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
/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
/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

/21
Est $158,597 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
/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

/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
/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

/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
/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

/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

/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
/28
$225,000 Sold Jul 14, 2025
- 924 Sq Ft
- $244/SF
- 21 Days On Market
- 4 Beds
- 2 Baths
- Built 1976
705 W Benton St, Winterset, IA 50273

Welcome to this super cute split-level home nestled in a great neighborhood in historic Winterset, just 30 minutes from Des Moines! This well-maintained home offers 924 sq ft of living space above ground, plus an additional 650 sq ft of finished lower level—perfect for families or anyone needing a bit more room to spread out.With 4 bedrooms—2 on the main level and 2 more downstairs—and 2

Ian Sparks Homefront Real Estate, LLC

705 W Benton 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

/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
/24
$325,000 Sold Jul 11, 2025
- 1,568 Sq Ft
- $207/SF
- 21 Days On Market
- 3 Beds
- 2 Baths
- Built 2018
701 E Madison St, Winterset, IA 50273

3BR 2BA walk-out ranch style home. Entering the home through the double garage, you'll enter the mud room/laundry room. This home has a wonderful open floor plan: kitchen features a large 5 shelf walk-in pantry, stainless steel farm house/apron sink & stainless appliance package, an eat-in dining area, living room with recessed lighting round out the open area. Large master BR with an AMAZING

Sarah Cowman Homefront Real Estate, LLC

701 E Madison St, 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

/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
/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

/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

/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
/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

/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

/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
/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

/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
$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
/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

/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

/31
$315,000
- 4 Beds
- 1.5 Baths
- 1,880 Sq Ft
804 N 4th Ave, Winterset, IA 50273

Welcome to a truly extraordinary home where timeless craftsmanship, modern luxury, and stunningnatural beauty come together in perfect harmony. Rarely does a property offer such a unique blend of old-world artisan detail and contemporary design, all set against the backdrop of gardens so exquisite! From the moment you arrive, the lush landscaping captures your attention, showcasing a level of

Sarah Cowman Homefront Real Estate, LLC

804 N 4th Ave, 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

/8
Est $1,247,632 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
505 E Madison St, Winterset, IA 50273

505 E Madison St, Winterset, IA 50273

/35
$319,900
- 3 Beds
- 1 Bath
- 1,350 Sq Ft
2385 Holliwell Bridge Rd, Winterset, IA 50273

Welcome to your dream country escape! You’ll fall in love with the scenic backdrop and peaceful surroundings! Nestled on 3.17 acres, this beautifully updated 1.5 story home offers the peace and privacy of rural living with the convenience of being close to town. Inside, the home features several key updates including a new roof (March 2025), new water lines, a newer heating & cooling with a

Misty Darling BH&G Real Estate Innovations

2385 Holliwell Bridge 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

/23
Est $209,620 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,213 Sq Ft
911 N 6th Avenue Cir, Winterset, IA 50273

911 N 6th Avenue Cir, 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

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