Winterset, IA Homes for Sale under $300,000

/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
Explore Winterset
/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 over the sink window facing south, included

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

Chris Kew

RE/MAX Precision

(515) 531-5829

2212 Deer Run 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
/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
/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
/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
/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
/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
/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
/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
/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
/29
$205,000
- 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
$220,000
- 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
/22
$290,000
- 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
/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
/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
$260,000
- Land
- 3.14 Acres
- $82,803 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
/7
$240,000
- 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
/7
$250,000
- Land
- 3.75 Acres
- $66,667 per Acre
Lot 18 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 18 114th Ct, Winterset, IA 50273
/7
$220,000
- 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
/7
$250,000
- Land
- 3.33 Acres
- $75,075 per Acre
Lot 22 112th 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 22 112th Ct, Winterset, IA 50273
/7
$215,000
- Land
- 2.91 Acres
- $73,883 per Acre
Lot 26 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 26 114th Ct, Winterset, IA 50273
/7
$230,000
- Land
- 3.3 Acres
- $69,697 per Acre
Lot 29 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 29 Limestone Ct, Winterset, IA 50273
/7
$285,000
- Land
- 3.11 Acres
- $91,640 per Acre
Lot 15 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 15 114th Ct, Winterset, IA 50273
/7
$230,000
- Land
- 3.4 Acres
- $67,647 per Acre
Lot 28 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 28 Limestone Ct, Winterset, IA 50273

Iowa Madison County Winterset

Home Trends in Winterset, IA

On average, homes in Winterset, IA sell after 70 days on the market compared to the national average of 53 days. The median sale price for homes in Winterset, IA over the last 12 months is $243,500, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$243,500

Median Single Family Sale Price

$252,500

Median 2 Bedroom Sale Price

$220,000

Median 1 Bedroom Sale Price

$225,000

Average Price Per Sq Ft

$184

Number of Homes for Sale

Last 12 months Home Sales

115

Months of Supply

3.50

Median List Price

$265,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

How to Buy a Home How to Finance a Home How to Sell a Home

Browse a range of homes for sale under $300,000 in Winterset, offering accessible options for prospective buyers. With 27 listings available, there's a variety of affordable properties to explore, from charming starter homes to spacious family residences. These homes present an excellent opportunity to enter the housing market and secure a property that fits both your preferences and your budget in Winterset, IA.

Winterset Types of Homes for Sale

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