Longleaf Homes with Tennis Community Type

Welcome to Longleaf, a picturesque subdivision nestled in the heart of Estero, Florida, within Lee County. This charming community embodies the perfect blend of tranquility and active living, making it an ideal destination for families, retirees, and anyone seeking a vibrant lifestyle in sunny Florida.

Longleaf is renowned for its beautiful homes, each thoughtfully designed to enhance the serene surroundings. The architecture reflects a blend of modern elegance and classic charm, with spacious layouts that cater to a variety of lifestyles. Residents enjoy the luxury of well-manicured lawns, lush landscaping, and an inviting atmosphere that fosters a true sense of community.

One of the standout features of Longleaf is its commitment to an active lifestyle, particularly for tennis enthusiasts. The community boasts a premier tennis facility, complete with well-maintained courts and a vibrant tennis community. Whether you’re a seasoned player or just starting, you’ll find ample opportunities to engage in friendly matches, join clinics, or participate in social events that bring neighbors together.

Beyond tennis, Longleaf offers a host of amenities and recreational activities. Residents can enjoy walking trails, parks, and nearby shopping and dining options, ensuring that everything you need is just a stone's throw away. The community’s prime location also provides easy access to Estero’s stunning beaches and outdoor adventures, making it a haven for nature lovers.

Experience the charm of Longleaf, where beautiful homes and an active tennis community create the perfect backdrop for your Florida lifestyle. Come discover your dream home in this delightful subdivision today!

Newest Longleaf Homes with Tennis Community Type

$875,000

4 Beds ⋅ 3.5 Baths ⋅ 226011976 MLS

Just reduced to $349./per square foot. Owner will include GOLD COMMONS CLUB membership for newly built Beach Club!! Brand new HVAC system (2 units) was installed July 2026 which includes a 12-year warranty. Exterior painting was completed mid-May…thanks to the Longleaf HOA. Whether scaling down from a larger custom home or moving-up from a condo you will love the living space provided by the Kingfisher floor plan- and this one particularly on the cul-de-sac gives you extra privacy with a extra long drive-way and front yard plus LAKE & ISLAND from the lanai. Rare to find 2 FULL BATHS on the 2nd floor which accommodates your guests. A large 1st floor Master Suite offers walk-in closets, a large bathroom space with separate vanities and separate walk-in shower and corner bathtub. Kitchen offers GE STAINLESS STEEL Profile Refrigerator, Dishwasher, Microwave and GAS range. Pantry. and there is an extra storage closet in Laundry room. Washer and Dryer are Samsung. Also on the first floor is the office/den has wood flooring and a walk-in closet. 4 BATHROOMS TOTAL as one is a powder room by the Foyer and Great Room. There is also a Rinnai GAS Water heater and GAS POOL HEATER. POOL DEPTH is 6 feet. Electric hurricane shutters are on the lanai. electric shutters over the from Door. The home also has hurricane rated sliding doors off the lanai for the kitchen, great room and master bedroom. Garage has a split AC. A new tile ROOF as of 2020. Homeowners only used the home for a few weeks each year / it was never rented. Shadow Wood Country Club offers 54 holes of championship golf, 2 clubhouses, Har Tru tennis courts. 2 Bocce courts. Shadow Wood is in the process of building a Brand new Lifestyle Centering opening Fall-2026 with 6 new Indoor PICKLEBALL Courts, Brand new RESORT POOL with poolside dining and bar, a dedicated KIDS POOL and pool with lap lanes. This 26 Million dollar world class facility comes with NO assessment to Members.

21780 Longleaf Trail Drive, Estero

$749,000

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.)

22140 Long Leaf Trail DR, Estero

$849,000

4 Beds ⋅ 2.5 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 DR, Estero

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