Saint Charles, IA Homes

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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 $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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  /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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  /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
• 

  

  

  /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
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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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  /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
• 

  

  /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
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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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  /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
• 

  

  /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
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  /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
• 

  

  /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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  /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
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  /34

  $349,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,833 Sq Ft

  724 W Buchanan St, Winterset, IA 50273

  Completely renovated 4-bedroom, 2-bath home featuring extensive interior and exterior improvements, along with major structural upgrades that provide long-term peace of mind. Thoughtfully updated from top to bottom, the home offers all new flooring throughout, creating a seamless and modern feel across the main living areas, bedrooms, and finished basement. The bathrooms have been fully remodeled

  Ben Flurey A.I.M. Real Estate & Consultin

  724 W Buchanan St, 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
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  /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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  /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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  /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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  /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
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  /35

  $340,000

  • 5 Beds
  • 2.5 Baths
  • 2,217 Sq Ft

  621 W Jefferson St, Winterset, IA 50273

  Step into timeless charm with this deceptively spacious 1903 home, perfectly situated on a corner lot along the picturesque, tree-lined W. Jefferson Street—just blocks from the square in Winterset. From the moment you arrive, the inviting front porch sets the tone for relaxed mornings, evening conversations, and a true sense of home. Inside, you’ll find the perfect blend of character and modern

  Jennifer Stover Madison County Realty

  621 W Jefferson 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
• 

  

  /17

  Est $299,488 Not Listed For Sale

  802 N 4th Ave, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1960

  802 N 4th Ave, Winterset, IA 50273

  Last Sold Summary

  • 4% Above List Price
  • $285/SF
  • 71 Days On Market

  Last Sold Price $287,000

  Last Listing Agent Lissa Baker RE/MAX
• 

  

  /23

  $290,000

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

  410 N 6th St, Winterset, IA 50273

  Pride of ownership in this spacious home! 3 bedrooms, 2 baths, over 2,000 sf finished space and a huge backyard. Adorable kitchen with stainless steel appliances. Refrigerator is less than 1 year old. Large dining area with sliding door that leads to the deck/backyard. Great set up for the primary bedroom with access to the bathroom/laundry room. All 3 bedrooms are on the 1st floor. The lower

  Jennifer Stover Madison County Realty

  410 N 6th St, Winterset, IA 50273
• 

  

  /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
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  /12

  Est $226,924 Not Listed For Sale

  1002 N 4th Ave, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,169 Sq Ft
  • Built 1974

  1002 N 4th Ave, Winterset, IA 50273

  Last Sold Summary

  • 19% Above List Price
  • $163/SF
  • 8 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Jennifer Stover Madison County Realty
• 

  

  /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
• 

  

  /34

  Est $280,755 Not Listed For Sale

  201 S 14th Ave, Winterset, IA 50273

  • 5 Beds
  • 2.5 Baths
  • 1,372 Sq Ft
  • Built 1978

  201 S 14th Ave, Winterset, IA 50273

  Last Sold Summary

  • 15% Above List Price
  • $179/SF
  • 28 Days On Market

  Last Sold Price $245,000

  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
• 

  

  /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
• 

  

  /29

  Est $469,088 Not Listed For Sale

  1515 W Washington St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 2,484 Sq Ft
  • Built 1978

  1515 W Washington St, Winterset, IA 50273

  Last Sold Summary

  • 13% Above List Price
  • $167/SF
  • 23 Days On Market

  Last Sold Price $415,000

  Last Listing Agent Andrew Algreen Keller Williams Realty GDM
• 

  

  /35

  $650,000

  • Land
  • 4.6 Acres
  • $141,304 per Acre

  2223 Holliwell Valley Ct, Winterset, IA 50273

  This exceptional walkout ranch presents an extraordinary opportunity for those seeking space, comfort, and country charm. Situated on over four and a half acres of stunning Iowa countryside, the home boasts more than three thousand square feet of beautifully finished living space with four bedrooms and four bathrooms. The open floorplan and wall of windows make the main level light, bright and

  Melissa Hatchitt Zealty Home Advisors

  2223 Holliwell Valley Ct, 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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  /32

  Est $471,625 Not Listed For Sale

  924 Husky Dr, Winterset, IA 50273

  • 5 Beds
  • 3 Baths
  • 2,051 Sq Ft
  • Built 2004

  924 Husky Dr, Winterset, IA 50273

  Last Sold Summary

  • 14% Above List Price
  • $203/SF
  • 537 Days On Market

  Last Sold Price $415,500

  Last Listing Agent Betsy Breeding Realty ONE Group Impact
• 

  

  /35

  $560,000

  • Land
  • 4.29 Acres
  • $130,536 per Acre

  2237 Holliwell Valley Ct, Winterset, IA 50273

  If you are dreaming of countryside peace and quiet and need alot of living space, you will definately enjoy the beauty and freedom of a 4.3-acre homestead featuring 6 bedrooms, 4 baths, and multiple living areas. The elegant kitchen boasts a walk-in pantry, an abundance of countertop and cabinet space, and picturesque views of rolling hills and a neighboring pond. Step out from the dining area

  Sarah Cowman Homefront Real Estate, LLC

  2237 Holliwell Valley Ct, Winterset, IA 50273
• 

  

  /35

  $300,000 Sold Nov 03, 2025

  2385 Holliwell Bridge Rd, Winterset, IA 50273

  • Land
  • 3.17 Acres
  • $94,637 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 73 Days On Market

  Current Estimated Value $278,287

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  2385 Holliwell Bridge Rd, Winterset, IA 50273
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  /26

  Est $292,412 Not Listed For Sale

  803 S 3rd St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1961

  803 S 3rd St, Winterset, IA 50273

  Last Sold Summary

  • 6% Above List Price
  • $286/SF
  • 212 Days On Market

  Last Sold Price $274,900

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /35

  $455,000

  • Land
  • 3 Acres
  • $151,667 per Acre

  2075 Hogback Bridge Rd, Winterset, IA 50273

  Acreages this close to the town of Winterset are extremely hard to find, but finding one engineered to this standard is nearly impossible. This expansive 2,568 sq. ft. homestead on 3 pristine acres features 3 bedrooms, 3 bathrooms, and a large kitchen designed with plenty of storage and a sprawling floor plan for the active country lifestyle. The home features spray foam insulation throughout the

  Ian Sparks Homefront Real Estate, LLC

  2075 Hogback Bridge Rd, Winterset, IA 50273
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  /29

  $174,900 Sold Jun 03, 2025

  501 W Summit St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $223/SF
  • 18 Days On Market

  Current Estimated Value $176,649

  Last Listing Agent Rachel Eller Summerset Realty

  501 W Summit St, Winterset, IA 50273

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