Brookside Real Estate

Welcome to Brookside, a hidden gem nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming neighborhood is renowned for its tranquil atmosphere, lush landscapes, and a strong sense of community, making it an ideal place to call home.

Brookside boasts a diverse mix of beautifully designed single-family homes, many of which feature stunning views of serene lakes and verdant greenery. The neighborhood’s well-maintained streets are perfect for evening strolls or morning jogs, allowing residents to soak in the warm Florida sunshine and enjoy the natural beauty that surrounds them.

One of the highlights of living in Brookside is its proximity to Naples’ vibrant downtown area, where you can explore a wealth of dining, shopping, and entertainment options. From upscale boutiques to cozy cafés, there’s something for everyone just a short drive away. The stunning white sandy beaches of the Gulf of Mexico are also within easy reach, offering residents the perfect escape for sunbathing, swimming, or simply enjoying a sunset.

Families will appreciate the excellent schools in the area, along with numerous parks and recreational facilities that cater to all ages. Whether you’re looking to enjoy a leisurely day at the park or participate in community events, Brookside fosters a welcoming environment that encourages connections among neighbors.

With its blend of natural beauty, convenient amenities, and a strong community spirit, Brookside is more than just a neighborhood; it’s a lifestyle. Come discover what makes this charming enclave in Naples the perfect place to create lasting memories.

Newest Listings in Brookside

$599,000

4 Beds ⋅ 2 Baths ⋅ 226031972 MLS

Beautifully updated 4-bedroom, 2-bath home in the heart of Naples, offering a spacious layout and a true resort-style outdoor living experience. The property features a heated pool surrounded by multiple lounging areas ideal for year-round enjoyment. Inside, the home provides bright, open living spaces with modern finishes, a well-appointed kitchen, and comfortable bedroom suites designed for both privacy and flexibility. Located just minutes from Olde Naples’ pristine beaches, 5th Avenue South, and a wide selection of shopping and dining, this residence delivers exceptional convenience for full-time or seasonal living. Its central location places Naples’ most desirable amenities right at your fingertips. Situated in a quiet neighborhood with no HOA, the property offers ample parking and easy access to local parks and major corridors. Offered turnkey furnished, this home presents a rare opportunity for buyers seeking a move-in-ready residence with strong appeal for both homeowners and investors.

1303 Delmar LN, Naples

$2,199,000

226030318 MLS

INCREDIBLE opportunity to build your dream home on Rock Creek. Lot is cleared and 227 feet of new seawall is a bonus feature. This large cul-de-sac lot is the perfect private location for the water and nature lovers who want to park the boat at home and still have beautiful views. When it's time to venture away from your beautiful new retreat, all the best of Naples is available by car or boat. You're just minutes from Fifth Avenue, Naples Bay, white sand beaches, fine dining, shopping, and entertainment. Access to the gulf is a lovely boat ride via Rock Creek. Discover this great location and be among the new construction homes in the neighborhood. Build your new home and dock and start enjoying your Naples lifestyle!

1100 Christopher CT, Naples

$648,000

3 Beds ⋅ 3 Baths ⋅ 226030633 MLS

Welcome to 2160 Holiday Lane, a beautifully renovated pool home in Brookside, one of Naples’ most rapidly evolving in-town neighborhoods. Ideally positioned approximately 1.5 miles from Downtown Naples and the white-sand beaches of the Gulf, this home offers a combination of location, lifestyle, and value. **Currently utilized as a successful short-term rental with no HOA or rental restrictions, the property also presents an opportunity for investors seeking flexibility and income potential.** Thoughtfully remodeled, the three-bedroom, three-bath residence features a light-filled, open layout with updated flooring, a stylish kitchen, refreshed baths, and an attached one-car garage. Outside, the private pool and fenced backyard create an inviting setting for relaxing, entertaining, and enjoying the Southwest Florida lifestyle year-round. What truly sets this property apart is its location. Tucked into an established residential neighborhood just minutes from Fifth Avenue South and the beach, Brookside sits alongside the Davis Boulevard corridor—an area currently experiencing significant new investment and redevelopment. With new luxury residential and waterfront projects taking shape nearby, this pocket of Naples continues to attract attention while retaining the charm and convenience of an established neighborhood. Whether searching for a full-time residence, seasonal retreat, or Naples investment, 2160 Holiday Lane offers the opportunity to own a renovated pool home remarkably close to everything that makes Naples such a desirable place to live—with the added advantage of established short-term rental use and no HOA or rental restrictions.

2160 Holiday LN, Naples

$460,000

3 Beds ⋅ 2 Baths ⋅ 226029978 MLS

LOCATION. POTENTIAL. POSSIBILITIES. WELCOME TO BROOKSIDE. What you’re really buying here isn’t just a house. It’s a location with a future! This home puts you in the heart of East Naples, surrounded by the best of the Naples lifestyle. Downtown Naples, 5th Avenue South, the beaches, Naples Pier, Naples Bay, Tin City, restaurants, shopping and entertainment are all within easy reach. And the convenience doesn’t stop there. You’re just minutes from Naples Botanical Garden, Celebration Park and East Naples Community Park, giving you easy access to recreation and entertainment while enjoying the feel of an established residential neighborhood. Inside, the home has already had some important updates, including an updated kitchen with quartz countertops and stainless-steel appliances, updated bathrooms, a tankless water heater and a newer roof. Outside, enjoy a screened lanai and a large lot, all with NO HOA fees. AND THE OPPORTUNITIES......For an owner, seasonal resident or investor, this property offers flexibility and a chance to get into Naples at a more accessible price point than many properties closer to Old Naples and the beach. Rental possibilities may include traditional long-term, seasonal or short-term strategies, subject to applicable regulations and requirements. And then - there’s Brookside’s future. With continued growth and investment throughout East Naples, the area is one to watch. Nearby development, including projects such as Halcyon along Davis Boulevard, adds another layer of potential to an already convenient location. NOW, is your chance to get into Naples, get close to everything, and explore what this location could mean for you today and down the road.

2398 Estey AVE, Naples

$2,499,000

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

$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

$439,000

2 Beds ⋅ 1.5 Baths ⋅ 226012692 MLS

Remember when Naples felt like Naples? Before master-planned communities and endless new construction, there were neighborhoods like BROOKSIDE—authentic, established, and woven into the fabric of the community. This is the Naples lifestyle people move here for—morning walks through Baker Park, a bike ride to 5th Avenue South for coffee, lunch on Naples Bay, sunset at the beach, and dinner downtown without ever feeling far from home. You can renovate a home. You can build a new one. But you can't recreate a CORNER LOT just minutes from Downtown Naples. As the city continues to evolve, locations like this only become more desirable. Beautifully RENOVATED & refreshed with updated landscaping, professional staging, and stylish upgrades throughout, 2300 Estey Avenue blends timeless charm with today's modern comforts. Inside, the open-concept layout is centered around a beautifully updated kitchen featuring white shaker cabinetry, butcher block countertops, stainless steel appliances, and a generous island designed for gathering. Outside, the fully fenced backyard offers privacy and flex-area, while the oversized paver driveway provides ample space for multiple vehicles, a boat, or weekend toys. Whether you're searching for a full-time residence, a seasonal escape, or an INVESTMENT OPPORTUNITY this is your chance to own a piece of Naples that simply can't be replicated.

2300 Estey AVE, 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.