Are yards well-kept in Winterset, IA?

As of early 2026, 96% of users say yards are well-kept

Would people walk alone at night in Winterset, IA?

As of early 2026, 91% of users say people would walk alone at night

Is Winterset, IA dog-friendly?

As of early 2026, 85% of users say it's dog friendly

Do kids play outside in Winterset, IA?

As of early 2026, 84% of users say kids play outside

Is parking easy in Winterset, IA?

As of early 2026, 80% of users say parking is easy

Is Winterset, IA quiet?

As of early 2026, 76% of users say it's quiet

Are neighbors friendly in Winterset, IA?

As of early 2026, 75% of users say neighbors are friendly

Does Winterset, IA have sidewalks?

As of early 2026, 73% of users say there are sidewalks

Is Winterset, IA walkable to restaurants?

As of early 2026, 70% of users say it's walkable to restaurants

Does Winterset, IA show holiday spirit?

As of early 2026, 69% of users say there's holiday spirit

Are the streets well-lit in Winterset, IA?

As of early 2026, 68% of users say streets are well-lit

Is a car needed in Winterset, IA?

As of early 2026, 62% of users say car is needed

Do residents of Winterset, IA plan to stay at least 5 years?

As of early 2026, 59% of users say they plan to stay for at least 5 years

Is Winterset, IA walkable to grocery stores?

As of early 2026, 50% of users say it's walkable to grocery stores

Is there wildlife in Winterset, IA?

As of early 2026, 47% of users say there's wildlife

Are there community events in Winterset, IA?

As of early 2026, 41% of users say there are community events

OFF MARKET

309 E High St
Winterset, IA 50273

3 Beds
1 Bath
1,358 sqft

$134,600

Trulia Estimate

as of Jul 29, 2026

Est. Refi. Payment $945/mo*

Refinance Your Home

$134,600

Trulia Estimate

as of Jul 29, 2026

Est. Refi. Payment $945/mo*

Refinance Your Home

3 Beds

1 Bath

1,358 sqft

Local Information

Map ViewExplore the area around 309 E High St.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1900

Living Area

1,358 sqft

Price/Sqft

$99

Parking

Garage

About this House

Charming and Spacious! This turn of the century home features gorgeous hardwood flooring, original woodwork, a large living room and over 1300 sq ft. One bedroom on the main floor as well as a flexible dining room or office space. The two bedrooms upstairs have new carpeting and built-in storage. The mature maple and oak trees provide plenty of shade and the garage with attached shed would make a great workshop. This home is within walking distance to the town square and elementary school. Schedule your private showing today!

309 E High St, Winterset, IA 50273 is a 3 bedroom, 1 bathroom, 1,358 sqft single-family home built in 1900. It last sold for $78,500 on Apr 1, 2019. It is currently off market. The Trulia Estimate is $134,600, with a rent estimate of $1,409/month.

Home Details for 309 E High St

Interior Features
Heating & Cooling Heating: Forced Air, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 1.5Floors: Hardwood
Interior Details Number of Rooms: 6Types of Rooms: Dining Room
Appliances & Utilities Cable Ready

Exterior Features
Exterior Home Features Roof: AsphaltExterior: WoodFoundation Type: Stone
Parking & Garage GarageParking: Garage Detached

Property Information
Year Built Year Built: 1900
Property Type / Style Property Type: Single Family HomeArchitecture: A-frame

Lot Information
Lot Area: 9801 sqft

Price History for 309 E High St

Date	Price	Event	Source
04/01/2019	$78,500	Sold	DMMLS #574426
Recording Date 04/01/2019 County Transfer Tax N/A Total Transfer Tax N/A
03/09/2019	$84,900	Pending	Agent Provided

12/31/2018	$84,900	PriceChange	Agent Provided
Price Change $5,400 (7%)
09/07/2018	$79,500	Listed For Sale	N/A

07/22/2016	$55,000	Sold	DMMLS #519889
Recording Date 07/22/2016 County Transfer Tax N/A Total Transfer Tax N/A
06/28/2016	$57,900	Pending	Agent Provided

06/14/2016	$57,900	Listed For Sale	Agent Provided

Market trends in Winterset

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

8MoM

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Property Tax and Assessment

Year	2025
Tax	$1,958
Assessment	$119,100

Home facts updated by county records

Comparable Sales for 309 E High St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
117 S 5th St, Winterset, IA	0.17	Single-Family Home	$40,000	08/26/25	2	1	788
323 W Green St, Winterset, IA	0.51	Single-Family Home	$151,000	06/18/26	3	1	1,618

Home facts updated by county records

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $178,900
3 bd
1 ba
1,408 sqft
401 E Filmore St,
Winterset, IA 50273
OFF MARKET
Est. $276,400
4 bd
2 ba
1,218 sqft
519 N 4th St,
Winterset, IA 50273
FOR SALE
$335,000
3 bd
2 ba
1,913 sqft
423 E Jefferson St,
Winterset, IA 50273
Madison County Realty
OFF MARKET
Est. $164,800
4 bd
1.5 ba
2,018 sqft
415 E Jefferson St,
Winterset, IA 50273
Realty ONE Group Impact
OFF MARKET
Est. $165,300
2 bd
2 ba
1,575 sqft
411 E Jefferson St,
Winterset, IA 50273
OFF MARKET
Est. $248,100
4 bd
2.5 ba
2,016 sqft
401 E Jefferson St,
Winterset, IA 50273
Madison County Realty
OFF MARKET
Est. $236,800
2 bd
1 ba
808 sqft
411 E Filmore St,
Winterset, IA 50273
OFF MARKET
Est. $241,300
3 bd
2 ba
1,359 sqft
318 S 4th St,
Winterset, IA 50273
OFF MARKET
Est. $101,400
1 bd
1.5 ba
1,021 sqft
423 E Filmore St,
Winterset, IA 50273
OFF MARKET
Est. $200,500
3 bd
2 ba
1,417 sqft
801 S 5th Ave,
Winterset, IA 50273
OFF MARKET
Est. $110,800
3 bd
1 ba
957 sqft
804 S 4th Ave,
Winterset, IA 50273
OFF MARKET
Est. $249,200
3 bd
1 ba
1,248 sqft
906 S 5th Ave,
Winterset, IA 50273

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Additional Cost

Assigned Schools

These are the assigned schools for 309 E High St.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winterset

At least 21 Trulia users voted on each feature.

96 % Say yards are well-kept
91 % Say people would walk alone at night
85 % Say it's dog friendly
84 % Say kids play outside
80 % Say parking is easy
76 % Say it's quiet
75 % Say neighbors are friendly
73 % Say there are sidewalks
70 % Say it's walkable to restaurants
69 % Say there's holiday spirit
68 % Say streets are well-lit
62 % Say car is needed
59 % Say they plan to stay for at least 5 years
50 % Say it's walkable to grocery stores
47 % Say there's wildlife
41 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Mariah B.
Resident
6y ago
"Dislike: Not everyone keeps their dog on a leash Like: town is just big enough to get a few mile walk in, but small enough that you’re never far from home"
1
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Erin
Resident
7y ago
"Winterset always has a lot going on! Everything is close in town, we love living here. Small town, close to Des Moines, very convenient! "
1
Flag
Anna P
Resident
7y ago
"random kids run around in my yard when it's not winter, not good when you actually have a fence, they help themselves, and you can hear them outside your bathroom window sometimes. Other dog owners are great, just not responsible parents."
0
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Cnolte1410
Resident
7y ago
"Under 5 minutes via car. Would be an easy bike ride or walk. Most homeowners are considerate regarding snow and ice removal. City needs to work on snow removal from streets!"
0
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Cnolte1410
Resident
7y ago
"Nice family focused neighborhood. Community pool is within easy walking distance. Neighborhood is nice mix of different ages."
0
Flag
lindy g.
Resident
8y ago
"we call Winterset "Mayberry" since so many people are walking...some with their dogs. we experience no crime for the most part. very friendly neighbors."
2
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