The Kennedy Sisters

Royal LePage Real Estate Services Ltd., Oakville

About Us

In 2007, we founded the Kennedy Sisters Team to help families like ours enjoy exceptional real estate experiences across the GTA West area. Since then, it has been our honour to assist countless clients with their real estate needs—always guided by our motto: “Let our family help your family.”

With deep roots in our community, we take great pride in supporting and sponsoring many local charities. Our dedication and hard work have earned us recognition as Lifetime Chairman’s Award winners—an honour reserved for the top 1% of Royal LePage agents across Canada

Meet Lesley and Stephanie

LESLEY KENNEDY

Principal Sales Representative
A strategist at heart and a powerhouse in the real estate world, Lesley Kennedy has been setting the bar for excellence since co-founding The Kennedy Sisters in 2006. With a background in marketing and hospitality—where she earned a coveted “Top 30 Under 30” award—Lesley brings a sharp business mindset, an unmatched eye for presentation, and a client-first approach that has fueled the team’s success.
Born and raised in Oakville, Lesley’s deep community ties and vast market knowledge make her an invaluable guide for buyers and sellers alike. She is known for her meticulous attention to detail, bold negotiation skills, and unwavering commitment to her clients. Whether it’s a multi-million dollar estate or a first home, she believes every property deserves top-tier service, innovative marketing, and expert staging to maximize value.
Driven, dedicated, and always two steps ahead, Lesley is more than a real estate agent—she’s a trusted advisor, problem-solver, and advocate who ensures every client’s journey is seamless from start to finish.

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STEPHANIE KENNEDY

Sales Representative | Partner
With a passion for design, a sharp eye for detail, and a relentless drive to deliver results, Stephanie Kennedy has been shaping exceptional real estate experiences since joining The Kennedy Sisters in 2009. Born and raised in Oakville, she combines local expertise with a deep understanding of architecture, staging, and strategic marketing to give her clients a distinct advantage.
Before real estate, Stephanie’s career took her around the world—first as a professional figure skater starring in Disney on Ice, then in hospitality at Glen Abbey Golf Club, where she mastered the art of client service. These experiences shaped her approach: precision, poise, and an unwavering commitment to excellence.
Stephanie is known for her ability to transform homes through expert staging, creating powerful first impressions that drive results. Whether preparing a property for market or helping buyers find the perfect space, she brings energy, insight, and a seamless, stress-free approach to every transaction.

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Learn more about The Kennedy Sisters

Current Listings

  • 111 Judith Crescent, Ancaster

    $2,339,000
    3 Bedrooms
    4 Bathrooms
    Singe-Family Home
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  • 5193 Lakeshore Road, Burlington

    $1,799,000
    4 Bedrooms
    3 Bathrooms
    Singe-Family Home
    More Details

  • 1274 Hilton Lane, Oakville

    $1,749,000
    4 Bedrooms
    4 Bathrooms
    Singe-Family Home
    More Details

  • 1544 Greenbriar Drive, Oakville

    $1,478,000
    3 Bedrooms
    3 Bathrooms
    Singe-Family Home
    More Details

  • 10 Normandy Place, Oakville

    $1,099,900
    3 Bedrooms
    3 Bathrooms
    Townhouse
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  • 1522 Tough Gate, Milton

    $1,089,900
    4 Bedrooms
    Singe-Family Home
    More Details

  • 1035 Southdown Road # 601, Mississauga

    $749,000
    2 Bedrooms
    2 Bathrooms
    Condo
    More Details