The five highest-priced home sales reported in Sheboygan-Manitowoc Lakeshore, Wisconsin for the week ending November 8, 2026 came to a combined $3.434 million. Two of the homes are in Sheboygan Falls, two are in Sheboygan and one is in Reedsville, the lone Manitowoc County sale of the group.
Every one of the five has four bedrooms. The group includes three two-story homes and two ranches, built over more than four decades, from 1971 to 2014. In two of the sales, the same agent was on both sides.
No. 1 — $969,000 · 280 Settlers Circle, Sheboygan Falls, Wisconsin
The week’s top sale is a Colonial in the Pinehurst Meadows neighborhood of Sheboygan Falls, set on the fourth hole of The Bull at Pinehurst Farms, a Jack Nicklaus Signature golf course. It sold for $969,000.
Built in 2008, the two-story home has an exterior of stone, brick and wood siding, with 4,599 square feet of living space on a 0.59-acre lot. It has four bedrooms, four full baths and a half bath. The updated kitchen has white oak floors, an induction range and quartz countertops. The primary suite is on the main floor, and its bath is warmed by in-floor radiant heat. The finished lower level adds a kitchenette. Outside are a patio and an in-ground sprinkler system, and the neighborhood is minutes from Kohler and Sheboygan. The property last sold for $135,000 in 2008.
The Dave Didier Team of RE/MAX United – Port Washington was the listing agent, and the home went under contract seven days after it was listed. Tori Dietrich Torres represented the buyer.
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No. 2 — $720,000 · W2179 Shamrock Drive, Sheboygan Falls, Wisconsin
Along the Pigeon River in Sheboygan Falls, this ranch sits on 3.77 wooded acres, the largest lot among the five. Built in 1971, it is also the oldest of the group, and with 5,452 square feet of living space it is the largest home as well.
An indoor in-ground pool comes with a slide and a diving board, and the home also has a sauna, a private spa and a theater room. The main living spaces follow an open floor plan, and the finished lower level has walk-out access. Outdoors there is a basketball court, along with a patio, a barn and frontage on the river. The home has four bedrooms, three full baths, a half bath and a four-car attached garage.
Allianna Peterson of Century 21 Moves listed the home and also represented the buyer, so the same agent was on both sides of the sale.
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No. 3 — $625,000 · 5019 Wild Meadow Drive, Sheboygan, Wisconsin
Built in 2014, the newest home in this Top 5 is a ranch in the Green Meadows neighborhood of Sheboygan, on 0.73 acres with views across a pond. A hot tub on the property looks out over the water, and a deck and patio open the home to the yard.
Inside, a vaulted ceiling brings light into the open plan. The great room has a gas fireplace, the kitchen pairs custom cabinets with granite counters, and there is a generous dining area. The split-bedroom layout includes a primary suite with a private bath. Downstairs, the finished lower level has a bar, a family room and the fourth bedroom. The home has 3,454 square feet of living space, three full baths and a half bath, and it is a short drive to I-43. The property last sold for $37,500 in 2014.
The home sold at its full asking price of $625,000. The Brost Group of Keller Williams Empower was on both sides of the sale, as the listing agent and representing the buyer.
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No. 4 — $600,000 · 1611 Hollowbrook Court, Reedsville, Wisconsin
This contemporary in Reedsville sits on 2.12 wooded acres overlooking Seven Lakes Golf Course. From the deck, the home looks out to Holes 13 and 16, and the property also has pond frontage.
Built in 1993, the two-story home opens with a vaulted foyer rising two stories. The living room has an open staircase, a fireplace framed in brick and a wall of windows facing the golf course and the backyard. The kitchen, with a granite island, is open to the living and dining areas. The primary suite and a den or office are on the main floor, and three more bedrooms share a full bath upstairs. The lower level was newly refinished. The home has 2,575 square feet of living space, two full baths and a half bath. The property last sold for $493,000 in 2025.
The home went under contract two days after it was listed and sold for $15,000 above its asking price of $585,000. Libby Rhode of Keller Williams-Manitowoc was the listing agent, and Henry Grant represented the buyer.
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No. 5 — $520,000 · 911 Cobblestone Drive, Sheboygan, Wisconsin
In the Stonebridge Crossing neighborhood of Sheboygan, this 2001 home sits on a wooded 0.39-acre corner lot with mature trees and a deck. Its design draws on both Colonial and contemporary styles, and the property last sold for $268,000 in 2002.
A two-story foyer with a showcase staircase leads to formal living and dining rooms. The kitchen has an island and a pantry and opens to a dinette and a family room with a gas fireplace, while a laundry and mudroom are also on the main floor. Upstairs, the primary suite has a walk-in closet and a bath with dual sinks and a separate tub and shower, and three more bedrooms share a full bath. The home has 2,298 square feet of living space, four bedrooms, two full baths and a half bath. The unfinished lower level has a bath rough-in.
Matthew Kapellen of Pleasant View Realty, LLC was the listing agent, and the home went under contract two days after it was listed. Carter Maranell represented the buyer.
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