Longleaf Homes with Gated Community Type

Longleaf Homes with Gated Community Type

Welcome to Longleaf, an enchanting subdivision nestled in the heart of Estero, Florida, within the picturesque Lee County. This charming community offers a perfect blend of tranquility and modern living, making it an ideal haven for families, retirees, and everyone in between.

Longleaf boasts a stunning collection of homes, each designed to reflect the beauty and elegance of Florida's natural landscape. With its gated community type, residents can enjoy peace of mind and privacy, creating a secure environment for families and individuals alike. The lush, manicured surroundings and thoughtfully designed streets invite you to explore the beauty of your new neighborhood.

One of the standout features of Longleaf is its commitment to community living. Residents can take advantage of a variety of amenities, including a sparkling community pool, walking trails, and recreational areas perfect for gatherings and outdoor activities. The friendly atmosphere fosters a sense of belonging, making it easy to connect with neighbors and create lasting friendships.

Conveniently located, Longleaf offers easy access to Estero's vibrant shopping, dining, and entertainment options. Whether you're in the mood for a relaxing day at the beach or an adventurous outing at nearby parks, you'll find it all just moments away.

Discover your dream home in Longleaf, where comfort meets elegance in a serene, gated environment. Experience the perfect balance of luxury and community, and make Longleaf your new home sweet home. Don’t miss the opportunity to be part of this exceptional neighborhood!

Newest Longleaf Homes with Gated Community Type

21891 Longleaf Trail Drive, Estero
$860,000
3 Beds ⋅ 3 Baths ⋅ Longleaf SubDv.
Imagine waking up to your beautiful private lanai with lake view and preserve beyond, with the popular Kingfisher model in the Longleaf neighborhood of Shadow Wood? Freshly painted throughout, this home is ready for you to move in and enjoy Season. The kitchen boasts gorgeous quartz countertops, stainless appliances including newer GE Cafe gas range and double drawer dishwasher, tons of white cabinetry storage and a pantry. 2024 roof. Natural gas. New whole home generator. New gas pool heater. Interior recently painted throughout. Master bedroom suite new flooring. Master bath has been beautifully renovated. Enjoy all southwest Florida has to offer in this beautiful home. Member owned Shadow Wood Country Club offers 54 holes of championship golf, 2 club houses, 8 Har Tru tennis courts, bocce, outdoor fire pits, access to a private beach club, fitness center, full-service spa, pickle ball, and private restaurant. New Lifestyle Amenity Center will add 2 resort style pools with zero-depth entry, lap lanes and dedicated kids pool, poolside restaurant & bar, 6 indoor pickleball courts, new racquets pro shop and a grab & go cafe. Great location close to shopping, airport, beaches and much, much more.

21891 Longleaf Trail Drive, Estero
21750 Longleaf Trail Drive, Estero
$849,000
4 Beds ⋅ 3 Baths ⋅ Longleaf SubDv.
Nestled on a beautiful, oversized cul-de-sac lot in sought-after Estero, 21750 Longleaf Trail Dr offers a thoughtfully upgraded home that blends modern improvements with lasting comfort and style. The exterior was just painted along with the interior offering a bright refreshed aesthetic from the moment you arrive. Step inside to discover a beautifully updated interior, featuring a tastefully refreshed kitchen with new countertops, sleek sinks, a stylish backsplash, and refinished cabinetry—creating a space that is both functional and refined. New flooring was put in the primary bedroom and entry bedroom. Major systems have been meticulously upgraded for peace of mind and efficiency, including a new roof (2023), HVAC system (2025), and water heater (2025). A whole-house water filtration system with an additional under-sink filter (2025) provides clean, high-quality water throughout the home. With its extensive updates, inviting interior, and peaceful outdoor setting, this home offers an exceptional opportunity to enjoy comfortable, stylish living in a desirable Estero location.Outside, your private retreat awaits. A sparkling pool is perfect for relaxation and entertaining, enhanced by a new pool heater (2024) and filter (2025) for year-round enjoyment. The spacious cul-de-sac lot offers added privacy, tranquility, and room to enjoy Florida’s outdoor lifestyle. The garage is equipped for modern living with a Tesla charger and a new garage door opener (2025). Recent appliance updates—including the washer, dryer, refrigerator, dishwasher, microwave, and cooktop—ensure a truly move-in-ready experience. With its peaceful location, exceptional upgrades, and inviting outdoor space, 21750 Longleaf Trail Dr delivers not just a home, but a lifestyle of comfort, convenience, and serenity.

21750 Longleaf Trail Drive, Estero
22140 Long Leaf Trail Drive, Estero
$741,500
3 Beds ⋅ 2 Baths ⋅ Longleaf SubDv.
Exclusive, Shadow Woods at the Brooks, waterfront home. Enjoy spectacular sunsets as you lounge on your private, poolside lanai. Featuring an open floor plan with plenty of natural light. Perfect for entertaining. or just quiet enjoyment. Shadow Wood Country Club memberships are available and offer a spectacular clubhouse, 3 championship golf courses and a top rated tennis program. Additional membership to The Commons Club at the Brooks offers a private beach club, fitness club, social activities and swimming pool. NEW amenity of the Lifestyle Center construction and expansion are underway and will include: indoor Pickleball courts, new tennis courts, a resort-style pool with poolside seating, a firepit lounge, poolside restaurant with full kitchen and a brand-new racquets pro shop (projected completion is Fall 2026. this project will be done with no assessment to the Members. Fees for the community are $5000 per year and the individual neighborhood is $950 per quarter which includes exterior painting, trash, cable and landscaping.

22140 Long Leaf Trail Drive, Estero
21900 Longleaf Trail Drive, Estero
$849,000
4 Beds ⋅ 3 Baths ⋅ Longleaf SubDv.
This stunning home features a spacious screened lanai with south exposure, offering breathtaking lake and preserve views, complemented by a gas-heated pool—creating an ideal outdoor sanctuary for morning coffee or relaxing during the day. An 3 bedroom plus den Kingfisher model home located in the highly desirable Shadow Wood at The Brooks community, it offers the perfect balance of comfort, style, and Florida lifestyle living. The open-concept Great Room design on the first floor features soaring ceilings, abundant natural light, and spacious living and dining areas—perfect for relaxing and entertaining. The updated kitchen boasts new granite countertops, a pantry, breakfast bar, and ample storage, seamlessly flowing into the dining area and out to the outdoor oasis. The primary suite and den are conveniently located on the first floor, while upstairs offers two guest bedrooms and a versatile loft space, ideal for family or visitors. The Shadow Wood Club has been completely renovated, providing world-class amenities, and there is no current assessment for the community. Residents enjoy optional golf and country club memberships, tennis, pickleball, fitness, and access to The Commons Club with a private beach club, spa, and dining. This home truly captures the essence of luxury Florida living—a peaceful retreat surrounded by nature and community, where every day feels like a getaway.

21900 Longleaf Trail Drive, Estero
Start Your Search

How much is your home worth?

Get instant property value now!