Winterset, IA Homes for Sale under $300,000

/31
$259,000
- 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) 373-5687

609 E Filmore St, Winterset, IA 50273
Explore Winterset
/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
/4
$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) 230-0488

2212 Deer Run Ave, Winterset, IA 50273
/26
$205,000
- 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
/13
$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 home! 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

Alyssa Tadlock Madison County Realty

411 W Madison 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
$225,000
- 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
$220,000
- 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
/22
$249,900
- 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
/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
/33
$225,000
- 3 Beds
- 2 Baths
- 2,085 Sq Ft
705 S 2nd St, Winterset, IA 50273

Located in beautiful Winterset, IA, this well-maintained home offers over 2,000 square feet of comfortable living space. Featuring 3 bedrooms and 2 full bathrooms, the home includes a brand-new custom kitchen with updated cabinetry, perfect for everyday living and entertaining. Situated on a large lot with an oversized garage, there's plenty of room for storage, hobbies, and outdoor enjoyment. A

Kyle Kuhns RE/MAX Revolution

705 S 2nd St, Winterset, IA 50273
/12
$216,000
- 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
/12
$220,000
- 2 Beds
- 1 Bath
- 1,031 Sq Ft
405 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

405 W Madison 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
/23
$221,900
- 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
/29
$299,000
- 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
- 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
- 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
/35
$279,000
- 3 Beds
- 2.5 Baths
- 1,776 Sq Ft
513 E Jefferson St, Winterset, IA 50273

Motivated sellers! Welcome to this huge 3 bed, 3 bath home with a great, beautiful lot in the heart of Winterset (one of the BEST small towns in us)! What a GEM! One of lowest price per SF renovated homes on the market! Hardwood floors, original trim, large entryway, vaulted ceilings, oversized living room with beautiful windows, sunroom has all new windows & flooring for office, kid’s space or

Alison Frank Platinum Realty LLC

513 E Jefferson St, Winterset, IA 50273

Iowa Madison County Winterset

Home Trends in Winterset, IA

On average, homes in Winterset, IA sell after 74 days on the market compared to the national average of 54 days. The median sale price for homes in Winterset, IA over the last 12 months is $243,750, up 8% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$243,750

Median Single Family Sale Price

$262,500

Median 2 Bedroom Sale Price

$213,000

Median 1 Bedroom Sale Price

$217,000

Average Price Per Sq Ft

$190

Number of Homes for Sale

Last 12 months Home Sales

112

Months of Supply

2.70

Median List Price

$269,450

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 23 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

Winterset Land for Sale

Winterset Homes by Price

More About Living in Winterset

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage