Winterset, IA Homes

/26
Est $259,385

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
- 211 Days On Market

/34
$1
- 3 Beds
- 1.5 Baths
- 1,344 Sq Ft
00 235th St, Winterset, IA 50273

Madison County, Iowa Land Auction! Presenting the sale of 75.33 surveyed acres m/l of premium recreational land located just southwest of Winterset, Iowa, in Madison County. This unique offering presents an excellent opportunity to purchase quality recreational property, attractive building sites, and a rural acreage in one of Iowa's most desirable counties. The property will be offered in three

Daran Becker Peoples Company

00 235th St, Winterset, IA 50273
/32
$330,000

Sold May 22, 2026

2817 Carver Rd, Winterset, IA 50273
- 3 Beds
- 2.5 Baths
- 1,600 Sq Ft
- Built 1993
Last Sold Summary
- 13% Below List Price
- $206/SF
- 56 Days On Market
Current Estimated Value $362,719

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

2817 Carver Rd, Winterset, IA 50273

/25
Est $204,782

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
- 17 Days On Market

/33
$210,000
- 2 Beds
- 2 Baths
- 1,065 Sq Ft
209 W Jefferson St Unit 17, Winterset, IA 50273

Experience elevated small-town living in this beautifully updated 3rd floor corner condo located just one block from the historic downtown square of Winterset. Unit 17 offers the rare combination of modern finishes, secure low-maintenance living, and walkable convenience with restaurants, shopping, banking, and the post office all nearby. This spacious 2 bedroom, 2 full bath condo features 1,065

Kent Brant Exit Country Realty

209 W Jefferson St Unit 17, 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 $609,774

Last Listing Agent Jennifer Stover Madison County Realty

926 S 9th Ave, Winterset, IA 50273

/16
Est $235,763

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
- 278 Days On Market

/12
$210,000

$10K PRICE DROP Pending
- 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
/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

/17
Est $151,060

Not Listed For Sale

622 N 7th St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 772 Sq Ft
- Built 1910
622 N 7th St, Winterset, IA 50273

Last Sold Summary
- 3 Days On Market

/35
$210,000
- 2 Beds
- 2 Baths
- 1,080 Sq Ft
209 W Jefferson St Unit 23, Winterset, IA 50273

Experience elevated small-town living in this beautifully updated 3rd floor corner condo located just one block from the historic downtown square of Winterset. Unit 17 offers the rare combination of modern finishes, secure low-maintenance living, and walkable convenience with restaurants, shopping, banking, and the post office all nearby. This spacious 2 bedroom, 2 full bath condo features 1,065

Kent Brant Exit Country Realty

209 W Jefferson St Unit 23, 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 $364,858

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

309 N 15th Ave, Winterset, IA 50273

/25
Est $177,717

Not Listed For Sale

707 E Buchanan St, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 1,061 Sq Ft
- Built 1910
707 E Buchanan St, Winterset, IA 50273

Last Sold Summary
- 13 Days On Market

/12
$89,900
- 3 Beds
- 2 Baths
1624 W Summit St Unit 135, Winterset, IA 50273

Welcome to this well-maintained newer 3-bedroom, 2-bathroom home offering modern comfort and style! The primary bedroom features a private en suite bathroom, creating the perfect retreat at the end of the day. Enjoy low-maintenance LVP flooring throughout the kitchen, living room, and bathrooms, with cozy carpet in all bedrooms for added comfort. The open living space provides a great layout for

Angie Standlee Covered Bridges MHP

1624 W Summit St Unit 135, Winterset, IA 50273
/26
$205,000

Sold Jun 29, 2026

406 N 7th St, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 1,042 Sq Ft
- Built 1910
Last Sold Summary
- 5% Below List Price
- $197/SF
- 9 Days On Market
Current Estimated Value $213,776

Last Listing Agent Dakoda Overbeck Iowa Realty Waukee

406 N 7th St, Winterset, IA 50273

/16
Est $247,575

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
- 13 Days On Market

/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
/2
$658,000

Sold Jun 15, 2026

1525 S 4th Ave Unit 2, Winterset, IA 50273
- 5 Beds
- 3.5 Baths
- 2,582 Sq Ft
- Built 1997
Last Sold Summary
- $255/SF
- 103 Days On Market
Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

1525 S 4th Ave Unit 2, Winterset, IA 50273

/20
Est $210,172

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
- 118 Days On Market

/24
$257,500

$5K PRICE DROP Pending
- 4 Beds
- 2 Baths
- 1,482 Sq Ft
610 W Washington St, Winterset, IA 50273

Charming Cape Cod with space, style, and a location you’ll love. This well-maintained 1.5-story home offers 1,482 square feet of inviting living space, featuring 4 bedrooms and 2 bathrooms designed for comfort and flexibility. Step inside to find a home that has been exceptionally cared for—clean, bright, and move-in ready. The layout offers a cozy yet functional flow, with a finished lower level

Larry Corkrean Madison County Realty

610 W Washington St, 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 $194,879

Last Listing Agent Krymsin Graf Iowa Realty Ankeny

501 W Hutchings St, Winterset, IA 50273

/18
Est $211,092

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
- 15 Days On Market

/34
$350,000

$25K PRICE DROP
- 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
/27
$204,000

Sold Nov 20, 2025

202 S 7th Ave, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 1,050 Sq Ft
- Built 1953
Last Sold Summary
- 3% Below List Price
- $194/SF
- 48 Days On Market
Current Estimated Value $194,006

Last Listing Agent Tiffany Ehler Boutique Real Estate

202 S 7th Ave, Winterset, IA 50273

/29
Est $257,987

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
- 228 Days On Market

/23
$290,000

$30K PRICE DROP
- 3 Beds
- 2 Baths
- 1,204 Sq Ft
212 N 14th Ave, Winterset, IA 50273

Sweet ranch home located on a quiet street. The open concept floor plan makes this house feel bigger than it is. The 1st floor offers 2 large bedrooms, 1 full bath, kitchen with a breakfast bar and a private home office space. The lower level features a huge family room, large bedroom and full bath - and still plenty of storage space. Sliding door off the dining area leads to the private

Jennifer Stover Madison County Realty

212 N 14th Ave, Winterset, IA 50273
/23
$128,000

Sold Dec 30, 2025

516 W Summit St, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
- Built 1890
Last Sold Summary
- 25% Below List Price
- $107/SF
- 95 Days On Market
Last Listing Agent Betsy Breeding Realty ONE Group Impact

516 W Summit St, Winterset, IA 50273

/15
Est $211,778

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
- 4 Days On Market

/18
$175,000

$24K PRICE DROP
- Land
- 7.14 Acres
- $24,510 per Acre
2368 Saint Charles Rd, Winterset, IA 50273

BRING YOUR OWN BUILDER!!! This 7.14 acres is located right off the St Charles pavement, offering convenience and gorgeous fall views. Schedule a showing today!

Rachel Eller Summerset Realty

2368 Saint Charles Rd, Winterset, IA 50273
/31
$477,500

Sold Aug 01, 2025

519 W Mills St, Winterset, IA 50273
- 4 Beds
- 3 Baths
- 1,597 Sq Ft
- Built 2023
Last Sold Summary
- 2% Below List Price
- $299/SF
- 23 Days On Market
Current Estimated Value $486,315

Last Listing Agent Renee Dunkel Century 21 Signature

519 W Mills St, Winterset, IA 50273

/19
Est $206,189

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
- 10 Days On Market

/32
$270,000
- 4 Beds
- 2 Baths
- 866 Sq Ft
715 N 3rd Ave, Winterset, IA 50273

** MOVE IN READY WITH ALL THE UPDATES ** This 4 bed 2 bath has been thoughtfully and skillfully updated and is ready for its new owners! Improvements include: All new interior paint. New/updated trim. All new Flooring. New lighting. New windows in 2025. Interior doors summer 2025. New siding approx 15 years ago with new paint summer 2025. New roof/sofit/facia approx 10 years. Furnace 3 years.

Alyssa Tadlock Madison County Realty

715 N 3rd Ave, Winterset, IA 50273
/32
$315,000

Sold Jan 27, 2026

1541 Nature Ct, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
- Built 2001
Last Sold Summary
- 3% Below List Price
- $216/SF
- 47 Days On Market
Current Estimated Value $325,199

Last Listing Agent Elizabeth Gordon Realty ONE Group Impact

1541 Nature Ct, Winterset, IA 50273

/25
Est $224,431

Not Listed For Sale

508 E Lane St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,092 Sq Ft
- Built 1998
508 E Lane St, Winterset, IA 50273

Last Sold Summary
- 60 Days On Market

/7
$140,000
- Land
- 5.36 Acres
- $26,119 per Acre
002 220th St, Winterset, IA 50273

Build your dream home on 5.36 acres in scenic Madison County. Located just 20 minutes from West Des Moines and 2 miles south of Hwy 92, this beautiful building site offers rural water, electricity, and high-speed fiber internet at the road. Enjoy peaceful country living on a well-maintained gravel road with an easy commute to DSM

Jodi Broadbent Realty ONE Group Impact

002 220th St, Winterset, IA 50273
/7
$199,000

Sold Oct 28, 2025

Lot 21 112th Ct, Winterset, IA 50273
- Land
- 3.37 Acres
- $59,050 per Acre
Last Sold Summary
- 20% Below List Price
- 326 Days On Market
Last Listing Agent Julie Baudler RE/MAX Concepts

Lot 21 112th Ct, Winterset, IA 50273

/26
Est $229,396

Not Listed For Sale

622 W Fremont St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
- Built 1954
622 W Fremont St, Winterset, IA 50273

Last Sold Summary
- 167 Days On Market

/2
$382,500

Pending
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
309 Maple Pointe, Winterset, IA 50273

Stryker Ranch New Construction with oversized 3 car garage. Front porch with 2 stone base posts. 9' ceilings throughout main floor. Open stairs to basement. Granite or quartz countertops in baths and kitchen. Kitchen boasts of a large walk-in pantry and stainless-steel appliances. White cabinets throughout. Luxury vinyl flooring. Gas fireplace. Master bath with raised vanity and elongated stool.

Robert D. Weeks Iowa Realty Waukee

309 Maple Pointe, Winterset, IA 50273
/3
$220,000

Sold Sep 15, 2025

825 W Fremont St, Winterset, IA 50273
- 2 Beds
- 2.5 Baths
- 1,213 Sq Ft
- Built 2000
Last Sold Summary
- 2% Below List Price
- $181/SF
- 3 Days On Market
Current Estimated Value $212,829

Last Listing Agent Randall Henry Madison County Realty

825 W Fremont St, Winterset, IA 50273

/29
Est $171,123

Not Listed For Sale

501 W Summit St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 784 Sq Ft
- Built 1900
501 W Summit St, Winterset, IA 50273

Last Sold Summary
- 18 Days On Market

Showing Results 161 - 200, Page 5 of 18

Iowa Madison County Winterset

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Winterset, IA Homes

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