Homes for Sale in 50273

• 

  

  

  /6

  $385,500

  • Land
  • 22 Acres
  • $17,523 per Acre

  TBD Us Hwy 169 None, Winterset, IA 50273

  Build your dream home and enjoy incredible 360-degree countryside views from this beautiful 11-acre property in Madison County, just south of DeSoto. The elevated setting at the top of the hill offers an ideal location for your future home, with wide-open views in every direction and very few neighbors nearby. Enjoy the privacy and peaceful setting of country living without giving up convenience.

  Scott Wendl RE/MAX Precision

  TBD Us Hwy 169 None, Winterset, IA 50273
• 

  

  

  /33

  $295,000

  • 3 Beds
  • 1.5 Baths
  • 1,976 Sq Ft

  612 W Jefferson St, Winterset, IA 50273

  Introducing a soaring piece of Winterset architectual history in this 1905 Colonial two story. A sweeping wrap around porch invites you in upon entry, perfect for late summer nights or early morning coffee conversations. Upon entry, the grand foyer greets you, opening to an elaborate hardwood staircase featuring handcrafted balusters. Fall in love with the soaring ceilings, wide baseboards, and

  Tanner Couch LPT Realty, LLC

  612 W Jefferson St, Winterset, IA 50273
• 

  

  

  /16

  $299,900

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft

  1018 N 3rd Ave, Winterset, IA 50273

  This well-maintained townhome is in the perfect location on the end of a quiet cul-de-sac. The open layout has beautiful wood floors, vaulted ceilings, and a cozy gas fireplace that creates a welcoming focal point in the living room. The main level offers spacious living and dining areas, a functional kitchen, and two bedrooms. The primary bedroom features a walk-in closet and private ensuite

  Amy Jones HomeCoin.com

  1018 N 3rd Ave, Winterset, IA 50273
• 

  

  

  /28

  $215,000

  • Land
  • 7.48 Acres
  • $28,743 per Acre

  0 Hogback Bridge Rd, Winterset, IA 50273

  Offering a rare opportunity to own 7.48 acres m/l just north of Winterset, Iowa. Located along Hogback Bridge Road, this property offers the space and country setting many acreage buyers are searching for while remaining only minutes from the conveniences of Winterset and providing easy access toward the Des Moines metro. The property features an attractive potential building site with an

  Kolt Kiburz Peoples Company

  0 Hogback Bridge Rd, Winterset, IA 50273
• 

  

  

  /12

  $250,000

  • Land
  • 3.24 Acres
  • $77,160 per Acre

  Lot 9 Polo Pointe 2 None, Cumming, IA 50061

  Bring your dream home to life on this beautiful 3.24-acre wooded, walkout lot in Cumming's desireable Polo Pointe neighborhood. Enjoy incredible panoramic views to the west and north!

  Shannon Salmon RE/MAX Concepts

  Lot 9 Polo Pointe 2 None, Cumming, IA 50061
• 

  

  /35

  $990,000

  • 4 Beds
  • 5 Baths
  • 3,076 Sq Ft

  2381 Highway 169, Winterset, IA 50273

  This executive acreage has so much to offer! Located on pavement, just outside of Winterset, in beautiful Madison County. The perfect amount of land, completely updated spacious home, and a one-of-a kind premium shop make this property a must see! The two-story home features four bedrooms, five bathrooms, 4,000+ finished sqft, numerous living and entertaining spaces, office/study, screened porch,

  Jeffrey Longman RE/MAX Precision

  2381 Highway 169, Winterset, IA 50273
• 

  

  /3

  $39,900

  • Land
  • 2.86 Acres
  • $13,951 per Acre

  1600 Roseman Bridge Rd, Winterset, IA 50273

  Discover your little slice of heaven. This opportunity to own a couple acres along the Middle River is a unique one that will allow for many outdoor activities. Want a spot to picnic? have a garden? Maybe you'd like to riverside camp? This gem may be just the ticket! (Address is fictitious and for general location purposes only)

  Dan Wilson SoldWilson Real Estate and Auc

  1600 Roseman Bridge Rd, Winterset, IA 50273
• 

  

  /11

  $75,000

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft

  624 W Summit St, Winterset, IA 50273

  Good location for this 1 bedroom, 1 bath ranch home. Located on a large corner lot(76x102). This property would make a great investment opportunity. This property could be zoned commercial or residential.

  Randall Henry Madison County Realty

  624 W Summit St, Winterset, IA 50273
• 

  

  /23

  $194,000

  • Land
  • 13.88 Acres
  • $13,977 per Acre

  000 Clark Tower Rd, Winterset, IA 50273

  Discover the possibilities with this 13.88 +/- acre property in Madison County, offering a desirable mix of open pasture and mature timber. With multiple potential building sites, this property provides the flexibility to create your ideal country home or recreational retreat.The property is conveniently located on pavement, with water and power available at the road, making it

  Aaron Creger Midwest Land Group

  000 Clark Tower Rd, Winterset, IA 50273
• 

  

  /28

  $310,000

  • 4 Beds
  • 2 Baths
  • 1,032 Sq Ft

  401 E Benton St, Winterset, IA 50273

  Welcome home to this warm and inviting ranch offering comfortable living space both upstairs and down! Built in 1995, this 4-bedroom(2 beds on 1st flr, 2 LL) 2-bath home features 1,032 square feet on the main level plus an impressive 936 square feet of finished lower-level space, giving you plenty of room to spread out. The spacious enclosed breezeway is a standout feature, creating the perfect

  Jennifer Stover Madison County Realty

  401 E Benton St, Winterset, IA 50273
• 

  

  /35

  $254,000

  • 4 Beds
  • 1 Bath
  • 1,338 Sq Ft

  703 E Filmore St, Winterset, IA 50273

  Proudly sitting on a corner lot with many all-new features in 2026. It's a perfect blend of the past and present Be the first to live in this newly remodeled home with all new light fixtures, a larger kitchen, added bedroom closet storage, fresh paint, new hardware, smart siding, metal roof and more. Four-bedroom home with one BR on the main floor and 3 bedrooms on the second level. Large living

  

  Toni Tindle

  Covered Bridge Realty

  703 E Filmore St, Winterset, IA 50273
• 

  

  /23

  $234,900

  $5K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,241 Sq Ft

  816 E Washington St, Winterset, IA 50273

  Charming and well located, this 3 bed, 1.5 bath home sits on a quiet street just a shortdistance from Winterset’s vibrant town square. The main floor features a living room, large dining room, andfunctional kitchen, along with a convenient main floor bedroom and half bath. Upstairs offers two additionalbedrooms and a full bathroom. Outside, enjoy a private backyard with a patio—perfect for

  Laurel Pangman Keller Williams Realty GDM

  816 E Washington St, Winterset, IA 50273
• 

  

  /29

  $210,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 964 Sq Ft

  110 N 10th Ave, Winterset, IA 50273

  Located in a desirable Winterset neighborhood, this ranch home offers hardwood floors throughout, three main floor bedrooms, an eat-in kitchen with plenty of countertop space, and two spacious family rooms, one on the main level and one in the finished lower level. The attached one-car garage is complemented by an additional parking pad for extra convenience. The lower level also provides

  Kyle Kuhns RE/MAX Revolution

  110 N 10th Ave, Winterset, IA 50273
• 

  

  /35

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 1,884 Sq Ft

  1582 N River Trail, Winterset, IA 50273

  A rare Madison County property where country living, history & opportunity come together on 44.88 acres—just 25 min to West Des Moines & 15 min to Winterset. Professionally restored native prairie grasses & wildflowers with mowed trails, timber, 2 ponds (1 stocked), full fencing & sweeping countryside views create an exceptionally private setting with spectacular dark skies. The 3,468 SF finished

  Heather Helland RE/MAX Precision

  1582 N River Trail, Winterset, IA 50273
• 

  

  /61

  $478,577

  • Land
  • 68.86 Acres
  • $6,950 per Acre

  1479 280th St, Winterset, IA 50273

  Located northeast of Macksburg and southwest of Winterset, this 68.86-acre m/l Madison County farm offers an excellent combination of CRP income, mature timber, wildlife habitat, and recreation. The property includes 46.71 acres enrolled in CRP, generating $11,052 annually through September 30, 2033. The balance of the farm features substantial timber and wooded cover, creating outstanding

  Garret Armstrong Whitetail Properties Real Estate, LLC

  1479 280th St, Winterset, IA 50273
• 

  

  /35

  $349,000

  • 4 Beds
  • 2 Baths
  • 2,430 Sq Ft

  310 W Washington St, Winterset, IA 50273

  A truely unique and well kept historic home is ready for new owners. The character is abundant in this sprawling 2 story home. Walk in the front door and you will be greeted by a sweet vestibule for sitting and taking off shoes and hanging up your jacket. You will be greeted with a large front living room with stunning gas fireplace and lots of windows for natural light. There is an

  Sarah Cowman Homefront Real Estate, LLC

  310 W Washington St, Winterset, IA 50273
• 

  

  /47

  $537,513

  • Land
  • 77.34 Acres
  • $6,950 per Acre

  1474 280th St, Winterset, IA 50273

  Located northeast of Macksburg and southwest of Winterset, this 77.34-acre m/l Madison County property offers an attractive combination of income, recreation, wildlife habitat, and potential building opportunities. The farm is enrolled in the Conservation Reserve Program (CRP), providing an annual payment of $10,647.00 while maintaining established grassland habitat. The CRP cover, combined with

  Garret Armstrong Whitetail Properties Real Estate, LLC

  1474 280th St, Winterset, IA 50273
• 

  

  /34

  $464,900

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 1,807 Sq Ft

  305 Magnolia Point, Winterset, IA 50273

  If you are from Winterset, you know. If you are considering a move to Winterset, this town is one of the most beautiful ones in Iowa... the landscape, the hills - just incredibly picturesque. Then, you come upon 305 Magnolia Pt. A home built with care in 2023, requiring little maintenance. The thoughtful floor plan includes a mudroom area upon entering and a staircase staggered back a bit to

  Rachel Wallace RE/MAX Precision

  305 Magnolia Point, Winterset, IA 50273
• 

  

  /28

  $299,900

  • 4 Beds
  • 2 Baths
  • 2,281 Sq Ft

  322 W Washington St, Winterset, IA 50273

  Step into the timeless charm of this beautiful 4-bedroom, 2-bath Victorian home in the heart of Winterset! Blending classic character with thoughtful updates, this home features original hardwood floors, newer exterior paint, light fixtures, refrigerator, storm doors, and a fully fenced quarter-acre yard. The roof was replaced in 2020, giving added peace of mind. Outside, you'll find fruit trees,

  Joanne May RE/MAX Concepts Main Office

  322 W Washington St, Winterset, IA 50273
• 

  

  /34

  $275,000

  $5K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,146 Sq Ft

  602 N 1st Ave, Winterset, IA 50273

  Step into the timeless charm of this spacious Victorian home, perfectly situated on a corner lot in one of historic Winterset's established neighborhoods. With four bedrooms and multiple bathrooms, there's plenty of room for family, guests, or a growing household.The home offers both an inviting eat-in kitchen and a formal dining room, providing flexible spaces for everyday meals or

  Kate Carlson Realty ONE Group Impact

  602 N 1st Ave, Winterset, IA 50273
• 

  

  /15

  $43,900

  • 3 Beds
  • 2 Baths
  • 1,216 Sq Ft

  1624 W Summit St Unit 115, Winterset, IA 50273

  Discover the perfect blend of comfort and space in this beautiful 3-bedroom, 2-bath home featuring a spacious open-concept floor plan designed for today's lifestyle. The inviting layout creates a seamless flow between the living, dining, and kitchen areas, making everyday living and entertaining effortless. Generously sized bedrooms, ample natural light, and thoughtfully designed living spaces

  Mahayla Claiser Covered Bridges MHP

  1624 W Summit St Unit 115, Winterset, IA 50273
• 

  

  /35

  $440,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,484 Sq Ft

  1515 W Washington St, Winterset, IA 50273

  Imagine a home where you don't have to compromise on a single detail. Welcome to 1515 W Washington St in Winterset—a gorgeous brick home offering 2,484 finished sq ft on the main level alone! This 3-bed, 2-bath layout features an impressive flow centered around a dual-sided fireplace, creating the perfect gathering space. The chef's kitchen boasts sleek quartz countertops, extensive cabinet

  Ian Sparks Homefront Real Estate, LLC

  1515 W Washington St, Winterset, IA 50273
• 

  

  /30

  $205,000

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 986 Sq Ft

  306 E Buchanan St, Winterset, IA 50273

  Well kept and adorable 2 bed 1 bath ranch home. You will love the character in this sweet easy one level living home just blocks from the historic Winterset square. original hardwood floors and trim throughout with all the essentials renovated including a new metal roof in 2025. The covered front porch greets you and is the perfect spot for morning coffee. The bedrooms are generous sized and have

  Sarah Cowman Homefront Real Estate, LLC

  306 E Buchanan St, Winterset, IA 50273
• 

  

  /14

  $69,900

  • 3 Beds
  • 1 Bath
  • 1,221 Sq Ft

  313 E North St, Winterset, IA 50273

  Rare opportunity in historic Winterset! This 3-bedroom, 1-bath home offers approximately 1,221 square feet and is ready for a complete renovation. Great neighborhood, and close the historic Winterset square. Property is being sold strictly As-Is. Ideal for investors, contractors, or buyers looking for their next rehabilitation project. Excellent opportunity to restore a classic 1900 home and

  Roger Queck Pro Team Realty

  313 E North St, Winterset, IA 50273
• 

  

  /30

  $177,500

  $8K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  715 N 5th St, Winterset, IA 50273

  Welcome home to 715 N 5th Street! Nestled on the peaceful north edge of town, this home offers the perfect blend of affordable living and small town charm! You will love the spacious design, featuring oversized closets in every bedroom, including a private primary suite complete with a relaxing garden tub. Situated right in the heart of convenience, you're just minutes from all the local

  Kenneth Kauzlarich RE/MAX Precision

  715 N 5th St, Winterset, IA 50273
• 

  

  /28

  $4,938,450

  • Land
  • 451.34 Acres
  • $10,942 per Acre

  00 N River School Rd, Winterset, IA 50273

  Peoples Company is proud to present the Hogback Farm, an exceptional 451 acre m/l recreational and income-producing property located in the heart of Madison County, Iowa, just a short drive from the Des Moines metro. Tucked into a highly desirable corridor between the vibrant and growing communities of Winterset and Adel, less than one mile from paved US Highway 169, this property offers a rare

  Bryan Bergdale Peoples Company

  00 N River School Rd, Winterset, IA 50273
• 

  

  /33

  $474,000

  • 3 Beds
  • 2.5 Baths
  • 2,616 Sq Ft

  1818 Patricia Acres, Winterset, IA 50273

  WELCOME HOME to this beautiful, CUSTOM-BUILT home on 2.1 private acres. Did I mention how CLOSE it is to Winterset? The main floor has a nice sized LIVING ROOM and FORMAL DINING ROOM, with an abundance of windows, for plenty of NATURAL LIGHT. The kitchen with GRANITE countertops, STAINLESS STEEL APPLIANCES that stay, also has a nice breakfast nook and opens to the large family room with a wood

  Betsy Breeding Realty ONE Group Impact

  1818 Patricia Acres, Winterset, IA 50273
• 

  

  /29

  $4,938,450

  • Land
  • 451.34 Acres
  • $10,942 per Acre

  0 N River School Rd Unit 745575, Winterset, IA 50273

  We are proud to present the Hogback Farm, an exceptional 451 acre m/l recreational and income-producing property located in the heart of Madison County, Iowa, just a short drive from the Des Moines metro. Tucked into a highly desirable corridor between Winterset and Adel, less than one mile from paved Highway 169, this property offers a rare combination of privacy, natural beauty, and

  Bryan Bergdale Peoples Company

  0 N River School Rd Unit 745575, Winterset, IA 50273
• 

  

  /28

  $4,938,450

  • Land
  • 451.34 Acres
  • $10,942 per Acre

  0 N River School Rd Unit NOC6340580, Winterset, IA 50273

  Peoples Company is proud to present the Hogback Farm, an exceptional 451 acre m/l recreational and income-producing property located in the heart of Madison County, Iowa, just a short drive from the Des Moines metro. Tucked into a highly desirable corridor between Winterset and Adel, less than one mile from paved Highway 169, this property offers a rare combination of privacy, natural beauty, and

  Bryan Bergdale Peoples Company

  0 N River School Rd Unit NOC6340580, Winterset, IA 50273
• 

  

  /24

  $740,000

  • Land
  • 55.42 Acres
  • $13,353 per Acre

  2039 145th Ln, Earlham, IA 50072

  55.42 ACRES IN TOTAL. Build your secluded dream home, hunting lodge or Airbnb just 20 minutes from the metro in Madison County. Lot 3 is 15.42 acres and the north parcel is 40 acres of timber and some alfalfa on the west. The property is located on a secluded high ridge with mature trees and great views in all directions. Lot 3 has its own dedicated driveway and is owned with Lot 3. Hunters

  Kirk Bjorland LPT Realty, LLC

  2039 145th Ln, Earlham, IA 50072
• 

  

  /18

  $213,000

  $12K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 848 Sq Ft

  121 E Benton St, Winterset, IA 50273

  If you are looking for a starter home or a nice home to downsize, you need to take a look at this one. This 2 bedroom, 1 bath is handicap accessible, built in 1932 with 848sf, with a living room, dining, hardwood floors and natural woodwork. Included with this home is a full size pool table, bar/chairs. The home has a large garage built in 2004(28x36) with an unfinished attic for additional

  Larry Corkrean Madison County Realty

  121 E Benton St, Winterset, IA 50273
• 

  

  /26

  $699,000

  • 4 Beds
  • 3.5 Baths
  • 1,546 Sq Ft

  Lot 5 Hogback Bridge Rd, Earlham, IA 50072

  Proposed new build by Graystone Construction situated on Lot 6, 5 acres of the NEW Cottonwood Creek Acreages in beautiful Madison County. This proposed home with 2666 sq ft of living space features a walkout ranch plan with open concept great room, 2 bedrooms on the main level, and 2 bedrooms and a family gathering space in the lower level. Main level includes split bedroom layout w/ bed#2 having

  Brett Baker RE/MAX Concepts

  Lot 5 Hogback Bridge Rd, Earlham, IA 50072
• 

  

  /34

  $559,000

  $6K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,506 Sq Ft

  5219 Cherrywood Ln, Winterset, IA 50273

  Stunning 4 bed (5 non-conforming) 3 bath home nestled on 2.24 acres! Walking in you are instantly drawn to over-sized windows showcasing a beautiful backyard. Home features 2x6 exterior walls & 9' ceilings. Kitchen has 11' long single piece quartz island w/ double-sided cabinets that demands its own zip code. A large walk-in pantry & custom built wood shelving and all appliances included complete

  Jonathan Lee RE/MAX Precision

  5219 Cherrywood Ln, Winterset, IA 50273
• 

  

  /33

  $225,000

  $10K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,701 Sq Ft

  204 S 8th Ave, Winterset, IA 50273

  Welcome home to this charming two-story home situated on a spacious corner lot! Offering 5 bedrooms and 2 bathrooms, there's plenty of room to spread out and make it your own. Inside, you'll find a comfortable blend of carpeting and laminate flooring that creates a warm and welcoming feel throughout. The attached garage offers space for two vehicles plus a dedicated workshop area, making it ideal

  Ashlee & Kyle Knickerbocker Keller Williams Realty GDM

  204 S 8th Ave, Winterset, IA 50273
• 

  

  /30

  $309,500

  $31K PRICE DROP

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

  423 E Jefferson St, Winterset, IA 50273

  Welcome home to this adorable 3-bedroom, 2-bath Arts & Crafts bungalow built in 1920, offering 1,913 sq ft of timeless charm and thoughtful updates. From the inviting covered porch and fenced front yard to the beautiful original details throughout, this home perfectly blends historic character with today’s conveniences. Step inside to find a warm and welcoming family room featuring wood beams, a

  Jennifer Stover Madison County Realty

  423 E Jefferson St, Winterset, IA 50273
• 

  

  /35

  $949,900

  • 3 Beds
  • 2.5 Baths
  • 3,210 Sq Ft

  1524 260th St, Winterset, IA 50273

  DREAMS DO COME TRUE! Take a look at this exquisite 2 story home on 15ac in beautiful MADISON COUNTY. The CRAFTSMANSHIP of this home is amazing, from the CUSTOM CABINETS, DOORS and COMMERCIAL EXHAUST VENT, all made on site, to the CUSTOM STEEL BACKSPLASH and BARN BOARDS from the old Homestead that was located on this acreage. The LARGE GRANITE BAR has a built-in beverage frig and seating for 8.

  Betsy Breeding Realty ONE Group Impact

  1524 260th St, Winterset, IA 50273
• 

  

  /34

  $249,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 866 Sq Ft

  715 N 3rd Ave, Winterset, IA 50273

  ** MOVE IN READY WITH ALL THE UPDATES ** This 4 bed 2 bath has been thoughtfully and skillfully updated and is ready for its new owners! Improvements include: All new interior paint. New/updated trim. All new Flooring. New lighting. New windows in 2025. Interior doors summer 2025. New siding approx 15 years ago with new paint summer 2025. New roof/sofit/facia approx 10 years. Furnace 3 years.

  Alyssa Tadlock Madison County Realty

  715 N 3rd Ave, Winterset, IA 50273
• 

  

  /31

  $215,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,148 Sq Ft

  215 E Filmore St, Winterset, IA 50273

  Just listed: Winterset modestly priced ranch-style home.This property features two bedrooms, one full bathroom, and a partial bath located off the laundry room. The home offers easy entry through an enclosed front porch with a closet.The interior includes a large open kitchen and dining area. All kitchen appliances are included. For outdoor living and dining, sliders from the kitchen lead

  

  Toni Tindle

  Covered Bridge Realty

  215 E Filmore St, Winterset, IA 50273
• 

  

  /29

  $299,000

  • 2 Beds
  • 1.5 Baths
  • 1,476 Sq Ft

  519 W Filmore St, Winterset, IA 50273

  Old-world charm meets modern living in this beautifully maintained and renovated two story home, situated on a corner lot with landscaped grounds. Rich original woodwork, abundant natural light, and timeless character create a warm and inviting atmosphere throughout.The fully renovated kitchen and bathroom blend classic style with modern luxury, featuring custom cabinetry, premium Café

  Kurt Clements ListWithFreedom.com Inc

  519 W Filmore St, Winterset, IA 50273
• 

  

  /35

  $900,000

  $69K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,982 Sq Ft

  2318 Saint Charles Rd, Winterset, IA 50273

  Escape to your own peaceful slice of heaven with this stunning acreage offering over 45 scenic acres of rolling countryside, abundant wildlife, and endless possibilities. Approximately 18 acres are enrolled in a tax-deferred forestry program, while additional acreage provides excellent hay ground potential and beautiful pasture areas ideal for horses or hobby farming. A large outbuilding offers

  Helen Turner Iowa Realty Mills Crossing

  2318 Saint Charles Rd, Winterset, IA 50273

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