Three Communities, Two Sides of Winter Garden
Winter Garden is one of the most sought-after cities in Central Florida, and for good reason. It combines small-town charm with modern convenience, lakefront living with theme park access, and nature trails with upscale dining. But not all Winter Garden neighborhoods are the same.
This guide covers three of the most compelling luxury communities in the area: Waterside on Johns Lake, Hawksmoor by Mattamy Homes, and Hickory Hammock at Johns Lake. Each offers a different lifestyle, price point, and location within Winter Garden. Understanding how they compare. and where they sit geographically. is the key to finding the right fit.
Geographic Positioning: North vs. South
Winter Garden splits into two distinct zones, and knowing the difference matters.
North Winter Garden. Historic Downtown Side
Community: Hickory Hammock at Johns Lake
This is the side of Winter Garden closest to Historic Downtown, with its brick-lined Plant Street, craft breweries and tasting rooms, the Winter Garden Farmers Market, and the West Orange Trail. Hickory Hammock sits on the north shore of Johns Lake, giving residents a walkable connection to downtown's restaurants, shops, and weekend events. The vibe here is established, community-oriented, and rooted in Winter Garden's original character.
South Winter Garden. Horizon West Side
Communities: Waterside on Johns Lake and Hawksmoor
The south side of Winter Garden flows into the Horizon West growth corridor. This is where you find newer construction, direct SR-429 expressway access, proximity to Walt Disney World via Western Way, and shopping and dining at Hamlin Town Center. Waterside sits on the south shore of Johns Lake, while Hawksmoor is positioned in the heart of Horizon West. The vibe here is modern, convenient, and connected.
Waterside on Johns Lake
Waterside on Johns Lake is a gated community of 130+ homes built between 2016 and 2018 by CalAtlantic (now Lennar). It's divided into three sections. The Landings, The Strand, and The Cove. each offering different home sizes and configurations along the southern shore of Johns Lake.
This is a community built around the lake. The 34 lakefront homesites and 105 interior homesites give buyers options at different price points, but the defining feature is the water. Lakefront homeowners can install private docks, and the entire community shares access to a community viewing dock overlooking the 2,500-acre lake.
Waterside on Johns Lake. Market Snapshot
4-5 bedrooms. Gated. CalAtlantic/Lennar construction. Near SR-429 expressway. Marsh Road Public Boat Ramp approximately 4 miles. Data as of June 2026. Contact me for current listings.
- Gated with controlled entry
- 34 lakefront homesites with private dock capability on Johns Lake
- Community viewing dock for all residents
- Three sections: The Landings, The Strand, and The Cove
- 4-5 bedrooms, floor plans from 2,697 to 6,145 sqft
- Community pool, pavilion, playground, fitness center, trails
- SR-429 expressway access for quick commuting
- Marsh Road Public Boat Ramp approximately 4 miles away
Hawksmoor by Mattamy Homes
Hawksmoor is a master-planned community built by Mattamy Homes in the heart of Horizon West. Unlike Waterside and Hickory Hammock, Hawksmoor is not gated. It was intentionally designed as an open, walkable streetscape with clean front-facing streets, rear-loading garages accessed through private alleyways, and a pedestrian-first layout.
The architecture sets Hawksmoor apart from everything else in Winter Garden. Homes feature a Frank Lloyd Wright-inspired blend of craftsman and mid-century modern design. not the Mediterranean or Tuscan style common in Central Florida. The result is a neighborhood that looks and feels distinctly different from its neighbors.
Hawksmoor. Market Snapshot
Single-family HOA: $115-$127/mo. Townhome HOA: $284-$286/mo. CDD assessment applies. Mattamy Homes construction, multiple phases. 3-5 bedrooms. Data as of June 2026. Contact me for current listings.
Not gated. open, walkable streetscape design. Frank Lloyd Wright-inspired craftsman and mid-century modern architecture. Both townhomes and single-family homes available. Rear-loading garages via private alleyways for clean street fronts. Lot sizes: 0.11-0.15 acres. Resort amenities: infinity-edge pool, splash pad, modern clubhouse, summer kitchen, yoga lawn, playground, fitness center, trails. Canary Island Palms throughout the community landscaping. 15 minutes from Disney's back entrance via Western Way. Near Hamlin Town Center for shopping and dining.
Hawksmoor Is Best For
Hickory Hammock at Johns Lake
Hickory Hammock is a gated community of approximately 500 homes on the north shore of Johns Lake, built between 2014 and 2018 by multiple builders including CalAtlantic, Ryland Homes, M/I Homes, and Lennar. It's the largest of the three communities and the most diverse in terms of home types and price points.
The community is anchored to Johns Lake but also borders two smaller bodies of water. Lake Burnett and Lake Claire. making water views and access a central part of the lifestyle. Lakefront lots range from 0.35 to 0.5+ acres, while interior lots run 0.15 to 0.25 acres. The luxury Emerald Pointe section features waterfront estates priced at $1 million or more.
Hickory Hammock. Market Snapshot
Multiple builders. Lakefront lots 0.35-0.5+ acres. Interior lots 0.15-0.25 acres. Townhomes also available. Near Historic Downtown Winter Garden. Marsh Road Public Boat Ramp approximately 2 miles. Data as of June 2026. Contact me for current listings.
Gated with controlled entry. ~500 homes across multiple sections and builders. Emerald Pointe luxury lakefront section. $1M+ estates. Private docks on Johns Lake for lakefront homeowners. Community boardwalk, viewing dock, and fishing pier. Resort amenities: zero-entry pool, clubhouse, fitness center, tennis courts, volleyball courts, dog park, trails. Three waterways: Johns Lake, Lake Burnett, and Lake Claire. Minutes from Historic Downtown Winter Garden. Plant Street, breweries, Farmers Market, West Orange Trail. Marsh Road Public Boat Ramp approximately 2 miles away.
Johns Lake: The Centerpiece
Johns Lake is what connects Waterside and Hickory Hammock. At approximately 2,500 acres, it's one of the largest lakes in the Winter Garden area and a recognized tournament bass fishing destination. The lake consists of two pools. East and West. connected by a navigable channel.
Anglers target largemouth bass, chain pickerel, and bluegill throughout the year. The lake is also popular for kayaking, canoeing, and paddleboarding through the Johns Lake blueway trail. Professional bass fishing guides operate regularly on the lake.
The primary public access point is the Marsh Road Public Boat Ramp at 13620 Lake Blvd, Winter Garden, FL 34787. The ramp accommodates two boats simultaneously with approximately 28 trailer parking spots. However, lakefront homeowners in both Waterside and Hickory Hammock can launch directly from their private docks.
Boat and Lake Access Comparison
| Feature | Waterside on Johns Lake | Hawksmoor | Hickory Hammock |
|---|---|---|---|
| On Johns Lake | Yes. south shore | No | Yes. north shore |
| Private Docks | Yes. lakefront lots | N/A | Yes. lakefront lots |
| Community Dock | Community viewing dock | N/A | Boardwalk, viewing dock, fishing pier |
| Nearest Boat Ramp | Marsh Road. ~4 miles | Marsh Road. ~8 miles | Marsh Road. ~2 miles |
| Lake Fishing | Bass, pickerel, bluegill | N/A | Bass, pickerel, bluegill |
| Kayak/Paddle Access | From private dock | N/A | From private dock or community pier |
Community Comparison at a Glance
| Feature | Waterside | Hawksmoor | Hickory Hammock |
|---|---|---|---|
| Gated | Yes | No | Yes |
| Builder(s) | CalAtlantic / Lennar | Mattamy Homes | CalAtlantic, Ryland, M/I, Lennar |
| Year Built | 2016-2018 | 2020+ | 2014-2018 |
| Total Homes | 130+ | Multiple phases | ~500 |
| Price Range | $510K-$1.54M | $399K-$1.27M | $400K-$1M+ (Emerald Pointe) |
| Median Price | ~$1.25M | Varies by product | ~$583K |
| Sqft Range | 2,697-6,145 | 1,599-4,645 | Varies by section |
| HOA/Month | $215-$218 | $115-$286 + CDD | $212-$742 |
| Architecture | Contemporary Florida | Mid-century / Craftsman | Traditional Florida |
| Location Zone | South (Horizon West) | South (Horizon West) | North (Historic Downtown) |
| Pool Type | Community pool | Infinity-edge pool + splash pad | Zero-entry resort pool |
| Townhomes | No | Yes | Yes |
Who Should Choose Which Community
Choose Waterside If You Want
Choose Hawksmoor If You Want
Choose Hickory Hammock If You Want
The Winter Garden Lifestyle
Beyond these three communities, Winter Garden itself is one of Central Florida's most livable cities. Historic Downtown Winter Garden features brick-lined Plant Street with independent restaurants, craft breweries, boutique shops, and the year-round Winter Garden Farmers Market. The West Orange Trail runs 22 miles through the city, connecting neighborhoods for biking, running, and walking.
Families benefit from highly rated Orange County Public Schools. Commuters have access to SR-429, the FL Turnpike, and US-192. Disney World, Universal Studios, and SeaWorld are all within a 20-30 minute drive. And Orlando International Airport is approximately 35 minutes east.
Whether you're drawn to the lake, the architecture, the downtown walkability, or the theme park access, Winter Garden delivers a quality of life that's hard to match in Central Florida.
Work With Micaela Navarra
Micaela Navarra is a licensed Orlando Realtor with M2M Realty, a boutique brokerage that goes the extra mile for every client. As a smaller, more concentrated firm, M2M Realty delivers the kind of personal attention and dedication that larger brokerages simply can't match.
With over 30 years of calling Orlando home, Micaela knows every neighborhood, every school district, and every hidden gem across Central Florida. Whether you're buying your first home, selling a luxury estate, relocating from out of state, or investing in rental property, Micaela provides hands-on guidance from the first conversation through closing day and beyond.
Languages: English, Spanish, Italian, and Portuguese
Call or text Micaela directly: 407.761.5501
Winter Garden's luxury communities combine upscale living with the charm of a walkable downtown and access to the West Orange Trail. Estate neighborhoods here offer large lots, custom homes, and a lifestyle that balances exclusivity with small town warmth.
Micaela knows Winter Garden's luxury market inside and out, from gated communities to waterfront estates. She helps buyers evaluate each neighborhood's unique offerings and guides sellers in positioning their premium properties for maximum impact.
Whether you are drawn to golf course estates, lakefront properties, or custom build opportunities, Winter Garden's luxury market offers exceptional options. Contact Micaela for private tours and access to Winter Garden's finest properties.