Longleaf Homes for Sale

Longleaf Homes for Sale

Welcome to Longleaf, a captivating community nestled in the heart of Estero, Florida, within the beautiful Lee County. This charming neighborhood offers a perfect blend of nature, modern living, and a vibrant community spirit, making it an ideal place to call home.

Longleaf is renowned for its picturesque landscapes, featuring lush greenery and serene water views that create a tranquil atmosphere. The development is thoughtfully designed to promote an active lifestyle, with an array of amenities that cater to residents of all ages. Enjoy leisurely strolls along scenic pathways, take a refreshing dip in the community pool, or gather with friends and family at the clubhouse for social events and activities.

The homes for sale in Longleaf are a true testament to quality and style. Each residence is crafted with meticulous attention to detail, showcasing open floor plans, modern finishes, and spacious interiors that seamlessly blend comfort with elegance. Whether you’re looking for a cozy single-family home or a contemporary townhouse, Longleaf offers a variety of options to suit your lifestyle needs.

Living in Estero means you’re just minutes away from some of Florida’s most beautiful beaches, shopping destinations, and culinary delights. With easy access to major highways, you can explore everything the vibrant Southwest Florida region has to offer.

Discover the charm of Longleaf today, where community, comfort, and convenience come together to create the perfect place to call home. Don’t miss your chance to be a part of this thriving neighborhood—explore the available homes for sale and find your dream home in Longleaf!

Newest Longleaf Homes for Sale

21891 Longleaf Trail Drive, Estero
$860,000
3 Beds ⋅ 3 Baths ⋅ 226030561 MLS
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 ⋅ 226003803 MLS
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 ⋅ 225082392 MLS
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 ⋅ 225078768 MLS
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
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