Vanderbilt Beach Homes

• 

  

  

  /47

  $2,550,000

  $849K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,344 Sq Ft

  274 Conners Ave, Naples, FL 34108

  SIGNIFICENT PRICE REDUCTION -- NOW IS THE TIME!!!!!! RARE OPPERTUNITY TO PURCHASE A BAY FRONT SOUTHERN EXPOSURE HOME, AND NOT ONLY IS EVERYTHING IN THIS HOME BRAND NEW, BUT WITHOUT A DOUBT IT IS ALL ABOUT THE VIEW!!! If you are lucky enough have the opportunity to call Vanderbilt Beach your home, and you want a very spacious 2344 sq. ft. home with a 2 car garage, complete with boat dock and huge

  

  Sue Myhelic

  Gulf Breeze Real Estate LC

  (239) 282-4734

  274 Conners Ave, Naples, FL 34108
• Explore Vanderbilt Beach

• 

  

  

  /26

  $14,000 Per Month

  • 3 Beds
  • 3 Baths
  • 2,035 Sq Ft
  • Condo for Rent

  400 Flagship Dr Unit 403, Naples, FL 34108

  Life is Good at The REGATTA! One Block to Naples Pristine Beach with a Great View! Naples Florida is ranked among the Top 10 Florida vacation destinations by US NEWS & WORLD REPORT! Luxury 3BD/3BA with a spectacular panoramic water view is the perfect vacation rental for beachcombers and boaters at VANDERBILT BEACH ! Enjoy sunsets from your lanai overlooking the bay, boats, the pool and patio

  

  Laurie Bellico

  William Raveis Real Estate

  (239) 456-2781

  400 Flagship Dr Unit 403, Naples, FL 34108
• 

  

  /2

  $2,975,000

  Sold Aug 18, 2025

  9811 Gulf Shore Dr Unit 301, Naples, FL 34108

  • 3 Beds
  • 3.5 Baths
  • 2,991 Sq Ft
  • Built 1994

  Last Sold Summary

  • 23% Below List Price
  • $995/SF
  • 187 Days On Market

  Current Estimated Value $3,333,555

  Last Listing Agent Mari Vesci John R Wood Properties

  9811 Gulf Shore Dr Unit 301, Naples, FL 34108
• 

  

  

  /48

  Est $1,711,476

  Not Listed For Sale

  10701 Gulf Shore Dr Unit 800, Naples, FL 34108

  • 3 Beds
  • 3 Baths
  • 1,940 Sq Ft
  • Built 1981

  10701 Gulf Shore Dr Unit 800, Naples, FL 34108

  Last Sold Summary

  • 17 Days On Market
• 

  

  

  /50

  $6,995,000

  • 5 Beds
  • 6 Baths
  • 4,350 Sq Ft

  380 Trade Winds Ave, Naples, FL 34108

  Completely reimagined and masterfully curated, this exceptional waterfront residence offers approximately 4,350 total square feet of refined living space, featuring 5 bedrooms, 6 bathrooms, and an expansive 8-car garage designed for car enthusiasts and elevated storage. Designed with a focus on modern elegance, seamless indoor-outdoor living, and full smart home integration, every detail has been

  

  Steve Buchalter

  Coldwell Banker Realty

  (239) 785-1101

  380 Trade Winds Ave, Naples, FL 34108
• 

  

  /19

  $8,500 Per Month

  • 3 Beds
  • 3 Baths
  • 1,760 Sq Ft
  • Condo for Rent

  400 Flagship Dr Unit 1206, Naples, FL 34108

  Luxury Penthouse Living at Vanderbilt Beach Furnished 3 bedroom, 3 bathroom penthouse in Regatta with double car garage is just moments from the white sands of Vanderbilt Beach. Available April 1st for annual rental, this residence offers sweeping water views and exceptional privacy from its top floor vantage point. Light-filled living spaces with 9 ft ceilings is open to a large screened lanai

  (239) 206-1677

  400 Flagship Dr Unit 1206, Naples, FL 34108
• 

  

  /44

  $4,495,000

  Sold Jan 12, 2026

  239 Channel Dr, Naples, FL 34108

  • 5 Beds
  • 4.5 Baths
  • 4,050 Sq Ft
  • Built 2000

  Last Sold Summary

  • 2% Below List Price
  • $1,110/SF
  • 16 Days On Market

  Current Estimated Value $4,458,342

  Last Listing Agent Shawn Stuben Shawn Stuben Naples Properties

  239 Channel Dr, Naples, FL 34108
• 

  

  /50

  Est $6,360,096

  Not Listed For Sale

  11125 Gulf Shore Dr Unit 405, Naples, FL 34108

  • 3 Beds
  • 3.5 Baths
  • 4,001 Sq Ft
  • Built 2009

  11125 Gulf Shore Dr Unit 405, Naples, FL 34108

  Last Sold Summary

  • 65 Days On Market
• 

  

  /50

  $2,195,000

  $255K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,146 Sq Ft

  493 Willet Ave, Naples, FL 34108

  A rare investment opportunity and the only multifamily-style residence currently available in the entire Connors area of Vanderbilt Beach. This exceptional Gulf-access waterfront property offers versatility, usability, and long-term value, set on an oversized corner lot with approximately 105 feet of canal frontage. Constructed of concrete block and designed as a single-story residence, the

  

  Steve Buchalter

  Coldwell Banker Realty

  (239) 256-2335

  493 Willet Ave, Naples, FL 34108
• 

  

  /35

  $8,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft
  • Condo for Rent

  11030 Gulf Shore Dr Unit 202, Naples, FL 34108

  Taken for SEASON 2027 but available May 1 to Dec '26 and April '27 forward. Gulf & Bay Views! Private Beach Access! Step into a realm of sophistication as you enter this spacious three-bedroom corner unit in a great Community with many Amenities. Floor-to-ceiling, wrap-around (hurricane-grade) glass doors showcase sparkling views of the Gulf and mesmerizing sunsets from inside or out on the huge

  

  Allison Callas

  Downing Frye Realty Inc.

  (239) 933-6018

  11030 Gulf Shore Dr Unit 202, Naples, FL 34108
• 

  

  /32

  $1,825,000

  Sold Mar 25, 2026

  10691 Gulf Shore Dr Unit 500, Naples, FL 34108

  • 3 Beds
  • 2 Baths
  • 1,967 Sq Ft
  • Built 1982

  Last Sold Summary

  • 6% Below List Price
  • $928/SF
  • 35 Days On Market

  Current Estimated Value $1,862,656

  Last Listing Agent Nick Rigoni Premiere Plus Realty Company

  10691 Gulf Shore Dr Unit 500, Naples, FL 34108
• 

  

  /22

  Est $365,159

  Not Listed For Sale

  377 Vanderbilt Beach Rd Unit 303, Naples, FL 34108

  • Studio
  • 1 Bath
  • 650 Sq Ft
  • Built 1982

  377 Vanderbilt Beach Rd Unit 303, Naples, FL 34108

  Last Sold Summary

  • 564 Days On Market
• 

  

  /49

  $2,150,000

  • 2 Beds
  • 2.5 Baths
  • 1,855 Sq Ft

  10701 Gulf Shore Dr Unit 901, Naples, FL 34108

  Rarely available 9th-floor “01 stack” beachfront residence in Vanderbilt Shores offering breathtaking 270-degree views of the Gulf. This professionally remodeled and beautifully appointed condominium makes an immediate impression from the moment you enter. Perched on the 9th floor, this residence offers a truly captivating experience, where evenings are best spent on your spacious, exceptionally

  

  Robert Nardi

  WeichertRealtors-ParadiseHomes

  (239) 984-9865

  10701 Gulf Shore Dr Unit 901, Naples, FL 34108
• 

  

  /20

  $4,320

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 581 Sq Ft
  • Condo for Rent

  260 Southbay Dr Unit SI FL2-ID1226371P, Naples, FL 34108

  The advertised rate of $4,320/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 4, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  (239) 388-3428

  260 Southbay Dr Unit SI FL2-ID1226371P, Naples, FL 34108
• 

  

  /50

  $4,200,000

  Sold Nov 24, 2025

  279 Heron Ave, Naples, FL 34108

  • 4 Beds
  • 6 Baths
  • 4,534 Sq Ft
  • Built 2020

  Last Sold Summary

  • 22% Below List Price
  • $926/SF
  • 156 Days On Market

  Current Estimated Value $4,437,471

  Last Listing Agent Ashley Silvers William Raveis Real Estate

  279 Heron Ave, Naples, FL 34108
• 

  

  /21

  Not Listed For Sale

  287 Trade Winds Ave Unit 24, Naples, FL 34108

  287 Trade Winds Ave Unit 24, Naples, FL 34108

  Last Sold Summary

  • 20 Days On Market
• 

  

  /50

  $4,495,000

  Open Sat 1PM - 3PM

  • 5 Beds
  • 3.5 Baths
  • 4,042 Sq Ft

  390 Oak Ave, Naples, FL 34108

  Nestled in the highly coveted Vanderbilt Beach area of North Naples, this exceptional water front residence in Conners showcases sweeping bay views and the very best of coastal luxury living. Just moments from the renowned Ritz-Carlton, area shopping, dining and the pristine white-sand beaches that define the Naples lifestyle, the location is simply unmatched.Enjoy direct Gulf access from

  

  John Robert III

  John R Wood Properties

  (239) 695-6701

  390 Oak Ave, Naples, FL 34108
• 

  

  /38

  $17,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Condo for Rent

  10701 Gulf Shore Dr Unit 1002, Naples, FL 34108

  Available for January & February 2026! Experience the ultimate in coastal luxury with this stunning 10th-floor beachfront condo at The Seville, located in the prestigious Vanderbilt Shores high-rise in Naples. Rarely available, this beautifully situated residence showcases panoramic, west-facing views of the Gulf of Mexico from an expansive private balcony, perfect for soaking in breathtaking

  

  Robert Nardi

  WeichertRealtors-ParadiseHomes

  (239) 428-0628

  10701 Gulf Shore Dr Unit 1002, Naples, FL 34108
• 

  

  /29

  $4,150,000

  Sold Sep 10, 2025

  9715 Gulf Shore Dr Unit 702, Naples, FL 34108

  • 3 Beds
  • 3.5 Baths
  • 2,354 Sq Ft
  • Built 1980

  Last Sold Summary

  • 5% Below List Price
  • $1,763/SF
  • 42 Days On Market

  Current Estimated Value $4,012,473

  Last Listing Agent Lorena Nunez Premiere Plus Realty Company

  9715 Gulf Shore Dr Unit 702, Naples, FL 34108
• 

  

  /46

  Est $1,323,624

  Not Listed For Sale

  9375 Gulf Shore Dr Unit 502, Naples, FL 34108

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1981

  9375 Gulf Shore Dr Unit 502, Naples, FL 34108

  Last Sold Summary

  • 271 Days On Market
• 

  

  /50

  $999,000

  $1M PRICE DROP Pending

  • 3 Beds
  • 3 Baths
  • 2,500 Sq Ft

  10562 Gulf Shore Dr Unit 101/102, Naples, FL 34108

  HUGE PRICE CORRECTION! Welcome to luxury condo living at its finest! 1031 Exchange need to sell. Imagine waking up to breathtaking sunrise with an unobstructed view of Vanderbilt Bay while having your boat in your backyard. Gulf Cove, at Vanderbilt beach, offers gorgeous panoramic views of the bay as well as the gulf. This beautifully maintained condo offers 3 bedrooms, and 3 huge bathrooms. For

  

  Cynthia 'Cindy' Brown

  Gulf Coast Living Real Estate, Inc

  (239) 932-7218

  10562 Gulf Shore Dr Unit 101/102, Naples, FL 34108
• 

  

  /18

  $4,320

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 904 Sq Ft
  • Condo for Rent

  260 Southbay Dr Unit SI FL2-ID1226374P, Naples, FL 34108

  The advertised rate of $4,320/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 10, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  (239) 518-3131

  260 Southbay Dr Unit SI FL2-ID1226374P, Naples, FL 34108
• 

  

  /40

  $1,545,000

  Sold Jan 23, 2026

  10701 Gulf Shore Dr Unit 1101, Naples, FL 34108

  • 2 Beds
  • 3 Baths
  • 1,855 Sq Ft
  • Built 1981

  Last Sold Summary

  • 9% Below List Price
  • $833/SF
  • 40 Days On Market

  Current Estimated Value $1,567,049

  Last Listing Agent Nick Rigoni Premiere Plus Realty Company

  10701 Gulf Shore Dr Unit 1101, Naples, FL 34108
• 

  

  /10

  Est $1,253,935

  Not Listed For Sale

  9375 Gulf Shore Dr Unit 304, Naples, FL 34108

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1981

  9375 Gulf Shore Dr Unit 304, Naples, FL 34108

  Last Sold Summary

  • 83 Days On Market
• 

  

  /11

  $7,995,000

  $1M PRICE INCREASE

  • 5 Beds
  • 8 Baths
  • 4,695 Sq Ft

  489 Heron Ave, Naples, FL 34108

  This Conners Vanderbilt new construction 5 bedroom plus flex room, 6 full, and 2 half bath home offers it all: located on extra wide 92' canal lot with new taller sea wall and new dock will feature a boat house with 20,000lb lift and separate dock for two Jet Skis with easy access to the Gulf of Mexico, an easy walk or bike to Vanderbilt Beach, light coastal design with decorator furnishings

  Barry DeNicola Barry DeNicola Realty Inc

  489 Heron Ave, Naples, FL 34108
• 

  

  /18

  $14,000 Per Month

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft
  • Condo for Rent

  10851 Gulf Shore Dr Unit 301, Naples, FL 34108

  Welcome to Vanderbilt Gulfside, one of Naples’ most loved beachfront communities, where eight acres of beautifully landscaped grounds meet the soft white sands of Vanderbilt Beach. This three-bedroom, three-bathroom corner residence captures the timeless charm of coastal Florida living — comfortable, spacious, and filled with natural light from its coveted southwest exposure. From the moment you

  Bridget Sypolt Coldwell Banker Realty

  10851 Gulf Shore Dr Unit 301, Naples, FL 34108
• 

  

  /18

  $935,000

  Sold Dec 22, 2025

  10682 Gulf Shore Dr Unit 302, Naples, FL 34108

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Below List Price
  • $749/SF
  • 131 Days On Market

  Current Estimated Value $932,061

  Last Listing Agent Tony Grech Compass Florida LLC

  10682 Gulf Shore Dr Unit 302, Naples, FL 34108
• 

  

  /34

  Est $1,394,635

  Not Listed For Sale

  9375 Gulf Shore Dr Unit 604, Naples, FL 34108

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • Built 1981

  9375 Gulf Shore Dr Unit 604, Naples, FL 34108

  Last Sold Summary

  • 7 Days On Market
• 

  

  /29

  $1,699,000

  • 3 Beds
  • 2 Baths
  • 1,546 Sq Ft

  9700 Gulf Shore Dr Unit 202, Naples, FL 34108

  Majestic views of the Bay & Gulf from this updated Vanderbilt Beach condo that comes with a DEEDED BOAT SLIP WITH 24,000. This unit boasts never-ending trade winds year-round! Delight in front row seats to unobstructed sunrises from the spacious screen lanai that runs the length of your home & sunsets from right outside your front door. The upgraded master ensuite bath boasts double vanities,

  Ryan Schwartz Naples Homes

  9700 Gulf Shore Dr Unit 202, Naples, FL 34108
• 

  

  /47

  $13,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,315 Sq Ft
  • Townhouse for Rent

  10475 Gulf Shore Dr, Naples, FL 34108

  Apply here NOW: Monthly seasonal rate: $13,000 (minimum 2 weeks).Beachfront Bliss in NaplesDiscover the ultimate Gulf-front escape at 10475 Gulf Shore Drive. This elegant mid-rise condo boasts stunning water views, a bright and open living space, and a private balcony perfect for enjoying Florida sunsets. The modern kitchen, spacious bedrooms, and master suite with

  10475 Gulf Shore Dr, Naples, FL 34108
• 

  

  /26

  $710,000

  Sold Oct 09, 2025

  10562 Gulf Shore Dr Unit 402, Naples, FL 34108

  • 2 Beds
  • 2 Baths
  • 1,178 Sq Ft
  • Built 1984

  Last Sold Summary

  • 5% Below List Price
  • $603/SF
  • 139 Days On Market

  Current Estimated Value $727,141

  Last Listing Agent Ryan Schwartz Naples Homes

  10562 Gulf Shore Dr Unit 402, Naples, FL 34108
• 

  

  /3

  Est $2,631,915

  Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 2 Baths
  • 2,142 Sq Ft
  • Built 1968

  Unlisted Address

  Last Sold Summary

  • 0 Days On Market
• 

  

  /37

  $2,149,000

  Open Sat 1PM - 3PM $150K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,082 Sq Ft

  9566 Gulf Shore Dr Unit 201, Naples, FL 34108

  Million-dollar views of Vanderbilt Bay are included with this purchase. It’s difficult to describe the mesmerizing, postcard views that create the feel of a serene coastal retreat from this 2,082-square-foot, end-unit condominium. This residence is in Vanderbilt Beach with full beach access located directly across the street. You’ll enjoy convenience of walking to The Turtle Club, La Playa, Ritz

  John R. D'Amelio AIA Premier Sotheby's Int'l Realty

  9566 Gulf Shore Dr Unit 201, Naples, FL 34108
• 

  

  /33

  $18,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft
  • Condo for Rent

  10525 Gulf Shore Dr Unit 251, Naples, FL 34108

  Live the Naples dream at Gulfshores at Vanderbilt Beach, where the Gulf of Mexico is just steps away and one of the best community pools on thebeach awaits. This furnished 3-bedroom, 2-bath condo offers over 1,500 square feet of coastal living with an open floor plan, tile flooring in themain areas, and carpet in the bedrooms. The updated kitchen and dining area flow into a spacious

  Ryan Schwartz Naples Homes

  10525 Gulf Shore Dr Unit 251, Naples, FL 34108
• 

  

  /28

  $22,050,000

  Sold Mar 25, 2026

  10047 Gulf Shore Dr, Naples, FL 34108

  • 9,000 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Above List Price
  • $2,450/SF
  • 99 Days On Market

  Current Estimated Value $8,086,036

  Last Listing Agent Michael Sopka Compass Florida LLC

  10047 Gulf Shore Dr, Naples, FL 34108
• 

  

  /21

  Est $2,666,904

  Not Listed For Sale

  287 Trade Winds Ave, Naples, FL 34108

  • Built 1967

  287 Trade Winds Ave, Naples, FL 34108

  Last Sold Summary

  • 7 Days On Market
• 

  

  /32

  $12,895,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 5,367 Sq Ft

  348 Seagull Ave, Naples, FL 34108

  Introducing a landmark property in one of Naples’ most coveted boating communities, 348 Seagull Avenue redefines modern coastal luxury. Perfectly positioned at the tip of a quiet cul-de-sac in the exclusive Conners enclave of Vanderbilt Beach, this architectural masterpiece by Kriel Dillworth Design commands a pie-shaped lot with wide, unobstructed canal views and coveted western exposure, the

  Melissa Martin Gulf Coast International Prop

  348 Seagull Ave, Naples, FL 34108
• 

  

  /8

  $1,750 Per Month

  • Studio
  • 1 Bath
  • 666 Sq Ft
  • Townhouse for Rent

  377 Vanderbilt Beach Rd, Naples, FL 34108

  Welcome to Vanderbilt Hideaway! This renovated and spacious studio residence offers a beautifully designed coastal interior paired with peaceful canal views, creating the perfect setting for a relaxing Southwest Florida getaway. Thoughtfully decorated and fully stocked for incoming guests, the unit is designed to make your stay effortless and comfortable from the moment you arrive. Ideally

  377 Vanderbilt Beach Rd, Naples, FL 34108
• 

  

  /30

  $2,600,000

  Sold May 15, 2026

  404 Bayside Ave, Naples, FL 34108

  • 4 Beds
  • 4.5 Baths
  • 3,026 Sq Ft
  • Built 1995

  Last Sold Summary

  • 19% Below List Price
  • $859/SF
  • 115 Days On Market

  Current Estimated Value $2,899,150

  Last Listing Agent Kimberly Salay John R Wood Properties

  404 Bayside Ave, Naples, FL 34108
• 

  

  /49

  Est $4,152,089

  Not Listed For Sale

  404 Seagull Ave, Naples, FL 34108

  • 5 Beds
  • 6 Baths
  • 4,166 Sq Ft
  • Built 2013

  404 Seagull Ave, Naples, FL 34108

  Last Sold Summary

  • 72 Days On Market

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