Longleaf Real Estate

Longleaf Real Estate

Welcome to Longleaf, a vibrant and inviting community nestled in the heart of Estero, Florida, in Lee County. This exceptional development is designed for those who appreciate the perfect blend of modern living and natural beauty. Longleaf offers a unique lifestyle that caters to families, retirees, and everyone in between, making it an ideal place to call home.

As you explore Longleaf, you'll be captivated by its picturesque surroundings. The community is enveloped in lush landscapes, featuring scenic ponds and mature trees that create a serene atmosphere. Residents enjoy access to a variety of amenities, including a sparkling community pool, well-maintained walking trails, and recreational areas perfect for family gatherings or leisurely strolls with your furry friends.

Longleaf is strategically located, providing easy access to major highways, shopping centers, and dining options. Just a short drive away, you'll find the stunning beaches of the Gulf Coast, offering endless opportunities for sunbathing, water sports, and relaxation. Additionally, the community is in close proximity to top-rated schools and healthcare facilities, ensuring that everything you need is just around the corner.

The homes in Longleaf boast modern designs and high-quality finishes, offering a range of options to suit diverse tastes and lifestyles. Whether you're searching for a cozy single-family home or a spacious townhome, Longleaf has something for everyone.

Come and discover the charm and warmth of Longleaf in Estero, Florida. Experience a community that feels like home, where every day is an opportunity to embrace the beauty of life in paradise.

Newest Listings in Longleaf

4 Beds ⋅ 4 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

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 Drive, Estero

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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Kelly O'Connell

Kelly O’Connell, Realtor® – Serving Cape Coral and SWFL With almost a decade of real estate experience and more than 25 years in Sales and Marketing leadership within the Property Management industry, Kelly O’Connell brings a wealth of knowledge and professionalism to every client interaction. Based in Cape Coral, Kelly has built her reputation representing top builders and specializing in new construction homes, helping clients navigate the exciting process of building or buying in one of Florida’s most desirable markets. Her expertise extends beyond new construction to luxury homes, relocations, first-time home buyers, and investment properties, ensuring every client—no matter their goals—receives the same level of attentive, personalized service. Kelly’s approach is founded on building lasting relationships, transparent communication, and always putting her clients first. Her extensive background in property management and marketing gives her a unique perspective on market trends and makes her a trusted advisor throughout every stage of the real estate journey. Whether you’re relocating to Southwest Florida, investing in a vacation property, or building your dream home, Kelly is dedicated to helping you achieve your real estate goals with confidence and care.

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Jennifer Oravec‑Cottrell

Jennifer Oravec‑Cottrell is a trusted Realtor focused on providing personalized, client‑centered service. With a strong sales background and a commitment to clear communication, Jennifer helps buyers and sellers achieve their real estate goals with confidence. She is known for her professionalism, responsiveness, and dedication to making every transaction as smooth and stress‑free as possible. We can take care of everything you need, from start to close. Your Trusted Southwest Florida Real Estate Experts As local real estate experts, Jennifer & Kelly bring an unmatched depth of knowledge about buying and selling homes in Southwest Florida. Real estate is never one-size-fits-all, and having a trusted advisor with up-to-date market insight makes all the difference. Their expertise ensures you’re informed, confident, and fully supported every step of the way. Find Your Next Home You deserve more than just a home—you deserve the right home. Jennifer & Kelly know Southwest Florida inside and out and will work closely with you to find the perfect property at the right price. From neighborhood amenities and lifestyle considerations to the must-have features on your wish list, they focus on what matters most to you. Sell Your Home with Confidence When it’s time to move, you need professionals who can handle every detail seamlessly. From strategic marketing and professional showings to contract negotiations, financing coordination, inspections, and closing, Jennifer & Kelly manage the entire process from start to finish—ensuring a smooth, stress-free experience and maximum value for your home. Strategic Home Selling Consultation Buyers don’t always see a home the way sellers do—and that’s where expert guidance matters. Jennifer & Kelly provide tailored recommendations to position your home for its ideal audience, helping it stand out, attract strong offers, and achieve top dollar. Whether you’re buying, selling, relocating, or investing, Jennifer & Kelly are committed to delivering personalized service, clear communication, and exceptional results. Let’s get you moving—with confidence and care.

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