Tall Pines Real Estate

Tall Pines Real Estate

Welcome to Tall Pines, a picturesque subdivision nestled in the heart of Florida, where the sun shines bright and the landscape is a vibrant tapestry of natural beauty. This charming community is perfectly situated for those seeking a serene lifestyle without sacrificing the conveniences of modern living.

Tall Pines boasts an array of stunning homes, each designed with meticulous attention to detail and a touch of Southern charm. Whether you’re searching for a cozy single-family home or a spacious residence with room for the whole family, you’ll find a variety of architectural styles that cater to diverse tastes and preferences. The lush greenery and towering pines that give this subdivision its name create a tranquil atmosphere, ideal for relaxation and outdoor activities.

Residents of Tall Pines enjoy a strong sense of community, with friendly neighbors and a welcoming environment that fosters connections. The subdivision is conveniently located near top-rated schools, shopping centers, and recreational facilities, making it an excellent choice for families and professionals alike. Spend your weekends exploring nearby parks, indulging in local dining hotspots, or soaking up the sun at one of Florida’s beautiful beaches, all just a short drive away.

With its perfect blend of nature, community spirit, and accessibility, Tall Pines is not just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this enchanting subdivision and experience the best that Florida has to offer!

Newest Listings in Tall Pines

$1,500,000
6 Beds ⋅ 4 Baths ⋅ Tall Pines SubDv.
Nestled beneath a canopy of mature trees in the desirable Tall Pines neighborhood, this expansive lakefront residence offers a rare combination of space, character and location. Situated on an oversized one-third-acre homesite with tranquil water views, the property is surrounded by lush tropical landscaping and enjoys a central Naples location within the highly rated Osceola Elementary, Pine Ridge Middle and Barron Collier High School zones. The home features seven bedrooms, three and one-half baths, multiple gathering spaces and a versatile upstairs bonus room, providing exceptional flexibility for guests, hobbies or home offices. Rich Brazilian hardwood floors add warmth and timeless appeal throughout much of the residence. From the moment you arrive, the home exudes a sense of charm and individuality that is increasingly difficult to find in today's market. Expansive lake views framed by mature trees create a picturesque backdrop, while the pool and outdoor living areas offer a peaceful setting for entertaining and everyday enjoyment. A long-lasting metal roof and three air conditioning systems provide a strong foundation for future enhancements. For buyers seeking something beyond the ordinary, this property presents a unique opportunity to own a home with personality, scale and enduring appeal. The setting, square footage and location combine to create exceptional long-term value in one of Naples convenient neighborhoods.

5731 Cypress Hollow Way, Naples
$1,950,000
3 Beds ⋅ 4 Baths ⋅ Tall Pines SubDv.
Experience Lakeside Luxury Living at Its Finest — Welcome to this stunning custom lakeside estate at 5700 Waxmyrtle Way in the desirable Tall Pines community of North Naples, Florida. This meticulously upgraded 1995-built home sits on a rare 0.34-acre waterfront lot and offers 3 bedrooms plus a den, 3.5 baths of sophisticated living space. Completely transformed into a private resort, this move-in-ready Naples home boasts a brand-new pool and hot tub, an expansive screened lanai with panoramic views, and a charming detached guest cottage perfect for visitors, a poolside cabana, home office, or art studio. Wake up to tranquil lake vistas, lush landscaping, fruit trees, and an herb garden right in your backyard — the ultimate Florida lifestyle. Step inside to soaring ceilings, abundant natural light, and beautiful new flooring throughout. The show-stopping chef’s kitchen features dual islands, quartzite countertops, Sub-Zero refrigeration, a commercial-grade gas range with dual ovens, a dedicated drink cooler, ice maker, and ample storage — ideal for entertaining family and friends. Relax in the private second-floor primary suite with a versatile loft (perfect for a home office or den), spa-like bath with separate tub and shower, and generous walk-in closet. Additional highlights include four sets of French doors opening to the backyard oasis, two wood-burning fireplaces, zoned HVAC, tankless water heaters, and an extended 2-car garage with epoxy flooring. Unmatched Resiliency & Peace of Mind — This home is built like a fortress with a newer metal roof, impact-resistant windows, doors & skylights, a whole-house generator with buried propane tank, and a whole-house water filtration system. Low HOA fees make it even more appealing for full-time residents or seasonal snowbirds. Located in Tall Pines, a peaceful, non-gated North Naples neighborhood with low assessments and easy access to everything: world-class beaches, fine dining, shopping at Mercato, and top-rated schools — all just minutes away. Whether you're seeking a luxurious primary residence, a vacation retreat, or an incredible investment property with strong rental potential, this lakeside Naples pool home delivers unparalleled luxury, resilience, and lifestyle. Don’t miss this rare opportunity — homes like this on oversized waterfront lots don’t last long in North Naples. Schedule your private showing today and imagine your new life in paradise at 5700 Waxmyrtle Way! ***Please note there is a detached guest studio which has it's own full bathroom and is separate, but steps from the main house.*** Perfect for guests, pool house, office, art studio, etc. (3 + Den/2.1 in main house + 1/1 in detached guest studio)

5700 Waxmyrtle Way, Naples
$1,099,000
3 Beds ⋅ 2 Baths ⋅ Tall Pines SubDv.
Welcome to 6161 Waxmyrtle Way—a beautifully refreshed pool home in one of Naples’ most sought-after neighborhoods. Freshly painted inside and out, this residence offers impact-resistant windows and doors, combining style with storm-ready peace of mind. The home features a spacious, light-filled layout centered around a private courtyard-style pool, providing the perfect backdrop for entertaining or relaxing in total privacy. High ceilings, oversized windows, and skylights invite natural light into every corner of the living space. This open floor plan includes generous guest rooms, a versatile den, and a large laundry room. The primary suite is its own retreat, complete with custom walk-in closets, dual vanities, a walk-in shower, and a freestanding soaking tub. An oversized garage offers extra space for storage or hobbies. Enjoy a fenced backyard ideal for pets, a newer roof and A/C system, and a low HOA of just $72/month. Perfectly situated just minutes from top-rated schools, Naples’ world-class beaches, fine dining, and shopping, this home is ideal for families, seasonal residents, or investors seeking long- or short-term rental potential. Homes in this quiet, centrally located community rarely hit the market—don’t miss your opportunity to own a move-in-ready home in the heart of Naples. No history of hurricane damage.

6161 Waxmyrtle Way, Naples
$249,000
2 Beds ⋅ 2 Baths ⋅ Tall Pines SubDv.
Major upgrades include a new AC system (2025) and a roof replaced in 2018. Step into this beautifully renovated townhome where everything feels fresh, bright, and ready for its next owner. The home features brand-new flooring throughout, giving every room a clean, modern feel. The kitchen has been completely updated with new cabinets and sleek countertops, making smart use of the space while still offering plenty of functionality. Both bathrooms have been fully refreshed with contemporary finishes that add comfort and style to everyday living. This home blends thoughtful updates with stylish finishes from top to bottom, making it a great opportunity for buyers seeking a move-in-ready property without the work.

3150 S Pines Drive Unit 84, Largo
$199,000
2 Beds ⋅ 2 Baths ⋅ Tall Pines SubDv.
PRICE IMPROVEMENT *NO HOA • NO Deed Restrictions • NO Short-Term Rental Restrictions! Welcome to your next home—or investment opportunity! This charming 2-bedroom, 1.5-bathroom townhome offers unbeatable flexibility and value with zero HOA fees and no limitations on leasing or short-term rentals like Airbnb. Whether you're a first-time homebuyer, savvy investor, or looking to downsize, this is the kind of rare find that checks all the boxes. Step inside to discover a bright and open layout featuring a spacious living and dining area, a convenient half bath on the main floor, and a kitchen perfect for cooking and entertaining. Slide open the doors to your private fenced patio with a peaceful garden, ideal for morning coffee, evening relaxation, or letting the dog roam freely. Upstairs, you’ll find two generously sized bedrooms—each with ample closet space, including a walk-in closet in the primary—and a full bath with private access from the primary bedroom. Tucked away on a quiet street, this home offers the perfect blend of privacy and accessibility—just minutes from beaches, restaurants, shopping, and an easy commute to downtown Tampa or St. Pete. No restrictions, no worries, just opportunity. Schedule your private showing today before it’s gone!

2811 S Pines Drive Unit 15, Largo
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