Madison, IA Homes

/31
$395,000 Sold Jun 16, 2025
- 1,518 Sq Ft
- $260/SF
- 67 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1996
2923 N John Wayne Dr, Winterset, IA 50273

Here is your chance to live on 3 acres right off of Hwy 169 in Madison County. Check out this updated ranch home featuring 4 bedrooms 3 baths. On the main level you have the Primary suite, with tons of closet space, 2nd bedroom or office. spacious living area with large picture windows, and a large deck off the dining room. On the finished lower level there are 2 additional bedrooms, 2nd family

Rachel Eller Summerset Realty

2923 N John Wayne Dr, Winterset, IA 50273

/35
Est $266,967 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 1,900 Sq Ft
704 N 4th Ave, Winterset, IA 50273

704 N 4th Ave, Winterset, IA 50273

/18
$73,000
- 2 Beds
- 1 Bath
- 792 Sq Ft
3028 Carver Rd, Winterset, IA 50273

Unique opportunity to own an affordable acreage!! NO Covenants!! 2bed/1 bath with bonus loft on +\- half acre in Madison County! 1+ car detached garage. Fenced area for optional livestock or garden.

Alyssa Tadlock Madison County Realty

3028 Carver Rd, Winterset, IA 50273
/35
$750,000 Sold Jun 13, 2025
- 1,534 Sq Ft
- $489/SF
- 5 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2005
2176 148th St, Winterset, IA 50273

This M/L 18 acres has something for everyone! You have the wildlife, timber, a pond for fishing, grass & alfalfa mix for your horses or to sell. A nice almost new 30 by 40 pole barn with 2 >10ft by 10ft doors, a concrete floor, electric and outside RV hookups. A detached 2 car garage, 2 sheds, ample parking for extra trailers and several fruit trees. The home has over 2600 sq foot of finished

Lisa Pierce Honer Summit Realty

2176 148th St, Winterset, IA 50273

/25
Est $191,102 Not Listed For Sale
- 2 Beds
- 1 Bath
- 984 Sq Ft
422 W Filmore St, Winterset, IA 50273

422 W Filmore St, Winterset, IA 50273

/31
$128,000
- 2 Beds
- 1 Bath
- 942 Sq Ft
59 E Washington St, Winterset, IA 50273

Great opportunity for an investor or a first-time buyer looking to make a place their own!! This 942 sq ft ranch-style home offers potential, and an opportunity to build equity with a little TLC. The main level features a spacious living room with built-ins, a generously sized bedroom with double closets, and an eat-in kitchen ready for your personal touch. Toward the back of the home, youll

John Brummett RE/MAX Precision

59 E Washington St, Winterset, IA 50273
/25
$213,865 Sold Jun 13, 2025
- 1,061 Sq Ft
- $202/SF
- 13 Days On Market
- 3 Beds
- 1 Bath
- Built 1910
707 E Buchanan St, Winterset, IA 50273

Fully remodeled 3 bedroom 1 bathroom 2 stall garage home in Winterset! Spacious living room with windows all around offering so much natural light! New kitchen!! New cabinets, new countertops, and new appliances in this kitchen offering plenty of cabinet and countertop space! All new appliances also included in this home! One bedroom on the main level, along with the full bathroom with laundry

Jenn Ho Goh GoSynergy Realty

707 E Buchanan St, Winterset, IA 50273

/24
Est $287,836 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,600 Sq Ft
604 W Filmore St, Winterset, IA 50273

604 W Filmore St, Winterset, IA 50273

/25
$212,000
- 3 Beds
- 2 Baths
- 1,524 Sq Ft
417 S 2nd St, Winterset, IA 50273

A must-see home in a fantastic location, just moments from the historic John Wayne birthplace and just blocks away from the bustling downtown square. Walk up to your “new “front porch that welcomes you with new columns, railings, and a porch swing that you'll never want to leave! Perfect spot for your morning coffee , reading your favorite book or lounging at the end of a long day. As you enter,

Sue Monroe Spire Real Estate

417 S 2nd St, Winterset, IA 50273
/21
$225,000 Sold Jun 11, 2025
- 960 Sq Ft
- $234/SF
- 107 Days On Market
- 3 Beds
- 1 Bath
- Built 1976
703 N 3rd Ave, Winterset, IA 50273

You will want to check out this well kept 3 bedroom home with finished basement on a corner lot. Home features 3 bedrooms and one bath on the main level. The kitchen is bright and nicely updated with newer appliances which are included! The dining area is adjacent to the kitchen which has a door that leads to the huge deck - perfect for grilling! The living room is very large with a big bright

Sarah Cowman Homefront Real Estate, LLC

703 N 3rd Ave, Winterset, IA 50273

/25
Est $209,137 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,816 Sq Ft
809 E Benton St, Winterset, IA 50273

809 E Benton St, Winterset, IA 50273

/10
$299,000
- Land
- 10 Acres
- $29,900 per Acre
TBD Iowa 92, Winterset, IA 50273

Build Your Dream Home on this Scenic 10-Acre Parcel!Located just off paved Highway 92 and only 25 minutes from the Des Moines metro, this beautiful ±10 acre lot offers the perfect mix of convenience and peaceful country living. With scenic views, open space, and rural water and electric at the road, it’s an ideal setting for your future home, hobby farm, or weekend retreat.Plenty of

Rachel Eller Summerset Realty

TBD Iowa 92, Winterset, IA 50273
/24
$280,000 Sold Jun 11, 2025
- 2,212 Sq Ft
- $127/SF
- 271 Days On Market
- 5 Beds
- 2 Baths
- Built 1930
217 E Jefferson St, Winterset, IA 50273

Seller offering $5000 worth of buyer’s concessions for closing costs or beautification to make home their own! Unique property; two homes 1 lot. Main home is 5 bedroom, 2 remodeled baths with new carpet and flooring throughout. Kitchen has been remodeled with new cabinets, new dishwasher w/warranty and new stove and refrigerator. New Washer and Dryer are also included! Other updates in the main

Sarah Cowman Homefront Real Estate, LLC

217 E Jefferson St, Winterset, IA 50273

/16
Est $247,279 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,296 Sq Ft
602 E Benton St, Winterset, IA 50273

602 E Benton St, Winterset, IA 50273

/22
$134,900
- 2 Beds
- 2 Baths
- 1,093 Sq Ft
103 S 3rd St, Winterset, IA 50273

Previously used as an up-and-down duplex, this property offers a flexible layout and a spacious open floor plan. The living room is generously sized. While the home does need some work, it presents a great opportunity for customization or investment. Additional features include an attached one-car garage for convenient parking or storage. Great location.

Zineta Imamovic Realty ONE Group Impact

103 S 3rd St, Winterset, IA 50273
/28
$260,000 Sold Jun 05, 2025
- 1,500 Sq Ft
- $173/SF
- 19 Days On Market
- 4 Beds
- 3 Baths
- Built 1964
421 W Buchanan St, Winterset, IA 50273

This charming and beautifully updated 2-story home in Winterset has everything you need and is perfect for entertaining indoors or out! The main level features a spacious living room, great size eat-in kitchen, and a convenient half bath. Upstairs, you'll find four large bedrooms?three with stunning hardwood floors and all with generous closet space, and a full bath. The finished basement

Stephanie Anania RE/MAX Revolution

421 W Buchanan St, Winterset, IA 50273

/20
Est $252,462 Not Listed For Sale
- 4 Beds
- 2 Baths
- 924 Sq Ft
802 E Benton St, Winterset, IA 50273

802 E Benton St, Winterset, IA 50273

/28
$550,000
- 4 Beds
- 3 Baths
- 1,728 Sq Ft
715 N John Wayne Dr, Winterset, IA 50273

Super unique investment opportunity! This property consists of a residential house and 4 rental units. The house is 1728 sf with 3 bedrooms, 2 bathrooms, 2 family rooms, 1st floor laundry, basement, 2 car garage. The lower level of the house also has 1 bedroom, bath, kitchen, fireplace. You could also rent out the LL of the house. Making total number of units available for rent: 6. The owners

Jennifer Stover Madison County Realty

715 N John Wayne Dr, Winterset, IA 50273
/29
$174,900 Sold Jun 03, 2025
- 784 Sq Ft
- $223/SF
- 18 Days On Market
- 2 Beds
- 1 Bath
- Built 1900
501 W Summit St, Winterset, IA 50273

This well-maintained two-bedroom ranch is the perfect place to call home! Conveniently located near schools, this home features a cozy living space, an efficient kitchen, and a full bath. Enjoy the ease of single-level living with the added bonus of a detached one-car garage, providing extra storage space. The spacious fenced in yard offers room to relax, garden, or entertain. Whether you're a

Rachel Eller Summerset Realty

501 W Summit St, Winterset, IA 50273

/24
Est $263,740 Not Listed For Sale
- 2 Beds
- 1 Bath
- 840 Sq Ft
317 E North St, Winterset, IA 50273

317 E North St, Winterset, IA 50273

/13
$159,900
- 5 Beds
- 2 Baths
- 1,556 Sq Ft
523 S 2nd St, Winterset, IA 50273

This conversion duplex offers the perfect opportunity to add value and generate strong returns. Located just blocks from downtown Winterset, this property is ideal for house hackers, investors, or anyone looking to expand their portfolio in a growing community. Each unit offers spacious layouts with room for updates and personalization. With separate entrances, utilities, and off-street parking

Ben Grotzke LPT Realty, LLC

523 S 2nd St, Winterset, IA 50273
/35
$549,000 Sold Jun 02, 2025
- 1,344 Sq Ft
- $408/SF
- 6 Days On Market
- 3 Beds
- 1 Bath
- Built 1910
2640 206th St, Winterset, IA 50273

Step right into your own magical country oasis compete with party barn, pond and amazing views! This sweet homestead has so much to offer! Located directly off of highway 92 - barely any gravel! The completely renovated 3 bedroom 1 bath home is bursting with character & has the most stunning southern views! Walk into the cozy living room with tons of natural light & enjoy the ambiance of the

Sarah Cowman Homefront Real Estate, LLC

2640 206th St, Winterset, IA 50273

/20
Est $230,876 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,252 Sq Ft
506 E Filmore St, Winterset, IA 50273

506 E Filmore St, Winterset, IA 50273

/33
$664,999
- 4 Beds
- 3 Baths
- 1,895 Sq Ft
1634 170th St, Winterset, IA 50273

Scenic Winterset Acreage – Earlham Schools - Ranch Home on 11+ Acres with Walkout Basement & Hobby Farm Features!Discover your dream homestead just minutes from Winterset! This beautifully maintained ranch-style home sits on 11.2 acres of rolling countryside and offers 4 bedrooms, 3 full bathrooms, and a fully finished walkout basement.Step into the heart of the home — a chef’s

Kate Carlson Realty ONE Group Impact

1634 170th St, Winterset, IA 50273
/28
$294,000 Sold Jun 02, 2025
- 1,464 Sq Ft
- $201/SF
- 6 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1992
1210 W Jefferson St, Winterset, IA 50273

Move in ready Winterset Home blocks from the Historic Square & across the street from the city pool, park, tennis & Pickleball courts! With over 1,900 sq ft finish, this 3 BR (4th non-conforming) 2.5 BA home has all the updates to make this a peace of mind investment. Updates by the current seller include new roof, garage door, carpet throughout, garage epoxy & radon mitigation system. Updates

Ou Meksay RE/MAX Concepts

1210 W Jefferson St, Winterset, IA 50273

/18
Est $227,164 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,248 Sq Ft
510 E Filmore St, Winterset, IA 50273

510 E Filmore St, Winterset, IA 50273

/12
$199,900
- Land
- 4.68 Acres
- $42,714 per Acre
2215 245 Ln, Winterset, IA 50273

Beautiful rolling building lot just south of town and on minimal gravel located on a dead end road! This 4.68 acre m/l lot is ready for you to bring your builder and build your dream home! The lot gently rolls to the north for a walk out opportunity and overlooks the neighbor's pristine pond! There will be very minimal covenants (currenty being drawn up by attorney) and the county needs to

Sarah Cowman Homefront Real Estate, LLC

2215 245 Ln, Winterset, IA 50273
/35
$314,900 Sold Jun 02, 2025
- 1,278 Sq Ft
- $246/SF
- 91 Days On Market
- 3 Beds
- 3 Baths
- Built 2020
602 W Stone St, Winterset, IA 50273

Welcome to 602 W Stone St – a stunning corner unit bi-attached ranch townhome in the heart of historic Winterset! This beautifully maintained, turn-key property offers nearly 2,400 sq. ft. of finished living space with 3 bedrooms, 3 bathrooms, and a 2-car attached garage. Step into the stylish kitchen featuring painted maple cabinets, white quartz countertops, and abundant storage—ideal for both

Ryan Rohlf Keller Williams Legacy Group

602 W Stone St, Winterset, IA 50273

/20
Est $188,008 Not Listed For Sale
- 2 Beds
- 1 Bath
- 986 Sq Ft
306 E Buchanan St, Winterset, IA 50273

306 E Buchanan St, Winterset, IA 50273

/34
$293,000
- 3 Beds
- 2 Baths
- 1,741 Sq Ft
620 W Filmore St, Winterset, IA 50273

Charming Ranch with Modern Updates on a Quiet StreetWelcome to this beautifully updated home nestled on a peaceful street, perfect for those seeking both comfort and convenience. Step onto the quaint front porch and into a home that blends cozy charm with modern finishes throughout.This spacious home features a large primary bedroom with an attached bathroom, plus two additional

Alyssa Tadlock Madison County Realty

620 W Filmore St, Winterset, IA 50273
/21
$60,000 Sold May 30, 2025
- 1,174 Sq Ft
- $51/SF
- 9 Days On Market
- 3 Beds
- 1 Bath
- Built 1904
110 E Grade St, Winterset, IA 50273

3 BR 1 bath one story frame home in Winterset. It has a large kitchen with entrance to basement from inside the home. Rear yard with front and back decks. Home is being sold "AS IS". Some upgrades within the last ten years to mechanicals and exterior features. Hardwood floors in many areas. Bonus room off SW corner of the home. Priced below assessed value. Come to view.

Toni Tindle Covered Bridge Realty

110 E Grade St, Winterset, IA 50273

/15
Est $221,662 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,008 Sq Ft
423 E Benton St, Winterset, IA 50273

423 E Benton St, Winterset, IA 50273

/22
$440,000
- 3 Beds
- 2 Baths
- 1,650 Sq Ft
2369 Saint Charles Rd, Winterset, IA 50273

MADISON COUNTY ACREAGE! Beautiful ZERO ENTRY home, that was built with CONCRETE WALLS, on 10+- wooded acres. The beauty of the country, but on a paved road, close to Winterset and a 30-minute commute to West Des Moines. This home has a large kitchen with HICKORY CABINETS and plenty of counter space. You will love all of the big windows and French doors, bringing in so much natural light. The OPEN

Betsy Breeding Realty ONE Group Impact

2369 Saint Charles Rd, Winterset, IA 50273
/14
$121,000 Sold May 30, 2025
- 664 Sq Ft
- $182/SF
- 147 Days On Market
- 2 Beds
- 1 Bath
- Built 1880
603 W Hutchings St, Winterset, IA 50273

Charming and updated home nestled in a quiet, small-town neighborhood. This cozy residence features modern finishes, a spacious master bedroom and a functional layout perfect for comfortable living. Enjoy a modern renovated kitchen, updated flooring, and well-maintained systems throughout. The backyard offers a great space for relaxation or entertaining. With its affordable price and convenient

Anthony Dennis RE/MAX Revolution

603 W Hutchings St, Winterset, IA 50273

/19
Est $211,175 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
715 N 5th St, Winterset, IA 50273

715 N 5th St, Winterset, IA 50273

/32
$499,900
- 6 Beds
- 3.5 Baths
- 2,351 Sq Ft
301 Magnolia Point, Winterset, IA 50273

Spacious and beautifully maintained 6-bedroom, 3.5-bath home situated on a generous 0.65-acre lot! Built in 2020, this home offers the perfect blend of modern style and functional living. The open-concept main level features a bright kitchen with ample storage and a cozy living area. The walk-out basement provides even more living space—ideal for entertaining, a home gym, or rec area. Enjoy the

Rachel Eller Summerset Realty

301 Magnolia Point, Winterset, IA 50273
/31
$305,000 Sold May 28, 2025
- 1,904 Sq Ft
- $160/SF
- 7 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1967
602 W Hutchings St, Winterset, IA 50273

Absolutely stunning ranch on a large corner lot in the heart of Winterset! Plenty of space with over 2600 of finished living space! 3 bedrooms on the main level with 2 bathrooms, eat in kitchen with TONS of storage, beautiful hardwood floors leading into the extra living room/dining area. You will LOVE the family room with stone fireplace with plenty of room to entertain! Partially finished

Susan Sheldahl Realty One Group Impact

602 W Hutchings St, Winterset, IA 50273

/25
Est $264,333 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,092 Sq Ft
508 E Lane St, Winterset, IA 50273

508 E Lane St, Winterset, IA 50273

/27
$195,000
- Land
- 10 Acres
- $18,786 per Acre
TBD Carver Rd, Winterset, IA 50273

Picturesque 10 acre building site w many miles of valley views to build your dream home or multiple cabin retreat. Multiple building locations and driveways are possible on this property. Enjoy complete privacy, abundant natural beauty, and endless possibilities for creating your ideal retreat. Enjoy private the existing trails through the land just a few minutes south of Winterset and a half

Lindsay Range EXIT Realty & Associates

TBD Carver Rd, Winterset, IA 50273
/23
$190,000 Sold May 23, 2025
- 992 Sq Ft
- $192/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1947
323 E Jefferson St, Winterset, IA 50273

Charming Brick Bungalow Full of Character on a Prime Corner Lot! Step into timeless charm with this beautifully maintained brick bungalow just a short walk from the town square. Bursting with original character, this home features gorgeous hardwood floors, elegant crystal door knobs, and classic built-ins that tell a story of craftsmanship and care. The main floor offers two comfortable bedrooms

Deanna Roth Century 21 Signature

323 E Jefferson St, Winterset, IA 50273

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