Recently Sold Winterset, IA Homes

/25
$205,500 Sold Oct 28, 2025

417 S 2nd St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,524 Sq Ft
- Built 1921
Last Sold Summary
- 4% Below List Price
- $135/SF
- 91 Days On Market
Current Estimated Value $203,795

Last Listing Agent Sue Monroe Spire Real Estate

417 S 2nd St, Winterset, IA 50273
Selling your home? Sell it faster and for more with a Homes.com Boost.
Learn More
/19
$298,000 Sold Aug 29, 2025

103 W Lane St, Winterset, IA 50273
- 4 Beds
- 2.5 Baths
- 2,696 Sq Ft
- Built 1908
Last Sold Summary
- $111/SF
- 20 Days On Market
Current Estimated Value $310,757

Last Listing Agent Amanda Poganski Boutique Real Estate

103 W Lane St, Winterset, IA 50273
/2
$209,500 Sold Feb 07, 2025

111 S 3rd St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1957
Last Sold Summary
- 3% Below List Price
- $198/SF
- 47 Days On Market
Current Estimated Value $198,861

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

111 S 3rd St, Winterset, IA 50273
/12
$140,000 Sold Jul 29, 2025

2331 Clark Tower Rd, Winterset, IA 50273
- Land
- 5.72 Acres
- $24,476 per Acre
Last Sold Summary
- 20% Below List Price
- 278 Days On Market
Current Estimated Value $139,174

Last Listing Agent Randall Henry Madison County Realty

2331 Clark Tower Rd, Winterset, IA 50273
/17
$84,000 Sold Dec 19, 2025

315 N 4th Ave, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 1,075 Sq Ft
- Built 1888
Last Sold Summary
- 20% Below List Price
- $78/SF
- 176 Days On Market
Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

315 N 4th Ave, Winterset, IA 50273
/23
$190,000 Sold May 23, 2025

323 E Jefferson St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 992 Sq Ft
- Built 1947
Last Sold Summary
- 2% Above List Price
- $192/SF
- 6 Days On Market
Current Estimated Value $190,860

Last Listing Agent Deanna Roth Century 21 Signature

323 E Jefferson St, Winterset, IA 50273
/35
$506,942 Sold Jun 26, 2025

2364 Bittersweet Ave, Winterset, IA 50273
- Land
- 5.26 Acres
- $96,377 per Acre
Last Sold Summary
- 5% Above List Price
- 2 Days On Market
Current Estimated Value $506,267

Last Listing Agent Jeffrey Longman RE/MAX Precision

2364 Bittersweet Ave, Winterset, IA 50273
/32
$485,000 Sold Nov 03, 2025

301 Magnolia Point, Winterset, IA 50273
- 6 Beds
- 3.5 Baths
- 2,351 Sq Ft
- Built 2020
Last Sold Summary
- 9% Below List Price
- $206/SF
- 146 Days On Market
Current Estimated Value $488,179

Last Listing Agent Rachel Eller Summerset Realty

301 Magnolia Point, Winterset, IA 50273
/23
$200,000 Sold Aug 01, 2025

324 W Filmore St, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 1,008 Sq Ft
- Built 1956
Last Sold Summary
- 7% Below List Price
- $198/SF
- 29 Days On Market
Current Estimated Value $199,258

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

324 W Filmore St, Winterset, IA 50273
/28
$870,000 Sold Jan 02, 2026

2176 148th St, Winterset, IA 50273
- Land
- 17.97 Acres
- $48,414 per Acre
Last Sold Summary
- 8% Below List Price
- 85 Days On Market
Last Listing Agent Jason Russell Realty ONE Group Impact

2176 148th 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 $758,670

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

4726 Cherrywood Ln, Winterset, IA 50273
/35
$250,000 Sold Mar 21, 2025

2646 Fieldstone Ave, Winterset, IA 50273
- Land
- 20 Acres
- $12,500 per Acre
Last Sold Summary
- 16 Days On Market
Current Estimated Value $260,639

Last Listing Agent Charles Johnson Kiloterra

2646 Fieldstone Ave, 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 $302,682

Last Listing Agent Ou Meksay RE/MAX Concepts

1210 W Jefferson St, 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 $298,557

Last Listing Agent Kristen Stehli RE/MAX Precision

522 N 10th St, Winterset, IA 50273
/7
$160,000 Sold Jan 08, 2026

Lot 23 112th Ct, Winterset, IA 50273
- Land
- 3.34 Acres
- $47,904 per Acre
Last Sold Summary
- 20% Below List Price
- 413 Days On Market
Last Listing Agent Julie Baudler RE/MAX Concepts

Lot 23 112th Ct, Winterset, IA 50273
/35
$569,900 Sold Sep 24, 2025

1713 Merriam Ct, Winterset, IA 50273
- Land
- 3.01 Acres
- $189,336 per Acre
Last Sold Summary
- 3 Days On Market
Current Estimated Value $565,731

Last Listing Agent Connie Ridgway Iowa Realty Mills Crossing

1713 Merriam Ct, Winterset, IA 50273
/5
$369,555 Sold Mar 27, 2025

301 Maple Point, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 2024
Last Sold Summary
- 2% Above List Price
- $264/SF
- 99 Days On Market
Last Listing Agent Robert D. Weeks Iowa Realty Waukee

301 Maple Point, 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 $311,785

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

522 N 7th Ave, 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 $234,480

Last Listing Agent Keith Soldwisch Zealty Home Advisors

2430 Highway 169, 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
Last Listing Agent Dustin Crawford Iowa Home & Land Realty

315 S 5th Ave, 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
/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
/7
$159,200 Sold Sep 26, 2025

Lot 8 114th Ct, Winterset, IA 50273
- Land
- 3.02 Acres
- $52,715 per Acre
Last Sold Summary
- 20% Below List Price
- 307 Days On Market
Last Listing Agent Julie Baudler RE/MAX Concepts

Lot 8 114th Ct, Winterset, IA 50273
/2
$209,500 Sold Feb 07, 2025

111 S 3rd St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,056 Sq Ft
- Built 1957
Last Sold Summary
- 3% Below List Price
- $198/SF
- 1 Day On Market
Current Estimated Value $198,861

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

111 S 3rd 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 $589,711

Last Listing Agent Jennifer Stover Madison County Realty

926 S 9th Ave, 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
/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
Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

309 N 15th Ave, Winterset, IA 50273
/13
$24,500 Sold Mar 20, 2025

000 Roseman Bridge Rd, Winterset, IA 50273
- Land
- 5.25 Acres
- $4,667 per Acre
Last Sold Summary
- 30% Below List Price
- 161 Days On Market
Last Listing Agent Shane Spyksma Kiloterra

000 Roseman Bridge Rd, Winterset, IA 50273
/15
$313,000 Sold Mar 28, 2025

815 N 11th Avenue Cir, Winterset, IA 50273
- 3 Beds
- 3 Baths
- 1,356 Sq Ft
- Built 2021
Last Sold Summary
- 6% Below List Price
- $231/SF
- 61 Days On Market
Current Estimated Value $331,449

Last Listing Agent Brent Kelso Silverado Realty

815 N 11th Avenue Cir, 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
Last Listing Agent Tiffany Ehler Boutique Real Estate

202 S 7th Ave, Winterset, IA 50273
/29
$215,000 Sold Jun 26, 2025

315 W Washington St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 1,673 Sq Ft
- Built 1944
Last Sold Summary
- 19% Below List Price
- $129/SF
- 27 Days On Market
Current Estimated Value $232,359

Last Listing Agent Misty Darling BH&G Real Estate Innovations

315 W Washington St, 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
/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 $472,659

Last Listing Agent Renee Dunkel Century 21 Signature

519 W Mills St, 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
Last Listing Agent Elizabeth Gordon Realty ONE Group Impact

1541 Nature Ct, 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
/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 $219,525

Last Listing Agent Randall Henry Madison County Realty

825 W Fremont St, 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
/32
$160,000 Sold Jul 08, 2025

415 E Jefferson St, Winterset, IA 50273
- 4 Beds
- 1.5 Baths
- 2,018 Sq Ft
- Built 1922
Last Sold Summary
- 6% Below List Price
- $79/SF
- 41 Days On Market
Current Estimated Value $177,737

Last Listing Agent Betsy Breeding Realty ONE Group Impact

415 E Jefferson St, Winterset, IA 50273
/33
$220,000 Sold Aug 26, 2025

1755 280th St, Winterset, IA 50273
- Land
- 2.5 Acres
- $88,000 per Acre
Last Sold Summary
- 12% Below List Price
- 85 Days On Market
Current Estimated Value $175,618

Last Listing Agent Toni Tindle Covered Bridge Realty

1755 280th St, Winterset, IA 50273
/20
$125,000 Sold May 20, 2025

728 W Green St, Winterset, IA 50273
- 3 Beds
- 1.5 Baths
- 1,255 Sq Ft
- Built 1896
Last Sold Summary
- 12% Below List Price
- $100/SF
- 4 Days On Market
Current Estimated Value $139,823

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

728 W Green St, Winterset, IA 50273

Showing Results 41 - 80, Page 2 of 5

Iowa Madison County Winterset

How to Buy a Home How to Finance a Home How to Sell a Home

Winterset Types of Homes for Sale

Winterset Real Estate Listings

Newest Listings in Winterset

Winterset Homes by Price

More About Living in Winterset

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage