Newest Homes for Sale in Winterset, IA

• 

  

  

  /35

  $375,000

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

  310 W Washington St, Winterset, IA 50273

  Welcome to 310 W. Washington, where this classic Craftsman blends character with modern conveniences. This home checks all of the boxes of style and function - with a formal dining room, inviting family and living rooms, a cozy 3 season porch, practical home office and an expansive deck. The kitchen features a built-in buffet/coffee bar between the kitchen and dining room, making entertaining a

  Jennifer Stover Madison County Realty

  310 W Washington St, Winterset, IA 50273
• Explore Winterset

• 

  

  

  /12

  $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

  (515) 882-4007

  118 N 5th St, Winterset, IA 50273
• 

  

  

  /22

  $330,875

  • Land
  • 26.47 Acres
  • $12,500 per Acre

  2378 Francesca Ave, Winterset, IA 50273

  Here is a very nice 26.47+/- acre property located 6 miles southwest of Winterset, Iowa in Madison County, Iowa. The property provided excellent building and recreational opportunities. The property consists of mostly mature hardwood timber. The north end of the property has an open area for a potential building site and or nice location for a shed. The timber has been well-maintained and is a

  Matt Skinner Iowa Land Company

  2378 Francesca Ave, Winterset, IA 50273
• 

  

  

  /35

  $225,000

  • 1 Bed
  • 2.5 Baths
  • 1,213 Sq Ft

  324 S 10th Ave, Winterset, IA 50273

  Ranch style Townhome on Winterset West side combines benefits of home ownership with low maintenance in a prime location. Large walk-in closet with window is conveniently located near the front door. Living room boasts a gas log fireplace as a classic feature. The kitchen has included appliances and abundant storage with two pantry cabinets and more. Dining area near kitchen leads to a bright 4

  

  Toni Tindle

  Covered Bridge Realty

  (515) 417-0598

  324 S 10th Ave, Winterset, IA 50273
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  /24

  $220,000

  • 2 Beds
  • 3 Baths
  • 1,213 Sq Ft

  827 W Fremont St, Winterset, IA 50273

  Just listed . . . . townhome in the West End Townhomes located off W Fremont Street in Winterset. E-Z access as you enter the quiet cul-de-sac with circle drive designed with room for additional parking. Two-bedroom two bath home with 1,213 square feet of finish on the main level. Large well-lit living room has gas log fireplace as a focal point. An adjacent walk-in coat closet with shelving is

  

  Toni Tindle

  Covered Bridge Realty

  (515) 575-2601

  827 W Fremont St, Winterset, IA 50273
• 

  

  /32

  $325,000

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

  1541 Nature Ct, Winterset, IA 50273

  Endless possibilities on nearly 5 acres of peaceful countryside! This 3-bedroom, 2-bath manufactured home sits on 4.98 acres off a private drive, offering beautiful views and plenty of room to enjoy country living your way. With no covenants or restrictions, you’re free to bring animals, build a dream home, add a shop, or simply enjoy the open space. The home features an open layout with updated

  Elizabeth Gordon Realty ONE Group Impact

  1541 Nature Ct, Winterset, IA 50273
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  /34

  $675,000

  • 3 Beds
  • 3.5 Baths
  • 3,298 Sq Ft

  2218 N John Wayne Dr, Winterset, IA 50273

  Welcome to this exceptional 3300 sq ft 3/4-bedroom, 4-bath brick ranch that perfectly balances privacy, convenience, and expansive living. Situated on 5+ acres just outside of town, this property offers the best of both worlds—peaceful seclusion with quick access to amenities and major highways. The home boasts a large open-concept living area anchored by a beautiful double-sided fireplace,

  Alyssa Tadlock Madison County Realty

  2218 N John Wayne Dr, Winterset, IA 50273
• 

  

  /31

  $215,000

  • 3 Beds
  • 1.5 Baths
  • 988 Sq Ft

  501 W Hutchings St, Winterset, IA 50273

  Welcome to this beautiful home in the heart of Winterset. This property features 3-beds, 1.5 baths, in almost 1,000 sq ft on the main level and a partially finished basement for extra storage or living space. Enjoy a nice-sized yard perfect for outdoor activities. The attached 1-car garage adds convenience year-round. Located within walking distance to the school.

  Krymsin Graf Iowa Realty Ankeny

  501 W Hutchings St, Winterset, IA 50273
• 

  

  /23

  $229,900

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

  114 S 14th Ave, Winterset, IA 50273

  Well-maintained 4-bedroom ranch on a corner lot in Winterset! This home offers convenient single-level living with a functional layout and plenty of natural light. The detached 2-car garage provides excellent storage and parking. Great location near the Winterset Aquatic Center, parks, and other community amenities. A wonderful opportunity to own a home in a desirable area of town!

  Rachel Eller Summerset Realty

  114 S 14th Ave, Winterset, IA 50273
• 

  

  /17

  $195,000

  • Land
  • 4.88 Acres
  • $39,959 per Acre

  4922 Cedar Ln, Winterset, IA 50273

  Looking for the perfect mix of privacy, space, and convenience? This stunning 4.88-acre lot at the end of a quiet cul-de-sac offers just that. Located on a paved road between West Des Moines and Winterset, this property features a beautiful blend of open grassland and mature timber, ideal for creating your custom retreat.There's room for it all: your dream home, an outbuilding, or even a

  Timothy Scheib Real Broker, LLC

  4922 Cedar Ln, Winterset, IA 50273
• 

  

  /15

  $145,000

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

  207 E Buchanan St, Winterset, IA 50273

  Discover this inviting frame home located near the Winterset Square. The main level features a generous sized living room with an enclosed entryway, a full bathroom, and a main floor bedroom. The kitchen opens to the dining area, creating a warm and functional space for everyday living. Upstairs, you'll find two additional bedrooms, offering flexibility for family, guests, or a home office. The

  

  Toni Tindle

  Covered Bridge Realty

  (515) 493-7698

  207 E Buchanan St, Winterset, IA 50273
• 

  

  /21

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,174 Sq Ft

  110 E Grade St, Winterset, IA 50273

  Step into this beautifully remodeled and charming single-story home, thoughtfully designed to combine comfort and modern living. This inviting 3-bedroom, 2-bath residence showcases a spacious eat in kitchen (appliances included) and an airy, naturally lit living room with vaulted ceiling that creates a welcoming atmosphere throughout. This property offers both comfort and function. The primary

  Sarah Cowman Homefront Real Estate, LLC

  110 E Grade St, Winterset, IA 50273
• 

  

  /27

  $499,000

  • 4 Beds
  • 3 Baths
  • 1,404 Sq Ft

  2155 148th St, Winterset, IA 50273

  Tranquil Country Living Just Minutes from the City Experience peaceful country living with city convenience on this stunning 4.19-acre corner lot innorth-central Madison County—just 20 miles west of Jordan Creek Mall and 7 miles from I-80.A tree-lined drive welcomes you to this serene property featuring a 36x34 metal outbuilding withpower, concrete floors, and 14-ft overhead

  

  Cindy Miller

  Keller Williams Realty GDM

  (515) 493-7953

  2155 148th St, Winterset, IA 50273
• 

  

  /9

  $272,875

  • Land
  • 29.49 Acres
  • $9,253 per Acre

  Pioneer Ave, Winterset, IA 50273

  Discover this beautiful small-acreage in Madison County, located less than 10 minutes from Winterset and just 30 minutes from West Des Moines. Situated less than a mile from pavement, this farm offers a perfect blend of tillable ground and open pasture. Approximately 8 acres are currently in a corn and soybean rotation, with the remaining balance used for pasture and recreation. A small creek

  KILOTERRA KILOTERRA KILOTERRA | Land Sales & Auctions

  Pioneer Ave, Winterset, IA 50273
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  /37

  $495,000

  • Land
  • 60 Acres
  • $8,250 per Acre

  2340 Holliwell Bridge Rd, Winterset, IA 50273

  KILOTERRA is proud to present this diverse 60-acre property in Madison County, offering a rare blend of productive land, prime hunting, and build potential. Located less than 10 minutes from Winterset and just 30 minutes from West Des Moines, this property delivers the ideal balance of rural seclusion and modern convenience. Access is available from the east, west, and south sides, with pavement

  KILOTERRA KILOTERRA KILOTERRA | Land Sales & Auctions

  2340 Holliwell Bridge Rd, Winterset, IA 50273
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  /35

  $650,000

  • 3 Beds
  • 3 Baths
  • 2,064 Sq Ft

  1706 Mueller Ct, Winterset, IA 50273

  Nature lover’s dream! Tucked away on 8.1 breathtaking acres, this property offers peace, privacy, and a front-row seat to nature’s beauty. Mature trees surround the home, creating a serene setting filled with wildlife and seasonal color. Step inside to an open-concept main level designed to bring the outdoors in, featuring a spacious eat-in kitchen with walk-in pantry and large windows framing

  Ashlee & Kyle Knickerbocker Keller Williams Realty GDM

  1706 Mueller Ct, Winterset, IA 50273
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  /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
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  /28

  $924,900

  • 4 Beds
  • 2.5 Baths
  • 1,534 Sq Ft

  2176 148th St, Winterset, IA 50273

  Discover 17.9 Acres of Updated Country Living. Welcome to your dream acreage! This beautifully updated home sits on 17.9 acres of rolling countryside with a private pond, woods, and multiple outbuildings. Inside, the main level has been completely renovated with a brand-new kitchen featuring quartz countertops, sleek cabinetry, stainless appliances, and an open floor plan filled with natural

  Jason Russell Realty ONE Group Impact

  2176 148th St, Winterset, IA 50273
• 

  

  /35

  $1,385,000

  • 5 Beds
  • 5 Baths
  • 4,032 Sq Ft

  1890 Hogback Bridge Rd, Winterset, IA 50273

  Rare 30-acre M/L retreat in Madison County Iowa with a 4,000+ sq. ft. custom home. Incredible views of the countryside teeming with wildlife including white-tailed deer and turkey. Main level features gourmet kitchen with 2 dishwashers & walk-in pantry, spacious living areas, and a primary suite with sitting room, spa bath, huge walk-in closet & laundry. Upstairs offers loft with wet bar, 4

  Lenchen Raeside RE/MAX Concepts

  1890 Hogback Bridge Rd, Winterset, IA 50273
• 

  

  /29

  $360,000

  • 5 Beds
  • 4 Baths
  • 2,110 Sq Ft

  309 N 15th Ave, Winterset, IA 50273

  Don’t miss your chance to own this beautifully appointed 2-story home tucked away on a quiet street. From the moment you arrive, the inviting front porch sets the tone—perfect for sipping your morning coffee or unwinding with a sunset view. Step inside to an open-concept layout designed for gathering, with seamless flow from the spacious living areas to the patio, ideal for evening

  Sarah Cowman Homefront Real Estate, LLC

  309 N 15th Ave, Winterset, IA 50273
• 

  

  /18

  $249,900

  • 4 Beds
  • 2 Baths
  • 1,270 Sq Ft

  1413 W Washington St, Winterset, IA 50273

  Move-in ready and beautifully maintained, this 4-bedroom ranch offers easy single-level living with an inviting open floor plan. A rare oversized 3-car garage with additional storage is a dream for car enthusiasts or hobbyists, and the deck off the kitchen provides the perfect backdrop for outdoor dining and entertaining!

  Sarah Cowman Homefront Real Estate, LLC

  1413 W Washington St, Winterset, IA 50273
• 

  

  /30

  $499,900

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

  400 N 14th Ave, Winterset, IA 50273

  This immaculate 4-bedroom, 2-bath ranch home perfectly blends modern comfort with timeless style. Built in 2013 and exceptionally cared for, every detail radiates warmth, quality, and convenience. Step inside to an inviting open layout highlighted floor-to-ceiling stone fireplace—a stunning centerpiece for cozy evenings or lively gatherings with family and friends. The beautiful kitchen is both

  Sarah Cowman Homefront Real Estate, LLC

  400 N 14th Ave, Winterset, IA 50273
• 

  

  /23

  $274,900

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft

  303 E Court Ave, Winterset, IA 50273

  Welcome to one of the charming historical homes in Winterset. Walking through the front entrance, visitors are greeted with natural light spilling across the hardwood floors. As they enter the kitchen, the openness is easily noticeable making it a perfect place to host or have family dinners. The living room has charming built-ins which adds to the cozy feel. The laundry area is located on the

  Tamra Yeager Pro Team Realty

  303 E Court Ave, Winterset, IA 50273
• 

  

  /14

  $140,000

  • Land
  • 3.67 Acres
  • $38,147 per Acre

  2228 Holliwell Valley Ct, Winterset, IA 50273

  Picture your dream home nestled on 3.67 acres in the heart of Madison County. This flat, buildable acreage is framed by mature trees and rolling valleys, creating a private country retreat. With utilities available at the road and multiple sites to choose from, you can design the perfect layout for your new home. Just a short drive from Winterset and steps away from the Holliwell Valley Covered

  Misty Darling BH&G Real Estate Innovations

  2228 Holliwell Valley Ct, Winterset, IA 50273
• 

  

  /35

  $540,500

  • Land
  • 23 Acres
  • $23,500 per Acre

  2571 250th Ln, Winterset, IA 50273

  Stunning Executive Building site located just south of Winterset on a dead-end road. If you have been dreaming of a country escape, this is something you need to consider. Approximately 23 acres to be surveyed off will include clean timber, spring-fed creek with well possibilities, wild flowers, limestone ledges, nice rolling pasture, and a stocked pond. Stunning views and wildlife galore!

  Sarah Cowman Homefront Real Estate, LLC

  2571 250th Ln, Winterset, IA 50273
• 

  

  /28

  $369,900

  • 4 Beds
  • 2.5 Baths
  • 1,333 Sq Ft

  215 W Buchanan St, Winterset, IA 50273

  Completely Renovated Winterset Gem — Modern Style Meets Small-Town Charm! This 4-bedroom, 3-bath home (1,333 sq ft above grade + 409 sq ft finished basement) is in the heart of Winterset — steps from parks, schools, and the historic town square. Enjoy everything Winterset offers, including the John Wayne Birthplace & Museum, the famous Covered Bridges of Madison County, and year-round festivals.

  Elizabeth Gordon Realty ONE Group Impact

  215 W Buchanan St, Winterset, IA 50273
• 

  

  /31

  $284,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  516 S 8th Ave, Winterset, IA 50273

  Step into history without the hassle! Built in 1890 and recently renovated, this 4-bedroom, 2-bath home offers the character you love with the updates you need. Sunlight pours through abundant windows, filling the spacious layout and large kitchen. Situated on nearly a half-acre (.418) lot right in town, you’ll have plenty of room to spread out, just minutes from Main Street and the birthplace of

  Tiffany Marcum The American Real Estate Co.

  516 S 8th Ave, Winterset, IA 50273
• 

  

  /23

  $145,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  516 W Summit St, Winterset, IA 50273

  Are you looking for a house with a LARGE YARD, close to SCHOOLS and WINTERSET TOWN SQUARE.Come take a look at this well-maintained ranch, on a big lot, in the beautiful town of Winterset! The three nice sized bedrooms also have great closet space. You will also like the open kitchen/dining area, with plenty of natural light, that leads out to the NEW LARGE DECK, perfect for morning coffee and

  Betsy Breeding Realty ONE Group Impact

  516 W Summit St, Winterset, IA 50273
• 

  

  /35

  $226,900

  • 3 Beds
  • 1.5 Baths
  • 958 Sq Ft

  513 W Hutchings St, Winterset, IA 50273

  Step into this beautifully remodeled 2025 home complete with 3 bedrooms and 1.5 bathrooms. Thoughtfully updated throughout, this residence includes new sheet rock and fresh paint, new LVP flooring, new central air system and duct work, upgraded plumbing and electrical and all new windows. Lage kitchen features custom Amish-built cabinetry, quartz countertops and just around the corner a main

  

  Toni Tindle

  Covered Bridge Realty

  (515) 481-5094

  513 W Hutchings St, Winterset, IA 50273
• 

  

  /34

  $650,000

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

  719 E Washington St, Winterset, IA 50273

  If the "Wow Factor" is what you are hoping for in a home, this one is a must-see! This home was gutted down to the studs and completely rebuilt, so it is just like brand new! Walk in the front door, and you will love all the natural light as you enter the living room with a cozy gas fireplace. The large dining area adjoins the gorgeous kitchen with tons of cabinets and countertop space. There is

  Sarah Cowman Homefront Real Estate, LLC

  719 E Washington St, Winterset, IA 50273
• 

  

  /35

  $375,000

  • 4 Beds
  • 2 Baths
  • 2,724 Sq Ft

  615 N 1st Ave, Winterset, IA 50273

  This beautifully remodeled residence combines timeless charm with modern comfort. Step inside to discover hardwood floors and a striking, gracefully designed staircase that sets the tone for the entire home. The inviting front porch offers the perfect spot to welcome guests or enjoy peaceful evenings outdoors. Featuring four generously sized bedrooms plus a bonus room, and a full bath on each

  Sarah Cowman Homefront Real Estate, LLC

  615 N 1st Ave, Winterset, IA 50273
• 

  

  /26

  $404,900

  • 4 Beds
  • 3.5 Baths
  • 1,710 Sq Ft

  1011 N 14th Ave, Winterset, IA 50273

  Discover your own slice of heaven right in town! This inviting two-story home is set in a friendly neighborhood where there's plenty of room to play and grow. The thoughtful layout makes the most of every square foot, creating spaces that work well for everyday life.The main level welcomes you with a handy drop zone, half bath, and a office with French doors. The open kitchen and family room

  Michelle Hanson RE/MAX Concepts

  1011 N 14th Ave, Winterset, IA 50273
• 

  

  /23

  $309,900

  • 3 Beds
  • 1.5 Baths
  • 2,130 Sq Ft

  721 W Court Ave, Winterset, IA 50273

  Don't miss the opportunity to own this home on historical Court Avenue! You will love sitting on the wraparound porch for your morning coffee or just some time to relax. Upon entering the home, you will be impressed with the beautiful details of the open staircase. The first floor has a large living, family and dining rooms, 1/2 bath and kitchen. The hardwood floors and the woodwork are original

  Larry Corkrean Madison County Realty

  721 W Court Ave, Winterset, IA 50273
• 

  

  /27

  $247,900

  • 3 Beds
  • 2 Baths
  • 1,106 Sq Ft

  316 E Jefferson St, Winterset, IA 50273

  Charming Victorian that has been fully renovated. The living room has ten-foot ceilings, beautiful chandeliers, and a gas fireplace. In the main bedroom, there is a unique stained glass window. Walking into the kitchen, you are greeted with quartz countertops and custom cabinets, which adds a modern touch. All the appliances are 2-3 years old. Washer/dryer hookups are in the basement along with a

  Tamra Yeager Pro Team Realty

  316 E Jefferson St, Winterset, IA 50273
• 

  

  /35

  $335,000

  • 4 Beds
  • 2 Baths
  • 1,912 Sq Ft

  59 E Benton St, Winterset, IA 50273

  Step inside this well-loved home that blends timeless character with modern updates—ready for its next owner to make it their own. The home’s original woodwork, in excellent condition, adds warmth and charm throughout. Enjoy relaxing mornings with coffee or peaceful evenings with dinner on the inviting front porch. Inside, you’ll find a spacious living room that flows seamlessly into a formal

  Sarah Cowman Homefront Real Estate, LLC

  59 E Benton St, Winterset, IA 50273
• 

  

  /16

  $145,000

  • Land
  • 3.49 Acres
  • $41,547 per Acre

  Lot 7 114th Ct, Winterset, IA 50273

  Build your luxury retreat on this 3.5-acre Website for the development is: Scenic Ridge lot,offering sweeping views of Madison County’s rolling hills at the gateway to the Covered Bridge Scenic Byway.Enjoy upscale living with premier shopping, dining, and entertainment at Jordan Creek and KeeTown less than 20 minutes away.

  Latrice Brauckman Realty ONE Group Impact

  Lot 7 114th Ct, Winterset, IA 50273
• 

  /2

  $70,500

  • Land
  • 3.45 Acres
  • $20,435 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
• 

  

  /20

  $127,900

  • Land
  • 4.15 Acres
  • $30,819 per Acre

  TBD 176th Ct, Winterset, IA 50273

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

  Colin Ortmeier Kiloterra

  TBD 176th Ct, Winterset, IA 50273
• 

  

  /9

  $130,000

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

  0000 Saint Charles Rd, Winterset, IA 50273

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

  Katie Bloom LPT Realty, LLC

  0000 Saint Charles Rd, Winterset, IA 50273
• 

  

  /11

  $655,384

  • Land
  • 50.51 Acres
  • $12,975 per Acre

  0 Millstream Ct Unit 24336276, Winterset, IA 50273

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

  Andrew Zellmer Peoples Company

  0 Millstream Ct Unit 24336276, Winterset, IA 50273

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