Winterset, IA Homes

/17
Est $299,488 Not Listed For Sale

802 N 4th Ave, Winterset, IA 50273
- 4 Beds
- 2 Baths
- 1,008 Sq Ft
- Built 1960
802 N 4th Ave, Winterset, IA 50273

Last Sold Summary
- 4% Above List Price
- $285/SF
- 71 Days On Market
Last Sold Price $287,000

Last Listing Agent Lissa Baker RE/MAX

/31
$264,990 Pending
- 4 Beds
- 2 Baths
- 1,323 Sq Ft
901 E Buchanan St, Winterset, IA 50273

Completely remodeled from top to bottom, this move-in ready home blends modern finishes with functional design. The bright, updated kitchen features sleek white cabinetry, solid surface countertops, and stainless appliances, complemented by a spacious walk-in pantry with abundant prep and storage space. Bathrooms, laundry, and the entire upper level have all been thoughtfully renovated. Situated

Kenneth Kauzlarich RE/MAX Precision

901 E Buchanan St, Winterset, IA 50273
/35
$300,000 Sold Nov 03, 2025

2385 Holliwell Bridge Rd, Winterset, IA 50273
- Land
- 3.17 Acres
- $94,637 per Acre
Last Sold Summary
- 6% Below List Price
- 73 Days On Market
Current Estimated Value $278,287

Last Listing Agent Misty Darling BH&G Real Estate Innovations

2385 Holliwell Bridge Rd, Winterset, IA 50273

/12
Est $226,924 Not Listed For Sale

1002 N 4th Ave, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,169 Sq Ft
- Built 1974
1002 N 4th Ave, Winterset, IA 50273

Last Sold Summary
- 19% Above List Price
- $163/SF
- 8 Days On Market
Last Sold Price $190,000

Last Listing Agent Jennifer Stover Madison County Realty

/29
$270,000
- Land
- 10.23 Acres
- $26,393 per Acre
2212 Deer Run Ave, Winterset, IA 50273

Have you been looking for the perfect country spot to build your dream home? This 10 acre lot has all of the infrastructure already in place. It is build-ready! $50,000 has been invested in the property for a building pad, water and electric brought from the road to the build site, new driveway, etc. A future barndominium or walkout home will enjoy rolling countryside views for miles.

Jeffrey Longman RE/MAX Precision

2212 Deer Run Ave, Winterset, IA 50273
/29
$174,900 Sold Jun 03, 2025

501 W Summit St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 784 Sq Ft
- Built 1900
Last Sold Summary
- 3% Below List Price
- $223/SF
- 18 Days On Market
Current Estimated Value $176,649

Last Listing Agent Rachel Eller Summerset Realty

501 W Summit St, Winterset, IA 50273

/34
Est $280,755 Not Listed For Sale

201 S 14th Ave, Winterset, IA 50273
- 5 Beds
- 2.5 Baths
- 1,372 Sq Ft
- Built 1978
201 S 14th Ave, Winterset, IA 50273

Last Sold Summary
- 15% Above List Price
- $179/SF
- 28 Days On Market
Last Sold Price $245,000

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

/35
$650,000
- Land
- 4.6 Acres
- $141,304 per Acre
2223 Holliwell Valley Ct, Winterset, IA 50273

This exceptional walkout ranch presents an extraordinary opportunity for those seeking space, comfort, and country charm. Situated on over four and a half acres of stunning Iowa countryside, the home boasts more than three thousand square feet of beautifully finished living space with four bedrooms and four bathrooms. The open floorplan and wall of windows make the main level light, bright and

Melissa Hatchitt Zealty Home Advisors

2223 Holliwell Valley Ct, Winterset, IA 50273
/35
$725,000 Sold Oct 15, 2025

1813 Maple Ct, Winterset, IA 50273
- Land
- 6.26 Acres
- $115,815 per Acre
Last Sold Summary
- 3% Below List Price
- 22 Days On Market
Current Estimated Value $725,560

Last Listing Agent Amy Lucht Century 21 Signature

1813 Maple Ct, Winterset, IA 50273

/29
Est $469,088 Not Listed For Sale

1515 W Washington St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 2,484 Sq Ft
- Built 1978
1515 W Washington St, Winterset, IA 50273

Last Sold Summary
- 13% Above List Price
- $167/SF
- 23 Days On Market
Last Sold Price $415,000

Last Listing Agent Andrew Algreen Keller Williams Realty GDM

/35
$560,000
- Land
- 4.29 Acres
- $130,536 per Acre
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
/28
$260,000 Sold Jun 05, 2025

421 W Buchanan St, Winterset, IA 50273
- 4 Beds
- 3 Baths
- 1,500 Sq Ft
- Built 1964
Last Sold Summary
- $173/SF
- 19 Days On Market
Current Estimated Value $270,260

Last Listing Agent Stephanie Anania RE/MAX Revolution

421 W Buchanan St, Winterset, IA 50273

/32
Est $471,625 Not Listed For Sale

924 Husky Dr, Winterset, IA 50273
- 5 Beds
- 3 Baths
- 2,051 Sq Ft
- Built 2004
924 Husky Dr, Winterset, IA 50273

Last Sold Summary
- 14% Above List Price
- $203/SF
- 537 Days On Market
Last Sold Price $415,500

Last Listing Agent Betsy Breeding Realty ONE Group Impact

/34
$1,225,000
- 5 Beds
- 5 Baths
- 2,434 Sq Ft
2188 114th Ct, Winterset, IA 50072

Welcome to modern acreage living at its finest! Set on 5.32 picturesque acres in gorgeous Madison County and located in the highly desirable Adel school district, this stunning home offers the perfect blend of peaceful country living with everyday convenience. Just 13 minutes from Grand Prairie Parkway, you’ll enjoy an easy drive on all blacktop roads—no gravel! Inside, discover 4,593 sq ft of

Julie Baudler RE/MAX Concepts

2188 114th Ct, Winterset, IA 50072
/34
$185,000 Sold May 09, 2025

304 E Washington St, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 1,005 Sq Ft
- Built 1880
Last Sold Summary
- 23% Below List Price
- $184/SF
- 209 Days On Market
Current Estimated Value $188,618

Last Listing Agent Toni Tindle Covered Bridge Realty

304 E Washington St, Winterset, IA 50273

/26
Est $292,412 Not Listed For Sale

803 S 3rd St, Winterset, IA 50273
- 4 Beds
- 2 Baths
- 960 Sq Ft
- Built 1961
803 S 3rd St, Winterset, IA 50273

Last Sold Summary
- 6% Above List Price
- $286/SF
- 212 Days On Market
Last Sold Price $274,900

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

/35
$455,000
- Land
- 3 Acres
- $151,667 per Acre
2075 Hogback Bridge Rd, Winterset, IA 50273

Acreages this close to the town of Winterset are extremely hard to find, but finding one engineered to this standard is nearly impossible. This expansive 2,568 sq. ft. homestead on 3 pristine acres features 3 bedrooms, 3 bathrooms, and a large kitchen designed with plenty of storage and a sprawling floor plan for the active country lifestyle. The home features spray foam insulation throughout the

Ian Sparks Homefront Real Estate, LLC

2075 Hogback Bridge Rd, Winterset, IA 50273
/24
$218,000 Sold May 22, 2025

1104 W South St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 912 Sq Ft
- Built 1961
Last Sold Summary
- 7% Below List Price
- $239/SF
- 58 Days On Market
Current Estimated Value $221,689

Last Listing Agent Kenneth Kauzlarich RE/MAX Precision

1104 W South St, Winterset, IA 50273

/19
Est $286,055 Not Listed For Sale

1018 N 3rd Ave, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 1,426 Sq Ft
- Built 2007
1018 N 3rd Ave, Winterset, IA 50273

Last Sold Summary
- 12% Above List Price
- $179/SF
- 24 Days On Market
Last Sold Price $255,000

Last Listing Agent Rusty Dickinson Realty ONE Group Impact

/2
$70,500
- Land
- 3.45 Acres
- $20,435 per Acre
36 St, Winterset, IA 50273

3.45 Acres – Bring Your Own Builder!LAKE LOT available in Covered Bridge Estates, a welcoming community with paved roads. Enjoy the feel of peaceful country living while still having quick, convenient access to the Des Moines metro. All information obtained from seller and public records.

Rachel Eller Summerset Realty

36 St, Winterset, IA 50273
/21
$515,000 Sold Jun 18, 2025

902 S 9th Ave, Winterset, IA 50273
- 4 Beds
- 3 Baths
- 1,590 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $324/SF
- 19 Days On Market
Current Estimated Value $525,662

Last Listing Agent Jennifer Stover Madison County Realty

902 S 9th Ave, Winterset, IA 50273

/21
Est $273,238 Not Listed For Sale

926 N 3rd Ave, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 1,404 Sq Ft
- Built 2005
926 N 3rd Ave, Winterset, IA 50273

Last Sold Summary
- 11% Above List Price
- $176/SF
- 5 Days On Market
Last Sold Price $247,000

Last Listing Agent Jennifer Stover Madison County Realty

/27
$225,000
- 3 Beds
- 2 Baths
- 1,095 Sq Ft
619 N 10th St, Winterset, IA 50273

Adorable and thoughtfully updated 1 1/2 story home in historic Winterset, featuring a 2006 lift with a full poured-concrete basement. The main level offers a bright eat-in kitchen with all appliances included, whih opens to a deck - perfect for grilling. Off the kitchen is a full bathroom with laundry! There is a main floor bedroom that could also be used as a living room or flex space. Upstairs

Sarah Cowman Homefront Real Estate, LLC

619 N 10th St, Winterset, IA 50273
/6
$125,000 Sold Nov 21, 2025

Lot 5 114th Ct, Winterset, IA 50273
- Land
- 2.9 Acres
- $43,103 per Acre
Last Sold Summary
- 17% Below List Price
- 363 Days On Market
Last Listing Agent Julie Baudler RE/MAX Concepts

Lot 5 114th Ct, Winterset, IA 50273

/34
Est $525,764 Not Listed For Sale

1145 W Summit St, Winterset, IA 50273
- 4 Beds
- 4.5 Baths
- Built 1867
1145 W Summit St, Winterset, IA 50273

Last Sold Summary
- $207/SF
- 237 Days On Market
Last Sold Price $525,000

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

/7
$160,000
- Land
- 3.32 Acres
- $48,193 per Acre
2211 Cedar Bridge Rd, 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

2211 Cedar Bridge Rd, Winterset, IA 50273
/35
$365,000 Sold Jul 28, 2025

2981 214th Trail, Winterset, IA 50273
- Land
- 3.7 Acres
- $98,649 per Acre
Last Sold Summary
- 3% Below List Price
- 109 Days On Market
Current Estimated Value $377,590

Last Listing Agent Connie Brown Iowa Realty Ankeny

2981 214th Trail, Winterset, IA 50273

/33
Est $325,553 Not Listed For Sale

1169 W Summit St, Winterset, IA 50273
- 4 Beds
- 1.5 Baths
- 2,102 Sq Ft
- Built 1915
1169 W Summit St, Winterset, IA 50273

Last Sold Summary
- 14% Above List Price
- $136/SF
- 7 Days On Market
Last Sold Price $285,000

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

/21
$2
- Land
- 230.9 Acres
- $0 per Acre
2107 265th St, Winterset, IA 50273

The currently tilled farmland consists of low-80s to low-90s CSR2 soils. This highly productive ground has the ability to perform year after year. This is a farm that not only produces, but has the soil quality to sustain long-term appreciation and value. For the lifestyle and recreational buyer, the eastern tract is truly special. It offers an outstanding hunting setup with excellent access,

Jason Smith DreamDirt Farm & Ranch Real Estate

2107 265th St, Winterset, IA 50273
/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 $201,800

Last Listing Agent Sue Monroe Spire Real Estate

417 S 2nd St, Winterset, IA 50273

/17
Est $276,249 Not Listed For Sale

818 W Jefferson St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,785 Sq Ft
- Built 1950
818 W Jefferson St, Winterset, IA 50273

Last Sold Summary
- 28% Above List Price
- $120/SF
- 85 Days On Market
Last Sold Price $215,000

Last Listing Agent Jennifer Stover Madison County Realty

/13
$220,000
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
411 W Madison St, Winterset, IA 50273

Looking to downsize? Just starting out? This is home! 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

Alyssa Tadlock Madison County Realty

411 W Madison St, Winterset, IA 50273
/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 $314,487

Last Listing Agent Amanda Poganski Boutique Real Estate

103 W Lane St, Winterset, IA 50273

/35
Est $407,927 Not Listed For Sale

924 W Jefferson St, Winterset, IA 50273
- 3 Beds
- 3.5 Baths
- 1,664 Sq Ft
- Built 1956
924 W Jefferson St, Winterset, IA 50273

Last Sold Summary
- 8% Above List Price
- $226/SF
- 2 Days On Market
Last Sold Price $376,000

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

/35
$899,900
- Land
- 19.5 Acres
- $46,149 per Acre
2230 260th St, Winterset, IA 50273

Set on 19.5 acres just outside Winterset, this property offers a rare combination of scale, function and lifestyle. With nearly 4,800 finished square feet, geothermal heating and cooling, a 36x54 outbuilding and approximately 13 acres of productive row crop, this is a well-rounded acreage package that is difficult to replicate.The 1.5-story home features a warm, timeless interior with vaulted

Julie Egli RE/MAX Precision

2230 260th 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 $145,762

Last Listing Agent Randall Henry Madison County Realty

2331 Clark Tower Rd, Winterset, IA 50273

/35
Est $247,391 Not Listed For Sale

901 W Jefferson St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,064 Sq Ft
- Built 1958
901 W Jefferson St, Winterset, IA 50273

Last Sold Summary
- 1% Above List Price
- $231/SF
- 11 Days On Market
Last Sold Price $245,500

Last Listing Agent Jon Niemeyer EXIT Realty & Associates

/7
$170,000
- Land
- 3.76 Acres
- $45,213 per Acre
Lot 27 114th Ct, Winterset, IA 50273

Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a

Julie Baudler RE/MAX Concepts

Lot 27 114th Ct, 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
Current Estimated Value $107,839

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

315 N 4th Ave, Winterset, IA 50273

/25
Est $512,855 Not Listed For Sale

614 W Benton St, Winterset, IA 50273
- 3 Beds
- 2.5 Baths
- 2,595 Sq Ft
- Built 2001
614 W Benton St, Winterset, IA 50273

Last Sold Summary
- 14% Above List Price
- $173/SF
- 11 Days On Market
Last Sold Price $450,000

Last Listing Agent Jennifer Stover Madison County Realty

Showing Results 81 - 120, Page 3 of 18

Iowa Madison County Winterset

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Winterset, IA Homes

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