32

Winterset, IA Homes for Sale under $300,000

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  • /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

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 481-5094

    513 W Hutchings St, Winterset, IA 50273
  • /28

    $274,000

    • 4 Beds
    • 2 Baths
    • 1,104 Sq Ft

    609 E Filmore St, Winterset, IA 50273

    Recently updated ranch style home with 4 bedrooms and 2 baths. Interior includes three BR’s on the main floor, living room, and kitchen just off attached one car garage. One bedroom on the main level would also make a perfect office space and was previously used as a sewing room. All bedrooms have generous sized closets. Updated kitchen with bright south facing over the sink window, included

    Agent Photo

    Toni Tindle

    Covered Bridge Realty

    (515) 495-5285

    609 E Filmore St, Winterset, IA 50273
  • /6

    $275,000

    • Land
    • 10.23 Acres
    • $26,882 per Acre

    2212 Deer Run Ave, Winterset, IA 50273

    Don't miss this rare opportunity to own 10 acres m/l of picturesque countryside just 8 miles west of Winterset, situated on a hard surface road and a prime corner lot. This walkout lot is ready for your dream home with rural water, electricity, and a driveway already added, saving you the time and expense of major improvements. The gently rolling terrain offers stunning views and the perfect

    Agent Photo

    Chris Kew

    RE/MAX Precision

    (515) 531-5829

    2212 Deer Run Ave, Winterset, IA 50273
  • /29

    $260,000

    • 3 Beds
    • 2.5 Baths
    • 1,560 Sq Ft

    120 S 8th Ave, Winterset, IA 50273

    Opportunity knocks on this ready-to-renovate 3-bed 2 and 1/2 bath ranch home. This has one of the coolest back yards in town! Professionally landscaped with numerous flowers, plants, bushes, and trees with your very own pond with a cool shed area. The house has a great layout with a large living room, very spacious kitchen with plenty of cabinets and countertop space, a large dining area, 3

    Sarah Cowman Homefront Real Estate, LLC

    120 S 8th Ave, Winterset, IA 50273
  • /18

    $260,000

    • 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
  • /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
  • /25

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft

    722 W Mills St, Winterset, IA 50273

    Beautifully maintained 3-bedroom, 2-bath ranch showcasing an inviting open floor plan with dining area. The partially finished basement includes a comfortable family room with an egress window, perfect for entertaining or relaxing. Step outside to a private, fenced backyard featuring a charming deck that offers a peaceful view of the yard—ideal for gatherings or quiet evenings at home.

    Sarah Cowman Homefront Real Estate, LLC

    722 W Mills St, Winterset, IA 50273
  • /31

    $314,000

    • 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
  • /31

    $299,000

    • 4 Beds
    • 1.5 Baths
    • 1,880 Sq Ft

    804 N 4th Ave, Winterset, IA 50273

    Welcome to a truly extraordinary home where timeless craftsmanship, modern luxury, and stunningnatural beauty come together in perfect harmony. Rarely does a property offer such a unique blend of old-world artisan detail and contemporary design, all set against the backdrop of gardens so exquisite! From the moment you arrive, the lush landscaping captures your attention, showcasing a level of

    Sarah Cowman Homefront Real Estate, LLC

    804 N 4th Ave, Winterset, IA 50273
  • /22

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    410 N 6th St, Winterset, IA 50273

    Pride of ownership in this spacious home! 3 bedrooms, 2 baths, over 2,000 sf finished space and a huge backyard. Adorable kitchen with stainless steel appliances. Refrigerator is less than 1 year old. Large dining area with sliding door that leads to the deck/backyard. Great set up for the primary bedroom with access to the bathroom/laundry room. All 3 bedrooms are on the 1st floor. The lower

    Jennifer Stover Madison County Realty

    410 N 6th St, Winterset, IA 50273
  • /21

    $205,000

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft

    315 S 5th Ave, Winterset, IA 50273

    Charming Brick Home with Bonus Space! This well-kept 2 bedroom, 2 bath brick home offers both comfort and versatility. Inside, you’ll find a spacious layout with a bonus room that could easily serve as a 3rd bedroom, home office, or hobby space. Recent updates include a newer roof and AC, giving you peace of mind for years to come. The exterior features a fenced-in yard, perfect for pets, kids,

    Dustin Crawford Iowa Home & Land Realty

    315 S 5th Ave, Winterset, IA 50273
  • /11

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,996 Sq Ft

    2366 Holliwell Bridge Rd, Winterset, IA 50273

    3 Bedroom - 2 Bath mobile home with a 780 Sq Ft family room added! Located on 6 acres more or less! Property is a combination of Timber and open grass. There is a building pad ready for construction and owners have planted 60 new trees in this area. Property has well that was drilled new in 2003. There is rural water located across from the house. New shingles in 2022, septic tank was new

    Betty Craig Saylor Realty

    2366 Holliwell Bridge Rd, Winterset, IA 50273
  • /27

    $210,000

    • 2 Beds
    • 2 Baths
    • 1,050 Sq Ft

    202 S 7th Ave, Winterset, IA 50273

    Full of character and charm, this home sits on a desirable corner lot in the heart of Winterset Step inside to bright living spaces with new flooring throughout. The functional kitchen features ample storage and prep space and opens to the dining room. An inviting 3 season room steps from the living room and adjoined to the garage offers the perfect bonus space for entertaining or quiet mornings.

    Tiffany Ehler Boutique Real Estate

    202 S 7th 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
  • /29

    $212,000

    • 3 Beds
    • 2 Baths
    • 1,452 Sq Ft

    66 E High St, Winterset, IA 50273

    Charming and fully updated 1.5 story home on a large corner lot in historic Winterset--roughly 30 minutes from the Des Moines metro! This 3-bed, 2-bath home features a spacious living room and a wrap-around layout that flows seamlessly from the living area to the updated kitchen with newer stainless steel appliances, and into the dining space. Stylish LVP flooring throughout the main level adds

    Cameron Campos RE/MAX Concepts

    66 E High St, Winterset, IA 50273
  • /14

    $227,500

    • 3 Beds
    • 1.5 Baths
    • 912 Sq Ft

    1021 W South St, Winterset, IA 50273

    Come enjoy small town living in Winterset in this adorable 3 bedroom ranch home! The spacious living area has tons of natural light with the large windows and beautiful hardwood floors. Find three bedrooms and a full bath on the main floor, as well as the farmhouse style kitchen featuring white subway tile backsplash and white cabinets. The lower level features an extra living space, half bath,

    Jenna Carney Keller Williams Realty GDM

    1021 W South St, Winterset, IA 50273
  • /10

    $299,000

    • Land
    • 10 Acres
    • $29,900 per Acre

    TBD Iowa 92, Winterset, IA 50273

    Build Your Dream Home on this Scenic 10-Acre Parcel!Located just off paved Highway 92 and only 25 minutes from the Des Moines metro, this beautiful ±10 acre lot offers the perfect mix of convenience and peaceful country living. With scenic views, open space, and rural water and electric at the road, it’s an ideal setting for your future home, hobby farm, or weekend retreat.Plenty of

    Rachel Eller Summerset Realty

    TBD Iowa 92, Winterset, IA 50273
  • /32

    $287,500

    • 3 Beds
    • 2 Baths
    • 1,741 Sq Ft

    620 W Filmore St, Winterset, IA 50273

    **Available now for quick possesion!!**Charming Ranch with modern Updates on a Quiet Street.Welcome to this beautifully updated home nestled on a peaceful street, perfect for those seeking both comfort and convenience. Step onto the quaint front porch and into a home that blends cozy charm with modern finishes throughout.This spacious home features a large primary bedroom with

    Alyssa Tadlock Madison County Realty

    620 W Filmore St, Winterset, IA 50273
  • /9

    $216,000

    • 2 Beds
    • 1 Bath
    • 1,031 Sq Ft

    413 E 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

    413 E Madison St, Winterset, IA 50273
  • /8

    $220,000

    • 2 Beds
    • 1 Bath
    • 1,031 Sq Ft

    411 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 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 in bedrooms and a

    Alyssa Tadlock Madison County Realty

    411 W Madison St, Winterset, IA 50273
  • /7

    $215,000

    • Land
    • 2.91 Acres
    • $73,883 per Acre

    Lot 26 114th Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 26 114th Ct, Winterset, IA 50273
  • /7

    $230,000

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

    Lot 30 Limestone Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 30 Limestone Ct, Winterset, IA 50273
  • /7

    $220,000

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

    Lot 31 Limestone Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 31 Limestone Ct, Winterset, IA 50273
  • /7

    $230,000

    • Land
    • 3.4 Acres
    • $67,647 per Acre

    Lot 28 Limestone Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 28 Limestone Ct, Winterset, IA 50273
  • /7

    $230,000

    • Land
    • 3.3 Acres
    • $69,697 per Acre

    Lot 29 Limestone Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 29 Limestone Ct, Winterset, IA 50273
  • /7

    $250,000

    • Land
    • 3.33 Acres
    • $75,075 per Acre

    Lot 22 112th Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 22 112th Ct, Winterset, IA 50273
  • /7

    $250,000

    • Land
    • 3.75 Acres
    • $66,667 per Acre

    Lot 18 114th Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 18 114th Ct, Winterset, IA 50273
  • /7

    $240,000

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

    Lot 16 114th Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 16 114th Ct, Winterset, IA 50273
  • /7

    $285,000

    • Land
    • 3.11 Acres
    • $91,640 per Acre

    Lot 15 114th Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 15 114th Ct, Winterset, IA 50273
  • /7

    $260,000

    • Land
    • 3.14 Acres
    • $82,803 per Acre

    Lot 14 114th Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 14 114th Ct, Winterset, IA 50273
  • /7

    $208,000

    • Land
    • 3.08 Acres
    • $67,532 per Acre

    Lot 13 114th Ct, Winterset, IA 50273

    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 garden, maybe have some chickens? Lead a sustainable life near the city? Your search is over! Scenic Ridge is all of those things and

    Julie Baudler RE/MAX Concepts

    Lot 13 114th Ct, Winterset, IA 50273
  • /5

    $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. Firve Iron Farms offer the best of both worlds: located in the city limits with city services, but also situated on 5 acres surrounded by farm ground with great views of the countryside. Located on a hard surface road and just down the road from Lakeview County Club. Bring your own builder. A good reference address to us

    Jennifer Stover Madison County Realty

    2269 205th Ln, Winterset, IA 50273

Home Trends in Winterset, IA

Housing Trends

Median Sale Price
$240,000
Median Single Family Sale Price
$255,000
Median 2 Bedroom Sale Price
$216,000
Average Price Per Sq Ft
$184
Number of Homes for Sale
41
Last 12 months Home Sales
115
Months of Supply
4.30
Median List Price
$265,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
2%
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