Homes for Sale in 50273

• 

  

  

  /20

  $139,500

  • Land
  • 4.15 Acres
  • $33,614 per Acre

  TBD 176th Ct, Winterset, IA 50273

  Located just 2 miles north of Winterset and just east off Highway 169, this 4.15-acre property offers a rare opportunity to build your dream home in a scenic setting.Perched on a hillside overlooking the beautiful North River Valley, the property features two potential build site locations with breathtaking views. With utilities available at the highway, the groundwork is set for an easy

  Colin Ortmeier Kiloterra

  TBD 176th Ct, Winterset, IA 50273
• 

  

  

  /9

  $130,000

  • Land
  • 4.32 Acres
  • $30,093 per Acre

  0000 Saint Charles Rd, Winterset, IA 50273

  Build your dream home on this private 4.3 acre parcel with beautiful views overlooking the Middle River Valley. On hard surface with rural water and electric at the street. Close to Winterset and easy commute to Des Moines.

  Katie Bloom LPT Realty, LLC

  0000 Saint Charles Rd, Winterset, IA 50273
• 

  

  

  /11

  $655,384

  • Land
  • 96.11 Acres
  • $6,819 per Acre

  00 Millstream Ave, Winterset, IA 50273

  Premium Row Crop Ground with Endless Potential | Madison County, IowaRepresenting the Utsler Family Trust in the sale of 50.51 gross acres m/l located in Section 18 of Scott Township in Madison County. This farm consists of an estimated 48.19 FSA cropland acres currently in row crop production boasting highly productive soils including Sharpsburg, Macksburg, and Clearfield silty clay

  Andrew Zellmer Peoples Company

  00 Millstream Ave, Winterset, IA 50273
• 

  

  

  /4

  $74,500

  • Land
  • 3 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
• 

  

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /35

  $659,900

  • 4 Beds
  • 3 Baths
  • 1,788 Sq Ft

  2626 160th St, van Meter, IA 50261

  Rural Madison County Acreage! Open concept Ranch with a little more than 1800 square feet upstairs with a finished basement. Upstairs consists of large master bedroom with tray ceiling and his and her closets. Primary bedroom is huge and has its own bathroom with jetted tub, walk in shower and built in make up counter, toilet has an individual door for that added privacy. Large bedroom and

  Sarah Cowman Homefront Real Estate, LLC

  2626 160th St, van Meter, IA 50261
• 

  

  /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
• 

  

  /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
• 

  

  /33

  $667,499

  • 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 kitchen

  Kate Carlson Realty ONE Group Impact

  1634 170th 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
• 

  

  /32

  $287,500

  • 3 Beds
  • 2 Baths
  • 1,741 Sq Ft

  620 W Filmore St, Winterset, IA 50273

  **Available now for quick possesion!!**Charming Ranch with modern Updates on a Quiet Street.Welcome 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

  Alyssa Tadlock Madison County Realty

  620 W Filmore 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
• 

  

  /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
• 

  

  /27

  $185,000

  • Land
  • 10.38 Acres
  • $17,823 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
• 

  

  /18

  $305,000

  • Studio
  • 1 Bath
  • 995 Sq Ft

  418 N 6th St, Winterset, IA 50273

  Investor Alert! Super clean and well-maintained duplex investment property. Each unit has 2 bedrooms and 1 full bath. Large living room, spacious kitchen and dining area. Sliding door from the dining area leads to the backyard. The bedrooms have good size closets. 1st floor laundry. Ample storage space in the basement. 1 car attached garage. 418 N 6th St. - furnace new 2021, newer flooring and

  Jennifer Stover Madison County Realty

  418 N 6th St, Winterset, IA 50273
• 

  

  /17

  $84,500

  • 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
• 

  

  /9

  $216,000

  • 2 Beds
  • 1 Bath
  • 1,031 Sq Ft

  413 E 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

  413 E Madison St, Winterset, IA 50273
• 

  

  /8

  $220,000

  • 2 Beds
  • 1 Bath
  • 1,031 Sq Ft

  411 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 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 in bedrooms and a

  Alyssa Tadlock Madison County Realty

  411 W Madison St, Winterset, IA 50273
• 

  

  /34

  $539,000

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

  2237 Holliwell Valley Ct, Winterset, IA 50273

  Enjoy the spaciousness of a 4.3 ACRE homestead with 6 beds, 4 baths, & multiple living spaces AND $10,000 towards HOME UPDATES OF YOUR CHOICE!. With 4,700+ sq ft of finish, appreciate the comfort of a BRAND NEW Heat Pump/Air Conditioner Unit (6/2025) with 10 YEAR WARRANTY. The gorgeous kitchen features soft-close drawers, walk-in pantry, & beautiful views of the hills and neighboring pond. Relax

  Wendy Eilander RE/MAX Concepts

  2237 Holliwell Valley Ct, Winterset, IA 50273
• 

  

  /16

  $438,000

  • Land
  • 19.34 Acres
  • $22,647 per Acre

  1122 220th St, Winterset, IA 50273

  Have you been looking for the perfect recreational property? This acreage will check all of the boxes: 40X64X12 outbuilding, timber, small cabin, great hunting, pond. The outbuilding has electric, spray foam insulation, water, plumbed for bath. Don't miss the cute cabin in the middle of the timber. The cabin makes a great hunting retreat. The cabin has an electric fireplace and wall heater. This

  Jennifer Stover Madison County Realty

  1122 220th St, Winterset, IA 50273
• 

  

  /9

  $215,000

  • Land
  • 14.62 Acres
  • $14,706 per Acre

  0000 Settlers Trail, Saint Charles, IA 50240

  Discover the beauty of Madison County with this exceptional 14.62-acre property, offering the perfect blend of natural surroundings and modern amenities. This fully fenced acreage features a picturesque 1/2-acre pond, a gently flowing stream, and tree line on the east end for added privacy. The rolling hills provide an excellent opportunity to build your dream walk-out style home, maximizing the

  Greg Weinschenk Iowa Realty Beaverdale

  0000 Settlers Trail, Saint Charles, IA 50240
• 

  

  /7

  $533,000

  • Land
  • 52.75 Acres
  • $10,104 per Acre

  52.75 Acres M/L 0000 Hogback Bridge Rd, Earlham, IA 50072

  52.75 acres m/l in northern Madison County just west of US-169. Located just outside of the metro & only 25 minutes to all of the amenities in West Des Moines. This is top shelf recreation land with a combination of tillable acres, grassland, & river access. The property has 9.59 Acres in CRP paying $156.51 / acre. There are approximately 35.5 acres of tillable acres available for cash rent with

  James Von Gillern RE/MAX Concepts

  52.75 Acres M/L 0000 Hogback Bridge Rd, Earlham, IA 50072
• 

  

  /35

  $450,000

  • 5 Beds
  • 4 Baths
  • 3,520 Sq Ft

  204 W Washington St, Winterset, IA 50273

  If you're looking for ** WOW ** this. is. IT!! This stunning 1875 two story has been well cared for and offers a long list of modern amenities. Situated just a couple blocks from the historic Winterset square and close to schools, restaurants and retail on a large corner lot with outdoor living and perennials waiting for you. Relax on the wrap around porch or entertain on the back patio

  Alyssa Tadlock Madison County Realty

  204 W Washington St, Winterset, IA 50273
• 

  

  /18

  $199,000

  • Land
  • 7.14 Acres
  • $27,871 per Acre

  2368 Saint Charles Rd, Winterset, IA 50273

  BRING YOUR OWN BUILDER!!! This 7.14 acres is located right off the St Charles pavement, offering convenience and gorgeous fall views. Schedule a showing today!

  Rachel Eller Summerset Realty

  2368 Saint Charles Rd, Winterset, IA 50273
• 

  

  /7

  $119,200

  • Land
  • 2.79 Acres
  • $42,724 per Acre

  Lot 34 Limestone Ct, Winterset, IA 50273

  Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

  Julie Baudler RE/MAX Concepts

  Lot 34 Limestone Ct, Winterset, IA 50273
• 

  

  /7

  $215,000

  • Land
  • 2.91 Acres
  • $73,883 per Acre

  Lot 26 114th Ct, Winterset, IA 50273

  Have you ever dreamed of having an acreage where you are close to the DSM Metro, but still see the brightest stars shining at night? Where you have room for your kids to run and play outside or host a family or friend gathering in your matching outbuilding? Plant a garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

  Julie Baudler RE/MAX Concepts

  Lot 26 114th Ct, Winterset, IA 50273

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