Three property types on one bay, and three different ways to price.
Oyster Bay holds low-rise condominiums, two villa communities and a limited number of single-family homes, all sharing the same bridge-free run to the Gulf through Gordon Pass. A $450,000 condominium, a $1.8 million villa and an $11 million bayfront house are valued by entirely different measures, and the first question in any Oyster Bay valuation is which of the three you own.
What Drives Value: Waterfront Homes
| Gulf Access | The bridge-free route down Naples Bay to Gordon Pass is the reason a boating buyer is here, and anything that limits it is the first thing a buyer’s captain will check |
| Bay or Canal | Bay frontage has set the top of the market: the highest sale of the last two years was a bayfront home at $11.45 million, against $3.58 million to $4.5 million for canal homes |
| Dock and Lift | Permitted dock dimensions, lift capacity, depth at low tide and the width of the canal behind the property set the vessel a buyer can keep |
| Seawall | Age, height and condition, with documentation of any repair, cap or replacement |
| Age of House | New homes are being offered at $7.8 million to $8.9 million, older homes at $3.1 million to $5.8 million; which side of that line your house sits on decides who the buyer is |
| Elevation | Finished floor elevation, flood zone, insurance and claims history, and any elevation or hardening work, with certificates to support it |
What Drives Value: Condominiums and Villas
| The Building | Buyers compare within a building before they compare across Oyster Bay, and closed sales in your own association are the first comparables |
| Position | A bay-facing unit, an upper floor or an open canal view prices above an interior or ground-floor unit in the same building |
| Size | Most units are two bedrooms of about 900 to 1,400 square feet; the larger residences at Sea Eagle, on Chesapeake Avenue and on Curlew Avenue have sold at the top of the range, up to $1.4 million |
| Boat Slip | A deeded or assigned slip that conveys with the unit, and the length and beam it takes, is the clearest premium a condominium here can carry |
| Reserves | Milestone inspection and reserve study status where they apply, reserve funding, and recent or pending assessments, which buyers and their attorneys review before they tour |
| Condition | Impact glass, updated kitchens and baths, and flood elevation for ground-floor units |
| Rules | Minimum lease terms, the number of leases allowed each year and pet policy, each of which widens or narrows the pool of buyers |
Request a Confidential Valuation
Tell us about your Oyster Bay condominium, villa or home and we will prepare a private, advisor-reviewed valuation built from the sales that genuinely compare to it, not an automated estimate. Complimentary and without obligation, whether or not you decide to sell. See how we prepare a valuation, our approach to selling a waterfront home and selling a condominium, and, where discretion matters, a private, off-market sale.
Oyster Bay - Recent Sales
What Sold, and How
Thirty-one Oyster Bay properties closed between September 1, 2024 and September 24, 2026, counting the Oyster Bay addresses that listing agents file under Royal Harbor in the MLS. By property type, they show three markets that move at different speeds and negotiate differently.
| Property Type | Sales · Price Range | Median Days · Vs. Original |
|---|---|---|
| Condominiums | 22 · $300,000 to $1.4M | 109 · 88% |
| Villas and townhomes | 4 · $1.57M to $2.05M | 104 · 84% |
| Single-family homes Four houses; one bayfront home sold twice |
5 · $3.58M to $11.45M | 111 · 76% |
Condominiums gave up the least in negotiation, about 12% from their original asking price, and villas a little more. Single-family homes gave up the most, about 24%: with only four houses trading in two years there is rarely a clean comparable, and a price set without one tends to come down. The full sales record, building by building, is on our Oyster Bay guide.
What the Market Looks Like Now
Oyster Bay’s condominium market has turned toward buyers. Fifteen units closed in the twelve months to September 24, 2026, and thirteen were for sale that day, about ten months of supply spread evenly from $325,900 to $1.225 million. The median sale over those twelve months was $500,000, against $570,000 in the twelve months before, and almost half of the units for sale had been listed for more than six months. In a market like this, the first price is the one that matters: the units that sold over the last twelve months did so at a median of 98 days, while the ones still waiting are competing with close to a year of supply.
Single-family homes are a thinner market still. Six were for sale on September 24, 2026, against two closings in the previous twelve months. New construction is being offered at $7.8 million to $8.9 million without a closed sale at that level yet, one older home expired and came back $300,000 lower, another has been reduced from $4.349 million to $3.899 million, and a 2002 home that sold for $4.5 million in May 2025 is back on the market at $5.8 million. For villas, one Bayview Estates villa was offered at $2.35 million, and four other attached homes came off the market unsold between late May and September, at asking prices from $1.679 million to $2.495 million, so a villa seller is pricing against asking prices that did not hold.
Naples market reports, updated monthly: closed sales, median prices, months of supply and price per square foot for every Naples waterfront neighborhood in the Naples Waterfront Market Report, with the month’s highlights in our September 2026 waterfront roundup.
By neighborhood: Aqualane Shores · Bay Colony · Coquina Sands · Isles of Capri · Kalea Bay · The Moorings · Naples Cay · Olde Naples · Oyster Bay · Park Shore · Pelican Bay · Port of the Islands · Port Royal · Royal Harbor · The Dunes · Vanderbilt Beach
Pricing an Oyster Bay Condominium
We start with closed sales in your building, adjust for floor, view, size and finish, then test the result against the buildings around it. A bay-facing unit does not price off an interior one, and a renovated unit does not price off an original one down the hall. Since Florida’s condominium safety laws were rewritten after 2021, buildings of three stories or more must complete milestone inspections and structural integrity reserve studies, and a building that has done both and funded its reserves sells at a visible premium to one that has not. If your building is under three stories, say so plainly and show the reserves anyway, because buyers will ask.
Pricing an Oyster Bay Villa or Home
Villas price from the two communities that hold them: Bayview Estates, on the bay, sold at $1.8 million and $2.05 million, and Villa Ensenada, on Clam Court, at $1.565 million and $1.625 million. Homes are priced from the water first, bay or canal, frontage, depth and what the dock is permitted to hold, then from the house. Because Oyster Bay sits beside Royal Harbor on the same water, we test every home price against Royal Harbor sales as well, since a boating buyer shops both neighborhoods in the same afternoon. Our Royal Harbor selling guide covers that side of the market.
Selling an Older Home
Several Oyster Bay houses date from the 1970s and 1980s, and new homes are now being offered at about twice what existing canal homes have sold for. If yours is an original house, your buyer may be a builder or a family planning to rebuild as easily as someone who wants to move in, and the property should be marketed to both, with the survey, seawall history, dock permits and elevation certificate ready before it goes to market.
What Buyers Will Ask For
In a condominium or villa: the milestone inspection report and reserve study where they apply, the budget, recent and pending assessments, the insurance policy, the leasing and pet rules, and written confirmation of any boat slip that conveys with the unit. Buyers and their attorneys review these before making an offer, so assembling them before listing keeps a contract from stalling.
In a waterfront home: a current survey, the seawall history, dock and lift permits with dimensions, the elevation certificate, flood zone and insurance and claims history, plus documentation of any post-storm repair or elevation work.
When to List in Oyster Bay
The Naples season runs January through April and peaks in February, when most sellers list at once. With close to a year of condominium supply already on the market, listing in the fall puts a unit in front of the season’s first buyers instead of into the February crowd, and leaves time for photography, any cosmetic work and the association documents a buyer will ask for on day one. For a waterfront home, it also leaves time to finish dock or seawall work before a buyer is standing on the seawall with you.
Explore Oyster Bay
Nearby Waterfront Neighborhoods
Selling in Oyster Bay Questions
What is my Oyster Bay property worth?
It depends first on which of the three markets you are in. Between September 2024 and September 2026, Oyster Bay condominiums sold for $300,000 to $1.4 million at a median of about $398 per square foot, villas and townhomes for $1.57 million to $2.05 million, and single-family homes for $3.58 million to $11.45 million. Within each, the building, the water and the condition set the price. Request a confidential valuation and we will prepare one from the sales that genuinely compare.
How long does it take to sell a condo in Oyster Bay?
Condominiums that sold in the twelve months to September 24, 2026 took a median of 98 days, and almost half of the units for sale that day had been listed for more than six months. With about ten months of supply, the units that sell are the ones priced from the building’s own closed sales from the first day.
Are Oyster Bay condo prices falling?
The median condominium sale fell from $570,000 in the twelve months to September 2025 to $500,000 in the twelve months to September 2026, and the median price per square foot from about $466 to $368. Part of that is a shift toward smaller units in the older buildings, but buyers have more leverage than they did a year ago. Units priced from their building’s own sales still close well, at a median of about 92% of their original asking price.
Should I sell my Oyster Bay home as a residence or to a builder?
It depends on the house and the water. New homes are now being offered here at $7.8 million to $8.9 million, while existing canal homes have sold for $3.58 million to $4.5 million, so an original house on good water will draw builders and buyers planning to rebuild as well as buyers who want to live in it. We model both and market to both.
How does selling in Oyster Bay compare with Royal Harbor?
The two sit side by side with the same bridge-free route to Gordon Pass, and buyers shop them together. Royal Harbor is larger and mostly single-family, with far more comparable home sales; Oyster Bay is mostly condominiums and villas. We price an Oyster Bay home against both neighborhoods, because a buyer will.
How does Alpizar & Company market an Oyster Bay property?
We price from the sales that truly compare, in the building first for a condominium, assemble the association and dock documents buyers now ask for before listing, present the property with photography and film directed in-house, and preview it privately to our buyer registry and the brokers who work the Naples Bay boating market before it launches publicly. Call (239) 438-1102.
Sales figures are compiled from Naples Area Board of Realtors MLS data for residential properties on Oyster Bay’s streets, whether filed under the Oyster Bay or the Royal Harbor development, closed September 1, 2024 through September 24, 2026, and properties offered, withdrawn or taken off the market as of September 24, 2026; deemed reliable but not guaranteed. Valuations are opinions of value based on comparable sales and are not appraisals. Condominium inspection and reserve requirements, association rules, dock rights and flood zones change; confirm current details with the association or the applicable agency.
Meet the Team
Connect with Real Estate Advisors... not Salespeople.
Alpizar & Company is a family-owned independent brokerage specializing in luxury waterfront real estate across Naples' most sought-after neighborhoods. Led by Robert Alpizar (CLHMS, GRI, SRS, PSA) and Marlene Alpizar, our team operates as advisors — not salespeople — guiding buyers and sellers with firsthand local expertise and no corporate quotas.
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