A house built in 2009 in the Indian Hills area of Elm Grove sold for $3.75 million, the highest-priced home sale reported in the Milwaukee, Wisconsin metro area for the week ending August 16, 2026.
The week’s five highest-priced reported sales combined for $12.80 million and are spread across Indian Hills, Pewaukee, Shorewood, Hartland and Elm Grove, with Elm Grove turning up at both the top and the bottom of the ranking.
The five houses date from 1926, 1971, 1995, 2009 and 2025, and lake frontage comes with both the Pewaukee and the Hartland property.
No. 1 — $3,750,000 · 1500 Sunset Drive, Elm Grove, Wisconsin
1500 Sunset Drive, in the Indian Hills area of Elm Grove, sold for $3,750,000 on August 14, 2026, the highest reported price in the metro that week. The house dates from 2009 and is recorded at five bedrooms, six bathrooms and a reported 13,598 square feet.
Detailed listing remarks were not available for this sale, so the entry stays with the publicly reported record. The property previously changed hands for $2,900,000 in 2023.
Double Boldt Real Estate Team* of Keller Williams-MNS Wauwatosa was the listing agent. The $3,750,000 closing ranked No. 1 in RealtyWire’s Top 5 reported home sales for the Milwaukee, Wisconsin metro area for the week ending August 16, 2026.
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No. 2 — $2,500,000 · W277N3016 Rocky Point Road, Pewaukee, Wisconsin
W277N3016 Rocky Point Road in Pewaukee recorded an August 14, 2026 closing at $2,500,000. The 1995 house carries 86 feet of Pewaukee Lake frontage and is recorded at four bedrooms, four bathrooms and a reported 4,539 square feet.
The house has two primary suites: one on the first floor with views of the lake, the second upstairs and fully updated with a walk-in shower and a soaking tub. The remaining bedrooms open onto an indoor balcony above a floor-to-ceiling wood-burning brick fireplace, with the lake beyond. An updated kitchen, a laundry room and a dining area off the kitchen share the first floor with a separate formal dining room, and a walk-out lower level adds a second kitchen, a full bathroom and a recreation area opening onto a patio.
The property previously changed hands for $482,500 in 2012.
Cherie Jarchow of Milwaukee Executive Realty, LLC was the listing agent. The $2,500,000 closing put Jarchow at the listing side of the metro’s second-highest reported sale of the week.
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No. 3 — $2,350,000 · 3565 N Lake Drive, Shorewood, Wisconsin
3565 N Lake Drive in Shorewood, a French Provincial house built in 1926, sold for $2,350,000 in a closing dated August 14, 2026. A grand foyer opens into interiors with 15-foot ceilings and rich millwork.
A sunken living room flows into the dining room, where French doors open to a patio and landscaped yard. The kitchen centers on a custom island with high-end appliances. The primary suite sits down a private hall, with a dressing room and a newly remodeled ensuite bath finished with Waterworks fixtures, custom tile, a soaking tub and custom cabinetry.
Three guest bedrooms follow, one with an ensuite bath and two sharing a Jack-and-Jill bath, with two more bedrooms and a bath over the garage. A wine cellar, a lower-level recreation room and a walk-up attic with a cedar closet round out a house recorded at six bedrooms, five bathrooms and a reported 6,067 square feet. The property previously changed hands for $825,000 in 2011.
Bradley and Team* of Compass RE WI-Northshore was the listing agent. The house went under contract the same day the current listing went live and closed $351,000 above its final asking price of $1,999,000, the No. 3 sale in the week’s Milwaukee ranking.
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No. 4 — $2,300,000 · W322N6797 Wildwood Point Road, Hartland, Wisconsin
W322N6797 Wildwood Point Road in Hartland closed at $2,300,000 on August 13, 2026. The 1971 ranch has 100 feet of sand frontage on the east shore, where the water deepens gradually, and it is recorded at four bedrooms, three bathrooms and a reported 2,250 square feet.
The updated main kitchen has granite counters and custom alder cabinetry and looks into a living room with a vaulted ceiling and a lakeside deck. The primary bedroom has an adjacent full bath and a gas fireplace. A finished walk-out lower level holds guest quarters, with a family room and natural fireplace, a second kitchen, a full bath, a bedroom and a private patio. A recently installed tram runs down to the swimming beach, the pier, a boat and storage shed and a picnic area with a fire pit.
Tim Michelic of Realty Executives – Integrity was the listing agent. The property went under contract 19 days after the current listing date and closed $50,000 above its final asking price of $2,250,000, ranking No. 4 among reported home sales in the metro for the week.
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No. 5 — $1,900,000 · 1055 Red Barn Lane, Elm Grove, Wisconsin
The ranking finishes back in Elm Grove, where 1055 Red Barn Lane recorded an August 11, 2026 closing at $1,900,000. Listing materials identify Miller Marriott as the builder of the custom home, which was completed in 2025.
The custom kitchen opens directly to the great room, and four bedrooms sit upstairs, among them a primary suite with heated bathroom floors. The finished lower level adds a recreation room, an exercise room and a custom wine cellar. Other features include an integrated Sonos sound system, custom millwork, enhanced air-quality systems, an insulated garage and EV charger readiness. The house is recorded at four bedrooms, four bathrooms and a reported 4,341 square feet.
Sewart Group* of Compass RE WI-Northshore was the listing agent. The sale closed $1,000 above its final asking price of $1,899,000 and ranked No. 5 in RealtyWire’s Milwaukee Top 5 for the week, giving Compass RE WI-Northshore a second listing credit in the ranking alongside the Shorewood closing at No. 3.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 16, 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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