Brookside Naples Real Estate - 12 Homes, 3 Lands For Sale

This nearly 2 acre parcel is an Unmatched Opportunity with zoning for 12 Multi-Family homesites! Unveil the potential with prime waterfront land on a Gulf access canal, nestled in a thriving community that’s on the rise in the unique area of Brookside! Just a stone’s throw from the charming Olde Naples, this property is perfect for investors or developers looking to create something exceptional. The groundwork for an exciting development project is already in motion—comprehensive studies have been conducted, including soundings, engineering, lot planning, elevation assessments, traffic analysis, and HOA consulting. This is your chance to be part of Naples' next great waterfront venture! Opportunities like this are few and far between—don’t miss your chance to invest in a bright future with unmatched potential! Seize this chance to secure one of the last remaining sites like this!

Introducing 1063 Shadowlawn Dr. A rare, nearly 2- acre parcel offering unlimited potential in one of Naples most sought after locations. With RMF-6 zoning permitting up to 11 multi-family residences or 1-9 luxury, single family homes, this property represents a unique opportunity for developers and investors to bring a high-end vision to life! Situated on a quiet street with creek/river access to Naples Bay, the setting combines natural tranquility with unmatched convenience-just minutes from downtown Naples' world-class dining, shopping and Gulf beaches. Architectural plans are included, providing a head start on designing a bespoke residential community that aligns with the demands of Naples' luxury market. In a market where premium development sites are increasingly scarce, 1063 Shadowlawn Drive stands out as a truly exceptional investment. Whether envisioned as an exclusive enclave of estate homes or a multi-family luxury project, this property delivers the rare combination of location, zoning flexibility and waterfront access.

There are homes designed to impress, and then there are homes designed to endure. This is unmistakably the latter. From the moment you arrive, the presence is calm, intentional, and confident. A mature Sylvester Palm anchors the entry, setting the tone for a residence that feels both rooted and forward-looking. This is modern coastal living for someone who values beauty and foresight. Built by New Era Construction and designed by Harrell & Co. Architects, this home was engineered with uncommon rigor; 55 pilings installed prior to foundation, more structural engineering than required, and materials selected not just for style, but for longevity. This is a home built to withstand the worst, so everyday life feels effortlessly secure. Inside, natural light pours through custom ES- impact resistant windows and doors, illuminating soaring ceilings that rise from 12 to over 20 feet in the main living spaces. The aesthetic is warm modernism: a thoughtful blend of tile and Legno Bastone wide-plank birch wood flooring, solid wood stair treads, and sleek glass handrails that create continuity across all three levels. Every door is solid-core and custom, reinforcing the quiet, insulated luxury you feel as you move through the home. The main living floor is anchored by quartz countertops throughout, a chef’s kitchen that balances performance and polish, and details that true design enthusiasts notice. Solid wood cabinetry and a hidden walk-in pantry keeps the kitchen visually serene while Linear diffuser vents offer a clean, architectural ceiling line. A dramatic spiral staircase leads you upward, complemented by a glass-enclosed elevator servicing all three floors ... both sculptural and practical. Marble-clad bathrooms elevate daily rituals into spa-like moments, while every space feels purposeful and refined. Step outside and the lifestyle truly unfolds. The backyard is a private coastal retreat featuring a custom Pebble Crete swimming pool with sun shelf, a raised six-person spa, PVC composite decking with Resin Eco pilings and a 13,000 lb boat lift, thoughtfully built above the seawall. Not to mention, expansive water views and unforgettable sunsets. Practical luxury continues with a standing seam aluminum roof, a concrete seashell driveway, irrigated Zoysia lawn, custom landscaping, and an oversized garage accommodating up to six vehicles. Truly a rare find for boating and car enthusiasts alike. Located just minutes from downtown Naples, 5th Avenue, white-sand beaches, and world-class golf, this is a home for someone who wants proximity without compromise, luxury without fragility, and a residence that feels as intelligent as it is beautiful. 1798 Holiday Lane isn’t just a new construction home. It’s a statement of foresight, resilience, and refined Naples living—designed for a life well lived, and built for everything that comes next.

BRAND NEW Waterfront Masterpiece, PRICED TO SELL TODAY! Experience the pinnacle of coastal luxury living in this never-lived-in waterfront estate. Perfectly positioned along a serene canal with direct Gulf access, this HOME showcases unmatched craftsmanship, exceptional design, and meticulous attention to detail throughout every space. Step inside to soaring ceilings, expansive open living areas, and walls of glass that frame breathtaking water views. The custom chef’s kitchen, refined finishes, and elegant indoor-outdoor flow make this home an entertainer’s dream. Outdoors, enjoy your private paradise with a 13,000 lb. boat lift, expansive dock, and seamless access to Naples’ world-class waterways… just a few minutes into Naples Bay and all that area has to offer. Whether cruising by boat into the sunset, or to dinner with friends, or even relaxing poolside, this residence celebrates the BEST of waterfront living. Car enthusiasts, you will be, for sure, captivated by the 6-car garage, designed with precision for collectors or hobbyists who appreciate both form and function. For car and dining enthusiasts alike, only a short walk to 5th Avenue's world-class dining AND not to forget some of the amazing car shows and other events. Every element of this HOME has been curated to surpass expectations, a TRUE statement of modern luxury, artistry, and enduring quality.

Welcome to 1794 Holiday Lane, a brand-new construction home in the rapidly evolving Brookside neighborhood—a neighborhood transforming into one of the city's most dynamic pockets. Designed for water lovers, the property sits in a true boating community with easy access to the Gulf, Naples Bay, and the Gordon River—ideal for kayaking, paddle boarding, or exploring Naples’ scenic waterways. A 10,000 lb boat lift and floating dock make getting on the water effortless, while backwater and offshore fishing are right at your fingertips. Inside, enjoy an open, bright layout with real hardwood flooring throughout, total home automation, and thoughtful upgrades that enhance everyday comfort. The home is equipped with Starlink high-speed internet, a whole-house generator, a 500-gallon propane tank, an on-demand tankless water heater, and an EV-ready garage with room for two car lifts—perfect for car enthusiasts or additional storage. This elevated residence offers peace of mind and secure living. Outdoors, the home shines with inviting spaces designed for both relaxation and entertaining. Enjoy evenings around the built-in firepit, craft meals in the wood-burning pizza oven, or unwind beneath the authentic chickee hut, complete with electric and nearby water access. The backyard provides the perfect vantage point for taking in radiant, glowing sunsets or spending peaceful days, curled up with a book, in the shade. Located in an area undergoing thoughtful redevelopment just minutes from Downtown 5th Avenue and Naples’ renowned beaches, this home offers unmatched convenience to dining, shopping, and Southwest Florida’s most coveted coastal experiences. 1794 Holiday Lane is more than a home—it's a lifestyle. Experience modern living, waterfront freedom, and the best of Naples in a community poised for continued growth and enjoyment.

This exquisitely renovated 3-bedroom, 3-bathroom canal-front residence is a masterclass in luxury design, thoughtful engineering, and waterfront convenience. Improved with no expense spared, the home offers refined finishes, exceptional amenities, and true ownership flexibility—all just minutes from downtown Naples. Every detail has been carefully curated to the highest standard. Inside, the chef’s kitchen is equipped with a premium appliance suite featuring a Sub-Zero refrigerator, Wolf oven and speed oven, Miele dishwasher, Miele warming drawer, and a built-in Miele coffee maker. Custom cabinetry, upscale finishes, and a seamless layout elevate both daily living and entertaining. Throughout the home, tile flooring, upgraded trim and doors, and custom cabinetry create a cohesive and sophisticated aesthetic. The primary suite offers a spa-inspired bath with elegant stonework and refined detailing. The outdoor living spaces rival those of a private resort. The outdoor kitchen features a Fire Magic Echelon grill with drawers and pullouts, a pizza oven, and striking quartzite countertops—ideal for elevated entertaining. The pool and spa are surrounded by elegant travertine tile, enhancing both beauty and comfort, and creates an inviting setting for relaxation and hosting. Waterfront functionality is exceptional. The private dock and boat lift are complemented by a dedicated jet ski dock, all positioned along a quiet canal with Gulf access. This setup offers effortless boating and watercraft convenience directly from the backyard, allowing for quick departures and seamless returns while maintaining privacy and tranquility. Additional standout features include an air-conditioned 2-car garage designed for both comfort and performance, complete with a built-in commercial-grade ice maker capable of holding up to 25 gallons of ice—ideal for fishing and boating days, as well as entertaining. Impact-resistant windows, ornamental aluminum detailing, multiple sliding glass doors, and extensive flood mitigation improvements further enhance durability and peace of mind. Adding to its appeal, there are no HOA rules or regulations which allows for short-term rentals, making it well suited for use as an Airbnb or VRBO, whether as a primary residence, seasonal retreat, or income-producing investment. Perfectly positioned near the renowned dining, shopping, and cultural destinations of downtown Naples, this move-in-ready residence presents a rare opportunity to own a meticulously designed waterfront home where luxury, convenience, and flexibility converge.

The Best Western View in NAPLES without being directly on the beach & it is PROTECTED from future development!! Don't miss out on this opportunity! With the protected mangroves behind this waterfront home, you will forever be able to enjoy this Gorgeous View towards Naples Bay! You just can't find a better spot to live and enjoy the sunsets of Naples, FL!! No HOA requirements. This property offers OVER 150 feet of Seawall and directly off of the Naples Bay and Bayfront shopping! Location Location Location!! Less than 5 minutes to anywhere in Downtown Naples you would like to be. Shopping, dining, entertainment and medical services ALL less than 5 minutes from Home! Give us a call or come check out this perfect property to build your own new home or take advantage of a location in ALL of Florida that anyone could LOVE! BONUS! The owner of this home is the son of Emile A. Gruppe, the American Painter. He would Love to pass along a time piece his father painted nearly 60 years ago of Naples Bay marina!! This is an amazing painting and valued over $30,000.00!

Income-Producing Waterfront Gem Near Downtown Naples. Seize this rare opportunity to own an income-producing, waterfront property just minutes from the heart of Naples! Nestled in the rapidly evolving Brookside community, this prime Gulf-access home has unobstructed canal views. With no HOA or rental restrictions, this is an ideal investment for short-term rentals or a luxurious personal retreat. Positioned in one of Naples’ most exciting redevelopment zones—including the Gateway Triangle, Metropolitan Naples, and the new 7-acre Brookside Marina—this property offers exceptional long-term value. The fully renovated home seamlessly blends modern elegance with coastal charm, featuring three bedrooms, three bathrooms, a chef’s kitchen with a gas Viking range, a Fisher & Paykel refrigerator, and exquisite quartzite countertops. For boating enthusiasts, the rare, grandfathered boathouse provides added protection for your vessel. At the same time, the private dock invites you to enjoy serene water views, spot wildlife, or head out for a sunset cruise. Just a short walk or bike ride away, you’ll find the world-class shopping, dining, and entertainment of 5th Avenue South, along with easy access to 3rd Street South, the iconic Naples Pier, and the city’s pristine sandy beaches. Whether you are seeking a lucrative rental investment or a stunning waterfront escape, this property delivers unmatched potential in one of Naples’ most sought-after neighborhoods. Act now—opportunities like this don’t last long!

An exceptional vacant land opportunity just minutes from downtown Naples. This recently subdivided 1.06-acre partially wooded lot is zoned RMF-6, allowing for up to six units per acre, offering the flexibility to create a single custom estate of your dreams or pursue a multi-home development. The property’s size, zoning, and location make it ideal those seeking a one-of-a-kind personal residence or investors. Located less than two miles from Old Naples, the lot is conveniently close to the high-end shopping and dining of 5th Avenue South and 3rd Street South, the white sandy beaches of the Gulf, and is highly bikeable to downtown. Enjoy the peaceful setting of mature trees while remaining near everyday conveniences, including the upcoming renovation of Oakes Farms Market. A truly special canvas for your vision.

Seize a truly rare opportunity to own one of the largest parcels in all of Brookside. Tucked away at the end of a quiet, secluded cul-de-sac, this oversized waterfront lot offers exceptional privacy and flexibility — whether you envision designing and building a custom canal-front estate or prefer enjoying the existing pool home as your personal retreat. With its generous dimensions and prime positioning, this property stands out as one of the most desirable offerings in the neighborhood. The current residence is being offered turnkey, presenting immediate income potential as a short-term rental or an effortless seasonal escape. The home’s layout is both comfortable and functional, thoughtfully centered around outdoor living and entertaining. Featuring impact glass windows for added storm protection, energy efficiency, and peace of mind, the property is well-suited for both full-time and seasonal living. The private pool area embraces the relaxed Naples lifestyle, creating an inviting setting for gathering with family and friends or simply unwinding in the sunshine. For boating enthusiasts, this property truly shines. A cut-in double boat slip and covered boat house provide added convenience and protection, while the tranquil canal setting allows for quick, direct access to Naples Bay in approximately 10 minutes. From there, you’re just moments from the Gulf of Mexico, waterfront dining, and endless days exploring the water. Ideally located just 2 miles from the world-class dining and shopping of 5th Avenue South and only 3 miles to Naples’ beautiful white-sand beaches, this property offers the perfect blend of privacy and accessibility. In addition, Brookside and the surrounding East Naples area continue to see exciting growth and investment, including the ongoing transformation of Metropolitan Naples, the planned Oakes development, Naples Marina projects, the JW Marriott expansion, and the highly anticipated Pavarotti Opera Center — further enhancing long-term value and lifestyle appeal. Oversized waterfront lots with direct boating access this close to downtown are becoming increasingly rare. Don’t miss your opportunity to secure one of Brookside’s premier canal-front properties.

Navigable waterfront boater’s paradise just steps from Tin City & Downtown Naples! 1796 Holiday Lane is an exceptional opportunity to build your dream home on a sizable .20-acre navigable waterfront homesite in the highly desirable neighborhood of Brookside. Nestled towards the end of a quiet cul-de-sac street, this premium lot offers unmatched serenity, privacy, and stunning Western rear exposure—perfect for taking in Naples’ world-class sunsets from the comfort of your own backyard. This property offers over 70 feet of navigable frontage with existing seawall and dock in place overlooking the wide canal that feeds into Rock Creek, the Gordon River, and Naples Bay, with just one bridge standing between you and the open waters of the Gulf of Mexico. Enjoy the ultimate waterfront lifestyle, complete with easy access to some of Southwest Florida’s finest fishing, boating, and waterfront dining. Located just minutes from Downtown Naples, this prime location puts you within reach of both 5th Avenue South and Historic Third Street South's premier shopping and dining, world-class beaches, and the best that the Paradise Coast of Florida has to offer its residents. Whether you're looking to build your luxury custom home or a more modest boater’s retreat, this lot offers an incredible opportunity to create your own slice of Naples paradise and at a great value too. Brookside lacks the minimum 30-day rental policy restriction in place for properties located within City limits and there are no mandatory homeowners association fees! Don’t miss out on this rare opportunity—schedule a viewing today and start building your dream waterfront lifestyle.

Welcome to 1138 Christopher Court, a rare Gulf-access homesite offering an effortless and scenic boat ride from your covered boat lift to Naples Bay—where golden sunsets, waterfront dining, and open-water adventure become part of everyday life. Tucked away on a quiet cul-de-sac, this exceptional 0.28-acre (12,259 SF) waterfront lot presents a unique opportunity to build your custom dream home in one of Naples’ most charming and rapidly evolving neighborhoods—just 1.5 miles from iconic Fifth Avenue South. The property features 100 feet of waterfront complete with a covered boat dock, creating the perfect foundation for a residence designed around seamless indoor-outdoor living. There is ample space for a pool, lush gardens, and expansive outdoor entertaining areas, all while maintaining a sense of privacy and tranquility. A land survey and a full set of architectural plans for a custom home are already complete and available, allowing you to fast-track your vision. Christopher Court is undergoing an exciting transformation, with multiple luxury new-construction homes in progress that are quickly elevating the street into a refined enclave of modern coastal residences. The surrounding neighborhood is equally dynamic, highlighted by the redevelopment of Metropolitan Naples, bringing ground-level boutique shops and restaurants, Class-A office space, and structured parking. Nearby Oakes Farm is anticipated to return as a two-story grocer within a larger five-acre development along Davis Boulevard—effectively extending the energy and walkability of Fifth Avenue. This expansion will introduce additional dining, hotels, a new marina, and lifestyle amenities, all within walking distance to this LOT. The neighborhood’s voluntary HOA offers desirable flexibility while preserving the well-kept, welcoming character residents appreciate. With its unmatched location, direct boating access, and outstanding build potential, this is more than a vacant lot—it’s the foundation for an exceptional Naples lifestyle. Upscale dining, boutique shopping, vibrant galleries, and the sugar-sand beaches Naples is known for are all just minutes away.