Brookside Homes with Boating Community Type

Welcome to Brookside, a hidden gem nestled in the heart of Naples, Florida. This charming neighborhood offers a unique blend of serene living and vibrant community spirit, making it an ideal choice for those seeking a slice of paradise. With its picturesque tree-lined streets and lush landscaping, Brookside is not just a place to live; it’s a lifestyle.

One of the standout features of Brookside is its boating community, perfect for water enthusiasts and those who appreciate the beauty of coastal living. Residents enjoy easy access to the stunning waterways of Naples, allowing for leisurely days spent on the water, whether it's fishing, kayaking, or cruising along the scenic coastline. The community’s private docks and boat ramps make it incredibly convenient for homeowners to embark on their aquatic adventures at a moment's notice.

In addition to its boating amenities, Brookside boasts a friendly atmosphere, where neighbors become friends and community events bring everyone together. Families will appreciate the proximity to top-rated schools, parks, and recreational facilities, ensuring that there’s always something to do. The nearby beaches, renowned for their powdery white sands and crystal-clear waters, are just a short drive away, providing endless opportunities for sunbathing, swimming, and enjoying the breathtaking sunsets.

With a variety of homes that cater to different tastes and lifestyles, Brookside is the perfect place to call home. Whether you’re looking for a cozy retreat or a spacious family residence, this community offers something for everyone. Experience the charm of Brookside, where boating dreams come true and community connections flourish. Your Naples oasis awaits!

Newest Brookside Homes with Boating Community Type

$1,137,000

3 Beds ⋅ 2 Baths ⋅ 226025788 MLS

BOATER'S PARADISE --- DIRECT GULF ACCESS VIA CANAL & NO FIXED BRIDGES! Significantly lower price point than other neighborhoods with direct gulf access. Blank canvass to build your own custom dock exactly the way you want it! Discover the ultimate blend of waterfront serenity and downtown convenience in this inviting Naples retreat, perfectly positioned along a Gulf-access canal. Tucked away in the desirable Brookside neighborhood, this charming residence offers an exceptional opportunity to embrace the Southwest Florida lifestyle. Wake up to peaceful water views, enjoy a morning coffee and watch passing boats that create the perfect backdrop for every day. Whether you're an avid boater or simply appreciate life on the water. This property delivers an unforgettable setting. Just moments from the vibrant energy of Fifth Avenue South and Third Street South, you'll have effortless access to award-winning restaurants, boutique shopping, galleries, and year-round entertainment. Spend afternoons exploring Bayfront, experience the creative spirit of the Bayshore Arts District, or enjoy nearby parks with scenic walking and biking trails. Historic Tin City is only minutes away, offering a unique collection of waterfront dining, local shops, and Old Florida charm. And when it's time to unwind, the sparkling Gulf waters and world-renowned white sand beaches of Naples are just a short drive away. Offering an unbeatable combination of waterfront living, prime location, and relaxed coastal elegance, this exceptional property is more than a place to live—it's your gateway to the Naples lifestyle you've been dreaming of.

2140 Harbor LN, Naples

$2,549,000

3 Beds ⋅ 3 Baths ⋅ 226025159 MLS

Waterfront Living at Its Finest – Luxury New Construction with Gulf Access Perfectly positioned on a quiet canal in Brookside, just minutes from Downtown Naples and the Gulf of Mexico, this custom-built waterfront home offers the perfect blend of modern luxury, exceptional boating, and the relaxed Southwest Florida lifestyle. Completed in 2025, this elevated residence was thoughtfully designed with quality construction, exceptional craftsmanship, and easy waterfront living in mind. The bright, open floor plan is filled with natural light and features soaring ceilings, real hardwood flooring throughout, designer finishes, and seamless indoor-outdoor living. Step outside to your own private waterfront retreat where a heated pool, authentic chickee hut, wood-fired pizza oven, built-in fire pit, floating dock, and 10,000-pound boat lift create the ideal setting for entertaining family and friends or simply unwinding after a day on the water. With direct access to Naples Bay and the Gulf of Mexico, boating, fishing, paddleboarding, kayaking, waterfront dining, and sunset cruises are all just minutes from your backyard. Designed for comfort and peace of mind, the home also features total home automation, Starlink high-speed internet, a whole-house generator, a 500-gallon propane tank, a tankless water heater, and an oversized EV-ready garage with room for two car lifts. Elevated construction offers added confidence while allowing you to spend more time enjoying everything this waterfront lifestyle has to offer. One of the few newly built, move-in-ready Gulf-access homes available at this price point, this property presents a rare opportunity to enjoy luxury waterfront living without the wait of building new. Located just minutes from Fifth Avenue South, Naples Bay, world-class beaches, fine dining, shopping, and entertainment, you'll enjoy the best of Naples both by land and by water. 1794 Holiday Lane is more than a beautiful home—it's a place where boating, entertaining, and everyday living come together in one of Naples' most desirable waterfront locations.

1794 Holiday LN, Naples

$1,485,000

3 Beds ⋅ 3 Baths ⋅ 226024675 MLS

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!

2180 Harbor LN, Naples

$975,000

225079615 MLS

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.

1138 Christopher CT, Naples

$4,250,000

225067418 MLS

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!

2505 ESTEY AVE, Naples

$1,075,000

3 Beds ⋅ 2 Baths ⋅ 225012420 MLS

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.

1796 Holiday LN, Naples

Start Your Search

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.