Reimagined Wisconsin Lakefront Estate With a Hillside Trolley Lists for $6,990,000

The seven-acre Okauchee Lake retreat in Nashotah has been transformed inside and out, pairing 120 feet of frontage and a private dock with a pickleball court, detached entertaining space and a trolley connecting the hillside property.

At W335N5511 Island View Lane in Nashotah, Wisconsin, getting down toward the lake doesn’t necessarily mean taking the stairs. A hillside trolley is among the more unusual features of the seven-acre estate, connecting a property that descends toward 120 feet of frontage on Okauchee Lake.

The five-bedroom house itself dates to 1988, but its current appearance tells a more recent story. According to the listing, the 7,608-square-foot residence has been “completely transformed to the standards of a custom new build inside and out,” with extensive work extending beyond the house to landscaping and outdoor entertaining areas.

The property is now asking $6,990,000 after debuting in August at $8,250,000. The Sept. 23 reduction of $1,260,000, or about 15.3%, comes only months after the estate changed hands for $2,740,000 in February.

That compressed timeline makes the renovation central to understanding the new price. Listing agent Rebecca Thomas of Keller Williams–Lake Country describes “every inch” of the property as having been thoughtfully reimagined, though the supplied listing doesn’t disclose the renovation budget or provide an itemized scope of work.

Seven Acres Meet 120 Feet of Okauchee Lake

The property’s scale is unusual for a lake house.

Approximately seven private acres extend behind the residence, while 120 feet of frontage connects it directly with Okauchee Lake. The site is oriented toward sunset views, making the western light over the water a recurring backdrop to the outdoor spaces.

A private dock provides direct lake access. Multiple terraces create separate areas for gathering closer to the house and along the sloping grounds, while extensive new landscaping ties the different elevations together.

It is that topography that gives the hillside trolley a practical role rather than making it simply a novelty. On a large lakefront site where the house and shoreline sit at different elevations, mechanized transportation can make movement between entertaining areas and the water considerably easier.

The listing doesn’t specify the trolley’s length, capacity or mechanical system, so those details shouldn’t be inferred. What is established is that it forms part of an unusually extensive outdoor program for the property.

A 1988 House Reworked as a Modern Luxury Home

The residence was originally built in 1988, but the current listing positions it as something fundamentally different from a lightly renovated older lake house.

Its transformation is described as comprehensive, encompassing the interior and exterior and intended to bring the property to “the standards of a custom new build.” The finished residence now spans approximately 7,608 square feet with five bedrooms and five bathrooms.

The supplied description doesn’t identify the architect, interior designer, builder or individual kitchen and bathroom specifications. Nor does it quantify how much of the original structure was retained. It would therefore be premature to characterize the project as a reconstruction or new residence despite the listing’s comparison with new-build standards.

What can be said is that the work appears to extend substantially beyond cosmetic remodeling. New landscaping and newly conceived outdoor areas form part of the same transformation, creating a more unified estate rather than limiting the investment to interior finishes.

For a property of this age, that distinction matters. The appeal is intended to combine an established seven-acre lakefront site with the experience of a substantially refreshed contemporary residence.

The Entertaining Space Doesn’t Stop at the Main House

One of the more intriguing elements sits apart from the primary residence.

The property includes what the listing describes as a “beautifully appointed detached entertaining space.” Details about its square footage and interior configuration aren’t supplied, so it shouldn’t be characterized as a guest house or separate residence without further information.

Its stated purpose, however, reinforces the estate’s emphasis on gatherings. Rather than asking the 7,608-square-foot main house to contain every recreational function, the property distributes activity across separate structures and outdoor spaces.

There is also a detached 3.5-car garage in addition to the residence. The listing doesn’t specify the total garage capacity across the entire property or whether the detached structure includes workshop or storage areas beyond vehicle parking.

That combination of separate buildings becomes more useful on seven acres than it might on a compact suburban parcel. Entertaining, vehicle storage and lake recreation can occupy distinct areas without being compressed against the main house.

Pickleball Joins the Lakefront Amenities

The outdoor recreation program isn’t confined to Okauchee Lake.

A dedicated pickleball court provides a land-based counterpart to boating and other waterfront activities. Multiple entertaining terraces, meanwhile, allow different groups to gather across the property without relying on a single oversized patio.

The private dock establishes the most direct connection to the lake, while the hillside trolley provides another means of navigating the grounds. Together, the features suggest a property designed around movement between the house, recreation areas and shoreline.

The extensive new landscaping is important in that context. On a sloping seven-acre site, landscape design can determine whether outdoor amenities feel like unrelated additions or parts of one coherent estate.

Thomas’s listing calls the result “an extraordinary lakefront retreat designed for unforgettable gatherings and generations of memories.” The more concrete story behind that language is a large lakefront site where a substantial renovation has been paired with multiple dedicated recreational spaces rather than concentrated solely inside the house.

Readers can explore the complete photography, current availability and additional property details through the Zillow listing here.

From $2,740,000 to $8,250,000 in Six Months

The property’s recent price history is particularly notable.

Before the current transformation, the estate came to market in March 2025 at $4,499,998. Its asking price was subsequently adjusted several times, reaching $3,099,000 in November 2025 after earlier pending periods.

The property ultimately sold for $2,740,000 on Feb. 2, 2026.

Six months later, on Aug. 9, it returned to the market asking $8,250,000—$5,510,000 above the February sale price, or approximately 201.1% higher.

That does not mean the property appreciated 201.1% in six months.

The current listing explicitly says the estate has been completely transformed inside and out, and identifies extensive new landscaping among the improvements. The scale of the difference between the February transaction and August asking price therefore has to be considered in the context of that intervening work.

However, the supplied information doesn’t state when all of the renovation work occurred, how much was spent, or precisely which improvements were completed after the February purchase. Without those details, it isn’t possible to separate renovation investment from the seller’s pricing expectations or any change in underlying land and lakefront value.

A $1,260,000 Price Cut Brings the Ask to $6,990,000

The latest adjustment provides another piece of the pricing story.

On Sept. 23, the asking price was reduced from $8,250,000 to $6,990,000. The $1,260,000 cut represents approximately 15.3% of the original August asking price.

At $6,990,000, the property remains $4,250,000 above its $2,740,000 February sale, a difference of approximately 155.1%. Again, that spread should not be interpreted as appreciation because a substantial transformation is represented as having occurred around this period.

Based on the stated 7,608 square feet, the current asking price equates to approximately $919 per square foot. The August $8,250,000 price represented roughly $1,084 per square foot.

Neither calculation fully captures the property’s economics. Seven acres, 120 feet of Okauchee Lake frontage, a private dock, detached entertaining structure, separate 3.5-car garage, pickleball court, landscaping, terraces and hillside trolley all sit outside a simple house-area calculation.

The pricing therefore represents a test not merely of what buyers will pay for 7,608 square feet, but of how the market values a comprehensively reworked lakefront compound with substantial acreage.

The Land May Be the Hardest Part to Recreate

New kitchens, bathrooms and interiors can be built almost anywhere. Seven private acres with 120 feet on an established recreational lake are considerably more dependent on geography.

That distinction helps explain the underlying proposition at W335N5511 Island View Lane. The renovation seeks to give an older residence the finish and experience of a newer luxury property without surrendering the mature lakefront setting that came with the original estate.

The pickleball court, detached entertaining space and multiple terraces can be understood in the same way. They turn the acreage into usable parts of the property rather than leaving most of it as scenery.

The hillside trolley may be the clearest symbol of that approach. It is an amenity, but it also solves a problem created by one of the site’s defining characteristics: the descent toward Okauchee Lake.

At $6,990,000, the result is a lake house whose story is as much about what happened recently as what was built in 1988—a substantial transformation of an established waterfront property, now returning to the market at a markedly different price point.

Property Overview

W335N5511 Island View Lane in Nashotah, Wisconsin, is offered at $6,990,000. Built in 1988 and subsequently extensively transformed, the approximately 7,608-square-foot residence has five bedrooms and five bathrooms on roughly seven acres.

The property has approximately 120 feet of Okauchee Lake frontage with sunset views and a private dock. Outdoor and recreational amenities include a pickleball court, multiple entertaining terraces, extensive new landscaping and a hillside trolley.

A detached entertaining space provides an additional gathering area away from the main residence, while a separate 3.5-car garage adds vehicle and storage capacity.

The estate sold for $2,740,000 in February 2026 before returning to the market at $8,250,000 in August. Its asking price was reduced by $1,260,000 to $6,990,000 on Sept. 23, 2026. Because the current listing describes a comprehensive transformation of the property, those figures should not be treated as a straightforward measure of appreciation.

Listing Representation

Rebecca Thomas of Keller Williams–Lake Country represents W335N5511 Island View Lane.

Thomas’s listing describes the residence as having been “completely transformed to the standards of a custom new build inside and out,” emphasizing the combination of extensive private acreage, Okauchee Lake frontage and newly reimagined recreational and entertaining spaces.

Rebecca Thomas
Keller Williams–Lake Country
Phone: 262-408-8923