Trailside Homes for Sale

Trailside Homes for Sale

Welcome to Trailside, a captivating subdivision nestled in the heart of Estero, Florida, within the vibrant Lee County. This charming community offers a harmonious blend of nature and modern living, making it an ideal destination for families, retirees, and everyone in between.

Trailside is renowned for its picturesque surroundings, featuring lush landscapes, serene walking trails, and beautiful parks that invite residents to embrace the great outdoors. With its prime location, residents can enjoy easy access to the stunning beaches of the Gulf Coast, as well as a variety of shopping, dining, and entertainment options nearby. The community is also conveniently situated near top-rated schools and essential amenities, ensuring a well-rounded lifestyle for all.

Homes for sale in Trailside showcase a diverse range of architectural styles and sizes, catering to various preferences and budgets. From charming single-family homes to modern townhouses, each property is designed with comfort and functionality in mind. Many homes feature spacious layouts, contemporary finishes, and private outdoor spaces, perfect for entertaining or simply enjoying the Florida sunshine.

In addition, Trailside fosters a strong sense of community, with friendly neighbors and engaging social events that bring residents together. Whether you’re looking to relax by the pool, take a stroll along the scenic trails, or participate in community gatherings, Trailside offers a welcoming atmosphere that truly feels like home.

Explore the exceptional homes for sale in Trailside today and discover the perfect place to create lasting memories in this enchanting Estero community!

Newest Trailside Homes for Sale

$539,999
3 Beds 4 Baths 2026022141 MLS
Wonderful Home with 5 Bedrooms Incredible Opportunity. This is not just a home it’s a rare opportunity to own a unique and versatile property in this zip code, designed for comfort, flexibility, and modern Florida living. Offering 3 bedrooms, 2 bathrooms, plus 2 private guest efficiencies with independent entrances, this property functions as a five-bedroom, four-bathroom residence, perfect for extended family, guests, or even rental income potential. Built in 2022, this almost-new home spans just under 2,000 square feet and showcases beautiful Key luxury finishes throughout. From the moment you step inside, you are welcomed by elegant flooring, detailed crown molding, and a bright, open layout that immediately feels warm and inviting. The kitchen is truly the heart of the home, featuring white shaker cabinetry, stainless steel appliances, granite countertops, and a spacious breakfast bar ideal for entertaining. A dedicated dining area flows seamlessly into the open-concept kitchen and living room, all designed in a spacious great room style that maximizes comfort and functionality. The private master suite offers a peaceful retreat with a walk-in closet and a beautifully designed ensuite bathroom complete with dual sinks and a large walk-in shower. Toward the front of the home, you’ll find two additional bedrooms, a full bathroom, and a convenient laundry room. Step outside to the oversized tiled lanai, perfect for relaxing or hosting gatherings. This space connects to a second lanai that leads to the two guest quarters. Each efficiency includes its own kitchenette, bedroom, and bathroom, offering privacy and independence for visitors or tenants. The property also features: Impact-resistant windows for added protection and energy efficiency, elegant, modern rear doors with beautiful views, a fully fenced yard, a two-car garage, a covered front porch with tile flooring — the perfect spot to enjoy your morning coffee and the beautiful Florida sunshine and the most important factor, is located in one of the most desirable and growing areas, this home offers easy access to major highways and is conveniently close to Naples Fort Myers, highways, including Southwest Florida International Airport, allowing you to get anywhere quickly and effortlessly. Another major advantage? The maintenance of this nearly new home is significantly more affordable compared to older properties, helping you avoid costly repairs and constant upkeep. This home is truly one of a kind, if you are looking to schedule a private tour, please schedule your showing today. Enjoy added financial benefits with no HOA fees and NO flood zone , helping keep your monthly costs lower.

20230 Trailside DR, Estero

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.