Winterset, IA Homes

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  /32

  $315,000 Sold Jan 27, 2026

  1541 Nature Ct, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $216/SF
  • 47 Days On Market

  Current Estimated Value $317,677

  Last Listing Agent Elizabeth Gordon Realty ONE Group Impact

  1541 Nature Ct, Winterset, IA 50273
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  /31

  Est $273,911 Not Listed For Sale

  524 W Hutchings St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1962

  524 W Hutchings St, Winterset, IA 50273

  Last Sold Summary

  • 8% Above List Price
  • $250/SF
  • 50 Days On Market

  Last Sold Price $252,500

  Last Listing Agent Toni Tindle Covered Bridge Realty
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  /7

  $240,000

  • Land
  • 4.19 Acres
  • $57,279 per Acre

  Lot 17 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 17 114th Ct, Winterset, IA 50273
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  /7

  $199,000 Sold Oct 28, 2025

  Lot 21 112th Ct, Winterset, IA 50273

  • Land
  • 3.37 Acres
  • $59,050 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 326 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 21 112th Ct, 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
• 

  

  /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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  /3

  $220,000 Sold Sep 15, 2025

  825 W Fremont St, Winterset, IA 50273

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

  Last Sold Summary

  • 2% Below List Price
  • $181/SF
  • 3 Days On Market

  Current Estimated Value $218,523

  Last Listing Agent Randall Henry Madison County Realty

  825 W Fremont St, Winterset, IA 50273
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  /26

  Est $218,666 Not Listed For Sale

  502 E Washington St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft
  • Built 1895

  502 E Washington St, Winterset, IA 50273

  Last Sold Summary

  • 11% Above List Price
  • $142/SF
  • 4 Days On Market

  Last Sold Price $197,500

  Last Listing Agent Kyle Kuhns RE/MAX Revolution
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  /7

  $194,000

  • Land
  • 2.96 Acres
  • $65,541 per Acre

  Lot 24 112th 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 24 112th Ct, Winterset, IA 50273
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  /7

  $125,000 Sold Nov 21, 2025

  Lot 4 114th Ct, Winterset, IA 50273

  • Land
  • 2.95 Acres
  • $42,373 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 363 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 4 114th Ct, Winterset, IA 50273
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  /15

  Est $257,911 Not Listed For Sale

  418 E Buchanan St, Winterset, IA 50273

  • 4 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Built 1979

  418 E Buchanan St, Winterset, IA 50273

  Last Sold Summary

  • 10% Above List Price
  • $196/SF
  • 7 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Nick Stephenson Realty ONE Group Impact
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  /7

  $220,000

  • Land
  • 4.22 Acres
  • $52,133 per Acre

  Lot 31 Limestone 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 31 Limestone Ct, Winterset, IA 50273
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  /21

  $221,100 Sold Feb 20, 2026

  110 E Grade St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,174 Sq Ft
  • Built 1904

  Last Sold Summary

  • 2% Below List Price
  • $188/SF
  • 111 Days On Market

  Current Estimated Value $218,606

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  110 E Grade St, Winterset, IA 50273
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  /17

  Est $194,352 Not Listed For Sale

  523 N 5th St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft
  • Built 1905

  523 N 5th St, Winterset, IA 50273

  Last Sold Summary

  • 14% Above List Price
  • $176/SF
  • 146 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Robert Duff Covered Bridge Realty
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  /7

  $250,000

  • Land
  • 3.33 Acres
  • $75,075 per Acre

  Lot 22 112th 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 22 112th Ct, Winterset, IA 50273
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  /33

  $217,000 Sold Apr 13, 2026

  705 S 2nd St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 2,085 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Below List Price
  • $104/SF
  • 46 Days On Market

  Current Estimated Value $230,476

  Last Listing Agent Kyle Kuhns RE/MAX Revolution

  705 S 2nd St, Winterset, IA 50273
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  /28

  Est $264,382 Not Listed For Sale

  719 S 7th Ave, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,170 Sq Ft
  • Built 1975

  719 S 7th Ave, Winterset, IA 50273

  Last Sold Summary

  • 12% Above List Price
  • $202/SF
  • 134 Days On Market

  Last Sold Price $236,000

  Last Listing Agent Rachel Eller Summerset Realty
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  /4

  $74,500

  • Land
  • 3 Acres
  • $24,833 per Acre

  1796 Millstream Ct, Winterset, IA 50273

  Beautiful 3-acre lot located in the desirable Covered Bridge Estates! This scenic property offers the perfect blend of country feel with community convenience. Ideal for building your dream home with room to spread out—bring your own builder! Enjoy paved roads, rural water access at the road, and peaceful surroundings in this established neighborhood. Just minutes from town, with easy access to

  Rachel Eller Summerset Realty

  1796 Millstream Ct, Winterset, IA 50273
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  /32

  $160,000 Sold Jul 08, 2025

  415 E Jefferson St, Winterset, IA 50273

  • 4 Beds
  • 1.5 Baths
  • 2,018 Sq Ft
  • Built 1922

  Last Sold Summary

  • 6% Below List Price
  • $79/SF
  • 41 Days On Market

  Current Estimated Value $185,634

  Last Listing Agent Betsy Breeding Realty ONE Group Impact

  415 E Jefferson St, Winterset, IA 50273
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  /22

  Est $187,857 Not Listed For Sale

  829 S 7th Ave, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 902 Sq Ft
  • Built 1870

  829 S 7th Ave, Winterset, IA 50273

  Last Sold Summary

  • 13% Above List Price
  • $185/SF
  • 11 Days On Market

  Last Sold Price $166,750

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /35

  $399,000

  • 4 Beds
  • 3.5 Baths
  • 1,720 Sq Ft

  704 N 14th Ave, Winterset, IA 50273

  Tucked at the end of a quiet street, this 4-bedroom home sits on an oversized lot in a welcoming neighborhood. You'll love the fully fenced yard, wooden fencing, and large deck, perfect for enjoying the outdoors.Inside, the main level offers a functional layout with a drop zone at the front entry, a dedicated office/study, and a spacious living area with a cozy fireplace. The kitchen features

  Ashlee & Kyle Knickerbocker Keller Williams Realty GDM

  704 N 14th Ave, Winterset, IA 50273
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  /33

  $220,000 Sold Aug 26, 2025

  1755 280th St, Winterset, IA 50273

  • Land
  • 2.5 Acres
  • $88,000 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 85 Days On Market

  Current Estimated Value $181,664

  Last Listing Agent Toni Tindle Covered Bridge Realty

  1755 280th St, Winterset, IA 50273
• 

  

  /29

  Est $317,357 Not Listed For Sale

  621 S 8th Ave, Winterset, IA 50273

  • 4 Beds
  • 2.5 Baths
  • 1,284 Sq Ft
  • Built 1968

  621 S 8th Ave, Winterset, IA 50273

  Last Sold Summary

  • 6% Above List Price
  • $234/SF
  • 28 Days On Market

  Last Sold Price $299,900

  Last Listing Agent Danielle Burnight RE/MAX
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  /17

  $165,000

  • 2 Beds
  • 1 Bath
  • 1,286 Sq Ft

  415 E Buchanan St, Winterset, IA 50273

  Affordable, fully updated and ready-to-move-in ranch in the heart of Winterset! Offering 1,286 sq ft, this home features a well-designed main-level layout with comfortable living space and a first-floor bedroom. Enjoy the added charm of a 3-season room perfect for relaxing or entertaining. Equipped with natural gas heating, city water and sewer, and included kitchen appliances for added

  Anagha Berodia Iowa Realty Waukee

  415 E Buchanan St, Winterset, IA 50273
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  /20

  $125,000 Sold May 20, 2025

  728 W Green St, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 1,255 Sq Ft
  • Built 1896

  Last Sold Summary

  • 12% Below List Price
  • $100/SF
  • 4 Days On Market

  Current Estimated Value $139,551

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  728 W Green St, Winterset, IA 50273
• 

  

  /22

  Est $185,936 Not Listed For Sale

  222 W Summit St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,038 Sq Ft
  • Built 1900

  222 W Summit St, Winterset, IA 50273

  Last Sold Summary

  • 13% Above List Price
  • $159/SF
  • 4 Days On Market

  Last Sold Price $164,900

  Last Listing Agent Kyle Kuhns RE/MAX Revolution
• 

  

  /28

  $455,000

  • 4 Beds
  • 3 Baths
  • 1,555 Sq Ft

  802 N 10th Ave, Winterset, IA 50273

  Easy living in this open floor plan ranch home. A large covered front porch greets you as you enter the foyer. There is a nice drop zone for coats and shoes. The living room is very spacious and has a stunning gas fireplace. The kitchen is bright and features a breakfast bar and nice sized pantry. The dining is off the kitchen. The primary bedroom is large and has a huge bathroom with tile

  Sarah Cowman Homefront Real Estate, LLC

  802 N 10th Ave, Winterset, IA 50273
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  /27

  $495,000 Sold Dec 29, 2025

  2155 148th St, Winterset, IA 50273

  • Land
  • 4.19 Acres
  • $118,138 per Acre

  Last Sold Summary

  • 23% Below List Price
  • 45 Days On Market

  Current Estimated Value $494,269

  Last Listing Agent Cindy Miller Keller Williams Realty GDM

  2155 148th St, Winterset, IA 50273
• 

  

  /18

  Est $261,193 Not Listed For Sale

  604 S 2nd Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1977

  604 S 2nd Ave, Winterset, IA 50273

  Last Sold Summary

  • 3% Above List Price
  • $160/SF
  • 70 Days On Market

  Last Sold Price $252,500

  Last Listing Agent Jennifer Stover Madison County Realty
• 

  

  /30

  $490,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,540 Sq Ft

  400 N 14th Ave, Winterset, IA 50273

  This immaculate 4-bedroom, 2-bath ranch home perfectly blends modern comfort with timeless style. Built in 2013 and exceptionally cared for, every detail radiates warmth, quality, and convenience. Step inside to an inviting open layout highlighted floor-to-ceiling stone fireplace—a stunning centerpiece for cozy evenings or lively gatherings with family and friends. The beautiful kitchen is both

  Sarah Cowman Homefront Real Estate, LLC

  400 N 14th Ave, Winterset, IA 50273
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  /9

  $265,410 Sold Nov 26, 2025

  TBD Pioneer Ave, Winterset, IA 50273

  • Land
  • 29.49 Acres
  • $9,000 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 22 Days On Market

  Last Listing Agent Chris Wearmouth Kiloterra

  TBD Pioneer Ave, Winterset, IA 50273
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  /20

  Est $161,762 Not Listed For Sale

  401 S 2nd Ave, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1980

  401 S 2nd Ave, Winterset, IA 50273

  Last Sold Summary

  • 20% Above List Price
  • $141/SF
  • 12 Days On Market

  Last Sold Price $135,000

  Last Listing Agent Jacob Joliet Iowa Realty Mills Crossing
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  /7

  $215,000

  • Land
  • 2.91 Acres
  • $73,883 per Acre

  Lot 26 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 26 114th Ct, Winterset, IA 50273
• 

  

  /12

  $1,300,000 Sold Jul 17, 2025

  RR Millstream Ave, Winterset, IA 50273

  • Land
  • 172.1 Acres
  • $7,554 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 41 Days On Market

  Last Listing Agent Larry Corkrean Madison County Realty

  RR Millstream Ave, Winterset, IA 50273
• 

  

  /23

  Est $227,888 Not Listed For Sale

  421 E Court Ave, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 1,098 Sq Ft
  • Built 1905

  421 E Court Ave, Winterset, IA 50273

  Last Sold Summary

  • 2% Above List Price
  • $204/SF
  • 76 Days On Market

  Last Sold Price $224,500

  Last Listing Agent Alyssa Tadlock Madison County Realty
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  /7

  $230,000

  • Land
  • 3.3 Acres
  • $69,697 per Acre

  Lot 29 Limestone 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 29 Limestone Ct, Winterset, IA 50273
• 

  

  /31

  $226,000 Sold Aug 08, 2025

  318 W Green St, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $143/SF
  • 43 Days On Market

  Current Estimated Value $230,401

  Last Listing Agent Toni Tindle Covered Bridge Realty

  318 W Green St, Winterset, IA 50273
• 

  

  /25

  Est $215,324 Not Listed For Sale

  716 E Filmore St, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1992

  716 E Filmore St, Winterset, IA 50273

  Last Sold Summary

  • 3% Above List Price
  • $179/SF
  • 179 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Tanner Couch LPT Realty, LLC
• 

  

  /7

  $160,000

  • Land
  • 3.32 Acres
  • $48,193 per Acre

  2259 Cedar Bridge Rd, Winterset, IA 50273

  Introducing Five Iron Farms - Madison County's newest acreage subdivision. Five Iron Farms offers the best of both world: located in the city limits with city services, but also situated on 3+acres surrounded by farm ground with great views of the countryside. Located on a hard surface road and just down the road from Lakeview Country Club. Bring your own builder. A good reference address to use

  Jennifer Stover Madison County Realty

  2259 Cedar Bridge Rd, Winterset, IA 50273
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  /35

  $442,000 Sold May 09, 2025

  1410 W Washington St, Winterset, IA 50273

  • 5 Beds
  • 4.5 Baths
  • 2,000 Sq Ft
  • Built 1979

  Last Sold Summary

  • 12% Below List Price
  • $221/SF
  • 317 Days On Market

  Current Estimated Value $454,165

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  1410 W Washington St, Winterset, IA 50273

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