Winnetka is a village adjacent to Kenilworth, Northfield and Glencoe, located right on Lake Michigan. Winnetka is one of the richest villages in the entire United States – according to Wikipedia, average household income in the village exceeded $250,000 per year. This is an incredibly impressive result, which translates, among other things, into the architecture that can be found in the area. In this article, we will take a look at the nature of development in Winnetka and analyze the current state of the real estate market.
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Winnetka’s History
The history of this village goes all the way back to 1836, when Erastus Patterson and his family built the first tavern next to the Green Bay Trail mail route, which connected Fort Dearborn in Chicago to Fort Howard, Wisconsin. It was the first building in the area. From then on, people began to settle there – One of them was Charles and Sarah Peck, later known as the founders of Winnetka. It was Sarah who came up with the name Winnetka, which meant “Beautiful Land” in Indian.
What made Winnetka such a prosperous neighborhood? Actually, there were several reasons for this. First of all, from the early days of the neighborhood’s greater flourishing, the area was carefully planned in terms of spatial order, aiming to keep Winnetka a neat, aesthetically pleasing and exclusive neighborhood (the same assumptions as in case of development of Kenilworth). From the beginning, authorities prioritized low-density development, manifested by large lots with single-family homes, and limited overdevelopment and commercialization. Unlike other Chicago neighborhoods, Winnetka deliberately limited industrial development and larger commercial complexes. In addition, Winnetka became known for its excellent public schools and innovative educational solutions. A prime example of this is the Winnetka Plan, an experimental children’s education program implemented in 1919.
These reasons overlapped, over time using a snowball effect beginning to create the well-kept, wealthy and exclusive neighborhood that Winnetka is now.
Architecture of Winnetka

Winnetka boasts a wide range of architectural styles applied to buildings. The village has at times played host to a number of talented architects who have further enhanced Winnetka’s landscape with interesting designs. These included Walter Burley Griffin, Andrew W. Paulson and Joseph Fujikawa, whose designs were decidedly different from most houses in the area.
In the picture: Walter Burley Griffin
Winnetka boasts a wide range of architectural styles applied to buildings. The village has at times played host to a number of talented architects who have further enhanced Winnetka’s landscape with interesting designs. These included Walter Burley Griffin, Andrew W. Paulson and Joseph Fujikawa, whose designs were decidedly different from most houses in the area.
In the picture: Walter Burley Griffin
Zdecydowanie najsłynniejszym z architektów, którzy dołożyli się do piękna Winnetki był Walter Burley Griffin, najbardziej znany z zaprojektowania miasta Canberry, czyli stolicy Australii oraz kilku innych miast w tym kraju. Griffin urodził się niedaleko, bo w Maywood, IL i studiował architekturę na University of Illinois Urbana-Champaign. W Winnetce stał do 2022 roku dom wybudowany ponad 100 lat wcześniej, nazwany “The solid rock house”
By far the most famous of the architects who contributed to Winnetka’s beauty was Walter Burley Griffin, best known for designing the city of Canberra, Australia’s capital, and several other cities in this country. Griffin was born nearby in Maywood, IL and studied architecture at the University of Illinois Urbana-Champaign. A house built more than 100 years earlier, called “The solid rock house,” stood in Winnetka until 2022.

Some beautiful works were left behind by Swedish architect Andrew W. Paulson. He came to Winnetka with his wife in 1905 and lived there until 1939. During his stay, he designed several Swedish-style houses, which can still be seen today on Greenwood Avenue and Tower Road.

Another interesting personality who visited, and eventually settled in Winnetka, was architect Joseph Fujikawa. He was a close associate of the famous Ludvig Mies Van Der Rohe, the German modernist architect and one of the leading exponents of the International Style. When Mies Van Der Rohe died in 1969, Fujikawa took over the office from him. He designed his family home in Winnetka, which still stands today at 381 Fairview Ave. The house can be purchased now for about $1.5 million.

Architectural Styles
In Winnetka, as in neighboring Kenilworth, there are several dominant architectural styles, such as Colonial Revival, Tudor and Georgian. However, less popular styles can also be found, such as Prairie, Mediterrarean and Gothic Revival styles. Most of the houses in Winnetka were built in the late 19th century or the first half of the 20th. Back then, Winnetka was already a wealthy and exclusive neighborhood, making homeowners focus on elegance, solidity and aesthetics.
Colonial Revival
Colonial Revival is a classic American style inspired by 18th century colonial construction. It is characterized by symmetrical facades, a gabled roof, brick or wood facades and often a porch taken from the Georgian style.

Tudor Revival style
The style, inspired by English houses of the late Middle Ages and Renaissance, especially those of the Tudor dynasty (hence the name), was favored by wealthy owners in Winnetka. It is characterized by steep, multi-pitched roofs, often covered with cedar shakes, ornate wooden beams and an irregular building mass.

Georgian style
An elegant style inspired by 18th-century British architecture from the Hanoverian Dynasty period. It symbolizes tradition and prestige. It is characterized by a symmetrical facade and a brick facade often in red or brown.

Prairie style
The prairie style was pioneered by architect Frank Lloyd Wright, a famous American modernist architect who also designed in the Chicago area. Houses in this style are characterized by low stretched volumes, flat roofs, large windows and good integration with nature.

Mediterranean
This is a much rarer, though still found in Winnetka, style. It is reminiscent of Mediterranean buildings, which can be seen through the use of red tiles and light plaster facades. Standing out from more popular, traditional styles, Mediterranean-style houses add a bit of Southern elegance to the neighborhood.

Gothic Revival style
Another interesting architectural style found in Winnetka is the Gothic Revival style. It gives a rather romantic and mysterious character to the buildings, without taking away from their elegance. It can be recognized by the soaring roofs and pronounced arches over windows and doors, ornate details and darker shades of the facade. A perfect example of such a house is the current headquarters and museum of the Winnetka Historical Society – the building was built all the way back in 1859.
Real Estate Prices in Winnetka
Due to the exclusivity of a village like Winnetka, real estate prices are very high. And we are talking here practically only about houses, due to the nature of the development. The average price of a home in the neighborhood, according to zillow.com, is $1,643,550, up 6.5% from last year. The median is slightly higher, at $1,883,167. Looking at popular listing portals, however, the aforementioned average may seem somewhat understated. Currently, there are less than 50 listed for sale, the large majority of which have pending or contingent status. Properties that are not pending sale are about 20.
Only 1 house under $1M can currently be found online, and it is a smaller property. Any larger house is definitely above the million mark and, depending on a number of factors, can reach several million dollars. The range from one to two million offers us 3 options, one of which is a condo. The range from two to three is some nice, well-maintained homes. From 3 million upwards you can already see beautiful, large estates.
A million-dollar House in Winnetka, Il.
With a budget of about $1 million you can live in Winnetka. In such a situation you have a choice of a condo, of which there are quite a few in the area, or a house of smaller gabbets, although usually well-kept and nice. Such properties usually have 2 bedrooms and 2 bathrooms each. Houses in Winnetka can sometimes be bought even at very low prices of $600,000 thousand, but they may need renovation. As Winnetka exterior contractor operating, we can help assess the condition of the property and make repairs.
For slightly over $1 million, you can already purchase a slightly larger property with 3 or 4 bedrooms. These houses usually do not stand out in elegance from more expensive properties, and some are really impressive. The problem may be sooner availability, as there are currently only 2 houses for sale in the price range up to $1,400,000.
A $2 Million House in Winnetka
On a budget oscillating around 2 million in Winnetka, it is possible to buy a really beautiful house with an area of more than 5,000 sqft. Often these houses are in the style of contemporary architecture, but you can also come across colonial, tudor and georgian. There are currently several listings at this price – all have more than 4 bedrooms, and some have a plot of almost 3 acres in area.
The Most Expensive Properties in Winnetka
Aren’t you curious about what the most expensive properties in Winnetka are? The tenth richest zip code in the US certainly boasts some grand estates. So let’s see what are the most expensive properties currently for sale and take a peek at historical transactions.
There are currently 2 active listings on the Internet, which are eye-catching in their price. The amounts assigned to them are a staggering $8,361,000 and $9,999,500.
140 Sheridan Road – $8,361,000
The most expensive ad available on the Internet belongs to a beautiful property located at 140 Sheridan Road. This nearly 100-year-old home was built in the Tudor revival style and sits on a 4,530-square-foot lot. The owner can enjoy 7 bathrooms and a total of 12 rooms, one of which has a gym and another a cinema space. In addition, there is a swimming pool and sauna on the lot.

139 Sheridan Road – $9,499,900
Adjacent to the previous property, the residence is located right on Lake Michigan. The beautiful Cape Cod-style home has 5 bedrooms, 8 bathrooms and a mini golf room. It was one of the last to get permission to build on the cliff itself, right next to the water.

627 Sheridan Road – $13,740,500
The house at 627 Sheridan Rd is the most expensive sold property we could find online. We have to admit that this house is impressive. Like the previous one, it is located right on Lake Michigan. It has 7 bedrooms and 4 bathrooms in it and lies on a 1.72 acre plot.

Bonus – 671 Lincoln Avenue
With the most expensive properties in Winnetka, one can’t help but mention the residence at 671 Lincoln Ave. And although it is not among the most expensive in terms of price, the sentiment of all fans of the 1990 blockbuster Home Alone adds to its value. To be exact, this house was the family home of Kevin himself, who defended it against two burglars. The property was relatively recently sold again, this time for also a large sum – $5,500,000.

Why Are Property Prices in Winnetka so High?
The Neighborhood’s Elite Reputation and Prestige
Winnetka is one of the wealthiest neighborhoods in the entire US and definitely in the Chicago area. This village is inhabited by very high-status people – doctors, lawyers, businessmen and owners of assets worth up to hundreds of millions of dollars. This level of residents minimizes the risk of unpleasant situations in the neighborhood due to inappropriate or even pathological behavior of neighbors.
Excellent Level of Education
As mentioned earlier, Winnetka is famous for its high level of education and progressive approach to teaching. Children from kindergarten to 8th grade are educated in one of the schools in the district called district 36. This one brings together a total of five schools, three of which are elementary and two secondary. Each school included in this collection upholds the tenets of the “Winnetka plan,” as does New Tier Highschool – children of Winnetka residents from 8th to 12th grade attend there. This school offers a very rich arts and sports program and advanced courses. New Tier Highschool has a very high enrollment rate at prestigious universities, making it the 7th best high school in Illinois.
In addition, Winnetka also has private schools with very high tuition and very low student-teacher ratios. All of this contributes to Winnetka’s reputation as a district that prides itself on its high level of education. This fact further convinces wealthy families from the US to live in the area.
Character of the Development and Location
Winnetka combines everything that a dream neighborhood could offer for living. The development plan has for many years forbidden over-commercialization and the construction of industrial centers, and has placed a premium on single-family homes. As a result, virtually the entire village area is filled with green plots of land with beautiful residences in various styles. On top of this, the authorities of Winnetka attach great importance to green areas – there are many parks in the area, trees grow along the roads and on the properties, and the village is separated from the northfield by the vast Skokie Lagoons, ideal for relaxing in nature.
The neighborhood’s location, just 20 miles from Chicago, also adds to its value. Winnetka residents can reach Illinois’ largest city by car as well as by train, which will take about 30 to 40 minutes. This is a great option for people working in Chicago who want to live in a quiet, upscale location.
Limited Supply and High Demand
There is practically no more room for new houses in Winnetka. When a building is demolished there, a new, even more expensive residence is immediately built. As was the case with the aforementioned Solid Rock House. This village enjoys great popularity and, of course, an impeccable reputation, and there are very few opportunities to buy a house or build one. For this reason, the value of the houses is inflated by the cost of acquiring the land to build them.
Is Winnetka a Good Place to Live?
In our opinion, definitely yes. If you only have the funds to live in this beautiful village, you should definitely consider it. Winnetka’s residents highly praise it as a place to live – they point out the safety and tranquility, the high level of education and the friendly community. New residents are always warmly welcomed by their neighbors, which facilitates integration, and the high social status of the residents makes Winnetka a prestigious community with a high level of personal culture and savoir-faire.