Winterset, IA Homes

• 

  

  

  /35

  $225,000

  $30K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 962 Sq Ft

  710 N 3rd Ave, Winterset, IA 50273

  Corner lot three-bedroom, one bath ranch with attached garage on Winterset West side. Home has fenced yard, great fire pit area for outdoor entertaining, contained decorative garden/flower beds and a row of new trees. Other new yard features include landscaping rock and creative oval garden landscaping mound. Updates include fully encapsulated deep crawl space with warranty and new sump pump.

  

  Toni Tindle

  Covered Bridge Realty

  710 N 3rd Ave, Winterset, IA 50273
• Explore Winterset

• 

  

  

  /21

  Starting at $1,035 Per Month

  • 3 Beds

  1407 W Mills St, Winterset, IA 50273

  Cherry Creek

  

  1407 W Mills St, Winterset, IA 50273
• 

  

  

  /35

  $299,000

  Sold Feb 03, 2026

  724 W Jefferson St, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 1898

  Last Sold Summary

  • 15% Below List Price
  • $123/SF
  • 228 Days On Market

  Current Estimated Value $306,090

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  724 W Jefferson St, Winterset, IA 50273
• 

  

  

  /24

  Est $343,756

  Not Listed For Sale

  701 E Madison St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 2018

  701 E Madison St, Winterset, IA 50273

  Last Sold Summary

  • 21 Days On Market
• 

  

  

  /35

  $410,000

  $64K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,389 Sq Ft

  1913 N 1st St, Winterset, IA 50273

  Hard to find home on this parcel just N of Winterset 4-way intersection of Hwy 92 & 169. This home has 3BR's & 3 baths sitting proudly on nearly 1 acre. Kitchen has had a complete remodel including adding a convenient island & farm sink. Master/BR on 1st floor has large walk-in closet, & tiled walk-in shower. Main floor laundry off the kitchen. Other features on the 1st level include a formal

  

  Toni Tindle

  Covered Bridge Realty

  1913 N 1st St, Winterset, IA 50273
• 

  

  /10

  Starting at $545 Per Month

  • Studio - 2 Beds

  110 W Washington St, Winterset, IA 50273

  Call today to learn more about Historic Winterset High School Apartments Senior 55+ , NOW LEASING for June 1, 2024!

  Historic Winterset High School Apartments 55+

  

  110 W Washington St, Winterset, IA 50273
• 

  

  /31

  $260,000

  Sold Apr 30, 2026

  901 E Buchanan St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,323 Sq Ft
  • Built 1880

  Last Sold Summary

  • 2% Below List Price
  • $197/SF
  • 4 Days On Market

  Current Estimated Value $260,388

  Last Listing Agent Kenneth Kauzlarich RE/MAX Precision

  901 E Buchanan St, Winterset, IA 50273
• 

  

  /35

  Est $521,963

  Not Listed For Sale

  2364 Bittersweet Ave, Winterset, IA 50273

  • 3 Beds
  • 3 Baths
  • 1,312 Sq Ft
  • Built 2013

  2364 Bittersweet Ave, Winterset, IA 50273

  Last Sold Summary

  • 2 Days On Market
• 

  

  /21

  $169,000

  • 3 Beds
  • 1 Bath
  • 1,523 Sq Ft

  118 N 5th St, Winterset, IA 50273

  Charm with economy! That's what this 5BR, 1 bath, 1.5 story home offers! Great natural light from the large east-facing picture window in the living room. There are 3 bedrooms on the main level, along with the full bath. The open carpeted stairway will lead you to the 2 non-conforming bedrooms (no closets) on the 2nd level. Easy-to-clean laminate flooring throughout main level. The main floor

  

  Toni Tindle

  Covered Bridge Realty

  118 N 5th St, Winterset, IA 50273
• 

  

  /14

  $950 Per Month

  • 1 Bed
  • 600 Sq Ft
  • House for Rent

  59 W Jefferson St, Winterset, IA 50273

  Available immediately is a large sunny apartment located on the square in Winterset, above the US Cellular store. The best part of this quiet unit is the stunning view of the Madison County Courthouse out of the two large front windows. There is an extra-large eat-in kitchen with a pantry, large bathroom and a huge storage closet. The beautiful hardwood floors and the unique antique pocket doors

  Rachel Eller Summerset Realty

  59 W Jefferson St, Winterset, IA 50273
• 

  /2

  $85,000

  Sold Nov 13, 2025

  315 E Green St, Winterset, IA 50273

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft
  • Built 1938

  Last Sold Summary

  • 15% Below List Price
  • $118/SF
  • 0 Days On Market

  Current Estimated Value $113,059

  Last Listing Agent Betsy Breeding Realty ONE Group Impact

  315 E Green St, Winterset, IA 50273
• 

  

  /17

  Est $225,735

  Not Listed For Sale

  2430 Highway 169, Winterset, IA 50273

  • Built 2000

  2430 Highway 169, Winterset, IA 50273

  Last Sold Summary

  • 333 Days On Market
• 

  

  /29

  $190,000

  • 3 Beds
  • 1 Bath
  • 1,926 Sq Ft

  415 N 1st Ave, Winterset, IA 50273

  Just blocks from Winterset’s historic square, this 1.5-story home blends charm with everyday function. A wraparound porch (swing included) sets the tone before you even walk in. Inside, a bright living room with a cozy fireplace opens into an eat-in kitchen with white cabinetry, stainless appliances, and a walk-in pantry. All three bedrooms sit on the main level, along with a full bath and

  

  Darson Grantham

  Keller Williams Realty GDM

  415 N 1st Ave, Winterset, IA 50273
• 

  

  /11

  $820 Per Month

  • 2 Beds
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  517 N John Wayne Dr Unit 6, Winterset, IA 50273

  Nice 2 Bedroom 1 Bath apartment with coin laundry in each building. New Oak kitchen. Stove refrigerator and dishwasher included. Landlord pays heat water and trash. Tenant pays electric. Each unit has a through the wall AC for those warm summer days. Great small town near enough to Des Moines to enjoy perks of big city if desired. We require: Each adult to apply with $40 fee, Verifiable

  517 N John Wayne Dr Unit 6, Winterset, IA 50273
• 

  

  /32

  $265,000

  Sold Nov 19, 2025

  620 W Filmore St, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,741 Sq Ft
  • Built 1947

  Last Sold Summary

  • 11% Below List Price
  • $152/SF
  • 164 Days On Market

  Current Estimated Value $261,345

  Last Listing Agent Alyssa Tadlock Madison County Realty

  620 W Filmore St, Winterset, IA 50273
• 

  

  /22

  Est $575,174

  Not Listed For Sale

  1785 Millstream Ct, Winterset, IA 50273

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

  1785 Millstream Ct, Winterset, IA 50273

  Last Sold Summary

  • 98 Days On Market
• 

  

  /27

  $325,000

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

  511 W Washington St, Winterset, IA 50273

  Welcoming 1 1⁄2 story brick home on Winterset West side. Recent remodel, galley kitchen, main floor bedroom and full bath. Living room open to dining area. Handy drop zone near rear door from detached garage. Full unfinished basement with included washer and dryer and 1⁄2 bath with a bonus laundry sink and workshop area. Three bedrooms on the second level hardwood floors and full bath upstairs.

  

  Toni Tindle

  Covered Bridge Realty

  511 W Washington St, Winterset, IA 50273
• 

  

  /6

  $1,500 Per Month

  • 2 Beds
  • 2 Baths
  • Townhouse for Rent

  209 W Jefferson St, Winterset, IA 50273

  Discover the charm of historic Winterset, Iowa—home of the iconic Bridges of Madison County. Just steps from the beautifully restored town square, this location places you within walking distance of cafés, shops, museums, parks, and local wineries. Enjoy a vibrant community rich in history, seasonal festivals, and small-town warmth. Explore the scenic countryside and covered bridges by day, then

  209 W Jefferson St, Winterset, IA 50273
• 

  /2

  $285,000

  Sold May 15, 2026

  816 N 3rd Ave, Winterset, IA 50273

  • Studio
  • 1,385 Sq Ft
  • Built 2005

  Last Sold Summary

  • $206/SF
  • 0 Days On Market

  Current Estimated Value $287,444

  Last Listing Agent Toni Tindle Covered Bridge Realty

  816 N 3rd Ave, Winterset, IA 50273
• 

  

  /22

  Est $270,881

  Not Listed For Sale

  616 E Green St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1968

  616 E Green St, Winterset, IA 50273

  Last Sold Summary

  • 2 Days On Market
• 

  

  /31

  $225,000

  • 2 Beds
  • 1.5 Baths
  • 1,148 Sq Ft

  215 E Filmore St, Winterset, IA 50273

  Just listed: Winterset modestly priced ranch-style home.This property features two bedrooms, one full bathroom, and a partial bath located off the laundry room. The home offers easy entry through an enclosed front porch with a closet.The interior includes a large open kitchen and dining area. All kitchen appliances are included. For outdoor living and dining, sliders from the kitchen lead

  

  Toni Tindle

  Covered Bridge Realty

  215 E Filmore St, Winterset, IA 50273
• 

  

  /7

  $119,000

  Sold Nov 14, 2025

  Lot 36 Limestone Ct, Winterset, IA 50273

  • Land
  • 2.95 Acres
  • $40,339 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 341 Days On Market

  Last Listing Agent Julie Baudler RE/MAX Concepts

  Lot 36 Limestone Ct, Winterset, IA 50273
• 

  

  /23

  Est $185,072

  Not Listed For Sale

  513 W Hutchings St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 958 Sq Ft
  • Built 1890

  513 W Hutchings St, Winterset, IA 50273

  Last Sold Summary

  • 4 Days On Market
• 

  

  /35

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  3035 Clark Tower Rd, Winterset, IA 50273

  Rare opportunity to own a beautifully improved 24+/- acre pasture and timber farm less than 9 miles from Winterset on pavement. Built in 2023, the ranch home offers 5 bedrooms, 3 bathrooms, an additional non-conforming bedroom, 2,800 finished square feet, and an unfinished 2,800-square-foot basement ready for your finishing touches. The attached 2,685-square-foot, 3-door insulated garage features

  Aaron Creger Midwest Land Group LLC

  3035 Clark Tower Rd, Winterset, IA 50273
• 

  /2

  $339,000

  Sold Oct 24, 2025

  708 W Fremont St, Winterset, IA 50273

  • 4 Beds
  • 2.5 Baths
  • 2,026 Sq Ft
  • Built 1895

  Last Sold Summary

  • $167/SF
  • 1 Day On Market

  Current Estimated Value $342,225

  Last Listing Agent Rachel Eller Summerset Realty

  708 W Fremont St, Winterset, IA 50273
• 

  

  /21

  Est $218,921

  Not Listed For Sale

  915 E South St, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 1972

  915 E South St, Winterset, IA 50273

  Last Sold Summary

  • 47 Days On Market
• 

  

  /11

  $350,000

  • Land
  • 18.64 Acres
  • $18,777 per Acre

  0 Clark Tower Rd, Winterset, IA 50273

  Luxury Executive Acreage on Pavement | 18.64 Acres Just South of Winterset, Iowa Presenting a premier 18.64-acre executive acreage opportunity located just three miles south of Winterset on paved Clark Tower Road. Opportunities of this caliber in Madison County are increasingly difficult to find, offering the perfect combination of scenic beauty, privacy, usable land, and convenient access to the

  Andrew Zellmer Peoples Company

  0 Clark Tower Rd, Winterset, IA 50273
• 

  

  /35

  $1,235,000

  Sold Mar 20, 2026

  1890 Hogback Bridge Rd, Winterset, IA 50273

  • 5 Beds
  • 5 Baths
  • 4,032 Sq Ft
  • Built 2019

  Last Sold Summary

  • 11% Below List Price
  • $306/SF
  • 109 Days On Market

  Current Estimated Value $1,253,318

  Last Listing Agent Lenchen Raeside RE/MAX Concepts

  1890 Hogback Bridge Rd, Winterset, IA 50273
• 

  

  /19

  Est $201,465

  Not Listed For Sale

  706 N 1st Ave, Winterset, IA 50273

  • 3 Beds
  • 1.5 Baths
  • 1,216 Sq Ft
  • Built 1921

  706 N 1st Ave, Winterset, IA 50273

  Last Sold Summary

  • 109 Days On Market
• 

  

  /64

  $949,900

  $245K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,210 Sq Ft

  1524 260th St, Winterset, IA 50273

  DREAMS DO COME TRUE! Take a look at this exquisite 2 story home on 15ac in beautiful MADISON COUNTY. As soon as you walk in the door you will see what makes this home stand out. The CRAFTSMANSHIP is amazing, from the CUSTOM CABINETS, DOORS and COMMERCIAL EXHAUST VENT, all made on site, to the CUSTOM STEEL BACKSPLASH and BARN BOARDS from the old Homestead that was located on this acreage. The

  Betsy Breeding Realty ONE Group Impact

  1524 260th St, Winterset, IA 50273
• 

  

  /34

  $575,000

  Sold Sep 12, 2025

  711 E Madison St, Winterset, IA 50273

  • 5 Beds
  • 3 Baths
  • 1,739 Sq Ft
  • Built 2002

  Last Sold Summary

  • 4% Below List Price
  • $331/SF
  • 92 Days On Market

  Current Estimated Value $493,203

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  711 E Madison St, Winterset, IA 50273
• 

  

  /30

  Est $277,885

  Not Listed For Sale

  416 N 1st Ave, Winterset, IA 50273

  • 3 Beds
  • 2 Baths
  • 1,474 Sq Ft
  • Built 1887

  416 N 1st Ave, Winterset, IA 50273

  Last Sold Summary

  • 49 Days On Market
• 

  

  /35

  $1,099,000

  $151K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,282 Sq Ft

  1826 Green Ln, Winterset, IA 50273

  57.36 Acres with Log Home, Livestock Facilities & Equipment – Earlham School District Located just 3 miles north of Highway 92 and approximately 2 miles east of Earlham Road, this 57.36 gross acre property offers a great combination of rural living, pasture ground, and functional farm improvements. The property features a 2-story log cabin style home built in 1996 offering approximately 2,282

  Shane Spyksma Kiloterra

  1826 Green Ln, Winterset, IA 50273
• 

  

  /22

  $318,000

  Sold Jan 02, 2026

  2378 Francesca Ave, Winterset, IA 50273

  • Land
  • 26.47 Acres
  • $12,014 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 8 Days On Market

  Last Listing Agent Matt Skinner Iowa Land Company

  2378 Francesca Ave, Winterset, IA 50273
• 

  

  /34

  Est $263,338

  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

  • 22 Days On Market
• 

  

  /25

  $414,900

  $15K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,077 Sq Ft

  2607 Quail Ridge Trail, Winterset, IA 50273

  Set on 3 peaceful acres in Madison County, this charming 1.5-story farmhouse offers the perfect blend of country character, privacy and everyday function. With 2,077 square feet, the home features a warm farmhouse style throughout, including a farmhouse kitchen, inviting living spaces, 2 bathrooms, one bedroom on the main level, and three additional bedrooms upstairs.The sunroom overlooks the

  Julie Egli RE/MAX Precision

  2607 Quail Ridge Trail, Winterset, IA 50273
• 

  

  /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 $171,468

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  415 W Summit St, Winterset, IA 50273
• 

  

  /20

  Est $175,142

  Not Listed For Sale

  728 W Green St, Winterset, IA 50273

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

  728 W Green St, Winterset, IA 50273

  Last Sold Summary

  • 4 Days On Market
• 

  

  /29

  $260,000

  $10K PRICE DROP

  • Land
  • 10.23 Acres
  • $25,415 per Acre

  2212 Deer Run Ave, Winterset, IA 50273

  Have you been looking for the perfect country spot to build your dream home? This 10 acre lot has all of the infrastructure already in place. It is build-ready! $50,000 has been invested in the property for a building pad, water and electric brought from the road to the build site, new driveway, etc. A future barndominium or walkout home will enjoy rolling countryside views for miles.

  Jeffrey Longman RE/MAX Precision

  2212 Deer Run Ave, Winterset, IA 50273
• 

  

  /25

  $575,000

  Sold Nov 20, 2025

  2283 Pioneer Ave, Winterset, IA 50273

  • 5 Beds
  • 2 Baths
  • 2,074 Sq Ft
  • Built 1997

  Last Sold Summary

  • 7% Below List Price
  • $277/SF
  • 40 Days On Market

  Current Estimated Value $544,131

  Last Listing Agent Bryan Curtis Attain RE

  2283 Pioneer Ave, Winterset, IA 50273

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