These are the highest-priced home sales reported in the Madison Metro Area, Wisconsin for the week ending November 1, 2026, and together they came to $5.895 million. Four of the five are in Dane County, with two in Madison and one each in Verona and Oregon, while the fifth is in Blanchardville in Green County.
The homes span nearly a century, from a Prairie/Craftsman home built in 1925 to one finished in 2020. They range from a corner lot in an established Madison neighborhood to nearly 15 acres of countryside, and two of them sold at the same price.
No. 1 — $1,470,000 · 7616 Tumbledown Trl, Verona, Wisconsin
The newest home in this week’s group, built in 2020, sold for $1,470,000 at 7616 Tumbledown Trail in the Tumbledown Farm neighborhood of Verona. It is a two-story custom home in a blend of contemporary and colonial styles, finished in wood siding and stone, with five bedrooms, five bathrooms and 4,674 square feet on a 0.66-acre lot. The home overlooks Pioneer Pointe.
In the great room, a fireplace rises from floor to ceiling between custom built-in shelves. The kitchen is planned around a large island and a six-burner range with a griddle, with a walk-in pantry, and it opens to a dinette where a wine bar, a wine cooler and beverage refrigerator drawers are set up. Off the dinette, a screened porch with its own fireplace leads to a deck. Two offices are on the main level, one behind French doors with built-in cabinetry and the other suited to flexible use.
On the second floor, the primary suite has a soaking tub, a tiled shower and a double vanity, and the laundry is on the same floor. Two of the other bedrooms are connected by a Jack-and-Jill bath. The walkout lower level is finished with a family room, a wet bar, another bedroom and a full bath, and it opens to the backyard. An oversized attached garage has room for three cars. The property last sold for $1.465 million in 2023.
Denise Holmes and Lindsay Koth of Collective Real Estate Group were the listing agents for the top sale of the week, and Lisa Piekarski-Knutson of Real Broker LLC represented the buyer.
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No. 2 — $1,200,000 · 1053 Winged Foot Dr, Oregon, Wisconsin
On the Bergamont Golf Course in Oregon, the home at 1053 Winged Foot Drive in The Legend at Bergamont sold for $1,200,000. From its 0.54-acre lot, the home looks out over the 10th and 18th fairways and toward the clubhouse.
Built in 2005, the one-story ranch is clad in stucco and stone and has 6,638 square feet, the most living space of the five homes. It has five bedrooms and five bathrooms, four full and one half. Wood floors run through the main living area, where vaulted ceilings rise above a tiled fireplace, one of three or more fireplaces in the home. In the kitchen, Sub-Zero, Viking and Thermador appliances surround a large center island. There is also a three-season room.
Much of the entertaining happens on the walkout lower level, which has a family room with a wet bar, a wine room, a theater and an exercise room. Outside, a deck and a patio are joined by a stone fire pit area. The garage holds three cars. The property last sold for $695,000 in 2008.
Annette Riemer of First Weber Inc was the listing agent, and Sherry M McKee of Stark Company, REALTORS represented the buyer.
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No. 3 — $1,100,000 · 2450 Commonwealth Ave, Madison, Wisconsin
The oldest home among the five, a Prairie/Craftsman home built in 1925, sold for $1,100,000 at 2450 Commonwealth Avenue in Madison’s Dudgeon-Monroe neighborhood. The two-story stucco home sits on a corner lot of 6,534 square feet, and it has four bedrooms, three bathrooms and 3,049 square feet. It also has a deck, a partially finished full basement and an attached one-car garage. The property last sold for $211,300 in 2008.
Jennifer Hoyt of Realty Executives Cooper Spransy was the listing agent, and Nicole L Goggio, of the same brokerage, represented the buyer.
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No. 4 — $1,100,000 · N8594 Hay Hollow Rd, Blanchardville, Wisconsin
The largest piece of land in this week’s group, 14.84 acres of rolling countryside, comes with the home at N8594 Hay Hollow Road in Blanchardville, which also sold for $1,100,000. The rural property is set up for horses, with a barn of four stalls and an indoor riding arena, along with other outbuildings and storage.
The two-story contemporary home was built in 2009 in wood siding and stone and has four bedrooms, three bathrooms and 3,953 square feet. Its great room has 24-foot ceilings, windows that run from floor to ceiling and a stone gas fireplace. Granite counters, maple cabinets and maple floors are in the kitchen, along with Kohler fixtures.
Upstairs, a loft adds living space, and the primary suite is set apart from the other bedrooms. The walkout lower level is finished with a family room and wet bar, a full bath and the fourth bedroom. A two-car garage is attached. The property last sold for $550,000 in 2019.
Living In Madison Real Estate Group of Keller Williams Realty was the listing agent, and Lexie D Benson of EXIT Professional Real Estate represented the buyer.
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No. 5 — $1,025,000 · 5921 Thorstrand Rd, Madison, Wisconsin
A midcentury modern home at 5921 Thorstrand Road in Madison’s Old Middleton Greenway sold above its asking price of $995,000, closing at $1,025,000. Built in 1963 on a wooded drive, the home sits on 0.61 acres with seasonal views of the lake and deeded lake access, though no frontage of its own. The sale also included a partial share in a vacant lot with a trail to Spring Harbor.
Floor-to-ceiling windows look out on mature trees. The home has three bedrooms, three bathrooms and 2,923 square feet, with new wood floors and a remodeled primary bath. A foyer, two bedrooms and a full bath are on the entry level. Up a level are a great room with custom built-ins, a family room with a gas fireplace, a kitchen with a bright dining area and the primary suite. Several walkouts lead to the backyard, and the lower level has a rec room, an office and another full bath. A detached garage has room for two cars. The property last sold for $776,000 in 2022.
Chas Martin of Sprinkman Real Estate was the listing agent, and the Matt Winzenried Real Estate Team of Realty Executives Cooper Spransy represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 1, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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