Oyster Bay condominium sales more than doubled this year, while its homes and villas barely traded.
We pull the Oyster Bay numbers every month and publish them here in full: inventory, months of supply, price per square foot, what closed and what came off the market unsold, split between the condominiums and the homes and villas, which trade as two different markets. For the neighborhood and its bridge-free boating, see our guide to Oyster Bay.
September 2026 — Inventory
| Segment | Listings | Supply |
|---|---|---|
| Homes & villas | 5 active 1 under contract |
30.0 months |
| Condominiums | 15 active 1 under contract |
11.2 months |
| All Oyster Bay | 20 active 2 under contract |
13.3 months |
Months of supply compares the residences offered today with the pace of sales over the last twelve months. At about thirteen months, Oyster Bay favors buyers, and most of that comes from the top of the market: five homes and villas are for sale, from $2,350,000 to $7,995,000, against two sales in a year. The condominiums carry about eleven months.
Twelve-Month Performance
| Segment | Sales | Per Sq Ft |
|---|---|---|
| Homes & villas | 2 · $2.60M Prior year: 5 · $2.05M |
$1,034 · 89% Prior year: $979 · 79% |
| Condominiums | 16 · $483K Prior year: 7 · $570K |
$365 · 92% Prior year: $466 · 86% |
| All Oyster Bay | 18 · $515K Prior year: 12 · $822K |
$371 · 92% Prior year: $504 · 83% |
Eighteen residences closed in the twelve months to September 30, 2026 for $14.3 million, against 12 for $25.7 million the year before, when the $11,450,000 sale of 1340 Jewel Box Avenue carried almost half the volume. Condominium sales more than doubled, 16 against 7, and sellers gave up less: the median condominium closed at 92% of its original asking price after 90 days on the market, against 86% and 182 days. Condominium price per square foot fell to $365 from $466, partly because this year’s sales were smaller units, a median 1,213 square feet against 1,392; one Blue Point residence sold twice, for $335,000 in December and $590,000 in August. Only two homes or villas sold: 1506 Jewel Box Avenue for $3,580,000 in June and a Villa Ensenada townhome for $1,625,000 in March. The percentage beside each price per square foot is the closing price against the original asking price.
Inventory as of October 1, 2026. Sales, medians, price per square foot, days on market and percentage of asking price reflect the 18 sales closed between October 1, 2025 and September 30, 2026, against the 12 closed in the twelve months before. One sale recorded in the MLS after closing is included in the prices and excluded from price per square foot and days on market. Source: Naples Area Board of REALTORS® MLS.
What Changed in September
No sale closed in September, against one in September 2025, the $11,450,000 sale of 1340 Jewel Box Avenue. The month’s movement:
| Under contract | 1225 Sandpiper Street, a home offered at $989,000, and a Chesapeake Landings condominium offered at $325,900 |
| New listings | 1085 Sandpiper Street, newly built, at $7,995,000; 1095 Sandpiper Street at $3,295,000; and a Clam Court condominium at $295,000 |
| Back on the market | 1420 Jewel Box Avenue, at $3,095,000 after its listing at $3,395,000 expired, and an Azzurro condominium at $1,225,000 after its listing at $1,250,000 expired |
| Left unsold | 1100 Sandpiper Street, terminated at $7,777,000 after 320 days, and a Clam Court condominium withdrawn at $399,900 |
With three homes newly listed or relisted and one terminated, the top of the market turned over in a single month while two contracts were signed.
The Gap Between Asking and Achieved
Median asking price per square foot for the residences offered on October 1, 2026, against the median buyers paid over the last twelve months:
| Segment | Asking | Paid |
|---|---|---|
| Homes & villas | $1,273 23% above paid |
$1,034 two sales |
| Condominiums | $471 29% above paid |
$365 last 12 months |
Both groups are listed well above what buyers have paid. The homes and villas figure rests on two sales, so read it lightly. Part of the condominium gap is size: the condominiums offered today are smaller, a median 1,080 square feet, and smaller units ask more per foot. Even so, the condominiums that sold this year closed at 96% of their final asking price, which means the gap closed through price reductions before the sale, not at the closing table.
The Listings That Did Not Sell
Twenty-six residences came off the market unsold over the last twelve months and have not returned, against 18 sales: eighteen condominiums, five homes and three villas and townhomes. The median one had been on the market about six months.
When Oyster Bay Actually Trades
Closings by month over the last year: 2 in November, 2 in December, 2 in February, 2 in March, 1 in April, 3 in May, 2 in June, 3 in July and 1 in August, with none in October, January or September. Oyster Bay closed later than the season: half of the 18 sales closed between May and August.
How We Group Oyster Bay
These groupings are ours. Homes & villas: the single-family homes on Jewel Box Avenue, Sandpiper Street and Chesapeake Avenue, with the Bayview Estates and Villa Ensenada villas and townhomes. Condominiums: the low-rise associations, among them Four Winds, Blue Point, Cherrystone Court, Clam Court, Escondido Marina, Granada, Azzurro and the Chesapeake buildings. Listing agents file some Oyster Bay condominiums and villas in the MLS under Royal Harbor or under the association’s own name; we include them here by association and street. Single-family homes filed under Royal Harbor are counted in our Royal Harbor market report, so no sale appears in both. The neighborhood and its bridge-free route to the Gulf are covered in our Oyster Bay guide.
What This Means If You Are Selling
Price against what closed in your own group. With about eleven months of condominium supply and thirty of homes and villas, buyers here can wait, and the condominiums that sold reached 96% of their final asking price only after the reductions. A residence priced at the recent sales from the first day, with its dock and bridge-free route to the Gulf described accurately, is the one that sells. We prepare a confidential valuation from the sales that genuinely compare to your residence; see selling in Oyster Bay.
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Oyster Bay Market Questions
Is Oyster Bay a buyer’s or a seller’s market?
A buyer’s market at the moment. With 20 residences for sale against 18 sales over the last twelve months, Oyster Bay carries about thirteen months of supply: about eleven for the condominiums and thirty for the homes and villas, where two sold in the year.
What is the median price in Oyster Bay?
Across the 18 sales closed between October 1, 2025 and September 30, 2026, the median was $515,000. Condominiums sold for a median $482,500, from $300,000 to $1,399,000. The two homes and villas were 1506 Jewel Box Avenue at $3,580,000 and a Villa Ensenada townhome at $1,625,000.
Is Oyster Bay waterfront?
Yes. Oyster Bay sits on the east side of Naples Bay beside Royal Harbor, and its canals run bridge-free to the bay and south through Gordon Pass to the Gulf of Mexico. Most residences that sold over the last year were recorded in the MLS with Gulf access, many with a deeded or included boat slip.
Why are some Oyster Bay sales filed under Royal Harbor?
Listing agents choose the development name in the MLS, and some Oyster Bay condominiums and villas are filed under neighboring Royal Harbor or under their association’s own name. We assign those sales to Oyster Bay by association and street. Single-family homes filed under Royal Harbor are counted in our Royal Harbor report, so no sale is counted twice.
How often is this report updated?
On the first of every month, with the month just closed. This edition covers closed sales through September 30, 2026 and inventory as of October 1, 2026, from the Naples Area Board of REALTORS® MLS.
Can I get figures for a specific building or for prior months?
Yes. We hold the full sales history for every Oyster Bay association and street and can prepare a report for any of them, including months earlier than this edition. Call (239) 438-1102 and tell us what you need.
Data source: Naples Area Board of REALTORS® MLS data for Oyster Bay. Inventory as of October 1, 2026; closed-sale figures cover October 1, 2025 through September 30, 2026, compared with October 1, 2024 through September 30, 2025. Oyster Bay condominiums and villas filed in the MLS under Royal Harbor or under their association’s name are included. Segment definitions are our own and are set out above. Market data is deemed reliable but not guaranteed and is not a valuation of any individual property.
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