4,090

Winterset, IA Homes

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  • /35

    $775,000

    Sold May 21, 2026

    112 S 16th Ave, Winterset, IA 50273

    • 4 Beds
    • 4 Baths
    • 2,826 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $274/SF
    • 23 Days On Market

    Current Estimated Value $757,906

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    112 S 16th Ave, Winterset, IA 50273
    • /30

      Est $263,888

      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

      Last Listing Agent Betsy Breeding Realty ONE Group Impact

  • /4

    $55,000

    $20K PRICE DROP
    • Land
    • 3 Acres
    • $18,333 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! Limestone is present. Enjoy paved roads, rural water access at the road, and peaceful surroundings in this established neighborhood. Just minutes from town,

    Rachel Eller Summerset Realty

    1796 Millstream Ct, Winterset, IA 50273
  • /31

    $107,500

    Sold Nov 20, 2025

    59 E Washington St, Winterset, IA 50273

    • 2 Beds
    • 1 Bath
    • 942 Sq Ft
    • Built 1880

    Last Sold Summary

    • 19% Below List Price
    • $114/SF
    • 113 Days On Market

    Current Estimated Value $122,334

    Last Listing Agent John Brummett RE/MAX Precision

    59 E Washington St, Winterset, IA 50273
    • /35

      Est $339,466

      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

      • 103 Days On Market

      Last Listing Agent Adam Bugbee Real Broker, LLC

  • /33

    $350,000

    $49K PRICE DROP Pending
    • 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
  • /29

    $325,000

    Sold Nov 19, 2025

    916 W Filmore St, Winterset, IA 50273

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2014

    Last Sold Summary

    • $242/SF
    • 4 Days On Market

    Current Estimated Value $284,986

    Last Listing Agent Jennifer Stover Madison County Realty

    916 W Filmore St, Winterset, IA 50273
    • /19

      Est $180,424

      Not Listed For Sale

      65 E North St, Winterset, IA 50273

      • 3 Beds
      • 1 Bath
      • 1,334 Sq Ft
      • Built 1870
      65 E North St, Winterset, IA 50273

      Last Sold Summary

      • 182 Days On Market

      Last Listing Agent Jennifer Stover Madison County Realty

  • /34

    $559,000

    $6K PRICE DROP
    • 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
  • /25

    $180,000

    Sold Apr 08, 2026

    4922 Cedar Ln, Winterset, IA 50273

    • Land
    • 4.88 Acres
    • $36,885 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 7 Days On Market

    Current Estimated Value $178,787

    Last Listing Agent Will Cooper Midwest Land Group LLC

    4922 Cedar Ln, Winterset, IA 50273
    • /26

      Est $344,653

      Not Listed For Sale

      115 W North St, Winterset, IA 50273

      • 4 Beds
      • 3 Baths
      • 1,497 Sq Ft
      • Built 1999
      115 W North St, Winterset, IA 50273

      Last Sold Summary

      • 88 Days On Market

      Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  • /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
  • /29

    $242,000

    Sold Dec 12, 2025

    120 S 8th Ave, Winterset, IA 50273

    • 3 Beds
    • 2.5 Baths
    • 1,560 Sq Ft
    • Built 1967

    Last Sold Summary

    • 7% Below List Price
    • $155/SF
    • 52 Days On Market

    Current Estimated Value $273,104

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    120 S 8th Ave, Winterset, IA 50273
    • /29

      Est $298,871

      Not Listed For Sale

      311 W North St, Winterset, IA 50273

      • 3 Beds
      • 3 Baths
      • 1,388 Sq Ft
      • Built 2004
      311 W North St, Winterset, IA 50273

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Abbey Robertson Century 21 Signature

  • /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
  • /2

    $417,640

    Sold Aug 04, 2026

    309 Maple Pointe, Winterset, IA 50273

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2026

    Last Sold Summary

    • 9% Above List Price
    • $298/SF
    • 70 Days On Market

    Last Listing Agent Robert D. Weeks Iowa Realty Waukee

    309 Maple Pointe, Winterset, IA 50273
    • /23

      Est $205,543

      Not Listed For Sale

      324 W Filmore St, Winterset, IA 50273

      • 2 Beds
      • 2 Baths
      • 1,008 Sq Ft
      • Built 1956
      324 W Filmore St, Winterset, IA 50273

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Sarah Cowman Homefront Real Estate, 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
  • /34

    $655,000

    Sold Mar 23, 2026

    1821 Millstream Ct, Winterset, IA 50273

    • 4 Beds
    • 3.5 Baths
    • 2,200 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $298/SF
    • 219 Days On Market

    Current Estimated Value $660,728

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    1821 Millstream Ct, Winterset, IA 50273
    • /24

      Est $286,966

      Not Listed For Sale

      719 W Washington St, Winterset, IA 50273

      • 3 Beds
      • 1.5 Baths
      • 1,456 Sq Ft
      • Built 1903
      719 W Washington St, Winterset, IA 50273

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  • /29

    $210,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 964 Sq Ft

    110 N 10th Ave, Winterset, IA 50273

    Located in a desirable Winterset neighborhood, this ranch home offers hardwood floors throughout, three main floor bedrooms, an eat-in kitchen with plenty of countertop space, and two spacious family rooms, one on the main level and one in the finished lower level. The attached one-car garage is complemented by an additional parking pad for extra convenience. The lower level also provides

    Kyle Kuhns RE/MAX Revolution

    110 N 10th Ave, Winterset, IA 50273
  • /2

    $155,000

    Sold Jan 15, 2026

    00 Roseman Bridge Rd, Winterset, IA 50273

    • Land
    • 10 Acres
    • $15,500 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent Lauren Moore Agency Iowa

    00 Roseman Bridge Rd, Winterset, IA 50273
    • /20

      Est $308,364

      Not Listed For Sale

      316 S 7th Ave, Winterset, IA 50273

      • 3 Beds
      • 2 Baths
      • 1,483 Sq Ft
      • Built 2021
      316 S 7th Ave, Winterset, IA 50273

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Kristin Flaherty Stoney Oak Properties LLC

  • /34

    $469,900

    $5K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 1,807 Sq Ft

    305 Magnolia Point, Winterset, IA 50273

    If you are from Winterset, you know. If you are considering a move to Winterset, this town is one of the most beautiful ones in Iowa... the landscape, the hills - just incredibly picturesque. Then, you come upon 305 Magnolia Pt. A home built with care in 2023, requiring little maintenance. The thoughtful floor plan includes a mudroom area upon entering and a staircase staggered back a bit to

    Rachel Wallace RE/MAX Precision

    305 Magnolia Point, Winterset, IA 50273
  • /27

    $203,750

    Sold Mar 06, 2026

    821 W Fremont St, Winterset, IA 50273

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

    Last Sold Summary

    • 5% Below List Price
    • $168/SF
    • 16 Days On Market

    Current Estimated Value $208,016

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    821 W Fremont St, Winterset, IA 50273
    • /21

      Est $196,370

      Not Listed For Sale

      608 W South St, Winterset, IA 50273

      • 2 Beds
      • 1 Bath
      • 1,072 Sq Ft
      • Built 1926
      608 W South St, Winterset, IA 50273

      Last Sold Summary

      • 164 Days On Market

      Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  • /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.

    Mahayla Claiser Covered Bridges MHP

    1624 W Summit St Unit 134, Winterset, IA 50273
  • /17

    $170,000

    Sold Feb 02, 2026

    1022 W Washington St, Winterset, IA 50273

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft
    • Built 1970

    Last Sold Summary

    • 4% Below List Price
    • $182/SF
    • 4 Days On Market

    Current Estimated Value $182,062

    Last Listing Agent Matt Cole RE/MAX Concepts

    1022 W Washington St, Winterset, IA 50273
    • /32

      Est $320,472

      Not Listed For Sale

      612 W Jefferson St, Winterset, IA 50273

      • 3 Beds
      • 1.5 Baths
      • 1,976 Sq Ft
      • Built 1905
      612 W Jefferson St, Winterset, IA 50273

      Last Sold Summary

      • 77 Days On Market

      Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  • /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
  • /35

    $570,000

    Sold Mar 03, 2026

    1694 McBride Ridge Ct, Winterset, IA 50273

    • 4 Beds
    • 3 Baths
    • 1,878 Sq Ft
    • Built 2003

    Last Sold Summary

    • 12% Below List Price
    • $304/SF
    • 202 Days On Market

    Current Estimated Value $588,093

    Last Listing Agent Michelle Price Realty ONE Group Impact

    1694 McBride Ridge Ct, Winterset, IA 50273
    • /35

      Est $472,693

      Not Listed For Sale

      218 S 2nd Ave, Winterset, IA 50273

      • 4 Beds
      • 6 Baths
      • 3,325 Sq Ft
      • Built 1949
      218 S 2nd Ave, Winterset, IA 50273

      Last Sold Summary

      • 395 Days On Market

      Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  • /31

    $350,000

    $50K 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
  • /3

    $140,000

    Sold Jul 20, 2026

    1804 N 8th St, Winterset, IA 50273

    • Land
    • 3.68 Acres
    • $38,043 per Acre

    Last Sold Summary

    • 3 Days On Market

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    1804 N 8th St, Winterset, IA 50273
    • /34

      Est $311,770

      Not Listed For Sale

      211 W South St, Winterset, IA 50273

      • 3 Beds
      • 2.5 Baths
      • 1,904 Sq Ft
      • Built 1880
      211 W South St, Winterset, IA 50273

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Jennifer Mott RE/MAX Concepts

  • /31

    $249,999

    $65K PRICE DROP
    • 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
  • /22

    $212,000

    Sold Sep 29, 2025

    1424 W Jefferson St, Winterset, IA 50273

    • 3 Beds
    • 1 Bath
    • 1,088 Sq Ft
    • Built 1993

    Last Sold Summary

    • $195/SF
    • 3 Days On Market

    Current Estimated Value $210,472

    Last Listing Agent Rachel Eller Summerset Realty

    1424 W Jefferson St, Winterset, IA 50273
    • /35

      Est $479,286

      Not Listed For Sale

      220 W Washington St, Winterset, IA 50273

      • 4 Beds
      • 2 Baths
      • 4,315 Sq Ft
      • Built 1910
      220 W Washington St, Winterset, IA 50273

      Last Sold Summary

      • 616 Days On Market

      Last Listing Agent Jennifer Stover Madison County Realty

  • /2

    $395,000

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

    Lot 5 N 4th Ave, Winterset, IA 50273

    New Light Commercial Development. Lots will be ready to be built upon in Spring 2025, road pave in Fall 2024. All utilities to the lots. Great location for easy access to major highways. Listing agent has ownership in the property

    Peter Corkrean Madison County Realty

    Lot 5 N 4th Ave, Winterset, IA 50273
  • /35

    $317,500

    Sold Jul 10, 2026

    2197 175th Ct, Winterset, IA 50273

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft
    • Built 1978

    Last Sold Summary

    • 9% Below List Price
    • $310/SF
    • 49 Days On Market

    Current Estimated Value $336,502

    Last Listing Agent Ambria Vogt RE/MAX Precision

    2197 175th Ct, Winterset, IA 50273

Showing Results 281 - 320, Page 8 of 18

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