The community of Brookside is situated in Naples. Ideally situated for access to all of the Naples area amenities and advantages available.

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Single Family Residence for Sale in Brookside

Active 1363 Barbizon Ln   Naples
32 photos

List Price:  $435,000

Here’s a polished, professional, and friendly property description: --- Welcome to this beautifully renovated 2-bedroom, 2-bath home located at the end of a quiet cul-de-sac in the desirable Brookside community. Just 3 miles from the beach, this property offers the perfect blend of modern coastal style and convenient location. The home has been thoughtfully updated throughout, featuring new…

1032 2 1961
Courtesy of Clever Home Selling

Single Family Residence for Sale in Brookside

Active 1063 Shadowlawn Dr   Naples
20 photos

List Price:  $3,695,000

Nearly 2 acres just minutes from downtown Naples—an exceptional development opportunity zoned for up to 11 residences! Set in a rapidly evolving area, this expansive property offers a rare chance to create a private enclave of luxury homes or a boutique residential development in one of Naples’ most desirable locations. With RMF-6 zoning allowing for…

4921 6 | 2 1948
Courtesy of William Raveis Real Estate

Single Family Residence for Sale in Brookside

Active 2047 Harbor Ln   Naples
26 photos

List Price:  $2,900

Single family home in a Prime Naples Location! Exceptional opportunity to rent an updated 3BR/2BA home with a new landscape and irrigation system recently added in the heart of Naples, just moments from 5th Avenue's world-class dining, shopping, and the white sands of Naples Beach. With this fully furnished, turn-key property is ready for…

1540 2 1963
Courtesy of Premiere Plus Realty Company

Single Family Residence for Sale in Brookside

Active 1303 Delmar Ln   Naples
17 photos

List Price:  $624,000

Beautifully updated 4-bedroom, 2-bath home in the heart of Naples, offering a spacious layout and a resort-style outdoor living experience. The property features a heated pool and multiple lounging areas ideal for year-round enjoyment. Inside, the home provides a bright, open living space with modern finishes, a well-appointed kitchen, and comfortable bedroom suites designed for…

2160 2 1961
Courtesy of Brodersen LLC

Single Family Residence for Sale in Brookside

Active 2300 Estey Ave   Naples
31 photos

List Price:  $449,000

Welcome to 2300 Estey Ave in Naples—a beautifully updated home that blends modern finishes with relaxed Florida living. From the moment you arrive, you’ll appreciate the clean curb appeal, oversized paver driveway, and fully fenced yard offering both privacy and plenty of space. Step inside to discover a bright, open-concept layout featuring rich wood-look flooring,…

1280 1 | 1 1961
Courtesy of Compass Florida LLC

Single Family Residence for Sale in Brookside

Active 1836 Harbor Ln   Naples
40 photos

List Price:  $9,000

Available for long-term lease! Completely renovated waterfront residence ideally positioned just minutes from Naples Bay and the world-class dining, shopping, and entertainment of 5th Avenue South. This exceptional two-story home offers a versatile layout designed to accommodate a variety of living arrangements. The upper level serves as the primary living space, showcasing a spacious open-concept design…

3750 4 | 1 2024
Courtesy of Naples Vacation Properties

Single Family Residence for Sale in Brookside

Active 1712 Harbor Ln   Naples
20 photos

List Price:  $1,950,000

Amazing Waterfront property!!! Enjoy great fishing and regular Dolphin and Manatee encounters!!! Expansive waterfront property with Gulf access, surrounded by protected mangroves, providing total seclusion. Interior features include updated impact windows, newer roof and a total renovation full of charm. Exterior features include banana plants with lush tropical landscape , a large pool with spa…

1788 2 1963
Courtesy of Downing Frye Realty Inc.

Single Family Residence for Sale in Brookside

Active 2048 Harbor Ln   Naples
35 photos

List Price:  $22,500

Harbor Lane Bungalow is a waterfront mid-century modern single family home in the downtown Naples neighborhood of Brookside. A beautiful heated pool and hot tub overlook the gulf-access canal where you have a newly rebuilt private boat dock with lift. The location is super convenient - less than 5 minutes drive to 5th Ave S,…

1847 2 1961
Courtesy of John R Wood Properties

for Sale in Brookside

Active 2505 Estey Ave   Naples
10 photos

List Price:  $4,250,000

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…

Courtesy of William Raveis Real Estate

Single Family Residence for Sale in Brookside

Active 2047 Harbor Ln   Naples
27 photos

List Price:  $485,000

Dream Home or Turnkey Investment – Prime Naples Location! Exceptional opportunity to own a beautifully updated 3BR/2BA home with a new landscape and irrigation system recently added in the heart of Naples, just moments from 5th Avenue's world-class dining, shopping, and the white sands of Naples Beach. With a strong short-term rental history, this fully…

1540 2 1963
Courtesy of Premiere Plus Realty Company

Single Family Residence for Sale in Brookside

Active 1796 Holiday Ln   Naples
30 photos

List Price:  $1,075,000

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…

1523 2 1964
Courtesy of Daane Properties LLC

Single Family Residence for Sale in Brookside

Active 1159 Holiday Ln E  Naples
47 photos

List Price:  $1,195,000

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…

1779 2 1962
Courtesy of Premiere Plus Realty Company

Single Family Residence for Sale in Brookside

Active 1798 Holiday Ln   Naples
31 photos

List Price:  $3,625,000

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…

5860 4 2026
Courtesy of Serhant-Naples

Single Family Residence for Sale in Brookside

Active 1820 Holiday Ln   Naples
50 photos

List Price:  $1,995,000

This exquisitely renovated 3-bedroom, 3-bath canal-front residence showcases exceptional craftsmanship, thoughtful design, and effortless waterfront living—just minutes from the renowned dining, shopping, and cultural destinations of downtown Naples. No expense was spared in the complete transformation of this home, where every detail has been carefully curated to deliver both sophistication and functionality. The chef’s kitchen features…

2392 2 | 1 1965
Courtesy of Coldwell Banker Realty

for Sale in Brookside

Active 1138 Christopher Ct   Naples
19 photos

List Price:  $995,000

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…

Courtesy of John R Wood Properties

for Sale in Brookside

Active  Terrace Ave   Naples
9 photos

List Price:  $1,350,000

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…

Courtesy of Gulf Coast International Prop

Single Family Residence for Sale in Brookside

Active 2180 Harbor Ln   Naples
45 photos

List Price:  $1,485,000

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…

1813 3 1962
Courtesy of Douglas Elliman Florida,LLC

Single Family Residence for Sale in Brookside

Active 1794 Holiday Ln   Naples
42 photos

List Price:  $2,595,000

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’…

3189 3 2025
Courtesy of Douglas Elliman Florida,LLC

Single Family Residence for Sale in Brookside

Active 1971 Holiday Ln   Naples
26 photos

List Price:  $9,000

2025: OCT/NOV $4500/mo, DEC 1-25th $4500, 2026: MAR/APR $9000/mo, MAY/JUN/JUL/AUG/SEPT/OCT/NOV: $4500/mo. Available on short term basis for periods of less than 1 month if desired, please inquire for specific pricing. Completely renovated coastal bungalow in Naples’ charming Brookside neighborhood located only a short bike ride from downtown Old Naples’ white sand beaches, shopping…

3469 2 1965
Courtesy of William Raveis Real Estate

Single Family Residence for Sale in Brookside

Active 2048 Holiday Ln   Naples
28 photos

List Price:  $9,000

Discover the ultimate vacation retreat at Holiday Lane, a spacious pool home adorned with bright, modern furnishings that create an inviting and stylish atmosphere. Ideal for your Southwest Florida escape, this beautiful property offers the perfect blend of comfort, ease, and convenience. With four generously-sized bedrooms, this home accommodates up to eight guests in total…

2830 3 1965
Courtesy of John R Wood Properties

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