Winterset, IA Homes

/29
Est $178,238

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
Last Listing Agent Rachel Eller Summerset Realty

/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
/7
$125,000

Sold Nov 21, 2025

Lot 4 114th Ct, Winterset, IA 50273
- Land
- 2.95 Acres
- $42,373 per Acre
Last Sold Summary
- 17% Below List Price
- 363 Days On Market
Last Listing Agent Julie Baudler RE/MAX Concepts

Lot 4 114th Ct, Winterset, IA 50273

/12
Not Listed For Sale

602 S 2nd St, Winterset, IA 50273
- Studio
- 4 Baths
- 3,600 Sq Ft
- Built 1998
602 S 2nd St, Winterset, IA 50273

Last Sold Summary
- 51 Days On Market
Last Listing Agent Toni Tindle Covered Bridge Realty

/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
/21
$221,100

Sold Feb 20, 2026

110 E Grade St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,174 Sq Ft
- Built 1904
Last Sold Summary
- 2% Below List Price
- $188/SF
- 111 Days On Market
Current Estimated Value $200,528

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

110 E Grade St, Winterset, IA 50273

/20
Est $214,223

Not Listed For Sale

824 S 4th Ave, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 1,130 Sq Ft
- Built 1937
824 S 4th Ave, Winterset, IA 50273

Last Sold Summary
- 41 Days On Market
Last Listing Agent Brady Jackson Iowa Realty South

/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
/33
$217,000

Sold Apr 13, 2026

705 S 2nd St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 2,085 Sq Ft
- Built 2003
Last Sold Summary
- 4% Below List Price
- $104/SF
- 46 Days On Market
Current Estimated Value $240,338

Last Listing Agent Kyle Kuhns RE/MAX Revolution

705 S 2nd St, Winterset, IA 50273

/32
Est $234,365

Not Listed For Sale

814 S 4th Ave, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
- Built 1974
814 S 4th Ave, Winterset, IA 50273

Last Sold Summary
- 13 Days On Market
Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

/12
$87,900

$2K PRICE DROP
- 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

Mahayla Claiser Covered Bridges MHP

1624 W Summit St Unit 135, Winterset, IA 50273
/26
$195,000

Sold Apr 24, 2026

827 W Fremont St, Winterset, IA 50273
- 2 Beds
- 3 Baths
- 1,213 Sq Ft
- Built 2001
Last Sold Summary
- 11% Below List Price
- $161/SF
- 139 Days On Market
Current Estimated Value $205,538

Last Listing Agent Toni Tindle Covered Bridge Realty

827 W Fremont St, Winterset, IA 50273

/25
Est $284,477

Not Listed For Sale

517 W Short St, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 1,520 Sq Ft
- Built 1982
517 W Short St, Winterset, IA 50273

Last Sold Summary
- 126 Days On Market
Last Listing Agent Jennifer Stover Madison County Realty

/23
$239,900
- 3 Beds
- 1.5 Baths
- 1,241 Sq Ft
816 E Washington St, Winterset, IA 50273

Charming and well located, this 3 bed, 1.5 bath home sits on a quiet street just a shortdistance from Winterset’s vibrant town square. The main floor features a living room, large dining room, andfunctional kitchen, along with a convenient main floor bedroom and half bath. Upstairs offers two additionalbedrooms and a full bathroom. Outside, enjoy a private backyard with a patio—perfect for

Laurel Pangman Keller Williams Realty GDM

816 E Washington St, Winterset, IA 50273
/31
$235,000

Sold May 22, 2026

609 E Filmore St, Winterset, IA 50273
- 4 Beds
- 2 Baths
- 1,104 Sq Ft
- Built 1979
Last Sold Summary
- 14% Below List Price
- $213/SF
- 290 Days On Market
Current Estimated Value $248,660

Last Listing Agent Toni Tindle Covered Bridge Realty

609 E Filmore St, Winterset, IA 50273

/29
Not Listed For Sale

808 S 5th Ave, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 1,232 Sq Ft
- Built 1890
808 S 5th Ave, Winterset, IA 50273

Last Sold Summary
- 95 Days On Market
Last Listing Agent Roger Queck Pro Team Realty

/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
/34
$240,000

Sold Jun 05, 2026

114 N 8th Ave, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,545 Sq Ft
- Built 1890
Last Sold Summary
- 2% Below List Price
- $155/SF
- 59 Days On Market
Current Estimated Value $239,401

Last Listing Agent Sara Hopkins RE/MAX Precision

114 N 8th Ave, Winterset, IA 50273

/26
Est $268,851

Not Listed For Sale

401 E Jefferson St, Winterset, IA 50273
- 4 Beds
- 2.5 Baths
- 2,016 Sq Ft
- Built 1900
401 E Jefferson St, Winterset, IA 50273

Last Sold Summary
- 173 Days On Market
Last Listing Agent Jennifer Stover Madison County Realty

/35
$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
/35
$440,000

Sold Apr 23, 2026

812 N 8th Ave, Winterset, IA 50273
- 5 Beds
- 3 Baths
- 2,137 Sq Ft
- Built 2002
Last Sold Summary
- 9% Below List Price
- $206/SF
- 229 Days On Market
Current Estimated Value $448,757

Last Listing Agent Matt Cole RE/MAX Concepts

812 N 8th Ave, Winterset, IA 50273

/26
Est $220,546

Not Listed For Sale

502 E Washington St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,386 Sq Ft
- Built 1895
502 E Washington St, Winterset, IA 50273

Last Sold Summary
- 4 Days On Market
Last Listing Agent Kyle Kuhns RE/MAX Revolution

/24
$290,000

$30K PRICE DROP Pending
- 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
/27
$495,000

Sold Dec 29, 2025

2155 148th St, Winterset, IA 50273
- 4 Beds
- 3 Baths
- 1,404 Sq Ft
- Built 2006
Last Sold Summary
- 23% Below List Price
- $353/SF
- 45 Days On Market
Current Estimated Value $511,883

Last Listing Agent Cindy Miller Keller Williams Realty GDM

2155 148th St, Winterset, IA 50273

/15
Est $252,899

Not Listed For Sale

418 E Buchanan St, Winterset, IA 50273
- 4 Beds
- 2.5 Baths
- 1,200 Sq Ft
- Built 1979
418 E Buchanan St, Winterset, IA 50273

Last Sold Summary
- 7 Days On Market
Last Listing Agent Nick Stephenson Realty ONE Group Impact

/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
/9
$265,410

Sold Nov 26, 2025

TBD Pioneer Ave, Winterset, IA 50273
- Land
- 29.49 Acres
- $9,000 per Acre
Last Sold Summary
- 3% Below List Price
- 22 Days On Market
Last Listing Agent Chris Wearmouth Kiloterra

TBD Pioneer Ave, Winterset, IA 50273

/17
Est $197,221

Not Listed For Sale

523 N 5th St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 968 Sq Ft
- Built 1905
523 N 5th St, Winterset, IA 50273

Last Sold Summary
- 146 Days On Market
Last Listing Agent Robert Duff Covered Bridge Realty

/32
$265,000

$5K PRICE DROP
- 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
/34
$260,000

Sold Jun 29, 2026

524 W Benton St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,705 Sq Ft
- Built 1964
Last Sold Summary
- 5% Below List Price
- $152/SF
- 24 Days On Market
Current Estimated Value $269,421

Last Listing Agent Jennifer Stover Madison County Realty

524 W Benton St, Winterset, IA 50273

/28
Est $262,896

Not Listed For Sale

719 S 7th Ave, Winterset, IA 50273
- 3 Beds
- 2.5 Baths
- 1,170 Sq Ft
- Built 1975
719 S 7th Ave, Winterset, IA 50273

Last Sold Summary
- 134 Days On Market
Last Listing Agent Rachel Eller Summerset Realty

/10
$193,000

$4K PRICE INCREASE Pending
- Land
- 5.01 Acres
- $38,523 per Acre
1700 Highway 169 None, Winterset, IA 50273

Beautiful 4.98 acres located right off the highway. Rural water & electric at the road. Lot includes barn set up for animals and a workshop. Gorgeous sunrise and sunset view; and no covenants! Bring your own builder and make this property your own paradise. The survey has been completed and the seller is working with the County now on subdivision proceedings.

Sarah Cowman Homefront Real Estate, LLC

1700 Highway 169 None, Winterset, IA 50273
/32
$176,500

Sold Aug 29, 2025

409 W Filmore St, Winterset, IA 50273
- 3 Beds
- 1.5 Baths
- 1,192 Sq Ft
- Built 1900
Last Sold Summary
- 5% Below List Price
- $148/SF
- 67 Days On Market
Current Estimated Value $182,582

Last Listing Agent Misty Darling BH&G Real Estate Innovations

409 W Filmore St, Winterset, IA 50273

/31
Est $331,040

Not Listed For Sale

602 W Hutchings St, Winterset, IA 50273
- 4 Beds
- 2.5 Baths
- 1,904 Sq Ft
- Built 1967
602 W Hutchings St, Winterset, IA 50273

Last Sold Summary
- 7 Days On Market
Last Listing Agent Susie Sheldahl Realty One Group Impact

/15
$43,900
- 3 Beds
- 2 Baths
- 1,216 Sq Ft
1624 W Summit St Unit 115, Winterset, IA 50273

Discover the perfect blend of comfort and space in this beautiful 3-bedroom, 2-bath home featuring a spacious open-concept floor plan designed for today's lifestyle. The inviting layout creates a seamless flow between the living, dining, and kitchen areas, making everyday living and entertaining effortless. Generously sized bedrooms, ample natural light, and thoughtfully designed living spaces

Mahayla Claiser Covered Bridges MHP

1624 W Summit St Unit 115, Winterset, IA 50273
/23
$162,500

Sold Jun 02, 2026

604 E Jefferson St, Winterset, IA 50273
- 3 Beds
- 1.5 Baths
- 1,306 Sq Ft
- Built 1896
Last Sold Summary
- 10% Below List Price
- $124/SF
- 60 Days On Market
Current Estimated Value $170,465

Last Listing Agent Toni Tindle Covered Bridge Realty

604 E Jefferson St, Winterset, IA 50273

/29
Est $308,469

Not Listed For Sale

621 S 8th Ave, Winterset, IA 50273
- 4 Beds
- 2.5 Baths
- 1,284 Sq Ft
- Built 1968
621 S 8th Ave, Winterset, IA 50273

Last Sold Summary
- 28 Days On Market
Last Listing Agent Danielle Burnight RE/MAX Concepts

/7
$140,000
- Land
- 5.78 Acres
- $24,221 per Acre
002 220th St, Winterset, IA 50273

Build your dream home on 5.78 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
/35
$575,000

Sold Sep 30, 2025

2283 Clark Tower Rd, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Built 2022
Last Sold Summary
- 15% Below List Price
- $319/SF
- 29 Days On Market
Current Estimated Value $581,727

Last Listing Agent Marcus Sereg Iowa Realty South

2283 Clark Tower Rd, Winterset, IA 50273

/14
Est $136,093

Not Listed For Sale

603 W Hutchings St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 664 Sq Ft
- Built 1880
603 W Hutchings St, Winterset, IA 50273

Last Sold Summary
- 147 Days On Market
Last Listing Agent Anthony Dennis RE/MAX Revolution

Showing Results 201 - 240, Page 6 of 18

Iowa Madison County

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Winterset, IA Homes

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