Hickory Hammock at Johns Lake
Winter Garden's premier lakefront gated community with direct Johns Lake access and resort-style amenities.
Live the MaxLife.
$975K
Median Price
$400K – $2.3M
500
Homes
$212–$742
Monthly HOA
2004
Established
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Background
A brief history
Hickory Hammock at Johns Lake was developed as a master-planned community beginning in the early 2000s, with homes built by M/I Homes and other quality builders. The community was strategically positioned on the southeastern shores of 2,500-acre Johns Lake, one of Central Florida's most pristine natural waterways. Over the past two decades, Hickory Hammock has evolved into one of Winter Garden's most sought-after addresses, combining new construction with mature landscaping and established neighborhood character. The gated entry and HOA management by Artemis Lifestyles have ensured consistent maintenance and community standards throughout the community's growth.
The feel
What it's like to live here
Hickory Hammock at Johns Lake feels like an exclusive retreat despite its proximity to urban conveniences. Towering oak trees with Spanish moss shade the community's walking trails and residential streets, creating a natural, resort-like atmosphere. The neighborhood blends single-family homes ranging from 2,000 to 5,000+ square feet with upscale townhomes, offering diverse housing options. Waterfront living defines the experience—the community pier, private home docks, and lake views are visible from many properties, constantly reminding residents of the unique lakefront lifestyle they've chosen. The gated entry and active HOA create a sense of security and belonging, while proximity to shopping, dining, and Orlando attractions keeps it accessible rather than isolated.
The details
What to expect
Architecture & Homes
Hickory Hammock features a mix of single-family homes and townhomes built primarily in the mid-2000s through 2010s. Home styles range from Mediterranean and Florida Contemporary to traditional suburban designs. Most homes range 2,000–5,000 square feet with 3–5 bedrooms. Lot sizes vary, with waterfront properties commanding premium pricing. Many homes feature covered patios, screened lanais, and layouts designed to capture lake views. Newer constructions offer updated finishes; older homes typically have strong bones and mature landscaping. Builder-grade finishes were standard, but many owners have upgraded kitchens and bathrooms over time.
Amenities & Lifestyle
The community offers extensive amenities centered around Johns Lake and a full-service clubhouse. A zero-entry community pool, fitness center with modern equipment, and air-conditioned clubhouse serve as social hubs. Sports facilities include clay tennis courts, sand volleyball, and pickleball courts. Walking trails with mossy oak canopy connect the community, while a community pier and individual home docks provide direct lake access. A dog park and playgrounds cater to families and pet owners. The lakefront lifestyle is the main draw—boating, fishing, water sports, and sunset walks are part of daily life for many residents.
Schools
Hickory Hammock is served by the Orange County School District. Whispering Oak Elementary is just 0.5 miles away, making it highly convenient for young families. Hamlin Middle School serves the community (approximately 5.5 miles away), and West Orange High School is the district high school. All three schools are rated schools within Orange County and feed into a solid academic pipeline. The proximity of the elementary school is a major advantage for young families.
Location & Access
Hickory Hammock sits on the southeastern shore of Johns Lake in southwest Orange County, directly adjacent to Stoneybrook West Parkway and Towne Commons Boulevard. SR-429 (Winter Garden-Vineland Road) is minutes away, providing rapid access to downtown Orlando, Disney World, Universal Studios, and I-4. Winter Garden Village at Fowler's Grove shopping center is nearby for groceries and dining. Stoneybrook Golf Course is adjacent, appealing to golf enthusiasts. The location balances rural waterfront calm with suburban convenience—you're in nature but not far from urban amenities or major commute routes.
Community
Amenities
- Zero-entry community pool with deck and lounge areas
- Full-service clubhouse with social areas
- State-of-the-art fitness center
- Clay tennis courts
- Sand volleyball courts
- Pickleball courts
- Community pier and dock access
- Private home docks for lakefront properties
- Walking and jogging trails with oak canopy
- Dog park
- Children's playgrounds
- Community park areas
- Gated entry with 24-hour security
- Landscaped common areas with lake views
Know Before You Buy
HOA rules worth knowing
- Gated community with controlled access entry
- HOA management by Artemis Lifestyles
- Architectural review required for exterior modifications
- Pet restrictions and dog park usage guidelines
- Dock access and boating regulations for lakefront properties
- Violation procedures and enforcement for community standards
- Community amenity reservation policies for clubhouse and facilities
- Landscaping and yard maintenance standards
- Parking and vehicle management within community
- Annual HOA budget and reserve contributions
Market Commentary
What the market is doing
Hickory Hammock at Johns Lake commands premium pricing in Winter Garden because of its rarity: direct lake access on a 2,500-acre waterfront with gated security and resort-style amenities. Homes range $400k–$2.25M, with most well-maintained move-in-ready homes selling between $800k–$1.2M. Lakefront and dock-access properties push toward $1.5M+. The $212–$742 HOA range reflects lot size and home type, but buyers accept this because they're paying for lake access and community management that most Winter Garden neighborhoods can't match. I'm seeing steady demand from families drawn to the schools, professionals commuting via SR-429, and retirees seeking an active lifestyle on the water.
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Homes available in Hickory Hammock at Johns Lake
12 homes currently listed in Hickory Hammock at Johns Lake.
$199,000
14501 Grove Resort Ave #3534
Winter Garden, FL 34787
3 bd · 2 ba · 1,396 sqft
Grove Resort And Spa Hotel Condominium
MLS ID #S5156702, FLARE PROPERTIES LLC.
Listing provided by Stellar MLS
$550,000
16031 Pebble Bluff Loop
Winter Garden, FL 34787
4 bd · 4 ba · 2,487 sqft
Waterleigh Ph 2a
MLS ID #O6438293, MARIANI REALTY GROUP.
Listing provided by Stellar MLS
$699,000
14050 Fairway Willow Ln
Winter Garden, FL 34787
3 bd · 2 ba · 2,027 sqft
Woodbridge On Green
MLS ID #O6392994, LAKEFIELD REALTY GROUP LLC.
Listing provided by Stellar MLS
$787,000
16771 Oakboro Street St
Winter Garden, FL 34787
5 bd · 4 ba · 2,840 sqft
Waterleigh Ph 3b 3c & 3d
This property is under contract. Contact us for backup offer opportunities.
MLS ID #O6436008, DOUGLAS ELLIMAN.
Listing provided by Stellar MLS
$699,000
15139 Canopy Cover Dr
Winter Garden, FL 34787
2 bd · 2 ba · 2,000 sqft
Del Webb Oasis Phase 2
MLS ID #O6415871, INTERNATIONAL TEAM INC.
Listing provided by Stellar MLS
$398,000
15056 Windflower Aly
Winter Garden, FL 34787
3 bd · 3 ba · 1,536 sqft
Osprey Ranch Ph 1
MLS ID #O6434353, WRA BUSINESS & REAL ESTATE.
Listing provided by Stellar MLS
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of September 2, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA