35

Winterset, IA Houses for Sale

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  • /27

    $234,900

    $20K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 962 Sq Ft

    710 N 3rd Ave, Winterset, IA 50273

    Corner lot three-bedroom, one bath ranch with attached garage on Winterset West side. Home has fenced yard, great fire pit area for outdoor entertaining, contained decorative garden/flower beds and a row of new trees. Other new yard features include landscaping rock and creative oval garden landscaping mound. Updates include fully encapsulated deep crawl space with warranty and new sump pump.

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 949-4406

    710 N 3rd Ave, Winterset, IA 50273
  • /35

    $410,000

    $64K PRICE DROP
    • 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

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 824-5239

    1913 N 1st St, Winterset, IA 50273
  • /27

    $325,000

    • 4 Beds
    • 2.5 Baths
    • 1,540 Sq Ft

    511 W Washington St, Winterset, IA 50273

    Welcoming 1 1⁄2 story brick home on Winterset West side. Recent remodel, galley kitchen, main floor bedroom and full bath. Living room open to dining area. Handy drop zone near rear door from detached garage. Full unfinished basement with included washer and dryer and 1⁄2 bath with a bonus laundry sink and workshop area. Three bedrooms on the second level hardwood floors and full bath upstairs.

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 800-4015

    511 W Washington St, Winterset, IA 50273
  • /33

    $478,750

    • 2 Beds
    • 2 Baths
    • 4,424 Sq Ft

    2980 Clark Tower Rd, Winterset, IA 50273

    Located in scenic Madison County this newly built home and buildings offers peace and quiet with close commute to Winterset and West Des Moines. Located on hard surface road 8.5 miles south of Winterset. The home offers 2 bedrooms and 2 baths. The main floor offers an open concept with a nice main living and dining area. The upstairs offers the opportunity to expand to increase finished square

    Iowa Company Iowa Land Company

    2980 Clark Tower Rd, Winterset, IA 50273
  • /35

    $339,900

    $10K PRICE DROP
    • 6 Beds
    • 3 Baths
    • 1,800 Sq Ft

    117 E North St, Winterset, IA 50273

    Welcome to timeless Americana charm in the heart of beautiful Winterset. Nestled on a quiet, tree lined street just moments from the beloved historic square, this spacious 2 sty offers warmth, character and a sense of community that make Winterset such a special place to call home. With 6 bedrooms and 3 baths, this home offers remarkable flexibility and room to grow. 4 bedrooms are on 2nd level

    Lisa Davis RE/MAX Precision

    117 E North St, Winterset, IA 50273
  • /23

    $299,900

    • 3 Beds
    • 2 Baths
    • 838 Sq Ft

    521 W Hutchings St, Winterset, IA 50273

    Walk out ranch home with huge yard! This is a must see property! You will appreciate the updated inside featuring a bright eat in kitchen (the kitchen appliances are all included!). The living room has a cozy electric fireplace and nice big windows overlooking the huge back yard. There are 2 bedrooms and a full bath upstairs. The basement is a bright sunny walk out with a large family room,

    Sarah Cowman Homefront Real Estate, LLC

    521 W Hutchings St, Winterset, IA 50273
  • /35

    $335,000

    • 4 Beds
    • 1,470 Sq Ft

    1405 W Jefferson St, Winterset, IA 50273

    Welcome to this well-maintained 4 bedroom, 3 bathroom home offering just under 1,500 square feet of comfortable living space in one of Central Iowa?s most charming communities. This home features a functional layout with spacious living areas, abundant natural light, and plenty of room for both everyday living and entertaining.The main living space offers a warm and inviting feel with an open

    Matt Law RE/MAX Precision

    1405 W Jefferson St, Winterset, IA 50273
  • /34

    $275,000

    • 3 Beds
    • 2 Baths
    • 1,705 Sq Ft

    524 W Benton St, Winterset, IA 50273

    Full of cozy charm and timeless character, this delightful Cape Cod-style home offers 1,705 square feet of warm and inviting living space. Built in 1964, the home features 3 bedrooms — including a convenient main-floor bedroom and bath — designed for comfortable everyday living. 2 living rooms - one with oversized picture windows to take in the natural light and the other room features a

    Jennifer Stover Madison County Realty

    524 W Benton St, Winterset, IA 50273
  • /34

    $365,000

    $10K PRICE DROP
    • 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
  • /24

    $309,000

    $11K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    212 N 14th Ave, Winterset, IA 50273

    Sweet ranch home located on a quiet street. The open concept floor plan makes this house feel bigger than it is. The 1st floor offers 2 large bedrooms, 1 full bath, kitchen with a breakfast bar and a private home office space. The lower level features a huge family room, large bedroom and full bath - and still plenty of storage space. Sliding door off the dining area leads to the private

    Jennifer Stover Madison County Realty

    212 N 14th Ave, Winterset, IA 50273
  • /28

    $365,000

    • 3 Beds
    • 2.5 Baths
    • 1,669 Sq Ft

    1514 MacKensie Cir, Winterset, IA 50273

    Spacious 2 story home in the Birchwood development. 3 bedrooms, 2.5 baths, 1669sf. Modern open floor plan. Large kitchen and dining area. Sliding door from dining area leads to the deck. Just off the kitchen is a home office/formal dining room. The 2nd floor features 3 generous bedroom, 2 baths, and laundry room. The lower level is ready for the new homeowners to finish for even more living

    Jennifer Stover Madison County Realty

    1514 MacKensie Cir, Winterset, IA 50273
  • /35

    $339,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft

    2197 175th Ct, Winterset, IA 50273

    Want to own a slice of Heaven?! This is it! Fully renovated acreage just off pavement about 3 miles north of charming and growing Winterset and about 7 miles south of DeSoto and I80. Spacious ranch alongside the North River with stunning finishings. Open concept at its finest with vaulted ceilings and daylight everywhere you look! Incredible kitchen that you'll want to show off as you host all

    Ambria Vogt RE/MAX Precision

    2197 175th Ct, Winterset, IA 50273
  • /29

    $299,000

    • 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 massive 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 craft

    Alyssa Tadlock Madison County Realty

    203 W Green St, Winterset, IA 50273
  • /27

    $269,900

    • 3 Beds
    • 1 Bath
    • 1,859 Sq Ft

    319 S 7th Ave, Winterset, IA 50273

    WELCOME HOME to this beautiful 3 bed/1 bath home on .32 ac lot. You will LOVE walking into the large living room, with plenty of NATURAL LIGHT and nice sized dining area. The kitchen has plenty of COUNTER SPACE and also a nice sized ISLAND. Off of the kitchen is the large 4 SEASON PORCH/family room (12'x33') with plenty of windows and natural light. The perfect area for ENTERTAINING! Two bedrooms

    Betsy Breeding Realty ONE Group Impact

    319 S 7th Ave, Winterset, IA 50273
  • /31

    $274,900

    $40K PRICE DROP
    • 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
  • /34

    $1,225,000

    • 5 Beds
    • 5 Baths
    • 2,434 Sq Ft

    2188 114th Ct, Winterset, IA 50072

    Welcome to modern acreage living at its finest! Set on 5.32 picturesque acres in gorgeous Madison County and located in the highly desirable Adel school district, this stunning home offers the perfect blend of peaceful country living with everyday convenience. Just 13 minutes from Grand Prairie Parkway, you’ll enjoy an easy drive on all blacktop roads—no gravel! Inside, discover 4,593 sq ft of

    Julie Baudler RE/MAX Concepts

    2188 114th Ct, Winterset, IA 50072
  • /34

    $595,000

    • 5 Beds
    • 3.5 Baths
    • 4,200 Sq Ft

    505 E Court Ave, Winterset, IA 50273

    Step into timeless character with this stately 19th-century home, showcasing stunning original woodwork and rich architectural charm throughout. Set on an expansive lot, the property features a 4-car attached garage, a welcoming wrap around porch, and plenty of parking space. Inside, you’ll find a beautiful open floor plan designed for both everyday living and entertaining. The spacious living

    Sarah Cowman Homefront Real Estate, LLC

    505 E Court Ave, Winterset, IA 50273
  • /27

    $225,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,095 Sq Ft

    619 N 10th St, Winterset, IA 50273

    Adorable and thoughtfully updated 1 1/2 story home in historic Winterset, featuring a 2006 lift with a full poured-concrete basement. The main level offers a bright eat-in kitchen with all appliances included, whih opens to a deck - perfect for grilling. Off the kitchen is a full bathroom with laundry! There is a main floor bedroom that could also be used as a living room or flex space. Upstairs

    Sarah Cowman Homefront Real Estate, LLC

    619 N 10th St, Winterset, IA 50273
  • /13

    $210,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,031 Sq Ft

    411 W Madison St, Winterset, IA 50273

    Looking to downsize? Just starting out? This is home! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower with tile surround and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and

    Alyssa Tadlock Madison County Realty

    411 W Madison St, Winterset, IA 50273
  • /17

    $180,000

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    402 N 9th St, Winterset, IA 50273

    Well maintained ranch on a corner lot. Open floor plan with 1,152 sf, 3 bedroom, 1 full bath. 1st floor laundry room. Spacious kitchen and dining area. Gas fireplace in living room. Large covered patio space - perfect for grilling all year and relaxing in the summer. Parking pad for 2 cars. Newer roof.

    Randall Henry Madison County Realty

    402 N 9th St, Winterset, IA 50273
  • /11

    $210,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,031 Sq Ft

    409 W Madison St, Winterset, IA 50273

    Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower with tile surround and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet

    Alyssa Tadlock Madison County Realty

    409 W Madison St, Winterset, IA 50273
  • /23

    $234,900

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,006 Sq Ft

    113 S 3rd St, Winterset, IA 50273

    Move-in ready and totally remodeled 3-bed 2.5-bath ranch! Everything you need is on the main level. This home has been thoughtfully renovated, utilizing every square inch. Walk in, and you will appreciate the large entry way ready for your locker system or bench area. The living room is bright and spacious and is open to the kitchen. The kitchen has nice counter and cabinet space with a pantry

    Sarah Cowman Homefront Real Estate, LLC

    113 S 3rd St, Winterset, IA 50273
  • /26

    $215,000

    • 2 Beds
    • 2 Baths
    • 1,042 Sq Ft

    406 N 7th St, Winterset, IA 50273

    This home was a complete remodel down to the studs in 2024, with New Electric, Plumbing, Drywall, Doors, Windows, Trim...Everything! This property has a spacious kitchen, 2 bedrooms, 2 baths and a large, flat backyard! There are all new windows with nice natural light. Off of the living room is a back deck overlooking the backyard. The eat in kitchen is very spacious with nice cabinet space,

    Dakoda Overbeck Iowa Realty Waukee

    406 N 7th St, Winterset, IA 50273
  • /12

    $206,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,031 Sq Ft

    407 W Madison St, Winterset, IA 50273

    Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower with tile surround and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet

    Alyssa Tadlock Madison County Realty

    407 W Madison St, Winterset, IA 50273
  • /34

    $579,900

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,432 Sq Ft

    719 E Washington St, Winterset, IA 50273

    Discover the ultimate "wow factor" in this stunning Winterset property, truly like anything else. It’s been completely rebuilt to marry historic soul with modern luxury. This isn't just a renovation; it’s a turnkey masterpiece designed for entertaining and everyday living; featuring a main-level primary retreat bathed in incredible natural sunlight throughout the home. It includes 3 bedrooms +

    Sarah Cowman Homefront Real Estate, LLC

    719 E Washington St, Winterset, IA 50273
  • /12

    $210,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,031 Sq Ft

    405 W Madison St, Winterset, IA 50273

    Looking to downsize? Just starting out? This is it! 2 bed, 1 bath tri-plex features zero-step entry and 36" doorways throughout as well as ADA shower with tile surround and ADA toilet for safe, easy and convenient access. The open floor plan includes vaulted ceilings in living, kitchen and dinning rooms and tray ceiling in the master. It's completed with LVP flooring in the main rooms and carpet

    Alyssa Tadlock Madison County Realty

    405 W Madison St, Winterset, IA 50273
  • /24

    $262,500

    • 4 Beds
    • 2 Baths
    • 1,482 Sq Ft

    610 W Washington St, Winterset, IA 50273

    Charming Cape Cod with space, style, and a location you’ll love. This well-maintained 1.5-story home offers 1,482 square feet of inviting living space, featuring 4 bedrooms and 2 bathrooms designed for comfort and flexibility. Step inside to find a home that has been exceptionally cared for—clean, bright, and move-in ready. The layout offers a cozy yet functional flow, with a finished lower level

    Larry Corkrean Madison County Realty

    610 W Washington St, Winterset, IA 50273
  • /2

    $159,900

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    510 E Court Ave, Winterset, IA 50273

    3-bedroom ranch with a 2-car detached garage offering tons of potential! Recent updates include a new roof, exterior paint, boiler, and garage door. Home is in need of TLC and cosmetic updates but provides a great opportunity for buyers looking to add their own touch. Solid bones with plenty of possibilities! photos coming soon

    Rachel Eller Summerset Realty

    510 E Court Ave, Winterset, IA 50273
  • /35

    $384,900

    $14K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 1,720 Sq Ft

    704 N 14th Ave, Winterset, IA 50273

    Tucked at the end of a quiet street, this 4-bedroom home sits on an oversized lot in a welcoming neighborhood. You'll love the fully fenced yard, wooden fencing, and large deck, perfect for enjoying the outdoors.Inside, the main level offers a functional layout with a drop zone at the front entry, a dedicated office/study, and a spacious living area with a cozy fireplace. The kitchen features

    Ashlee & Kyle Knickerbocker Keller Williams Realty GDM

    704 N 14th Ave, Winterset, IA 50273
  • /17

    $159,000

    $6K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,286 Sq Ft

    415 E Buchanan St, Winterset, IA 50273

    Affordable, fully updated and ready-to-move-in ranch in the heart of Winterset! Offering 1,286 sq ft, this home features a well-designed main-level layout with comfortable living space and a first-floor bedroom. Enjoy the added charm of a 3-season room perfect for relaxing or entertaining. Equipped with natural gas heating, city water and sewer, and included kitchen appliances for added

    Anagha Berodia Iowa Realty Waukee

    415 E Buchanan St, Winterset, IA 50273
  • /34

    $389,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,574 Sq Ft

    222 Oak Tree Dr, Winterset, IA 50273

    Well cared for one-owner home featuring 3 bedrooms, 3 bathrooms with high 9 ft ceilings that create a bright, open feel throughout the main living area. The thoughtfully designed floor plan includes a functional kitchen, and a primary suite with a private bath. Enjoy the 4-season porch, perfect for relaxing or entertaining year round. The basement is ready to finish, already drywalled just

    Amber Stemler Iowa Realty Mills Crossing

    222 Oak Tree Dr, Winterset, IA 50273
  • /32

    $140,000

    • 2 Beds
    • 2.5 Baths
    • 1,548 Sq Ft

    906 S 4th Ave, Winterset, IA 50273

    Opportunity awaits in this 1.5-story home located at 906 S 4th Ave in Winterset, right next to the high school. This property offers a functional layout with a main floor bedroom, 1.5 baths, and convenient main floor laundry. Upstairs you'll find an additional bedroom, a full bathroom, and a non-conforming bedroom--providing flexible space for a variety of needs. Outside features include a 2-car

    Dezaray Buchwald iHome Realty

    906 S 4th Ave, Winterset, IA 50273
  • /34

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,396 Sq Ft

    302 W Court Ave, Winterset, IA 50273

    Timeless charm meets thoughtful updates in this classic 2-story home built in 1890, ideally located on historic Court Ave just one block from the town square. Offering 2,396 square feet, 3 bedrooms, and 2.5 baths, this beautifully maintained home blends original character with modern functionality in all the right ways. The showstopping custom-designed kitchen is truly the heart of the home,

    Jennifer Stover Madison County Realty

    302 W Court Ave, Winterset, IA 50273
  • /17

    $239,900

    • 4 Beds
    • 2 Baths
    • 1,270 Sq Ft

    1413 W Washington St, Winterset, IA 50273

    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
  • /27

    $330,000

    • 4 Beds
    • 3 Baths
    • 1,990 Sq Ft

    1706 W Summit St, Winterset, IA 50273

    This two-story brick home, built in 1923, has all of the character and charm that goes with a 1920s house. Original built-ins, woodwork, hardwood floors and glass doorknobs still remain in the house. With 1990 sf, 4 bedroom and 3 baths, there is plenty of room for everyone. The first floor features a large family room with beautiful built-ins surrounding the fireplace. French doors from the

    Larry Corkrean Madison County Realty

    1706 W Summit St, Winterset, IA 50273

Why Live in Winterset

Winterset, IA, is a small city with a rich historical backdrop and ties to Hollywood legends John Wayne and Clint Eastwood. Known for its welcoming community, Winterset attracts tourists year-round with the John Wayne Birthplace Museum and the renowned covered bridges of Madison County. The city hosts annual events like the John Wayne birthday celebration in May and the Covered Bridge Festival in October, featuring over 150 vendors, a parade, and a classic car show. Winterset’s housing options include historic homes with Colonial Revival and Victorian influences, contemporary models in subdivisions, and homes on larger plots north of town. The city’s architecture is complemented by walkable streets shaded by mature trees. City Park, listed on the National Register of Historic Places, offers attractions such as the Cutler-Donahue Covered Bridge, Clark Tower, and a hedge maze, along with recreational facilities like a soccer complex, softball fields, and a skate park. Downtown Winterset maintains an old-time, small-town vibe with boutique shops, vintage stores, and family businesses centered around the Madison County Courthouse square. Dining options are plentiful, particularly along John Wayne Drive. The Winterset Community School District includes four schools, with Winterset Junior High being the highest rated. Located about 35 miles from Des Moines, Winterset is accessible via U.S. Highway 169 and Iowa Highway 92, connecting to major interstates and the Des Moines International Airport.

Home Trends in Winterset, IA

Housing Trends

Median Sale Price
$260,000
Median Single Family Sale Price
$269,900
Median 2 Bedroom Sale Price
$211,500
Median 1 Bedroom Sale Price
$217,000
Median Studio Sale Price
$285,000
Average Price Per Sq Ft
$189
Number of Homes for Sale
35
Last 12 months Home Sales
103
Months of Supply
4.10
Median List Price
$269,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
11%
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