Trailside Real Estate

Welcome to Trailside, a hidden gem nestled in the heart of Estero, Florida, within the beautiful Lee County. This charming subdivision offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and anyone seeking a vibrant community atmosphere.

As you stroll through the tree-lined streets of Trailside, you'll be captivated by the picturesque surroundings and meticulously maintained homes. The subdivision features a variety of architectural styles, ensuring that there's something to suit every taste. With spacious lots and lush landscaping, residents enjoy a sense of privacy while remaining connected to their neighbors.

One of the standout features of Trailside is its proximity to some of the best amenities that Estero has to offer. Just a short drive away, you'll find a plethora of shopping, dining, and entertainment options, including the popular Coconut Point Mall and the upscale Miromar Outlets. For outdoor enthusiasts, the stunning beaches of Bonita Springs and the scenic Estero River are just minutes away, providing endless opportunities for relaxation and adventure.

Families will appreciate the highly-rated schools in the area, ensuring that children receive a quality education. Additionally, the community is conveniently located near major highways, making commutes to nearby cities like Fort Myers and Naples a breeze.

Whether you're looking to settle down or invest in a vacation home, Trailside offers a welcoming environment where neighbors become friends and memories are made. Discover the charm of Trailside today and experience the best of Estero living!

Newest Listings in Trailside

$275,000

2026029617 MLS

Exceptional opportunity to build your dream home on over 2/3 of an acre in the heart of Estero! Located within the Estero city limits, west of US-41, this oversized homesite is nestled in the charming and historic Estero community. Enjoy the perfect balance of privacy and convenience with easy access to Coconut Point Mall, Miromar Outlets, FGCU, Hertz Arena, Gulf Coast Town Center, award-winning golf courses, beautiful Gulf beaches, and Southwest Florida International Airport. With plenty of room for a custom home, outdoor living space, a pool, or additional garage storage, the possibilities are endless. Large homesites in this prime location are becoming increasingly rare. Don't miss your chance to create the home and lifestyle you've been dreaming of in one of Southwest Florida's most sought-after communities.

20190 Trailside DR, Estero

$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.