Winterset, IA Homes

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  /28

  $169,000 Sold Oct 21, 2025

  415 W Summit St, Winterset, IA 50273

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

  Last Sold Summary

  • $209/SF
  • 4 Days On Market

  Current Estimated Value $165,365

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  415 W Summit St, Winterset, IA 50273
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  /34

  Est $239,834 Not Listed For Sale

  203 W North St, Winterset, IA 50273

  • 4 Beds
  • 1.5 Baths
  • 2,050 Sq Ft
  • Built 1895

  203 W North St, Winterset, IA 50273

  Last Sold Summary

  • 18% Above List Price
  • $100/SF
  • 22 Days On Market

  Last Sold Price $204,000

  Last Listing Agent Rachel Eller Summerset Realty
• 

  

  

  /35

  $349,900

  • 6 Beds
  • 3 Baths
  • 1,800 Sq Ft

  117 E North St, Winterset, IA 50273

  Welcome to timeless Americana charm in the heart of beautiful Winterset. Nestled on a quiet, tree lined street just moments from the beloved historic square, this spacious 2 sty offers warmth, character and a sense of community that make Winterset such a special place to call home. With 6 bedrooms and 3 baths, this home offers remarkable flexibility and room to grow. 4 bedrooms are on 2nd level

  Lisa Davis RE/MAX Precision

  117 E North St, Winterset, IA 50273
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  /25

  $575,000 Sold Nov 20, 2025

  2283 Pioneer Ave, Winterset, IA 50273

  • Land
  • 20 Acres
  • $28,750 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 40 Days On Market

  Current Estimated Value $552,926

  Last Listing Agent Bryan Curtis Attain RE

  2283 Pioneer Ave, Winterset, IA 50273
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  /35

  Est $620,336 Not Listed For Sale

  2064 226th Ct, Winterset, IA 50273

  • 4 Beds
  • 3.5 Baths
  • Built 2006

  2064 226th Ct, Winterset, IA 50273

  Last Sold Summary

  • 7% Above List Price
  • $228/SF
  • 136 Days On Market

  Last Sold Price $580,000

  Last Listing Agent Jennifer Stover Madison County Realty
• 

  

  /23

  $299,900

  • 3 Beds
  • 2 Baths
  • 838 Sq Ft

  521 W Hutchings St, Winterset, IA 50273

  Walk out ranch home with huge yard! This is a must see property! You will appreciate the updated inside featuring a bright eat in kitchen (the kitchen appliances are all included!). The living room has a cozy electric fireplace and nice big windows overlooking the huge back yard. There are 2 bedrooms and a full bath upstairs. The basement is a bright sunny walk out with a large family room,

  Sarah Cowman Homefront Real Estate, LLC

  521 W Hutchings St, Winterset, IA 50273
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  /6

  $100,000 Sold Aug 01, 2025

  Lot 1 114th Ct, Winterset, IA 50273

  • Land
  • 5.32 Acres
  • $18,797 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 269 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 1 114th Ct, Winterset, IA 50273
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  /35

  Est $565,248 Not Listed For Sale

  2395 148th St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • Built 1998

  2395 148th St, Winterset, IA 50273

  Last Sold Summary

  • 10% Above List Price
  • $312/SF
  • 6 Days On Market

  Last Sold Price $515,000

  Last Listing Agent James Von Gillern RE/MAX
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  /35

  $449,900 Pending

  • 5 Beds
  • 3 Baths
  • 2,137 Sq Ft

  812 N 8th Ave, Winterset, IA 50273

  Spacious and inviting, this large ranch in Winterset offers the perfect blend of comfort and style. You will love the stunning stone fireplace as the focal point in the living room with vaulted-ceilings, creating a warm and welcoming atmosphere. The kitchen is nice with granite countertops and plenty of cabinets. The primary bedroom is complete with an ensuite featuring a tile shower with dual

  Matt Cole RE/MAX Concepts

  812 N 8th Ave, Winterset, IA 50273
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  /27

  $269,000 Sold Oct 16, 2025

  822 N 3rd Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft
  • Built 2005

  Last Sold Summary

  • $191/SF
  • 4 Days On Market

  Current Estimated Value $263,245

  Last Listing Agent Bruce Seymour RE/MAX Precision

  822 N 3rd Ave, Winterset, IA 50273
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  /33

  Est $414,321 Not Listed For Sale

  906 N 14th Ave, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft
  • Built 2005

  906 N 14th Ave, Winterset, IA 50273

  Last Sold Summary

  • 9% Above List Price
  • $226/SF
  • 3 Days On Market

  Last Sold Price $380,000

  Last Listing Agent Betsy Breeding Realty ONE Group Impact
• 

  

  /23

  $309,900

  • 3 Beds
  • 1.5 Baths
  • 2,130 Sq Ft

  721 W Court Ave, Winterset, IA 50273

  Don't miss the opportunity to own this home on historical Court Avenue! You will love sitting on the wraparound porch for your morning coffee or just some time to relax. Upon entering the home, you will be impressed with the beautiful details of the open staircase. The first floor has a large living, family and dining rooms, 1/2 bath and kitchen. The hardwood floors and the woodwork are original

  Larry Corkrean Madison County Realty

  721 W Court Ave, Winterset, IA 50273
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  /23

  $270,000 Sold Sep 18, 2025

  0000 Hogback Bridge Rd, Winterset, IA 50273

  • Land
  • 22.01 Acres
  • $12,267 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 4 Days On Market

  Last Listing Agent Dennis Williams Midwest Land Group LLC

  0000 Hogback Bridge Rd, Winterset, IA 50273
• 

  

  /23

  Est $356,030 Not Listed For Sale

  807 N 15th Ave, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,273 Sq Ft
  • Built 2007

  807 N 15th Ave, Winterset, IA 50273

  Last Sold Summary

  • 10% Above List Price
  • $255/SF
  • 2 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
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  /13

  $309,990

  • 4 Beds
  • 3 Baths
  • 1,464 Sq Ft

  623 W Green St, Winterset, IA 50273

  Charming, solid, and beautifully cared for -this all-brick ranch in historic Madison County is the one you've been waiting for. With standout curb appeal and numerous updates throughout, this home blends classic construction with modern comfort. The main level offers three comfortable bedrooms, while the partially finished lower level provides a full additional bedroom plus a fifth non-conforming

  Markjon Trierweiler RE/MAX Precision

  623 W Green St, Winterset, IA 50273
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  /31

  $310,000 Sold Jun 30, 2025

  221 N 15th Ave, Winterset, IA 50273

  • 5 Beds
  • 2.5 Baths
  • 1,415 Sq Ft
  • Built 2002

  Last Sold Summary

  • 7% Below List Price
  • $219/SF
  • 54 Days On Market

  Current Estimated Value $324,059

  Last Listing Agent Danielle Burnight RE/MAX Concepts

  221 N 15th Ave, Winterset, IA 50273
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  /35

  Est $398,038 Not Listed For Sale

  905 N 15th Ave, Winterset, IA 50273

  • 5 Beds
  • 2.5 Baths
  • 1,504 Sq Ft
  • Built 2005

  905 N 15th Ave, Winterset, IA 50273

  Last Sold Summary

  • 12% Above List Price
  • $236/SF
  • 16 Days On Market

  Last Sold Price $355,000

  Last Listing Agent Ian Sparks Homefront Real Estate, LLC
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  /35

  $365,000

  • 4 Beds
  • 2 Baths
  • 2,724 Sq Ft

  615 N 1st Ave, Winterset, IA 50273

  This beautifully remodeled residence combines timeless charm with modern comfort. Step inside to discover hardwood floors and a striking, gracefully designed staircase that sets the tone for the entire home. The inviting front porch offers the perfect spot to welcome guests or enjoy peaceful evenings outdoors. Featuring four generously sized bedrooms plus a bonus room, and a full bath on each

  Sarah Cowman Homefront Real Estate, LLC

  615 N 1st Ave, Winterset, IA 50273
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  /22

  $125,000 Sold Oct 07, 2025

  103 S 3rd St, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,093 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Below List Price
  • $114/SF
  • 82 Days On Market

  Current Estimated Value $128,563

  Last Listing Agent Zineta Imamovic Realty ONE Group Impact

  103 S 3rd St, Winterset, IA 50273
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  /35

  Est $547,780 Not Listed For Sale

  909 N 9th Ave, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 2,692 Sq Ft
  • Built 2006

  909 N 9th Ave, Winterset, IA 50273

  Last Sold Summary

  • 16% Above List Price
  • $175/SF
  • 244 Days On Market

  Last Sold Price $472,000

  Last Listing Agent Jennifer Stover Madison County Realty
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  /24

  $309,000

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft

  212 N 14th Ave, Winterset, IA 50273

  Sweet ranch home located on a quiet street. The open concept floor plan makes this house feel bigger than it is. The 1st floor offers 2 large bedrooms, 1 full bath, kitchen with a breakfast bar and a private home office space. The lower level features a huge family room, large bedroom and full bath - and still plenty of storage space. Sliding door off the dining area leads to the private

  Jennifer Stover Madison County Realty

  212 N 14th Ave, Winterset, IA 50273
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  /35

  $217,000 Sold Jan 15, 2026

  324 S 10th Ave, Winterset, IA 50273

  • 1 Bed
  • 2.5 Baths
  • 1,213 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Below List Price
  • $179/SF
  • 27 Days On Market

  Current Estimated Value $216,511

  Last Listing Agent Toni Tindle Covered Bridge Realty

  324 S 10th Ave, Winterset, IA 50273
• 

  

  /17

  Est $287,844 Not Listed For Sale

  809 W Mills St, Winterset, IA 50273

  • 3 Beds
  • 3 Baths
  • 1,344 Sq Ft
  • Built 2004

  809 W Mills St, Winterset, IA 50273

  Last Sold Summary

  • 11% Above List Price
  • $193/SF
  • 1 Day On Market

  Last Sold Price $260,000

  Last Listing Agent Alyssa Tadlock Madison County Realty
• 

  /2

  $382,500

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

  309 Maple Pointe, Winterset, IA 50273

  Stryker Ranch New Construction with oversized 3 car garage. Front porch with 2 stone base posts. 9' ceilings throughout main floor. Open stairs to basement. Granite or quartz countertops in baths and kitchen. Kitchen boasts of a large walk-in pantry and stainless-steel appliances. White cabinets throughout. Luxury vinyl flooring. Gas fireplace. Master bath with raised vanity and elongated stool.

  Robert D. Weeks Iowa Realty Waukee

  309 Maple Pointe, Winterset, IA 50273
• 

  

  /25

  $213,865 Sold Jun 13, 2025

  707 E Buchanan St, Winterset, IA 50273

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

  Last Sold Summary

  • 2% Above List Price
  • $202/SF
  • 13 Days On Market

  Current Estimated Value $178,657

  Last Listing Agent Jenn Ho Goh GoSynergy Realty

  707 E Buchanan St, Winterset, IA 50273
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  /28

  Est $220,431 Not Listed For Sale

  829 W Fremont St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,213 Sq Ft
  • Built 2001

  829 W Fremont St, Winterset, IA 50273

  Last Sold Summary

  • 1% Above List Price
  • $180/SF
  • 30 Days On Market

  Last Sold Price $218,000

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /29

  $299,000

  • 4 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  203 W Green St, Winterset, IA 50273

  You will love all the space in this UNIQUE 2000+ sq ft home on a large corner lot! Main level includes a massive family room, large kitchen with dinning area and a separate room that could be a formal dining room or office and a half bath. Upstairs there are 3 large bedrooms (one with en suite and walk in closet) plus another smaller room that could also be a bedroom, game room, office or craft

  Alyssa Tadlock Madison County Realty

  203 W Green St, Winterset, IA 50273
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  /34

  $250,000 Sold Sep 22, 2025

  520 W Benton St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,451 Sq Ft
  • Built 1966

  Last Sold Summary

  • $172/SF
  • 19 Days On Market

  Current Estimated Value $246,382

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  520 W Benton St, Winterset, IA 50273
• 

  

  /23

  Est $214,307 Not Listed For Sale

  911 N 6th Avenue Cir, Winterset, IA 50273

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

  911 N 6th Avenue Cir, Winterset, IA 50273

  Last Sold Summary

  • 11% Above List Price
  • $159/SF
  • 20 Days On Market

  Last Sold Price $192,500

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /19

  $300,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,087 Sq Ft

  301 N 15th Ave, Winterset, IA 50273

  Welcome to 301 N 15th Avenue, a well-maintained home ideally located in a quiet, established neighborhood on the north side of Winterset. This inviting property offers a functional layout with comfortable living spaces, making it a great fit for a variety of lifestyles. The home features a bright and welcoming interior with ample natural light throughout. The spacious kitchen provides convenient

  Kate Anderson RE/MAX Concepts

  301 N 15th Ave, Winterset, IA 50273
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  /30

  $285,000 Sold Oct 31, 2025

  701 W Buchanan St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft
  • Built 1950

  Last Sold Summary

  • 1% Below List Price
  • $156/SF
  • 58 Days On Market

  Current Estimated Value $271,503

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  701 W Buchanan St, Winterset, IA 50273
• 

  

  /33

  Est $337,866 Not Listed For Sale

  215 N 15th Ave, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 2,060 Sq Ft
  • Built 2001

  215 N 15th Ave, Winterset, IA 50273

  Last Sold Summary

  • 31% Above List Price
  • $125/SF
  • 26 Days On Market

  Last Sold Price $257,400

  Last Listing Agent Tobi Greene RE/MAX
• 

  

  /31

  $299,000

  • 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
• 

  

  /25

  $185,000 Sold Aug 25, 2025

  507 W Madison St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,030 Sq Ft
  • Built 2021

  Last Sold Summary

  • 12% Below List Price
  • $180/SF
  • 83 Days On Market

  Current Estimated Value $198,373

  Last Listing Agent Toni Tindle Covered Bridge Realty

  507 W Madison St, Winterset, IA 50273
• 

  

  /25

  Est $343,054 Not Listed For Sale

  307 N 14th Ave, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,172 Sq Ft
  • Built 2008

  307 N 14th Ave, Winterset, IA 50273

  Last Sold Summary

  • 11% Above List Price
  • $264/SF
  • 49 Days On Market

  Last Sold Price $309,000

  Last Listing Agent Cy Phillips Space Simply
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  /27

  $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
• 

  

  /25

  $288,000 Sold Nov 14, 2025

  722 W Mills St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 1993

  Last Sold Summary

  • 4% Below List Price
  • $230/SF
  • 24 Days On Market

  Current Estimated Value $281,644

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  722 W Mills St, Winterset, IA 50273
• 

  

  /24

  Est $332,798 Not Listed For Sale

  225 N 14th Ave, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,415 Sq Ft
  • Built 2000

  225 N 14th Ave, Winterset, IA 50273

  Last Sold Summary

  • 21% Above List Price
  • $194/SF
  • 42 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /31

  $264,990 Pending

  • 4 Beds
  • 2 Baths
  • 1,323 Sq Ft

  901 E Buchanan St, Winterset, IA 50273

  Completely remodeled from top to bottom, this move-in ready home blends modern finishes with functional design. The bright, updated kitchen features sleek white cabinetry, solid surface countertops, and stainless appliances, complemented by a spacious walk-in pantry with abundant prep and storage space. Bathrooms, laundry, and the entire upper level have all been thoughtfully renovated. Situated

  Kenneth Kauzlarich RE/MAX Precision

  901 E Buchanan St, Winterset, IA 50273
• 

  

  /22

  $525,000 Sold Jul 08, 2025

  1785 Millstream Ct, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,911 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $275/SF
  • 98 Days On Market

  Current Estimated Value $557,704

  Last Listing Agent JoAnn Manning Iowa Realty Mills Crossing

  1785 Millstream Ct, Winterset, IA 50273

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