Madison, IA Homes

• 

  

  

  /25

  $192,000

  • 2 Beds
  • 1 Bath
  • 1,030 Sq Ft

  507 W Madison St, Winterset, IA 50273

  EZ living on one level! This 2 bedroom, 1 bath triplex has center location which is very quiet and economical.Kitchen has an open floor plan to living area boasting vaulted ceilings. Handy pantry closet located in kitchen.Features include: 36-inch doorways throughout, easy access to tiled walk-in shower, master bedroom has large walk-in closet with access from bathroom and bedroom, trey

  

  Toni Tindle

  Covered Bridge Realty

  (515) 385-4853

  507 W Madison St, Winterset, IA 50273
• 

  Explore Winterset

• 

  

  

  /18

  $800 - $995 per month

  The Bridges

  1 - 2 Beds

  1111 N 8th Ave, Winterset, IA 50273

  Formerly Known as Candle Ridge, The Bridges, an Apartment Community, offers affordable 1 and 2 bedroom apartments. Apartments are being freshened up with brand-new LVP flooring, updated cabinetry, and counters. Age restrictions no longer apply!

  1111 N 8th Ave, Winterset, IA 50273
• 

  

  

  /31

  $477,500 Sold Aug 01, 2025

  • 1,597 Sq Ft
  • $299/SF
  • 23 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2023

  519 W Mills St, Winterset, IA 50273

  Better Than New – Modern Elegance in a Serene Setting. Step into modern luxury with this stunning 4-bedroom, 3-bathroom home nestled in an established neighborhood and backing to mature trees for added privacy. From the moment you approach the front entrance, you'll be captivated by its sleek, contemporary design and inviting curb appeal. The main level features a spacious open-concept layout

  Renee Dunkel Century 21 Signature

  519 W Mills St, Winterset, IA 50273
• 

  

  

  /21

  Est $166,175 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,324 Sq Ft

  520 N 3rd Ave, Winterset, IA 50273

  520 N 3rd Ave, Winterset, IA 50273
• 

  

  

  /31

  $234,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  318 W Green St, Winterset, IA 50273

  Appealing 1.5 story 3 - bedroom home on Winterset West side close to historic square. Welcoming covered front porch makes a perfect place to enjoy spending more time outdoors. Interior includes one BR on the main floor with corner closet allowing additional storage. This room would also make a great office space. Updated kitchen with bright south facing custom window, newer appliances and

  

  Toni Tindle

  Covered Bridge Realty

  (515) 375-1789

  318 W Green St, Winterset, IA 50273
• 

  

  /4

  $545 - $790 per month

  Historic Winterset High School Apartments 55+

  Studio - 2 Beds

  110 W Washington St, Winterset, IA 50273

  Call today to learn more about Historic Winterset High School Apartments Senior 55+ , NOW LEASING for June 1, 2024!

  110 W Washington St, Winterset, IA 50273
• 

  

  /26

  $289,500 Sold Aug 01, 2025

  • 1,344 Sq Ft
  • $215/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2008

  902 W Filmore St, Winterset, IA 50273

  WELCOME TO WINTERSET! Beautiful, well maintained, townhome has a nice open floor plan with plenty of natural light. The large living room, with gas fireplace, opens up to the dining area and kitchen, great for entertaining. The nice sized kitchen, with plenty of cabinets and a pantry, has beautiful new quartz countertops. All the flooring is new as well, including the water resistant/scratch

  Betsy Breeding Realty ONE Group Impact

  902 W Filmore St, Winterset, IA 50273
• 

  

  /23

  Est $181,007 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 981 Sq Ft

  201 S 4th St, Winterset, IA 50273

  201 S 4th St, Winterset, IA 50273
• 

  

  /28

  $274,000

  • 4 Beds
  • 2 Baths
  • 1,104 Sq Ft

  609 E Filmore St, Winterset, IA 50273

  Recently updated ranch style home with 4 bedrooms and 2 baths. Interior includes three BR’s on the main floor, living room, and kitchen just off attached one car garage. One bedroom on the main level would also make a perfect office space and was previously used as a sewing room. All bedrooms have generous sized closets. Updated kitchen with bright south facing over the sink window, included

  

  Toni Tindle

  Covered Bridge Realty

  (515) 495-5285

  609 E Filmore St, Winterset, IA 50273
• 

  

  /14

  $1,035 per month

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • House for Rent

  609 W Buchanan St, Winterset, IA 50273

  Cute home on a quiet street; your neighbors are friendly and welcoming! This home features 2 adequately sized bedrooms and a full bath all on one level, including a washer and dryer. Central air conditioning will keep you cool. Water softener also included. Has a backyard storage shed for your lawn mower, tools, etc. Nice peaceful backyard with surrounding trees and a peach tree also included

  609 W Buchanan St, Winterset, IA 50273
• 

  

  /35

  $1,150,000 Sold Aug 01, 2025

  • 2,244 Sq Ft
  • $512/SF
  • 47 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2016

  1720 Merriam Ct, Winterset, IA 50273

  Spectacular acreage near Winterset with gorgeous 4+Bedroom/4 Bath home on 21+acres, including hunt-able private timber ground. It’s the details that make this property so special. Enjoy numerous outdoor spaces: covered deck with view of 2 ponds (1 is stocked), a covered patio, outdoor fireplace on fabulous open patio, large Pole Barn for all your hobbies, toys and tools and a 3+car tandem

  Nancy Shrader Keller Williams Ankeny Metro

  1720 Merriam Ct, Winterset, IA 50273
• 

  

  /12

  Est $239,484 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,184 Sq Ft

  816 E South St, Winterset, IA 50273

  816 E South St, Winterset, IA 50273
• 

  

  /30

  $474,000

  • 3 Beds
  • 3 Baths
  • 2,389 Sq Ft

  1913 N 1st St, Winterset, IA 50273

  Hard to find home on this parcel just N of Winterset 4-way intersection of Hwy 92 & 169. This home has 3BR's & 3 baths sitting on nearly an acre. Kitchen has had a complete remodel including adding a convenient island & farm sink. Master BR on 1st floor has large walk-in closet, and tiled walk-in shower. Main floor laundry off the kitchen. Other features on the 1st level include a formal

  

  Toni Tindle

  Covered Bridge Realty

  (515) 824-5239

  1913 N 1st St, Winterset, IA 50273
• 

  

  /23

  $200,000 Sold Aug 01, 2025

  • 1,008 Sq Ft
  • $198/SF
  • 29 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1956

  324 W Filmore St, Winterset, IA 50273

  Adorable 2 bedroom 1.5 bath ranch on a corner lot. Nice size kitchen and living area. Updated LVP flooring on the main level, open floor plan and great lighting throughout the home. Spacious backyard, nice patio for entertainment, fenced in area for pets. Schedule your appointment today this won't last long!

  Sarah Cowman Homefront Real Estate, LLC

  324 W Filmore St, Winterset, IA 50273
• 

  

  /26

  Est $402,450 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  2647 Bittersweet Ave, Winterset, IA 50273

  2647 Bittersweet Ave, Winterset, IA 50273
• 

  

  /6

  $275,000

  • Land
  • 10 Acres
  • $26,882 per Acre

  2212 Deer Run Ave, Winterset, IA 50273

  Don't miss this rare opportunity to own 10 acres m/l of picturesque countryside just 8 miles west of Winterset, situated on a hard surface road and a prime corner lot. This walkout lot is ready for your dream home with rural water, electricity, and a driveway already added, saving you the time and expense of major improvements. The gently rolling terrain offers stunning views and the perfect

  

  Chris Kew

  RE/MAX Precision

  (515) 531-5829

  2212 Deer Run Ave, Winterset, IA 50273
• 

  

  /21

  $197,000 Sold Aug 01, 2025

  • 1,213 Sq Ft
  • $162/SF
  • 157 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1996

  723 N 6th Avenue Cir, Winterset, IA 50273

  Fresh Paint on main level and sellers are offering $4000 flooring allowance! Easy living in this 2 bed 2 and 1/2 bath townhome on a quiet cul de sac! You will love the open bright feel of this sweet home. The large living room has a gas fireplace and nice walk-in closet for coat storage There is a dining area by the patio doors that go out to a good sized deck. The kitchen has plenty of counter

  Sarah Cowman Homefront Real Estate, LLC

  723 N 6th Avenue Cir, Winterset, IA 50273
• 

  

  /35

  Est $554,258 Not Listed For Sale

  • 3 Beds
  • 2 Baths

  2395 148th St, Winterset, IA 50273

  2395 148th St, Winterset, IA 50273
• 

  

  /35

  $313,500

  • 3 Beds
  • 2 Baths
  • 1,513 Sq Ft

  1220 W Court Ave, Winterset, IA 50273

  Instantly appealing 1 1/2 story family home on Winterset W side with attached 2 car garage. There is a large level 70x157 lot w/a fenced backyard & shed. Front entrance leads to a cheerful living room with wide staircase to the upper floor. The bright southern facing kitchen has newer appliances & a pantry. The kitchen is open to a formal dining room with hardwood floors & gas fireplace as a

  

  Toni Tindle

  Covered Bridge Realty

  (515) 498-5106

  1220 W Court Ave, Winterset, IA 50273
• 

  

  /6

  $100,000 Sold Aug 01, 2025

  • Land
  • 5 Acres
  • $18,797 per Acre

  • 269 Days On Market

  Lot 1 114th Ct, Winterset, IA 50273

  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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

  Julie Baudler RE/MAX Concepts

  Lot 1 114th Ct, Winterset, IA 50273
• 

  

  /33

  Est $374,512 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  906 N 14th Ave, Winterset, IA 50273

  906 N 14th Ave, Winterset, IA 50273
• 

  

  /33

  $239,900 Pending

  • 3 Beds
  • 1 Bath
  • 942 Sq Ft

  1755 280th St, Winterset, IA 50273

  Three-bedroom 1 bath acreage home on 2.5 acres more or less. Home has had complete remodel with new sheetrock and insulation. Newer roof and AC with new duct work. Newer laminate flooring throughout within last two years. Replaced all fixtures cabinets sinks and more. Added extras include all appliances. 16x20 detached garage with 8 ft by 16 ft lean-to in rear. Included animal pens outside the

  

  Toni Tindle

  Covered Bridge Realty

  (515) 690-7594

  1755 280th St, Winterset, IA 50273
• 

  

  /26

  $335,000 Sold Jul 28, 2025

  • 1,497 Sq Ft
  • $224/SF
  • 88 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1999

  115 W North St, Winterset, IA 50273

  Really nice ranch home with covered front porch and just a few blocks north of the Winterset Square! This well kept home boasts an open floor plan with nice sized living room which includes gas fireplace and vaulted ceiling. The dining area overlooks the back yard. The kitchen has a nice eat at bar. The bedroom off of the living area has beautiful french doors and could also be used as an office.

  Sarah Cowman Homefront Real Estate, LLC

  115 W North St, Winterset, IA 50273
• 

  

  /23

  Est $343,716 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,273 Sq Ft

  807 N 15th Ave, Winterset, IA 50273

  807 N 15th Ave, Winterset, IA 50273
• 

  

  /132

  $2,931,000

  • Land
  • 400 Acres
  • $7,328 per Acre

  2169 Adair Madison Ave, Winterset, IA 50273

  Welcome to a truly exceptional and one-of-a-kind property offering the very best of Iowa’s scenic countryside. Situated just a few miles west of Winterset, this breathtaking 400 +/- acre farm presents a rare opportunity to own a perfect blend of income-producing land and world-class hunting.This property features approximately120 +/- acres of tiled and terraced cropland, currently under

  Sean Stewart Midwest Land Group

  2169 Adair Madison Ave, Winterset, IA 50273
• 

  

  /35

  $365,000 Sold Jul 28, 2025

  • 1,031 Sq Ft
  • $354/SF
  • 109 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1890

  2981 214th Trail, Winterset, IA 50273

  Spectacular 3.7 acres of rolling hills, trees, a pond, chicken coop and a barn for the picture perfect country lifestyle. This 1000+ sq ft 2 BR, 2 BA home has a gorgeous, updated kitchen worthy of Joanna Gaines, with gray and white cabinetry, a huge quartz topped center island, updated stainless steel appliances and two walk-in pantries with sliding barn doors. The dining area is large enough for

  Connie Brown Iowa Realty Ankeny

  2981 214th Trail, Winterset, IA 50273
• 

  

  /35

  Est $382,936 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 1,504 Sq Ft

  905 N 15th Ave, Winterset, IA 50273

  905 N 15th Ave, Winterset, IA 50273
• 

  /2

  $655,384

  • Land
  • 51 Acres
  • $12,975 per Acre

  0 Millstream Ct Unit 24336276, Winterset, IA 50273

  Premium Row Crop Ground with Endless Potential | Madison County, IowaPeoples Company is proud to represent 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

  Andrew Zellmer

  0 Millstream Ct Unit 24336276, Winterset, IA 50273
• 

  

  /23

  $255,000 Sold Jul 25, 2025

  • 1,438 Sq Ft
  • $177/SF
  • 42 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  322 N 15th Ave, Winterset, IA 50273

  Enjoy some of the best sunsets in Winterset at this 3 bed 2.5 bath home. Walk into the airy living room with gas fireplace and vaulted ceilings. The living room opens up to the spacious dining area and into the kitchen. There are lots of cabinets and counter top space as well as a center island! All of the kitchen appliances are newer and are included. Down the hall you will find a 1/2 bathroom

  Sarah Cowman Homefront Real Estate, LLC

  322 N 15th Ave, Winterset, IA 50273
• 

  

  /29

  Est $428,452 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,145 Sq Ft

  818 N 9th Ave, Winterset, IA 50273

  818 N 9th Ave, Winterset, IA 50273
• 

  /2

  $1,150,000

  • Land
  • 96 Acres
  • $11,965 per Acre

  0 Clark Tower Rd, Winterset, IA 50273

  Prime Rural Residential Developmental Land Offering | Just south of Winterset, IowaPeoples Company is proud to represent the Utsler Family Trust in the sale of an exceptional 96.11-acre m/l property located just 3 miles south of Winterset, Iowa, with paved access from Clark Tower Road. This offering represents a rare opportunity to acquire a tract of land already zoned Rural Residentialan

  Andrew Zellmer

  0 Clark Tower Rd, Winterset, IA 50273
• 

  

  /33

  $500,000 Sold Jul 23, 2025

  • 1,842 Sq Ft
  • $271/SF
  • 109 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2022

  2325 Carver Rd, Winterset, IA 50273

  Discover country living just south of historic Winterset in the heart of beautiful Madison County! Built in 2023, this barndominium blends contemporary style with durability, featuring concrete walls, a metal roof and siding, and polished concrete floors throughout. The open floor plan offers a seamless flow between living spaces, while in-floor heating ensures comfort during those winter months.

  Kyle Kuhns RE/MAX Revolution

  2325 Carver Rd, Winterset, IA 50273
• 

  

  /35

  Est $501,698 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,692 Sq Ft

  909 N 9th Ave, Winterset, IA 50273

  909 N 9th Ave, Winterset, IA 50273
• 

  

  /34

  $308,900

  • 3 Beds
  • 4 Baths
  • 1,694 Sq Ft

  604 W Jefferson St, Winterset, IA 50273

  This Gorgeous historical home is waiting for you on one of the prettiest streets in Winterset! This 3 bed, 2 full bath, 2 half bath has updates galore! The wrap around front porch welcomes you to the main floor and spacious living area and dining room with coffee bar. The back deck access gives you plenty of space to enjoy your morning coffee right off the kitchen with a powder room for your

  Rene Soldwisch Zealty Home Advisors

  604 W Jefferson St, Winterset, IA 50273
• 

  

  /12

  $269,900 Sold Jul 17, 2025

  • 1,388 Sq Ft
  • $194/SF
  • 12 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1995

  1310 W Jefferson St, Winterset, IA 50273

  Come take a look at this 4-bedroom, 2.5-bath home that has space for everyone! You'll love the open feel and flow throughout, and the finished lower level gives you that extra hangout or hobby space you've been needing. Step into the 4 seasons room, perfect for cozy mornings or relaxing evenings, and enjoy the view of the large, fenced-in backyard. It's ideal for gatherings, playtime, or just

  Jacob Ham Smart Avenue

  1310 W Jefferson St, Winterset, IA 50273
• 

  

  /17

  Est $292,380 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,344 Sq Ft

  809 W Mills St, Winterset, IA 50273

  809 W Mills St, Winterset, IA 50273
• 

  

  /35

  $485,000

  • 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
• 

  

  /29

  $285,000 Sold Jul 16, 2025

  • 1,388 Sq Ft
  • $205/SF
  • 47 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2004

  311 W North St, Winterset, IA 50273

  You'll love this wonderful, single level home! Come take a peek at this immaculate home with three bedrooms and three bathrooms. No HOA in this one! You'll love hosting family dinners in the enormous kitchen with plenty of space for baking and entertaining. Primary bedroom has ensuite shower bath and grab bars if needed. Fully finished lower level also has large storage space for all of your

  Abbey Robertson Century 21 Signature

  311 W North St, Winterset, IA 50273
• 

  

  /25

  Est $215,219 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 1,213 Sq Ft

  821 W Fremont St, Winterset, IA 50273

  821 W Fremont St, Winterset, IA 50273
• 

  

  /35

  $310,000

  • 3 Beds
  • 2.5 Baths
  • 1,972 Sq Ft

  522 N 10th St, Winterset, IA 50273

  Double Lot Opportunity! So Much Potential!!Don't miss out on this spacious 3+ bedroom, 2-bathroom home situated on a desirable double corner lot! The flexible 4th room offers endless possibilities. perfect as a den, craft room, nursery, or even a small bedroom (yes, it has a closet!).Inside, you'll find gorgeous wall-to-wall hardwood floors, a bright eat-in kitchen, and a generous

  Kristen Stehli RE/MAX Precision

  522 N 10th St, Winterset, IA 50273

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