W1539 Roosevelt Rd, Oconomowoc, WI 53066

Listed by J Tweeden + Associates Team* • First Weber Inc - Delafield. Bought with First Weber Inc - Delafield.

Off market nov 2021 for $465K

$733,168

Est. refi paymentEst. refi $3,548/mo

•

3,200

sq ft

W1539 Roosevelt Rd, Oconomowoc, WI 53066

About this home

Single-familyProperty Type

1970Year Built

10.02 acresLot Size

$229Est. Price/Sq.Ft.

1 garage spacesParking

Listed by J Tweeden + Associates Team* • First Weber Inc - Delafield

Bought with J Tweeden + Associates Team* • First Weber Inc - Delafield

Redfin checked: a minute ago

•Source:MetroMLS as distributed by WIREX #1773499

Redfin Estimate

$733,168

$268K since sold in November 2021$4,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.9% lower than the average sale price ($787K) of 6 comparable homes.

SOLD AUG 21, 2026
$699,000
A
4 beds3 baths2,332 sq ft
N1259 County Road P, Rubicon, WI 53078
SOLD JUN 9, 2026
$726,000
B
4 beds2.5 baths2,642 sq ft
1204 State Highway 83, Hartford, WI 53027
SOLD JUL 13, 2026
$801,000
C
3 beds2.5 baths2,643 sq ft
485 Killarney Rd, Hartford, WI 53027
SOLD AUG 24, 2026
$760,000
D
4 beds3 baths3,100 sq ft
W360N7572 Thomas Dr, Oconomowoc, WI 53066
SOLD OCT 20, 2026
$688,500
E
4 beds3.5 baths3,642 sq ft
6151 O'Connell St, Hartford, WI 53027
SOLD MAY 13, 2026
$1,050,000
F
3 beds2.5 baths2,750 sq ft
7200 Cork Ln, Hartford, WI 53027

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Earn from this home

Sell

$351,999

Est. take-home

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Refinance

Est. cash available

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Rent

$2,484/mo

Redfin rental estimate

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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

$6,195,000
4 beds6.5 baths11,467 sq ft
N76W36211 Saddlebrook Ln, Oconomowoc, WI 53066
Spheeris Team* • Coldwell Banker Elite
$1,449,000
4 beds4.5 baths5,471 sq ft
37868 Nettle Way Ct, Oconomowoc, WI 53066
Jason Hennen • Moving Forward Realty
$329,900
2 beds1 bath720 sq ft
N55W37239 Roland St, Oconomowoc, WI 53066
Erin Waldron • Property Dynamics/Appraisal Specialists
3D WALKTHROUGH
$619,000
3 beds3 baths2,588 sq ft
N52W35344 Lighthouse Ln, Oconomowoc, WI 53066
Patrick Bolger • Patrick Bolger Realty Group
$624,900
4 beds3.5 baths2,600 sq ft
661 Cassie Lynn Ln, Oconomowoc, WI 53066
Elizabeth Bertrandt-Klug • Keller Williams Realty-Lake Country
$380,000
2 beds2 baths1,222 sq ft
320 E Pleasant St #106, Oconomowoc, WI 53066
Christine Leny • Lannon Stone Realty LLC
$678,900
3 beds2 baths1,929 sq ft
1648 Belmont Ln, Oconomowoc, WI 53066
Shelly Budde • Cream City Real Estate Co
$479,900
3 beds3 baths2,650 sq ft
N7789 Maple Ridge Rd, Oconomowoc, WI 53066
Mark Schulz • Redefined Realty Advisors LLC
$425,000
3 beds3 baths2,018 sq ft
539 Bolson Dr, Oconomowoc, WI 53066
Charles Harris • EXP Realty, LLC MKE
See all

Provided by Redfin

Sale history for W1539 Roosevelt Rd

Date

Event

Price

MetroMLS as distributed by WIREX #1773499

Nov 30, 2021

Sold

$465,000

$145/sq ft

Oct 8, 2021

Listed

$450,000

$141/sq ft

Public Records

Sep 23, 2020

Sold

$393,000

$123/sq ft

MetroMLS as distributed by WIREX #1697118

Sep 17, 2020

Sold

$393,250

$123/sq ft

Jul 6, 2020

Contingent

—

Jul 3, 2020

Listed

$399,900

$125/sq ft

Public Remarks

SCENIC HILLTOP VIEWS AND QUIET COUNTRY LIVING ON 10 ACRES OF ROLLING MEADOW. EXPOSED LOWER LEVEL RANCH EXTENSIVELY REMODELED. MASTER SUITE IN THE LOWER LEVEL OFFERS A BEAUTIFUL MASTER BATH, GUEST SUITE ON MAIN FLOOR, 3 BEDROOMS HAVE LARGE WALKIN CLOSETS, SKYLIGHTS GIVE THIS UNIQUE PROPERTY AN OPEN AIRY FEEL, 1ST FLOOR LAUNDRY, COZY GAS FIREPLACE IN THE LR, 4 SEASON ROOM, GREAT VIEW OF HOLY HILL AND WILDLIFE. LARGE GARAGE WITH HEATED OFFICE ATTACHED AND BATHROOM. THIS IS A RARE FIND - DON'T MISS YOUR CHANCE TO OWN PARADISE.

Public Records

Mar 24, 2008

Sold

$325,000

$102/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$6,901 (+3.8%)

$145,200 + $468,100

$613,300

2024

$6,647 (+24.9%)

$145,200 + $468,100

$613,300

2023

$5,323 (−14.6%)

$106,000 + $217,600

$323,600

2022

$6,234 (+8.5%)

$106,000 + $217,600

$323,600

2021

$5,747 (+17.1%)

$106,000 + $217,600

$323,600

2020

$4,906 (+3.6%)

$106,000 + $169,800

$275,800

2019

$4,735 (+8.2%)

$106,000 + $169,800

$275,800

2018

$4,378 (−1.9%)

$106,000 + $169,800

$275,800

2017

$4,464 (+3.6%)

$106,000 + $169,800

$275,800

2016

$4,308 (+1.9%)

$106,000 + $169,800

$275,800

2014

$4,228 (−4.7%)

$106,000 + $169,800

$275,800

2013

$4,435

$106,000 + $169,800

$275,800

Tax history for W1539 Roosevelt Rd

Year

Property tax

Land + Additions

Assessment*

2025

$6,901 (+3.8%)

$145,200 + $468,100

$613,300

2024

$6,647 (+24.9%)

$145,200 + $468,100

$613,300

2023

$5,323 (−14.6%)

$106,000 + $217,600

$323,600

2022

$6,234 (+8.5%)

$106,000 + $217,600

$323,600

2021

$5,747 (+17.1%)

$106,000 + $217,600

$323,600

2020

$4,906 (+3.6%)

$106,000 + $169,800

$275,800

2019

$4,735 (+8.2%)

$106,000 + $169,800

$275,800

2018

$4,378 (−1.9%)

$106,000 + $169,800

$275,800

2017

$4,464 (+3.6%)

$106,000 + $169,800

$275,800

2016

$4,308 (+1.9%)

$106,000 + $169,800

$275,800

2014

$4,228 (−4.7%)

$106,000 + $169,800

$275,800

2013

$4,435

$106,000 + $169,800

$275,800

*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

10.02 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Dodge County

APN

00209172721003

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
Garage: Opener Included, Detached, 2 Car

Interior

Bedroom Information
Master Bedroom Dimensions: 18 x 11
Master Bedroom Level: Lower
Bedroom 2 Dimensions: 17 x 14
Bedroom 2 Level: Main
Bedroom 3 Dimensions: 12 x 12

Bathroom Information
Bath Description(s): Shower on Lower, Tub Only, Ceramic Tile, Walk-In Shower in Master Bathroom, Master Bedroom Bath, Shower Over Tub, Shower Stall
# of Baths (Full): 3

Interior Features
Water Softener, Cable/Satellite Available, High Speed Internet, Pantry, Skylight(s), Cathedral/Vaulted Ceiling, Walk-In Closet(s), Walk-Thru Bedroom

Room Information
Block, Finished, Full, Full Size Windows, Radon Mitigation System, Sump Pump, Walk Out/Outer Door, Exposed
Other Room 1 Dimensions: 22 x 14
Other Room 1 Level: Main
Other Room 1 Name: Sun/Four Season Room
Living Room Dimensions: 20 x 12
Living Room Level: Main
Kitchen Level: Main
Kitchen Dimensions: 12 x 11
Family Room Level: Main
Family Room Length: 20 x 12
Dining Room Dimensions: 12 x 9
Dining Room Level: Main

Equipment
Appliances: Dishwasher, Dryer, Range/Oven, Range, Refrigerator, Washer

Exterior

Building Information
Building Type: 1 Story
Estimated Sq. Ft. Range: 3001-3500, 2501+

Exterior
Exterior Features: Patio
Exterior: Stone, Brick/Stone, Vinyl

Property Information
Single-Family
Information Source Year Built: Assessor/Public Record

Land Information
Acreage: Over 10 to 20 Acres

Lot Information
Lot Acreage: 10.02
Lot Description: Horse Allowed, Hobby Farm, Wooded
Zoning: Residential

Financial

Tax Information
Total Taxes: $4,906.22
Tax Year: 2020

Utilities

Utility Information
Well, Private Septic System
Heating/Cooling: Central Air, Forced Air
Electric, Lp Gas

Location

Neighborhood Information
Municipality: OCONOMOWOC
Municipality Type: Town

School Information
School District: Oconomowoc Area
High School: Oconomowoc

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 10.02 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Dodge County
APN: 00209172721003

Home facts updated by county records on Sep 23, 2026

Other

Listing Information
Inclusions: Oven/Range, Refrigerator, (2) Microwaves, Dishwasher, Water Softener, Iron Curtain, EDORemotes, Washer, Dryer, Play set, Chicken Coop
Exclusions: Basement Refrigerator, Sellers personal property

Around this home

Schools

Meadow View Elementary School

Public PreK-4 • Assigned • 6.1mi

8/10

Nature Hill Intermediate School

Public 5-8 • Assigned • 6.5mi

8/10

Oconomowoc High School

Public 9-12 • Assigned • 8.6mi

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

$697,000 – $844,000

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Charles Harris • EXP Realty, LLC MKE

Home values near W1539 Roosevelt Rd

Data from public records.

Address	Redfin Estimate
W1441 Roosevelt Road, Oconomowoc, WI 3 Beds \| 2.5 Baths \| 3214 Sq. Ft.	$922,869
N726 Franklin Road, Oconomowoc, WI 3 Beds \| 1.5 Baths \| 1800 Sq. Ft.	$409,327

Address	Redfin Estimate
1539 Roosevelt Road, Oconomowoc, WI 3 Beds \| 3 Baths \| - Sq. Ft.	$562,964
N803 Franklin Road, Oconomowoc, WI 4 Beds \| 2.5 Baths \| 2396 Sq. Ft.	$784,573

Address	Redfin Estimate
W1443 Roosevelt Road, Oconomowoc, WI 4 Beds \| 4.5 Baths \| 4003 Sq. Ft.	$1,030,554
N1002 Franklin Road, Oconomowoc, WI 5 Beds \| 4.5 Baths \| - Sq. Ft.	$925,736

Property information provided by MetroMLS as distributed by WIREX when last listed in 2021. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 53066, WI

Sale history for W1539 Roosevelt Rd

Tax history for W1539 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 W1539 Roosevelt Rd

More real estate resources