N55W37091 Roland St, Oconomowoc, WI 53066

Listed by Amber Balistreri • First Weber Inc - Delafield. Bought with Next Home Lake Country.

Off Market Oct 2020 for $259K

$423,747

Est. refi paymentEst. refi $1,990/mo

•

1,671

sq ft

N55W37091 Roland St, Oconomowoc, WI 53066

About this home

Public Remarks: Adorable Cape Cod-style home in the Town of Oconomowoc with new roof and gutters. Home sits on a spacious lot with fresh landscaping. Large eat-in Kitchen has new stainless appliances and access to the back patio overlooking the sprawling yard. Updated full bath on main floor and updated master bedroom. Endless possibilities in lower level with a large Rec Room area, Office area and tons of storage. Huge breezeway between garage and home also offers plenty of storage. Oversized 1.5 car garage with brand new garage door.

Single-familyProperty Type

1960Year Built

0.39 acresLot Size

$254Est. Price/Sq.Ft.

1 car garageParking

Listed by Amber Balistreri • First Weber Inc - Delafield

Bought with Rochelle Gamauf • Next Home Lake Country

Redfin checked: 2 minutes ago

•Source:MetroMLS as distributed by WIREX #1706474

Redfin Estimate

$423,747

$164K since sold in October 2020$5,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.6% higher than the average sale price ($401K) of 6 comparable homes.

SOLD MAY 29, 2026
$415,000
A
3 beds1.5 baths1,741 sq ft
1131 Lily Rd, Oconomowoc, WI 53066
SOLD JUL 10, 2026
$458,750
B
3 beds2 baths1,627 sq ft
445 E Harvard St, Oconomowoc, WI 53066
SOLD JUL 21, 2026
$420,000
C
3 beds2 baths1,528 sq ft
733 N Lapham St, Oconomowoc, WI 53066
SOLD NOV 26, 2025
$350,000
D
3 beds1.5 baths1,620 sq ft
740 E Lisbon Rd, Oconomowoc, WI 53066
SOLD JAN 13, 2026
$340,000
E
3 beds2 baths1,919 sq ft
N55W37033 Harvard St, Oconomowoc, WI 53066
SOLD AUG 28, 2026
$425,000
F
4 beds2 baths1,846 sq ft
607 Poppy St, Oconomowoc, WI 53066

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Earn from this home

Sell

$213,339

Est. take-home

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Refinance

Est. cash available

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Rent

$2,386/mo

Redfin rental estimate

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Market trends in 53066, WI

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.0%

0.1% MoM

Median sale price

$625K

$55K MoM

Avg. days on market

45d

0 days MoM

Recently sold homes

207

16 MoM

New listings for sale

OPEN FRI, 4:30PM TO 6PM
$290,000
3 beds1 bath1,780 sq ft
143 E Luther Ave, Oconomowoc, WI 53066
J Tweeden + Associates Team* • First Weber Inc - Delafield
$2,695,000
3 beds3.5 baths4,568 sq ft
34604 Sunset Dr, Oconomowoc, WI 53066
The Bruce Gallagher Team* • Keller Williams Realty-Lake Country
NEW 12 HRS AGO
$435,000
3 beds2 baths1,776 sq ft
530 S Main St Unit 530A, Oconomowoc, WI 53066
Dave Marek • Realty Executives Integrity Brookfield
OPEN TODAY, 5PM TO 6:30PM
$439,900
5 beds3 baths1,700 sq ft
235 W South St, Oconomowoc, WI 53066
Todd Wage • Lannon Stone Realty LLC
$689,500
4 beds2.5 baths3,086 sq ft
1631 Arthurs Pass, Oconomowoc, WI 53066
The Italiano Team* • Lake Country Flat Fee
$259,900
4 beds2 baths1,536 sq ft
29 S Locust St, Oconomowoc, WI 53066
James Stefl • Fathom Realty, LLC
$644,500
4 beds3 baths2,700 sq ft
1298 Juniper Ln, Oconomowoc, WI 53066
The Elements Realty Team* • Elements Realty LLC
OPEN SUN, 12PM TO 2PM
$669,900
3 beds2 baths1,927 sq ft
2935 Yahara Dr, Summit, WI 53066
Tyler Metz • Lannon Stone Realty LLC
$449,900
3 beds2 baths2,115 sq ft
668 Tulip Ct, Oconomowoc, WI 53066
Paul Liebe • Lake Country Flat Fee
OPEN SUN, 12PM TO 2PM
$619,900
4 beds3.5 baths3,600 sq ft
W2366 Mcaleavey Ct, Oconomowoc, WI 53066
Sarah Zieth • Realty Executives Integrity Brookfield
See all

Provided by Redfin

Sale history for N55W37091 Roland St

Date

Event

Price

MetroMLS as distributed by WIREX #1706474

Oct 16, 2020

Sold

$259,900

$156/sq ft

Sep 13, 2020

Contingent

—

Sep 5, 2020

Price Changed

$259,900

$156/sq ft

Aug 29, 2020

Price Changed

$264,900

$159/sq ft

Aug 26, 2020

Listed

$269,900

$162/sq ft

MetroMLS as distributed by WIREX #811324

Feb 3, 2013

Listed

$216,900

$130/sq ft

Feb 3, 2013

Listing Removed

—

Public Records

Jul 17, 2002

Sold

$145,000

$87/sq ft

Public Records

Aug 22, 1997

Sold

$108,000

$65/sq ft

Join or sign in to view all info

Year

Property tax

Land + Additions

Assessment*

2025

$3,009 (+0.3%)

$73,100 + $281,800

$354,900

2024

$2,999 (+8.7%)

$60,900 + $199,400

$260,300

2023

$2,758 (−8.0%)

$60,900 + $199,400

$260,300

2022

$2,996 (+10.7%)

$60,900 + $199,400

$260,300

2021

$2,707 (−3.0%)

$50,500 + $165,900

$216,400

2020

$2,791 (+3.3%)

$50,500 + $165,900

$216,400

2019

$2,703 (+10.8%)

$50,500 + $165,900

$216,400

2018

$2,440 (+0.2%)

$44,200 + $135,300

$179,500

2017

$2,436 (+6.8%)

$44,200 + $135,300

$179,500

2016

$2,280 (−0.7%)

$42,400 + $117,800

$160,200

2014

$2,296 (−2.8%)

$42,400 + $117,800

$160,200

2013

$2,361

$42,400 + $118,700

$161,100

Tax history for N55W37091 Roland St

Year

Property tax

Land + Additions

Assessment*

2025

$3,009 (+0.3%)

$73,100 + $281,800

$354,900

2024

$2,999 (+8.7%)

$60,900 + $199,400

$260,300

2023

$2,758 (−8.0%)

$60,900 + $199,400

$260,300

2022

$2,996 (+10.7%)

$60,900 + $199,400

$260,300

2021

$2,707 (−3.0%)

$50,500 + $165,900

$216,400

2020

$2,791 (+3.3%)

$50,500 + $165,900

$216,400

2019

$2,703 (+10.8%)

$50,500 + $165,900

$216,400

2018

$2,440 (+0.2%)

$44,200 + $135,300

$179,500

2017

$2,436 (+6.8%)

$44,200 + $135,300

$179,500

2016

$2,280 (−0.7%)

$42,400 + $117,800

$160,200

2014

$2,296 (−2.8%)

$42,400 + $117,800

$160,200

2013

$2,361

$42,400 + $118,700

$161,100

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

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

0.39 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Single Family Residential

County

Waukesha County

APN

OCOT0561098

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 21, 2026.

Property details

Parking

Garage Information
# of Garage Parking Spaces (Total): 1.5
Garage: Opener Included, Tandem, Attached, 1 Car

Interior

Bedroom Information
Master Bedroom Dimensions: 12 x 11
Master Bedroom Level: Main
Bedroom 2 Dimensions: 12 x 9
Bedroom 2 Level: Main
Bedroom 3 Dimensions: 14 x 11
Bedroom 3 Level: Upper

Bathroom Information
Bath Description(s): Ceramic Tile, Tub/Shower Combo in Master Bathroom
# of Baths (1/2): 1
# of Baths (Full): 1

Interior Features
Water Softener, Cable/Satellite Available, High Speed Internet, Wood Floors

Room Information
Block, Full, Partially Finished
Other Room 1 Dimensions: 11 x 10
Other Room 1 Level: Main
Other Room 1 Name: Mud Room
Other Room 2 Name: Loft
Living Room Dimensions: 16 x 12
Living Room Level: Main
Kitchen Level: Main
Kitchen Dimensions: 18 x 15
Den/Office Dimension: 15 x 9
Den/Office Level: Lower

Equipment
Appliances: Dishwasher, Garbage Disposal, Dryer, Microwave, Range/Oven, Range, Refrigerator, Washer

Exterior

Building Information
Building Type: 1.5 Story
Estimated Sq. Ft. Range: 1501-1750
Finished Below Grade Sq. Ft.: 367
Finished Above Grade Sq. Ft.: 1,304

Exterior
Exterior: Fiber Cement

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

Land Information
Acreage: Less Than 1/2

Lot Information
Lot Acreage: 0.39
Zoning: Res

Financial

Tax Information
Total Taxes: $2,703
Tax Year: 2019

Utilities

Utility Information
Well, Private Septic System
Heating/Cooling: Forced Air
Natural 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: 0.39 acres
Style: Single Family Residential
Year Built: —
Year Renovated: —
County: Waukesha County
APN: OCOT0561098

Home facts updated by county records on Sep 21, 2026

Other

Listing Information
Inclusions: Oven/Range, Dishwasher, Refrigerator, Microwave, Washer, Dryer, Water Softener (owned), Swing Set
Exclusions: Basement Refrigerator, Seller's Personal Property

Around this home

Schools

Greenland Elementary School

Public PreK-4 • Assigned • 0.5mi

9/10

Nature Hill Intermediate School

Public 5-8 • Assigned • 0.8mi

8/10

Oconomowoc High School

Public 9-12 • Assigned • 1.4mi

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

2/10 Heat Factor

7 days above 100° 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

$403,000 – $488,000

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Nearby similar homes

OPEN FRI, 4:30PM TO 6PM

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143 E Luther Ave, Oconomowoc, WI 53066

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

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New listings for sale in 53066

OPEN FRI, 4:30PM TO 6PM

$290,000

3 beds1 bath1,780 sq ft

143 E Luther Ave, Oconomowoc, WI 53066

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

$2,695,000

3 beds3.5 baths4,568 sq ft

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The Bruce Gallagher Team* • Keller Williams Realty-Lake Country

NEW 12 HRS AGO3D WALKTHROUGH

$435,000

3 beds2 baths1,776 sq ft

530 S Main St Unit 530A, Oconomowoc, WI 53066

Dave Marek • Realty Executives Integrity Brookfield

OPEN TODAY, 5PM TO 6:30PM

$439,900

5 beds3 baths1,700 sq ft

235 W South St, Oconomowoc, WI 53066

Todd Wage • Lannon Stone Realty LLC

$689,500

4 beds2.5 baths3,086 sq ft

1631 Arthurs Pass, Oconomowoc, WI 53066

The Italiano Team* • Lake Country Flat Fee

$259,900

4 beds2 baths1,536 sq ft

29 S Locust St, Oconomowoc, WI 53066

James Stefl • Fathom Realty, LLC

$644,500

4 beds3 baths2,700 sq ft

1298 Juniper Ln, Oconomowoc, WI 53066

The Elements Realty Team* • Elements Realty LLC

OPEN SUN, 12PM TO 2PM

$669,900

3 beds2 baths1,927 sq ft

2935 Yahara Dr, Summit, WI 53066

Tyler Metz • Lannon Stone Realty LLC

$449,900

3 beds2 baths2,115 sq ft

668 Tulip Ct, Oconomowoc, WI 53066

Paul Liebe • Lake Country Flat Fee

Home values near N55W37091 Roland St

Data from public records.

Address	Redfin Estimate
N55W37069 Roland St, Oconomowoc, WI 3 Beds \| 2.5 Baths \| 1686 Sq. Ft.	$510,873
N55W37073 Harvard St, Oconomowoc, WI 3 Beds \| 1.5 Baths \| 1611 Sq. Ft.	$416,267

Address	Redfin Estimate
N55W37049 Roland St, Oconomowoc, WI 3 Beds \| 2 Baths \| 1140 Sq. Ft.	$376,833
N55W37041 Lisbon Rd, Oconomowoc, WI 3 Beds \| 2 Baths \| 1390 Sq. Ft.	$417,699

Address	Redfin Estimate
W371N5580 Marquette St, Oconomowoc, WI 3 Beds \| 1.5 Baths \| 1160 Sq. Ft.	$406,340
W371N5540 Marquette St, Oconomowoc, WI 2 Beds \| 1 Baths \| 918 Sq. Ft.	$342,944

Property information provided by MetroMLS as distributed by WIREX when last listed in 2020. 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 N55W37091 Roland St

Tax history for N55W37091 Roland St

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 N55W37091 Roland St

More real estate resources