Winterset, IA Homes

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  /35

  $226,900

  • 3 Beds
  • 1.5 Baths
  • 958 Sq Ft

  513 W Hutchings St, Winterset, IA 50273

  Step into this beautifully remodeled 2025 home complete with 3 bedrooms and 1.5 bathrooms. Thoughtfully updated throughout, this residence includes new sheet rock and fresh paint, new LVP flooring, new central air system and duct work, upgraded plumbing and electrical and all new windows. Lage kitchen features custom Amish-built cabinetry, quartz countertops and just around the corner a main

  

  Toni Tindle

  Covered Bridge Realty

  (515) 481-5094

  513 W Hutchings St, Winterset, IA 50273
• Explore Winterset

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  /20

  $995 per month

  Cherry Creek

  3 Beds

  1407 W Mills St, Winterset, IA 50273

  1407 W Mills St, Winterset, IA 50273
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  /25

  $164,000 Sold Apr 10, 2025

  509 W Summit St, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1885

  Last Sold Summary

  • 4% Below List Price
  • $190/SF
  • 128 Days On Market

  Current Estimated Value $163,726

  Last Listing Agent Austin Postier RE/MAX Results

  509 W Summit St, Winterset, IA 50273
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  /21

  Est $219,433 Not Listed For Sale

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

  915 E South St, Winterset, IA 50273

  915 E South St, Winterset, IA 50273
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  /31

  $259,000

  • 4 Beds
  • 2 Baths
  • 1,104 Sq Ft

  609 E Filmore St, Winterset, IA 50273

  Recently updated ranch style home with 4 bedrooms and 2 baths. Interior includes three BR’s on the main floor, living room, and kitchen just off attached one car garage. One bedroom on the main level would also make a perfect office space and was previously used as a sewing room. All bedrooms have generous sized closets. Updated kitchen with bright over the sink window facing south, included

  

  Toni Tindle

  Covered Bridge Realty

  (515) 373-5687

  609 E Filmore St, Winterset, IA 50273
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  /6

  $1,950 per month

  • 4 Beds
  • 1.5 Baths
  • 2,087 Sq Ft
  • House for Rent

  506 W Washington St, Winterset, IA 50273

  Nestled in the heart of the Winterset historic area is this classic American Foursquare with early Craftsman accents. A wonderful example of historic charm and contemporary finish, this home has been expertly maintained and superbly updated to reflect modern design tastes. The living room and dining area are warm and inviting gathering places. The completely remodeled kitchen has abundant

  Rachel Eller Summerset Realty

  506 W Washington St, Winterset, IA 50273
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  /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

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  724 W Jefferson St, Winterset, IA 50273
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  /34

  Est $267,026 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,050 Sq Ft

  203 W North St, Winterset, IA 50273

  203 W North St, Winterset, IA 50273
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  /28

  $142,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft

  207 E Buchanan St, Winterset, IA 50273

  Discover this inviting frame home located near the Winterset Square. The main level features a generous sized living room with an enclosed entryway, a full bathroom, and a main floor bedroom. The kitchen opens to the dining area, creating a warm and functional space for everyday living. Upstairs, you'll find two additional bedrooms, offering flexibility for family, guests, or a home office. The

  

  Toni Tindle

  Covered Bridge Realty

  (515) 493-7698

  207 E Buchanan St, Winterset, IA 50273
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  /10

  $545 - $790 per month

  Historic Winterset High School Apartments 55+

  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!

  110 W Washington St, Winterset, IA 50273
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  /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 $100,614

  Last Listing Agent Betsy Breeding Realty ONE Group Impact

  315 E Green St, Winterset, IA 50273
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  /35

  Est $589,252 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths

  2064 226th Ct, Winterset, IA 50273

  2064 226th Ct, Winterset, IA 50273
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  /35

  $450,000

  • 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

  (515) 824-5239

  1913 N 1st St, Winterset, IA 50273
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  /30

  $181,000 Sold May 12, 2025

  712 N 2nd Ave, Winterset, IA 50273

  • 3 Beds
  • 1 Bath
  • 1,358 Sq Ft
  • Built 1905

  Last Sold Summary

  • 19% Below List Price
  • $133/SF
  • 207 Days On Market

  Current Estimated Value $178,968

  Last Listing Agent Toni Tindle Covered Bridge Realty

  712 N 2nd Ave, Winterset, IA 50273
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  /35

  Est $548,206 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  2395 148th St, Winterset, IA 50273

  2395 148th St, Winterset, IA 50273
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  /26

  $205,000

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

  827 W Fremont St, Winterset, IA 50273

  Just listed . . . . townhome in the West End Townhomes located off W Fremont Street in Winterset. E-Z access as you enter the quiet cul-de-sac with circle drive designed with room for additional parking. Two-bedroom two bath home with 1,213 square feet of finish on the main level. Large well-lit living room has gas log fireplace as a focal point. An adjacent walk-in coat closet with shelving is

  

  Toni Tindle

  Covered Bridge Realty

  (515) 575-2601

  827 W Fremont St, Winterset, IA 50273
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  /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 $260,296

  Last Listing Agent Alyssa Tadlock Madison County Realty

  620 W Filmore St, Winterset, IA 50273
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  /33

  Est $408,000 Not Listed For Sale

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

  906 N 14th Ave, Winterset, IA 50273

  906 N 14th Ave, Winterset, IA 50273
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  /4

  $275,000

  • Land
  • 10.23 Acres
  • $26,882 per Acre

  2212 Deer Run Ave, Winterset, IA 50273

  Don't miss this rare opportunity to own 10 acres m/l of picturesque countryside just 8 miles west of Winterset, situated on a hard surface road and a prime corner lot. This walkout lot is ready for your dream home with rural water, electricity, and a driveway already added, saving you the time and expense of major improvements. The gently rolling terrain offers stunning views and the perfect

  

  Chris Kew

  RE/MAX Precision

  (515) 230-0488

  2212 Deer Run Ave, Winterset, IA 50273
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  /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
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  /23

  Est $349,541 Not Listed For Sale

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

  807 N 15th Ave, Winterset, IA 50273

  807 N 15th Ave, Winterset, IA 50273
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  /12

  $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

  (515) 882-4007

  118 N 5th St, Winterset, IA 50273
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  /31

  $395,000 Sold Jun 16, 2025

  2923 N John Wayne Dr, Winterset, IA 50273

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

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Rachel Eller Summerset Realty

  2923 N John Wayne Dr, Winterset, IA 50273
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  /35

  Est $397,360 Not Listed For Sale

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

  905 N 15th Ave, Winterset, IA 50273

  905 N 15th Ave, Winterset, IA 50273
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  /33

  $478,750

  • Land
  • 5 Acres
  • $95,750 per Acre

  2980 Clark Tower Rd, Winterset, IA 50273

  Located in scenic Madison County this newly built home and buildings offers peace and quiet with close commute to Winterset and West Des Moines. Located on hard surface road 8.5 miles south of Winterset. The home offers 2 bedrooms and 2 baths. The main floor offers an open concept with a nice main living and dining area. The upstairs offers the opportunity to expand to increase finished square

  Luke Skinner Iowa Land Company

  2980 Clark Tower Rd, Winterset, IA 50273
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  /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 $335,986

  Last Listing Agent Rachel Eller Summerset Realty

  708 W Fremont St, Winterset, IA 50273
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  /35

  Est $534,417 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,692 Sq Ft

  909 N 9th Ave, Winterset, IA 50273

  909 N 9th Ave, Winterset, IA 50273
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  /25

  $190,000 Pending

  • Land
  • 4.88 Acres
  • $38,934 per Acre

  4922 Cedar Ln, Winterset, IA 50273

  This 4.88-acre lot sits at the end of a quiet cul-de-sac and offers a great mix of open ground and mature hardwood timber. It’s the kind of setting that gives you room to spread out without losing that classic Madison County charm. There’s plenty of space here for a custom home, a shop, or whatever else you’ve been dreaming about building. The location is hard to beat—peaceful and private, but

  Will Cooper Midwest Land Group LLC

  4922 Cedar Ln, Winterset, IA 50273
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  /26

  $243,500 Sold Feb 21, 2025

  708 N 4th Ave, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 1,830 Sq Ft
  • Built 1917

  Last Sold Summary

  • 5% Below List Price
  • $133/SF
  • 10 Days On Market

  Current Estimated Value $249,688

  Last Listing Agent Sonny Greene Iowa Realty Mills Crossing

  708 N 4th Ave, Winterset, IA 50273
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  /17

  Est $290,998 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,344 Sq Ft

  809 W Mills St, Winterset, IA 50273

  809 W Mills St, Winterset, IA 50273
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  /11

  $372,750

  • Land
  • 18.64 Acres
  • $19,997 per Acre

  0 Clark Tower Rd, Winterset, IA 50273

  Premium Executive Building Lot on Pavement | Just South of Winterset, Iowa Peoples Company is proud to represent the Utsler Family Trust in the sale of an exceptional 18.64-acre executive building lot located just 3 miles south of Winterset, Iowa, with direct access off paved Clark Tower Road. This recently surveyed property offers the rare combination of privacy, premium views, utilities at

  Andrew Zellmer Peoples Company

  0 Clark Tower Rd, Winterset, IA 50273
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  /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 $535,054

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  711 E Madison St, Winterset, IA 50273
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  /28

  Est $218,325 Not Listed For Sale

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

  829 W Fremont St, Winterset, IA 50273

  829 W Fremont St, Winterset, IA 50273
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  /28

  $354,900

  • 4 Beds
  • 2.5 Baths
  • 1,333 Sq Ft

  215 W Buchanan St, Winterset, IA 50273

  Better than new, this fully renovated home offers 1,700+ total finished square feet and is truly move-in ready. This 4-bedroom, 3-bath property blends modern style with small-town charm in a mature, established neighborhood. Everything is brand new — electrical, plumbing, HVAC, drywall, trim, doors, windows, paint, flooring, kitchen, bathrooms, and more — but with the character and location you

  Elizabeth Gordon Realty ONE Group Impact

  215 W Buchanan St, Winterset, IA 50273
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  /2

  $335,000 Sold Apr 01, 2025

  322 W Jefferson St, Winterset, IA 50273

  • 4 Beds
  • 2 Baths
  • 2,990 Sq Ft
  • Built 1860

  Last Sold Summary

  • 4% Below List Price
  • $112/SF
  • 1 Day On Market

  Current Estimated Value $360,184

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  322 W Jefferson St, Winterset, IA 50273
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  /23

  Est $205,822 Not Listed For Sale

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

  911 N 6th Avenue Cir, Winterset, IA 50273

  911 N 6th Avenue Cir, Winterset, IA 50273
• 

  

  /23

  $309,900

  • 3 Beds
  • 1.5 Baths
  • 2,130 Sq Ft

  721 W Court Ave, Winterset, IA 50273

  Don't miss the opportunity to own this home on historical Court Avenue! You will love sitting on the wraparound porch for your morning coffee or just some time to relax. Upon entering the home, you will be impressed with the beautiful details of the open staircase. The first floor has a large living, family and dining rooms, 1/2 bath and kitchen. The hardwood floors and the woodwork are original

  Larry Corkrean Madison County Realty

  721 W Court Ave, Winterset, IA 50273
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  /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
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  /33

  Est $325,308 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,060 Sq Ft

  215 N 15th Ave, Winterset, IA 50273

  215 N 15th Ave, Winterset, IA 50273
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  /35

  $375,000

  • 4 Beds
  • 2 Baths
  • 2,724 Sq Ft

  615 N 1st Ave, Winterset, IA 50273

  This beautifully remodeled residence combines timeless charm with modern comfort. Step inside to discover hardwood floors and a striking, gracefully designed staircase that sets the tone for the entire home. The inviting front porch offers the perfect spot to welcome guests or enjoy peaceful evenings outdoors. Featuring four generously sized bedrooms plus a bonus room, and a full bath on each

  Sarah Cowman Homefront Real Estate, LLC

  615 N 1st Ave, Winterset, IA 50273

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