Trailside Real Estate

Trailside Real Estate

Welcome to Trailside, a vibrant new community nestled in the heart of Estero, Florida, where the beauty of nature meets modern living. This exceptional development offers a harmonious blend of luxury and comfort, designed to cater to the needs of families, retirees, and everyone in between.

Trailside is strategically located in Lee County, just a stone's throw away from the stunning Gulf Coast beaches, making it an ideal spot for those who crave sun, sand, and surf. With an array of shopping, dining, and recreational options nearby, residents can enjoy the best of both worlds—tranquility and convenience.

The community features meticulously crafted homes that exemplify contemporary design, with spacious floor plans and high-quality finishes. Each residence is thoughtfully constructed to maximize natural light and provide a seamless indoor-outdoor living experience, perfect for Florida’s warm climate.

At Trailside, residents can indulge in a variety of amenities that promote an active and social lifestyle. Enjoy leisurely strolls along scenic walking trails, take a dip in the resort-style pool, or engage with neighbors at the community clubhouse. For outdoor enthusiasts, nearby parks and nature preserves offer endless opportunities for hiking, biking, and exploring the lush landscape of Southwest Florida.

With its prime location, stunning homes, and a welcoming community atmosphere, Trailside is more than just a place to live—it's a lifestyle. Discover your dream home in Estero today, and experience the perfect blend of relaxation and adventure that Trailside has to offer. Your new beginning awaits!

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 Drive, 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 Drive, Estero
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