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Grey Oaks
Intelligence

One gate, ten sections, 903 residences: 779 single-family homes and detached villas from the 1993 estate plats to the Estuary, 124 condos and coach homes, and 39 lots still waiting for a house. Every number below comes from the community’s own recorded deeds, the Collier County tax roll, and MLS living areas; deeds recorded through 2026-08-12, built 2026-09-03.

Residences behind the gate
903
779 single-family, 124 condos and coach homes, 39 lots
Qualified sales since 1993
2,135
The community’s entire deed record
Single-family $/sqft, 2026
$1,088
Doubled in 2022, held every year since
Condo $/sqft today
$714
13% off the 2023 top, 84% above 2021
Sales in 2025
44
One in twenty homes changes hands a year
Titles held in a trust
44%
And 44% of buyers since 2023 bought that way

Data powered by Modern Signal Advisory

1. What has Grey Oaks traded for, by year?

Median sold price per square foot by year closed: recorded deed prices over MLS living area, all floors, for qualified, arm’s-length sales of improved homes. Hover any point for the figure and the number of sales behind it.

Single-family, 1997 to 2026

779 homes across nine sections, n=1,179 improved sales with a matched MLS living area
What this means. Verdict: the single-family market never left its surge. Median price per square foot went from $625 in 2021 to $1,021 in 2022 and has held above $1,000 every year since, reaching $1,088 through June 2026 on 23 sales with a matched living area. What a real reversal looks like here is the 2007 to 2012 stretch, when per-foot pricing fell from $517 to $367, and the last four years do not resemble it.
Leverage. Per-foot pricing has been flat near the top for four straight years ($1,021, $1,048, $1,042, $1,064) while the homes that clear have skewed newer, as the chart below shows. If you own here, the market is paying for size and finish, not for a rising rate per foot, so a renovated or larger house has a different case than an original one, and the line supports pricing at the plateau, not above it.

Condos and coach homes, 2012 to 2026

124 residences in Traditions, Terra Verde, and L’Ermitage, n=154 improved sales with a matched living area; earlier years too thin to chart
What this means. Verdict: the attached side has come off its peak while the houses have not. Condo price per square foot topped out at $821 in 2023 and has printed $768, $724 and $714 in the years since, while the single-family line beside it reached $1,088 through June 2026. With five condo sales recorded so far in 2026 (three with a matched living area) and eight in 2025, each closing moves the median a long way, so the direction is the signal and the decimal is not.
Leverage. Condos peaked at $821 per square foot in 2023 and sit at $714 so far in 2026. If you own a unit and are anchoring on a neighbor’s 2023 number, that gap is the entire conversation; if you are buying in, a thin market with a recorded easing is where the negotiation lives, and three matched sales this year is not a queue.

Newer homes vs the original stock, 2012 to 2026

Homes built 2005 or later (Torino and Miramonte, Traditions, the later Estuary streets, estate-plat rebuilds) vs the 1993 to 2004 originals; eight or more sales on each side every year, n on hover
What this means. Verdict: the premium for a newer house is now on the record, and it has widened every year since 2023. For a decade the two lines traded places, the newer plan-product homes clearing below the 1993 to 2004 originals per foot through most of 2013 to 2018 because the originals sat on the bigger lots; the surge repriced both to about $1,000 a foot in 2022, and since then the newer stock has pulled ahead, $1,092 and $1,095 in 2024 and 2025 against $1,006 and $1,052, and $1,228 against $1,018 through June 2026, a 21 percent premium on eleven sales at a $6.4M median. True builder exits are rarer still, five sales in eight years at $939 to $1,029 a foot in 2019 and 2020 and $1,699 in 2025; they are receipts, not a line.
Leverage. If you are building new behind this gate, the gap between the two lines is what the market pays for the newer house, measured in the record rather than asserted. If you are buying, the original stock at $1,000 to $1,050 a foot is the community’s entry, and the lot under it is what the next buyer will be paying for.

2. How often does Grey Oaks actually trade?

How often Grey Oaks actually trades, what is on the market inside the gate right now, and why one community carries ten different price points.

Qualified sales per year

Full community, by segment, 1994 to 2026 (2026 through June, pending the county’s qualification coding)
What this means. Verdict: the number of homes selling each year has settled into a low, steady band. The sellout ran to 109 single-family sales in 2001 and the bust cleared 98 in 2013; since 2022 the single-family side trades 34 to 42 times a year, with 24 recorded through June 2026, and the condos 5 to 17. New-construction closings ended in 2017 and 39 lots remain, which is what a built-out community looks like on the deed record: about one home in twenty changing hands each year.
Leverage. Annual sales have roughly halved from the 2013 peak of 98 to the 34 to 42 range of the last four years. If you are selling, fewer sales means fewer rivals on the same weekend and a thinner set of recent closings for a buyer to argue from; if you are buying, in a 903-door community trading around 44 times a year, the right house shows up on its schedule, not yours.

The market right now

Single-family listings inside the gate by month, September 2024 to August 2026: median asking price and homes on the market
What this means. Verdict: supply has drained and what is left has been sitting. Active single-family listings inside the gate peaked at 28 in February and March 2026, after nine new listings arrived in January alone, and are down to 13 in August with nothing new listed since June. The median ask has settled to $4.25M, about $1,166 a foot, against $1,064 a foot on the homes that actually closed since September 2024 and a sold-to-ask of 0.94, so the remaining shelf is asking above what has been clearing.
Leverage. 13 homes on the market in August 2026 and nothing new listed since June. If you are listing this fall, the competition set is a dozen homes that have been sitting, not the thirty of last spring; if you are buying, the roughly six percent gap between asking and closing is recorded, and the homes still on the shelf have been there a while.

Ten sections behind one gate

Median county just value by section, TaxYear 2025 roll (assessed, not market; the ladder is the point, not the level)
What this means. Verdict: Grey Oaks is not one price. The roll runs from Terra Verde and Avila near $1.5M to $1.9M, through Traditions, Torino and Miramonte, Capistrano, Venezia and Isla Vista in the $2M to $4M band, to the Estuary at $4.5M and the estate plats at $4.9M, where the 1993 originals and the 2025 completions share the same streets.
Leverage. If you own here, price against your section’s ladder, not the community line; a Torino home and an Estuary home are different markets under one name. If you are buying, the same gate, membership and address come at four very different entry points.

The new-vintage premium and the equity floor

Single-family sales since 2022 by the age of the house that traded, and what long-tenure owners paid vs what the county says today
Built 2015 or later, sold since 2022
$1,158
Per foot, n=14, median 4,160 sqft at $4.25M
Every older vintage, sold since 2022
$1,006 to $1,045
Per foot, n=151; the premium for new is 11 to 15 percent
Homes built since 2015
86
18 of them since 2020; 39 lots still open
Pre-2020 single-family basis
$1.46M
Median paid by 511 owners, vs $3.82M assessed today
Pre-2020 condo basis
$745K
Median paid by 67 owners, vs $1.64M assessed today
Single-family held 15+ years
28%
Median tenure 10.9 years; one in five held 20+
What this means. Verdict: land is the majority of what changes hands here, and nobody holding it is forced. The county assigns 58.6 percent of single-family value to land, with a median land assessment of about $2.24M per parcel, and 39 vacant lots remain against 819 homes; 86 homes have been built since 2015 and 18 since 2020, so replacement happens one house at a time rather than in waves. The 511 owners who bought before 2020 paid a median $1.46M for homes the county now values at $3.82M, about 40 cents on today’s assessed dollar, and the market pays a measured premium for a new house, $1,158 a foot for homes built since 2015 against $1,006 to $1,045 for every older vintage, not a doubled one.
Leverage. Land carries 58.6 percent of assessed value and only 39 lots are left. If you own a dated house, the dirt is most of what a buyer is paying for and the alternative sites are nearly gone, which is the rebuild arithmetic; if you are building, the lot, the membership and the house you actually want are the reason, with the per-foot premium as the receipt. If you are buying, the seller across the table is not distressed; win on certainty and terms.

Where does your home sit in this?

The record above is the community; your home, or the one you are building, is a specific case on a specific line of it. Thirty minutes puts the two together.

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3. Who owns Grey Oaks, and for how long?

All 943 residential parcels, classified from the certified tax roll by owner structure, residence, and tenure. A primary-home community that is quietly moving into trusts.

Ownership structure

Individual vs trust vs entity share, by segment
What this means. Verdict: the homes changing hands are going to the same kind of owner who left them. Trusts hold 43.2 percent of the single-family stock today and took 44.4 percent of the 171 purchases from 2023 to 2026, individuals hold 49.3 percent and bought 48.5 percent, and LLCs are 7.4 percent against 7.0 percent; the condos run 46 percent trust with almost no entity ownership. The buyer replacing the seller looks like the seller, which is why the character of the streets has held through the price run.
Leverage. Recent buyers mirror existing owners almost line for line (trust 44.4 percent versus 43.2, LLC 7.0 versus 7.4). If you are selling and wondering who moves in behind you, that is a stability argument the record shows rather than asserts; if you are buying, you are buying from families and their estate plans, not funds, and the trustee’s timeline is the one to read.

Who actually lives here

Homestead, absentee, and out-of-state share, by segment
What this means. Verdict: this is a lived-in community rather than a second-home block. 65.2 percent of single-family homes carry a homestead exemption (the owner’s primary Florida residence) and four in five owners take their tax mail in Florida, with 20.8 percent absentee (mail sent somewhere other than the property) and 15.5 percent mailed out of state; the condos match on homestead with a slightly larger absentee group at 26.6 percent. The out-of-state ownership that does exist is spread thin across the Midwest and Northeast, led by Illinois at 17 owners and Massachusetts at 16, with Ontario the largest single feeder.
Leverage. 15.5 percent of single-family owners take mail in another state, and no single state holds more than 17 homes. If you are selling, the likely buyer already lives in Naples or has decided to, so relocation and estate stories carry more weight here than second-home pitches; if you are buying, you are joining neighbors who live here year-round, and the community trades on their calendar.
IL 17 owners
MA 16
NY 15
OH 13
PA 12
CT 10
MI 10
Canada 26

Tenure curve

Years since last arm’s-length purchase, dated residences by segment
What this means. Verdict: the typical owner here has been in place about a decade and is sitting on a large paper gain. Median time since the last arm’s-length purchase (a normal open-market sale, not a family or trust transfer) is 10.9 years across 764 dated single-family homes: 156 bought in the last five years, 207 in the five before that, and 217 held fifteen years or more, 152 of them past twenty, back to the sellout era. The 511 owners who bought before 2020 paid a median $1.46M for homes the county now values at a median $3.82M; the condo side turns faster, with a median hold under eight years.
Leverage. 511 pre-2020 owners paid a median $1.46M against a $3.82M county value today, and one in five has held past twenty years. If you own here, that gain sits on the public record and is room to be flexible on terms, most valuable when it is not needed; if you are buying, tomorrow’s supply comes from those legacy holds through estates and life changes, not from a builder, and the best future inventory is not listed yet.

4. When does Grey Oaks sell, and who buys?

When Grey Oaks actually closes, and who has been on the buying side of the deed, era by era.

When the community closes

Closings by month of recorded deed, all 2,135 qualified sales 1992 to 2026
What this means. Verdict: this market records its deals in the spring. Across the full deed record, May is the heaviest month at 251 closings, followed by March at 245 and April at 240, while August is the lightest at 116, and February through May carries 43 percent of the year. Contracts signed in the winter land on the county record in those spring months, which is when a buyer here has the most company.
Leverage. 251 deeds recorded in May across the record versus 116 in August, more than double. If you are selling, the launch window that meets the most buyers opens around the holidays, not in spring, because spring closings trace back to winter contracts; if you are buying, late summer and fall are when the thin market is thinnest, and when patience negotiates best.

Who has been buying

Buyer profile on qualified deeds, by era
What this means. Verdict: the buyer at the closing table has changed shape. Trusts took 44.4 percent of the 171 qualified purchases from 2023 to 2026 (qualified meaning an ordinary open-market sale the county counts as a real transaction, not a transfer between family members or into a trust), up from 13.9 percent in the 2000 to 2009 era, and out-of-state buyers are back to 34.1 percent after sitting near 20 percent through the 2010s and 2020 to 2022. Estate-planned and relocating money is setting the price now, not local move-up demand.
Leverage. 44.4 percent of buyers since 2023 took title in a trust and only 48.5 percent as individuals. If you are selling, the person buying next door is structuring for a hold, not shopping a bargain, and one in three now arrives from out of state; if you are buying, you are competing with households that move on season timelines and close in spring, so being ready in December beats bidding in April.

Grey Oaks, on the record

Questions about the record

What this study is, where the numbers come from, and how to read them against your own residence.

What is Grey Oaks Intelligence?

A deed-record study of one gate, ten sections and 903 residences: 779 single-family homes and detached villas from the 1993 estate plats to the Estuary, 124 condos and coach homes, and 39 lots still waiting for a house. It reads the community’s own recorded deeds, the Collier County tax roll and MLS living areas in four parts: the market per foot, velocity and the shelf across the ten sections, who owns Grey Oaks, and season and the buyer. It is built from the full record, 2,135 qualified sales since 1993, with deeds recorded through 2026-08-12 and built 2026-09-03.

Where does the data come from, and which parts of Grey Oaks does it cover?

Collier County Property Appraiser tax roll and recorded deed records, public record, qualified arm’s-length sales only, with price per square foot computed on MLS living areas. The market-right-now chart uses listing records from RentCast, matched to the community by address. The community covers the recorded Grey Oaks plats, the Estuary at Grey Oaks, Avila, Capistrano, Isla Vista, Venezia, Torino and Miramonte, Traditions, Terra Verde and L’Ermitage. Recent months are partial pending the county’s qualification coding. It is informational, not an appraisal.

What does Grey Oaks sell for per square foot?

The single-family market never left its surge. Median price per square foot went from $625 in 2021 to $1,021 in 2022 and has held above $1,000 every year since, reaching $1,088 through June 2026 on 23 sales with a matched living area. A real reversal here looked like 2007 to 2012, when per-foot pricing fell from $517 to $367, and the last four years do not resemble it. The attached side is different: condo price per square foot topped out at $821 in 2023 and has printed $768, $724 and $714 since, with each closing moving the median a long way on five to eight sales a year, so the direction is the signal and the decimal is not.

Does a newer house in Grey Oaks command a premium?

Now it does, and the premium has widened every year since 2023. For a decade the two lines traded places, because the 1993 to 2004 originals sat on the bigger lots; the surge repriced both to about $1,000 a foot in 2022, and since then the newer stock has pulled ahead: $1,092 and $1,095 in 2024 and 2025 against $1,006 and $1,052, and $1,228 against $1,018 through June 2026, a 21 percent premium on eleven sales at a $6.4M median. Homes built since 2015 clear $1,158 a foot against $1,006 to $1,045 for every older vintage: a measured premium, not a doubled one. True builder exits are rarer still, five sales in eight years; they are receipts, not a line.

How many Grey Oaks homes sell in a year, and what is on the market now?

About one home in twenty changes hands each year. The sellout ran to 109 single-family sales in 2001 and the bust cleared 98 in 2013; since 2022 the single-family side trades 34 to 42 times a year, with 24 recorded through June 2026, and the condos 5 to 17. New-construction closings ended in 2017 and 39 lots remain. The shelf has drained and what is left has been sitting: active single-family listings inside the gate peaked at 28 in February and March 2026 and are down to 13 in August with nothing new listed since June, asking a median $4.25M, about $1,166 a foot, against $1,064 a foot on the homes that actually closed since September 2024 and a sold-to-ask of 0.94.

Is Grey Oaks one price?

No. The roll runs from Terra Verde and Avila near $1.5M to $1.9M, through Traditions, Torino and Miramonte, Capistrano, Venezia and Isla Vista in the $2M to $4M band, to the Estuary at $4.5M and the estate plats at $4.9M, where the 1993 originals and the 2025 completions share the same streets. Land is the majority of what changes hands: the county assigns 58.6 percent of single-family value to land, with a median land assessment of about $2.24M per parcel. The 511 owners who bought before 2020 paid a median $1.46M for homes the county now values at $3.82M, about 40 cents on today’s assessed dollar, and nobody holding that is forced.

Who owns Grey Oaks, and when does it sell?

The buyer replacing the seller looks like the seller. Trusts hold 43.2 percent of the single-family stock and took 44.4 percent of the 171 purchases from 2023 to 2026, individuals hold 49.3 percent and bought 48.5 percent, and LLCs are 7.4 percent against 7.0. It is a lived-in community: 65.2 percent of single-family homes carry a homestead exemption, four in five owners take their tax mail in Florida, and the out-of-state ownership is spread thin across the Midwest and Northeast, led by Illinois at 17 owners and Massachusetts at 16. The typical owner has been in place about eleven years. Deals record in the spring: May is the heaviest month at 251 closings, with February through May carrying 43 percent of the year, and out-of-state buyers are back to 34.1 percent of recent purchases.

What happens when I book a private consult?

A conversation with us about your Grey Oaks position against this record: where your section and vintage sit on the per-foot curve, what the shelf is asking against what has cleared, and whether the moment is now or a season from now, as an owner, a buyer, or an owner building new inside the gate. There is no obligation. Use the Book a private consult button below to pick a time.

Talk to the Knox Brothers

Sellers get a pricing read against the community’s own deed record. Buyers, and owners building new, get the openings the record shows.

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The Knox Brothers · Compass · Naples, Florida
Sources: Collier County Property Appraiser tax roll and recorded deed records (public record; deeds recorded through 2026-08-12, recent months partial pending the county’s qualification coding), with price-per-square-foot figures computed on MLS living areas; the market-right-now chart uses listing records from RentCast, matched to the community by address. Qualified, arm’s-length sales only. The community covers the recorded Grey Oaks plats, the Estuary at Grey Oaks, Avila, Capistrano, Isla Vista, Venezia, Torino and Miramonte, Traditions, Terra Verde, and L’Ermitage. Informational only, not an appraisal.
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