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Waterside Homes for Sale

16936 Tradewind Point, Winter Garden image
16936 Tradewind Point, Winter Garden $645,000

~Seller may consider buyer concessions if made in an offer~Prepare to fall in love with this BEAUTIFULLY MAINTAINED 4-bedroom, 3.5 bath home in the highly sought-after Wa...

  • 4 Beds
  • 4 Baths
  • Waterside/Johns Lake Ph 2a SubDv.
  • 34787 Zip Code
17059 Harbor Oak Parkway, Winter Garden image
17059 Harbor Oak Parkway, Winter Garden $620,000 ▼

Motivated Seller! Don't miss your opportunity with this Winter Garden home - offering elegance, convenience and affordability. Situated inside the desirable Waterside c...

  • 4 Beds
  • 3 Baths
  • Waterside/Johns Lake Ph 2a SubDv.
  • 34787 Zip Code
1431 Viscaya Cove Boulevard, Winter Garden image
1431 Viscaya Cove Boulevard, Winter Garden $499,900 ▼

Welcome to this beautifully designed 2022-built home freshly painted, move in ready and located in the highly sought-after Waterside at Johns Lake community in Winter Gar...

  • 4 Beds
  • 3 Baths
  • Waterside/Johns Lake Ph 2c SubDv.
  • 34787 Zip Code
17035 Harbor Oak Parkway, Winter Garden image
17035 Harbor Oak Parkway, Winter Garden $485,000 ▼

Motivated sellers! Welcome to this highly sought-after home in the infamous Waterside Johns Lake. This adorable 3-bedroom, 2-bath home is truly a gem! This freshly painte...

  • 3 Beds
  • 2 Baths
  • Waterside/Johns Lake Ph 2a SubDv.
  • 34787 Zip Code
Home › Winter Garden › Waterside
📋 What's on This Page
  • About Waterside Neighborhood
  • Location & Connections
  • Neighborhood Amenities & Lifestyle
  • How Waterside Compares
  • HOA Information
  • Frequently Asked Questions
  • Available Homes

Waterside Homes for Sale

Winter Garden, FL 34787 | Gated CalAtlantic Lakefront Community on Johns Lake — Three Sub-Sections, Resort Amenities

Waterside is a gated lakefront community on the south shore of Johns Lake in Winter Garden, built by CalAtlantic Homes (now Lennar) between roughly 2015 and 2022 across three distinct sub-sections — The Landings, The Strand, and The Cove. Homesites range from interior pond-view lots to direct lakefront on Johns Lake, with resort-style amenities including a clubhouse, fitness center, swimming pool, pavilion, walking trails, and a community dock. View Available Homes

✔ Information verified current as of May 23, 2026

About Waterside Neighborhood

Waterside sits on the southern shoreline of Johns Lake — a 2,439-acre lake spanning the Orange and Lake County line — along Marsh Road just west of Avalon Road (CR-545). The community is part of west Winter Garden's lake corridor, positioned south of Stoneybrook West and west of the SR-429 expressway. Entry is gated, with separate access points for each of the community's three sub-sections.

The community is organized into three distinct sub-sections, all sharing the same amenity package but with different home types and price tiers. Waterside — The Landings is the largest section with over 130 homesites and is anchored by three internal ponds; floor plans here generally range from roughly 2,696 to 5,591 square feet, with 41 pond-view homesites and 34 direct Johns Lake lakefront lots. Waterside — The Strand is the luxury tier, with homes from approximately 2,937 to over 8,600 square feet — original CalAtlantic pricing on The Strand started above $1 million, and the section includes some of the most desirable lakefront lots on Johns Lake. Waterside — The Cove is the smaller third section, also built by CalAtlantic with comparable construction standards.

Internal streets include Harbor Oak Parkway, Viscaya Cove Boulevard, Broadwater Avenue, and Williams Road, which connect the sub-sections to the main amenity center off Marsh Road. The community's architectural standards favor stucco-and-tile Mediterranean and transitional designs typical of mid-2010s Florida luxury production, with tile roofs, paver driveways, three-car garages on most floor plans, and lanais oriented toward lake or pond views where possible.

Waterside's defining feature is its direct access to Johns Lake — a large ski lake that supports waterskiing, wakeboarding, fishing, and recreational boating, with a community dock available to all residents regardless of whether their individual homesite is lakefront. The combination of gated entry, resort-tier amenities, and shared lake access (not just lakefront-only) distinguishes Waterside from neighboring communities where lake access is restricted to lakefront homeowners.

📊 Quick Facts
Property Style(s):Single-family homes (Mediterranean / transitional)
Home Sizes:~2,696 – 8,600+ sq ft (varies by sub-section)
Bedrooms:4 – 5 (The Strand: up to 7+ bedrooms in select floor plans)
Bathrooms:3 – 7
Year Built:Approximately 2015 – 2022
Builder:CalAtlantic Homes (now Lennar) / Standard Pacific
Sub-Sections:The Landings, The Strand, The Cove
HOA Fee:Contact us for current fee
CDD Fee:None confirmed — verify with Orange County records
Lake Access:Community dock on Johns Lake (all residents)
Gated:Yes — separate gates per sub-section
🏡 What Makes Waterside Distinct
  • Three-tier community structure. Most lakefront communities are single-section. Waterside's three sub-sections let buyers choose price tier and home size without leaving the same amenity package, gate, and lake access.
  • Lake access without lakefront premium. The community dock on Johns Lake is shared by all residents — interior and pond-view homes still get full lake access for boating, skiing, and fishing.
  • CalAtlantic build quality at a finite scale. Roughly 139 homesites total across The Landings and Cove, plus the limited Strand luxury inventory. The community is essentially built-out, so resale inventory turns rather than competing with new-construction next door.
  • Direct Johns Lake exposure, not Lake Apopka. Johns Lake's ski-lake character and clearer water differentiate it from Lake Apopka's restoration-recovery profile; this matters for buyers prioritizing watersports.

↑ Back to Top | View Available Homes →

Waterside Location & Connections

Waterside is situated on the south shore of Johns Lake in west Winter Garden, with all three sub-sections taking access from Marsh Road just west of Avalon Road (CR-545). Hartwood Marsh Road runs along the southern approach to the community. The SR-429 (Daniel Webster Western Beltway) is a few minutes east, providing the primary route to Walt Disney World via the south and to I-4 via the north, and Florida's Turnpike connects to the broader region from the SR-429 interchange.

The community is bordered by Johns Lake to the north, with neighboring residential development to the south and east — including the Twinwaters and Sanctuary at Twinwaters communities along Marsh Road; Twinwaters straddles Marsh Road with its north section on Johns Lake and its south section overlooking Lake Avalon. Individual non-subdivision homes occupy parcels along the surrounding roads.

🏘️ Adjacent Neighborhoods & Areas
  • Johns Lake — the 2,439-acre lake directly bordering Waterside to the north
  • Sanctuary at Twinwaters — neighboring community along Marsh Road
  • Twinwaters — neighboring lakefront community split between Johns Lake and Lake Avalon
  • Individual non-subdivision homes — scattered parcels along Marsh Road, Hartwood Marsh Road, and surrounding lake roads
  • Stoneybrook West — gated golf community to the north across Johns Lake
🚗 Detailed Commute Times
  • Downtown Winter Garden / Plant Street: ~15 minutes (~6 miles via Marsh Road and Avalon Road)
  • Downtown Orlando: ~30–35 minutes (~22 miles via SR-429 and I-4)
  • UCF Campus: ~45 minutes (~32 miles)
  • Walt Disney World: ~20 minutes (~12 miles via SR-429 south)
  • Universal Orlando: ~25 minutes (~17 miles)
  • SeaWorld Orlando: ~25 minutes (~16 miles)
  • Lake Nona Medical City: ~40 minutes (~28 miles)
  • Cocoa Beach: ~75–80 minutes (~70 miles east via SR-528)
✈️ Airport Access
  • Orlando International Airport (MCO): ~35–40 minutes (~26 miles via SR-429 and SR-417)
  • Orlando Sanford International Airport (SFB): ~50 minutes (~38 miles)

↑ Back to Top | View Available Homes →

Waterside Amenities & Lifestyle

Waterside is built around its Johns Lake setting and a centralized resort-style amenity package shared by all three sub-sections. The community is designed for buyers who want lake access without the maintenance and access negotiation that comes with a single-family private dock, and who prefer a finite gated community over a master-planned new-construction environment.

Daily life centers on the amenity center off Marsh Road, the community dock on Johns Lake, and the internal pond-and-trail network that gives interior lots their water views.

🏊 Neighborhood Amenities

Amenities found within Waterside:

  • Gated entry with separate gates per sub-section (The Landings, The Strand, The Cove)
  • Community clubhouse
  • Fitness center
  • Resort-style swimming pool
  • Community pavilion
  • Playground / tot lot
  • Walking trails
  • Picnic areas
  • Community dock on Johns Lake (shared by all residents)
  • Three internal community ponds with pond-view homesites (The Landings)
  • Direct lakefront homesites on Johns Lake (select lots)
🛍️ Shopping & Services

Daily-needs shopping is just east of Waterside at Stoneybrook West Village, anchored by a Publix grocery store — about a mile away and Waterside's closest full-service shopping plaza. Larger-format retail is at Winter Garden Village at Fowler Groves, an open-air center with 80+ stores including Target, Best Buy, Lowe's, and a wide range of national retailers.

For comprehensive shopping information: View our Winter Garden Shopping Guide →

🍽️ Restaurants

Casual dining options are clustered at Stoneybrook West Village and Winter Garden Village at Fowler Groves, with chef-driven and farm-to-table options concentrated in Downtown Winter Garden along Plant Street — about 15 minutes east. The Crooked Can Brewery and Plant Street Market food hall are downtown anchors.

For comprehensive restaurant information: View our Winter Garden Restaurants Guide →

🎭 Arts & Culture

Winter Garden's cultural anchor is the restored 1935 Garden Theatre on Plant Street, hosting live theater, music, and film. The Winter Garden Heritage Museum and Central Florida Railroad Museum cover the area's citrus and rail history.

For comprehensive arts & culture information: View our Winter Garden Arts & Culture Guide →

🏃 Health & Wellness

AdventHealth Winter Garden is the closest full-service hospital, located off Fowler Grove Boulevard — about 10–12 minutes east of Waterside. Orlando Health Health Central Hospital in neighboring Ocoee is the secondary full-service option.

For comprehensive health & wellness information: View our Winter Garden Hospitals Guide →

🌳 Parks & Recreation

Johns Lake itself is Waterside's primary recreation asset, supporting waterskiing, wakeboarding, fishing, kayaking, and recreational boating. The Johns Lake Conservation Area offers a public boat ramp and fishing pier on the lake's southwestern side. The West Orange Trail passes through downtown Winter Garden to the east, providing 22 miles of paved trail through West Orange County.

For comprehensive parks & recreation information: View our Winter Garden Parks & Recreation Guide →

⚽ Sports & Athletics

On-water sports dominate the Waterside lifestyle thanks to Johns Lake. Land-based athletics center on the West Orange High School Warriors Friday-night football tradition, and the West Orange Country Club offers private golf, tennis, and pickleball about 15 minutes east.

For comprehensive sports & athletics information: View our Winter Garden Sports & Athletics Guide →

🎉 Fun Things to Do

The Saturday Winter Garden Farmers Market and Fridays on the Plaza outdoor concert series in Downtown Winter Garden are the area's signature recurring events. Theme park access via SR-429 puts Disney, Universal, and SeaWorld within 20–25 minutes.

For comprehensive events & activities information: View our Winter Garden Events & Things To Do Guide →

🎓 Schools

Waterside is likely zoned for the following Orange County Public Schools (OCPS) based on its location in the western 34787 corridor — verify current zoning directly with OCPS before relying on this for purchase decisions:

  • Elementary: Whispering Oak Elementary (likely — verify with OCPS)
  • Middle: SunRidge Middle School (likely — verify with OCPS)
  • High: West Orange High School (likely — verify with OCPS)

Note: School attendance zones in high-growth corridors like 34787 are reviewed and can shift. Always confirm current assignment with the Orange County Public Schools attendance lookup tool before making a purchase decision.

For comprehensive school information: View our Winter Garden Schools Guide →

↑ Back to Top | View Available Homes →

How Waterside Compares

Waterside's natural comparison set is the cluster of gated lakefront and lake-adjacent communities along Marsh Road and the broader Johns Lake corridor. The most direct comparisons are Twinwaters and Sanctuary at Twinwaters — both are neighboring, both built in a similar window, both gated. The differences come down to lake exposure, builder, and scale.

Feature Waterside Twinwaters Sanctuary at Twinwaters
Primary Lake Exposure Johns Lake (south shore) Johns Lake (north section) & Lake Avalon (south section) Lake Avalon
Builder CalAtlantic / Standard Pacific (now Lennar) Meritage Homes M/I Homes
Year Built ~2015 – 2022 Mid-2010s onward Late 2010s onward (newest of the three)
Gated Yes (per sub-section) Yes Yes
Shared Community Dock Yes — Johns Lake Pool & park; lake access varies by section Amenity center; Lake Avalon access
Sub-Section Structure Three tiers (Landings, Strand, Cove) Two sections (split by Marsh Road) Single section
Luxury Tier The Strand — homes to 8,600+ sq ft Lakefront premium homes Newer construction, smaller scale

💡 Value Proposition: Waterside is the option for buyers who want a Johns Lake community with a shared dock — meaning interior and pond-view homesites still get full lake-recreation access, not just lakefront owners. Twinwaters offers the same area but split across two lakes; Sanctuary at Twinwaters is newer but Lake Avalon-focused. If the priority is Johns Lake access at a price point below The Strand's $1M+ tier, Waterside's Landings sub-section is the most direct path to that combination.

↑ Back to Top | View Available Homes →

Waterside HOA & CDD Information

Waterside operates under a homeowners association (HOA) that maintains the gated entries, common landscaping, amenity center (clubhouse, fitness center, pool, pavilion), community dock on Johns Lake, walking trails, and internal ponds across all three sub-sections. Each sub-section shares the same governing association and amenity access, with section-specific entry gates.

Based on public records review at the time of this page's preparation, Waterside does not appear to carry a Community Development District (CDD) assessment — unlike many Horizon West communities south of the SR-429. This should be verified with Orange County records as part of any purchase due diligence. The HOA covers the standard package of gated-community services described above.

💰 HOA Fees & Management Contact

HOA fees and management company information often change. Please contact us and we will be happy to provide you with the current HOA fee, payment schedule, and direct contact information for the HOA management company. We can also check for you to see if there are any current or upcoming special assessments.

📋 What HOA Fees Cover
  • Gated entry maintenance and access systems (per sub-section)
  • Common-area landscaping and irrigation
  • Clubhouse and fitness center operation
  • Resort-style pool and pavilion maintenance
  • Community dock on Johns Lake — upkeep and access management
  • Walking trails and picnic areas
  • Internal community ponds and stormwater systems
  • Street lighting and signage
  • Community insurance and administrative reserves
📜 What's Permitted vs. Restricted

As with most CalAtlantic-built gated communities, Waterside operates under recorded covenants, conditions & restrictions (CCRs) that govern architectural changes, exterior modifications, landscaping standards, fencing, paint colors, and short-term rentals. Specific provisions vary by sub-section. Contact us to request a copy of the current CCR package before submitting an offer.

↑ Back to Top | View Available Homes →

Frequently Asked Questions

What is the HOA fee for Waterside?
Please contact us for the current HOA fee, payment schedule, and HOA management company contact information. Waterside's HOA covers gated-entry maintenance, the shared amenity center (clubhouse, fitness center, pool, pavilion), the community dock on Johns Lake, walking trails, and common-area landscaping across all three sub-sections.
Is there a CDD fee in Waterside?
Public records review at the time of this page's preparation does not indicate a Community Development District (CDD) assessment on Waterside parcels. This differs from many Horizon West communities south of SR-429, which do carry CDDs. CDD status should be verified with Orange County records as part of any purchase due diligence.
What schools serve Waterside?
Based on Waterside's location in the western 34787 corridor near Stoneybrook West and Twinwaters, the community is likely zoned for Whispering Oak Elementary, SunRidge Middle School, and West Orange High School. School attendance zones in high-growth corridors can shift — always verify current assignments with the Orange County Public Schools (OCPS) attendance lookup tool before making a purchase decision.
What are the three sub-sections of Waterside?
Waterside is organized into three distinct sub-sections, all sharing the same amenity center and community dock: The Landings (the largest section, with over 130 homesites including 34 Johns Lake lakefront lots and 41 pond-view lots, homes typically 2,696–5,591 square feet), The Strand (the luxury tier, with homes from approximately 2,937 to over 8,600 square feet — original CalAtlantic pricing started above $1 million), and The Cove (the smaller third section). Each sub-section has its own gated entry off Marsh Road.
Do all Waterside homes have lake access?
Yes — every Waterside homeowner has access to the community dock on Johns Lake regardless of whether their individual homesite is lakefront. This is a key distinction from many lakefront communities where dock access is limited to lakefront owners. Interior and pond-view homes still get full Johns Lake recreation access including boating, waterskiing, fishing, and kayaking.
How large is Johns Lake?
Johns Lake is approximately 2,439 acres (community marketing figure) to 2,580 acres (USF Water Atlas) — either way, roughly four square miles of surface area. The lake spans the Orange and Lake County line and supports waterskiing, wakeboarding, fishing, kayaking, and recreational boating. A public boat ramp is located on the lake's western side at Johns Lake Conservation Area.
Who built Waterside?
Waterside was built by CalAtlantic Homes (formerly Standard Pacific Homes, now part of Lennar) between approximately 2015 and 2022. CalAtlantic was responsible for all three sub-sections — The Landings, The Strand, and The Cove — which is unusual for a community of this scale and contributes to the consistent construction standards across the community.
Is Waterside gated?
Yes. Waterside is a fully gated community with separate entry gates for each of the three sub-sections (The Landings, The Strand, and The Cove), all accessed from Marsh Road just west of Avalon Road (CR-545).
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