Trailside Real Estate

Trailside Real Estate

Welcome to Trailside, a hidden gem nestled in the heart of Estero, Florida. This vibrant neighborhood is a perfect blend of serene natural beauty and modern conveniences, making it an ideal place for families, retirees, and everyone in between.

Trailside boasts a rich tapestry of lush landscapes, with winding trails and picturesque parks that invite outdoor enthusiasts to explore. The community is surrounded by stunning preserves and wetlands, offering residents the chance to enjoy nature right at their doorstep. Imagine leisurely strolls along scenic pathways, birdwatching in the nearby preserves, or enjoying a picnic at one of the many parks—Trailside truly embodies the Florida lifestyle.

Convenience is key in Trailside, as residents have easy access to a plethora of shopping, dining, and entertainment options. Just a short drive away, you’ll find the bustling Coconut Point Mall, featuring a wide array of shops, restaurants, and entertainment venues. For those who enjoy the outdoors, Estero’s pristine beaches and golf courses are just minutes away, providing endless opportunities for recreation and relaxation.

Education is a priority in Trailside, with top-rated schools and educational facilities nearby, ensuring that families have access to quality education for their children. The community is also known for its friendly atmosphere, where neighbors become friends and community events foster a strong sense of belonging.

Whether you’re looking to settle down or invest in a vacation home, Trailside in Estero, FL, offers a delightful blend of tranquility and convenience. Come discover the charm of Trailside, where your dream lifestyle awaits!

Newest Listings in Trailside

$275,000
2026029617 MLS ⋅ Trailside BLDG.
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 ⋅ Trailside BLDG.
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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