2015 to 2022Years built
2,050 to 4,450 sq ftHome size
GatedEntry
Johns Lake & Black LakeArea
Why people move here

A gated Johns Lake community with 34 lakefront homesites.

Waterside is a gated luxury community on Johns Lake, just west of Avalon Road off Marsh Road. Of its homesites, 34 sit directly on the lake and 105 are interior, with homes built from 2015 to 2022 and four to five bedroom plans.
Inside the gate: a community pool and pavilion, a fitness center, a playground, trails and a dock. It includes two neighborhoods, The Landings and The Strand. For buyers who want a gated lakefront home in Winter Garden, Waterside is near the top of the list.
Upsizers who want a gated lakefront home.

Waterside Winter Garden at a glance

Location: Marsh Rd & Harbor Oak Way, just west of Avalon Rd

Builder: Custom and individual builders

Built: 2015 to 2022

Homes: 34 lakefront, 105 interior

Home types: Single-family homes

Size: About 2,050 to 4,450 sq ft

Bedrooms: Varies by floor plan

Entry: Gated

Area: Johns Lake & Black Lake

Life here

What Waterside Winter Garden has

🏊Community pool and pavilion
🏋Fitness center
🛠Playground
🚲Trails
⚓Dock
🌊Johns Lake
Proximity

What is close to Waterside Winter Garden

  • Stoneybrook West Village Shopping Center with Publix Grocery ~1 mi
  • Winter Garden Village Retail Shopping Center with Super Target ~3 mi
  • West Orange Trail ~5 mi
  • Downtown Orlando ~19 mi

Approximate distances from the community entrance. Walt Disney World is roughly 15 to 20 minutes away off-peak. SR 50, the 429 interchanges and Avalon Road back up at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 Hamlin Elementary

🏫 Hamlin Middle

🏫 West Orange High

Orange County Public Schools. Zoning changes, so verify every address.

The numbers

Waterside Winter Garden market snapshot

$676,500Median sale priceDown 2.8% from $696,250 the year before.
44 daysDays on marketMedian cumulative days on market.
32Closed sales20 the year before.
98%Sale-to-list price ratioMedian for the last 12 months.

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 16, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Waterside Winter Garden homes for sale right now

Straight from Stellar MLS. Save the search and get new Waterside Winter Garden listings the day they hit.

Start of list of properties

Free guides

Buying or selling in Waterside Winter Garden?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Waterside Winter Garden works, from new construction versus resale to what to verify on HOA, CDD and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Waterside Winter Garden FAQ

Where is Waterside Winter Garden in Winter Garden?

Waterside Winter Garden is in south Winter Garden near Johns Lake and Black Lake, at Marsh Rd & Harbor Oak Way, just west of Avalon Rd.

How far is Waterside Winter Garden from Walt Disney World?

Roughly 15 to 20 minutes off-peak from this part of Winter Garden. I will map the exact drive from the entrance before you choose.

When were homes in Waterside Winter Garden built?

2015 to 2022. Most homes were built by individual or custom builders.

What amenities does Waterside Winter Garden have?

Community pool and pavilion, Fitness center, Playground, Trails, Dock, Johns Lake.

Is Waterside Winter Garden a gated community?

Yes. Waterside Winter Garden has a gated entry. I confirm gate type and access rules for any home before you write an offer.

What schools serve Waterside Winter Garden?

Schools commonly listed for this community: Hamlin Elementary, Hamlin Middle, West Orange High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Waterside Winter Garden inside Winter Garden city limits?

Many homes with a Winter Garden 34787 address, including much of Horizon West, sit in unincorporated Orange County rather than the City of Winter Garden. Taxes, utilities and services differ, so I confirm the jurisdiction for every address.

What do homes in Waterside Winter Garden sell for?

Per Stellar MLS, the median sale price in Waterside Winter Garden was $676,500 across 32 closed sales in the 12 months ending September 30, 2026. Call or text me at 407.502.4719 for recent sales that match your home.

Your next step

Thinking about Waterside Winter Garden?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Waterside Winter Garden, straight from Stellar MLS
  • City or county, HOA and CDD for the homes that fit
  • Your real commute, mapped from the entrance

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify city or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.