Madison, IA Homes

• 

  

  

  /35

  $314,999

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  2385 Holliwell Bridge Rd, Winterset, IA 50273

  Welcome to your dream country retreat! Nestled on 3.17 acres, this beautifully updated 1.5-story home offers the perfect balance of peace, privacy, and convenience—rural living with easy access to town.Step inside to discover thoughtful updates throughout, including a newer roof, all new water lines, updated heating and cooling with a mini-split upstairs, and soaring ceilings that highlight

  Misty Darling BH&G Real Estate Innovations

  2385 Holliwell Bridge Rd, Winterset, IA 50273
• 

  

  

  /35

  $348,000 Sold Jun 20, 2025

  • 1,411 Sq Ft
  • $247/SF
  • 12 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2002

  1303 N 7th St, Winterset, IA 50273

  Welcome to this beautifully maintained 5-bedroom, 3-bath walk-out ranch nestled on a spacious 1-acre corner lot in town! This home offers the perfect blend of comfort, convenience, and charm. Step inside to find a functional and inviting layout, with a new furnace, A/C, water heater, newer roof and newer appliances providing peace of mind for years to come. The walk-out basement adds great living

  Rachel Eller Summerset Realty

  1303 N 7th St, Winterset, IA 50273
• 

  

  

  /16

  Est $215,249 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,016 Sq Ft

  1510 W Jefferson St, Winterset, IA 50273

  1510 W Jefferson St, Winterset, IA 50273
• 

  

  

  /35

  $650,000

  • 4 Beds
  • 3 Baths
  • 1,878 Sq Ft

  1694 McBride Ridge Ct, Winterset, IA 50273

  Acreage for sale in Winterset Iowa! Discover your own slice of country paradise just 100 yards off paved Cumming Road! This 4-bedroom, 3-bath walkout ranch sits on nearly 5 acres—about 90% fenced—and is a dream for nature lovers, hobby gardeners, and dog enthusiasts alike. Built in 2003, this spacious home boasts over 3,300 sq ft of finished living space. The main level features a cozy family

  Michelle Price Realty ONE Group Impact

  1694 McBride Ridge Ct, Winterset, IA 50273
• 

  

  

  /17

  $235,000 Sold Jun 20, 2025

  • Land
  • 35 Acres
  • $6,714 per Acre

  • 333 Days On Market

  2430 Highway 169, Winterset, IA 50273

  This land had been used as a motocross track "Riverside Raceway", and is now being offered as land only. This property includes two parcels, the larger parcel runs along the Middle River south of Winterset and is IDEAL for hunting and recreation, and the smaller adjacent parcel is suitable for building and is NOT in a flood plain. The property is just a couple miles South from the town of

  Keith Soldwisch Zealty Home Advisors

  2430 Highway 169, Winterset, IA 50273
• 

  

  /33

  Est $321,163 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,060 Sq Ft

  215 N 15th Ave, Winterset, IA 50273

  215 N 15th Ave, Winterset, IA 50273
• 

  

  /18

  $73,000

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft

  3028 Carver Rd, Winterset, IA 50273

  Unique opportunity to own an affordable acreage!! NO Covenants!! 2bed/1 bath with bonus loft on +\- half acre in Madison County! 1+ car detached garage. Fenced area for optional livestock or garden.

  Alyssa Tadlock Madison County Realty

  3028 Carver Rd, Winterset, IA 50273
• 

  

  /21

  $515,000 Sold Jun 18, 2025

  • 1,590 Sq Ft
  • $324/SF
  • 19 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2025

  902 S 9th Ave, Winterset, IA 50273

  New construction ranch with a finished walk-out lower level. 4 bedroom, 3 bath, over 2800sf finished. Kitchen features a coffee bar, breakfast bar, walk-in pantry. Great open concept floor plan. The lower level features a large family room and 2 bedrooms with oversized closets. Covered front porch and back deck. Located in a small, quiet residential neighborhood.

  Jennifer Stover Madison County Realty

  902 S 9th Ave, Winterset, IA 50273
• 

  

  /25

  Est $348,951 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,172 Sq Ft

  307 N 14th Ave, Winterset, IA 50273

  307 N 14th Ave, Winterset, IA 50273
• 

  

  /22

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  410 N 6th St, Winterset, IA 50273

  Pride of ownership in this spacious home! 3 bedrooms, 2 baths, over 2,000 sf finished space and a huge backyard. Adorable kitchen with stainless steel appliances. Refrigerator is less than 1 year old. Large dining area with sliding door that leads to the deck/backyard. Great set up for the primary bedroom with access to the bathroom/laundry room. All 3 bedrooms are on the 1st floor. The lower

  Jennifer Stover Madison County Realty

  410 N 6th St, Winterset, IA 50273
• 

  

  /24

  $295,175 Sold Jun 17, 2025

  • 1,609 Sq Ft
  • $183/SF
  • 168 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  5100 Ella Ivy Ct, van Meter, IA 50261

  Welcome to Progressive Builders Madison plan! This Bi-attached townhome is spacious and offers and open concept plan. 3 bedroom and 2 full bathroom upstairs. Huge primary suite with oversized walk in closet. Option to finish an additional 643sq ft in the basement. Built by a local builder, Kimberley Development and backed by a 1yr builder warranty. This home sits on a large lot with 2 car garage.

  Lindsy Baker RE/MAX Concepts

  5100 Ella Ivy Ct, van Meter, IA 50261
• 

  

  /24

  Est $327,961 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,415 Sq Ft

  225 N 14th Ave, Winterset, IA 50273

  225 N 14th Ave, Winterset, IA 50273
• 

  

  /31

  $128,000

  • 2 Beds
  • 1 Bath
  • 942 Sq Ft

  59 E Washington St, Winterset, IA 50273

  Great opportunity for an investor or a first-time buyer looking to make a place their own!! This 942 sq ft ranch-style home offers potential, and an opportunity to build equity with a little TLC. The main level features a spacious living room with built-ins, a generously sized bedroom with double closets, and an eat-in kitchen ready for your personal touch. Toward the back of the home, youll

  John Brummett RE/MAX Precision

  59 E Washington St, Winterset, IA 50273
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  /24

  $350,000 Sold Jun 16, 2025

  • 1,500 Sq Ft
  • $233/SF
  • 2 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1978

  2362 255th St, Peru, IA 50222

  Escape to your own private retreat just south of Winterset with this beautifully maintained ranch-style home nestled on 3 acres of peaceful countryside. Enjoy the serenity of nature and room to roam, all while being just a short drive from town conveniences. This charming home features a functional layout with laundry conveniently located on the main level, spacious bedrooms filled with natural

  Chris Kew RE/MAX Precision

  2362 255th St, Peru, IA 50222
• 

  

  /17

  Est $289,767 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft

  802 N 4th Ave, Winterset, IA 50273

  802 N 4th Ave, Winterset, IA 50273
• 

  

  /25

  $212,000

  • 3 Beds
  • 2 Baths
  • 1,524 Sq Ft

  417 S 2nd St, Winterset, IA 50273

  A must-see home in a fantastic location, just moments from the historic John Wayne birthplace and just blocks away from the bustling downtown square. Walk up to your “new “front porch that welcomes you with new columns, railings, and a porch swing that you'll never want to leave! Perfect spot for your morning coffee , reading your favorite book or lounging at the end of a long day. As you enter,

  Sue Monroe Spire Real Estate

  417 S 2nd St, Winterset, IA 50273
• 

  

  /30

  $246,600 Sold Jun 16, 2025

  • 1,474 Sq Ft
  • $167/SF
  • 49 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1887

  416 N 1st Ave, Winterset, IA 50273

  Charming 3-bedroom Home with Spacious Heated Shop!This well-maintained 3-bedroom 2-bath home offers comfortable living with an added bonus- a 30x32 spray foam insulated and heated shop perfect for hobbies, storage, or a workspace! Inside you'll find a welcoming layout with a bright living area, a functional kitchen, and plenty of natural light. Outside, enjoy a spacious yard with room to relax or

  Rachel Eller Summerset Realty

  416 N 1st Ave, Winterset, IA 50273
• 

  

  /12

  Est $229,462 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,169 Sq Ft

  1002 N 4th Ave, Winterset, IA 50273

  1002 N 4th Ave, Winterset, IA 50273
• 

  

  /10

  $299,000

  • Land
  • 10 Acres
  • $29,900 per Acre

  TBD Iowa 92, Winterset, IA 50273

  Build Your Dream Home on this Scenic 10-Acre Parcel!Located just off paved Highway 92 and only 25 minutes from the Des Moines metro, this beautiful ±10 acre lot offers the perfect mix of convenience and peaceful country living. With scenic views, open space, and rural water and electric at the road, it’s an ideal setting for your future home, hobby farm, or weekend retreat.Plenty of

  Rachel Eller Summerset Realty

  TBD Iowa 92, Winterset, IA 50273
• 

  

  /31

  $395,000 Sold Jun 16, 2025

  • 1,518 Sq Ft
  • $260/SF
  • 67 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1996

  2923 N John Wayne Dr, Winterset, IA 50273

  Here is your chance to live on 3 acres right off of Hwy 169 in Madison County. Check out this updated ranch home featuring 4 bedrooms 3 baths. On the main level you have the Primary suite, with tons of closet space, 2nd bedroom or office. spacious living area with large picture windows, and a large deck off the dining room. On the finished lower level there are 2 additional bedrooms, 2nd family

  Rachel Eller Summerset Realty

  2923 N John Wayne Dr, Winterset, IA 50273
• 

  

  /34

  Est $284,143 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 1,372 Sq Ft

  201 S 14th Ave, Winterset, IA 50273

  201 S 14th Ave, Winterset, IA 50273
• 

  

  /23

  $320,000

  • 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 great big 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

  Alyssa Tadlock Madison County Realty

  203 W Green St, Winterset, IA 50273
• 

  

  /35

  $750,000 Sold Jun 13, 2025

  • 1,534 Sq Ft
  • $489/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  2176 148th St, Winterset, IA 50273

  This M/L 18 acres has something for everyone! You have the wildlife, timber, a pond for fishing, grass & alfalfa mix for your horses or to sell. A nice almost new 30 by 40 pole barn with 2 >10ft by 10ft doors, a concrete floor, electric and outside RV hookups. A detached 2 car garage, 2 sheds, ample parking for extra trailers and several fruit trees. The home has over 2600 sq foot of finished

  Lisa Pierce Honer Summit Realty

  2176 148th St, Winterset, IA 50273
• 

  

  /33

  Est $184,406 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 876 Sq Ft

  205 S 16th Ave, Winterset, IA 50273

  205 S 16th Ave, Winterset, IA 50273
• 

  

  /22

  $134,900

  • 2 Beds
  • 2 Baths
  • 1,093 Sq Ft

  103 S 3rd St, Winterset, IA 50273

  Previously used as an up-and-down duplex, this property offers a flexible layout and a spacious open floor plan. The living room is generously sized. While the home does need some work, it presents a great opportunity for customization or investment. Additional features include an attached one-car garage for convenient parking or storage. Great location.

  Zineta Imamovic Realty ONE Group Impact

  103 S 3rd St, Winterset, IA 50273
• 

  

  /25

  $213,865 Sold Jun 13, 2025

  • 1,061 Sq Ft
  • $202/SF
  • 13 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1910

  707 E Buchanan St, Winterset, IA 50273

  Fully remodeled 3 bedroom 1 bathroom 2 stall garage home in Winterset! Spacious living room with windows all around offering so much natural light! New kitchen!! New cabinets, new countertops, and new appliances in this kitchen offering plenty of cabinet and countertop space! All new appliances also included in this home! One bedroom on the main level, along with the full bathroom with laundry

  Jenn Ho Goh GoSynergy Realty

  707 E Buchanan St, Winterset, IA 50273
• 

  

  /29

  Est $473,126 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,484 Sq Ft

  1515 W Washington St, Winterset, IA 50273

  1515 W Washington St, Winterset, IA 50273
• 

  

  /35

  $659,900

  • 4 Beds
  • 3 Baths
  • 1,788 Sq Ft

  2626 160th St, van Meter, IA 50261

  Rural Madison County Acreage! Open concept Ranch with a little more than 1800 square feet upstairs with a finished basement. Upstairs consists of large master bedroom with tray ceiling and his and her closets. Primary bedroom is huge and has its own bathroom with jetted tub, walk in shower and built in make up counter, toilet has an individual door for that added privacy. Large bedroom and

  Sarah Cowman Homefront Real Estate, LLC

  2626 160th St, van Meter, IA 50261
• 

  

  /25

  $615,000 Sold Jun 13, 2025

  • Land
  • 80 Acres
  • $7,688 per Acre

  • 296 Days On Market

  3057 332nd St, Truro, IA 50257

  Two parcels-40 acres each. Prime hunting with deer trails, wooden deer stands included, double gated access with drive path to barn with working electricity, perimeter barbed wire fenced, all wooded, 2 creeks, ravine. Barn needs repair and roof. Grassy areas lined with berries attract deer naturally, CRP and Homestead credits.

  Dean Siegler Keller Williams Realty GDM

  3057 332nd St, Truro, IA 50257
• 

  

  /23

  Est $253,424 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,270 Sq Ft

  1413 W Washington St, Winterset, IA 50273

  1413 W Washington St, Winterset, IA 50273
• 

  

  /28

  $550,000

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft

  715 N John Wayne Dr, Winterset, IA 50273

  Super unique investment opportunity! This property consists of a residential house and 4 rental units. The house is 1728 sf with 3 bedrooms, 2 bathrooms, 2 family rooms, 1st floor laundry, basement, 2 car garage. The lower level of the house also has 1 bedroom, bath, kitchen, fireplace. You could also rent out the LL of the house. Making total number of units available for rent: 6. The owners

  Jennifer Stover Madison County Realty

  715 N John Wayne Dr, Winterset, IA 50273
• 

  

  /35

  $505,000 Sold Jun 11, 2025

  • 1,411 Sq Ft
  • $358/SF
  • 33 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 2001

  3019 220th St, Saint Charles, IA 50240

  Acreage lookers stop everything, this is the home you've been waiting for! 2,800 total finished square feet, 1,400 upstairs and another 1,400 down. This walkout ranch on 5 acres has been completely remodeled and is just waiting for the perfect owner. The home sits atop of the property and looks down upon sprawling, rolling hills. The sunsets from your deck are absolutely phenomenal! Inside, the

  Michael Fagerstrom Keller Williams Realty GDM

  3019 220th St, Saint Charles, IA 50240
• 

  

  /32

  Est $440,330 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,051 Sq Ft

  924 Husky Dr, Winterset, IA 50273

  924 Husky Dr, Winterset, IA 50273
• 

  

  /33

  $199,000

  • 4 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  455 NW 2nd St, Earlham, IA 50072

  Welcome to Earlham! This large two-story home in a small, quiet town within 30 mins of the Des Moines metro. This property has had many recent updates and is ready for you! On this home's main level, you will find an open living/dining area with LVP flooring. The bathroom has a beautiful claw foot tub. On the second level is another bathroom and 3 bedrooms. Oversized 2 car garage. Pre-inspected

  Tasha Garlick RE/MAX Concepts

  455 NW 2nd St, Earlham, IA 50072
• 

  

  /21

  $225,000 Sold Jun 11, 2025

  • 960 Sq Ft
  • $234/SF
  • 107 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1976

  703 N 3rd Ave, Winterset, IA 50273

  You will want to check out this well kept 3 bedroom home with finished basement on a corner lot. Home features 3 bedrooms and one bath on the main level. The kitchen is bright and nicely updated with newer appliances which are included! The dining area is adjacent to the kitchen which has a door that leads to the huge deck - perfect for grilling! The living room is very large with a big bright

  Sarah Cowman Homefront Real Estate, LLC

  703 N 3rd Ave, Winterset, IA 50273
• 

  

  /19

  Est $274,077 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft

  1018 N 3rd Ave, Winterset, IA 50273

  1018 N 3rd Ave, Winterset, IA 50273
• 

  

  /13

  $159,900

  • 5 Beds
  • 2 Baths
  • 1,556 Sq Ft

  523 S 2nd St, Winterset, IA 50273

  This conversion duplex offers the perfect opportunity to add value and generate strong returns. Located just blocks from downtown Winterset, this property is ideal for house hackers, investors, or anyone looking to expand their portfolio in a growing community. Each unit offers spacious layouts with room for updates and personalization. With separate entrances, utilities, and off-street parking

  Ben Grotzke LPT Realty, LLC

  523 S 2nd St, Winterset, IA 50273
• 

  

  /24

  $280,000 Sold Jun 11, 2025

  • 2,212 Sq Ft
  • $127/SF
  • 271 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1930

  217 E Jefferson St, Winterset, IA 50273

  Seller offering $5000 worth of buyer’s concessions for closing costs or beautification to make home their own! Unique property; two homes 1 lot. Main home is 5 bedroom, 2 remodeled baths with new carpet and flooring throughout. Kitchen has been remodeled with new cabinets, new dishwasher w/warranty and new stove and refrigerator. New Washer and Dryer are also included! Other updates in the main

  Sarah Cowman Homefront Real Estate, LLC

  217 E Jefferson St, Winterset, IA 50273
• 

  

  /21

  Est $284,316 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft

  926 N 3rd Ave, Winterset, IA 50273

  926 N 3rd Ave, Winterset, IA 50273
• 

  

  /35

  $155,000

  • 3 Beds
  • 1 Bath
  • 2,124 Sq Ft

  513 W Vine St, Saint Charles, IA 50240

  Start with the large lot and then add the over 2000 square foot house and the potential is obvious. The attached 3 car garage, large rooms, amazing breezeway, large front and rear decks, high ceilings and original charm add to the opportunity. Bring your vision and abilities and make this home, YOURS! There is a LOT to work with and improve. Set up a showing, TODAY, as this one will move quickly.

  Tanner Loyd Iowa Realty Indianola

  513 W Vine St, Saint Charles, IA 50240

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