Old Naples Real Estate
Gulf-front estates, renovated cottages, and luxury condos on tree-lined streets, steps from Fifth Avenue South, Third Street South, and the Naples Pier.
The Old Naples Guide
Old Naples is the historic, walkable heart of Naples, Florida, set along the Gulf of Mexico west of U.S. 41. It is home to Fifth Avenue South, Third Street South, and the Naples Pier, and offers Gulf-front estates, renovated and new custom homes, historic cottages, and luxury condos, with Aqualane Shores and Port Royal just to the south.
Few places in Florida combine a white-sand Gulf beach, a historic downtown, and quiet residential streets within a few blocks. That rare mix of walkability and coastal character makes Old Naples one of the most sought-after and land-constrained neighborhoods in Southwest Florida.
Jeremy O’Guinn, Broker Associate and Certified Negotiation Expert with Downing-Frye Realty, helps buyers and sellers navigate Old Naples, where lot value, elevation, and street location shape pricing.
What It Is Like to Live in Old Naples
Village charm, the Gulf, and everything within walking distance
Daily life in Old Naples happens on foot, by bike, or by golf cart. Morning walks on the beach, coffee on Third Street South, dinner on Fifth Avenue South, and sunsets at the Naples Pier are part of the routine.
- Fifth Avenue South and Third Street South shopping, dining, and galleries
- The Naples Pier and miles of Gulf beach
- Cambier Park, the Norris Center, and community events
- Tree-lined avenues with a mix of historic and new homes
Old Naples Homes and Condos for Sale
From Gulf-front estates to downtown condos
Gulf-Front Estates
Rare beachfront homes along Gordon Drive and Gulf Shore Boulevard South, among the most valuable properties in Florida.
Custom Homes and Cottages
New custom homes and renovated residences beside historic cottages, many of which are purchased for land value.
Luxury Condos and Townhomes
Lock-and-leave living steps from Fifth Avenue South and Third Street South, from boutique buildings to townhomes.
Old Naples Destinations Within Walking Distance
The places residents reach on foot or by golf cart
Fifth Avenue South
Naples’ signature street of restaurants, shops, and galleries.
Third Street South
Boutiques, cafes, and the Saturday farmers market.
The Naples Pier
A landmark for sunsets, fishing, and dolphin sightings.
Gulf Beaches
Public beach access at the ends of many avenues.
Cambier Park
Concerts, tennis, playgrounds, and community events.
Naples Bay
Marinas, waterfront dining, and boating nearby.
Old Naples vs. Aqualane Shores vs. Port Royal
Naples’ premier coastal neighborhoods
Old Naples, Aqualane Shores, and Port Royal sit side by side and represent the pinnacle of Naples real estate. The main differences are walkability and boating access.
Old Naples
The highest walkability and strongest village character, with Gulf-front estates and condos, but limited deep-water boating.
Aqualane Shores
Deep-water canal homes with Gulf access, still within reach of Fifth Avenue South.
Port Royal
Naples’ most exclusive estates on Gulf, bay, and deep-water canal lots, with premier boating.
What to Know Before Buying in Old Naples
Land, elevation, and location within the neighborhood
Review these before going under contract:
Flood Zone and Elevation
Elevation, FEMA zone, and construction era shape insurance and future building requirements.
Lot Size and Location
Distance to the beach, Fifth Avenue South, and Third Street South drives value block by block.
Renovate or Rebuild
Compare renovation costs against land value and new construction potential.
City of Naples Rules
Confirm setbacks, height limits, and permitting with the City of Naples.
Condo Building Health
For condos, review milestone inspections, reserve studies, and planned assessments.
Recent Comparable Sales
Old Naples pricing varies by street and lot, so rely on the closest recent sales.
Selling a Home in Old Naples
Pricing that reflects the land, the location, and the home
Old Naples buyers include end users, builders, and investors, each valuing a property differently. Accurate pricing starts with lot value, street location, and the most relevant recent sales.
Explore Old Naples Further
Listings, selling, and market data
A Note From Jeremy
Broker Associate · Certified Negotiation Expert · Downing-Frye Realty
“In Old Naples, a block can change value meaningfully, and the land often matters as much as the house. I help buyers and sellers understand lot value, elevation, and the right comparable sales, so every decision is grounded in what a property is really worth.”
Old Naples, Florida: FAQ
Location, homes, walkability, and value
Where is Old Naples located?
Old Naples is the historic heart of Naples along the Gulf of Mexico, west of U.S. 41 and centered on Fifth Avenue South, Third Street South, and the Naples Pier. Aqualane Shores and Port Royal lie just to the south.
Is Old Naples walkable?
Yes. Old Naples is the most walkable luxury neighborhood in Naples, with Fifth Avenue South, Third Street South, the Naples Pier, Cambier Park, and the beach all within walking or golf cart distance for many homes.
What types of homes are in Old Naples?
Old Naples offers Gulf-front estates, renovated and new custom homes on tree-lined streets, historic cottages often valued for their land, and luxury condominiums and townhomes near Fifth Avenue South and Third Street South.
Is Old Naples near the beach?
Yes. The neighborhood borders the Gulf, with public beach access at the ends of many avenues and the Naples Pier at 12th Avenue South.
How does Old Naples compare to Aqualane Shores and Port Royal?
Old Naples offers the highest walkability and strongest village character but limited deepwater boating. Aqualane Shores adds deep-water canal homes within reach of Fifth Avenue South, and Port Royal offers the most exclusive Gulf and bay estates with premier boating.
Why are some Old Naples homes priced mainly for land value?
Lots in Old Naples are scarce and close to the Gulf, so older homes are often purchased for the land and replaced with new construction. Lot size, location, and elevation can matter more than the existing house.
How can I track pricing in Old Naples?
The Old Naples Market Insider shows active listings, pending sales, and homes and condos sold in the past six months, updated automatically from the MLS.
Explore More Ways to Search
Guides to help you compare Naples coastal neighborhoods.
Find Your Old Naples Home
Whether you want a Gulf-front estate, a cottage near Third Street South, or a lock-and-leave condo, a short conversation is the best place to start.
The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.