Winterset, IA Homes for Sale under $300,000

• 

  

  

  /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
• Explore Winterset

• 

  

  

  /31

  $169,000

  • 3 Beds
  • 1 Bath
  • 1,523 Sq Ft

  118 N 5th St, Winterset, IA 50273

  Charm with economy! That's what this 5BR, 1 bath, 1.5 story home offers! Great natural light from the large east-facing picture window in the living room. There are 3 bedrooms on the main level, along with the full bath. The open carpeted stairway will lead you to the 2 non-conforming bedrooms (no closets) on the 2nd level. Easy-to-clean laminate flooring throughout main level. The main floor

  

  Toni Tindle

  Covered Bridge Realty

  118 N 5th St, 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
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /29

  $260,000

  $10K PRICE DROP

  • Land
  • 10.23 Acres
  • $25,415 per Acre

  2212 Deer Run Ave, Winterset, IA 50273

  Have you been looking for the perfect country spot to build your dream home? This 10 acre lot has all of the infrastructure already in place. It is build-ready! $50,000 has been invested in the property for a building pad, water and electric brought from the road to the build site, new driveway, etc. A future barndominium or walkout home will enjoy rolling countryside views for miles.

  Jeffrey Longman RE/MAX Precision

  2212 Deer Run Ave, Winterset, IA 50273
• 

  

  /7

  $165,000

  • Land
  • 7.26 Acres
  • $22,727 per Acre

  001 Rolling Green Ave, Winterset, IA 50273

  Build your dream home on 7.26 acres in scenic Madison County. Located just 20 minutes from West Des Moines and 2 miles south of Hwy 92, this beautiful building site offers rural water, electricity, and high-speed fiber internet at the road. Enjoy peaceful country living on a well-maintained gravel road with an easy commute to DSM.

  Jodi Broadbent Realty ONE Group Impact

  001 Rolling Green Ave, Winterset, IA 50273
• 

  

  /7

  $45,900

  • 3 Beds
  • 2 Baths

  1624 W Summit St Unit 122, Winterset, IA 50273

  Welcome home to this refreshed 3 bedroom, 2 bathroom home! Fresh paint throughout gives the home a clean, modern feel while the spacious layout offers comfort and functionality. The primary bedroom features its own private en suite bathroom, creating the perfect retreat at the end of the day. Cozy up by the fireplace in the living room and enjoy the inviting atmosphere this home has to offer.

  Mahayla Claiser Covered Bridges MHP

  1624 W Summit St Unit 122, 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
• 

  

  /8

  $53,900

  • 3 Beds
  • 2 Baths

  1624 W Summit St Unit 138, Winterset, IA 50273

  Lot 138 is an updated 3-bedroom, 2-bathroom home! Featuring all new LVP flooring throughout, this home offers a modern and low-maintenance living space perfect for everyday comfort. The kitchen is open concept with brand new countertops, along with a new stove and refrigerator to be installed! Fresh paint throughout the home adds a bright, clean feel in every room. The second bathroom has been

  Mahayla Claiser Covered Bridges MHP

  1624 W Summit St Unit 138, Winterset, IA 50273
• 

  

  /30

  $185,000

  • 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
• 

  

  /10

  $69,900

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft

  714 E Benton St, Winterset, IA 50273

  Tremendous potential in this cute little ranch home in the heart of Winterset. Sitting on a wonderful lot and brimming with potential. With a few basic cosmetics, this would be an excellent Investment property or starter home. Sold As Is.

  Ted Weaver RE/MAX Concepts

  714 E Benton St, Winterset, IA 50273
• 

  /2

  $69,000

  $6K PRICE DROP

  • Land
  • 3.45 Acres
  • $20,000 per Acre

  36 St, Winterset, IA 50273

  3.45 Acres – Bring Your Own Builder!LAKE LOT available in Covered Bridge Estates, a welcoming community with paved roads. Enjoy the feel of peaceful country living while still having quick, convenient access to the Des Moines metro. All information obtained from seller and public records.

  Rachel Eller Summerset Realty

  36 St, Winterset, IA 50273
• 

  

  /29

  $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,

  Tony Berry RE/MAX Concepts

  322 W Washington St, Winterset, IA 50273
• 

  

  /17

  $229,100

  • 3 Beds
  • 2 Baths
  • 1,245 Sq Ft

  59 E North St, Winterset, IA 50273

  Welcome home to this beautifully maintained 3-bedroom, 2-bath, 1.5-story home filled with charm and curb appeal! Step outside and enjoy the beautifully landscaped, fully fenced yard—perfect for relaxing, entertaining, pets, or play. The open patio with pergola creates a wonderful outdoor gathering space, while the newer storm shelter and storage shed add extra peace of mind and convenience. A

  Rachel Eller Summerset Realty

  59 E North St, Winterset, IA 50273
• 

  

  /7

  $160,000

  • Land
  • 3.27 Acres
  • $48,930 per Acre

  2323 Cedar Bridge Rd, Winterset, IA 50273

  Introducing Five Iron Farms - Madison County's newest acreage subdivision. Five Iron Farms offers the best of both world: located in the city limits with city services, but also situated on 3+acres surrounded by farm ground with great views of the countryside. Located on a hard surface road and just down the road from Lakeview Country Club. Bring your own builder. A good reference address to use

  Jennifer Stover Madison County Realty

  2323 Cedar Bridge Rd, Winterset, IA 50273
• 

  

  /7

  $170,000

  $45K PRICE DROP

  • Land
  • 3.76 Acres
  • $45,213 per Acre

  Lot 27 114th Ct, Winterset, IA 50273

  Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - 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

  Julie Baudler RE/MAX Concepts

  Lot 27 114th Ct, 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
• 

  

  /34

  $280,000

  • 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 holiday

  Kate Carlson Realty ONE Group Impact

  602 N 1st Ave, Winterset, IA 50273
• 

  

  /7

  $230,000

  • Land
  • 2.9 Acres
  • $79,310 per Acre

  Lot 30 Limestone Ct, Winterset, IA 50273

  Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - 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

  Julie Baudler RE/MAX Concepts

  Lot 30 Limestone Ct, Winterset, IA 50273
• 

  

  /7

  $194,000

  $5K PRICE INCREASE

  • Land
  • 2.88 Acres
  • $67,361 per Acre

  Lot 25 114th Ct, Winterset, IA 50273

  Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - 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

  Julie Baudler RE/MAX Concepts

  Lot 25 114th Ct, Winterset, IA 50273
• 

  

  /7

  $225,000

  $35K PRICE DROP

  • Land
  • 3.14 Acres
  • $71,656 per Acre

  Lot 14 114th Ct, Winterset, IA 50273

  Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - 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

  Julie Baudler RE/MAX Concepts

  Lot 14 114th Ct, 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

  $219,900

  $30K 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
• 

  

  /7

  $240,000

  $60K PRICE DROP

  • Land
  • 6.98 Acres
  • $34,384 per Acre

  Lot 16 114th Ct, Winterset, IA 50273

  Map takes you to the development, not the actual lot. Please look at website for exact location of lots www.scenicridgeiowa.com - 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

  Julie Baudler RE/MAX Concepts

  Lot 16 114th Ct, Winterset, IA 50273
• 

  

  /19

  $220,000

  $5K 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
• 

  /2

  $130,000

  • Land
  • 39,204 Sq Ft
  • $144,444 per Acre

  Lot 1 N 4th Ave, Winterset, IA 50273

  New Light Commercial Development. Lots will be ready to build upon in Spring 2025, Street will be in Fall 2024. All utilities to the lots. Great location on north side of Winterset w/ easy access to major highways. Listing agent has ownership in the property.

  Peter Corkrean Madison County Realty

  Lot 1 N 4th Ave, Winterset, IA 50273
• 

  

  /17

  $169,900

  $55K PRICE DROP

  • Land
  • 4.68 Acres
  • $36,303 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
• 

  

  /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
• 

  /2

  $185,000

  • Land
  • 1.14 Acres
  • $161,996 per Acre

  Lot 4 N 4th Ave, Winterset, IA 50273

  New Light Commercial Development. Lots will be ready to be built upon in Spring 2025, road will paved in Fall 2025. All utilities to the lots. Great location for easy access to major highways. Listing agent has ownership in the property.

  Peter Corkrean Madison County Realty

  Lot 4 N 4th Ave, Winterset, IA 50273
• 

  

  /33

  $210,000

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft

  209 W Jefferson St Unit 17, Winterset, IA 50273

  Experience elevated small-town living in this beautifully updated 3rd floor corner condo located just one block from the historic downtown square of Winterset. Unit 17 offers the rare combination of modern finishes, secure low-maintenance living, and walkable convenience with restaurants, shopping, banking, and the post office all nearby. This spacious 2 bedroom, 2 full bath condo features 1,065

  Kent Brant Exit Country Realty

  209 W Jefferson St Unit 17, Winterset, IA 50273
• 

  

  /35

  $210,000

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft

  209 W Jefferson St Unit 23, Winterset, IA 50273

  Experience elevated small-town living in this beautifully updated 3rd floor corner condo located just one block from the historic downtown square of Winterset. Unit 17 offers the rare combination of modern finishes, secure low-maintenance living, and walkable convenience with restaurants, shopping, banking, and the post office all nearby. This spacious 2 bedroom, 2 full bath condo features 1,065

  Kent Brant Exit Country Realty

  209 W Jefferson St Unit 23, Winterset, IA 50273
• 

  

  /12

  $87,900

  $2K PRICE DROP

  • 3 Beds
  • 2 Baths

  1624 W Summit St Unit 135, Winterset, IA 50273

  Welcome to this well-maintained newer 3-bedroom, 2-bathroom home offering modern comfort and style! The primary bedroom features a private en suite bathroom, creating the perfect retreat at the end of the day. Enjoy low-maintenance LVP flooring throughout the kitchen, living room, and bathrooms, with cozy carpet in all bedrooms for added comfort. The open living space provides a great layout for

  Mahayla Claiser Covered Bridges MHP

  1624 W Summit St Unit 135, Winterset, IA 50273
• 

  

  /23

  $239,900

  • 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
• 

  

  /7

  $250,000

  • Land
  • 5.1 Acres
  • $49,020 per Acre

  2269 205th Ln, Winterset, IA 50273

  Introducing Five Iron Farms - Madison County's newest acreage subdivision. Five Iron Farms offers the best of both world: located in the city limits with city services, but also situated on 3+acres surrounded by farm ground with great views of the countryside. Located on a hard surface road and just down the road from Lakeview Country Club. Bring your own builder. A good reference address to use

  Jennifer Stover Madison County Realty

  2269 205th Ln, Winterset, IA 50273
• 

  

  /18

  $175,000

  $24K PRICE DROP

  • Land
  • 7.14 Acres
  • $24,510 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
• 

  

  /32

  $265,000

  $5K 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
• 

  

  /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
• 

  

  /7

  $140,000

  • Land
  • 5.78 Acres
  • $24,221 per Acre

  002 220th St, Winterset, IA 50273

  Build your dream home on 5.78 acres in scenic Madison County. Located just 20 minutes from West Des Moines and 2 miles south of Hwy 92, this beautiful building site offers rural water, electricity, and high-speed fiber internet at the road. Enjoy peaceful country living on a well-maintained gravel road with an easy commute to DSM

  Jodi Broadbent Realty ONE Group Impact

  002 220th St, 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.

  Randall Henry Madison County Realty

  624 W Summit St, Winterset, IA 50273

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