Trailside Homes for Sale

Trailside Homes for Sale

Welcome to Trailside, a hidden gem nestled in the heart of Estero, Florida! This vibrant neighborhood offers a perfect blend of serene living and modern conveniences, making it an ideal choice for families, retirees, and anyone seeking a tranquil lifestyle in sunny Southwest Florida.

Trailside is known for its picturesque landscapes, featuring lush greenery, winding trails, and sparkling lakes that invite outdoor enthusiasts to explore. Residents enjoy easy access to nature parks, walking paths, and bike trails, creating an active community that embraces the beauty of Florida's outdoors. The neighborhood is conveniently located near top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

The homes for sale in Trailside reflect the charm of the community, with a variety of architectural styles to suit different tastes and preferences. From spacious single-family homes to cozy townhouses, there’s something for everyone. Many properties boast modern amenities, open floor plans, and private backyards, perfect for entertaining or enjoying quiet evenings under the stars.

Living in Trailside means embracing a lifestyle of comfort and convenience, with access to nearby attractions such as the beautiful beaches of the Gulf Coast, the vibrant nightlife of downtown Estero, and world-class shopping at the Coconut Point Mall. Whether you’re looking for a family-friendly environment or a peaceful retreat, Trailside offers the perfect setting to call home. Explore the available homes for sale today and discover why so many are choosing to make Trailside their forever home!

Newest Trailside Homes for Sale

$539,999
3 Beds 4 Baths 2026022141 MLS ACTIVE Status
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.