Winterset, IA Homes

/21
$225,000 Pending
- 3 Beds
- 2 Baths
- 1,174 Sq Ft
110 E Grade St, Winterset, IA 50273

Step into this beautifully remodeled and charming single-story home, thoughtfully designed to combine comfort and modern living. This inviting 3-bedroom, 2-bath residence showcases a spacious eat in kitchen (appliances included) and an airy, naturally lit living room with vaulted ceiling that creates a welcoming atmosphere throughout. This property offers both comfort and function. The primary

Sarah Cowman Homefront Real Estate, LLC

110 E Grade 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 $203,795

Last Listing Agent Sue Monroe Spire Real Estate

417 S 2nd St, Winterset, IA 50273

/20
Est $227,545 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,252 Sq Ft
506 E Filmore St, Winterset, IA 50273

506 E Filmore St, Winterset, IA 50273

/12
$199,900
- Land
- 4.68 Acres
- $42,714 per Acre
2215 245 Ln, Winterset, IA 50273

Beautiful rolling building lot just south of town and on minimal gravel located on a dead end road! This 4.68 acre m/l lot is ready for you to bring your builder and build your dream home! The lot gently rolls to the north for a walk out opportunity and overlooks the neighbor's pristine pond! There will be very minimal covenants (currenty being drawn up by attorney) and the county needs to

Sarah Cowman Homefront Real Estate, LLC

2215 245 Ln, 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 $319,503

Last Listing Agent Amanda Poganski Boutique Real Estate

103 W Lane St, Winterset, IA 50273

/18
Est $218,849 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,248 Sq Ft
510 E Filmore St, Winterset, IA 50273

510 E Filmore St, Winterset, IA 50273

/33
$225,000
- 3 Beds
- 2 Baths
- 2,085 Sq Ft
705 S 2nd St, Winterset, IA 50273

Located in beautiful Winterset, IA, this well-maintained home offers over 2,000 square feet of comfortable living space. Featuring 3 bedrooms and 2 full bathrooms, the home includes a brand-new custom kitchen with updated cabinetry, perfect for everyday living and entertaining. Situated on a large lot with an oversized garage, there's plenty of room for storage, hobbies, and outdoor enjoyment. A

Kyle Kuhns RE/MAX Revolution

705 S 2nd 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 $145,158

Last Listing Agent Randall Henry Madison County Realty

2331 Clark Tower Rd, Winterset, IA 50273

/29
Est $257,087 Not Listed For Sale
- 4 Beds
- 2 Baths
- 946 Sq Ft
311 E Filmore St, Winterset, IA 50273

311 E Filmore St, Winterset, IA 50273

/12
$216,000
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
407 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

407 W Madison St, 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

/20
Est $195,608 Not Listed For Sale
- 2 Beds
- 1 Bath
- 986 Sq Ft
306 E Buchanan St, Winterset, IA 50273

306 E Buchanan St, Winterset, IA 50273

/2
$450,000
- Land
- 30 Acres
- $15,000 per Acre
RR Scott Township None, Winterset, IA 50222

A great opportunity to add to your existing operation or the perfect acreage to start a small farm, a nice building site or weekend gateway. This is a highly productive farm, all tillable with a CSR 2 rating of 83.

Patrick Corkrean Madison County Realty

RR Scott Township None, Winterset, IA 50222
/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

/15
Est $219,730 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
423 E Benton St, Winterset, IA 50273

423 E Benton St, Winterset, IA 50273

/35
$449,900
- 5 Beds
- 3 Baths
- 2,137 Sq Ft
812 N 8th Ave, Winterset, IA 50273

Spacious and inviting, this large ranch in Winterset offers the perfect blend of comfort and style. You will love the stunning stone fireplace as the focal point in the living room with vaulted-ceilings, creating a warm and welcoming atmosphere. The kitchen is nice with granite countertops and plenty of cabinets. The primary bedroom is complete with an ensuite featuring a tile shower with dual

Matt Cole RE/MAX Concepts

812 N 8th Ave, 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 $516,746

Last Listing Agent Jeffrey Longman RE/MAX Precision

2364 Bittersweet Ave, Winterset, IA 50273

/19
Est $185,318 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
715 N 5th St, Winterset, IA 50273

715 N 5th St, Winterset, IA 50273

/12
$220,000
- 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
/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

/25
Est $233,060 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,092 Sq Ft
508 E Lane St, Winterset, IA 50273

508 E Lane St, Winterset, IA 50273

/35
$540,500
- Land
- 23 Acres
- $23,500 per Acre
2571 250th Ln, Winterset, IA 50273

Stunning Executive Building site located just south of Winterset on a dead-end road. If you have been dreaming of a country escape, this is something you need to consider. Approximately 23 acres to be surveyed off will include clean timber, spring-fed creek with well possibilities, wild flowers, limestone ledges, nice rolling pasture, and a stocked pond. Stunning views and wildlife galore!

Sarah Cowman Homefront Real Estate, LLC

2571 250th Ln, 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 $204,812

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

324 W Filmore St, Winterset, IA 50273

/26
Est $230,741 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
622 W Fremont St, Winterset, IA 50273

622 W Fremont St, Winterset, IA 50273

/7
$250,000 Pending
- Land
- 3.75 Acres
- $66,667 per Acre
Lot 18 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 18 114th Ct, 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

/12
Not Listed For Sale
- Studio
- 4 Baths
- 3,600 Sq Ft
602 S 2nd St, Winterset, IA 50273

602 S 2nd St, Winterset, IA 50273

/20
$199,000 Pending
- Land
- 13.6 Acres
- $14,632 per Acre
000 Ivy Trail, Winterset, IA 50273

Want to get out of town to your own serene parklike setting? This place is for you! Build your dream home or just get away from the hustle and bustle of town. Put up a tree stand and try for your trophy buck! No covenants on this property so you can do whatever your heart desires! A creek runs through it, tall hardwood trees and a sweet picnic shelter are all in place. Come get your fill of fresh

Sarah Cowman Homefront Real Estate, LLC

000 Ivy Trail, 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 $783,034

Last Listing Agent Sarah Cowman Homefront Real Estate, LLC

4726 Cherrywood Ln, Winterset, IA 50273

/23
Est $302,946 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,608 Sq Ft
818 W Washington St, Winterset, IA 50273

818 W Washington St, Winterset, IA 50273

/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
/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 $259,205

Last Listing Agent Charles Johnson Kiloterra

2646 Fieldstone Ave, Winterset, IA 50273

/20
Est $230,617 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,130 Sq Ft
824 S 4th Ave, Winterset, IA 50273

824 S 4th Ave, Winterset, IA 50273

/34
$675,000 Pending
- Land
- 5.74 Acres
- $117,596 per Acre
2218 N John Wayne Dr, Winterset, IA 50273

Welcome to this exceptional 3300 sq ft 3/4-bedroom, 4-bath brick ranch that perfectly balances privacy, convenience, and expansive living. Situated on 5+ acres just outside of town, this property offers the best of both worlds—peaceful seclusion with quick access to amenities and major highways. The home boasts a large open-concept living area anchored by a beautiful double-sided fireplace,

Alyssa Tadlock Madison County Realty

2218 N John Wayne Dr, 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

/32
Est $268,664 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
814 S 4th Ave, Winterset, IA 50273

814 S 4th Ave, Winterset, IA 50273

/7
$120,000 Pending
- Land
- 3.57 Acres
- $33,613 per Acre
Lot 38 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 38 Limestone Ct, 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 $305,360

Last Listing Agent Kristen Stehli Real Broker, LLC

522 N 10th St, Winterset, IA 50273

/25
Est $281,914 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,520 Sq Ft
517 W Short St, Winterset, IA 50273

517 W Short St, Winterset, IA 50273

/18
$175,000
- 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

Showing Results 121 - 160, Page 4 of 18

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