Winterset, IA Homes for Sale under $300,000

• 

  

  

  /35

  $225,000

  $30K 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.

  

  Toni Tindle

  Covered Bridge Realty

  710 N 3rd Ave, Winterset, IA 50273
• Explore Winterset

• 

  

  

  /31

  $225,000

  • 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
• 

  

  

  /21

  $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
• 

  

  

  /29

  $190,000

  • 3 Beds
  • 1 Bath
  • 1,926 Sq Ft

  415 N 1st Ave, Winterset, IA 50273

  Just blocks from Winterset’s historic square, this 1.5-story home blends charm with everyday function. A wraparound porch (swing included) sets the tone before you even walk in. Inside, a bright living room with a cozy fireplace opens into an eat-in kitchen with white cabinetry, stainless appliances, and a walk-in pantry. All three bedrooms sit on the main level, along with a full bath and

  

  Darson Grantham

  Keller Williams Realty GDM

  415 N 1st Ave, 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
  • 7.68 Acres
  • $21,484 per Acre

  001 Rolling Green Ave, Winterset, IA 50273

  Build your dream home on 7.68 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.

  Angie Standlee Covered Bridges MHP

  1624 W Summit St Unit 122, Winterset, IA 50273
• 

  

  /33

  $235,000

  • 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

  Angie Standlee Covered Bridges MHP

  1624 W Summit St Unit 138, 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
• 

  

  /26

  $250,000

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  420 W Mills St, Winterset, IA 50273

  This well-maintained home offers a ton of space and a sprawling floor plan that sets it apart from your traditional split-level layout. A major highlight is the large, completely finished master suite situated privately above the garage. In total, the home features 4 bedrooms, 2 full bathrooms, and one half bathroom, along with its own dedicated laundry room. The kitchen includes a convenient bar

  Ian Sparks Homefront Real Estate, LLC

  420 W Mills St, Winterset, IA 50273
• 

  

  /7

  $160,000

  • Land
  • 3.32 Acres
  • $48,193 per Acre

  2211 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

  2211 Cedar Bridge Rd, 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
• 

  

  /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

  $229,900

  $20K 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
• 

  

  /9

  $44,900

  • 3 Beds
  • 2 Baths

  1624 W Summit St Unit 106, Winterset, IA 50273

  Discover affordable small-town living at its finest in this beautiful 3-bedroom, 2-bathroom home nestled in Winterset's peaceful Covered Bridges community! Step inside to find an impressively spacious living room and a large, welcoming kitchen perfect for family gatherings or entertaining friends. Offering unbeatable value with LVP throughout, Carpet in the bedrooms, freshly painted, steel

  Angie Standlee Covered Bridges MHP

  1624 W Summit St Unit 106, 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
• 

  /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
• 

  

  /16

  $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
• 

  

  /34

  $1

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  00 235th St, Winterset, IA 50273

  Madison County, Iowa Land Auction! Presenting the sale of 75.33 surveyed acres m/l of premium recreational land located just southwest of Winterset, Iowa, in Madison County. This unique offering presents an excellent opportunity to purchase quality recreational property, attractive building sites, and a rural acreage in one of Iowa's most desirable counties. The property will be offered in three

  Daran Becker Peoples Company

  00 235th St, 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

  $89,900

  • 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

  Angie Standlee Covered Bridges MHP

  1624 W Summit St Unit 135, 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
• 

  

  /23

  $290,000

  $30K 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
• 

  

  /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

  $270,000

  • 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
• 

  

  /7

  $140,000

  • Land
  • 5.36 Acres
  • $26,119 per Acre

  002 220th St, Winterset, IA 50273

  Build your dream home on 5.36 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
• 

  

  /34

  $239,000

  • 3 Beds
  • 2.5 Baths
  • 1,246 Sq Ft

  207 E Buchanan St, Winterset, IA 50273

  Now this is a home you'll want to show off! A historic Frame House in the heart of Winterset, fully renovated & remarkably designed. Huge curb appeal, mature trees, brand new front deck. Inside is a beautiful entry that leads to a stunning, expansive living room with original shiplap ceiling, tons of natural light. Gorgeous, grand dining room. The kitchen meets your needs & has tons of style. New

  Alison Frank Platinum Realty LLC

  207 E Buchanan St, Winterset, IA 50273
• 

  

  /7

  $149,000

  • Land
  • 2.93 Acres
  • $50,853 per Acre

  Lot 35 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 35 Limestone Ct, Winterset, IA 50273
• 

  

  /29

  $289,000

  $10K PRICE DROP

  • 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
• 

  

  /7

  $240,000

  $10K PRICE DROP

  • Land
  • 4.19 Acres
  • $57,279 per Acre

  Lot 17 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 17 114th Ct, Winterset, IA 50273
• 

  

  /7

  $220,000

  $55K PRICE DROP

  • Land
  • 4.22 Acres
  • $52,133 per Acre

  Lot 31 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 31 Limestone Ct, Winterset, IA 50273

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