Bayfront Living Moments from Vanderbilt Beach
Regatta is a gated waterfront community of five condominium buildings on Vanderbilt Lagoon, at the corner of Vanderbilt Beach Road and Vanderbilt Drive in North Naples. Completed in 2000, it pairs two twelve-story towers on Flagship Drive with three six-story buildings on Launch Circle — roughly 200 three-bedroom residences with an on-site marina, resort-style pools and a rental policy that still allows weekly stays in many residences. The white sand of Vanderbilt Beach is a short distance away, and Alpizar & Company manages residences here through our property management division.
Regatta at a Glance
| Address | 400 & 410 Flagship Drive and 450, 460 & 470 Launch Circle, Naples, FL 34108 |
| Year Built | 2000 |
| Buildings | Five — two 12-story towers (400 & 410 Flagship) and three 6-story buildings (450, 460 & 470 Launch Circle) |
| Residences | 200 condominiums |
| Closed Sales | $975,000 to $1,675,000, September 2024 to September 2026 (15 sales) |
| Floor Plans | Three-bedroom residences, approximately 1,475 to 2,320 square feet; floor plans available on request |
| Waterfront | Vanderbilt Lagoon frontage with bay views; Gulf views from the upper floors of the towers |
| Marina | 55-slip marina on the lagoon; slips for lease or purchase subject to availability; fishing pier |
| Amenities | Gated entry, two pools including a lagoon-style pool with waterfall, spa, fitness center, clubhouse with social room, picnic and grilling area, extra storage, poolside cabanas for purchase |
| Rental Policy | 30-day minimum, up to 12 leases per year; many residences are grandfathered to permit weekly rentals — ask us which |
| Annual Fees | About $17,000 to $23,000 in recent listings |
| Pet Policy | Two pets, no size restrictions |
| Parking | One assigned under-building space per residence |
Regatta at Vanderbilt Beach - Active Listings
Looking for a Specific Building, Floor or View?
Regatta inventory is thin: on October 9, 2026, three residences were for sale across all five buildings. Tell us what you're looking for — building, floor, exposure, boat slip — and we'll send a curated selection, including opportunities that may not be publicly listed.
The Community
Regatta sits where Vanderbilt Beach Road meets Vanderbilt Drive, with Vanderbilt Lagoon along its northern and western edges and the Gulf of Mexico a short distance to the west. Residences open onto screened lanais facing the water, and the two Flagship Drive towers rise high enough that upper-floor homes look across the barrier island to the Gulf. Inside the gates, the five buildings share a resort-style amenity campus — two pools, a spa, a fitness center and a clubhouse — that gives the community the feel of a private beach resort rather than a condominium.
Regatta Building by Building
Fifteen Regatta residences closed between September 2024 and September 2026, from $975,000 to $1,675,000, at a median $1,300,000 and $695 a square foot. The two Flagship Drive towers carry the larger plans and the Gulf views from their upper floors, and they trade at a premium: eleven tower sales closed at a median $1,325,000, or $750 a square foot, against four Launch Circle sales at a median $1,007,500, or $618 a square foot, for residences of about 1,475 to 1,640 square feet beside the pool deck and marina.
| Building | Plans | Median |
|---|---|---|
| 400 Flagship Drive 12 floors · 80 residences |
1,734–2,035 sq ft 3BR, 2 or 3 baths |
$1,425,000 4 sales · $756/sq ft |
| 410 Flagship Drive 12 floors · 60 residences |
1,839–2,320 sq ft 3BR, some with den |
$1,325,000 7 sales · $670/sq ft |
| 450 Launch Circle 6 floors · 20 residences |
1,475–1,635 sq ft 3BR, 2 baths |
$990,000 1 sale · $606/sq ft |
| 460 Launch Circle 6 floors · 20 residences |
1,475–1,639 sq ft 3BR, 2 baths |
$1,027,500 2 sales · $662/sq ft |
| 470 Launch Circle 6 floors · 20 residences |
1,475–1,639 sq ft 3BR, 2 baths |
$975,000 1 sale · $596/sq ft |
Closed sales reported through the Naples Area Board of REALTORS® MLS, September 2024 to September 2026; medians shown in the last column.
On October 9, 2026, three Regatta residences were for sale, from a third-floor residence at 470 Launch Circle listed at $1,150,000 to $1,849,000, including an eleventh-floor residence at 400 Flagship Drive newly listed at $1,495,000. Residences closed at a median 94% of their final asking price after a median 131 days on the market, and annual association fees in recent listings run about $17,000 to $23,000.
Where Each Building Sits
The map numbers Regatta’s five buildings by address. The two high-rises, 400 Flagship Drive (1) and 410 Flagship Drive (2), line the lagoon on the west and north sides, with the 55-slip marina along the northern shore. The three six-story buildings on Launch Circle, 450 (3), 460 (4) and 470 (5), wrap the clubhouse and pools on the east side, between the towers and Vanderbilt Drive. The gated entry is on Vanderbilt Beach Road.
Regatta’s five buildings, numbered by address. Map by Alpizar & Company.
Regatta on the Map
Boating & the Marina
Regatta's 55-slip marina on Vanderbilt Lagoon is one of the community's defining advantages. Slips are available for lease or purchase as they come up, and the lagoon connects to Wiggins Pass and the Gulf for open-water boating. A fishing pier and the lagoon frontage itself make the water part of daily life whether or not you keep a boat.
Rental Appeal & Property Management
Regatta's location, amenities and rental flexibility draw seasonal renters and the owners who host them. Over the past two years, 49 seasonal listings at Regatta asked a median $14,000 a month, from about $10,000 to $18,000, and ten more were priced by the week at $3,000 to $4,000, nine of them in the Launch Circle buildings. Alpizar & Company manages residences at Regatta through Alpizar Property Management, and our Regatta vacation rentals page shows what is currently available. If you own here and are weighing a sale against continued rental income, our condo-selling guide is a good starting point.
Location
The beach access at the end of Vanderbilt Beach Road, The Ritz-Carlton, Naples, LaPlaya Beach & Golf Resort and The Turtle Club are all a short distance away. Mercato's dining and shopping is minutes east on Vanderbilt Beach Road, and Waterside Shops and Artis—Naples are a short drive south. See our Vanderbilt Beach guide for the full neighborhood picture.
Regatta and Florida’s Condo Safety Law
All five Regatta buildings fall under Florida’s condominium safety law: a milestone structural inspection at 30 years (25 where the local building official requires it) and every 10 years after, and a structural integrity reserve study every 10 years, the first of which was due by December 31, 2025. Completed in 2000, Regatta reaches the 30-year mark in 2030, so the reserve study is the document that matters now. Ask the association for the reserve study, any milestone inspection report, the current budget and any planned special assessments before you make an offer. Resale buyers also have seven days after receiving the condominium documents to cancel the contract.
Regatta at Vanderbilt Beach
Frequently Asked Questions About Regatta at Vanderbilt Beach
Where is Regatta located in Naples?
Regatta is at the corner of Vanderbilt Beach Road and Vanderbilt Drive in the Vanderbilt Beach area of North Naples, Florida 34108, on Vanderbilt Lagoon. The buildings are addressed 400 and 410 Flagship Drive and 450, 460 and 470 Launch Circle. Vanderbilt Beach and the Gulf of Mexico are a short distance to the west.
How many buildings and residences are there at Regatta?
Regatta has five buildings and about 200 residences. The two Flagship Drive towers are twelve stories — 400 Flagship has 80 residences and 410 Flagship has 60 — and the three Launch Circle buildings are six stories with 20 residences each. All five share the same gated amenity campus and marina.
What are the floor plans at Regatta?
Residences at Regatta are three-bedroom plans ranging from approximately 1,475 to 2,320 square feet, with screened lanais facing the lagoon. The largest plans are in the Flagship Drive towers. Floor plans for any building are available from us on request.
Does Regatta have Gulf views?
Every building fronts Vanderbilt Lagoon with bay views. Gulf views are found on the upper floors of the two twelve-story Flagship Drive towers, which look across the Vanderbilt Beach barrier island to the water. The six-story Launch Circle buildings offer lagoon and marina views, with partial Gulf views from some upper-floor residences.
What is the rental policy at Regatta?
The standard policy allows leases of 30 days or longer, up to 12 times per year. A significant number of residences are grandfathered to permit weekly rentals, so short-term rental income is possible in those residences. Whether a particular residence carries weekly-rental rights is something to confirm before you buy — we can tell you which units do.
Can I keep a boat at Regatta?
Yes. Regatta has a 55-slip marina on Vanderbilt Lagoon with slips available for lease or purchase subject to availability. The lagoon leads to Wiggins Pass and the Gulf of Mexico. Slips are not automatically included with a residence, so ask us about slip availability for any home you are considering.
What amenities does Regatta offer?
Regatta is gated and offers two pools including a lagoon-style pool with a waterfall, a spa, a fitness center, a clubhouse with a social room, a fishing pier, a picnic and grilling area, extra storage, and poolside cabanas that can be purchased when available. Each residence has one assigned under-building parking space. Two pets are permitted with no size restrictions.
Does Alpizar & Company manage rentals at Regatta?
Yes. Alpizar Property Management manages residences at Regatta for owners who rent seasonally, handling marketing, guest screening, turnover and owner reporting. If you own at Regatta and want to discuss rental management, or you are a buyer weighing the income side of a purchase, call us at (239) 438-1102.
What do condos at Regatta sell for?
Fifteen residences sold between September 2024 and September 2026, from $975,000 to $1,675,000, at a median $1,300,000 or $695 a square foot. Tower residences at 400 and 410 Flagship Drive sold at a median $1,325,000 and Launch Circle residences at a median $1,007,500.
What are the association fees at Regatta?
Total annual association fees in recent Regatta listings run about $17,000 to $23,000, depending on the building and the size of the residence. Confirm the current budget and any special assessments with the association before purchasing.
How does Florida’s condo safety law affect Regatta?
Buildings of three stories or more need a milestone structural inspection at 30 years (25 where the local building official requires it) and every 10 years after, plus a structural integrity reserve study every 10 years, the first due by December 31, 2025. Regatta, completed in 2000, reaches the 30-year mark in 2030. Ask for the latest reserve study, the current budget and any planned special assessments before you buy. Resale buyers have seven days after receiving the condominium documents to cancel.
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Alpizar & Company is a family-owned independent brokerage specializing in luxury waterfront real estate in Naples, Marco Island and Bonita Springs. Led by Robert Alpizar (CLHMS, GRI, SRS, PSA) and Marlene Alpizar, our team operates as advisors — not salespeople — guiding buyers and sellers with firsthand local expertise and no corporate quotas.
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