Brookside Real Estate

Welcome to Brookside, a hidden gem nestled in the vibrant city of Naples, Florida. Known for its picturesque landscapes and friendly community, Brookside offers a unique blend of tranquility and convenience that makes it an ideal place to call home.

As you stroll through the tree-lined streets, you’ll be captivated by the charming single-family homes, many of which feature lush gardens and inviting front porches. The neighborhood is designed with a strong sense of community in mind, fostering connections among residents who take pride in their surroundings. Families, retirees, and young professionals alike find a welcoming atmosphere that truly embodies the spirit of Naples.

Brookside is perfectly situated near some of the best amenities Naples has to offer. Just a short drive away, you’ll discover pristine beaches, world-class dining, and upscale shopping at the renowned Waterside Shops. For those who enjoy outdoor activities, the nearby Naples Botanical Garden and various parks provide ample opportunities for hiking, biking, and soaking up the Florida sunshine.

Education is also a priority in Brookside, with access to highly-rated schools that cater to students of all ages. The neighborhood’s close-knit feel makes it easy for families to engage in local events and activities, ensuring that everyone feels at home.

In Brookside, you’re not just buying a home; you’re investing in a lifestyle. Experience the beauty, warmth, and community spirit that this charming neighborhood has to offer. Come and discover why Brookside is one of Naples’ most sought-after locations!

Newest Listings in Brookside

$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

$479,000

4 Beds ⋅ 3 Baths ⋅ 226025527 MLS

Welcome to this super cute and newly remodeled 3 bedroom, 2 bath home with an attached efficiency with its own private entrance. This property features an open floor plan with lots of beautiful sunlight. Don't miss out! This home is ready to be enjoyed by a new family or could be a wonderful investment, or income producing property. Don't even get me started on the location, just minutes away from the stunning Naples' beaches, 5th Ave, Tin City, Celebration Park & the Naples Botanical Garden!

2240 Estey AVE, 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

$3,695,000

6 Beds ⋅ 7.5 Baths ⋅ 226022644 MLS

Positioned on an expansive parcel spanning nearly two acres, this prime property presents a remarkable opportunity in the heart of Naples. Located just minutes from the vibrant energy of downtown, the site is zoned RMF-6 and allows for the development of up to 9 single family and 11 multi-family residential units, offering exceptional versatility for developers, investors, and visionaries alike. Surrounded by a neighborhood experiencing significant growth and transformation, the property is ideally suited for a luxury residential community, a collection of custom homes, or a private estate compound. The existing improvements are being offered at land value, creating an ideal canvas for a new owner to design and build without limitation. Enjoy the rare advantage of a peaceful setting with water access to Naples Bay while remaining within close reach of the area's most sought-after destinations, including Fifth Avenue South, white-sand Gulf beaches, world-class dining, boutique shopping, and cultural attractions. Opportunities of this size and zoning designation within such close proximity to downtown Naples are increasingly difficult to find, making this a truly exceptional investment in one of Southwest Florida's most coveted markets.

1063 SHADOWLAWN DR, 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

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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.