12

Recently Sold Waterside Homes

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  • /2

    $560,000 Sold Jul 02, 2025

    • 2,476 Sq Ft
    • $226/SF
    • 25 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2018

    17084 Harbor Oak Pkwy, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. Welcome to this stunning two-story single-family home located in the sought-after Waterside community in Winter Garden. Featuring 4 spacious bedrooms and 3 full bathrooms, this beautifully maintained residence offers the perfect blend of comfort, style, and functionality.Step inside to an expansive open-concept layout ideal for entertaining.

    Nic Baker REDFIN CORPORATION

    17084 Harbor Oak Pkwy, Winter Garden, FL 34787
  • /2

    $620,000 Sold Jun 02, 2025

    • 2,078 Sq Ft
    • $298/SF
    • 14 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2017

    16959 Tradewind Point, Winter Garden, FL 34787

    FULLY-UPDATED, SINGLE-STORY HOME ON A PREMIUM LOT! No stone has been left unturned in this pristine, inviting Waterside home. You are greeted at the front entrance by meticulously cared-for, mature landscaping and solid wood front door. As you step inside, you immediately notice the upgraded wood-look tile flooring throughout the main living space, as well as the fine details such as the tray

    Sophia Ferrara COLDWELL BANKER REALTY

    16959 Tradewind Point, Winter Garden, FL 34787
  • /2

    $1,250,000 Sold May 09, 2025

    • 4,474 Sq Ft
    • $279/SF
    • 75 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2020

    16767 Rusty Anchor Rd, Winter Garden, FL 34787

    Rare opportunity. Property has $300,000 in UPGRADES! Located in the Waterside community, this property is on a larger than conventional lot with no direct rear neighbors, situated on a premium lot overlooking the dry retention pond. The Mansfield is the perfect two-story plan with 6 bedrooms, master suite downstairs, plus a full suite on the first floor. It also has an exclusive OFFICE and half

    Michelle Mira WRA BUSINESS & REAL ESTATE

    16767 Rusty Anchor Rd, Winter Garden, FL 34787
  • /2

    $717,500 Sold Jan 24, 2025

    • 3,183 Sq Ft
    • $225/SF
    • 121 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 2018

    17208 Ocean Hill Dr, Winter Garden, FL 34787

    GREAT PRICE FOR A GREAT HOME IN HIGHLY DESIRED LOCATION! Come see this BEAUTIFUL FIVE BEDROOM HOME WITH BEAUTIFUL BACKYARD, STUNNING KITCHEN AND BREAKFAST AREA WITH PLANTATION SHUTTERS ALL LOOKING OVER GORGEOUS LANDSCAPING and an expansive backyard to view the rolling hills. THEATER ROOM comes fully equipped with furniture, surround sound, TV and dark room window treatments! This stunning home

    Lori Gilmore LORI GILMORE REAL ESTATE LLC

    17208 Ocean Hill Dr, Winter Garden, FL 34787
  • /2

    $949,990 Sold Jan 23, 2025

    • 2,696 Sq Ft
    • $352/SF
    • 94 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2019

    16736 Rusty Anchor Rd, Winter Garden, FL 34787

    Introducing the exquisite Carlisle Plan, a beautiful single-story home featuring four bedrooms, three baths, and a spacious tandem three-car garage, located in the highly desirable gated community of Waterside on Johns Lake. This exceptional home is highlighted by a charming courtyard-style entry and a thoughtfully designed open-concept living space, which includes a great room, casual dining

    Nick Whitehouse RE/MAX PRIME PROPERTIES

    16736 Rusty Anchor Rd, Winter Garden, FL 34787
  • /2

    $1,210,000 Sold Dec 13, 2024

    • 4,474 Sq Ft
    • $270/SF
    • 38 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2020

    16711 Otterchase Ln, Winter Garden, FL 34787

    Welcome home to this pristine property nestled behind the charming gated entrance of Waterside on Johns Lake. You will be greeted by stunning curb appeal, featuring a Mediterranean-style design with a paver driveway, a spacious three-car garage, and beautiful landscaping. The Mansfield model is the perfect two-story layout with 6 bedrooms, including a master suite on the main floor and additional

    Morgan Horsley THE REAL ESTATE COLLECTION LLC

    16711 Otterchase Ln, Winter Garden, FL 34787
  • /100

    $1,160,000 Sold Oct 24, 2024

    • 3,597 Sq Ft
    • $322/SF
    • 21 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2019

    16702 Otterchase Ln, Winter Garden, FL 34787

    *INCLUDED Tesla solar is PAID in FULL! Properly named “Waterside”, this luxurious gated community was created to savor the shoreline along Johns Lake. Stunning resort style amenities are perched high above the waters edge to fully experience the natural beauty. A perfect escape to enjoy a swim & daily workout in the fitness center. Classic mediterranean architecture keeps the community cohesive

    Autumn Makin LAKEFIELD REALTY GROUP LLC

    16702 Otterchase Ln, Winter Garden, FL 34787
  • /2

    $1,350,000 Sold Sep 23, 2024

    • 4,708 Sq Ft
    • $287/SF
    • 3 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 2016

    16844 Broadwater Ave, Winter Garden, FL 34787

    Welcome to your dream home, nestled behind the charming gated entrance of Waterside on Johns Lake. This 4,700 sq ft beauty exudes warmth and elegance the moment you step through its doors. From the street, you'll be greeted by a striking brick façade, a tile roof, and an expansive driveway leading to a spacious 35x24 three-car garage with pristine finished floors and ample storage. As you enter

    Kimberley Beaudry ORLANDO REGIONAL REALTY

    16844 Broadwater Ave, Winter Garden, FL 34787
  • /2

    $1,250,000 Sold Sep 19, 2024

    • 4,549 Sq Ft
    • $275/SF
    • 12 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2019

    16778 Rusty Anchor Rd, Winter Garden, FL 34787

    Nestled in the quiet, gated community of Waterside on Johns Lake, 16778 Rusty Anchor Road showcases the stunning Sutherland model by Cal Atlantic Homes offering an unparalleled living experience. This residence, with its striking French Country elevation, boasts a stack stone exterior, a barrel tile roof, and a brick paver driveway leading to an oversized 3-car garage with no rear neighbors. The

    Nick Whitehouse RE/MAX PRIME PROPERTIES

    16778 Rusty Anchor Rd, Winter Garden, FL 34787
  • /2

    $1,148,000 Sold Aug 22, 2024

    • 3,776 Sq Ft
    • $304/SF
    • 102 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2019

    16832 Broadwater Ave, Winter Garden, FL 34787

    Step into luxury with this stunning 5 bedroom, 4 and a half bath home in one of Winter Garden's Finest Gated Communities. Starting with the amazing curb appeal, the Mediterranean style home offers a paved driveway, 3 car garage and beautiful landscaping. Walk in the welcoming open spacious floor plan, complete with beautiful high end finishes of oversized tile floors, wood planked, railed

    Melissa Wilson KELLER WILLIAMS REALTY AT THE LAKES

    16832 Broadwater Ave, Winter Garden, FL 34787
  • /2

    $498,000 Sold Jul 29, 2024

    • 2,106 Sq Ft
    • $236/SF
    • 195 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2018

    17008 Tradewind Point, Winter Garden, FL 34787

    Beautiful Corner Single family home 3 Bedrooms/ 3 Bathrooms. The house has a nice distribution, open floor plan concepts, Master and second Bedroom downstairs and an independent 3rd Bedroom upstairs with a loft. Executive kitchen,Beautiful TV stone wall, all lamps upgraded! Screen porch and patio fenced. Purifier water system located at the garage. The Property has an amazing

    Marcia Huerta ROBERT SLACK LLC

    17008 Tradewind Point, Winter Garden, FL 34787
  • /2

    $2,315,625 Sold Jul 09, 2025

    • 4,462 Sq Ft
    • $519/SF
    • 6 Beds
    • 4.5 Baths
    • Built 2019

    16719 Broadwater Ave, Winter Garden, FL 34787

    Gorgeous Lake Front Winter Garden Pool Home!

    Stellar Non-Member Agent Stellar Non-Member Office

    16719 Broadwater Ave, Winter Garden, FL 34787

Frequently Asked Questions Why Live in Waterside

What is the average time to sell a house in Waterside, FL?
The houses for sale in Waterside, FL spend an average of 45 days on the market.
What is the number of active homes for sale in Waterside, FL?
There are 3 active homes for sale in Waterside, FL.

Home Trends in Waterside, FL

Housing Trends

Median Sale Price
$1,154,000
Median Single Family Sale Price
$1,160,000
Average Price Per Sq Ft
$319
Number of Homes for Sale
3
Last 12 months Home Sales
12
Months of Supply
3.00
Median List Price
$1,225,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
68%
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