Winterset, IA Homes

/28
$349,900

$15K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,669 Sq Ft
1514 MacKensie Cir, Winterset, IA 50273

Spacious 2 story home in the Birchwood development. 3 bedrooms, 2.5 baths, 1669sf. Modern open floor plan. Large kitchen and dining area. Sliding door from dining area leads to the deck. Just off the kitchen is a home office/formal dining room. The 2nd floor features 3 generous bedroom, 2 baths, and laundry room. The lower level is ready for the new homeowners to finish for even more living

Jennifer Stover Madison County Realty

1514 MacKensie Cir, Winterset, IA 50273
/28
$250,000

Sold Jun 16, 2026

613 E Buchanan St, Winterset, IA 50273
- 3 Beds
- 2 Baths
- 1,878 Sq Ft
- Built 1890
Last Sold Summary
- $133/SF
- 1 Day On Market
Current Estimated Value $244,264

Last Listing Agent Payton Coyle Century 21 Signature

613 E Buchanan St, 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

/34
$349,900

Pending
- 4 Beds
- 2.5 Baths
- 1,833 Sq Ft
724 W Buchanan St, Winterset, IA 50273

Completely renovated 4-bedroom, 2-bath home featuring extensive interior and exterior improvements, along with major structural upgrades that provide long-term peace of mind. Thoughtfully updated from top to bottom, the home offers all new flooring throughout, creating a seamless and modern feel across the main living areas, bedrooms, and finished basement. The bathrooms have been fully remodeled

Ben Flurey A.I.M. Real Estate & Consultin

724 W Buchanan 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

/20
Est $208,616

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

/34
$239,000
- 3 Beds
- 2.5 Baths
- 1,246 Sq Ft
207 E Buchanan St, Winterset, IA 50273

Now this is a home you'll want to show off! A historic Frame House in the heart of Winterset, fully renovated & remarkably designed. Huge curb appeal, mature trees, brand new front deck. Inside is a beautiful entry that leads to a stunning, expansive living room with original shiplap ceiling, tons of natural light. Gorgeous, grand dining room. The kitchen meets your needs & has tons of style. New

Alison Frank Platinum Realty LLC

207 E Buchanan 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 $199,742

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

110 E Grade St, Winterset, IA 50273

/32
Est $231,414

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

/3
$140,000

Pending
- Land
- 3.68 Acres
- $38,043 per Acre
1804 N 8th St, Winterset, IA 50273

Bring your own builder and build your dream home on this beautiful lot just on the northside of Winterset! As you pull into the shared driveway you will love that you are so close to town but have space to spread out! This land gently slopes to the west so a daylight or walk out basement is a possibility! You will love watching the sun setting over the neighbor's pond! It is currently being

Sarah Cowman Homefront Real Estate, LLC

1804 N 8th St, 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 $230,602

Last Listing Agent Kyle Kuhns RE/MAX Revolution

705 S 2nd St, Winterset, IA 50273

/25
Est $284,461

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

/7
$149,000
- Land
- 2.93 Acres
- $50,853 per Acre
Lot 35 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 35 Limestone Ct, 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 $203,646

Last Listing Agent Toni Tindle Covered Bridge Realty

827 W Fremont 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

/35
$339,900

$10K PRICE DROP Pending
- 2 Beds
- 2 Baths
- 1,024 Sq Ft
2197 175th Ct, Winterset, IA 50273

Want to own a slice of Heaven?! This is it! Fully renovated acreage just off pavement about 3 miles north of charming and growing Winterset and about 7 miles south of DeSoto and I80. Spacious ranch alongside the North River with stunning finishings. Open concept at its finest with vaulted ceilings and daylight everywhere you look! Incredible kitchen that you'll want to show off as you host all

Ambria Vogt RE/MAX Precision

2197 175th Ct, 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 $244,789

Last Listing Agent Toni Tindle Covered Bridge Realty

609 E Filmore St, Winterset, IA 50273

/26
Est $267,984

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

/5
$159,900

Pending
- 3 Beds
- 1 Bath
- 1,152 Sq Ft
510 E Court Ave, Winterset, IA 50273

3-bedroom ranch with a 2-car detached garage offering tons of potential! Recent updates include a new roof, exterior paint, boiler, and garage door. Home is in need of TLC and cosmetic updates but provides a great opportunity for buyers looking to add their own touch. Solid bones with plenty of possibilities! photos coming soon

Rachel Eller Summerset Realty

510 E Court Ave, Winterset, IA 50273
/33
$220,000

Sold Aug 26, 2025

1755 280th St, Winterset, IA 50273
- 3 Beds
- 1 Bath
- 942 Sq Ft
- Built 1900
Last Sold Summary
- 12% Below List Price
- $234/SF
- 85 Days On Market
Current Estimated Value $185,434

Last Listing Agent Toni Tindle Covered Bridge Realty

1755 280th St, Winterset, IA 50273

/26
Est $224,343

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

/29
$289,000

$10K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,080 Sq Ft
203 W Green St, Winterset, IA 50273

You will love all the space in this UNIQUE 2000+ sq ft home on a large corner lot! Main level includes a massive family room, large kitchen with dinning area and a separate room that could be a formal dining room or office and a half bath. Upstairs there are 3 large bedrooms (one with en suite and walk in closet) plus another smaller room that could also be a bedroom, game room, office or craft

Alyssa Tadlock Madison County Realty

203 W Green St, 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 $244,962

Last Listing Agent Sara Hopkins RE/MAX Precision

114 N 8th Ave, Winterset, IA 50273

/15
Est $239,328

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

/7
$240,000

$10K PRICE DROP
- Land
- 4.19 Acres
- $57,279 per Acre
Lot 17 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 17 114th Ct, 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 $451,212

Last Listing Agent Matt Cole RE/MAX Concepts

812 N 8th Ave, Winterset, IA 50273

/17
Est $196,441

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

/2
$855,422

Pending
- 5 Beds
- 4.5 Baths
- 2,824 Sq Ft
1136 Limestone Ct, Winterset, IA 50273

Sage Homes BTO- Walnut Plan

Kristina Leek RE/MAX Precision

1136 Limestone Ct, 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 $508,177

Last Listing Agent Cindy Miller Keller Williams Realty GDM

2155 148th St, Winterset, IA 50273

/28
Est $254,546

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

/7
$220,000

$55K PRICE DROP
- Land
- 4.22 Acres
- $52,133 per Acre
Lot 31 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 31 Limestone Ct, 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

/31
Est $330,118

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

/7
$250,000
- Land
- 3.33 Acres
- $75,075 per Acre
Lot 22 112th 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 22 112th Ct, Winterset, IA 50273
/12
$1,300,000

Sold Jul 17, 2025

RR Millstream Ave, Winterset, IA 50273
- Land
- 172.1 Acres
- $7,554 per Acre
Last Sold Summary
- 11% Below List Price
- 41 Days On Market
Last Listing Agent Larry Corkrean Madison County Realty

RR Millstream Ave, Winterset, IA 50273

/29
Est $303,696

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

/2
$125,000
- Land
- 31,798 Sq Ft
- $171,233 per Acre
Lot 3 N 4th Ave, Winterset, IA 50273

New Light Commercial Development. Lots will be ready to build upon in Spring 2025, Road is being paved in Fall 2024. All utilities to the lots. Great location for easy access to major highways. Listing agent has ownership in the property.

Peter Corkrean Madison County Realty

Lot 3 N 4th Ave, Winterset, IA 50273
/31
$226,000

Sold Aug 08, 2025

318 W Green St, Winterset, IA 50273
- 3 Beds
- 1.5 Baths
- 1,584 Sq Ft
- Built 1900
Last Sold Summary
- 3% Below List Price
- $143/SF
- 43 Days On Market
Current Estimated Value $232,890

Last Listing Agent Toni Tindle Covered Bridge Realty

318 W Green St, Winterset, IA 50273

/14
Est $142,961

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

/4
$55,000

$20K PRICE DROP
- Land
- 3 Acres
- $18,333 per Acre
1796 Millstream Ct, Winterset, IA 50273

Beautiful 3-acre lot located in the desirable Covered Bridge Estates! This scenic property offers the perfect blend of country feel with community convenience. Ideal for building your dream home with room to spread out—bring your own builder! Limestone is present. Enjoy paved roads, rural water access at the road, and peaceful surroundings in this established neighborhood. Just minutes from town,

Rachel Eller Summerset Realty

1796 Millstream Ct, Winterset, IA 50273

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Iowa Madison County Winterset

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