Saint Charles, IA Homes

/33
$225,000 Pending
- 3 Beds
- 2 Baths
- 2,085 Sq Ft
705 S 2nd St, Winterset, IA 50273

Located in beautiful Winterset, IA, this well-maintained home offers over 2,000 square feet of comfortable living space. Featuring 3 bedrooms and 2 full bathrooms, the home includes a brand-new custom kitchen with updated cabinetry, perfect for everyday living and entertaining. Situated on a large lot with an oversized garage, there's plenty of room for storage, hobbies, and outdoor enjoyment. A

Kyle Kuhns RE/MAX Revolution

705 S 2nd St, Winterset, IA 50273
/35
$749,900 Sold Aug 15, 2025

4726 Cherrywood Ln, Winterset, IA 50273
- Land
- 2.92 Acres
- $256,815 per Acre
Last Sold Summary
- 5 Days On Market
Current Estimated Value $764,495

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

4726 Cherrywood Ln, Winterset, IA 50273

/26
Est $264,456 Not Listed For Sale

708 N 4th Ave, Winterset, IA 50273
- 4 Beds
- 2 Baths
- 1,830 Sq Ft
- Built 1917
708 N 4th Ave, Winterset, IA 50273

Last Sold Summary
- 9% Above List Price
- $133/SF
- 10 Days On Market
Last Sold Price $243,500

Last Listing Agent Sonny Greene Iowa Realty Mills Crossing

/12
$216,000
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
407 W Madison St, Winterset, IA 50273

Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower with tile surround and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet

Alyssa Tadlock Madison County Realty

407 W Madison St, Winterset, IA 50273
/28
$294,000 Sold Jun 02, 2025

1210 W Jefferson St, Winterset, IA 50273
- 3 Beds
- 2.5 Baths
- 1,464 Sq Ft
- Built 1992
Last Sold Summary
- $201/SF
- 6 Days On Market
Current Estimated Value $312,926

Last Listing Agent Ou Meksay RE/MAX Concepts

1210 W Jefferson St, Winterset, IA 50273

/26
Est $276,953 Not Listed For Sale

404 W Filmore St, Winterset, IA 50273
- 5 Beds
- 2 Baths
- 1,361 Sq Ft
- Built 1922
404 W Filmore St, Winterset, IA 50273

Last Sold Summary
- 10% Above List Price
- $185/SF
- 211 Days On Market
Last Sold Price $252,000

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

/34
$245,000
- 3 Beds
- 2 Baths
- 1,545 Sq Ft
114 N 8th Ave, Winterset, IA 50273

Completely updated 3-bedroom, 2-bath home blending timeless character with extensive upgrades! Original woodwork, detailed craftsmanship, and charming built-ins pair beautifully with newer hardwood floors (2022), granite countertops, stainless steel appliances, updated cabinetry, and tile flooring. The main level features a spacious living room with built-ins, formal dining room with classic

Kari Stone RE/MAX Precision

114 N 8th Ave, Winterset, IA 50273
/35
$295,000 Sold Sep 22, 2025

522 N 10th St, Winterset, IA 50273
- 3 Beds
- 2.5 Baths
- 1,972 Sq Ft
- Built 1991
Last Sold Summary
- 5% Below List Price
- $150/SF
- 25 Days On Market
Current Estimated Value $298,486

Last Listing Agent Kristen Stehli Real Broker, LLC

522 N 10th St, Winterset, IA 50273

/25
Est $185,688 Not Listed For Sale

809 E Benton St, Winterset, IA 50273
- 4 Beds
- 2 Baths
- 1,816 Sq Ft
- Built 1890
809 E Benton St, Winterset, IA 50273

Last Sold Summary
- 20% Above List Price
- $85/SF
- 17 Days On Market
Last Sold Price $155,000

Last Listing Agent Cody Bilyeu RE/MAX

/35
$449,900 Pending
- 5 Beds
- 3 Baths
- 2,137 Sq Ft
812 N 8th Ave, Winterset, IA 50273

Spacious and inviting, this large ranch in Winterset offers the perfect blend of comfort and style. You will love the stunning stone fireplace as the focal point in the living room with vaulted-ceilings, creating a warm and welcoming atmosphere. The kitchen is nice with granite countertops and plenty of cabinets. The primary bedroom is complete with an ensuite featuring a tile shower with dual

Matt Cole RE/MAX Concepts

812 N 8th Ave, Winterset, IA 50273
/19
$210,000 Sold Feb 27, 2026

2236 Carver Rd, Winterset, IA 50273
- 1 Bed
- 1 Sq Ft
- Built 2021
Last Sold Summary
- 9% Below List Price
- $210,000/SF
- 12 Days On Market
Current Estimated Value $228,564

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

2236 Carver Rd, Winterset, IA 50273

/16
Est $250,670 Not Listed For Sale

602 E Benton St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
- Built 1974
602 E Benton St, Winterset, IA 50273

Last Sold Summary
- 29% Above List Price
- $150/SF
- 278 Days On Market
Last Sold Price $195,000

Last Listing Agent Jamie Adkins RE/MAX

/12
$220,000
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
405 W Madison St, Winterset, IA 50273

Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower with tile surround and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet

Alyssa Tadlock Madison County Realty

405 W Madison St, Winterset, IA 50273
/35
$310,000 Sold Aug 07, 2025

522 N 7th Ave, Winterset, IA 50273
- 3 Beds
- 1.5 Baths
- 1,792 Sq Ft
- Built 1915
Last Sold Summary
- $173/SF
- 10 Days On Market
Current Estimated Value $317,821

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

522 N 7th Ave, Winterset, IA 50273

/20
Est $266,030 Not Listed For Sale

802 E Benton St, Winterset, IA 50273
- 4 Beds
- 2 Baths
- 924 Sq Ft
- Built 1975
802 E Benton St, Winterset, IA 50273

Last Sold Summary
- 14% Above List Price
- $252/SF
- 12 Days On Market
Last Sold Price $232,500

Last Listing Agent Kyle Kuhns RE/MAX Revolution

/7
$250,000
- Land
- 5.1 Acres
- $49,020 per Acre
2269 205th Ln, Winterset, IA 50273

Introducing Five Iron Farms - Madison County's newest acreage subdivision. Five Iron Farms offers the best of both world: located in the city limits with city services, but also situated on 3+acres surrounded by farm ground with great views of the countryside. Located on a hard surface road and just down the road from Lakeview Country Club. Bring your own builder. A good reference address to use

Jennifer Stover Madison County Realty

2269 205th Ln, Winterset, IA 50273
/17
$235,000 Sold Jun 20, 2025

2430 Highway 169, Winterset, IA 50273
- Land
- 35 Acres
- $6,714 per Acre
Last Sold Summary
- 60% Below List Price
- 333 Days On Market
Current Estimated Value $228,924

Last Listing Agent Keith Soldwisch Zealty Home Advisors

2430 Highway 169, Winterset, IA 50273

/16
Est $237,987 Not Listed For Sale

908 E Benton St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 796 Sq Ft
- Built 2006
908 E Benton St, Winterset, IA 50273

Last Sold Summary
- 1% Above List Price
- $295/SF
- 13 Days On Market
Last Sold Price $235,000

Last Listing Agent Tammy Heckart RE/MAX

/18
$223,000
- 2 Beds
- 1 Bath
- 816 Sq Ft
1221 W Washington St, Winterset, IA 50273

This super sweet ranch home makes a great starter home. The covered front porch is a great way to relax on the hot summer days. The first floor features a spacious kitchen, comfortable living room, 2 generous sized bedrooms and an updated full bath. The full basement is open and ready finish. The attached garage is heated and has access to the fenced backyard. The backyard features a large patio

Jennifer Stover Madison County Realty

1221 W Washington St, Winterset, IA 50273
/21
$180,000 Sold Nov 25, 2025

315 S 5th Ave, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 1977
Last Sold Summary
- 16% Below List Price
- $161/SF
- 41 Days On Market
Current Estimated Value $199,484

Last Listing Agent Dustin Crawford Iowa Home & Land Realty

315 S 5th Ave, Winterset, IA 50273

/24
Est $210,582 Not Listed For Sale

317 E North St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 840 Sq Ft
- Built 1994
317 E North St, Winterset, IA 50273

Last Sold Summary
- 15% Below List Price
- $295/SF
- 163 Days On Market
Last Sold Price $247,500

Last Listing Agent Rachel Eller Summerset Realty

/28
$274,900 Pending
- 3 Beds
- 2 Baths
- 864 Sq Ft
1509 W South St, Winterset, IA 50273

Move-in ready and full of charm! This well-cared-for, one owner 3-bedroom, 2-bath home sits in a quiet cul-de-sac and offers comfort and convenience throughout. The kitchen is bright and cheery and comes fully equipped with appliances, plus the washer and dryer are included. Enjoy a spacious basement family room—perfect for entertaining or relaxing—and step out onto the deck overlooking a large,

Sarah Cowman Homefront Real Estate, LLC

1509 W South St, Winterset, IA 50273
/34
$485,000 Sold Nov 26, 2025

2340 Holliwell Bridge Rd, Winterset, IA 50273
- Land
- 60 Acres
- $8,083 per Acre
Last Sold Summary
- 2% Below List Price
- 22 Days On Market
Last Listing Agent Chris Wearmouth Kiloterra

2340 Holliwell Bridge Rd, Winterset, IA 50273

/20
Est $229,639 Not Listed For Sale

506 E Filmore St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 1,252 Sq Ft
- Built 1921
506 E Filmore St, Winterset, IA 50273

Last Sold Summary
- 9% Above List Price
- $168/SF
- 118 Days On Market
Last Sold Price $210,000

Last Listing Agent Richard Hudnut RE/MAX

/35
$825,000 Pending
- Land
- 5.67 Acres
- $145,503 per Acre
112 S 16th Ave, Winterset, IA 50273

Don’t miss this one-of-a-kind opportunity to own a private 5+acreage right in town. A picturesque, tree-lined driveway welcomes you to a custom-built totally renovated two-story home surrounded by park-like scenery. With nearly 4,000 sq. ft. of finished living space, this 4-bedroom (plus 2 non conforming) 4-bathroom home offers room to spread out and entertain in style. The upper level features a

Sarah Cowman Homefront Real Estate, LLC

112 S 16th Ave, Winterset, IA 50273
/9
$213,000 Sold Nov 17, 2025

413 E Madison St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
- Built 2025
Last Sold Summary
- 1% Below List Price
- $207/SF
- 183 Days On Market
Last Listing Agent Alyssa Tadlock Madison County Realty

413 E Madison St, Winterset, IA 50273

/18
Est $222,368 Not Listed For Sale

510 E Filmore St, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 1,248 Sq Ft
- Built 1910
510 E Filmore St, Winterset, IA 50273

Last Sold Summary
- 7% Above List Price
- $167/SF
- 15 Days On Market
Last Sold Price $208,000

Last Listing Agent Dan Vierling Iowa Realty Mills Crossing

/21
$177,000 Pending
- 3 Beds
- 1 Bath
- 1,222 Sq Ft
601 E Green St, Winterset, IA 50273

This beautifully updated 3-bedroom, 1-bath farmhouse at 601 E Green St offers 1,222 sq ft of thoughtfully designed living space. Full of character, the home features an eat-in kitchen, a cozy living room with plenty of natural light, and a bonus room that can easily serve as an office or an extra bedroom. The updated bathroom and fresh flooring throughout the main level add modern convenience.

Theodore Craig Developers Realty Group LLC

601 E Green St, Winterset, IA 50273
/35
$580,000 Sold Aug 20, 2025

926 S 9th Ave, Winterset, IA 50273
- 4 Beds
- 3 Baths
- 1,987 Sq Ft
- Built 2019
Last Sold Summary
- 3% Below List Price
- $292/SF
- 65 Days On Market
Current Estimated Value $605,580

Last Listing Agent Jennifer Stover Madison County Realty

926 S 9th Ave, Winterset, IA 50273

/29
Est $266,678 Not Listed For Sale

311 E Filmore St, Winterset, IA 50273
- 4 Beds
- 2 Baths
- 946 Sq Ft
- Built 1997
311 E Filmore St, Winterset, IA 50273

Last Sold Summary
- 6% Above List Price
- $266/SF
- 228 Days On Market
Last Sold Price $252,000

Last Listing Agent Ian Sparks Homefront Real Estate, LLC

/4
$74,500
- Land
- 3 Acres
- $24,833 per Acre
1796 Millstream Ct, Winterset, IA 50273

Beautiful 3-acre lot located in the desirable Covered Bridge Estates! This scenic property offers the perfect blend of country feel with community convenience. Ideal for building your dream home with room to spread out—bring your own builder! Enjoy paved roads, rural water access at the road, and peaceful surroundings in this established neighborhood. Just minutes from town, with easy access to

Rachel Eller Summerset Realty

1796 Millstream Ct, Winterset, IA 50273
/16
$199,900 Sold Nov 17, 2025

520 W Madison St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 1,030 Sq Ft
- Built 2022
Last Sold Summary
- 7% Below List Price
- $194/SF
- 59 Days On Market
Last Listing Agent Nicholas Scar Iowa Realty Mills Crossing

520 W Madison St, Winterset, IA 50273

/20
Est $188,549 Not Listed For Sale

306 E Buchanan St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 986 Sq Ft
- Built 1880
306 E Buchanan St, Winterset, IA 50273

Last Sold Summary
- 11% Above List Price
- $172/SF
- 3 Days On Market
Last Sold Price $170,000

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

/17
$165,000
- 2 Beds
- 1 Bath
- 1,286 Sq Ft
415 E Buchanan St, Winterset, IA 50273

Affordable, fully updated and ready-to-move-in ranch in the heart of Winterset! Offering 1,286 sq ft, this home features a well-designed main-level layout with comfortable living space and a first-floor bedroom. Enjoy the added charm of a 3-season room perfect for relaxing or entertaining. Equipped with natural gas heating, city water and sewer, and included kitchen appliances for added

Anagha Berodia Iowa Realty Waukee

415 E Buchanan St, Winterset, IA 50273
/29
$352,500 Sold Feb 02, 2026

309 N 15th Ave, Winterset, IA 50273
- 5 Beds
- 4 Baths
- 2,110 Sq Ft
- Built 2002
Last Sold Summary
- 2% Below List Price
- $167/SF
- 76 Days On Market
Current Estimated Value $360,690

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

309 N 15th Ave, Winterset, IA 50273

/15
Est $218,657 Not Listed For Sale

423 E Benton St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
- Built 1973
423 E Benton St, Winterset, IA 50273

Last Sold Summary
- 2% Above List Price
- $213/SF
- 4 Days On Market
Last Sold Price $215,000

Last Listing Agent Robert Duff Covered Bridge Realty

/28
$455,000
- 4 Beds
- 3 Baths
- 1,555 Sq Ft
802 N 10th Ave, Winterset, IA 50273

Easy living in this open floor plan ranch home. A large covered front porch greets you as you enter the foyer. There is a nice drop zone for coats and shoes. The living room is very spacious and has a stunning gas fireplace. The kitchen is bright and features a breakfast bar and nice sized pantry. The dining is off the kitchen. The primary bedroom is large and has a huge bathroom with tile

Sarah Cowman Homefront Real Estate, LLC

802 N 10th Ave, Winterset, IA 50273
/31
$187,500 Sold Mar 19, 2026

501 W Hutchings St, Winterset, IA 50273
- 3 Beds
- 1.5 Baths
- 988 Sq Ft
- Built 1963
Last Sold Summary
- 13% Below List Price
- $190/SF
- 100 Days On Market
Current Estimated Value $199,205

Last Listing Agent Krymsin Graf Iowa Realty Ankeny

501 W Hutchings St, Winterset, IA 50273

/19
Est $182,019 Not Listed For Sale

715 N 5th St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
- Built 1999
715 N 5th St, Winterset, IA 50273

Last Sold Summary
- 23% Above List Price
- $102/SF
- 10 Days On Market
Last Sold Price $148,000

Last Listing Agent Robert Duff Covered Bridge Realty

/30
$490,000
- 4 Beds
- 3 Baths
- 1,540 Sq Ft
400 N 14th Ave, Winterset, IA 50273

This immaculate 4-bedroom, 2-bath ranch home perfectly blends modern comfort with timeless style. Built in 2013 and exceptionally cared for, every detail radiates warmth, quality, and convenience. Step inside to an inviting open layout highlighted floor-to-ceiling stone fireplace—a stunning centerpiece for cozy evenings or lively gatherings with family and friends. The beautiful kitchen is both

Sarah Cowman Homefront Real Estate, LLC

400 N 14th Ave, Winterset, IA 50273

Showing Results 121 - 160, Page 4 of 18

Iowa Madison County Saint Charles

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Saint Charles, IA Homes

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