The Best Streets to Live on in Old Naples: A Local’s Guide

Old Naples is where beach life and village life blend into one dreamy, walkable neighborhood with sunsets at the Pier, cappuccinos on Third Street South, concerts at Cambier Park, and a slow, palm-fringed drive home. When buyers ask me, “What are the best streets?” the real answer is lifestyle: toes-in-the-sand beachfront, quiet canopy lanes, or a chic walk-to-everything address. Below is my curated guide, honed from years of helping clients find “the one” in Old Naples.

The Big Picture: How to Think About Old Naples

• Beachfront trophy zone: Gulf Shore Blvd S (north) flowing into Gordon Drive (south). These are the iconic, low-inventory addresses with front-row sunsets and exceptional land value. These are the last homes the sun will touch before it sinks into the Gulf every night. 

• West ("sand side") of Third Street South: Romantic, tree-canopy avenues with quick beach paths. This is quiet, timeless, and deeply “Old Naples.”

• Walk-to-5th Avenue South & Cambier Park: Peaceful streets that still put dining, galleries, tennis, and the park’s music nights within an easy stroll.

• Historic/Third Street South pocket: Near the Pier and Palm Cottage. This area is layered with charm, café culture, and that effortless, vacation-every-day feel.

My Short List (and why they’re special)

Beachfront & First-Tier West of the Beach

• Gulf Shore Blvd S (north Old Naples)
  Low-density beachfront, postcard views, and the ultimate “open the door and hear the waves” lifestyle.

• Gordon Drive (7th Ave S–14th Ave S corridor)
  Blue-chip pedigree, estate-scale lots, and private beach paths. This is privacy with presence.

West (beach side) of Third Street South (quiet + close to the sand)

• 1st & 2nd Ave N (west of 3rd) – Leafy canopy, refined but relaxed, minutes to the sand.

• 3rd & 4th Ave N (west of 3rd) – That sweet spot for serenity + access; consistent streetscape and strong long-term value.

• 1st & 2nd Ave S (west of 3rd) – “Flip-flops to the beach” energy; intimate scale and pure Old Naples romance.

• 8th Ave S (west of 3rd) – Pier-adjacent without the bustle; classic cottages mingle with tasteful new builds.

• 12th–13th Ave S (west of 3rd) – Steps to Third Street cafés and boutiques; lush landscaping and authentic charm.

Walk-to-Everything “Goldilocks” (quiet, but close)

• 4th & 5th St S (between 5th Ave S & 13th Ave S) – Peaceful residential rhythm and an easy glide to both Third Street and the beach.

• 7th & 8th St S (near Cambier Park) – Tennis, concerts, farmers market—“park life” meets beach access.

• 6th & 7th Ave S (east of 3rd to 8th St) – Elegant infill, alley access for discreet garages, and a civilized stroll to the Pier or 5th Ave S.

Classic Charm Pockets

• Broad Ave S (west segment) – Understated beauty with quick beach paths and a timeless streetscape.

• Palm Cottage / 12th Ave S area – Storybook curb appeal and café culture right outside your door.

Pros & Things to Consider (because details matter)

What buyers love

• Mature tree canopy and picturesque streetscapes

• Multiple beach access points + real walkability

• Alley access (clean front elevations, discreet garages)

• Exceptional land value and historically strong demand

What to watch

• Seasonal foot traffic near the Pier and big event nights on 5th Ave S/Cambier

• Micro-differences in lot width, elevation, and flood zone by block

• Build-envelope constraints if you plan to renovate or redevelop

My process includes flood-zone and elevation checks, build-envelope reviews, and a resale lens so your purchase is lifestyle-perfect and future-proof.

How to Choose Your Street (the 2-question test)

1. Beach vibe or village vibe?
   Do you want to stroll out for sunsets first, or dinner and live music first?

2. How quiet should it feel?
   Absolute serenity, or a lively, convenient walk-to-everything address?

Your answers point us directly to the right micro-pockets and even the right side of the street.

Concierge Next Steps (what I’ll do for you)

• Custom Street Shortlist: Active + whisper/off-market opportunities on your target blocks

• 5-Minute Walk-Shed Maps: Beach paths, dining, parks, and morning coffee routes

• Lot & Elevation Notes: Flood, setbacks, redevelopment potential, and likely insurance considerations

• Vibe Tour: Coffee on Third, a Pier walk, then a slow roll down the west-of-Third avenues to compare shade, privacy, and sound

Final Word

There isn’t one “best” street. There’s the street that best fits your Naples life. That’s where the magic (and the long-term value) happens.

Ready to find your perfect street in Old Naples?

I’d love to be your guide. Call/text Melinda Gunther | Premier Sotheby’s International Realty at 239-297-2155, or DM me on Instagram @Naples.Agent to start your bespoke search.

Start here with homes for sale in Old Naples today: 

Equal Housing Opportunity. All street recommendations are lifestyle-based; buyers should verify measurements, flood zones, and permitting with appropriate professionals.