Trailside Homes for Sale

Trailside Homes for Sale

Welcome to Trailside, a charming subdivision nestled in the heart of Estero, Florida, where tranquility meets modern living. This vibrant community, located in Lee County, offers a perfect blend of nature and convenience, making it an ideal choice for families, retirees, and everyone in between.

Trailside is renowned for its picturesque landscapes, featuring lush greenery and serene walking trails that wind through the neighborhood, inviting residents to enjoy the great outdoors. Imagine taking leisurely strolls or bike rides along these scenic paths, all while basking in the warm Florida sun. The community is designed to foster a sense of camaraderie among neighbors, with friendly gatherings and events that bring everyone together.

When it comes to homes for sale in Trailside, you’ll find a diverse range of options to suit your lifestyle and preferences. From modern single-family homes to charming townhouses, each property is thoughtfully designed with open floor plans, spacious living areas, and contemporary finishes. Many homes boast private backyards, perfect for entertaining or simply enjoying a quiet evening under the stars.

Living in Trailside means having access to top-rated schools, shopping centers, and recreational facilities, ensuring that all your needs are met just a stone’s throw away. With its prime location in Estero, residents can easily explore nearby attractions, including beautiful beaches, golf courses, and vibrant dining options.

Discover the charm of Trailside and find your dream home today—where comfort, community, and Florida's stunning lifestyle await you!

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

Start Your Search

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.