Oyster Bay Homes with Canal Access Waterfront

Oyster Bay Homes with Canal Access Waterfront

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida, within Collier County. This enchanting community offers a unique blend of coastal charm and modern living, making it the perfect destination for those seeking a serene waterfront lifestyle.

Oyster Bay is renowned for its beautiful homes with canal access, providing residents with the opportunity to embrace the best of Florida's outdoor living. Imagine stepping out of your backyard and onto your private dock, ready to embark on a day of fishing, boating, or simply soaking up the sun. The stunning waterways weave through this picturesque neighborhood, creating a tranquil atmosphere that is hard to resist.

The homes in Oyster Bay are thoughtfully designed, featuring spacious layouts, modern amenities, and breathtaking views of the lush landscapes and shimmering canals. Whether you’re looking for a cozy retreat or a luxurious estate, this community has something to suit every taste and lifestyle. The seamless blend of indoor and outdoor living spaces invites you to enjoy the warm Florida sunshine year-round.

Beyond the beauty of the homes, Oyster Bay is conveniently located near Naples' vibrant downtown area, where you can explore charming boutiques, exquisite dining options, and pristine beaches. The community is also close to top-rated schools, golf courses, and recreational parks, making it an ideal choice for families and active individuals alike.

Discover the allure of Oyster Bay and experience the ultimate waterfront living in one of Florida’s most coveted locations. Your dream home awaits!

Newest Oyster Bay Homes with Canal Access Waterfront

3 Beds ⋅ 3 Baths ⋅ 226018001 MLS

Discover an exceptional waterfront retreat in the highly desirable location of Oyster Bay. This unique property offers a total of 160 feet of water frontage, 80 ft on the southern side and 80 feet on the northern side with two private boat docks, two lifts and bridge free access to Naples Bay and Gordon Pass- ideal for avid boaters and adventure seekers. This coastal charmer offers a perfect blend of timeless style, updated interior and open living spaces perfect for entertaining. Stunning water views and endless sunrises and sunsets with preferred southern exposure. This home has been meticulously maintained throughout the years making it an ideal full time/part time residence or an incredible opportunity for redevelopment. Enjoy close proximity to Downtown Naples, world class dining, shopping and beaches.

1420 Jewel Box Avenue, Naples

3 Beds ⋅ 4 Baths ⋅ 226013587 MLS

Premier waterfront residence at 1510 Chesapeake Ave with direct, no bridge boating access to Naples Bay and the Gulf via Gordon Pass. Set along one of the widest and most navigable canals in Oyster Bay and Royal Harbor, this custom built concrete block home offers a true boater’s lifestyle with distinctive lighthouse inspired architecture and a striking presence. A large double entrance circular driveway and herringbone brick paver entry create a strong first impression. Inside, the home offers three bedrooms plus a den, three and a half baths, soaring ceilings, custom millwork, hand applied trompe l’oeil detail, and abundant natural light that showcases every inch of the interior. The den can easily function as a fourth bedroom. The primary suite and one guest bedroom open directly to the pool, while the additional guest room and den each feature covered outdoor sitting areas, creating a seamless connection to the waterfront setting. From there, the home flows naturally to the dock and spa, extending the living experience outdoors. The custom Ipe hardwood dock, widely regarded as the gold standard in waterfront decking, offers exceptional durability, low maintenance, timeless aesthetic appeal, and a premium gateway to the Gulf. The large garage includes an oversized storage closet, ideal for organizing fishing tackle, rods, boating gear, and other coastal lifestyle essentials. Never flooded and ideally located just minutes from Tin City, Bayfront, Cabana on the Bay, and Downtown Fifth Avenue, this property combines architectural character, premier canal frontage, and exceptional access by both land and water.

1510 Chesapeake Avenue, Naples

3 Beds ⋅ 2 Baths ⋅ 226013181 MLS

Completely renovated 3 bedroom, 2 bath, TURNKEY furnished BY ARHAUS, waterfront condo on Naples Bay with Direct Gulf access & 26 ft Boat Slip, NEW ROOF JULY 2026. The interior has been COMPLETELY RENOVATED and NEVER LIVED-IN with luxury finishes and elegant Arhaus furnishings throughout creating a stylish and functional living space including impact windows and doors. Second floor end unit with additional windows flood the home with natural light and stunning bay views. Outdoor living is elevated with a lanai overlooking the water perfect for enjoying spectacular sunsets from this tranquil setting. This boutique community consists of only 6 residences with low Condo Fees, offering a private exclusive atmosphere minutes to 5th Avenue, 3rd Street, the city's world class shopping, dining, arts and white sandy beaches.

1390 Chesapeake Avenue Unit 1390, Naples

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Gina "Jenna" Billman

Growing up in a small town in central Illinois, I was raised with the simple Midwestern values that still guide me today: be honest, work hard, do what you say you'll do, help others when you can, and always thank God for His blessings. Loyalty has always been important to me — I’m proud to say I’m still happily married to my high school sweetheart. In 1985, we made the move to Southwest Florida, where we raised our children, built our business, and made this beautiful community our home. I know the area well and truly enjoy helping others put down roots here too. Buying or selling a home is one of life’s biggest decisions. You need someone you can trust — someone who understands the process from beginning to end and will be a true advocate for your best interests. My job is to help you achieve the best possible price, terms, and conditions. Whether you're looking for your dream home or trying to find the right buyer, your goals are my priority. I hold a Bachelor's Degree from Eastern Illinois University. I’m also a member of the National Association of Realtors (NAR), Florida Association of Realtors, and the Royal Palm Coast Realtor® Association. I enjoy being busy enough to be successful earning top producer awards, but never so busy that I can’t take a personal interest in every client I serve. Let’s work together to make your real estate journey smooth, successful, and rewarding.

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Lisa A. Sawyer

Full-time real estate professional since 1996. Top producing award winner with the experience to service your real estate needs. Specializing in residential, investment, rehab, commercial, and waterfront properties. My goal is to provide outstanding client service tailored to individual customer needs. With a focus on honesty and integrity, I provide exceptionally high-quality service and valuable insight into the real estate market. Exceptional service will guarantee that clients have a highly positive and satisfactory experience that exceeds their personal and financial objectives. Customer service that will encourage them to refer me to their friends and family. 27+ Years of sales and marketing expertise Bachelor’s degree in Marketing Relocation Specialist Excellent Communication Skills Superior Real Estate Knowledge Over a decade of personal experience in home renovation, home construction, and investment property procurement.

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