Trailside Real Estate

Trailside Real Estate

Welcome to Trailside, a hidden gem nestled in the heart of Estero, Florida. This charming subdivision is more than just a collection of homes; it’s a vibrant community where neighbors become friends and every day feels like a vacation. Located in Lee County, Trailside boasts a prime location that offers the perfect blend of tranquility and accessibility.

As you stroll through the beautifully landscaped streets of Trailside, you’ll be captivated by the picturesque surroundings and the warm, welcoming atmosphere. The community features a variety of thoughtfully designed homes, each exuding a unique charm that reflects the relaxed Florida lifestyle. With spacious layouts and modern amenities, these residences are perfect for families, retirees, and everyone in between.

Trailside is not just about beautiful homes; it’s about the lifestyle that comes with them. Residents enjoy access to a wealth of amenities, including serene walking trails, sparkling community pools, and vibrant parks where children can play and families can gather. The community is also conveniently located near some of Estero’s best shopping, dining, and entertainment options, ensuring that everything you need is just a stone's throw away.

Outdoor enthusiasts will appreciate the proximity to stunning beaches, golf courses, and nature preserves, making it easy to embrace the sunny Florida lifestyle. Whether you’re seeking a peaceful retreat or an active lifestyle, Trailside offers the perfect setting to create lasting memories. Discover your next home in this enchanting community and experience the charm of Trailside in Estero, Florida!

Newest Listings in Trailside

3 Beds ⋅ 2 Baths ⋅ Trailside SubDv.

Under Construction. This thoughtfully designed home in the Trailside community features 3 bedrooms, 2 baths, and a spacious 2-car garage. The open floorplan offers abundant natural light and a seamless flow through the main living areas, which showcase beautiful wood-look luxury vinyl plank flooring. The spacious primary suite boasts a private sitting area perfect for a nursery, office or flex space. The kitchen is equipped with 42" white cabinets, a large island with upgraded quartz countertops, and stainless steel appliances—perfect for everyday living and entertaining. Plush upgraded carpet adds comfort in the bedrooms, plus upgraded 8' interior doors are included throughout. The interior design selections feature the AW Collection Harmony, where rustic meets elegant and warm wood tones reflect a relaxed style. Bring the outdoors in with a covered lanai just off the living area. Enjoy community amenities including a pool, clubhouse, and playground. Conveniently located near top-rated schools and the charming shops and restaurants of downtown Mount Dora. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

30130 Emerald Forest Drive, Mount Dora

3 Beds ⋅ 2 Baths ⋅ Trailside SubDv.

Under Construction. Discover effortless Florida living in this beautifully designed Douglas II home, featuring the AW Collection Milan, located in the desirable Trailside community of Mount Dora. This single-story residence offers 3 bedrooms, 2 baths, and a 2-car garage, thoughtfully crafted for comfort and modern style. The open-concept floor plan is filled with natural light and features 42" neutral-toned cabinets, stainless steel appliances, and a large island with upgraded quartz countertops, making the kitchen ideal for both everyday living and entertaining. Wood-look luxury vinyl plank flooring enhances the main living areas, while the bedrooms feature upgraded carpet for added comfort. Residents of Trailside enjoy access to community amenities including a resort-style pool, clubhouse, and playground. Ideally situated near top-rated schools and just minutes from the charming shops and restaurants of historic downtown Mount Dora, this home offers the perfect blend of convenience, style, and community living. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

30173 Emerald Forest Drive, Mount Dora

Trailside SubDv.

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

3 Beds ⋅ 2 Baths ⋅ Trailside SubDv.

Under Construction. Welcome to the Brickell II, a beautifully designed home featuring the AW Collection Serene, with muted earth tones, natural textures, and clean-lines. This 3-bedroom, 2-bath floorplan offers an inviting open-concept layout filled with natural light and thoughtful details throughout. The gourmet kitchen features 42" white cabinets, stainless steel appliances, a large island with upgraded quartz countertops, and plenty of storage—perfect for entertaining or family gatherings. The main living areas are enhanced with wood-look luxury vinyl plank flooring, while the bedrooms feature upgraded carpet for added comfort. Enjoy community amenities including a resort-style pool, clubhouse, and playground, all within the charming Trailside neighborhood. Conveniently located near top-rated schools and just minutes from the historic streets of downtown Mount Dora, with its boutique shopping, dining, and local charm, this home offers the perfect blend of style, comfort, and location. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

30135 Emerald Forest Drive, Mount Dora

3 Beds ⋅ 4 Baths ⋅ Trailside SubDv.

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

Start Your Search