Madison, IA Homes

/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
$699,900
- 4 Beds
- 3.5 Baths
- 2,200 Sq Ft
1821 Millstream Ct, Winterset, IA 50273

Prepare to be taken back by this distinguished two-story residence, masterfully crafted and lavishly finished with beautiful living space. Setting on three breathtaking acres, every inch of this estate exudes luxury and warmth—from the inviting front porch to expansive decks, professionally designed landscaping, a cozy inviting firepit, and an astounding garage capacity for seven vehicles—yes,

Sarah Cowman Homefront Real Estate, LLC

1821 Millstream Ct, 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

/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

/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
/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

/22
Est $211,818 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,213 Sq Ft
722 N 6th Avenue Cir, Winterset, IA 50273

722 N 6th Avenue Cir, Winterset, IA 50273

/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
/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

/36
Est $768,660 Not Listed For Sale
- 4 Beds
- 3.5 Baths
2208 204th Ct, Winterset, IA 50273

2208 204th Ct, 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
/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

/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

/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
/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

/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

/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
$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

/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

/34
$350,000
- 5 Beds
- 2.5 Baths
- 2,968 Sq Ft
323 W Jefferson St, Winterset, IA 50273

Exquisite historic home in the heart of Winterset just blocks from the bustling downtown square. If you love a quality historic home, this one is for you! This Freestyle Queen Anne Victorian 2-story is sure to impress. The past 2 owners have taken exquisite care of this gem. You will love the original woodwork hard floors, leaded glass & character! A front porch greets you as you enter complete

Sarah Cowman Homefront Real Estate, LLC

323 W Jefferson St, 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

/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

/35
$345,900
- 3 Beds
- 2.5 Baths
- 2,436 Sq Ft
724 W Jefferson St, Winterset, IA 50273

Prepare to be impressed with the renovations done to bring this stately home back to it's orignal glory! Step up to the inviting front covered porch & through the original leaded glass door into the stunning entryway showcasing the gorgeous stairway & original woodwork. The orignal hardwood floors flow throughout the entry room, HUGE living room, and into the formal dining room. Off the living

Sarah Cowman Homefront Real Estate, LLC

724 W Jefferson 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 $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

/33
$340,000
- 4 Beds
- 2.5 Baths
- 2,026 Sq Ft
708 W Fremont St, Winterset, IA 50273

Tons of room to spread out in this 4 bed 3 bath home. Walk into the gathering room that has many uses. It could be a formal dining room or a great sitting area. The spacious kitchen has plenty of cabinets and counter tops space and all appliances are included. The dining area can accommodate a large table. There is a huge mudroom off the kitchen as well as a 3/4 bath. The living room is huge

Sarah Cowman Homefront Real Estate, LLC

708 W Fremont 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 $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

/2
$384,500
- 3 Beds
- 2 Baths
- 1,400 Sq Ft
304 Maple Pointe, Winterset, IA 50273

Stryker Ranch with over-sized 3 car garage. Front porch with 2 stone base posts. 9'ceilings throughout main floor. Open stairs to basement. Granite or quartz counter tops in baths and kitchen. Kitchen boasts of a large walk-in pantry and stainless-steel appliances. White cabinets throughout. Luxury vinyl flooring. Gas fireplace. Master bath with raised vanity and elongated stool. High-efficiency

Robert D. Weeks Iowa Realty Waukee

304 Maple Pointe, Winterset, IA 50273
/12
$1,300,000 Sold Jul 17, 2025
- Land
- 172 Acres
- $7,554 per Acre
- 41 Days On Market
RR Millstream Ave, Winterset, IA 50273

If you are looking for a great investment opportunity or to add on to your current operation, take a look at this farm, 172.10 acres, with 140.41 acres currently enrolled in CRP through 2031 and a good return of $32,506.00. The balance of the farm is timbered draws which makes excellent habitat for pheasant, quail and white tail deer. Checkout the attached photos. There would be several nice

Larry Corkrean Madison County Realty

RR Millstream Ave, 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

/35
$310,000 Pending
- 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
/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 $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

/34
$308,900 Pending
- 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
/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

/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

/19
$298,000 Pending
- 4 Beds
- 2.5 Baths
- 2,696 Sq Ft
103 W Lane St, Winterset, IA 50273

Spacious 4-Bedroom Home on a Corner Lot!Welcome to this beautifully maintained 4-bedroom, 3-bath home offering 2,696 sq ft of versatile living space. Situated on a desirable corner lot, this property features a formal dining room, two spacious family rooms, and hardwood floors throughout.Upstairs, the oversized primary suite offers a flexible bonus area with a large closet. All three

Amanda Poganski Boutique Real Estate

103 W Lane 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

/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

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