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Waterside Homes for Sale

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  • /59

    $949,900

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

    16712 Rusty Anchor Rd, Winter Garden, FL 34787

    Significant PRICE IMPROVEMENT! Owners very motivated! 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, the charm of downtown Winter Garden (and Farmers Market on Saturdays), and FL-429, come see this 4 bedroom / 3.5 bathroom, 2,934 sq

    Dan Conlon HEIRLOOM REALTY INTERNATIONAL

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

    $489,999 Open Fri 2PM - 5PM

    • 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
  • /30

    $475,000

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

    17047 Harbor Oak Pkwy, Winter Garden, FL 34787

    Welcome to 17047 Harbor Oak Parkway in the highly sought-after Waterside Community of Winter Garden! This 3-bedroom, 2-bath residence is a true gem, offering an unparalleled combination of comfort, style, and convenience. Step inside and be greeted by tall ceilings and an open floorplan perfect for entertaining with tons of natural light. Towards the front of the home, you'll find the primary

    Jenna Palmero COLDWELL BANKER REALTY

    17047 Harbor Oak Pkwy, 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
  • /59

    $1,749,000

    • 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

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.
How much do you need to make to afford a house in Waterside?
The median home price in Waterside is $1,137,500. If you put a 20% down payment of $227,500 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $5,790 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $248K a year to afford the median home price in Waterside. The average household income in Waterside is $210K.
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, 34760, 34711, 34786 and 34714.
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.

Home Trends in Waterside, FL

Housing Trends

Median Sale Price
$1,160,000
Median Single Family Sale Price
$1,250,000
Average Price Per Sq Ft
$331
Number of Homes for Sale
5
Last 12 months Home Sales
13
Months of Supply
4.60
Median List Price
$1,137,500
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
71%
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