Winterset, IA Homes

/7
$160,000
- Land
- 3.27 Acres
- $48,930 per Acre
2323 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

2323 Cedar Bridge Rd, Winterset, IA 50273
/19
$162,250

Sold Jun 23, 2026

703 W North St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 950 Sq Ft
- Built 1947
Last Sold Summary
- 5% Below List Price
- $171/SF
- 20 Days On Market
Current Estimated Value $160,216

Last Listing Agent Tina Knox Iowa Realty Mills Crossing

703 W North St, Winterset, IA 50273

/20
Est $254,450

Not Listed For Sale

501 W Buchanan St, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
- Built 1963
501 W Buchanan St, Winterset, IA 50273

Last Sold Summary
- 34 Days On Market
Last Listing Agent Jamie Adkins RE/MAX Precision

/35
$849,900

$200K PRICE DROP Pending
- 3 Beds
- 3.5 Baths
- 3,660 Sq Ft
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
/33
$647,499

Sold Mar 27, 2026

1634 170th St, Winterset, IA 50273
- 4 Beds
- 3 Baths
- 1,895 Sq Ft
- Built 2001
Last Sold Summary
- 4% Below List Price
- $342/SF
- 268 Days On Market
Current Estimated Value $644,409

Last Listing Agent Kate Carlson Realty ONE Group Impact

1634 170th St, Winterset, IA 50273

/28
Est $282,069

Not Listed For Sale

421 W Buchanan St, Winterset, IA 50273
- 4 Beds
- 3 Baths
- 1,500 Sq Ft
- Built 1964
421 W Buchanan St, Winterset, IA 50273

Last Sold Summary
- 19 Days On Market
Last Listing Agent Stephanie Anania RE/MAX Revolution

/7
$170,000

$45K PRICE DROP
- 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
/15
$215,000

Sold Aug 14, 2026

1110 W South St, Winterset, IA 50273
- 3 Beds
- 1.5 Baths
- 1,180 Sq Ft
- Built 1961
Last Sold Summary
- $182/SF
- 0 Days On Market
Current Estimated Value $212,960

Last Listing Agent Rachel Eller Summerset Realty

1110 W South St, Winterset, IA 50273

/22
Est $222,861

Not Listed For Sale

618 N 4th Ave, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 864 Sq Ft
- Built 1970
618 N 4th Ave, Winterset, IA 50273

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

/35
$949,900
- 3 Beds
- 2.5 Baths
- 3,210 Sq Ft
1524 260th St, Winterset, IA 50273

DREAMS DO COME TRUE! Take a look at this exquisite 2 story home on 15ac in beautiful MADISON COUNTY. The CRAFTSMANSHIP of this home is amazing, from the CUSTOM CABINETS, DOORS and COMMERCIAL EXHAUST VENT, all made on site, to the CUSTOM STEEL BACKSPLASH and BARN BOARDS from the old Homestead that was located on this acreage. The LARGE GRANITE BAR has a built-in beverage frig and seating for 8.

Betsy Breeding Realty ONE Group Impact

1524 260th St, Winterset, IA 50273
/28
$870,000

Sold Jan 02, 2026

2176 148th St, Winterset, IA 50273
- 4 Beds
- 2.5 Baths
- 1,534 Sq Ft
- Built 2005
Last Sold Summary
- 8% Below List Price
- $567/SF
- 85 Days On Market
Current Estimated Value $825,730

Last Listing Agent Jason Russell Realty ONE Group Impact

2176 148th St, Winterset, IA 50273

/24
Est $228,754

Not Listed For Sale

1104 W South St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 912 Sq Ft
- Built 1961
1104 W South St, Winterset, IA 50273

Last Sold Summary
- 58 Days On Market
Last Listing Agent Kenneth Kauzlarich RE/MAX Precision

/29
$299,000
- 2 Beds
- 1.5 Baths
- 1,476 Sq Ft
519 W Filmore St, Winterset, IA 50273

Old-world charm meets modern living in this beautifully maintained and renovated two story home, situated on a corner lot with landscaped grounds. Rich original woodwork, abundant natural light, and timeless character create a warm and inviting atmosphere throughout.The fully renovated kitchen and bathroom blend classic style with modern luxury, featuring custom cabinetry, premium Café

Kurt Clements ListWithFreedom.com Inc

519 W Filmore 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 $310,312

Last Listing Agent Kristen Stehli Real Broker, LLC

522 N 10th St, Winterset, IA 50273

/25
Est $231,803

Not Listed For Sale

1016 W South St, Winterset, IA 50273
- 2 Beds
- 1 Bath
- 912 Sq Ft
- Built 1960
1016 W South St, Winterset, IA 50273

Last Sold Summary
- 4 Days On Market
Last Listing Agent Sue Monroe Spire Real Estate

/34
$280,000
- 4 Beds
- 3 Baths
- 2,146 Sq Ft
602 N 1st Ave, Winterset, IA 50273

Step into the timeless charm of this spacious Victorian home, perfectly situated on a corner lot in one of historic Winterset's established neighborhoods. With four bedrooms and multiple bathrooms, there's plenty of room for family, guests, or a growing household. The home offers both an inviting eat-in kitchen and a formal dining room, providing flexible spaces for everyday meals or holiday

Kate Carlson Realty ONE Group Impact

602 N 1st Ave, Winterset, IA 50273
/17
$174,900

Sold Jul 31, 2026

402 N 9th St, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 1,152 Sq Ft
- Built 1978
Last Sold Summary
- 3% Below List Price
- $152/SF
- 30 Days On Market
Current Estimated Value $179,065

Last Listing Agent Randall Henry Madison County Realty

402 N 9th St, Winterset, IA 50273

/31
Est $293,201

Not Listed For Sale

926 W Court Ave, Winterset, IA 50273
- 4 Beds
- 2 Baths
- 1,387 Sq Ft
- Built 1959
926 W Court Ave, Winterset, IA 50273

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

/7
$230,000
- Land
- 2.9 Acres
- $79,310 per Acre
Lot 30 Limestone 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 30 Limestone Ct, 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

/28
Est $229,815

Not Listed For Sale

902 W Court Ave, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 1,268 Sq Ft
- Built 1959
902 W Court Ave, Winterset, IA 50273

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

/7
$194,000

$5K PRICE INCREASE
- Land
- 2.88 Acres
- $67,361 per Acre
Lot 25 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 25 114th Ct, Winterset, IA 50273
/23
$295,000

Sold Jul 02, 2026

521 W Hutchings St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 838 Sq Ft
- Built 1964
Last Sold Summary
- 2% Below List Price
- $352/SF
- 74 Days On Market
Current Estimated Value $288,990

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

521 W Hutchings St, Winterset, IA 50273

/24
Est $264,346

Not Listed For Sale

906 W Court Ave, Winterset, IA 50273
- 3 Beds
- 2.5 Baths
- 1,260 Sq Ft
- Built 1959
906 W Court Ave, Winterset, IA 50273

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

/7
$225,000

$35K PRICE DROP
- Land
- 3.14 Acres
- $71,656 per Acre
Lot 14 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 14 114th Ct, 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 $215,278

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

2236 Carver Rd, Winterset, IA 50273

/35
Est $242,715

Not Listed For Sale

815 W Court Ave, Winterset, IA 50273
- 2 Beds
- 1.5 Baths
- 1,254 Sq Ft
- Built 1958
815 W Court Ave, Winterset, IA 50273

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

/30
$399,990

$199K PRICE DROP Pending
- 3 Beds
- 1 Bath
- 2,286 Sq Ft
1024 W Summit St, Winterset, IA 50273

In town acreage opportunity. 3-bedroom, 1-bath home on 9.88 m/l acres located just outside the Winterset city limits. The home offers 2,286 sq ft of living area with main-level and upper-level bedrooms, and a partial basement. A detached 1-car garage and a 1,620 sq ft pole building provides additional storage and workspace. The acreage features open ground with level to rolling terrain and treed

Jerold Steenhoek Iowa Realty Waukee

1024 W Summit St, Winterset, IA 50273
/35
$569,900

Sold Sep 24, 2025

1713 Merriam Ct, Winterset, IA 50273
- 3 Beds
- 3 Baths
- 1,493 Sq Ft
- Built 2017
Last Sold Summary
- $382/SF
- 3 Days On Market
Current Estimated Value $572,880

Last Listing Agent Connie Ridgway Iowa Realty Mills Crossing

1713 Merriam Ct, Winterset, IA 50273

/28
Est $233,415

Not Listed For Sale

705 W Benton St, Winterset, IA 50273
- 4 Beds
- 2 Baths
- 924 Sq Ft
- Built 1976
705 W Benton St, Winterset, IA 50273

Last Sold Summary
- 21 Days On Market
Last Listing Agent Ian Sparks Homefront Real Estate, LLC

/11
$210,000

$10K PRICE DROP
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
409 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

409 W Madison 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 $203,396

Last Listing Agent Dustin Crawford Iowa Home & Land Realty

315 S 5th Ave, Winterset, IA 50273

/26
Est $288,593

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
- 10 Days On Market
Last Listing Agent Sonny Greene Iowa Realty Mills Crossing

/23
$219,900

$30K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,006 Sq Ft
113 S 3rd St, Winterset, IA 50273

Move-in ready and totally remodeled 3-bed 2.5-bath ranch! Everything you need is on the main level. This home has been thoughtfully renovated, utilizing every square inch. Walk in, and you will appreciate the large entry way ready for your locker system or bench area. The living room is bright and spacious and is open to the kitchen. The kitchen has nice counter and cabinet space with a pantry

Sarah Cowman Homefront Real Estate, LLC

113 S 3rd 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

/26
Est $288,446

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
Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

/35
$350,000

Pending
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
2381 Adair Madison Ave, Winterset, IA 50273

Discover the perfect blend of country living, outdoor recreation, and modern updates with this exceptional 10-acre hobby farm, located just one mile off Highway 92. Step inside the beautifully updated 3-bedroom, 1-bathroom home featuring a comfortable, flowing floor plan. The heart of the home is a large country kitchen with abundant cabinet space and room for a dining table, which seamlessly

Ian Sparks Homefront Real Estate, LLC

2381 Adair Madison 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 $239,742

Not Listed For Sale

715 W North St, Winterset, IA 50273
- 2 Beds
- 2 Baths
- 1,480 Sq Ft
- Built 1890
715 W North St, Winterset, IA 50273

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

/2
$39,900
- Land
- 2.86 Acres
- $13,951 per Acre
1600 Roseman Bridge Rd, Winterset, IA 50273

Discover your little slice of heaven. This opportunity to own a couple acres along the Middle River is a unique one that will allow for many outdoor activities. Want a spot to picnic? have a garden? Maybe you'd like to riverside camp? This gem may be just the ticket! (Address is fictitious and for general location purposes only)

Dan Wilson SoldWilson Real Estate and Auc

1600 Roseman Bridge Rd, Winterset, IA 50273

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Iowa Madison County

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Winterset, IA Homes

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