4,174

Winterset, IA Homes

Section Image
  • 524 W Benton St, Winterset, IA 50273
    524 W Benton St, Winterset, IA 50273
    524 W Benton St, Winterset, IA 50273
    /34

    $260,000

    Sold Jun 29, 2026

    524 W Benton St, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,705 Sq Ft
    • Built 1964

    Last Sold Summary

    • 5% Below List Price
    • $152/SF
    • 24 Days On Market

    Current Estimated Value $273,686

    Last Listing Agent Jennifer Stover Madison County Realty

    524 W Benton St, Winterset, IA 50273
    • 222 W Summit St, Winterset, IA 50273
      222 W Summit St, Winterset, IA 50273
      222 W Summit St, Winterset, IA 50273
      /22

      Est $171,394

      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

      • 4 Days On Market

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

    $364,900

    $34K PRICE DROP
    • 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
  • 409 W Filmore St, Winterset, IA 50273
    409 W Filmore St, Winterset, IA 50273
    409 W Filmore St, Winterset, IA 50273
    /32

    $176,500

    Sold Aug 29, 2025

    409 W Filmore St, Winterset, IA 50273

    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft
    • Built 1900

    Last Sold Summary

    • 5% Below List Price
    • $148/SF
    • 67 Days On Market

    Current Estimated Value $177,898

    Last Listing Agent Misty Darling BH&G Real Estate Innovations

    409 W Filmore St, Winterset, IA 50273
    • 604 S 2nd Ave, Winterset, IA 50273
      604 S 2nd Ave, Winterset, IA 50273
      604 S 2nd Ave, Winterset, IA 50273
      /18

      Est $279,700

      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

      • 70 Days On Market

  • 415 E Buchanan St, Winterset, IA 50273
    415 E Buchanan St, Winterset, IA 50273
    415 E Buchanan St, Winterset, IA 50273
    /17

    $154,000

    $11K PRICE DROP
    • 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
  • 604 E Jefferson St, Winterset, IA 50273
    604 E Jefferson St, Winterset, IA 50273
    604 E Jefferson St, Winterset, IA 50273
    /23

    $162,500

    Sold Jun 02, 2026

    604 E Jefferson St, Winterset, IA 50273

    • 3 Beds
    • 1.5 Baths
    • 1,306 Sq Ft
    • Built 1896

    Last Sold Summary

    • 10% Below List Price
    • $124/SF
    • 60 Days On Market

    Current Estimated Value $172,614

    Last Listing Agent Toni Tindle Covered Bridge Realty

    604 E Jefferson St, Winterset, IA 50273
    • 421 E Court Ave, Winterset, IA 50273
      421 E Court Ave, Winterset, IA 50273
      421 E Court Ave, Winterset, IA 50273
      /23

      Est $226,862

      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

      • 76 Days On Market

  • 5219 Cherrywood Ln, Winterset, IA 50273
    5219 Cherrywood Ln, Winterset, IA 50273
    5219 Cherrywood Ln, Winterset, IA 50273
    /34

    $565,000

    • 4 Beds
    • 3 Baths
    • 1,506 Sq Ft

    5219 Cherrywood Ln, Winterset, IA 50273

    Stunning 4 bed (5 non-conforming) 3 bath home nestled on 2.24 acres! Walking in you are instantly drawn to over-sized windows showcasing a beautiful backyard. Home features 2x6 exterior walls & 9' ceilings. Kitchen has 11' long single piece quartz island w/ double-sided cabinets that demands its own zip code. A large walk-in pantry & custom built wood shelving and all appliances included complete

    Jonathan Lee RE/MAX Precision

    5219 Cherrywood Ln, Winterset, IA 50273
  • 2283 Clark Tower Rd, Winterset, IA 50273
    2283 Clark Tower Rd, Winterset, IA 50273
    2283 Clark Tower Rd, Winterset, IA 50273
    /35

    $575,000

    Sold Sep 30, 2025

    2283 Clark Tower Rd, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 2022

    Last Sold Summary

    • 15% Below List Price
    • $319/SF
    • 29 Days On Market

    Current Estimated Value $565,470

    Last Listing Agent Marcus Sereg Iowa Realty South

    2283 Clark Tower Rd, Winterset, IA 50273
    • 716 E Filmore St, Winterset, IA 50273
      716 E Filmore St, Winterset, IA 50273
      716 E Filmore St, Winterset, IA 50273
      /25

      Est $218,978

      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

      • 179 Days On Market

  • 802 N 10th Ave, Winterset, IA 50273
    802 N 10th Ave, Winterset, IA 50273
    802 N 10th Ave, Winterset, IA 50273
    /28

    $455,000

    Pending
    • 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
  • Lot 20 112th Ct, Winterset, IA 50273
    Lot 20 112th Ct, Winterset, IA 50273
    Lot 20 112th Ct, Winterset, IA 50273
    /7

    $199,000

    Sold Jan 08, 2026

    Lot 20 112th Ct, Winterset, IA 50273

    • Land
    • 3.15 Acres
    • $63,175 per Acre

    Last Sold Summary

    • 20% Below List Price
    • 413 Days On Market

    Last Listing Agent Julie Baudler RE/MAX Concepts

    Lot 20 112th Ct, Winterset, IA 50273
    • 117 E High St, Winterset, IA 50273
      117 E High St, Winterset, IA 50273
      117 E High St, Winterset, IA 50273
      /33

      Est $305,362

      Not Listed For Sale

      117 E High St, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2020
      117 E High St, Winterset, IA 50273

      Last Sold Summary

      • 9 Days On Market

  • Lot 26 114th Ct, Winterset, IA 50273
    Lot 26 114th Ct, Winterset, IA 50273
    Lot 26 114th Ct, Winterset, IA 50273
    /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
  • 623 W Green St, Winterset, IA 50273
    623 W Green St, Winterset, IA 50273
    623 W Green St, Winterset, IA 50273
    /13

    $298,000

    Sold May 22, 2026

    623 W Green St, Winterset, IA 50273

    • 4 Beds
    • 3 Baths
    • 1,464 Sq Ft
    • Built 1977

    Last Sold Summary

    • 5% Below List Price
    • $204/SF
    • 55 Days On Market

    Current Estimated Value $308,544

    Last Listing Agent Markjon Trierweiler RE/MAX Precision

    623 W Green St, Winterset, IA 50273
    • 721 E High St, Winterset, IA 50273
      721 E High St, Winterset, IA 50273
      721 E High St, Winterset, IA 50273
      /27

      Est $193,956

      Not Listed For Sale

      721 E High St, Winterset, IA 50273

      • 2 Beds
      • 1 Bath
      • 1,168 Sq Ft
      • Built 1957
      721 E High St, Winterset, IA 50273

      Last Sold Summary

      • 130 Days On Market

  • Lot 29 Limestone Ct, Winterset, IA 50273
    Lot 29 Limestone Ct, Winterset, IA 50273
    Lot 29 Limestone Ct, Winterset, IA 50273
    /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
  • Lot 18 114th Ct, Winterset, IA 50273
    Lot 18 114th Ct, Winterset, IA 50273
    Lot 18 114th Ct, Winterset, IA 50273
    /7

    $240,000

    Sold Feb 27, 2026

    Lot 18 114th Ct, Winterset, IA 50273

    • Land
    • 3.75 Acres
    • $64,000 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 445 Days On Market

    Last Listing Agent Julie Baudler RE/MAX Concepts

    Lot 18 114th Ct, Winterset, IA 50273
    • 823 E Jefferson St, Winterset, IA 50273
      823 E Jefferson St, Winterset, IA 50273
      823 E Jefferson St, Winterset, IA 50273
      /17

      Est $184,069

      Not Listed For Sale

      823 E Jefferson St, Winterset, IA 50273

      • 2 Beds
      • 1.5 Baths
      • 780 Sq Ft
      • Built 1957
      823 E Jefferson St, Winterset, IA 50273

      Last Sold Summary

      • 7 Days On Market

  • 2259 Cedar Bridge Rd, Winterset, IA 50273
    2259 Cedar Bridge Rd, Winterset, IA 50273
    2259 Cedar Bridge Rd, Winterset, IA 50273
    /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
  • 000 Ivy Trail, Winterset, IA 50273
    000 Ivy Trail, Winterset, IA 50273
    000 Ivy Trail, Winterset, IA 50273
    /20

    $167,500

    Sold Mar 27, 2026

    000 Ivy Trail, Winterset, IA 50273

    • Land
    • 13.6 Acres
    • $12,316 per Acre

    Last Sold Summary

    • 25% Below List Price
    • 722 Days On Market

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    000 Ivy Trail, Winterset, IA 50273
    • 223 N 8th St, Winterset, IA 50273
      223 N 8th St, Winterset, IA 50273
      223 N 8th St, Winterset, IA 50273
      /8

      Est $183,320

      Not Listed For Sale

      223 N 8th St, Winterset, IA 50273

      • 3 Beds
      • 1 Bath
      • 1,048 Sq Ft
      • Built 1952
      223 N 8th St, Winterset, IA 50273

      Last Sold Summary

      • 5 Days On Market

  • 1473 280th St, Winterset, IA 50273
    1473 280th St, Winterset, IA 50273
    1473 280th St, Winterset, IA 50273
    /35

    $395,000

    • 4 Beds
    • 3 Baths
    • 2,576 Sq Ft

    1473 280th St, Winterset, IA 50273

    Sitting on 4.96± acres in the countryside of Madison County, this Amish-built home offers the perfect opportunity to create your dream rural retreat. Built in 2018, the 2,576 sq. ft. home features 4 bedrooms, 3 bathrooms, vaulted ceilings, and a unique natural tree centerpiece. The home offers a durable metal exterior and roof, spray-foam insulation, rural water, plumbing, propane, hot water

    Will Cooper Midwest Land Group LLC

    1473 280th St, Winterset, IA 50273
  • 1806 N 8th Ave, Winterset, IA 50273
    1806 N 8th Ave, Winterset, IA 50273
    1806 N 8th Ave, Winterset, IA 50273
    /35

    $475,000

    Sold May 29, 2026

    1806 N 8th Ave, Winterset, IA 50273

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • Built 1910

    Last Sold Summary

    • $265/SF
    • 14 Days On Market

    Current Estimated Value $467,775

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    1806 N 8th Ave, Winterset, IA 50273
    • 217 N 7th St, Winterset, IA 50273
      217 N 7th St, Winterset, IA 50273
      217 N 7th St, Winterset, IA 50273
      /18

      Est $201,505

      Not Listed For Sale

      217 N 7th St, Winterset, IA 50273

      • 3 Beds
      • 1 Bath
      • 1,477 Sq Ft
      • Built 1890
      217 N 7th St, Winterset, IA 50273

      Last Sold Summary

      • 83 Days On Market

  • 1624 W Summit St Unit 134, Winterset, IA 50273
    1624 W Summit St Unit 134, Winterset, IA 50273
    1624 W Summit St Unit 134, Winterset, IA 50273
    /7

    $36,900

    • 2 Beds
    • 1 Bath

    1624 W Summit St Unit 134, Winterset, IA 50273

    This 2 bedroom, 1 bathroom home is a comfy, with an eat in kitchen with an island. This home has a NEW roof, plenty of windows, with newer blinds, that provides the home with natural light. The living room is very spacious in this home. The bathroom is conveniently located between both bedrooms for great efficiency.

    Angie Standlee Covered Bridges MHP

    1624 W Summit St Unit 134, Winterset, IA 50273
  • 215 W Filmore St, Winterset, IA 50273
    215 W Filmore St, Winterset, IA 50273
    215 W Filmore St, Winterset, IA 50273
    /19

    $62,500

    Sold Aug 29, 2025

    215 W Filmore St, Winterset, IA 50273

    • 3 Beds
    • 1.5 Baths
    • 1,186 Sq Ft
    • Built 1890

    Last Sold Summary

    • 50% Below List Price
    • $53/SF
    • 166 Days On Market

    Current Estimated Value $139,810

    Last Listing Agent Steven Camerona Iowa Realty Beaverdale

    215 W Filmore St, Winterset, IA 50273
    • 609 E Jefferson St, Winterset, IA 50273
      609 E Jefferson St, Winterset, IA 50273
      609 E Jefferson St, Winterset, IA 50273
      /13

      Est $184,597

      Not Listed For Sale

      609 E Jefferson St, Winterset, IA 50273

      • 2 Beds
      • 1 Bath
      • 1,060 Sq Ft
      • Built 1919
      609 E Jefferson St, Winterset, IA 50273

      Last Sold Summary

      • 47 Days On Market

  • Lot 15 114th Ct, Winterset, IA 50273
    Lot 15 114th Ct, Winterset, IA 50273
    Lot 15 114th Ct, Winterset, IA 50273
    /7

    $285,000

    Pending
    • Land
    • 3.11 Acres
    • $91,640 per Acre

    Lot 15 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 15 114th Ct, Winterset, IA 50273
  • 322 N 15th Ave, Winterset, IA 50273
    322 N 15th Ave, Winterset, IA 50273
    322 N 15th Ave, Winterset, IA 50273
    /23

    $255,000

    Sold Jul 25, 2025

    322 N 15th Ave, Winterset, IA 50273

    • 3 Beds
    • 2.5 Baths
    • 1,438 Sq Ft
    • Built 2003

    Last Sold Summary

    • 14% Below List Price
    • $177/SF
    • 42 Days On Market

    Current Estimated Value $270,042

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    322 N 15th Ave, Winterset, IA 50273
    • 720 N 3rd St, Winterset, IA 50273
      720 N 3rd St, Winterset, IA 50273
      720 N 3rd St, Winterset, IA 50273
      /29

      Est $258,302

      Not Listed For Sale

      720 N 3rd St, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1969
      720 N 3rd St, Winterset, IA 50273

      Last Sold Summary

      • 63 Days On Market

  • Lot 32 Limestone Ct, Winterset, IA 50273
    Lot 32 Limestone Ct, Winterset, IA 50273
    Lot 32 Limestone Ct, Winterset, IA 50273
    /7

    $325,000

    • Land
    • 9.2 Acres
    • $35,326 per Acre

    Lot 32 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 32 Limestone Ct, Winterset, IA 50273
  • 408 E Benton St, Winterset, IA 50273
    408 E Benton St, Winterset, IA 50273
    408 E Benton St, Winterset, IA 50273
    /18

    $162,500

    Sold Sep 26, 2025

    408 E Benton St, Winterset, IA 50273

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Built 1956

    Last Sold Summary

    • 19% Below List Price
    • $212/SF
    • 103 Days On Market

    Current Estimated Value $154,378

    Last Listing Agent Jamie Adkins RE/MAX Precision

    408 E Benton St, Winterset, IA 50273
    • 703 N 3rd Ave, Winterset, IA 50273
      703 N 3rd Ave, Winterset, IA 50273
      703 N 3rd Ave, Winterset, IA 50273
      /21

      Est $232,130

      Not Listed For Sale

      703 N 3rd Ave, Winterset, IA 50273

      • 3 Beds
      • 1 Bath
      • 960 Sq Ft
      • Built 1976
      703 N 3rd Ave, Winterset, IA 50273

      Last Sold Summary

      • 107 Days On Market

  • 2210 Ash Tree Dr, Winterset, IA 50273
    2210 Ash Tree Dr, Winterset, IA 50273
    /2

    $395,000

    $3K PRICE INCREASE Pending
    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    2210 Ash Tree Dr, Winterset, IA 50273

    Jackson Walkout Ranch Plan with over-sized 3 car garage. Front porch with 2 stone base posts. 9' ceilings throughout main floor. Open stairs to basement. Granite or quartz counter tops in baths and kitchen. Kitchen boasts a large walk-in pantry and stainless-steel appliances. White painted maple cabinets throughout. Luxury vinyl flooring. 60 inch gas fireplace. Master bath with raised vanity and

    Robert D. Weeks Iowa Realty Waukee

    2210 Ash Tree Dr, Winterset, IA 50273
  • 2218 N John Wayne Dr, Winterset, IA 50273
    2218 N John Wayne Dr, Winterset, IA 50273
    2218 N John Wayne Dr, Winterset, IA 50273
    /34

    $580,000

    Sold Mar 17, 2026

    2218 N John Wayne Dr, Winterset, IA 50273

    • 3 Beds
    • 3.5 Baths
    • 3,298 Sq Ft
    • Built 1988

    Last Sold Summary

    • 14% Below List Price
    • $176/SF
    • 92 Days On Market

    Last Listing Agent Alyssa Tadlock Madison County Realty

    2218 N John Wayne Dr, Winterset, IA 50273
    • 323 W Benton St, Winterset, IA 50273
      323 W Benton St, Winterset, IA 50273
      323 W Benton St, Winterset, IA 50273
      /30

      Est $244,623

      Not Listed For Sale

      323 W Benton St, Winterset, IA 50273

      • 3 Beds
      • 1.5 Baths
      • 1,381 Sq Ft
      • Built 1906
      323 W Benton St, Winterset, IA 50273

      Last Sold Summary

      • 8 Days On Market

  • 1509 State 92 Hwy, Winterset, IA 50273
    1509 State 92 Hwy, Winterset, IA 50273
    1509 State 92 Hwy, Winterset, IA 50273
    /31

    $370,000

    $30K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,680 Sq Ft

    1509 State 92 Hwy, Winterset, IA 50273

    Step back in time and imagine the possibilities with this classic farmhouse nestled on 3.82 scenic acres surrounded by mature timber and peaceful countryside views. Built in 1925, this 2-story home offers 1,680 square feet filled with original character and timeless charm. Inside, you’ll find 4 bedrooms, a home office, beautiful original trim, stunning French doors in the dining room and living

    Jennifer Stover Madison County Realty

    1509 State 92 Hwy, Winterset, IA 50273
  • 1221 W Washington St, Winterset, IA 50273
    1221 W Washington St, Winterset, IA 50273
    1221 W Washington St, Winterset, IA 50273
    /18

    $212,000

    Sold May 28, 2026

    1221 W Washington St, Winterset, IA 50273

    • 2 Beds
    • 1 Bath
    • 816 Sq Ft
    • Built 1974

    Last Sold Summary

    • 8% Below List Price
    • $260/SF
    • 82 Days On Market

    Current Estimated Value $213,068

    Last Listing Agent Jennifer Stover Madison County Realty

    1221 W Washington St, Winterset, IA 50273

Showing Results 241 - 280, Page 7 of 18

Iowa Madison County Winterset

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