Is Oconomowoc, WI dog-friendly?

As of early 2026, 91% of users say it's dog friendly

Would people walk alone at night in Oconomowoc, WI?

As of early 2026, 86% of users say people would walk alone at night

Is a car needed in Oconomowoc, WI?

As of early 2026, 86% of users say car is needed

Is parking easy in Oconomowoc, WI?

As of early 2026, 86% of users say parking is easy

Do kids play outside in Oconomowoc, WI?

As of early 2026, 85% of users say kids play outside

Are yards well-kept in Oconomowoc, WI?

As of early 2026, 84% of users say yards are well-kept

Does Oconomowoc, WI show holiday spirit?

As of early 2026, 80% of users say there's holiday spirit

Does Oconomowoc, WI have sidewalks?

As of early 2026, 78% of users say there are sidewalks

Are the streets well-lit in Oconomowoc, WI?

As of early 2026, 76% of users say streets are well-lit

Is there wildlife in Oconomowoc, WI?

As of early 2026, 71% of users say there's wildlife

Is Oconomowoc, WI quiet?

As of early 2026, 67% of users say it's quiet

Do residents of Oconomowoc, WI plan to stay at least 5 years?

As of early 2026, 63% of users say they plan to stay for at least 5 years

Is Oconomowoc, WI walkable to restaurants?

As of early 2026, 59% of users say it's walkable to restaurants

Are neighbors friendly in Oconomowoc, WI?

As of early 2026, 59% of users say neighbors are friendly

Are there community events in Oconomowoc, WI?

As of early 2026, 52% of users say there are community events

Is Oconomowoc, WI walkable to grocery stores?

As of early 2026, 38% of users say it's walkable to grocery stores

What is 255 Ridgeway Path estimated to be worth?

Trulia's estimated value for 255 Ridgeway Path in Oconomowoc, WI is $706,500 .

What is the price history for 255 Ridgeway Path?

255 Ridgeway Path in Oconomowoc, WI last sold for $388,000 in March 2017.

Is Oconomowoc a buyer's or seller's market?

Oconomowoc is currently a seller's market, based on recent for-sale activity.

What's the median sale price in Oconomowoc?

The median sale price in Oconomowoc is $527K. That is up $24K from the prior month.

Does 255 Ridgeway Path have air conditioning?

Yes, 255 Ridgeway Path in Oconomowoc, WI has air conditioning.

Does 255 Ridgeway Path have laundry facilities?

Yes, 255 Ridgeway Path in Oconomowoc, WI has in-unit laundry.

OFF MARKET

$706,500

Trulia Estimate

3 Beds
3.5 Baths
3,562 sqft (on 0.34 acres)

255 Ridgeway Path, Oconomowoc, WI 53066

Est. Refi. Payment $4,354/mo*

Refinance Your Home

Currently Off Market - Sold Mar 29, 2017 for $388,000

Home Value

Trulia Estimate

$707K

Since last month

$25K (-3.4%)

Since last year

$20K (+2.9%)

Since last sale

$321K (+82.6%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +71% in the last 10 years

Month	Estimated value
2026
August 2026	$709K
August 2026	$707K
July 2026	$733K
June 2026	$726K
May 2026	$715K
April 2026	$734K
March 2026	$707K
February 2026	$695K
January 2026	$676K
2025
December 2025	$675K
November 2025	$678K
October 2025	$698K
September 2025	$690K
August 2025	$689K
July 2025	$700K
June 2025	$705K
May 2025	$693K
April 2025	$688K
March 2025	$673K
February 2025	$659K
January 2025	$643K
2024
December 2024	$640K
November 2024	$646K
October 2024	$658K
September 2024	$638K
August 2024	$646K
July 2024	$646K
June 2024	$683K
May 2024	$651K
April 2024	$647K
March 2024	$627K
February 2024	$610K
January 2024	$599K
2023
December 2023	$595K
November 2023	$595K
October 2023	$604K
September 2023	$608K
August 2023	$606K
July 2023	$616K
June 2023	$612K
May 2023	$617K
April 2023	$605K
March 2023	$592K
February 2023	$568K
January 2023	$568K
2022
December 2022	$573K
November 2022	$582K
October 2022	$591K
September 2022	$590K
August 2022	$589K
July 2022	$595K
June 2022	$597K
May 2022	$599K
April 2022	$583K
March 2022	$568K
February 2022	$543K
January 2022	$537K
2021
December 2021	$535K
November 2021	$535K
October 2021	$537K
September 2021	$539K
August 2021	$547K
July 2021	$550K
June 2021	$561K
May 2021	$569K
April 2021	$548K
March 2021	$516K
February 2021	$502K
January 2021	$509K
2020
December 2020	$500K
August 2020	$499K
July 2020	$494K
June 2020	$489K
May 2020	$470K
April 2020	$458K
March 2020	$453K
February 2020	$449K
January 2020	$445K
2019
December 2019	$440K
November 2019	$437K
October 2019	$436K
September 2019	$438K
August 2019	$439K
July 2019	$438K
June 2019	$435K
May 2019	$436K
April 2019	$436K
March 2019	$430K
February 2019	$430K
January 2019	$422K
2018
December 2018	$421K
November 2018	$423K
October 2018	$421K
September 2018	$421K
August 2018	$418K
July 2018	$416K
June 2018	$412K
May 2018	$414K
April 2018	$405K
March 2018	$407K
February 2018	$405K
January 2018	$405K
2017
December 2017	$402K
November 2017	$400K
October 2017	$399K
September 2017	$400K
August 2017	$395K
July 2017	$396K
June 2017	$396K
May 2017	$393K
April 2017	$391K
March 2017	$388K
February 2017	$387K
January 2017	$387K
2016
December 2016	$388K
November 2016	$388K
October 2016	$412K
September 2016	$413K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
255 Lakeridge DRIVE, Oconomowoc, WI	0.07	Single-Family Home	$575,000	03/12/26	3	2.5	2,924
1271 Thomas TRAIL, Oconomowoc, WI	0.23	Single-Family Home	$538,000	01/08/26	3	2.5	3,080
261 Ridgeway PATH, Oconomowoc, WI	0.04	Single-Family Home	$745,000	07/27/26	5	3.5	3,963
268 Lakeridge DRIVE, Oconomowoc, WI	0.06	Single-Family Home	$552,400	07/27/26	3	2	1,809
205 Shore CIRCLE, Oconomowoc, WI	0.16	Single-Family Home	$480,000	10/03/25	3	2	1,682
237 Royal Ridge Dr, Oconomowoc, WI	0.29	Single-Family Home	$540,000	04/16/26	4	2.5	1,946
227 Shore CIRCLE, Oconomowoc, WI	0.29	Single-Family Home	$590,000	04/09/26	4	3.5	2,483
273 Silver Lake TRAIL, Oconomowoc, WI	0.14	Single-Family Home	$575,000	07/31/26	3	2	1,856
727 Browning CIRCLE, Oconomowoc, WI	0.63	Single-Family Home	$500,000	02/20/26	4	3	3,213
1362 Scotsland LANE, Oconomowoc, WI	0.48	Single-Family Home	$805,155	02/06/26	3	2.5	2,555

Nearby home prices

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

Address	Distance	Price	Bed	Bath	Sqft	Status
264 Lakeridge DRIVE, Oconomowoc, WI 53066	0.04	$687,600	3	3	2,800	Off Market
261 Ridgeway PATH, Oconomowoc, WI 53066	0.04	$745,000	5	3.5	3,963	Recently Sold
268 Lakeridge DRIVE, Oconomowoc, WI 53066	0.06	$552,400	3	2	1,809	Recently Sold
255 Lakeridge DRIVE, Oconomowoc, WI 53066	0.07	$575,000	3	2.5	2,924	Recently Sold
1396 Lakeridge DRIVE, Oconomowoc, WI 53066	0.10	$793,500	5	3.5	4,470	Off Market
201 Oconomowoc PARKWAY, Oconomowoc, WI 53066	0.12	$312,000	3	2	1,580	Recently Sold
245 Oconomowoc PARKWAY, Oconomowoc, WI 53066	0.12	$289,900	3	2	1,484	Recently Sold
207 Oconomowoc PARKWAY, Oconomowoc, WI 53066	0.12	$300,000	2	2	1,315	Recently Sold
211 Oconomowoc PARKWAY, Oconomowoc, WI 53066	0.12	$345,700	3	2	1,580	Off Market
215 Oconomowoc PARKWAY, Oconomowoc, WI 53066	0.12	$304,900	2	2	1,389	Off Market
219 Oconomowoc PARKWAY, Oconomowoc, WI 53066	0.12	$344,100	3	2	1,580	Off Market
223 Oconomowoc PARKWAY #223, Oconomowoc, WI 53066	0.12	$291,200	2	2	1,412	Off Market

Local Information

Map ViewExplore the area around 255 Ridgeway Path.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

0.34 acre lot

3,562 sqft

$198/sqft

Garage

About this House

This one owner Westridge built home is located in desirable Lakeridge. Warm and inviting as you step into the 2 story light filled foyer. Open concept kitchen, great room and dining area enjoy backyard views. Flex room could be a formal dining room or office. Functional floor plan with custom organization throughout. Master BR with oversized walk-in and additional space for an office area or reading nook. Comfortable finished spaces for guests including a generous sized full bath in the LL. A must see as the photos do not truly show the craftsmanship & care!

255 Ridgeway Path, Oconomowoc, WI 53066 is a 3 bedroom, 4 bathroom, 3,562 sqft single-family home. It last sold for $388,000 on Mar 29, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $706,500, with a rent estimate of $4,231/month.

Home Details for 255 Ridgeway Path

Interior Features
Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details Types of Rooms: Walk In ClosetWet Bar
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa FireplaceJetted Bath Tub
Security Security System

Property Information
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial

Exterior Features
Exterior Home Features DeckExterior: Vinyl, Wood, BrickPatio
Parking & Garage GarageParking: Garage Attached

Community
Units in Building: 1

Lot Information
Lot Area: 0.34 acres

Price and Tax history

Date	Event	Price
Mar 29, 2017 Source: N/A	Sold	$388,000
Jan 27, 2017 Source: Agent Provided	Listed For Sale	$399,000
Jul 11, 2016 Source: Agent Provided	ListingRemoved	$424,500
May 23, 2016 Source: Agent Provided	PriceChange	$424,500 Price decreased by 4%
Jul 22, 2015 Source: Agent Provided	Listed For Sale	$439,900
Oct 30, 2002 Source: N/A	Sold	$54,900

Year	Property tax	Tax assessment
2024	$6,212	$579,900

Additional Cost

Market trends in Oconomowoc

Last updated August 2026

Avg. sale price

$527K

$24KMoM

Sale-to-List Price

—

Price per sq ft

$261

$1MoM

Available listings

103

7MoM

Around this home

Summit Elementary School
PK-4
Public
504 Students
Oconomowoc Area School District
8/10
GreatSchools Rating
Parent Rating Average
A great school because of excellent leadership. The principal Mr. Stuckey (stoo-kee) is all about the kids and their learning and experience. He’s not political which is a breath of fresh air. He makes decisions based upon the stiludents best interest. He helps with every aspect of the school. He goes above and beyond. The teachers follow suit. Nearly all of the teachers we have encountered seem to love teaching. I highly recommend this school. Please be a part of the positive culture if you plan to send your little ones. We need more of it.
Parent Review
1y ago
11 Reviews

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 Oconomowoc

At least 95 Trulia users voted on each feature.

91 % Say it's dog friendly
86 % Say people would walk alone at night
86 % Say car is needed
86 % Say parking is easy
85 % Say kids play outside
84 % Say yards are well-kept
80 % Say there's holiday spirit
78 % Say there are sidewalks
76 % Say streets are well-lit
71 % Say there's wildlife
67 % Say it's quiet
63 % Say they plan to stay for at least 5 years
59 % Say it's walkable to restaurants
59 % Say neighbors are friendly
52 % Say there are community events
38 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Smqualityservices
Prev. Resident
1y ago
"Friendly dogs in the area lots of parks an great community for walks an going outside. That is alll i love dogs"
0
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Serafin209
Resident
2y ago
"Easy going. Not much traffic. The only traffic is heading towards Milwaukee between 3pm-7pm. My commute is 15 minutes to work."
0
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Jedimasterhess
Resident
2y ago
"Great place to grow a family I had my kids grow from elementary to high school. It is a safe place that has lots to offer "
0
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Makayla B.
Resident
6y ago
"My husband has lived here for years, so I’ve spent a lot of time here. It’s a cute little town that has a very neighborly and inviting feel. "
3
Flag
Paula M.
Resident
6y ago
"You drive most places. We can walk downtown or to the lake but it’s a “2mile stroll”. Lakes are beautiful and downtown is being revitalized."
2
Flag
Erin S.
Resident
6y ago
"I do t have children, however seems kid friendly. Some kids hang out at the nearby park but it doesn’t seem like they are causing trouble. "
1
Flag
Rebecca H.
Resident
6y ago
"People walking dogs everywhere at all times, its wonderful. Some shops downtown have doggy pit-stops where they can get a drink of water"
0
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Natalie P.
Resident
6y ago
"Community is great. Activities for the family for all seasons. Food and entertainment options are top notch. "
1
Flag
Christina R.
Resident
7y ago
"We have moonlit movies, art festivals, parades, bands in the park, Christmas market, and many more special events!"
0
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Brian M. C.
Resident
7y ago
"Nice neighborhood, full of young families and convenient to highways, grocery, schools, and downtown. "
1
Flag
Trulia User
Resident
7y ago
"Everything from gallery night to ladies night in town. Multiple markets throughout the year. Cute and unique shops."
2
Flag
Natalie P.
Resident
7y ago
"Yes people walk there dogs all over the place and several businesses have water bowls out for them. "
0
Flag
Taylornelson62999
Resident
8y ago
"Very friendly, and safe. Little diversity though. Everyone is very willing to help their neighbor. There is definitely a good mix of that small town feel but also close enough to Milwaukee and Delafield to not get bored."
0
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Lake C. A.
Resident
8y ago
"I feel safe in this neighborhood. The community treats the area with full respect and care. Living outside the bigger cities is much more relaxed. Its really amazing to hear children laughing and birds chirping outside my residence, unlike the sound of sirens and people honking their horns in the bigger cities. The fresh water lakes and awesome beaches top our community off like the cherry on top of an ice cream sundae."
0
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mary h.
12y ago
"I used to live in Oconomowoc and many of my friends living in this neighborhood. It is accessible, affordable and a great town."
0
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Famrainey
13y ago
"Oconomowoc has the charm of a small town with the proximity to large town activities. Frequent festivals and family activities make living here fun. A park and walking/biking trail are outside your door. Nearby lakes offer water activities. Schools are excellent, and the people are friendly. It's home. Ahh."
3
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Paul S.
14y ago
"Wonderful community with charm. There is great butcher shop 1 block over across from the park. An event seems to always be happening in and around town from a fine arts festival to moonlit movies in the park to entertain your family."
1
Flag
Olsenhodges j.
14y ago
"House backs up to nature preserve. Great family oriented community."
0
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LGBTQ Local Legal Protections

Frequently asked questions about 255 Ridgeway Path

What is 255 Ridgeway Path estimated to be worth?
Trulia's estimated value for 255 Ridgeway Path in Oconomowoc, WI is $706,500.
What is the price history for 255 Ridgeway Path?
255 Ridgeway Path in Oconomowoc, WI last sold for $388,000 in March 2017.
Is Oconomowoc a buyer's or seller's market?
Oconomowoc is currently a seller's market, based on recent for-sale activity.
What's the median sale price in Oconomowoc?
The median sale price in Oconomowoc is $527K. That is up $24K from the prior month.
Does 255 Ridgeway Path have air conditioning?
Yes, 255 Ridgeway Path in Oconomowoc, WI has air conditioning.
Does 255 Ridgeway Path have laundry facilities?
Yes, 255 Ridgeway Path in Oconomowoc, WI has in-unit laundry.