Winterset, IA Houses for Sale

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  /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
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  Explore Winterset

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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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 new roof (March 2025), new water lines, a newer heating & cooling with a

  Misty Darling BH&G Real Estate Innovations

  2385 Holliwell Bridge Rd, Winterset, IA 50273
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  /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
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  /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
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  /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
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  /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
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  /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
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  /33

  $669,999

  • 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
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  /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
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  /34

  $299,000

  • 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
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  /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
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  /33

  $348,000

  • 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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /18

  $80,000

  • 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
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  /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
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  /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
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  /28

  $129,900

  • 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
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  /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
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  /32

  $183,000

  • 3 Beds
  • 1.5 Baths
  • 1,192 Sq Ft

  409 W Filmore St, Winterset, IA 50273

  Welcome to this charming and well-maintained 3-bedroom, 1.5-bath home in a quiet, established neighborhood. The spacious main floor offers abundant natural light, a functional layout, and convenient main floor laundry. The heart of the home is the large kitchen featuring ample cupboard and counter space, a generous walk-in pantry, and a new dishwasher—perfect for everyday living and entertaining.

  Misty Darling BH&G Real Estate Innovations

  409 W Filmore St, Winterset, IA 50273
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  /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
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  /34

  $585,000

  • 5 Beds
  • 3 Baths
  • 1,739 Sq Ft

  711 E Madison St, Winterset, IA 50273

  Spectular 5 bedroom ranch beautiful finish and an enormous 30x54 shop/garage with concrete floor on 1.75 acres! This home boasts a huge living room which features high ceilings and a beautiful fireplace while the formal dining room offers a bit of privacy, both with attractive hardwood floors. The kitchen has tons of storage and leads to an eating area. Off the dining area is an enormous deck

  Sarah Cowman Homefront Real Estate, LLC

  711 E Madison St, Winterset, IA 50273
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  /17

  $91,000

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  315 N 4th Ave, Winterset, IA 50273

  . 1.5-story home with a welcoming front porch and a 1-car detached garage. This home offers 3 bedrooms and 1 bath. Hardwood floors and carpet. 2 window units stay with the home. Large yard and great location!. Call today for your viewing!

  Sarah Cowman Homefront Real Estate, LLC

  315 N 4th Ave, Winterset, IA 50273
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  /35

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,913 Sq Ft

  423 E Jefferson St, Winterset, IA 50273

  Classic 1920 Craftsman with all of the charm and character you'd expect. As you walk up to the front porch you'll never want to leave! Perfect spot for your morning coffee or lounging at the end of a long day. As you enter, you'll immediately see the exposed wood beams in the family room that make it a cozy space. Newer gas fireplace is the focus of the family room, flanked by built in

  Jennifer Stover Madison County Realty

  423 E Jefferson St, Winterset, IA 50273
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  /18

  $164,500

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  408 E Benton St, Winterset, IA 50273

  Charming & Updated in Winterset! This adorable home is move-in ready with tons of recent upgrades you'll love. Step into a brand-new kitchen and bathroom featuring modern finishes, complemented by stylish LVP flooring and fresh carpet throughout. The exterior shines with new siding and windows, offering both great curb appeal and energy efficiency. Sitting on a huge yard, there's plenty of space

  Jamie Adkins RE/MAX Precision

  408 E Benton St, Winterset, IA 50273
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  /19

  $224,500

  • 3 Beds
  • 1 Bath
  • 1,118 Sq Ft

  223 N 8th St, Winterset, IA 50273

  Amazing home renovation! Sweet ranch home on a large corner lot. 3 bedroom, 1 bath, 1118sf. The all new kitchen is efficient with a breakfast bar all new cabinetry/countertops and newer stainless steel appliances. Enjoy your morning coffee in the sunny dining area right off the kitchen. The spacious breezeway is the perfect spot for 1st floor laundry and plenty of extra room for coats/shoes. Next

  Jennifer Stover Madison County Realty

  223 N 8th St, Winterset, IA 50273
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  /33

  $549,900

  • 6 Beds
  • 4 Baths
  • 3,155 Sq Ft

  2237 Holliwell Valley Ct, Winterset, IA 50273

  Remarks: Welcome home! This 4.3 acre homestead will allow you to enjoy life to the fullest. Step into a spacious home with over 4,700 sq ft total of finished living space. At the heart of the home is a gorgeous kitchen with soft-close drawers, a walk-in pantry, and breathtaking views of the countryside hills and peaceful neighboring pond—best enjoyed from the sunny dining area or

  Wendy Eilander RE/MAX Concepts

  2237 Holliwell Valley Ct, Winterset, IA 50273

Showing Results 1 - 40, Page 1 of 2

Why Live in Winterset

Winterset is a south-central Iowa city where John Wayne learned to walk and Clint Eastwood fell in love. This rural destination of about 5,400 is the birthplace of “The Duke,” who went on to Hollywood superstardom. “The Bridges of Madison County,” ...

Learn more about living in Winterset

Home Trends in Winterset, IA

On average, homes in Winterset, IA sell after 105 days on the market compared to the national average of 70 days. The median sale price for homes in Winterset, IA over the last 12 months is $190,000, down 16% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$190,000

Median Single Family Sale Price

$251,000

Median 2 Bedroom Sale Price

$192,000

Average Price Per Sq Ft

$222

Number of Homes for Sale

5

Last 12 months Home Sales

31

Months of Supply

1.90

Median List Price

$311,000

Median Change From 1st List Price

4%

Median Home Sale Price YoY Change

-16%