Vallee Family House

Westbrook High School (WHS) is a public high school in Westbrook, Maine, United States. The school serves grades 9 through 12, and usually enrolls between 600 and 800 students each year. It is part of the Westbrook School Department. The school competes in the Southern Maine Athletics Association (SMAA) and Class A athletics, as governed by the Maine Principals' Association. The school mascot is the "Blue Blazes".

The Old Westbrook High School is a historic school building at 765 Main Street in central Westbrook, Maine. Built in 1886, it is one of the city's most architecturally sophisticated 19th-century buildings, designed by the Portland firm of Fassett & Tompson. Now converted to senior housing, it was listed on the National Register of Historic Places in 1979.

The Walker Memorial Library is the public library of Westbrook, Maine, United States. It is located at 800 Main Street, in an architecturally distinguished French Chateauesque building designed by Frederick A. Tompson and built in 1894. It was added to the National Register of Historic Places in 1980.

The St. Hyacinth School and Convent are a pair of religious and educational buildings at 2 Walker Street in Westbrook, Maine. The school, built in 1894, is a fine local example of Second Empire design, and the 1922 convent is a good example of Gothic Revival architecture. Both were built by the local Roman Catholic parish of St. Hyacinth to support the burgeoning French-Canadian and French-American community, many of whom worked in the local mills. The buildings were listed on the National Register of Historic Places in 2013. Both have been converted into residential housing.

Westbrook is a city in Cumberland County, Maine, United States and a suburb of Portland. The population was 20,400 at the 2020 census, making it the fastest-growing city in Maine between 2010 and 2020. It is part of the Portland–South Portland–Biddeford, Maine metropolitan statistical area.

The Warren Block is a historic commercial building at Cumberland and Main Streets in Westbrook, Maine, United States. Built in 1882 to a design by John Calvin Stevens, it is a sophisticated example of commercial Queen Anne architecture. It was listed on the National Register of Historic Places in 1974.

The Nathan Harris House is an historic house at 425 Main Street in Westbrook, Maine. Built about 1830, it is a well-preserved example of Federal period architecture, most notable for the murals painted on some of its walls in the 1830s. It was listed on the National Register of Historic Places in 1993. The house is now used as a professional office.

The S. D. Warren Paper Mill is a paper mill on the Presumpscot River in Westbrook, Maine. It is now owned by SAPPI Limited, a South African paper concern. It is one of Westbrook's major employers. The mill complex and former worker and management housing associated with the mill's operation in the 19th century were listed on the National Register of Historic Places in 1974 as the Cumberland Mills Historic District.

Woodlawn Cemetery is a publicly-owned cemetery in Westbrook, Maine, U.S. It was established in 1885. In 1933-34, Woodlawn was significantly improved by a make-work project by the Civil Works Administration. Three miles of avenues were given a coat of gravel among other improvements. It is the only cemetery in the city which offers winter burials.

Spring Harbor Hospital is a 100-bed free-standing nonprofit psychiatric hospital located in Westbrook, Maine. It is one of two free standing psychiatric hospitals in the state of Maine and offers services for both children and adults.

WLOB (1310 AM) is a commercial radio station licensed to Portland, Maine. The station is owned by Atlantic Coast Radio and airs a Talk radio format. The studios and transmitter are on Warren Avenue in Portland. WLOB transmits with 5,000 watts using a directional antenna to protect other stations on its frequency. Programming on WLOB is also heard on FM translators W263BZ on 100.5 MHz in Portland and W252EI on 98.3 MHz in Brunswick.

Smiling Hill Farm is a 500 acre traditional New England farm encompassing parts of the municipalities of Westbrook, Scarborough, and Gorham, Maine. Founded in 1720 as the homestead of Nathaniel Knight, the 12th-generation descendants continue to operate the farm today. Known as the "Knight Farm", the farm was renamed "Smiling Hill Farm" by Roger D. Knight in 1974. Roger named the farm after a favorite childhood book, "Smiling Hill Farm" by Miriam E. Mason (1937). Smiling Hill Farm is known for its characteristic smiling cow logo. According to Family Business magazine, Smiling Hill Farm is the 9th oldest continually operating family business in the United States.