Every summer, HIDEAWAYS looks forward to a cherished tradition: touring the lakes of Muskoka with Sandy and Samantha Waldie. Over the years, the pages of HIDEAWAYS have followed the Waldie Girls, as they are often affectionately called, through some of the region’s most captivating properties—homes steeped in history, character, and architectural distinction.
With a discerning eye for detail and an intuitive grasp of the region, Sandy and Samantha have long been trusted guides to Muskoka’s most extraordinary real estate. Their approach blends narrative depth and evocative imagery with a respect for personal relationships that has earned them a reputation as thoughtful stewards of these treasured properties as they pass from one owner to the next.
Since 2017, HIDEAWAYS has joined forces with Sandy and Samantha to showcase the unique charm of the area through memorable feature stories captured in titles such as The Hamptons Meets Muskoka (2019), Touching History (2020), Memories Made (2021), There’s No Place Like Home (2023), and Classic Beauties (2024).
Readers may remember some of the standouts from past editions, including a storied Great House on a Lake Muskoka island famed for featuring the largest single pane of glass in Muskoka, a romantic lakeside cottage originally constructed as a wedding gift from an industrial magnate to his daughter, or a boathouse celebrated in the early 1900s as the site of epic live-band dance parties. And who could forget the legend of a legacy Muskoka family cottager who built his own lakeside skinny dip cabin.
What a treat it has been to learn about those unforgettable Rosseau, Joseph, and Muskoka estates—reminders of a romantic bygone era—with their signature features, including basswood interiors, wide-plank maple floors, and wicker-lined sunrooms—nestled against a backdrop of sweeping gardens, winding flagstone paths, and windswept rocky points.
And while heritage properties have a special place in their hearts, many of Sandy and Samantha’s remarkable listings have been modern builds—custom-designed hideaways designed to offer the finest amenities in contemporary style—where stories and histories will be written as the years go by.
Their instinct for storytelling doesn’t come from nowhere. Sandy and Samantha’s grasp of Muskoka is the result of many years living in and exploring it—following their own curiosity into the archives of Muskoka’s communities, diving deep into property histories, boating on the lakes, and walking the shorelines embracing their individual intricacies.
Their passion for beautiful narratives and evocative imagery is a part of their unique brand and style—and a key to their success. “We do our best to paint a picture of the properties we represent,” explains Sandy, “so that a new family can see themselves not just in a building or on a parcel of land, but in a place where delightful stories flourish.”
That being said, there is a substantial practical element to their business, and Sandy and Samantha have the utmost respect for the importance of transactions as significant as those involving real estate. They take seriously their duty to protect the interests of their clients, whether sellers or buyers.
Since the late 1980s, Sandy has helped shape the region’s real estate landscape with her steady hand and unflinching integrity. With a degree in economics from Queen’s University, Sandy has a sharp fiscal eye and zealously follows marketplaces globally and nationally, ascertaining their impact on her Muskoka clientele. She and Samantha’s shared understanding of its fluctuations in the geopolitical environment of the day allow them to position the properties and clients they represent in ways that are relative to the market now and sensitive to its expected trajectory in the months to come.
Sandy and Samantha continue to evolve their business with a future-forward ethos—each bringing the best communication strategies of their generation into the mix. As a millennial, Samantha ensures their listings are not only beautifully crafted but presented across digital platforms and social channels in the formats most likely to reach their prospective buyers. For her part, Sandy caretakes the personal touch as a means of honouring the core value of their business: to serve their clientele with care and respect for the journey they’re on. “Technology and social media are very important for businesses these days,” says Samantha, “but we never want to get disconnected from the clients we represent.”
“I tend to take the time to call or sit with someone instead of texting or emailing,” says Sandy. For 29 years, Sandy has held the distinction of being the top-performing agent at Chestnut Park Real Estate in Muskoka—a recognition that speaks as much to her knowledge and professionalism as to the trust she, and Samantha, have earned among their clients and colleagues alike.
This summer, Sandy and Samantha add an exciting Hideaways listing on Lake Rosseau (pictured on this page). On the market for the first time since the mid-twentieth century, the mainland waterfront landbank includes a toddler-friendly swimming bay, two sizable picnic islands, an authentic Muskoka summer cottage, and some of the best views in the coveted and rarely offered Windermere corridor.
Chestnut Park Real Estate Limited, Brokerage
110 Medora Street, P.O. Box 444, Port Carling, Ontario P0B 1J0
Sandy: Cell (705) 646-4747 • Office: 705-765-6878 • [email protected]
Samantha: Cell (705) 706-3350 • Office: 705-765-6878 • [email protected]
