Madison, IA Homes

/27
Est $246,028 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,452 Sq Ft
1215 W Washington St, Winterset, IA 50273

1215 W Washington St, Winterset, IA 50273

/35
$675,000
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
2283 Clark Tower Rd, Winterset, IA 50273

Discover this stunning newly built ICF (Insulated Concrete Form) berm home, showcasing executive-level finishes and exceptional energy efficiency. Nestled on just over 4 picturesque acres with scenic views of the iconic Clark Tower and Middle River Valley, this property offers both privacy and convenience. Ideally located on pavement for easy access. Enjoy ample space with several versatile

Marcus Sereg Iowa Realty South

2283 Clark Tower Rd, 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

/21
Est $265,697 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,404 Sq Ft
926 N 3rd Ave, Winterset, IA 50273

926 N 3rd Ave, Winterset, IA 50273

/34
$250,000
- 4 Beds
- 2 Baths
- 1,451 Sq Ft
520 W Benton St, Winterset, IA 50273

Charming 1.5 Story Home with Space for Everyone! This adorable 4-bedroom, 2-bath home offers a versatile layout perfect for families or anyone looking for room to grow. Enjoy a spacious main floor living room and two main-level bedrooms with hardwood floors hidden beneath the carpet—ready to be revealed if you love that classic touch. The eat-in kitchen features ample counter space, ideal for

Misty Darling BH&G Real Estate Innovations

520 W Benton 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

/34
Est $560,368 Not Listed For Sale
- 4 Beds
- 4.5 Baths
1145 W Summit St, Winterset, IA 50273

1145 W Summit St, Winterset, IA 50273

/4
$74,500
- Land
- 3.00 Acres
- $24,833 per Acre
1796 Millstream Ct, Winterset, IA 50273

Beautiful 3-acre lot located in the desirable Covered Bridge Estates! This scenic property offers the perfect blend of country feel with community convenience. Ideal for building your dream home with room to spread out—bring your own builder! Enjoy paved roads, rural water access at the road, and peaceful surroundings in this established neighborhood. Just minutes from town, with easy access to

Rachel Eller Summerset Realty

1796 Millstream Ct, 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

/33
Est $361,426 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 2,102 Sq Ft
1169 W Summit St, Winterset, IA 50273

1169 W Summit St, Winterset, IA 50273

/35
$850,000
- 3 Beds
- 3.5 Baths
- 3,298 Sq Ft
2218 N John Wayne Dr, Winterset, IA 50273

Welcome to this exceptional 3300 sq ft 3/4-bedroom, 4-bath brick ranch that perfectly balances privacy, convenience, and expansive living. Situated on private acreage within city limits but just outside of town, this property offers the best of both worlds—peaceful seclusion with quick access to amenities and major highways.From the moment you step through the grand entry, you'll appreciate

Alyssa Tadlock Madison County Realty

2218 N John Wayne Dr, 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

/28
Est $295,749 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,311 Sq Ft
907 W Washington St, Winterset, IA 50273

907 W Washington St, 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
/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

/25
Est $487,552 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,595 Sq Ft
614 W Benton St, Winterset, IA 50273

614 W Benton St, Winterset, IA 50273

/29
$219,900
- 3 Beds
- 2 Baths
- 1,452 Sq Ft
66 E High St, Winterset, IA 50273

Charming and fully updated 1.5 story home on a large corner lot in historic Winterset--roughly 30 minutes from the Des Moines metro! This 3-bed, 2-bath home features a spacious living room and a wrap-around layout that flows seamlessly from the living area to the updated kitchen with newer stainless steel appliances, and into the dining space. Stylish LVP flooring throughout the main level adds

Cameron Campos RE/MAX Concepts

66 E High St, 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

/3
Est $130,015 Not Listed For Sale
1019 N 4th Ave, Winterset, IA 50273

1019 N 4th Ave, Winterset, IA 50273

/35
$749,900
- 3 Beds
- 3 Baths
- 1,740 Sq Ft
1813 Maple Ct, Winterset, IA 50273

Welcome to your private escape in Covered Bridge Estates- where peaceful acreage, custom living, and endless opportunity meet.This rare offering includes two lots, totaling over 6.25 acres of scenic rural residential land just minutes from Winterset. Tucked into the heart of Madison County, this property features a custom-built 1,740 sq ft ranch with thoughtful upgrades throughout: a

Amy Lucht RE/MAX Precision

1813 Maple Ct, 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

/20
Est $230,408 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
501 W Buchanan St, Winterset, IA 50273

501 W Buchanan St, Winterset, IA 50273

/21
$180,000
- 3 Beds
- 1 Bath
- 1,222 Sq Ft
601 E Green St, Winterset, IA 50273

This beautifully updated 3-bedroom, 1-bath farmhouse at 601 E Green St offers 1,222 sq ft of thoughtfully designed living space. Full of character, the home features an eat-in kitchen, a cozy living room with plenty of natural light, and a bonus room that can easily serve as an office or an extra bedroom. The updated bathroom and fresh flooring throughout the main level add modern convenience.

Theodore Craig Developers Realty Group LLC

601 E Green St, 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

/22
Est $216,595 Not Listed For Sale
- 2 Beds
- 2 Baths
- 864 Sq Ft
618 N 4th Ave, Winterset, IA 50273

618 N 4th Ave, Winterset, IA 50273

/14
$240,000
- 3 Beds
- 1.5 Baths
- 912 Sq Ft
1021 W South St, Winterset, IA 50273

Come enjoy small town living in Winterset in this adorable 3 bedroom ranch home! The spacious living area has tons of natural light with the large windows and beautiful hardwood floors. Find three bedrooms and a full bath on the main floor, as well as the farmhouse style kitchen featuring white subway tile backsplash and white cabinets. The lower level features an extra living space, half bath,

Jenna Carney Keller Williams Realty GDM

1021 W South St, 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 $211,708 Not Listed For Sale
- 2 Beds
- 1 Bath
- 912 Sq Ft
1016 W South St, Winterset, IA 50273

1016 W South 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
$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

/21
Est $205,417 Not Listed For Sale
- 3 Beds
- 2 Baths
- 964 Sq Ft
110 N 10th Ave, Winterset, IA 50273

110 N 10th Ave, 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
/24
$218,000 Sold May 22, 2025
- 912 Sq Ft
- $239/SF
- 58 Days On Market
- 3 Beds
- 2 Baths
- Built 1961
1104 W South St, Winterset, IA 50273

Welcome to this delightful 3 bedroom, 2 bathroom ranch-style home. Nestled in a desirable neighborhood near schools and the aquatic center, this charming residence offers a fenced backyard perfect for pets & outdoor enjoyment. All appliances stay with the home, and recent upgrades include new electrical, air conditioning/furnace, siding, gutters, & roof. With its convenient location and cozy

Kenneth Kauzlarich RE/MAX Precision

1104 W South St, Winterset, IA 50273

/24
Est $245,081 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,260 Sq Ft
906 W Court Ave, Winterset, IA 50273

906 W Court Ave, Winterset, IA 50273

/25
$213,000
- 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
/20
$125,000 Sold May 20, 2025
- 1,255 Sq Ft
- $100/SF
- 4 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1896
728 W Green St, Winterset, IA 50273

Quaint 1.5 story home; well loved by its owner. 1255 sq feet of living space with 1 bedroom 1 bath down and 2 bedrooms 1/2 bath up. This home is loaded with charm. Large living room with wood floors surrounded by windows that compliment the era in which the home was built. Formal dining room with built in; great lighting from windows along with a nice sized kitchen. Cute little back porch and

Sarah Cowman Homefront Real Estate, LLC

728 W Green St, Winterset, IA 50273

/35
Est $264,112 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

/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
/26
$240,000 Sold May 20, 2025
- 2,016 Sq Ft
- $119/SF
- 173 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1900
401 E Jefferson St, Winterset, IA 50273

So much space in this 4 bedroom, 2.5 bath, 2016 sf home! This home has the perfect mix of old character and new amenities. New updates included recently remodeled kitchen, updated bathrooms, newer HVAC and roof. All the while, keeping the charm of the old with amazing staircase and trim throughout, hardwood floors, high ceilings, double staircase and hardwood floors. 1st floor bedroom with full

Jennifer Stover Madison County Realty

401 E Jefferson St, Winterset, IA 50273

/31
Est $215,865 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,264 Sq Ft
322 W South St, Winterset, IA 50273

322 W South St, Winterset, IA 50273

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