Top Whitefish Bay Neighborhood | Cumberland Forest

The Cumberland Forest neighborhood sits in one of Whitefish Bay’s most desirable pockets, known for its tree-lined streets, historic architecture, and unbeatable walkability. Built primarily in the 1920s, homes in this neighborhood reflect classic North Shore craftsmanship and charm, ranging from 1,800 to 4,200 square feet with three to five bedrooms and 1.5 to 3.5 baths.

The average sale price in the Cumberland Forest Neighborhood is $772,850 for 2025, and saw 14 Home Sales.

One of the biggest draws of Cumberland Forest is its exceptional walkability. Residents are just minutes from The Cornerstone in neighboring Shorewood, a vibrant commercial district offering a full-service grocery store, restaurants, cafés, and popular neighborhood bars.

Cumberland Forest lies in the Cumberland Elementary School district.

Public School options include:

• Cumberland Elementary School (just steps away)
• Whitefish Bay Middle School
• Whitefish Bay High School

Private & Parochial Schools:

• Holy Family Catholic School
• Dominican High School
• University School of Milwaukee
• Milwaukee Jewish Day School

Cumberland Forest residents enjoy access to some of Whitefish Bay’s best recreational amenities. Cahill Park, located just moments from the neighborhood, features lighted tennis courts, baseball diamonds, skating facilities, and open green space. The shores of Lake Michigan and the scenic Oak Leaf Trail are just a few blocks away, making outdoor adventure part of everyday living.

As part of the greater Whitefish Bay community, residents also enjoy a vibrant civic culture with organizations such as the Whitefish Bay Garden Club, Women’s Club, Civic Foundation, North Shore Newcomers Association, and more. Seasonal events like the Whitefish Bay 4th of July Parade, Whitefish Bay 5K/Fun Run, and the Bay Ball bring neighbors together year after year.

What are the average days on Market in Cumberland Forest for 2025? 32 Days

What is the price per square foot for single family homes? $341/sq foot

What is the average square footage of Homes in Cumberland Forest? 2344 Square feet

What is the average Sale Price of homes in Cumberland Forest? $772,850