Madison, IA Homes

/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
/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
/18
$297,500 Sold Aug 05, 2025
- 995 Sq Ft
- $299/SF
- 41 Days On Market
- Studio
- 2 Baths
- Built 1994
515 E North St, Winterset, IA 50273

Investor Alert! Super clean and well-maintained duplex investment property. Each unit has 2 bedrooms and 1 full bath. Large living room, spacious kitchen and dining area. Sliding door from the dining area leads to the backyard. The bedrooms have good size closets. 1st floor laundry. Ample storage space in the basement. 1 car attached garage. 515 E. North has a newer stove and water heater. 519

Jennifer Stover Madison County Realty

515 E North 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

/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
/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
/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

/23
Est $185,589 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

/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
/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

/12
Est $230,161 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

/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
/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

/33
Est $387,025 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

/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
/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

/23
Est $359,437 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

/15
$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
/12
$140,000 Sold Jul 29, 2025
- 912 Sq Ft
- $154/SF
- 278 Days On Market
- 2 Beds
- 1 Bath
- Built 1965
2331 Clark Tower Rd, Winterset, IA 50273

Affordable acreage alert! Great location, just 2 miles from Winterset on a paved county highway. With a little TLC this 2 bedroom, 1 bath, 912 sf ranch would make a great first time home. or weekend get away. Perfect for the avid fisherman with Middle River right out the back door. 1 car detached garage +utility shed with concrete floor. and plenty of room for a larger outbuilding. Natural

Randall Henry Madison County Realty

2331 Clark Tower Rd, Winterset, IA 50273

/35
Est $404,194 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
/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

/29
Est $417,519 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
/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

/35
Est $526,054 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
/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

/17
Est $294,439 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
/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

/25
Est $210,475 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
/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

/8
Est $1,287,870 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 newer roof, new water lines, a newer heating & cooling with a mini-split unit

Misty Darling BH&G Real Estate Innovations

2385 Holliwell Bridge Rd, 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 $224,603 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
/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

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