Houses for Sale in 50273

/35
$226,900
- 3 Beds
- 1.5 Baths
- 958 Sq Ft
513 W Hutchings St, Winterset, IA 50273

Step into this beautifully remodeled 2025 home complete with 3 bedrooms and 1.5 bathrooms. Thoughtfully updated throughout, this residence includes new sheet rock and fresh paint, new LVP flooring, new central air system and duct work, upgraded plumbing and electrical and all new windows. Lage kitchen features custom Amish-built cabinetry, quartz countertops and just around the corner a main

Toni Tindle

Covered Bridge Realty

(515) 481-5094

513 W Hutchings 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
/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
/35
$450,000
- 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 proudly on nearly 1 acre. Kitchen has had a complete remodel including adding a convenient island & farm sink. Master/BR on 1st floor has large walk-in closet, & 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
$360,000
- 5 Beds
- 4 Baths
- 2,110 Sq Ft
309 N 15th Ave, Winterset, IA 50273

Don’t miss your chance to own this beautifully appointed 2-story home tucked away on a quiet street. From the moment you arrive, the inviting front porch sets the tone—perfect for sipping your morning coffee or unwinding with a sunset view. Step inside to an open-concept layout designed for gathering, with seamless flow from the spacious living areas to the patio, ideal for evening

Sarah Cowman Homefront Real Estate, LLC

309 N 15th Ave, Winterset, IA 50273
/30
$499,900
- 4 Beds
- 3 Baths
- 1,540 Sq Ft
400 N 14th Ave, Winterset, IA 50273

This immaculate 4-bedroom, 2-bath ranch home perfectly blends modern comfort with timeless style. Built in 2013 and exceptionally cared for, every detail radiates warmth, quality, and convenience. Step inside to an inviting open layout highlighted floor-to-ceiling stone fireplace—a stunning centerpiece for cozy evenings or lively gatherings with family and friends. The beautiful kitchen is both

Sarah Cowman Homefront Real Estate, LLC

400 N 14th Ave, Winterset, IA 50273
/35
$639,900
- 5 Beds
- 3.5 Baths
- 2,229 Sq Ft
1795 Millstream Ct, Unincorporated, IA 50273

This stunning 1.5-story home sits on just over 3 acres of paved countryside 3miles north of Winterset & only 20 minutes from West Des Moines. With 5 bedrooms plus an exerciseroom, 4 bathrooms, and more than 3,200 sq. ft. of finished living space, this property combines comfort,style, and convenience. Step inside to find a soaring 2-story vaulted great room with a fireplace. The

Jenny Wille Iowa Realty Mills Crossing

1795 Millstream Ct, Unincorporated, IA 50273
/24
$614,000
- 5 Beds
- 2 Baths
- 2,074 Sq Ft
2283 Pioneer Ave, Winterset, IA 50273

Escape to the serenity of this stunning story-and-a-half home nestled on 20 acres of timber, open land, and a flowing creek. Built in 1997 and tastefully remodeled in 2018, this 5-bedroom, 2-bath home offers the perfect blend of comfort, functionality, and natural beauty. Step inside to discover custom hickory cabinets in the kitchen with stainless steel appliances, cozy living spaces, and warm

Bryan Curtis Attain RE

2283 Pioneer Ave, Winterset, IA 50273
/25
$389,900
- 4 Beds
- 2.5 Baths
- 1,333 Sq Ft
215 W Buchanan St, Winterset, IA 50273

Completely Renovated Winterset Gem!This 4-bedroom, 3-bath home (1,333 sq ft above grade + 409 finished basement) is in the heart of Winterset—steps from parks, schools, and the historic town square. Enjoy all Winterset has to offer, including the John Wayne Birthplace & Museum, the famous Covered Bridges of Madison County, and year-round festivals.Fully renovated from top to

Elizabeth Gordon Realty ONE Group Impact

215 W Buchanan St, Winterset, IA 50273
/31
$319,000
- 4 Beds
- 2 Baths
- 1,792 Sq Ft
516 S 8th Ave, Winterset, IA 50273

Step into history without the hassle! Built in 1890 and recently renovated, this 4-bedroom, 2-bath home offers the character you love with the updates you need. Sunlight pours through abundant windows, filling the spacious layout and large kitchen. Situated on nearly a half-acre (.418) lot right in town, you’ll have plenty of room to spread out, just minutes from Main Street and the birthplace of

Tiffany Marcum The American Real Estate Co.

516 S 8th Ave, Winterset, IA 50273
/34
$650,000
- 3 Beds
- 2.5 Baths
- 2,432 Sq Ft
719 E Washington St, Winterset, IA 50273

If the "Wow Factor" is what you are hoping for in a home, this one is a must-see! This home was gutted down to the studs and completely rebuilt, so it is just like brand new! Walk in the front door, and you will love all the natural light as you enter the living room with a cozy gas fireplace. The large dining area adjoins the gorgeous kitchen with tons of cabinets and countertop space. There is

Sarah Cowman Homefront Real Estate, LLC

719 E Washington St, Winterset, IA 50273
/35
$375,000
- 4 Beds
- 2 Baths
- 2,724 Sq Ft
615 N 1st Ave, Winterset, IA 50273

This beautifully remodeled residence combines timeless charm with modern comfort. Step inside to discover hardwood floors and a striking, gracefully designed staircase that sets the tone for the entire home. The inviting front porch offers the perfect spot to welcome guests or enjoy peaceful evenings outdoors. Featuring four generously sized bedrooms plus a bonus room, and a full bath on each

Sarah Cowman Homefront Real Estate, LLC

615 N 1st Ave, Winterset, IA 50273
/26
$404,900
- 4 Beds
- 3.5 Baths
- 1,710 Sq Ft
1011 N 14th Ave, Winterset, IA 50273

Discover your own slice of heaven right in town! This inviting two-story home is set in a friendly neighborhood where there's plenty of room to play and grow. The thoughtful layout makes the most of every square foot, creating spaces that work well for everyday life.The main level welcomes you with a handy drop zone, half bath, and a office with French doors. The open kitchen and family room

Michelle Hanson RE/MAX Concepts

1011 N 14th Ave, Winterset, IA 50273
/35
$335,000
- 4 Beds
- 2 Baths
- 1,912 Sq Ft
59 E Benton St, Winterset, IA 50273

Step inside this well-loved home that blends timeless character with modern updates—ready for its next owner to make it their own. The home’s original woodwork, in excellent condition, adds warmth and charm throughout. Enjoy relaxing mornings with coffee or peaceful evenings with dinner on the inviting front porch. Inside, you’ll find a spacious living room that flows seamlessly into a formal

Sarah Cowman Homefront Real Estate, LLC

59 E Benton St, Winterset, IA 50273
/35
$475,000
- 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
/35
$375,000
- 2 Beds
- 3 Baths
- 1,531 Sq Ft
701 North St, Patterson, IA 50218

Rare In-Town Acreage with Pole Barn – Just Minutes from WDSM & Winterset! This unique property offers the best of both worlds—peaceful acreage living with quick access to West Des Moines (15 mins) and Winterset (5 mins). Located on the edge of town, this well-maintained acreage sits on two separate parcels, offering flexibility for personal use, rental income, or resale. The spacious 48’x80’x12’

Becky Knight Iowa Realty Mills Crossing

701 North St, Patterson, IA 50218
/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
/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
/35
$330,000
- 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
/29
$275,000
- 1 Bed
- 1 Bath
- 800 Sq Ft
2089 270th St, Winterset, IA 50273

Tucked away just off Highway 169 with minimal gravel, this rare 5+ acre property offers the perfect mix of seclusion, functionality, and future potential. The centerpiece is a recently finished 1-bedroom barndominium, where modern living quarters are seamlessly connected to a fully insulated shop--ideal for hobbyists, mechanics, or anyone needing flexible workspace right at home. Surrounded by

Dan Rozga RE/MAX Concepts

2089 270th St, Winterset, IA 50273
/19
$260,000
- 4 Beds
- 2 Baths
- 1,270 Sq Ft
1413 W Washington St, Winterset, IA 50273

Move-in ready and beautifully maintained, this 4-bedroom ranch offers easy single-level living with an inviting open floor plan. A rare oversized 3-car garage with additional storage is a dream for car enthusiasts or hobbyists, and the deck off the kitchen provides the perfect backdrop for outdoor dining and entertaining!

Sarah Cowman Homefront Real Estate, LLC

1413 W Washington St, Winterset, IA 50273
/23
$274,900
- 3 Beds
- 2 Baths
- 1,725 Sq Ft
303 E Court Ave, Winterset, IA 50273

Welcome to one of the charming historical homes in Winterset. Walking through the front entrance, visitors are greeted with natural light spilling across the hardwood floors. As they enter the kitchen, the openness is easily noticeable making it a perfect place to host or have family dinners. The living room has charming built-ins which adds to the cozy feel. The laundry area is located on the

Tamra Yeager Pro Team Realty

303 E Court Ave, Winterset, IA 50273
/25
$299,000
- 3 Beds
- 2 Baths
- 1,252 Sq Ft
722 W Mills St, Winterset, IA 50273

Beautifully maintained 3-bedroom, 2-bath ranch showcasing an inviting open floor plan with dining area. The partially finished basement includes a comfortable family room with an egress window, perfect for entertaining or relaxing. Step outside to a private, fenced backyard featuring a charming deck that offers a peaceful view of the yard—ideal for gatherings or quiet evenings at home.

Sarah Cowman Homefront Real Estate, LLC

722 W Mills St, Winterset, IA 50273
/23
$159,900
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
516 W Summit St, Winterset, IA 50273

Are you looking for a house with a LARGE YARD, close to SCHOOLS and WINTERSET TOWN SQUARE.Come take a look at this well-maintained ranch, on a big lot, in the beautiful town of Winterset! The three nice sized bedrooms also have great closet space. You will also like the open kitchen/dining area, with plenty of natural light, that leads out to the NEW LARGE DECK, perfect for morning coffee and

Betsy Breeding Realty ONE Group Impact

516 W Summit St, Winterset, IA 50273
/27
$210,000
- 2 Beds
- 2 Baths
- 1,050 Sq Ft
202 S 7th Ave, Winterset, IA 50273

Full of character and charm, this home sits on a desirable corner lot in the heart of Winterset Step inside to bright living spaces with new flooring throughout. The functional kitchen features ample storage and prep space and opens to the dining room. An inviting 3 season room steps from the living room and adjoined to the garage offers the perfect bonus space for entertaining or quiet mornings.

Tiffany Ehler Boutique Real Estate

202 S 7th Ave, Winterset, IA 50273
/23
$309,900
- 3 Beds
- 1.5 Baths
- 2,130 Sq Ft
721 W Court Ave, Winterset, IA 50273

Don't miss the opportunity to own this home on historical Court Avenue! You will love sitting on the wraparound porch for your morning coffee or just some time to relax. Upon entering the home, you will be impressed with the beautiful details of the open staircase. The first floor has a large living, family and dining rooms, 1/2 bath and kitchen. The hardwood floors and the woodwork are original

Larry Corkrean Madison County Realty

721 W Court Ave, Winterset, IA 50273
/27
$247,900
- 3 Beds
- 2 Baths
- 1,106 Sq Ft
316 E Jefferson St, Winterset, IA 50273

Charming Victorian that has been fully renovated. The living room has ten-foot ceilings, beautiful chandeliers, and a gas fireplace. In the main bedroom, there is a unique stained glass window. Walking into the kitchen, you are greeted with quartz countertops and custom cabinets, which adds a modern touch. All the appliances are 2-3 years old. Washer/dryer hookups are in the basement along with a

Tamra Yeager Pro Team Realty

316 E Jefferson St, Winterset, IA 50273
/35
$800,000
- 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
/29
$217,400
- 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
/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
/21
$177,000
- 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
$230,000
- 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
/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. With over 3700 finished square feet- 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

Sarah Cowman Homefront Real Estate, LLC

1821 Millstream Ct, Winterset, IA 50273
/31
$299,000
- 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
/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
/35
$639,900
- 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
/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
/22
$295,000
- 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
/31
$124,000
- 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
$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

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Iowa Madison County Winterset 50273

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