Brookside Homes with Single Family Residence Subtype

Welcome to Brookside, a charming and picturesque subdivision nestled in the heart of Naples, Florida. This delightful community in Collier County offers a serene escape from the hustle and bustle of city life while still being conveniently close to all the amenities that Naples has to offer.

Brookside is renowned for its beautiful single-family residences, each designed to embrace the quintessential Florida lifestyle. With a variety of architectural styles, these homes exude warmth and character, making them perfect for families, retirees, or anyone looking to enjoy the sun-soaked paradise of Naples. The spacious layouts and thoughtfully designed interiors provide ample room for relaxation and entertaining, ensuring that every family member feels right at home.

The community is surrounded by lush landscaping and tranquil waterways, creating a peaceful atmosphere that invites residents to unwind and enjoy the natural beauty of their surroundings. Brookside is also conveniently located near top-rated schools, shopping centers, and dining options, making it an ideal place for families and professionals alike.

Outdoor enthusiasts will appreciate the proximity to beautiful beaches, world-class golf courses, and numerous parks, offering endless opportunities for recreation and relaxation. Whether you’re taking a leisurely stroll along the beach or enjoying a sunset picnic by the water, Brookside truly embodies the best of Naples living.

Discover your dream home in Brookside today, where comfort, community, and coastal charm await you!

Newest Brookside Homes with Single Family Residence Subtype

$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

What you’re really buying here is not just the house, but the location and future potential of Brookside. 2398 Estey Avenue is ideally located in East Naples, close to everything that makes Naples so desirable: Downtown Naples, 5th Avenue South, the beaches, Naples Pier, Naples Bay, Tin City, restaurants, shopping and entertainment. You’re also just minutes from Naples Botanical Garden, Celebration Park and East Naples Community Park, giving you the convenience of a central location while still enjoying a more residential neighborhood setting. The home itself offers several important updates, including an updated kitchen with quartz countertops and stainless-steel appliances, updated bathrooms, a tankless water heater and a 2021 roof. Sitting on an approximately 7,405-square-foot lot with a screened lanai and no HOA fees, it offers flexibility for an owner, seasonal resident or investor. From an investment perspective, Brookside is particularly interesting because it provides an opportunity to be close to the heart of Naples at a more accessible entry point than some of the more expensive areas near Old Naples and the beach. The property also has potential for short-term rental use, including the possibility of operating it as an Airbnb. Its location near the beaches, Downtown Naples, 5th Avenue South, restaurants and entertainment makes it especially attractive for visitors looking for a convenient Naples stay. For an investor, this creates the potential to explore multiple strategies, from traditional long-term rental income to seasonal or short-term vacation rentals. And there’s also future potential. Continued development and investment in East Naples, including projects such as Halcyon along Davis Boulevard, could contribute to the area's long-term appeal and desirability. The combination of Naples, location, proximity to beaches and downtown, rental potential (including short-term rental and Airbnb possibilities) and future development makes 2398 Estey Avenue an opportunity worth taking a closer look at.

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

$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.