Longleaf Homes with Tennis Court(s) Amenities

Welcome to Longleaf, a vibrant and welcoming subdivision nestled in the heart of Estero, Florida, within the scenic Lee County. This charming community is perfect for those seeking a balance of tranquility and active living, making it an ideal place to call home.

Longleaf boasts a variety of beautiful homes that cater to diverse lifestyles, with many properties featuring stunning tennis court amenities. For tennis enthusiasts and recreational players alike, having a private court right in your backyard transforms your home into a personal oasis. Imagine stepping out your door for a quick match with friends or family, or simply enjoying a leisurely afternoon practice as the sun sets over the lush Florida landscape.

The community is designed with an emphasis on outdoor living, offering residents access to walking trails, parks, and social areas that foster a strong sense of neighborhood camaraderie. With its prime location, Longleaf is just a short drive away from Estero’s finest shopping, dining, and entertainment options, including the nearby Coconut Point Mall and the beautiful beaches of the Gulf Coast.

Whether you're looking for a family-friendly environment, a vibrant social scene, or simply a place to unwind, Longleaf provides the perfect backdrop for a fulfilling lifestyle. Embrace the Florida sunshine and the joy of tennis in a community that truly feels like home. Discover your dream home in Longleaf today, where comfort meets active living!

Newest Longleaf Homes with Tennis Court(s) Amenities

$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) is being installed which will include 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 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/Great Room. There is also a Rinnai GAS Water heater and GAS POOL HEATER. Electric hurricane shutters are on the lanai. electric shutters over the from Door. The home also has hurricane sliding doors off the lanai!!!! 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, 9 Har Tru tennis. 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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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.