Trailside Real Estate

Trailside Real Estate

Welcome to Trailside, a charming subdivision nestled in the heart of Estero, Florida, within Lee County. This picturesque community offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone seeking a vibrant lifestyle in sunny Southwest Florida.

Trailside is characterized by its beautifully landscaped streets, well-maintained homes, and a friendly, welcoming atmosphere. Residents enjoy a strong sense of community, with neighbors often gathering for social events and activities that foster camaraderie. The subdivision features a variety of single-family homes, each designed with modern amenities and spacious layouts to suit diverse lifestyles.

One of the standout features of Trailside is its proximity to outdoor recreational opportunities. The area is surrounded by lush parks, scenic walking trails, and nature preserves, making it a haven for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, the natural beauty of the region is at your doorstep.

For those who appreciate shopping and dining, Trailside is conveniently located near a plethora of options. The vibrant Coconut Point Mall and the upscale Miromar Outlets are just a short drive away, offering an array of retail shops, restaurants, and entertainment venues. Plus, with the beautiful Gulf Coast beaches only a short drive away, residents can easily indulge in sun-soaked days by the water.

In Trailside, you’ll find not just a home, but a lifestyle filled with warmth, community spirit, and endless opportunities for adventure. Come experience the charm of Estero and discover why Trailside is the perfect place to call home!

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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