Trailside Real Estate

Trailside Real Estate

Welcome to Trailside, a stunning new development nestled in the heart of Estero, Florida! This vibrant community is designed for those who seek a harmonious blend of modern living and natural beauty. With its picturesque surroundings, Trailside offers residents a unique opportunity to experience the best of Southwest Florida's lifestyle.

Situated in Lee County, Estero is known for its lush landscapes, pristine waterways, and an abundance of recreational activities. Trailside captures the essence of this charming city, featuring beautifully crafted homes that are thoughtfully designed to meet the needs of today’s homeowners. Each residence showcases contemporary architecture, spacious floor plans, and high-quality finishes, ensuring comfort and style.

At Trailside, community is at the forefront. Residents can enjoy a wealth of amenities, including resort-style pools, state-of-the-art fitness centers, and serene walking trails that wind through the lush natural surroundings. The development is also conveniently located near a variety of shopping, dining, and entertainment options, making it easy to enjoy everything Estero has to offer.

For outdoor enthusiasts, Trailside is just a stone’s throw away from some of Florida's most beautiful beaches and parks. Whether you’re kayaking in the Estero River, playing a round of golf at nearby courses, or simply soaking up the sun, adventure awaits right outside your door.

Discover the perfect blend of tranquility and modern living at Trailside, where your dream home awaits in the enchanting city of Estero. Come and be part of this flourishing community today!

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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