Winterset, IA Homes

• 

  

  

  /35

  $219,900

  $35K PRICE DROP Pending

  • 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

• 

  

  

  /20

  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 $306,818

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  724 W Jefferson St, Winterset, IA 50273
• 

  

  

  /26

  Est $318,727

  Not Listed For Sale

  902 W Filmore St, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2008

  902 W Filmore St, Winterset, IA 50273

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Betsy Breeding Realty ONE Group Impact
• 

  

  

  /31

  $215,000

  $10K PRICE DROP

  • 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
• 

  

  /20

  Starting at $995 Per Month

  • 3 Beds

  1126 Dale Dr, Winterset, IA 50273

  This comfortable property features three bedrooms, one full bath, and a laundry room with washer and dryer hook-ups. A one car garage is attached to the property for convenience and direct access to your kitchen. This property is located in Winterset and we have other properties with the same floor plan in Stuart, Indianola, & Osceola. Most communities are within walking distance to schools,

  Glenwood Villas

  

  1126 Dale Dr, 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 $262,641

  Last Listing Agent Kenneth Kauzlarich RE/MAX Precision

  901 E Buchanan St, Winterset, IA 50273
• 

  

  /23

  Est $186,428

  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

  Last Listing Agent Toni Tindle Covered Bridge Realty
• 

  

  /35

  $375,000

  $99K 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
• 

  /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
• 

  

  /21

  Est $226,858

  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

  Last Listing Agent Shannon Thompson Our Town Realty, LLC
• 

  

  /35

  $365,000

  Pending

  • 4 Beds
  • 3 Baths
  • 1,524 Sq Ft

  1405 W Court Ave, Winterset, IA 50273

  Step inside and you'll be welcomed by a spacious entry that opens into the vaulted living room, where a cozy fireplace creates the perfect gathering space. This well-maintained ranch offers over 2,500 finished square feet, 4 bedrooms, and 3 bathrooms. The spacious kitchen features maple cabinetry, newer granite countertops, updated appliances, and large windows that showcase views of the

  

  Lauren Moore

  Agency Iowa

  1405 W Court Ave, Winterset, IA 50273
• 

  

  /11

  $820 Per Month

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

  517 N John Wayne Dr Unit 24, 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 24, 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 $272,292

  Last Listing Agent Alyssa Tadlock Madison County Realty

  620 W Filmore St, Winterset, IA 50273
• 

  

  /19

  Est $214,798

  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

  Last Listing Agent Eric Vetsch Keller Williams Realty GDM
• 

  

  /35

  $254,000

  • 4 Beds
  • 1 Bath
  • 1,338 Sq Ft

  703 E Filmore St, Winterset, IA 50273

  Proudly sitting on a corner lot with many all-new features in 2026. It's a perfect blend of the past and present Be the first to live in this newly remodeled home with all new light fixtures, a larger kitchen, added bedroom closet storage, fresh paint, new hardware, smart siding, metal roof and more. Four-bedroom home with one BR on the main floor and 3 bedrooms on the second level. Large living

  

  Toni Tindle

  Covered Bridge Realty

  703 E Filmore St, Winterset, IA 50273
• 

  

  /11

  $820 Per Month

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

  517 N John Wayne Dr Unit 24, 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 24, 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 $282,443

  Last Listing Agent Toni Tindle Covered Bridge Realty

  816 N 3rd Ave, Winterset, IA 50273
• 

  

  /30

  Est $276,069

  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

  Last Listing Agent Rachel Eller Summerset Realty
• 

  

  /31

  $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
• 

  

  /13

  $1,500 Per Month

  • 2 Beds
  • 2 Baths
  • Townhouse for Rent

  209 W Jefferson St, Winterset, IA 50273

  JW Flats-Luxury Downtown Living in the Heart of WintersetExperience refined, maintenance-free living at JW Flats, a luxury condominium community in the heart of historic downtown Winterset, Iowa. Built in 1995, JW Flats offers spacious one- and two-bedroom residences thoughtfully designed for comfort, convenience, and modern living.Just one block from Winterset's charming town

  209 W Jefferson 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
• 

  

  /34

  Est $254,319

  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

  Last Listing Agent Rachel Eller Summerset Realty
• 

  

  /27

  $320,000

  $5K PRICE DROP

  • 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
• 

  /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
• 

  

  /20

  Est $164,780

  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

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /35

  $699,000

  Pending

  • 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
• 

  

  /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 $1,217,804

  Last Listing Agent Lenchen Raeside RE/MAX Concepts

  1890 Hogback Bridge Rd, Winterset, IA 50273
• 

  

  /35

  Est $623,908

  Not Listed For Sale

  2064 226th Ct, Winterset, IA 50273

  • 4 Beds
  • 3.5 Baths
  • 2,549 Sq Ft
  • Built 2006

  2064 226th Ct, Winterset, IA 50273

  Last Sold Summary

  • 136 Days On Market

  Last Listing Agent Jennifer Stover Madison County Realty
• 

  

  /61

  $478,577

  • Land
  • 68.86 Acres
  • $6,950 per Acre

  1479 280th St, Winterset, IA 50273

  Located northeast of Macksburg and southwest of Winterset, this 68.86-acre m/l Madison County farm offers an excellent combination of CRP income, mature timber, wildlife habitat, and recreation. The property includes 46.71 acres enrolled in CRP, generating $11,052 annually through September 30, 2033. The balance of the farm features substantial timber and wooded cover, creating outstanding

  Garret Armstrong Whitetail Properties Real Estate, LLC

  1479 280th 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 $508,965

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  711 E Madison St, Winterset, IA 50273
• 

  

  /33

  Est $401,088

  Not Listed For Sale

  906 N 14th Ave, Winterset, IA 50273

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft
  • Built 2005

  906 N 14th Ave, Winterset, IA 50273

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Betsy Breeding Realty ONE Group Impact
• 

  

  /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
• 

  

  /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
• 

  

  /23

  Est $354,121

  Not Listed For Sale

  807 N 15th Ave, Winterset, IA 50273

  • 4 Beds
  • 3 Baths
  • 1,273 Sq Ft
  • Built 2007

  807 N 15th Ave, Winterset, IA 50273

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC
• 

  

  /28

  $4,938,450

  • Land
  • 451.34 Acres
  • $10,942 per Acre

  00 N River School Rd, Winterset, IA 50273

  Peoples Company is proud to present the Hogback Farm, an exceptional 451 acre m/l recreational and income-producing property located in the heart of Madison County, Iowa, just a short drive from the Des Moines metro. Tucked into a highly desirable corridor between the vibrant and growing communities of Winterset and Adel, less than one mile from paved US Highway 169, this property offers a rare

  Bryan Bergdale Peoples Company

  00 N River School Rd, 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 $170,990

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  415 W Summit St, Winterset, IA 50273
• 

  

  /35

  Est $384,310

  Not Listed For Sale

  905 N 15th Ave, Winterset, IA 50273

  • 5 Beds
  • 2.5 Baths
  • 1,504 Sq Ft
  • Built 2005

  905 N 15th Ave, Winterset, IA 50273

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Ian Sparks Homefront Real Estate, LLC
• 

  

  /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

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