Trailside Real Estate

Welcome to Trailside, an enchanting neighborhood nestled in the heart of Estero, Florida, within the vibrant Lee County. Known for its serene landscapes and family-friendly atmosphere, Trailside offers a perfect blend of comfort and convenience, making it an ideal place to call home.

As you stroll through the tree-lined streets of Trailside, you’ll discover charming single-family homes, many of which boast modern amenities and spacious yards, perfect for outdoor gatherings or quiet evenings under the stars. The community fosters a welcoming spirit, where neighbors quickly become friends, and children can play freely in the safe environment.

One of the standout features of Trailside is its proximity to some of the best recreational opportunities in the area. Just a short drive away, you’ll find the breathtaking Estero Bay Preserve State Park, where nature enthusiasts can explore miles of trails, spot diverse wildlife, and enjoy kayaking in the tranquil waters. For those who love shopping or dining, the nearby Coconut Point Mall offers a delightful mix of boutiques, restaurants, and entertainment options, ensuring you never have to venture far for a fun day out.

Families will appreciate the highly-rated schools in the area, making Trailside an excellent choice for raising children. With a strong sense of community, beautiful surroundings, and easy access to all that Lee County has to offer, Trailside truly embodies the essence of Florida living. Whether you’re looking for a peaceful retreat or an active lifestyle, this neighborhood has something for everyone. Come explore Trailside and discover your dream home in this idyllic setting!

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.