A home in the Washington Highlands, built in 1926 and owned for more than 60 years by an OB-GYN doctor and his family, is up for sale with a reported asking price of $2,150,000. The listing, as public sales records show, is the most expensive single-family home ever to hit Tosa's increasingly pricey housing market, and at that value, it would become the first in the city to sell for more than $2 million.
The home at 1651 Alta Vista Drive is six bedrooms and four full bathrooms across 5,500 square feet of living space. It was the longtime home of Dr. John Brennan and his wife, Joan Brennan, who had 11 children together. John Brennan died in 2014 at age 91, and Joan Brennan died in December 2024 at age 96.
Double Boldt Real Estate began teasing the property in social media posts Aug. 18, saying it was coming to market soon. For decades, "this Washington Highlands treasure has been loved by one family," the agency said in an Aug. 21 post. "Now, for the very first time, it’s ready to begin a new chapter."
The English Revival-style home, clad in stone, sits prominently atop a hill in the upscale and historic Highlands neighborhood, a location that was touted by the real estate agency for providing "sunrise and sunset views, with downtown on the horizon." It also has a "rare three-car attached garage" and sits on "an iconic lot in a thriving neighborhood."
"Homes like this don’t come around twice," Double Boldt Real Estate said. "And we can’t wait to show you what lies behind the door."
The home at 1651 Alta Vista Drive was valued by the city's assessor's office at $1,246,500 in the citywide revaluation this year. Double Boldt Real Estate has not yet posted an asking price for the property on its website, which still lists the home as "coming soon," though On Milwaukee's Bobby Tanzillo, after talking to agent Corey Boldt for a feature story about the property, reported that it would be listed for $2,150,000. [Update: After this article was posted, the listing was changed to "active" on the Boldt Real Estate website.]
If that sounds like a staggering sales price for a Tosa house in Tosa, there's good reason: It's a new record for single-family houses in the city, where even a $1 million home was unprecedented just a few years ago.
Tosa Forward News reviewed sales history for high-end homes in Wauwatosa and found that only 25 publicly listed homes have sold for $1 million or more, all of them since 2023.
The locations of those 25 homes span several city neighborhoods, mostly north of Tosa Village and east of the Menomonee River. Nine of the million-dollar homes are in the neighborhoods that straddle Wauwatosa Avenue near Tosa East High School. Three more are on the same street, Pasadena Boulevard in the Pasadena neighborhood. Another six million-dollar homes are clustered in the neighborhood just north of Bluemound Road and east of Glenview Avenue.
The Washington Highlands, though known for its in history and grand architecture, has only had two homes sell for more than $1 million. One of those is the current record-holder, 6113 W. Washington Blvd., which sold in July 2025 for $1,750,000 after officially being on the market for only nine days.
The new-to-market home on Alta Vista Drive is less than a half mile directly west of that record-holder. Both have about the same square footage but their features and history are distinct.
Records maintained by the Wisconsin Historical Society indicate the home at 1651 Alta Vista Drive was first built and occupied by Ernest and Burdell Swendson. Ernest Swendson owned an automobile sales business. The building permit is dated April 1926, and the contractor R.A. Uecker was paid $40,000. The design is credited to architects Buemming & Guth.
The website Historical Highlands, in a feature about the home, cited numerous characteristics of the revival style "including a dominant front-facing gabled entry; multiple-light, leaded-glass windows; stone, brick or stucco and false half-timber sheathing (or a combination thereof); wood-shingle, slate or tile-covered gabled roofs; and a dominant chimney."
The most dramatic approach is from Washington Boulevard to the east. The boulevard ends at Washington Circle, and from there, a pedestrian pathway winds up a grassy hill to Alta Vista Drive. This natural feature of the Highlands is known as Applecroft Park, a nod to an orchard that formerly was part of the Frederick Pabst farm until the neighborhood's 133 acres were converted into residential streets starting in 1916.
Looking up the Applecroft hill, "see how effectively the fine Tudor Revival house that covers the highest ground closes the Washington Boulevard vista," advises the program from a 1991 Highlands walking tour.
At the top of the hill, tall hedges now frame the steps up to the front door at 1651 Alta Vista Drive. The home also is accessible on the other side, from Mountain Avenue, and features an in-ground swimming pool.
Photos of the home posted to Double Boldt Real Estate's website also show a finished basement, classic wood fixtures and ornate iron railings.
"This house retains a significant amount of original detailing, including tile floors, leaded glass, an imposing stone fireplace and extensive woodwork throughout," Historical Highlands said in its article, based on research provided by the Wauwatosa Historical Society.
The Brennans bought the house in 1959, according to Tanzillo's research for On Milwaukee, which combined newspaper advertisements and interviews with the Brennans' living descendants.
“Everyone was saying it was haunted. But my mom was like, ‘Well, I need a house,'" daughter Brigid Brennan told On Milwaukee. “My mom went through the house and there were no ghosts. She came back a second time and they had washed the windows and she's like, ‘This is the house.' And then they bought the house.”
She and her siblings told On Milwaukee that after their mother died, they decided it was time for a new family to enjoy the house at 1651 Alta Vista Drive.
“I hope they love it as much as we did,” daughter Jan Kaufman said.
- Got tips, suggestions, questions and other feedback? Send them to editor@tosanews.com.
