 8 accepted.12 Month Lease$400 DepositStove & Fridge provided. Coin operated laundry on site. This institution is an equal opportunity provider.* Prices and availability subject to change without notice.* Square footage definitions vary. Displayed square footage is

  428 W Mills St, Winterset, IA 50273
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  /32

  $265,000 Sold Nov 19, 2025

  620 W Filmore St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,741 Sq Ft
  • Built 1947

  Last Sold Summary

  • 11% Below List Price
  • $152/SF
  • 164 Days On Market

  Current Estimated Value $262,859

  Last Listing Agent Alyssa Tadlock Madison County Realty

  620 W Filmore St, Winterset, IA 50273
• 

  

  /28

  Est $402,942 Not Listed For Sale

  1912 Dogwood Ln, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,712 Sq Ft
  • Built 2024

  1912 Dogwood Ln, Winterset, IA 50273

  Last Sold Summary

  • 12% Above List Price
  • $209/SF
  • 635 Days On Market

  Last Sold Price $358,409

  Last Listing Agent Robert D. Weeks Iowa Realty Waukee
• 

  

  /27

  $245,000

  • 3 Beds
  • 1 Bath
  • 962 Sq Ft

  710 N 3rd Ave, Winterset, IA 50273

  Corner lot three-bedroom, one bath ranch with attached garage on Winterset West side. Home has fenced yard, great fire pit area for outdoor entertaining, contained decorative garden/flower beds and a row of new trees. Other new yard features include landscaping rock and creative oval garden landscaping mound. Updates include fully encapsulated deep crawl space with warranty and new sump pump.

  

  Toni Tindle

  Covered Bridge Realty

  (515) 949-4406

  710 N 3rd Ave, Winterset, IA 50273
• 

  

  /4

  $1,074 total monthly price

  • 1 - 2 Beds
  • 2 Baths
  • 640 Sq Ft
  • Condo for Rent

  428 W Mills St, Winterset, IA 50273

  Rent is based on income if rental assistance is available. Section 8 accepted.12 Month Lease$400 DepositStove & Fridge provided. Coin operated laundry on site. This institution is an equal opportunity provider.* Prices and availability subject to change without notice.* Square footage definitions vary. Displayed square footage is

  428 W Mills St, Winterset, IA 50273
• 

  

  /7

  $119,000 Sold Nov 14, 2025

  Lot 36 Limestone Ct, Winterset, IA 50273

  • Land
  • 2.95 Acres
  • $40,339 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 341 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 36 Limestone Ct, Winterset, IA 50273
• 

  

  /25

  Est $176,024 Not Listed For Sale

  509 W Summit St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1885

  509 W Summit St, Winterset, IA 50273

  Last Sold Summary

  • 7% Above List Price
  • $190/SF
  • 128 Days On Market

  Last Sold Price $164,000

  Last Listing Agent Austin Postier RE/MAX Results
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  /16

  $165,000

  • 3 Beds
  • 1 Bath
  • 1,523 Sq Ft

  118 N 5th St, Winterset, IA 50273

  Charm with economy! That's what this 5BR, 1 bath, 1.5 story home offers! Great natural light from the large east-facing picture window in the living room. There are 3 bedrooms on the main level, along with the full bath. The open carpeted stairway will lead you to the 2 non-conforming bedrooms (no closets) on the 2nd level. Easy-to-clean laminate flooring throughout main level. The main floor

  

  Toni Tindle

  Covered Bridge Realty

  (515) 882-4007

  118 N 5th St, Winterset, IA 50273
• 

  

  /31

  $395,000 Sold Jun 16, 2025

  2923 N John Wayne Dr, Winterset, IA 50273

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

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Rachel Eller Summerset Realty

  2923 N John Wayne Dr, Winterset, IA 50273
• 

  

  /15

  Est $339,682 Not Listed For Sale

  815 N 11th Avenue Cir, Winterset, IA 50273

  • 3 Beds
  • 3 Baths
  • 1,356 Sq Ft
  • Built 2021

  815 N 11th Avenue Cir, Winterset, IA 50273

  Last Sold Summary

  • 9% Above List Price
  • $231/SF
  • 61 Days On Market

  Last Sold Price $313,000

  Last Listing Agent Brent Kelso Silverado Realty
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  /35

  $1,250,000

  • Land
  • 57.36 Acres
  • $21,792 per Acre

  1826 Green Ln, Winterset, IA 50273

  57.36 Acres with Log Home, Livestock Facilities & Equipment – Earlham School District Located just 3 miles north of Highway 92 and approximately 2 miles east of Earlham Road, this 57.36 gross acre property offers a great combination of rural living, pasture ground, and functional farm improvements. The property features a 2-story log cabin style home built in 1996 offering approximately 2,282

  Shane Spyksma Kiloterra

  1826 Green Ln, Winterset, IA 50273
• 

  /2

  $339,000 Sold Oct 24, 2025

  708 W Fremont St, Winterset, IA 50273

  • 4 Beds
  • 2.5 Baths
  • 2,026 Sq Ft
  • Built 1895

  Last Sold Summary

  • $167/SF
  • 1 Day On Market

  Current Estimated Value $330,484

  Last Listing Agent Rachel Eller Summerset Realty

  708 W Fremont St, Winterset, IA 50273
• 

  

  /23

  Est $222,186 Not Listed For Sale

  714 W Mills St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 982 Sq Ft
  • Built 1993

  714 W Mills St, Winterset, IA 50273

  Last Sold Summary

  • 8% Above List Price
  • $209/SF
  • 26 Days On Market

  Last Sold Price $205,000

  Last Listing Agent Timothy Lucken Real Broker, LLC
• 

  

  /33

  $478,750

  • Land
  • 5 Acres
  • $95,750 per Acre

  2980 Clark Tower Rd, Winterset, IA 50273

  Located in scenic Madison County this newly built home and buildings offers peace and quiet with close commute to Winterset and West Des Moines. Located on hard surface road 8.5 miles south of Winterset. The home offers 2 bedrooms and 2 baths. The main floor offers an open concept with a nice main living and dining area. The upstairs offers the opportunity to expand to increase finished square

  Luke Skinner Iowa Land Company

  2980 Clark Tower Rd, Winterset, IA 50273
• 

  

  /35

  $1,235,000 Sold Mar 20, 2026

  1890 Hogback Bridge Rd, Winterset, IA 50273

  • Land
  • 29.7 Acres
  • $41,582 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 109 Days On Market

  Current Estimated Value $1,358,034

  Last Listing Agent Lenchen Raeside RE/MAX Concepts

  1890 Hogback Bridge Rd, Winterset, IA 50273
• 

  

  /25

  Est $317,555 Not Listed For Sale

  703 W Court Ave, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 2,698 Sq Ft
  • Built 1875

  703 W Court Ave, Winterset, IA 50273

  Last Sold Summary

  • 10% Above List Price
  • $107/SF
  • 2 Days On Market

  Last Sold Price $288,000

  Last Listing Agent Catie Croat RE/MAX
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  /34

  $750,000

  • Land
  • 4.56 Acres
  • $164,474 per Acre

  1685 McBride Ridge Ct, Winterset, IA 50273

  The perfect balance of executive luxury and rural serenity in this stunning 4-bedroom, 3.5-bathroom partial brick walkout ranch, situated on 4.56 scenic acres in Madison Co. Located on a private drive just off Cumming Highway, this property offers a peaceful country lifestyle on hard surface for an easy commute to DSM or Winterset. The home features 2x6 construction, rich woodwork, granite

  Sean Asada Iowa Land Man (Remax Real Estate Center)

  1685 McBride Ridge Ct, Winterset, IA 50273
• 

  

  /34

  $575,000 Sold Sep 12, 2025

  711 E Madison St, Winterset, IA 50273

  • 5 Beds
  • 3 Baths
  • 1,739 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $331/SF
  • 92 Days On Market

  Current Estimated Value $529,201

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  711 E Madison St, Winterset, IA 50273
• 

  

  /24

  Est $201,429 Not Listed For Sale

  621 E Court Ave, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,842 Sq Ft
  • Built 1860

  621 E Court Ave, Winterset, IA 50273

  Last Sold Summary

  • 7% Above List Price
  • $102/SF
  • 105 Days On Market

  Last Sold Price $187,500

  Last Listing Agent Tamra Yeager Pro Team Realty
• 

  

  /11

  $372,750

  • Land
  • 18.64 Acres
  • $19,997 per Acre

  0 Clark Tower Rd, Winterset, IA 50273

  Premium Executive Building Lot on Pavement | Just South of Winterset, Iowa Peoples Company is proud to represent the Utsler Family Trust in the sale of an exceptional 18.64-acre executive building lot located just 3 miles south of Winterset, Iowa, with direct access off paved Clark Tower Road. This recently surveyed property offers the rare combination of privacy, premium views, utilities at

  Andrew Zellmer Peoples Company

  0 Clark Tower Rd, Winterset, IA 50273
• 

  

  /22

  $318,000 Sold Jan 02, 2026

  2378 Francesca Ave, Winterset, IA 50273

  • Land
  • 26.47 Acres
  • $12,014 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 8 Days On Market

  Last Listing Agent Matt Skinner Iowa Land Company

  2378 Francesca Ave, Winterset, IA 50273
• 

  

  /28

  $354,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,333 Sq Ft

  215 W Buchanan St, Winterset, IA 50273

  Better than new, this fully renovated home offers 1,700+ total finished square feet and is truly move-in ready. This 4-bedroom, 3-bath property blends modern style with small-town charm in a mature, established neighborhood. Everything is brand new — electrical, plumbing, HVAC, drywall, trim, doors, windows, paint, flooring, kitchen, bathrooms, and more — but with the character and location you

  Elizabeth Gordon Realty ONE Group Impact

  215 W Buchanan St, Winterset, IA 50273

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