Saint Charles, 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
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  /25

  $995 per month

  3 Bedroom, Single-story Townhomes for rent in Winterset, IA

  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,

  1126 Dale Dr, 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 $171,374

  Last Listing Agent Austin Postier RE/MAX Results

  509 W Summit 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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  /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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  /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

  Last Listing Agent Betsy Breeding Realty ONE Group Impact

  315 E Green St, Winterset, IA 50273
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  /25

  Est $210,142 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft

  716 E Filmore St, Winterset, IA 50273

  716 E Filmore St, Winterset, IA 50273
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  /28

  $142,000

  • 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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  /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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  /30

  Est $190,152 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft

  406 N 7th St, Winterset, IA 50273

  406 N 7th St, Winterset, IA 50273
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  /35

  $225,000 Pending

  • 1 Bed
  • 2.5 Baths
  • 1,213 Sq Ft

  324 S 10th Ave, Winterset, IA 50273

  Ranch style Townhome on Winterset West side combines benefits of home ownership with low maintenance in a prime location. Large walk-in closet with window is conveniently located near the front door. Living room boasts a gas log fireplace as a classic feature. The kitchen has included appliances and abundant storage with two pantry cabinets and more. Dining area near kitchen leads to a bright 4

  

  Toni Tindle

  Covered Bridge Realty

  (515) 417-0598

  324 S 10th Ave, 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

  Last Listing Agent Alyssa Tadlock Madison County Realty

  620 W Filmore St, Winterset, IA 50273
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  /21

  Est $211,940 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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  /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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  /31

  $395,000 Sold Jun 16, 2025

  2923 N John Wayne Dr, Winterset, IA 50273

  • 4 Beds
  • 2.5 Baths
  • 1,518 Sq Ft
  • Built 1996

  Last Sold Summary

  • $260/SF
  • 67 Days On Market

  Last Listing Agent Rachel Eller Summerset Realty

  2923 N John Wayne Dr, Winterset, IA 50273
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  /34

  Est $233,984 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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  /26

  $212,500

  • 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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  /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

  Last Listing Agent Rachel Eller Summerset Realty

  708 W Fremont St, Winterset, IA 50273
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  /33

  Est $397,965 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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  /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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  /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 $524,678

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  711 E Madison St, Winterset, IA 50273
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  /23

  Est $345,818 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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  /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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  /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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  /35

  Est $375,137 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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  /35

  $315,000 Pending

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

  724 W Jefferson St, Winterset, IA 50273

  Prepare to be impressed with the renovations done to bring this stately home back to it's orignal glory! Step up to the inviting front covered porch & through the original leaded glass door into the stunning entryway showcasing the gorgeous stairway & original woodwork. The orignal hardwood floors flow throughout the entry room, HUGE living room, and into the formal dining room. Off the living

  Sarah Cowman Homefront Real Estate, LLC

  724 W Jefferson 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 $341,106

  Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

  322 W Jefferson St, Winterset, IA 50273
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  /35

  Est $512,872 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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  /35

  $1,385,000 Pending

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

  1890 Hogback Bridge Rd, Winterset, IA 50273

  Rare 30-acre M/L retreat in Madison County Iowa with a 4,000+ sq. ft. custom home. Incredible views of the countryside teeming with wildlife including white-tailed deer and turkey. Main level features gourmet kitchen with 2 dishwashers & walk-in pantry, spacious living areas, and a primary suite with sitting room, spa bath, huge walk-in closet & laundry. Upstairs offers loft with wet bar, 4

  Lenchen Raeside RE/MAX Concepts

  1890 Hogback Bridge Rd, Winterset, IA 50273
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  /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

  Last Listing Agent Misty Darling BH&G Real Estate Innovations

  415 W Summit St, Winterset, IA 50273
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  /17

  Est $279,835 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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  /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 Winterset home is truly move in ready. This 4-bedroom, 3-bath home (1,333 sq ft above grade + 409 sq ft finished basement) combines 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

  Elizabeth Gordon Realty ONE Group Impact

  215 W Buchanan St, Winterset, IA 50273
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  /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

  Last Listing Agent Bryan Curtis Attain RE

  2283 Pioneer Ave, Winterset, IA 50273
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  /25

  Est $216,093 Not Listed For Sale

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

  821 W Fremont St, Winterset, IA 50273

  821 W Fremont St, Winterset, IA 50273
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  /26

  $404,900

  • 4 Beds
  • 4 Baths
  • 2,460 Sq Ft

  1011 N 14th Ave, Winterset, IA 50273

  Discover your own slice of heaven right in town! This inviting two-story home is set in a friendly neighborhood where there's plenty of room to play and grow. The thoughtful layout makes the most of every square foot, creating spaces that work well for everyday life. The main level welcomes you with a handy drop zone, half bath, and a office with French doors. The open kitchen and family room are

  Michelle Hanson RE/MAX Concepts

  1011 N 14th Ave, Winterset, IA 50273
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  /27

  $269,000 Sold Oct 16, 2025

  822 N 3rd Ave, Winterset, IA 50273

  • 2 Beds
  • 2 Baths
  • 1,406 Sq Ft
  • Built 2005

  Last Sold Summary

  • $191/SF
  • 4 Days On Market

  Last Listing Agent Bruce Seymour RE/MAX Precision

  822 N 3rd Ave, Winterset, IA 50273
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  /23

  Est $205,196 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
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  /35

  $575,000

  • 6 Beds
  • 4 Baths
  • 3,155 Sq Ft

  2237 Holliwell Valley Ct, Winterset, IA 50273

  If you are dreaming of countryside peace and quiet and need alot of living space, you will definately enjoy the beauty and freedom of a 4.3-acre homestead featuring 6 bedrooms, 4 baths, and multiple living areas. The elegant kitchen boasts a walk-in pantry, an abundance of countertop and cabinet space, and picturesque views of rolling hills and a neighboring pond. Step out from the dining area

  Sarah Cowman Homefront Real Estate, LLC

  2237 Holliwell Valley Ct, Winterset, IA 50273

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