w1443 Roosevelt Rd, Oconomowoc, WI 53066

Listed by Jeremy Metzger • Midwest Realty Group, LLC. Bought with Shorewest Realtors, Inc.

Off market dec 2012 for $270K

$1,030,554

•

4,003

sq ft

w1443 Roosevelt Rd, Oconomowoc, WI 53066

About this home

Public Remarks: Beautiful newer home just waiting for your finishing ideas! Located on over 21 acres in rural Ashippun, enjoy the country views including an amazing view of Holy Hill! Horses welcome, includes an unfinished guesthouse that needs municipal approval to remain! The seller has directed that all offers on this listing be made using the HomePath online offer system at the HomePath website.

Single-familyProperty Type

2009Year Built

$257Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Jeremy Metzger • Midwest Realty Group, LLC

Bought with Elizabeth Curro • Shorewest Realtors, Inc.

Redfin checked: 2 minutes ago

•Source:MetroMLS as distributed by WIREX #1279048

Redfin Estimate

$1,030,554

$761K since sold in December 2012$43K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 25.3% lower than the average sale price ($1.38M) of 6 comparable homes.

SOLD JUL 30, 2026
$1,250,000
A
4 beds3.5 baths5,294 sq ft
N69W34498 Oconomowoc Rd, Oconomowoc, WI 53066
SOLD AUG 24, 2026
$760,000
B
4 beds3 baths3,100 sq ft
W360N7572 Thomas Dr, Oconomowoc, WI 53066
SOLD OCT 20, 2026
$1,200,000
C
4 beds3.5 baths4,108 sq ft
180 Monastery Hill Dr, Oconomowoc, WI 53066
SOLD OCT 1, 2026
$3,500,000
D
4 beds3.5 baths3,900 sq ft
W321N7631 Silver Spring Dr, Hartland, WI 53029
SOLD MAR 20, 2026
$795,000
E
4 beds3.5 baths3,362 sq ft
7135 Mullaney Ct, Hartford, WI 53027
SOLD MAR 19, 2026
$775,000
F
5 beds3.5 baths4,553 sq ft
N1301 State Road 67, Oconomowoc, WI 53066

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Earn from this home

Sell

$823,315

Est. take-home

List your home with Redfin and save $10,306

Rent

$2,577/mo

Redfin rental estimate

List your home for rent

Market trends in 53066, WI

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

100.2%

0.8% MoM

Median sale price

$635K

$10K MoM

Avg. days on market

45d

0 days MoM

Recently sold homes

187

17 MoM

New listings for sale

NEW 24 HRS AGO
$615,000
4 beds3 baths2,865 sq ft
1588 Squash Ct, Oconomowoc, WI 53066
James Bertolli • Vylla Home
NEW 27 HRS AGO
$5,000,000
8 beds6 baths8,200 sq ft
N59W38465 Kohl Ln, Oconomowoc, WI 53066
Karen Trepton • Shorewest Realtors, Inc.
OPEN SUN, 12PM TO 1:30PM
$599,900
4 beds3.5 baths2,600 sq ft
661 Cassie Lynn Ln, Oconomowoc, WI 53066
Elizabeth Bertrandt-Klug • Keller Williams Realty-Lake Country
$1,289,000
5 beds4.5 baths5,910 sq ft
S26W35185 Woodstream Ct, Oconomowoc, WI 53066
Scott Heyerdahl • First Weber Inc - Delafield
$325,000
2 beds2 baths1,557 sq ft
130 Oconomowoc Sq, Oconomowoc, WI 53066
Joseph Jewell • Lake Country Flat Fee
OPEN SUN, 1PM TO 3PM
$484,900
3 beds2 baths1,652 sq ft
755 Armour Rd, Oconomowoc, WI 53066
Tyler Metz • Lannon Stone Realty LLC
$949,900
3 beds3 baths2,600 sq ft
3226 N Interlaken Dr, Oconomowoc, WI 53066
Lake Country Realty Group* • Keller Williams Realty-Lake Country
OPEN SUN, 11:30AM TO 1PM
$469,900
3 beds2 baths1,718 sq ft
1123 S Utica Rd, Oconomowoc, WI 53066
Highmark Re Group* • Keller Williams Realty-Milwaukee North Shore
OPEN SUN, 11AM TO 12:30PM
$599,900
4 beds2.5 baths2,454 sq ft
N64W33734 Lakeview Dr, Oconomowoc, WI 53066
Nicole Zimmer • First Weber Inc - Brookfield
$749,000
5 beds3.5 baths3,472 sq ft
1320 Prairie Creek Blvd, Oconomowoc, WI 53066
David Kiernan • Compass RE WI-Tosa
See all

Provided by Redfin

Sale history for w1443 Roosevelt Rd

Date

Event

Price

MetroMLS as distributed by WIREX #752844

Feb 4, 2013

Listing Removed

—

Feb 4, 2013

Listed

$398,000

$99/sq ft

MetroMLS as distributed by WIREX #1133385

Dec 18, 2012

Listing Removed

—

Dec 18, 2012

Listed

$549,900

$137/sq ft

MetroMLS as distributed by WIREX #1079680

Dec 18, 2012

Listing Removed

—

Dec 18, 2012

Listed

$730,000

$182/sq ft

MetroMLS as distributed by WIREX #1279048

Dec 21, 2012

Listing Removed

—

Dec 21, 2012

Listed

$272,900

$68/sq ft

Dec 14, 2012

Sold

$270,000

$67/sq ft

MetroMLS as distributed by WIREX #772576

Nov 1, 2005

Sold

$380,000

$95/sq ft

Join or sign in to view all info

Year

Property tax

Land + Additions

Assessment*

2025

$10,128 (+3.7%)

$206,800 + $684,900

$891,700

2024

$9,771 (+13.0%)

$206,800 + $684,900

$891,700

2023

$8,645 (−14.6%)

$150,900 + $365,300

$516,200

2022

$10,123 (+8.4%)

$150,900 + $365,300

$516,200

2021

$9,340 (−0.4%)

$150,900 + $365,300

$516,200

2020

$9,375 (+3.3%)

$150,900 + $365,300

$516,200

2019

$9,079 (+8.2%)

$150,900 + $365,300

$516,200

2018

$8,389 (−1.4%)

$150,900 + $365,300

$516,200

2017

$8,512 (+3.5%)

$150,900 + $365,300

$516,200

2016

$8,228 (+2.3%)

$150,900 + $365,300

$516,200

2014

$8,043 (+22.0%)

$150,900 + $363,800

$514,700

2013

$6,595

$150,900 + $247,000

$397,900

Tax history for w1443 Roosevelt Rd

Year

Property tax

Land + Additions

Assessment*

2025

$10,128 (+3.7%)

$206,800 + $684,900

$891,700

2024

$9,771 (+13.0%)

$206,800 + $684,900

$891,700

2023

$8,645 (−14.6%)

$150,900 + $365,300

$516,200

2022

$10,123 (+8.4%)

$150,900 + $365,300

$516,200

2021

$9,340 (−0.4%)

$150,900 + $365,300

$516,200

2020

$9,375 (+3.3%)

$150,900 + $365,300

$516,200

2019

$9,079 (+8.2%)

$150,900 + $365,300

$516,200

2018

$8,389 (−1.4%)

$150,900 + $365,300

$516,200

2017

$8,512 (+3.5%)

$150,900 + $365,300

$516,200

2016

$8,228 (+2.3%)

$150,900 + $365,300

$516,200

2014

$8,043 (+22.0%)

$150,900 + $363,800

$514,700

2013

$6,595

$150,900 + $247,000

$397,900

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

21.47 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Dodge County

APN

00209172721000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 23, 2026.

A-2

General Agricultural District

The purpose of the A-2 General Agricultural District is to promote areas for agriculture which are transitional, allowing for the expansion of urban areas, limited rural residential development, and the conversion of agricultural land to other related uses, subject to appropriate standards.

Permitted uses

Include but are not limited to:

Agriculture
Greenhouse / nursery
Day care facility
Housing-Single unit
Manufacturing
Infrastructure
Park & open space

Property details

Parking

Garage Information
# of Garage Parking Spaces (Total): 2.5
Garage: Attached, 2 Car

Interior

Bedroom Information
Master Bedroom Dimensions: 20 x 25
Master Bedroom Level: Upper
Bedroom 2 Dimensions: 15 x 20
Bedroom 2 Level: Upper
Bedroom 3 Dimensions: 15 x 20
Bedroom 3 Level: Upper
Bedroom 4 Dimension: 15 x 15
Bedroom 4 Level: Upper

Bathroom Information
Bath Description(s): Full Bath on Lower Level, Shower Over Tub, Master Bedroom Bath, 1/2 Bath on Main Level, Full Bath on Upper Level
# of Baths (1/2): 1
# of Baths (Full): 4

Interior Features
Walk-Thru Bedroom, Utility Room (Lower), Living Room, Great Room, 220 Volts, Walk-In Closet(s), Gas Appliance Hookup, Electric Appliance Hookup, Circuit Breakers, Central Vacuum, Bay Window

Room Information
Block, Full
Living Room Dimensions: 20 x 20
Living Room Level: Main
Kitchen Level: Main
Kitchen Dimensions: 20 x 15
Family Room Level: Main
Family Room Length: 15 x 15
Dining Room Dimensions: 15 x 15
Dining Room Level: Main
Den/Office Dimension: 12 x 12
Den/Office Level: Main

Exterior

Building Information
Building Type: 1.5 Story, 2 Story
Roofing: Composition/Fiberglass
Estimated Sq. Ft. Range: 3501-5000

Exterior
Exterior: Brick/Stone, Stone, Vinyl, Stucco/Slate

Property Information
Single-Family

Land Information
Acreage: >= 1, >= 10, >= 1/2, >= 5, >= 20, 20 Less Than 50

Lot Information
Lot Description: Horse Allowed, Hobby Farm, Wooded
Zoning: Residential

Financial

Tax Information
Total Taxes: $10,475.85
Tax Year: 2011

Utilities

Utility Information
Mound System, Private Septic System, Well
Heating/Cooling: Central Air, Forced Air, Radiant/Hot Water
Lp Gas

Location

Neighborhood Information
Municipality: ASHIPPUN
Municipality Type: Town

School Information
School District: Oconomowoc Area

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 21.47 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Dodge County
APN: 00209172721000

Home facts updated by county records on Sep 23, 2026

Around this home

Schools

Meadow View Elementary School

Public PreK-4 • Assigned • 5.9mi

8/10

Nature Hill Intermediate School

Public 5-8 • Assigned • 6.3mi

8/10

Oconomowoc High School

Public 9-12 • Assigned • 8.4mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

1/10 Heat Factor

7 days above 99° expected this year, 13 days in 30 years

2/10 Wind Factor

Minor risk of severe winds over next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Oconomowoc, WI • 53066

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.9 hours in June and 3.4 hours in December, placing it below the U.S. average for solar exposure.

9.9 hrs

3.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$980,000 – $1.19M

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Home values near w1443 Roosevelt Rd

Data from public records.

Address	Redfin Estimate
W1441 Roosevelt Road, Oconomowoc, WI 3 Beds \| 2.5 Baths \| 3214 Sq. Ft.	$922,869
W1373 County Road O, Oconomowoc, WI 4 Beds \| 2.5 Baths \| 2000 Sq. Ft.	$594,417

Address	Redfin Estimate
1539 Roosevelt Road, Oconomowoc, WI 3 Beds \| 3 Baths \| - Sq. Ft.	$562,964
1428 Co Rd O, Oconomowoc, WI 3 Beds \| 3 Baths \| - Sq. Ft.	$536,671

Address	Redfin Estimate
W1539 Roosevelt Road, Oconomowoc, WI 4 Beds \| 3 Baths \| 3200 Sq. Ft.	$733,168
W1396 County Road O, Oconomowoc, WI 4 Beds \| 2.5 Baths \| 2052 Sq. Ft.	$671,089

Property information provided by MetroMLS as distributed by WIREX when last listed in 2012. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 53066, WI

Sale history for w1443 Roosevelt Rd

Tax history for w1443 Roosevelt Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 53066

Home values near w1443 Roosevelt Rd

More real estate resources