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Hammock Trails Homes for Sale

2772 Big Timber Drive, Kissimmee image
2772 Big Timber Drive, Kissimmee $280,000

Best-priced 4-bedroom home in the area! Don't miss this incredible opportunity to own a spacious 4-bedroom, 2-bath single-family home in Kissimmee. This well-maintained h...

  • 4 Beds
  • 2 Baths
  • Hammock Trails SubDv.
  • 34758 Zip Code
2808 Polson Drive, Kissimmee image
2808 Polson Drive, Kissimmee $364,990

Seller is offering $5,000 toward the buyer's closing costs with a full-price offer! Welcome to this beautifully maintained 3-bedroom, 2-bathroom home featuring 1,483 squ...

  • 3 Beds
  • 2 Baths
  • Hammock Trails SubDv.
  • 34758 Zip Code
4808 Rockvale Dr, Kissimmee image
4808 Rockvale Dr, Kissimmee $370,000

From the moment you walk through the front door, you're welcomed by a huge formal living and dining area that's perfect for family gatherings, holidays, or hosting friend...

  • 4 Beds
  • 2 Baths
  • Hammock Trails Ph 2b Amd Rep SubDv.
  • 34758 Zip Code
4621 Yellow Bay Drive, Kissimmee image
4621 Yellow Bay Drive, Kissimmee $399,900 ▼

SELLER MOTIVATED!!! Beautifully maintained home featuring an open and bright floor plan with spacious living areas and generously sized bedrooms with walk-in closets. Rec...

  • 3 Beds
  • 3 Baths
  • Hammock Trails SubDv.
  • 34758 Zip Code
4607 Kalispell Road, Kissimmee image
4607 Kalispell Road, Kissimmee $327,000 ▼

Updated Price! Brand New Roof put on... 7/8/2026!!! Opportunity to own a nice 3 bedroom, 2 bath home in a wonderful neighborhood. Centrally located in south Kissimmee on ...

  • 3 Beds
  • 2 Baths
  • Hammock Trails SubDv.
  • 34758 Zip Code
2756 Big Timber Drive, Kissimmee image
2756 Big Timber Drive, Kissimmee $315,000 ▼

This 3 bedroom, 2 bath ranch style home offers 1,493 sq ft of living space, built in 2012 with durable block construction and tile flooring throughout. This property back...

  • 3 Beds
  • 2 Baths
  • Hammock Trails SubDv.
  • 34758 Zip Code
2804 Polson Drive, Kissimmee image
2804 Polson Drive, Kissimmee $479,900 ▼

New on the market! Beautiful single-family home in Kissimmee, Florida, offered at $479,900. This 3-bedroom, 2.5-bath residence features a loft and was originally a former...

  • 3 Beds
  • 3 Baths
  • Hammock Trails SubDv.
  • 34758 Zip Code
4647 Caverns Drive, Kissimmee image
4647 Caverns Drive, Kissimmee $325,000 ▼

Move-in ready single-story home in Hammock Trails with New Roof! Sellers are offering $6,000 toward buyers’ closing costs, and additional credits may apply when using a p...

  • 3 Beds
  • 2 Baths
  • Hammock Trails SubDv.
  • 34758 Zip Code
Home › Kissimmee › Hammock Trails
📋 What's on This Page
  • About Hammock Trails Neighborhood
  • Location & Connections
  • Neighborhood Amenities & Lifestyle
  • How Hammock Trails Compares
  • HOA Information
  • Frequently Asked Questions
  • Available Homes

Hammock Trails Homes for Sale

Kissimmee, FL 34758 | Established Single-Family Community in the Pleasant Hill Corridor

Hammock Trails is an established single-family home community of over 300 residences in the Pleasant Hill area of southern Kissimmee. Built between 2006 and 2017 by AV Homes (now Meritage Homes), the neighborhood features spacious 3- to 6-bedroom homes with community amenities including a pool, playground, and 24-hour gated entry — all positioned along Ham Brown Road with convenient access to Pleasant Hill Road, S Poinciana Boulevard, and the nearby Valencia College Poinciana Campus. View Available Homes

✔ Information verified current as of April 2026

About Hammock Trails Neighborhood

Hammock Trails is one of southern Kissimmee's most established family neighborhoods, developed by AV Homes (now part of Meritage Homes) between 2006 and 2017. Located off Ham Brown Road just south of US Highway 17-92, the community comprises over 300 single-family homes spread across multiple phases, making it one of the larger residential subdivisions in the Pleasant Hill corridor of Osceola County.

Homes in Hammock Trails range from approximately 1,332 to 3,902 square feet, offering configurations from 3 bedrooms and 2 bathrooms up to 6 bedrooms and 3.5 bathrooms. The community was built in phases — Phase 1, Phase 2A, and Phase 2B — with earlier homes completed during the 2006–2010 period and later phases finished by 2017. Architectural styles feature traditional Florida design with concrete block construction, covered entries, and attached two-car garages. Many homes include desirable features such as formal living and dining rooms, kitchen islands with granite countertops, and master suites with walk-in closets and dual-vanity bathrooms.

One of Hammock Trails' distinguishing characteristics is the presence of multiple retention ponds throughout the community, several of which create attractive waterfront homesites with pond and conservation views. The community's mature landscaping — now over a decade established in the earlier phases — gives the neighborhood a settled, tree-canopied character that newer communities in the area cannot yet match.

Hammock Trails is also notable for its proximity to Valencia College's Poinciana Campus, which sits adjacent to the community's southern boundary. This makes the neighborhood particularly attractive to college students, faculty, and families who value immediate access to higher education resources without a lengthy commute.

📊 Quick Facts
Property Style(s):Single-Family Homes
Home Sizes:1,332–3,902 sq ft
Bedrooms:3–6
Bathrooms:2–3.5
Year Built:2006–2017
Builder:AV Homes (now Meritage Homes)
HOA Fee:Contact us for current fee
CDD Fee:Contact us for current status
Total Homes:Approximately 300+
Gated:Yes — 24-hour guard gate
Garage:2-Car Attached
🏠 What Makes Hammock Trails Special
  • 24-Hour Guard Gate: Hammock Trails offers gated entry with 24-hour security, providing an extra layer of privacy and safety for residents — a feature not commonly found in this price range.
  • Waterfront Homesites: Multiple retention ponds throughout the community create desirable water-view lots with sunset views and natural wildlife habitat, adding value and scenic appeal.
  • Mature Landscaping: With the earliest homes over 18 years established, Hammock Trails features mature tree canopy and landscaping that gives the neighborhood a settled, park-like character.
  • Adjacent to Valencia College: The Poinciana Campus of Valencia College borders the community, offering immediate access to higher education, workforce training, and community programs.
  • Spacious Floor Plans: Homes range up to nearly 4,000 square feet with up to 6 bedrooms, accommodating large families, multigenerational living, and home office needs.

↑ Back to Top | View Available Homes →

Hammock Trails Location & Connections

Hammock Trails is located in the Pleasant Hill area of southern Kissimmee, accessed via Ham Brown Road off S Poinciana Boulevard. The community sits at the southern end of the Ham Brown Road residential corridor, positioned between established neighborhoods to the north and the growing Poinciana area to the south.

The location provides multiple commuting options. Pleasant Hill Road (CR-531) connects eastward to US 17-92 and the Florida Turnpike, while S Poinciana Boulevard runs south to Cypress Parkway and the broader Poinciana commercial area. The Poinciana SunRail Station is a short drive north, offering commuter rail access to downtown Orlando and other employment centers.

🏘️ Adjacent Neighborhoods & Areas
  • Emerald Lake — lakeside community to the north along Ham Brown Road
  • Doral Woods — residential neighborhood to the northeast
  • Doral Pointe — upscale subdivision to the east
  • Countryside Manor — semi-rural community to the west
  • Retention ponds and conservation areas border the community, with Valencia College Poinciana Campus adjacent to the south along Rockvale Drive and S Poinciana Boulevard
🚗 Detailed Commute Times
  • Downtown Kissimmee: 25 minutes (15 miles)
  • Downtown Orlando: 45 minutes (35 miles)
  • UCF Campus: 60 minutes (45 miles)
  • Walt Disney World: 30 minutes (22 miles)
  • Universal Orlando: 45 minutes (30 miles)
  • SeaWorld Orlando: 40 minutes (26 miles)
  • Lake Nona Medical City: 40 minutes (25 miles)
  • Cocoa Beach: 80 minutes (70 miles)
  • Poinciana (Cypress Parkway): 8 minutes (4 miles)
✈️ Airport Access
  • Kissimmee Gateway Airport (ISM): 20 minutes (6 miles)
  • Orlando International Airport (MCO): 35 minutes (18 miles)
  • Orlando Sanford International Airport (SFB): 65 minutes (55 miles)

↑ Back to Top | View Available Homes →

Hammock Trails Amenities & Lifestyle

Hammock Trails offers a family-oriented lifestyle centered around its community amenities and the natural beauty of its pond-lined streetscapes. The gated entry and 24-hour guard provide a sense of security that appeals to families with children, and the community pool and playground serve as gathering points for neighbors throughout the year.

The surrounding Pleasant Hill corridor provides daily essentials within a short drive, while Kissimmee's broader amenity network — from Lake Tohopekaliga waterfront recreation to The Loop shopping center — is accessible within 15 to 25 minutes.

🏊 Neighborhood Amenities

Amenities within Hammock Trails include:

  • Community swimming pool
  • Children's playground
  • 24-hour guard-gated entry
  • Recreation facilities
  • Multiple scenic retention ponds with waterfront walking areas
  • HOA-maintained common areas, landscaping, and community roads
  • Trash removal included in HOA
🛍️ Shopping & Services

Daily shopping is available along Pleasant Hill Road and S Poinciana Boulevard, including Publix at Pleasant Hills Commons and various retail plazas. The Loop on John Young Parkway provides expanded retail and entertainment options approximately 20 minutes north.

For comprehensive shopping information: View our Kissimmee Shopping Guide →

🍽️ Restaurants

Restaurant options along the Pleasant Hill and Poinciana corridors include family dining, fast-casual chains, and independent restaurants serving Latin American, Caribbean, and American cuisine. The downtown Kissimmee dining scene along Broadway offers 30+ independent restaurants approximately 25 minutes north.

For comprehensive restaurant information: View our Kissimmee Restaurants Guide →

🎭 Arts & Culture

Cultural attractions in the region include Osceola Arts for live theater and concerts, the Osceola County Welcome Center & History Museum, and downtown Kissimmee's public art and mural scene.

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

🏃 Health & Wellness

The closest hospital is HCA Florida Poinciana Hospital, approximately 10 minutes south on Cypress Parkway. AdventHealth Kissimmee and HCA Florida Osceola Hospital provide additional full-service care approximately 25 minutes north.

For comprehensive health & wellness information: View our Kissimmee Health & Wellness Guide →

🌳 Parks & Recreation

Outdoor recreation includes Kissimmee Lakefront Park and Big Toho Marina for boating and fishing, Shingle Creek Regional Park for hiking and kayaking, and family-friendly parks with playgrounds and splash pads throughout Osceola County.

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

⚽ Sports & Athletics

Sports and recreation options include championship golf courses throughout the Kissimmee area, the Bob Makinson Aquatic Center for swimming programs, and youth sports leagues for soccer, baseball, and basketball.

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

🎉 Fun Things to Do

Area attractions include Gatorland, Old Town Kissimmee, Island H2O Water Park, and Wild Florida airboat adventures. Major theme parks — Walt Disney World, Universal Orlando, and SeaWorld — are 30 to 45 minutes away.

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

🎓 Schools

Hammock Trails is served by:

  • Elementary: Sunrise Elementary School
  • Middle: Horizon Middle School
  • High: Poinciana High School

Additionally, Valencia College Poinciana Campus is directly adjacent to the community, offering associate degrees, bachelor's degrees, and workforce training programs.

Note: School assignments are subject to change. Always verify current zoning with the Osceola County School District before making purchasing decisions based on school boundaries.

For comprehensive school information: View our Kissimmee Schools Guide →

↑ Back to Top | View Available Homes →

How Hammock Trails Compares

Hammock Trails occupies a distinct position in the southern Kissimmee market. As an established community with mature landscaping and a 24-hour guard gate, it offers amenities and curb appeal that newer neighborhoods are still developing — while its resale pricing remains competitive with surrounding subdivisions.

Feature Hammock Trails Doral Woods Emerald Lake
Property Type Single-Family Single-Family Single-Family
Year Built 2006–2017 2004–2010 2005–2012
Total Homes 300+ ~150 ~100
Gated Entry Yes — 24-hr Guard No No
Community Pool Yes No No
Largest Floor Plan ~3,900 sq ft ~2,800 sq ft ~2,500 sq ft
Waterfront Lots Yes — Pond Views Limited Yes — Lake Views
Adjacent College Valencia College No No

💡 Value Proposition: Hammock Trails is the only community in this corridor offering the combination of 24-hour guard-gated security, a community pool, waterfront homesites, and adjacency to Valencia College — all at resale pricing that remains competitive with non-gated alternatives in the area.

↑ Back to Top | View Available Homes →

Hammock Trails HOA & CDD Information

Hammock Trails has a mandatory homeowners association that maintains the community's common areas, pool, playground, guard gate, landscaping, and community roads. The HOA also covers trash removal, property insurance for common areas, and recreation facility maintenance. HOA fees in Hammock Trails vary by phase and location within the community.

The 24-hour guard gate is one of the community's most valued amenities, providing controlled access and an added sense of security for families. Pets are permitted in Hammock Trails, though the HOA enforces limits on the number and type of pets allowed — prospective buyers should confirm current pet policies through the management company.

💰 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
  • 24-hour guard-gated entry and security
  • Community swimming pool maintenance
  • Playground and recreation facility upkeep
  • Common area landscaping and grounds maintenance
  • Community road maintenance
  • Trash removal
  • Property insurance for common areas
  • Reserve fund contributions

↑ Back to Top | View Available Homes →

Frequently Asked Questions

What is the HOA fee for Hammock Trails?
Please contact us for the current HOA fee, payment schedule, and HOA management company contact information. HOA fees in Hammock Trails vary by phase and cover the guard gate, community pool, playground, grounds maintenance, community roads, trash removal, and reserve funds.
Is there a CDD fee in Hammock Trails?
Please contact us to confirm the current CDD status for Hammock Trails. CDD fees and amounts can vary between phases of the community. We can provide you with the exact assessment amount for any specific property you are considering. For more information on what CDDs are, see our guide to CDD fees.
What schools serve Hammock Trails?
Hammock Trails is zoned for Osceola County Public Schools: Sunrise Elementary School, Horizon Middle School, and Poinciana High School. Valencia College Poinciana Campus is adjacent to the community for higher education. Always verify current school zoning with the Osceola County School District before making purchasing decisions.
Is Hammock Trails a gated community?
Yes, Hammock Trails is a gated community with 24-hour guard-staffed entry. This provides controlled access and an enhanced sense of security for all residents — a feature that distinguishes Hammock Trails from many nearby neighborhoods in the same price range.
Are pets allowed in Hammock Trails?
Yes, pets are allowed in Hammock Trails. The HOA permits dogs and cats but enforces limits on the number of pets per household. Specific pet policies and any breed or size restrictions should be confirmed with the HOA management company before purchasing.
What amenities does Hammock Trails offer?
Hammock Trails community amenities include a swimming pool, children's playground, 24-hour guard-gated entry, recreation facilities, and HOA-maintained common areas with scenic retention ponds. Trash removal is also included in the HOA fees.
How close is Valencia College to Hammock Trails?
Valencia College Poinciana Campus is directly adjacent to the southern boundary of Hammock Trails, making it one of the closest residential communities to the campus. The college offers associate degrees, bachelor's degrees, and workforce training programs.

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