Madison, IA Homes

• 

  

  

  /22

  $212,000

  • 3 Beds
  • 1 Bath
  • 1,088 Sq Ft

  1424 W Jefferson St, Winterset, IA 50273

  Well-maintained and beautifully landscaped 3-bedroom, 1-bath home with a walk-in shower. Recent updates include furnace, AC, windows, and siding. Conveniently located near the Aquatic Center and other community amenities in Madison County.

  Rachel Eller Summerset Realty

  1424 W Jefferson St, Winterset, IA 50273
• 

  

  

  /22

  $270,000 Sold Jul 11, 2025

  • 1,140 Sq Ft
  • $237/SF
  • 2 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1968

  616 E Green St, Winterset, IA 50273

  Spread out in this sweet 4 bedroom 2 bath ranch home. You will love the spacious feel when you walk in the front door. The entryway is spacious and has a huge coat closet. The living room is good-sized and has an adjacent dining area. The kitchen is huge - enough space for a table or center island. There are 3 spacious bedrooms and a full bath completing the main level. The basement is finished

  Sarah Cowman Homefront Real Estate, LLC

  616 E Green St, Winterset, IA 50273
• 

  

  

  /27

  Est $249,352 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,452 Sq Ft

  1215 W Washington St, Winterset, IA 50273

  1215 W Washington St, Winterset, IA 50273
• 

  

  

  /27

  $210,000

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft

  202 S 7th Ave, Winterset, IA 50273

  Full of character and charm, this home sits on a desirable corner lot in the heart of Winterset Step inside to bright living spaces with new flooring throughout. The functional kitchen features ample storage and prep space and opens to the dining room. An inviting 3 season room steps from the living room and adjoined to the garage offers the perfect bonus space for entertaining or quiet mornings.

  Tiffany Ehler Boutique Real Estate

  202 S 7th Ave, Winterset, IA 50273
• 

  

  

  /32

  $160,000 Sold Jul 08, 2025

  • 2,018 Sq Ft
  • $79/SF
  • 41 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1922

  415 E Jefferson St, Winterset, IA 50273

  Are you looking for a large 4 bed/1.5 bath home with plenty of character, in the beautiful town of Winterset? Then this is the house for you. From the beautiful oak hardwood floors to the built-in corner cabinet in the dining area, and all of the smaller windows that bring in plenty of natural light, you will want to call this house HOME. The roomy kitchen has new stainless-steel appliances and

  Betsy Breeding Realty ONE Group Impact

  415 E Jefferson St, Winterset, IA 50273
• 

  

  /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
• 

  

  /27

  $247,900

  • 3 Beds
  • 2 Baths
  • 1,106 Sq Ft

  316 E Jefferson St, Winterset, IA 50273

  Charming Victorian that has been fully renovated. The living room has ten-foot ceilings, beautiful chandeliers, and a gas fireplace. In the main bedroom, there is a unique stained glass window. Walking into the kitchen, you are greeted with quartz countertops and custom cabinets, which adds a modern touch. All the appliances are 2-3 years old. Washer/dryer hookups are in the basement along with a

  Tamra Yeager Pro Team Realty

  316 E Jefferson St, Winterset, IA 50273
• 

  

  /22

  $525,000 Sold Jul 08, 2025

  • 1,911 Sq Ft
  • $275/SF
  • 98 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2020

  1785 Millstream Ct, Winterset, IA 50273

  Custom built and absolutely stunning, this three-bedroom, ranch home sitting on 3 acres with paved roads is in A+ condition! Walls of floor to ceiling windows flood the home with natural light and provide amazing sunset views of the valley. 2x6 quality construction, with clean, modern lines. Finishes are high end and the floor plan and space is perfect for right sizing, or a family. Radiant floor

  JoAnn Manning Iowa Realty Mills Crossing

  1785 Millstream Ct, 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
• 

  

  /16

  $150,000

  • Land
  • 3.49 Acres
  • $42,980 per Acre

  Lot 7 114th Ct, Winterset, IA 50273

  Build your luxury retreat on this 3.5-acre Website for the development is: Scenic Ridge lot,offering sweeping views of Madison County’s rolling hills at the gateway to the Covered Bridge Scenic Byway.Enjoy upscale living with premier shopping, dining, and entertainment at Jordan Creek and KeeTown less than 20 minutes away.

  Latrice Brauckman Realty ONE Group Impact

  Lot 7 114th Ct, Winterset, IA 50273
• 

  

  /21

  $139,900 Sold Jun 30, 2025

  • 672 Sq Ft
  • $208/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1947

  215 S 2nd St, Winterset, IA 50273

  Welcome to historic Winterset! This updated 2-bed, 1-bath home is move-in ready with a new furnace and AC (2020), updated roof, fresh paint, and new flooring. The spacious backyard features a courtyard with pergola, new shed, and full privacy fence—perfect for relaxing or entertaining.Ideal for first-time buyers, downsizers, or as a short-term rental. Includes an HSA home warranty for

  Nicholas Scar Iowa Realty Mills Crossing

  215 S 2nd 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
• 

  

  /20

  $139,500

  • Land
  • 4.15 Acres
  • $33,614 per Acre

  TBD 176th Ct, Winterset, IA 50273

  Located just 2 miles north of Winterset and just east off Highway 169, this 4.15-acre property offers a rare opportunity to build your dream home in a scenic setting.Perched on a hillside overlooking the beautiful North River Valley, the property features two potential build site locations with breathtaking views. With utilities available at the highway, the groundwork is set for an easy

  Colin Ortmeier Kiloterra

  TBD 176th Ct, Winterset, IA 50273
• 

  

  /9

  $22,000 Sold Jun 30, 2025

  • 1,031 Sq Ft
  • $21/SF
  • 19 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 2025

  415 E 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

  415 E Madison St, Winterset, IA 50273
• 

  

  /34

  Est $560,368 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths

  1145 W Summit St, Winterset, IA 50273

  1145 W Summit St, Winterset, IA 50273
• 

  

  /9

  $140,000

  • Land
  • 4.32 Acres
  • $32,407 per Acre

  0000 Saint Charles Rd, Winterset, IA 50273

  Build your dream home on this private 4.2 acre parcel with beautiful views overlooking the Middle River Valley. On hard surface with rural water and electric at the street. Close to Winterset and easy commute to Des Moines.

  Katie Bloom LPT Realty, LLC

  0000 Saint Charles Rd, Winterset, IA 50273
• 

  

  /31

  $310,000 Sold Jun 30, 2025

  • 1,415 Sq Ft
  • $219/SF
  • 54 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 2002

  221 N 15th Ave, Winterset, IA 50273

  Welcome to your future home in the heart of Winterset! This beautiful 1.5-story home offers 1,415 sq ft of living space, featuring 5 bedrooms, 2.5 bathrooms, an attached 2-car garage, and a fully fenced backyard with a spacious deck—ideal for enjoying the outdoors.The main level includes the master bedroom and first-floor laundry for your everyday convenience.Just minutes away

  Danielle Burnight RE/MAX Revolution

  221 N 15th Ave, Winterset, IA 50273
• 

  

  /33

  Est $335,063 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,102 Sq Ft

  1169 W Summit St, Winterset, IA 50273

  1169 W Summit St, Winterset, IA 50273
• 

  

  /11

  $655,384

  • Land
  • 96 Acres
  • $6,819 per Acre

  00 Millstream Ave, Winterset, IA 50273

  Premium Row Crop Ground with Endless Potential | Madison County, IowaRepresenting the Utsler Family Trust in the sale of 50.51 gross acres m/l located in Section 18 of Scott Township in Madison County. This farm consists of an estimated 48.19 FSA cropland acres currently in row crop production boasting highly productive soils including Sharpsburg, Macksburg, and Clearfield silty clay

  Andrew Zellmer Peoples Company

  00 Millstream Ave, Winterset, IA 50273
• 

  

  /26

  $337,000 Sold Jun 27, 2025

  • 2,267 Sq Ft
  • $149/SF
  • 1 Day On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1972

  925 W Jefferson St, Winterset, IA 50273

  One of the homes with the best curb appeal in town has just hit the market! This spacious 1.5-story Cape Cod-style home is clean, tidy, and ready for a new owner. Walk up to the inviting front porch and enter the foyer. The spacious living room, featuring a picture window, will greet you as you enter. The formal dining room is off the living room & adjacent to the spacious kitchen with lots of

  Sarah Cowman Homefront Real Estate, LLC

  925 W Jefferson St, Winterset, IA 50273
• 

  

  /25

  Est $480,179 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,595 Sq Ft

  614 W Benton St, Winterset, IA 50273

  614 W Benton St, Winterset, IA 50273
• 

  

  /4

  $74,500

  • Land
  • 3.00 Acres
  • $24,833 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! Enjoy paved roads, rural water access at the road, and peaceful surroundings in this established neighborhood. Just minutes from town, with easy access to

  Rachel Eller Summerset Realty

  1796 Millstream Ct, Winterset, IA 50273
• 

  

  /35

  $506,942 Sold Jun 26, 2025

  • 1,312 Sq Ft
  • $386/SF
  • 2 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2013

  2364 Bittersweet Ave, Winterset, IA 50273

  Are you looking for complete privacy? Do you enjoy being surrounded by nature and wildlife? This is the acreage you have been looking for! This modern ranch home features 3 bedrooms, 3 bathrooms, and fully finished walkout basement. The main floor includes an open kitchen and living area, separate master suite, two additional bedrooms and bathroom, laundry, and a deck off of the dining area. The

  Jeffrey Longman RE/MAX Precision

  2364 Bittersweet Ave, Winterset, IA 50273
• 

  

  /3

  Est $131,410 Not Listed For Sale

  1019 N 4th Ave, Winterset, IA 50273

  1019 N 4th Ave, Winterset, IA 50273
• 

  

  /35

  $850,000

  • 3 Beds
  • 3.5 Baths
  • 3,298 Sq Ft

  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 private acreage within city limits but just outside of town, this property offers the best of both worlds—peaceful seclusion with quick access to amenities and major highways.From the moment you step through the grand entry, you'll appreciate

  Alyssa Tadlock Madison County Realty

  2218 N John Wayne Dr, Winterset, IA 50273
• 

  

  /29

  $215,000 Sold Jun 26, 2025

  • 1,673 Sq Ft
  • $129/SF
  • 27 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1944

  315 W Washington St, Winterset, IA 50273

  Welcome to your dream home in the heart of Winterset! This charming and spacious brick ranch offers everything you need for comfortable, convenient living. As soon as you step inside, you will be greeted by beautiful hardwood floors that flow throughout the main level. No more carrying laundry up and down stairs - this home features a main level laundry with the option to easily move it

  Misty Darling BH&G Real Estate Innovations

  315 W Washington St, Winterset, IA 50273
• 

  

  /20

  Est $250,537 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  501 W Buchanan St, Winterset, IA 50273

  501 W Buchanan St, Winterset, IA 50273
• 

  

  /18

  $195,000

  • Land
  • 4.88 Acres
  • $39,959 per Acre

  4922 Cedar Ln, Winterset, IA 50273

  Looking for the perfect mix of privacy, space, and convenience? This stunning 4.88-acre lot at the end of a quiet cul-de-sac offers just that. Located on a paved road between West Des Moines and Winterset, this property features a beautiful blend of open grassland and mature timber, ideal for creating your custom retreat.There's room for it all: your dream home, an outbuilding, or even a

  Timothy Scheib RE/MAX Precision

  4922 Cedar Ln, 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
• 

  

  /22

  Est $225,943 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  618 N 4th Ave, Winterset, IA 50273

  618 N 4th Ave, Winterset, IA 50273
• 

  

  /29

  $217,400

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  66 E High St, Winterset, IA 50273

  Charming and fully updated 1.5 story home on a large corner lot in historic Winterset--roughly 30 minutes from the Des Moines metro! This 3-bed, 2-bath home features a spacious living room and a wrap-around layout that flows seamlessly from the living area to the updated kitchen with newer stainless steel appliances, and into the dining space. Stylish LVP flooring throughout the main level adds

  Cameron Campos RE/MAX Concepts

  66 E High St, 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
• 

  

  /25

  Est $216,737 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  1016 W South St, Winterset, IA 50273

  1016 W South St, Winterset, IA 50273
• 

  

  /30

  $289,000

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft

  701 W Buchanan St, Winterset, IA 50273

  Easy living in this Ranch with many updates including roof, siding, gutters, furnace, a/c in 2021, yard drainage system, and updates to the electrical. This unique ranch home has a large front porch that is great for sipping coffee and chatting with the neighbors! Inside you will love the large front living room with wood burning fireplace that is adjacent to the formal dining room that flows

  Sarah Cowman Homefront Real Estate, LLC

  701 W Buchanan St, 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
• 

  

  /21

  Est $207,252 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 964 Sq Ft

  110 N 10th Ave, Winterset, IA 50273

  110 N 10th Ave, Winterset, IA 50273
• 

  

  /21

  $180,000

  • 3 Beds
  • 1 Bath
  • 1,222 Sq Ft

  601 E Green St, Winterset, IA 50273

  This beautifully updated 3-bedroom, 1-bath farmhouse at 601 E Green St offers 1,222 sq ft of thoughtfully designed living space. Full of character, the home features an eat-in kitchen, a cozy living room with plenty of natural light, and a bonus room that can easily serve as an office or an extra bedroom. The updated bathroom and fresh flooring throughout the main level add modern convenience.

  Theodore Craig Developers Realty Group LLC

  601 E Green 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
• 

  

  /24

  Est $258,000 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,260 Sq Ft

  906 W Court Ave, Winterset, IA 50273

  906 W Court Ave, Winterset, IA 50273
• 

  

  /14

  $235,000

  • 3 Beds
  • 1.5 Baths
  • 912 Sq Ft

  1021 W South St, Winterset, IA 50273

  Come enjoy small town living in Winterset in this adorable 3 bedroom ranch home! The spacious living area has tons of natural light with the large windows and beautiful hardwood floors. Find three bedrooms and a full bath on the main floor, as well as the farmhouse style kitchen featuring white subway tile backsplash and white cabinets. The lower level features an extra living space, half bath,

  Jenna Carney Keller Williams Realty GDM

  1021 W South St, Winterset, IA 50273

Showing Results 81 - 120, Page 3 of 18