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Waterside Homes for Sale

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  • /59

    $969,900

    • 4 Beds
    • 3.5 Baths
    • 2,934 Sq Ft

    16712 Rusty Anchor Rd, Winter Garden, FL 34787

    Incredible MOVE-IN READY home in one of the most sought-after communities in one of the most desirable cities around Orlando! If you are looking for your dream home with easy access to downtown Orlando, Disney, and the charm of downtown Winter Garden, come see this 4 bedroom / 3.5 bathroom, 2,934 sq ft, 3-car garage, single story Waterside community home! Built in 2019, this home has been

    Dan Conlon HEIRLOOM REALTY INTERNATIONAL

    16712 Rusty Anchor Rd, Winter Garden, FL 34787
  • /57

    $514,999

    • 3 Beds
    • 2 Baths
    • 1,692 Sq Ft

    1559 Bayfront Park Alley, Winter Garden, FL 34787

    Welcome to 1559 Bayfront Park Alley, a refined Florida Contemporary home tucked inside the highly sought-after Waterside on Johns Lake community in Winter Garden, Florida. Built in 2018 and freshly painted inside and out in 2025, this meticulously maintained 3-bedroom, 2-bathroom home offers 1,692 sq ft of elevated living, surrounded by lush landscaping and framed by an extraordinary view of a

    Adrian Jiminez MARKET CONNECT REALTY LLC

    1559 Bayfront Park Alley, Winter Garden, FL 34787
  • /72

    $2,995,000

    • 7 Beds
    • 5.5 Baths
    • 6,250 Sq Ft

    16821 Broadwater Ave, Winter Garden, FL 34787

    Stunning Designer Home in Exclusive Gated Community Near Horizon West, Windermere, and Downtown Winter Garden. No detail was overlooked in this custom-upgraded 7-bedroom, 5.5-bath estate offering a rare combination of luxury-focused design, wellness-minded living, and high-function luxury. From bespoke ceiling and wall treatments to curated finishes in every room, this home showcases intentional

    Christy Knox KELLER WILLIAMS WINTER PARK

    16821 Broadwater Ave, Winter Garden, FL 34787
  • /39

    $650,000

    • 4 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    1565 Bayfront Park Alley, Winter Garden, FL 34787

    Exceptional opportunity! Nearly 3000 sqft home with fantastic floorplan in highly desirable Water Side on Lake Johns community. This home offers 4 bedroom, 3 full baths with a junior en suite bedroom downstairs which features a walk-in shower (no tub) and separate 1/2 bath for guests, 2 car attached garage, paver driveway, porches and sidewalks. Additional primary bedroom and secondary

    Dawn Briggs BLUE MAGNOLIA REALTY LLC

    1565 Bayfront Park Alley, Winter Garden, FL 34787
  • /60

    $1,825,000

    • 5 Beds
    • 5.5 Baths
    • 3,513 Sq Ft

    16761 Broadwater Ave, Winter Garden, FL 34787

    Welcome to 16761 Broadwater Avenue, a stunning lakefront estate nestled in the beautiful community of Winter Garden, FL. Situated on an expansive 20,282 sq ft lot, this 5-bedroom, 5.5-bathroom residence offers 3,633 square feet of thoughtfully designed luxury. As you arrive, a gated entry welcomes you into a charming open-air courtyard, setting the stage for the elegant experience that awaits

    Ben Whidden COMPASS FLORIDA LLC

    16761 Broadwater Ave, Winter Garden, FL 34787
  • /45

    $879,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 2,934 Sq Ft

    16696 Otterchase Ln, Winter Garden, FL 34787

    STUNNING EXECUTIVE HOME in the highly sought-after gated Waterside on Johns Lake community that is sure to impress! OVER $50K IN UPGRADES!!! Gorgeous and exceptionally maintained! Beautiful curb appeal on a nicely landscaped large lot with a freshly sealed driveway, walkway and front porch. Enter the home through the Italian-style walk through and courtyard. Your kitchen includes a gas cooktop

    Amy Moline EXP REALTY LLC

    16696 Otterchase Ln, Winter Garden, FL 34787

Frequently Asked Questions Why Live in Waterside

Is Waterside a good place to live?
Waterside is a good place to live. Waterside is considered very car-dependent and somewhat bikeable. Waterside is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. It has a median age of 38. The average household income is $210,364 which is above the national average. College graduates make up 69.7% of residents. A majority of residents in Waterside are home owners, with 6.4% of residents renting and 93.6% of residents owning their home. A local real estate agent serving Waterside can help you decide if this neighborhood is the right one for you. Learn more on our Waterside neighborhood guide.
Is Waterside, FL a safe neighborhood?
Waterside, FL is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
What are the best public schools in Waterside?
The best public schools that serve Waterside are:
What are the most popular zip codes in Waterside, Winter Garden, FL?
The most popular zip codes in Waterside, Winter Garden, FL include 34787, 34711, 34760, 34786 and 34756.
What are the most popular neighborhoods near Waterside, Winter Garden, FL?
The most popular neighborhoods near Waterside, Winter Garden, FL are Lake Avalon Groves, Stoneybrook West, Magnolia Pointe, Heritage Hills and Postal Colony.
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