Saint Charles, IA Homes for Sale

• 

  

  

  /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
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  /35

  $375,000

  $99K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,389 Sq Ft

  1913 N 1st St, Winterset, IA 50273

  Hard to find home on this parcel just N of Winterset 4-way intersection of Hwy 92 & 169. This home has 3BR's & 3 baths sitting proudly on nearly 1 acre. Kitchen has had a complete remodel including adding a convenient island & farm sink. Master/BR on 1st floor has large walk-in closet, & tiled walk-in shower. Main floor laundry off the kitchen. Other features on the 1st level include a formal

  

  Toni Tindle

  Covered Bridge Realty

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

  $320,000

  $5K PRICE DROP

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

  511 W Washington St, Winterset, IA 50273

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

  

  Toni Tindle

  Covered Bridge Realty

  511 W Washington 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
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  /24

  $179,000

  • 2 Beds
  • 1.5 Baths
  • 1,230 Sq Ft

  1624 S 4th Ave, Winterset, IA 50273

  Thia 1.5 story home layout features two bedrooms and a bath on each floor. It is located just south of Winterset high school on South 4th Ave in Winterset. The main floor includes a formal dining room off the kitchen with included appliances. Large living room facing east with foyer off the front entrance and staircase leading to second floor. Full bath on the main floor includes closet and

  

  Toni Tindle

  Covered Bridge Realty

  1624 S 4th Ave, Winterset, IA 50273
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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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  /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
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  /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
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  /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
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  /34

  $549,999

  $45K PRICE DROP

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

  505 E Court Ave, Winterset, IA 50273

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

  Sarah Cowman Homefront Real Estate, LLC

  505 E Court Ave, Winterset, IA 50273
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  /35

  $329,900

  $20K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 1,800 Sq Ft

  117 E North St, Winterset, IA 50273

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

  Lisa Davis RE/MAX Precision

  117 E North St, Winterset, IA 50273
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  /30

  $309,500

  $31K PRICE DROP

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

  423 E Jefferson St, Winterset, IA 50273

  ****Seller has taken a new job with a long commute. They are motivated to sell before winter***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

  Jennifer Stover Madison County Realty

  423 E Jefferson St, Winterset, IA 50273
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  /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
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  /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
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  /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
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  /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

  $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
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  /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
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  /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
• 

  

  /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
• 

  /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
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  /35

  $315,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,470 Sq Ft

  1405 W Jefferson St, Winterset, IA 50273

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

  Matt Law RE/MAX Precision

  1405 W Jefferson St, Winterset, IA 50273
• 

  

  /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

  $450,000

  • Land
  • 30 Acres
  • $15,000 per Acre

  RR Scott Township None, Winterset, IA 50222

  A great opportunity to add to your existing operation or the perfect acreage to start a small farm, a nice building site or weekend gateway. This is a highly productive farm, all tillable with a CSR 2 rating of 83.

  Patrick Corkrean Madison County Realty

  RR Scott Township None, Winterset, IA 50222
• 

  /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
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  /34

  $579,900

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,432 Sq Ft

  719 E Washington St, Winterset, IA 50273

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

  Sarah Cowman Homefront Real Estate, LLC

  719 E Washington St, Winterset, IA 50273
• 

  

  /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
• 

  

  /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

  $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
• 

  

  /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

Showing Results 1 - 40, Page 1 of 2