3,329

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

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 481-5094

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

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 373-5687

    609 E Filmore St, Winterset, IA 50273
  • /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
  • /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
    • /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
  • /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

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 493-7698

    207 E Buchanan St, Winterset, IA 50273
  • /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
  • /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
    • /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
  • /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

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 417-0598

    324 S 10th Ave, 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

    Last Listing Agent Alyssa Tadlock Madison County Realty

    620 W Filmore St, Winterset, IA 50273
    • /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
  • /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

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 824-5239

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

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 575-2601

    827 W Fremont 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

    Last Listing Agent Rachel Eller Summerset Realty

    708 W Fremont St, Winterset, IA 50273
    • /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
  • /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

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 882-4007

    118 N 5th 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 $524,678

    Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

    711 E Madison St, Winterset, IA 50273
    • /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
  • /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
  • /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
    • /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
  • /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
  • /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
    • /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
  • /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
  • /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
    • /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
  • /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
  • /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
    • /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
  • /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
  • /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
    • /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
  • /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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