Vanderbilt Beach Homes

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  $2,700,000

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

  274 Conners Ave, Naples, FL 34108

  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 pool, look no further!!! ALL RECONSTRUCTION WAS DONE

  

  Sue Myhelic

  Gulf Breeze Real Estate LC

  (239) 282-4734

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

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  /25

  $10,000 per month

  • 2 Beds
  • 2 Baths
  • 1,476 Sq Ft
  • Condo for Rent

  11116 Gulf Shore Dr Unit 801, Naples, FL 34108

  Enjoy sunrises over Vanderbilt Bay and sunsets over the Gulf of Mexico in this 8th floor end-unit in The Vanderbilt Landings. This condo residence has wraparound windows providing excellent panoramic views. Upgrades include black tile flooring and newly installed Berber carpeting, as well as black granite kitchen counter tops. The split-bedroom floor plan includes two bedrooms and two baths, a

  

  David Puskaric

  Parkline Realty

  (239) 426-9135

  11116 Gulf Shore Dr Unit 801, Naples, FL 34108
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  /29

  $900,000 Sold Apr 17, 2025

  10482 Gulf Shore Dr Unit 243, Naples, FL 34108

  • 2 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 1980

  Last Sold Summary

  • 18% Below List Price
  • $594/SF
  • 64 Days On Market

  Current Estimated Value $901,926

  Last Listing Agent Nick Rigoni Premiere Plus Realty Company

  10482 Gulf Shore Dr Unit 243, Naples, FL 34108
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  /21

  Est $2,716,956 Not Listed For Sale

  287 Trade Winds Ave, Naples, FL 34108

  287 Trade Winds Ave, Naples, FL 34108
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  /20

  $895,000

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft

  10682 Gulf Shore Dr Unit 205, Naples, FL 34108

  Investor’s dream or ideal second home! Already secured with $20K+ in bookings for Jan/Feb 2026, it’s a true income opportunity. This bayfront condo delivers both lifestyle and income with breathtaking bay views, direct beach access across from Vanderbilt Beach, and a generous rental policy allowing up to 12 rentals per year (30-day minimum). Renovated in a contemporary coastal style, this turnkey

  

  Blair White

  John R Wood Properties

  (239) 829-9095

  10682 Gulf Shore Dr Unit 205, Naples, FL 34108
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  /48

  $9,600 per month

  • 6 Beds
  • 6.5 Baths
  • 4,420 Sq Ft
  • House for Rent

  405 Trade Winds Ave, Naples, FL 34108

  Amazing waterfront residence with pool, spa, boat dock and lift with direct Gulf Access. Beautiful view of the canal that opens to the pool and spa to enjoy the sunset. Elegant entry/foyer, formal dining room, family room with fireplace just to mention some of the features of this gorgeous Naples Home. There is a convenient office/den and guest bedroom on the main floor with full baths and an

  

  Annette Echeverria

  Premiere Plus Realty Company

  (239) 666-7189

  405 Trade Winds Ave, Naples, FL 34108
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  /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 $3,059,337

  Last Listing Agent Mari Vesci John R Wood Properties

  9811 Gulf Shore Dr Unit 301, Naples, FL 34108
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  /21

  Not Listed For Sale

  287 Trade Winds Ave Unit 24, Naples, FL 34108

  287 Trade Winds Ave Unit 24, Naples, FL 34108
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  /28

  $21,000,000 Pending

  • 9,000 Sq Ft

  10047 Gulf Shore Dr, Naples, FL 34108

  Seize this unparalleled opportunity to build your dream home right on the coveted sands of Vanderbilt Beach in North Naples. This exceptional Gulf Front lot boasts approximately 100 feet of pristine beachfront, offering an extraordinary setting for a life of sun, sand, and surf. Only available beachfront lot on Vanderbilt Beach! Experience the luxury of designing a home tailored to your every

  

  Michael Sopka

  Compass Florida LLC

  (239) 579-7723

  10047 Gulf Shore Dr, Naples, FL 34108
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  /27

  $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
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  /31

  $2,125,000 Sold Feb 07, 2025

  9790 Gulf Shore Dr Unit 105, Naples, FL 34108

  • 2 Beds
  • 2 Baths
  • 1,796 Sq Ft
  • Built 1996

  Last Sold Summary

  • 16% Below List Price
  • $1,183/SF
  • 16 Days On Market

  Current Estimated Value $1,983,940

  Last Listing Agent Vito Bauer Coldwell Banker Realty

  9790 Gulf Shore Dr Unit 105, Naples, FL 34108
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  /34

  Est $1,286,976 Not Listed For Sale

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

  9375 Gulf Shore Dr Unit 604, Naples, FL 34108

  9375 Gulf Shore Dr Unit 604, Naples, FL 34108
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  /25

  $5,950,000

  • Land
  • 0.37 Acre
  • $16,081,081 per Acre

  140 Flamingo Ave, Naples, FL 34108

  Rare Oversized Gulf Access Lot – Conners at Vanderbilt Beach. Incredible opportunity to own one of the last oversized end lots in the highly desirable Conners/Vanderbilt Beach community. Located at the end of a quiet cul-de-sac, 140 Flamingo Ave features 0.37 acres of premium waterfront land and an impressive 191 feet of water frontage — a boater’s dream with southwest exposure for year-round

  

  Matt Bianchini

  Compass Florida LLC

  (239) 539-6874

  140 Flamingo Ave, Naples, FL 34108
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  /19

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft
  • Condo for Rent

  271 Southbay Dr Unit 153, Naples, FL 34108

  Property Id: 2220943INCREDIBLE BAY VIEW and BOAT SLIP INCLUDED! Beach access is only steps away. This adorable TURNKEY condo features an updated kitchen, crown molding, and tile flooring throughout. Upgraded Impact Windows provide hurricane protection and plantation shutters give the condo an additional level of elegance. The living room has been extended and lanai closed off to provide

  271 Southbay Dr Unit 153, Naples, FL 34108
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  /32

  $3,100,000 Sold Mar 25, 2025

  9790 Gulf Shore Dr Unit 106, Naples, FL 34108

  • 3 Beds
  • 2.5 Baths
  • 2,285 Sq Ft
  • Built 1994

  Last Sold Summary

  • 8% Below List Price
  • $1,357/SF
  • 196 Days On Market

  Current Estimated Value $2,837,079

  Last Listing Agent Vito Bauer Coldwell Banker Realty

  9790 Gulf Shore Dr Unit 106, Naples, FL 34108
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  /43

  Est $6,983,560 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,400 Sq Ft

  11125 Gulf Shore Dr Unit PH-3, Naples, FL 34108

  11125 Gulf Shore Dr Unit PH-3, Naples, FL 34108
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  /50

  $3,799,000

  • 4 Beds
  • 4.5 Baths
  • 3,737 Sq Ft

  375 Conners Ave, Naples, FL 34108

  It is said buyers make a decision to buy a home almost instantly. Call it curb appeal- From the moment you arrive at this stunning gulf access pool home in Vanderbilt, you will want to see more! You can't help but notice the attentive pride the owner has invested in this home. As you enter, the love and care here will instantly become apparent to the most discerning buyer. From the custom

  Steven Leek Sterling Realty of SWFL

  375 Conners Ave, Naples, FL 34108
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  /22

  $15,000 per month

  • 2 Beds
  • 2 Baths
  • 1,562 Sq Ft
  • Condo for Rent

  10851 Gulf Shore Dr Unit 402, Naples, FL 34108

  Gorgeous 2-bedroom 2 bath beach front unit available for season 2027! This home has been totally renovated and boasts an amazing gourmet kitchen with all new appliances and beautiful furnishings. This gated community features eight acres of tropical surroundings with private walkway leading directly to the beach. Vanderbilt Gulfside features a 40 x 60 swimming pool, BBQ grill and fitness center.

  Monica Simon William Raveis Real Estate

  10851 Gulf Shore Dr Unit 402, Naples, FL 34108
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  /33

  $1,300,000 Sold Feb 04, 2025

  400 Flagship Dr Unit 808, Naples, FL 34108

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 2000

  Last Sold Summary

  • 7% Below List Price
  • $750/SF
  • 138 Days On Market

  Current Estimated Value $1,211,417

  Last Listing Agent Lesley Garlock William Raveis Real Estate

  400 Flagship Dr Unit 808, Naples, FL 34108
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  /35

  Est $4,558,772 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 3,568 Sq Ft

  337 Trade Winds Ave, Naples, FL 34108

  337 Trade Winds Ave, Naples, FL 34108
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  /11

  $7,995,000

  • 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
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  /20

  $4,072 per month

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

  260 Southbay Dr Unit ID1226371P, Naples, FL 34108

  Indulge in the ultimate coastal living experience with this stunning one-bedroom condo, ideally located just off Vanderbilt Beach Road in North Naples. This unit is on the second floor and there is an elevator for your convenience. Feel at home with the convenience of having a plethora of exceptional restaurants, including the renowned Gumbo Limbo at The Ritz, within walking distance. Moreover,

  260 Southbay Dr Unit ID1226371P, Naples, FL 34108
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  /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

  Last Listing Agent Ashley Silvers William Raveis Real Estate

  279 Heron Ave, Naples, FL 34108
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  /7

  Est $1,690,685 Not Listed For Sale

  406 Seabee Ave, Naples, FL 34108

  406 Seabee Ave, Naples, FL 34108
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  /35

  $2,385,000

  • 3 Beds
  • 2 Baths
  • 1,767 Sq Ft

  373 Egret Ave, Naples, FL 34108

  THE CLOSEST THING TO NEW CONSTRUCTION- A BRAND NEW REMODEL JUST FINISHED! BRING YOUR BOAT AND COME ENJOY PARADISE! THIS IS WHOLE NEW HOME! NEW KITCHEN, NEW BATHROOMS, BRAND NEW Professionally decorated/brand NEW furniture. ALL NEW LANDSCAPING. This TURNKEY FURNISHED classy ranch style POOL HOME WITH DOCK AND LIFT is your perfect Naples hideaway. 3 bedrooms plus a den/Florida room, 2 baths, and

  Tim Ryan Equity Realty

  373 Egret Ave, Naples, FL 34108
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  /46

  $20,000 per month

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

  10475 Gulf Shore Dr Unit 115, Naples, FL 34108

  RARELY AVAILABLE– TOTALLY REMODELED BEACH FRONT CONDO – 3 BEDROOM – POOLSIDE CABANA – GARAGE - BOAT DOCK W/ LIFT - TURNKEY - END UNIT. Minimum of Two weeks is required. Designer-renovated and impeccably maintained, this stunning 3-bedroom beachfront condo is a rare lease opportunity on Vanderbilt Beach. An end unit with multiple balconies and direct beach views, it has been completely redesigned

  David Roy Downing Frye Realty Inc.

  10475 Gulf Shore Dr Unit 115, Naples, FL 34108
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  /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 $3,999,839

  Last Listing Agent Lorena Nunez Premiere Plus Realty Company

  9715 Gulf Shore Dr Unit 702, Naples, FL 34108
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  /45

  Est $2,080,388 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,254 Sq Ft

  9207 Vanderbilt Dr Unit 3, Naples, FL 34108

  9207 Vanderbilt Dr Unit 3, Naples, FL 34108
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  /37

  $1,375,000

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  400 Flagship Dr Unit 401, Naples, FL 34108

  Welcome to unit 401 at the Regatta, where coastal elegance meets everyday ease. This turnkey, waterfront condominium is just steps to Vanderbilt Beach with fantastic views of the world renowned Ritz Carlton Beach Resort. Income producing with bookings in place for the upcoming season will offset your expenses while providing a gorgeous canvas for many fond memories to come at your Neapolitan

  Amanda Erwin John R Wood Properties

  400 Flagship Dr Unit 401, Naples, FL 34108
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  /20

  $4,072 per month

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

  260 Southbay Dr Unit ID1226374P, Naples, FL 34108

  Indulge in the ultimate coastal living experience with this stunning one-bedroom condo, ideally located just off Vanderbilt Beach Road in North Naples. This unit is on the second floor and offers self check-in. Revel in the convenience of having a plethora of exceptional restaurants, including the renowned Gumbo Limbo at The Ritz, within walking distance. Moreover, you're only a two-minute stroll

  260 Southbay Dr Unit ID1226374P, Naples, FL 34108
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  /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

  Last Listing Agent Tony Grech Compass Florida LLC

  10682 Gulf Shore Dr Unit 302, Naples, FL 34108
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  /42

  Est $3,137,443 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,250 Sq Ft

  10620 Gulf Shore Dr Unit 401, Naples, FL 34108

  10620 Gulf Shore Dr Unit 401, Naples, FL 34108
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  /44

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 1,490 Sq Ft

  10684 Gulf Shore Dr Unit 106, Naples, FL 34108

  Direct Vanderbilt Bay Condo Frontage! Experience effortless beach-to-bay living in this freshly painted, three-bedroom, first-floor residence at the highly sought-after gated community of Monte Carlo Club Naples, complete with the rare convenience of assigned boat slip #14. Thoughtfully designed, this end unit condominium features an expanded living area created by enclosing the former lanai,

  Jana Caudill eXp Realty LLC

  10684 Gulf Shore Dr Unit 106, Naples, FL 34108
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  /38

  $30,000 per month

  • 5 Beds
  • 4.5 Baths
  • 4,815 Sq Ft
  • House for Rent

  403 Seabee Ave, Naples, FL 34108

  An exceptional, one-of-a-kind luxury elevator-equipped three-story retreat with Gulf-access and complete with a private dock able to accommodate a large vessel. This estate sits perfectly positioned on one of Conners’ widest canals (approximately 200 feet across), offering the waterfront lifestyle you’ve always dreamed of. Designed to impress, this architectural masterpiece showcases breathtaking

  Nikki Dimitrova Florida Prime Realty, LLC

  403 Seabee Ave, Naples, FL 34108
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  /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

  Last Listing Agent Ryan Schwartz Naples Homes

  10562 Gulf Shore Dr Unit 402, Naples, FL 34108
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  /41

  Est $1,904,152 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  9380 Gulf Shore Dr Unit 401, Naples, FL 34108

  9380 Gulf Shore Dr Unit 401, Naples, FL 34108
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  /44

  $4,595,000 Pending

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

  239 Channel Dr, Naples, FL 34108

  A rare gem in Naples, this 5-bedroom, 4 full-Bath / 1 half-bath estate offers the best of both worlds: Direct Gulf Boat Access with a 27,000-pound COVERED BOAT LIFT right out your back door & exclusive Vanderbilt Beach PRIVATE BEACH ACCESS just across Gulf Shore Drive. Nestled in an exclusive enclave of only three peninsula streets that uniquely combine direct beach and boat access, opportunities

  Shawn Stuben Shawn Stuben Naples Properties

  239 Channel Dr, Naples, FL 34108
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  /20

  $32,784 per month

  • 5 Beds
  • 4.5 Baths
  • 3,465 Sq Ft
  • Condo for Rent

  494 Seagull Ave Unit FL1-ID1296214P, Naples, FL 34108

  Experience waterfront luxury and feel at home in this stunning Naples home in Conners at Vanderbilt Beach. This property features soaring ceilings, a gourmet kitchen, a heated pool with spillover spa, and expansive balconies with sweeping canal views. With 3,500 square feet, this home accommodates up to 12 guests.This beautifully appointed waterfront home offers elegant indoor spaces and a

  494 Seagull Ave Unit FL1-ID1296214P, Naples, FL 34108
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  /50

  $1,800,000 Sold Dec 10, 2025

  380 Conners Ave, Naples, FL 34108

  • 4 Beds
  • 3 Baths
  • 2,164 Sq Ft
  • Built 1977

  Last Sold Summary

  • 22% Below List Price
  • $832/SF
  • 234 Days On Market

  Last Listing Agent Cheena Chandra Premier Sotheby's Int'l Realty

  380 Conners Ave, Naples, FL 34108
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  /45

  Est $1,081,501 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,482 Sq Ft

  9380 Gulf Shore Dr Unit 103, Naples, FL 34108

  9380 Gulf Shore Dr Unit 103, Naples, FL 34108

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