The Wayside (Henry Demarest Lloyd House)

Edgecliff (aka the Max Epstein House) is a Samuel Abraham Marx–designed estate in Winnetka, Illinois, in the wealthiest region of Chicago's affluent North Shore suburbs. It is notable for once having the highest residential property taxes in Cook County, Illinois.

The Community House, also known as the Winnetka Community House, is a 3-acre (1.2 ha) community center located at 620 Lincoln Avenue in Winnetka, Illinois. The center was completed in 1911, though it has been expanded several times since. Architect Arthur Coffin designed the building primarily in the Tudor Revival style, though his design also incorporated elements of the Prairie School. The building hosted a wide variety of community activities for all ages and genders, including sports and gym classes in its gymnasium, music and photography groups, billiards, and lectures; by the end of 1911, 51 different groups had begun meeting in the center. While the Community House was nonsectarian, its establishment and operation were heavily influenced by Winnetka's Congregational Church and inspired by its principles of community, education, and youth outreach. In keeping with the popular contemporary settlement movement, the church also planned the center as a settlement house; while it lacked living spaces, it included other typical settlement houses features such as its gymnasium, dining areas, and meeting rooms.The community center was listed on the National Register of Historic Places on August 30, 2007.

Hadley, formerly Hadley Institute for the Blind and Visually Impaired, is an American non-profit, based in Winnetka, Illinois. It offers instruction and classes for individuals who have lost their vision or are blind. Hadley is a partner of the National Eye Institute (NEI) and the National Eye Health Education Program (NEHEP).

Winnetka is a station on Metra's Union Pacific North Line located in Winnetka, Illinois. Winnetka station, located at 754 Elm Street in Winnetka, is 16.6 miles (26.7 km) away from Ogilvie Transportation Center, the inbound terminus of the Union Pacific North Line. In Metra's zone-based fare structure, Winnetka is in zone D. As of 2018, Winnetka is the 68th busiest of Metra's 236 non-downtown stations, with an average of 754 weekday boardings.Winnetka station is located in a below-grade trench. The platforms are accessible via stairs from Elm and Oak Streets and a passenger bridge. An elevator for handicapped access is also located on the passenger bridge. The station consists of two side platforms which serve two tracks. A station house is located at street level; the station house is open from 5:15 A.M. to 1:15 P.M., and tickets are sold on weekdays. Parking is available in a lot adjacent to the station house. The Green Bay Trail, a hiking and bicycle trail, runs east of and parallel to the railroad tracks at Winnetka and can be accessed from the inbound platform. As of April 25, 2022, Winnetka is served by all 35 trains in each direction on weekdays, by all 13 trains in each direction on Saturdays, and by all nine trains in each direction on Sundays. On weekdays, seven outbound trains terminate at Winnetka, and six inbound trains originate from this station. Winnetka was originally built at grade level when it served the Chicago and North Western Railway. As an increasing amount of railroad traffic came through Winnetka, the railroad crossings became unsafe, and 29 people had been killed at railroad crossings by 1937 despite safety efforts by the city and the railroad. After the deaths of two prominent Winnetka women at the Pine Street crossing on October 20, 1937, Winnetkans demanded that the grade crossings be removed. The city elected to put the tracks in a below-grade trench to avoid dividing the city with an elevated railroad. With the help of funding from the Public Works Administration, the tracks were lowered into a trench by 1943. Winnetka and Hubbard Woods stations were located at street level with access to station platforms by stairs from a pedestrian walkway across the tracks, and Indian Hill became an elevated station.

The Lola Maverick Lloyd House is a historic house at 455 Birch Street in Winnetka, Illinois. The house was built in 1920 for pacifist and feminist activist Lola Maverick Lloyd and her four children. At the time, Lloyd had recently undergone a public divorce from William Bross Lloyd; while she expressed a desire to move back to Texas, where she had grown up, her custody agreement required her to stay in Illinois. Architect Charles Haag designed the house with the assistance of Lloyd herself; their design is in the Arts and Crafts style and includes influences from both Texas and Haag's native Sweden. The house has a distinctive red, cream, turquoise and teal color scheme and features carved wooden decorations inspired by animals and nature, gable ends with board-and-batten siding, and shed-roofed dormers projecting from the roof. While she often rented it while traveling to Europe to advance her activist work, Lloyd considered the house her home until her death in 1944, and it remained in her family for the rest of the twentieth century.The house was added to the National Register of Historic Places on February 1, 2006.

Winnetka () is a village in Cook County, Illinois, United States, located 16 miles (26 km) north of downtown Chicago. The population was 12,316 as of 2019. The village is one of the wealthiest places in the nation in terms of household income. It was the second-ranked Illinois community on Bloomberg's 2019 Richest Places Annual Index. In 2020, 24/7 Wall St ranked Winnetka as the second-best small town to live in the United States.

The Dr. Paul W. and Eunice Greeley House is a historic residence in Winnetka, Illinois. Dr. Greeley was a major figure in the field of plastic surgery around World War II and later served as department chair at two universities. Designed by Frank Polito, and with a dining room probably designed by Fiske Kimball, the Classical Revival residence closely follows a Greek Revival design and was listed on the National Register of Historic Places in 2011.

Hubbard Woods is a station on Metra's Union Pacific North Line located in Winnetka, Illinois. Hubbard Woods is located at 1065 Gage Street. Hubbard Woods is 17.7 miles (28.5 km) away from Ogilvie Transportation Center in Chicago, the southern terminus of the Union Pacific North Line. Trains continue as far north as Kenosha, Wisconsin. In Metra's zone-based fare system, Hubbard Woods is in Zone D. As of 2018, Hubbard Woods is the 120th busiest of Metra's 236 non-downtown stations, with an average of 396 weekday boardings.Hubbard Woods consists of a station and two side platforms which serve two tracks, with northbound trains using the west platform and southbound trains use the east platform. The station is located at street level and is open from 5:15 A.M. to 1:00 P.M. The platforms at Hubbard Woods are located in a below-grade depression. The platforms are accessible from Scott Avenue as well as a pedestrian bridge adjacent to the station house. Parking is available at Hubbard Woods. As of April 25, 2022, Hubbard Woods is served by 23 inbound trains and 21 outbound trains on weekdays, by 11 trains in each direction on Saturdays, and by eight trains in each direction on Sundays. The Green Bay Trail, a hiking and bicycle trail, runs parallel to the train tracks at Hubbard Woods and is accessible from the platforms. Until November 2015, this station had a ticket agent.

The John Rogerson Montgomery House is a residence designed by country house architect Howard Van Doren Shaw in Glencoe, Illinois, United States. It is considered to be a significant example of Georgian Revival architecture mixed with Arts & Crafts influences.

The Louis B. Kuppenheimer Jr. House is a historic house at 789 Burr Avenue in Winnetka, Illinois. The house was built in 1937-38 for Louis B. Kuppenheimer Jr. and his family; Kuppenheimer had inherited a large manor house from his father, who had been the president of a clothing company, but wished to move to a smaller home. Architect David Adler, a prominent architect best known for designing country houses, designed the house in the French Renaissance Revival style. The house's design includes a recessed arched entrance, French doors along the south and west sides, a service wing with a mansard roof, a porch wing, and a dentillated cornice. While the house is smaller than most of Adler's works, it still exhibits the typical themes of his designs, such as eclecticism, symmetry, and attention to detail.The house was added to the National Register of Historic Places on December 4, 2017.

Sacred Heart School is a private, Catholic school located in the Hubbard Woods neighborhood of Winnetka, Illinois and the village's oldest operating K-8 school, having been established in 1902. It serves approximately 200 students from pre-kindergarten through eighth grade. In addition to Winnetka, the school draws from the surrounding communities of Glencoe, Northfield, Wilmette and Highland Park. Sacred Heart School is part of the Roman Catholic Archdiocese of Chicago and a member of the National Catholic Educational Association and has been recognized by the National Blue Ribbon Schools Program. The school holds an A+ grade from private schools ranking site Niche.com.

North Shore Country Day School is a selective prep school in Winnetka, Illinois. It took its current form as a coeducational school in 1919 during the Country Day School movement, though it started as the Rugby School for Boys (1893-1900) and Girton School for Girls (1900-1918). It consists of a lower school, a middle school, and an upper school. North Shore Country Day School offers a liberal arts education with students who represent the community values of respect and inclusiveness.