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Buying or selling? Call (904) 351-6461
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Cottages At Winding Creek in St. Augustine

Cottages At Winding Creek
Homes for Sale in St. Augustine, FL

Community in St. Augustine · St. Johns County · ZIP 32086
Median sale $280K
Free · No obligation
Talk to a Cottages At Winding Creek Expert

True comps, carrying-cost math, and listings before the portals.

Live Market Pulse
15/100
Market Heat
Cooler than normal
2013 → 2026 · 82 at the 2022 peak
0 is Cottages At Winding Creek's coldest market since 2013, 100 its hottest. Today: 15. How it's scored
Built fromLive realMLS data17 years of closingsUpdated twice daily
Live · Cottages At Winding Creek Housing Pulse realMLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Price
$280K ▼
Median sold · 12 mo
down 11.1% vs the prior 12 months
-11.1% ▼
1-yr price change
n = 7 and 6 sales in the two windows
$185/sf
Sold $/sqft · 12 mo
peak $202 in 2024
94.6%
Sale vs ask
Tempo
1.5mo
Supply
3 to 6 months is the balanced band
104days
Median DOM · closed
14 days at the 2022 low
0%
Under contract
St. Johns: 34% (1,005 of 2,926)
1 · 0
For sale · pending
live counts, refreshed twice daily
7
Sold · last 12 mo
10-yr average: about 7 a year
Ownership and context
40%
Cash buyers · Cottages At Winding Creek
2 of 5 sales, 12 mo ending July 2025
Track record · 17 years of records
0
Failed listings · 2025
peaked at 16 in 2010
1,407sqft
Median sold home size
12-mo windows, closed sales
Jon Brooks, founder of Momentum Realty
Jon's Current Read

This is a thin market by any measure: seven closings in the trailing window and a single active listing today, so any one sale carries outsized weight on the numbers. The median price sits at $280,000, or $184.79 per square foot, and that figure is down 11.1% year over year — a move that reflects the small sample as much as it reflects demand. With so few transactions to average, condition and finish differences on any given unit can swing the median more than the broader St. Johns County market would.

Momentum's posture on this one is patient and precise. With months of supply at 1.5 and only one home actively listed, inventory is genuinely tight, which is why the market reads as seller-leaning even against a falling median. The median 104-day time on market tells a different story on the demand side, though — it took real pricing discipline to get the last several sales closed, so sellers should not assume a fast, effortless close just because supply is scarce, and buyers who are patient and well-prepared have real room to negotiate on terms.

Cottages At Winding Creek Housing Pulse · Momentum Research · as of July 14, 2026

Cottages At Winding Creek right now

🟡 Balanced market. 1.5 months of supply and 0% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of realMLS records, as of July 14, 2026. Confidence: Medium (1 active and pending listings, 7 closed sales in 12 months).

🔴 Off the recent peak. The trailing-12-month median ($280K) is down 11.1% from the prior 12 months ($315K). With about 7 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level realMLS closed sales, 12-month windows ending July 14. Confidence: Medium (7 and 6 sales in the two windows).

Jump to: Price history & scorecard · Homes for sale · Schools · FAQ

Updated July 14, 2026 · Live data: realMLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness

The 60-Second Overview

Cottages At Winding Creek market snapshot (as of July 14, 2026): the median sale price is about $280K ($185 per sq ft over the trailing 12 months of closed sales), a median 104 days on market for closed sales, and 1.5 months of supply, a balanced market. The trailing-12-month median is down 11% from the prior 12 months, computed from record-level realMLS closed sales (7 closings in the current window).

Cottages At Winding Creek is a gated community in St. Augustine, St. Johns County, built around a shared clubhouse, pool, tennis courts, and playground rather than large private lot amenities — the kind of trade-off that keeps maintenance simpler but ties buyers to HOA-run common areas.

Quick Match

Who Cottages At Winding Creek is best for.

Best for

  • Buyers who want low-maintenance ownership and are comfortable with grounds, pool, and clubhouse access handled through an HOA.
  • Buyers targeting a purchase near the $280,000 median who can move decisively once a rare listing appears.
  • Buyers prioritizing gated access and on-site recreation (pool, tennis, playground) over a large private lot.

Probably not for

  • Buyers who need to choose from multiple active listings right now — there is only one on the market.
  • Buyers unwilling to accept HOA dues and rules in exchange for maintained common areas and security features.
  • Sellers expecting a quick, no-negotiation close — the 104-day median time on market argues against that assumption.
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Market Pulse

How Cottages at Winding Creek is performing right now

59/100
momentum
Balanced Market (limited data)
Seller's marketBalancedBuyer's market
1.7Months of supplytight
190Median days on marketdays
1 : 1Under contract vs for salestrong demand
7Sold in last 12 monthsliquidity
-4%Asking vs recent sold $/sqftroom to negotiate

Tight supply and strong demand favor sellers here. Homes still take about two months to sell, though, and with asking prices running above recent sales per square foot, a prepared buyer has room on anything overpriced. Reading each home against the real comps, not the headline trend, is where the edge is.

Live from realMLS, as of June 25, 2026. Refreshed twice daily. Months of supply, days on market, and the contract-to-listing ratio are computed from current Cottages at Winding Creek listings and the trailing twelve months of closed sales.

8.6A- score
Momentum intelligence
Momentum buy score

Our proprietary read on how a home in Cottages at Winding Creek buys, holds, and resells. See the five factors.

Homes For Sale Right Now in Cottages at Winding Creek

Live MLS inventory for Cottages at Winding Creek. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.

215 Bayberry Circle #605 home for sale in Cottages at Winding CreekActive · 190 daysTop listing
$299,000
3 bd · 2 ba · 1,680 sqft · built 2007
215 Bayberry Circle #605, St. Augustine, 32086
RenovatedBest value
Listed by FLORIDA HOMES REALTY & MTG LLC
175 Bayberry Circle #1005 home for sale in Cottages at Winding CreekPending · 100 days
$305,900
3 bd · 2 ba · 1,680 sqft · built 2007
175 Bayberry Circle #1005, St. Augustine, 32086
Listed by WATSON REALTY CORP

Active and pending Cottages at Winding Creek listings as of 2026-06-25, priced high to low. Source: Data provided by realMLS.. Tap any home to ask about it.

Interactive Map

Cottages at Winding Creek on the map.

Every active, pending, and recently sold home, plotted. Toggle the layers, color the dots by status or lot type, and tap a home for the details.

Listing locations from realMLS; lot type inferred from listing descriptions. Destination pins are approximate. Map data © OpenStreetMap, tiles © CARTO. Flood, school, and commute overlays are on the roadmap.

Nearby & Commute

How far is everything?

The takeaway

The location is the everyday-convenience case: shopping, schools, and the major roads are all a manageable drive.

Drive times from Cottages at Winding Creek. They are approximate and vary with traffic and your exact start point.

Historic downtown St. Augustine~10 to 15 min · the nation's oldest city
Interstate 95~8 to 12 min · north to Jacksonville, south to Daytona
St. Augustine Beach / Anastasia Island~12 to 18 min · the Atlantic
US-1 corridor shopping~5 to 10 min · everyday retail
St. Johns County Town Center area~15 to 25 min · north
Jacksonville / St. Johns Town Center~40 to 50 min · north via I-95
Jacksonville International Airport (JAX)~55 to 65 min · north

Distances and drive times are approximate and vary with traffic. Confirm your real commute at your real departure time.

Nearby Communities

Explore more neighborhoods near Cottages at Winding Creek Homes for Sale in St with Momentum Realty’s local guides.

Enclave at Treaty Oaks Homes for Sale in StEnclave at Treaty Oaks Homes for Sale in StSt. Augustine, FL · 0.9 miSummer Bay at Grand Oaks Homes for Sale in StSummer Bay at Grand Oaks Homes for Sale in StSt. Augustine, FL · 1.4 miCordera Townhomes in StCordera Townhomes in StSt. Augustine, FL · 1.6 miSawmill Landing Homes for Sale in StSawmill Landing Homes for Sale in StSt. Augustine, FL · 1.9 miSeasons at Morada Homes for Sale in StSeasons at Morada Homes for Sale in StSt. Augustine, FL · 1.9 miEntrada Homes for Sale in Saint Augustine, FLEntrada Homes for Sale in Saint Augustine, FLSaint Augustine, FL · 2.2 miOakbrook Homes for Sale in StOakbrook Homes for Sale in StSt. Augustine, FL · 2.3 miBrookestone Homes for Sale in StBrookestone Homes for Sale in StSt. Augustine, FL · 2.4 miStStSt. Augustine, FL · 2.5 mi

Browse all Florida neighborhood guides →

Carrying cost · the no-CDD edge

No CDD bond means thousands less per year than newer master plans.

Typical CDD community~$2,500/yr
Cottages at Winding Creek (no CDD)$0/yr

Roughly $25,000 saved over 10 years in carrying cost, before resale.

Illustrative. NE Florida CDD assessments commonly run $1,500-$3,500+/yr and vary by community; verify per property.

Schools

15-Second Take
  • St. Johns County Public Schools
  • Verify the zoned schools by address
  • Magnet and choice options may be available
  • Confirm current ratings before relying on them
  • Private and parochial options nearby

Cottages at Winding Creek is served by St. Johns County Public Schools. Assignment is by address and can change, so confirm the exact zoned elementary, middle, and high schools for any specific home, plus any magnet or choice options. Treat published ratings as a starting point, not the full story.

Buying with schools in mind? We can confirm the exact zoned schools for any Cottages at Winding Creek address.

The takeaway

What actually shapes value at Cottages at Winding Creek, sourced and dated. We do not publish rumor.

Recent Developments in Cottages at Winding Creek

Development Intelligence

Our read on what is being built around Cottages at Winding Creek, scored for direction, significance, and how close the effect lands. The full sourced timeline follows below.

Net OutlookBullishSt. Augustine is a high-demand, school-driven market, so the story for an established community like Cottages at Winding Creek is attainable value, the school district, and condition rather than new construction.

Attainable value in a top school district

BullishNotable impact
SignificanceRadius: Cottages at Winding Creek

Attainable cottage-style homes with recent listings around $300,000 to $320,000 in the top-rated St. Johns County school district are a durable value that tends to support demand; confirm conditions for the specific home (neighborhoods.com, 2026).

Low-maintenance cottage stock

NeutralMinor impact
SignificanceRadius: Cottages at Winding Creek

Midsize cottage-style homes from the late 2000s are a manageable product, but roof, systems, and updates still drive value; inspect and comp house by house.

Flood and insurance verification

NeutralNotable impact
SignificanceRadius: St. Augustine

St. Johns County parcels can carry flood exposure that varies lot to lot; the FEMA map is authoritative per parcel, so pull it and an insurance quote during diligence.

Direction, significance, and effect-radius ratings are Momentum's proprietary, qualitative read of the sourced items below, not investment advice or a prediction for any specific home.

Development, infrastructure, retail, and school activity affecting Cottages at Winding Creek, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated June 2026.

Showing the latest, scroll for all updates ↓

  1. 2026
    Market

    Cottages at Winding Creek listings around $300K to $320K

    Recent listings in Cottages at Winding Creek ran roughly $300,000 to $320,000, on cottage-style homes from about 1,470 to 1,680 square feet built roughly 2007 to 2010. Why it matters: These are illustrative third-party figures, not MLS statistics; condition and updates drive the number, so comp each house on its own. Source

  2. 2024
    Taxes

    St. Johns County millage

    St. Johns County millage applies (St. Johns County Property Appraiser, 2024). The HOA dues are separate from the tax bill; confirm whether any CDD applies for a community of this vintage. Why it matters: Confirm the exact taxing authorities and the bill for the specific parcel, and read the HOA dues separately. Source

Development alerts for Cottages at Winding CreekGet a short monthly email when something new is approved, funded, or opens near Cottages at Winding Creek.

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By submitting, you agree that EAB RE INVESTMENTS LLC (Momentum Realty) and its agents may call, email, and text you about your inquiry, which may involve automated means and prerecorded or artificial voices. You do not need to consent as a condition of buying any property, goods, or services. To opt out, reply STOP at any time or reply HELP for assistance. You can also click the unsubscribe link in emails. Message and data rates may apply. Message frequency may vary. See our Privacy Policy and SMS Terms.

Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.

The Strategy

The Cottages at Winding Creek buying strategy.

If we were buying in Cottages at Winding Creek, this is the order of operations we would run, and the one we run for our clients.

1

Read the HOA dues and what they cover. Pull the current dues, what they fund, and any reserve or special-assessment items before you write.

2

Inspect the late-2000s systems. Confirm the roof, HVAC, and any updates on a home of this vintage, since condition drives value.

3

Comp house by house. Price the specific home against the closest comparable Cottages at Winding Creek sale, not a community average.

4

Pull the FEMA flood zone and an insurance quote. Confirm the determination for the exact parcel.

5

Confirm the zoned St. Johns County schools. Verify the current assignment by address, since school zoning drives demand here.

The Quick Decision
Best Buy
A well-kept, updated cottage on a good lot, priced to its condition, with the HOA and flood zone verified.
Biggest Risk
Deferred maintenance on a late-2000s home, or an HOA cost or restriction you have not read.
Best Lot
The lot and the home's condition are the value here; confirm what the HOA maintains.
Smart Timing
A school-driven, high-demand market gives a prepared buyer who has inspected the home and read the HOA the best position.
Deep-Dive Intelligence

The full read, only if you want it.

The takeaway

On mobile, tap any heading below to open it. This is the home by home, lot by lot, club and renovation detail, organized so you can jump straight to what matters to you.

Community Details at a Glance

Cottages at Winding Creek is an established single-family community in St. Augustine, St. Johns County, ZIP 32086, built roughly 2007 to 2010, with attainable, midsize cottage-style homes reported from roughly 1,470 to 1,680 square feet (Watson Realty; neighborhoods.com, 2026). Recent listings have run roughly $300,000 to $320,000 (neighborhoods.com, 2026, illustrative, not MLS), an attainable point for the top-rated St. Johns County school district. St. Augustine offers quick access to historic downtown, I-95, and the beaches, and the community carries a homeowners association, so the central diligence items are the HOA dues and coverage, the home's systems, and the FEMA flood zone per parcel.

Cottages at Winding Creek Homes For Sale

What your money buys in Cottages at Winding Creek.

The takeaway

Three honest price bands. Condition and lot, not the square footage alone, decide where a home lands.

Here are the broad resale bands in Cottages at Winding Creek today. The right home is the one matched to your budget and the renovation math, so seeing fitting listings early is the edge.

Entry: homes needing updates
$245K to $280K

Cottage-style homes in more original condition are the value entry, near the lower end of recent listings; budget the updates and confirm the roof and systems before you write (neighborhoods.com, 2026, illustrative, not MLS).

Lowest entry
Mid: updated three-bedroom cottages
$280K to $285K

Updated cottage-style homes around the recent listing range of $300,000 to $320,000 are the core of the market. Condition and lot separate these; price on the closest comparable sale.

Most inventory
High: larger or fully renovated homes
$285K to $290K

Larger homes toward the top of the size range, or fully renovated cottages, sit at the top. Price each on its size, updates, and lot rather than a community average.

Strongest resale

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

See Off-Market & Private Listings
What Your Money Buys

What ~$280K buys here.

Three realistic price bands. Where a home lands comes down to condition and lot, not square footage alone.

$245K to $280K
Entry: homes needing updates
Cottage-style homes in more original condition are the value entry, near the lower end of recent listings; budget the updates and confirm the roof and systems before you write (neighborhoods.com, 2026, illustrative, not MLS).
$280K to $285K
Mid: updated three-bedroom cottages
Updated cottage-style homes around the recent listing range of $300,000 to $320,000 are the core of the market. Condition and lot separate these; price on the closest comparable sale.
$285K to $290K
High: larger or fully renovated homes
Larger homes toward the top of the size range, or fully renovated cottages, sit at the top. Price each on its size, updates, and lot rather than a community average.

Approximate 2026 resale bands from third-party listing data and public records, not NEFAR statistics. Confirm pricing for a specific home.

Operator Intelligence

Renovation & Resale Intelligence

The factors that actually move value in Cottages at Winding Creek, condition, lot, and the renovation math, read from current listings and recent sales.

15-Second Take
  • Renovation math decides the deal
  • Better lots and views resell strongest
  • Roof and HVAC age drive the insurance quote
  • Interior lots are where buyers overpay
Proprietary Data

The renovation premium.

Renovated-listing inventory in Cottages at Winding Creek is too thin right now to compute a reliable renovation premium. We read condition home by home against real comps before you offer.

Unit Value

The unit premium.

In a condo the value the market gives back at resale is set by the unit, not a lot: the floor, the view line (direct versus partial), and the exposure. The interior can be renovated, but the floor and view cannot, so higher floors and better views hold their value better. How much more they command varies by building, line, and condition, which is why we read it unit by unit against real comparable sales rather than a single headline figure.

Jon Brooks, Momentum Realty
Operator Note

Most buyers overpay on interior lots in the back half of the community. A sharp renovation can distract you, but the weaker resale position follows the lot, not the finishes. We read the homesite before the kitchen.

Resale Strength Scorecard

How well Cottages at Winding Creek holds value.

Our read on the factors that protect resale here, and the one to manage.

No CDD on the tax billStrong
Central Intracoastal West locationStrong
Scarce golf and lake homesitesStrong
$30M club reinvestment to 2028Positive
All-resale 1990s conditionManage it

Momentum analysis based on the community's structure, location, lot scarcity, and housing stock. Not a guarantee of future value.

Jon Brooks, Momentum Realty
Operator Note

The strongest value pocket is usually a renovated home on a good lot priced just under the next tier up. Buyers chasing the single biggest house often pay top prices for what is really a renovation project.

5 Mistakes Buyers Make in Cottages at Winding Creek

15-Second Take
  • Calling the listing agent (who works for the seller)
  • Misjudging the renovation budget
  • Overpaying for an interior lot
  • Underbudgeting the carrying costs
  • Skipping the roof, HVAC, and systems check

The same five mistakes cost buyers the most in any market. Every one is avoidable with the right preparation before you tour.

Cottages at Winding Creek1

Calling the listing agent

The agent on the sign works for the seller. In a market where condition swings price by hundreds of thousands, negotiating against that agent with no one in your corner is the costliest move of all.

Cottages at Winding Creek2

Misjudging the renovation math

A dated home looks like a deal until you price the roof, HVAC, pool, and full modernization honestly. Underbudget the reno and the bargain becomes the expensive house.

Cottages at Winding Creek3

Overpaying for an interior lot

A premium homesite (water, preserve, or a preferred position) carries a real, durable premium. Pay a top price for an interior lot and you are buying the weakest version of the value.

Cottages at Winding Creek4

Underbudgeting the carrying costs

Two similar homes can cost very differently to own once the HOA, any CDD, insurance, and upkeep are priced in. Buyers who do not run the full monthly carrying cost misread the real number.

Cottages at Winding Creek5

Skipping the systems check

An older home means older systems unless updated. Roof age, HVAC age, pool equipment, and prior renovations drive both price and insurability, and a thorough inspection matters more here than in a new build.

“

Cottages at Winding Creek is about an attainable, low-maintenance home in a top St. Johns County school district, not new construction or a beach address. The deal is read in the home's condition, the HOA, and the lot, not the sticker.

Jon Brooks · Founder, Momentum Realty
Momentum Intelligence

Momentum Buy Score.

Our proprietary 0 to 10 read across the five factors that decide how a home here buys, holds, and resells.

7.1B · Buy Score
Resale Strength7.2/10
Renovation Risk5.2/10
Location Efficiency7.6/10
Long-Term Defensibility7.0/10
Carrying Cost Advantage7.0/10

Momentum Intelligence Scores are our proprietary, qualitative assessment based on the analysis on this page, on a 0 to 10 scale. They are a framework for comparing communities, not a guarantee of future value or advice on a specific home.

Momentum Housing Intelligence

Why our read on Cottages at Winding Creek is different.

Most pages on this community are an automated estimate wrapped in stock copy. This one is built from the live realMLS feed, fourteen years of closed sales, and a renovation-by-renovation read of what actually moves value here, lot by lot. No automated estimate, no guesswork.

Live realMLS feed14 years of closed salesRenovation-premium analysisLot-by-lot, no automated estimates
Jon Brooks, founder of Momentum Realty. A housing economist with a background in real estate investment banking and consulting at Ernst & Young, who has built and analyzed Northeast Florida real estate from the ground up.
About the analyst · Our methodology

Which Lots & Views Hold Value Best

Proprietary Data · Unit Value Map

Where the value actually sits. Each home is shaded by its price per square foot (a value read, not just a price) and ringed by lot type, so you can see at a glance which pockets carry a real, durable premium and where a renovation play makes sense.

Value ($/sqft)
$261 value$401 premium

Fill = price per square foot; ring = by realized $/sqft per unit. Sold homes are shown by realized $/sqft (lot type not always recorded). Asking and recent-sold figures from realMLS; for orientation, not an appraisal.

15-Second Take
  • The lot and the home's condition are the value; confirm what the HOA maintains.
  • Roof age and systems drive cost on a late-2000s home.
  • Comp house by house, not a county median.

In an attainable, established community like Cottages at Winding Creek, the lot and the home's condition are the value, and the top St. Johns County school district is the durable demand driver. Because the homes date to the late 2000s, the honest approach is to inspect the roof and systems, confirm the HOA dues and the FEMA flood zone, and price the specific home on its condition and lot against the closest comparable Cottages at Winding Creek sale rather than a county median.

The 15-Second Verdict

Cottages at Winding Creek in 15 seconds.

Best forBuyers who want an attainable, established home in the top-rated St. Johns County schools.
Strong onValue and schools: attainable, low-maintenance cottages near historic St. Augustine, I-95, and the beaches.
WatchThe HOA dues, late-2000s condition, and any flood exposure, all confirmed per parcel.
Not forBuyers who want new construction, a large or estate home, a beachfront address, or no HOA.
The edgeAn attainable entry into the top St. Johns County school district with a low-maintenance home.

HOA, CDD & Fees

15-Second Take
  • There is an HOA; confirm the current dues and exactly what they cover.
  • Confirm whether any CDD applies on the St. Johns County tax bill.
  • Budget late-2000s maintenance, not a large fee load.

Cottages at Winding Creek carries a homeowners association; the current dues figure is not published here and should be confirmed with the association, along with what it covers and any reserve or special-assessment items. Confirm whether any CDD applies for a community of this vintage on the St. Johns County tax bill.

The HOA assessment typically funds the common areas and may include some exterior or grounds maintenance for a cottage-style community; confirm exactly what is included before you rely on it.

There is no private golf or country club tied to the community; this is an attainable, low-maintenance single-family community rather than an amenity or golf community.

Run Your Numbers

Tools for a Cottages at Winding Creek buy.

Free calculators to pressure-test the real cost before you tour.

Mortgage paymentPrincipal, interest, taxes, and insurance on a specific price.Property taxSt. Johns County millage and the homestead picture.Rent vs buyThe breakeven on owning in Cottages at Winding Creek.Save Our HomesProject your homestead tax cap over time.
The takeaway

Selling here is won on condition and view, not an automated estimate. The right number comes from closed comps matched to your renovation level and lot.

Selling in Cottages at Winding Creek

Thinking of selling in Cottages at Winding Creek?

Your buyer is paying for the St. Johns County schools and an attainable, low-maintenance home, so sell what is specific and verifiable: the updates you have made, the roof and systems, the HOA, and a clean flood read.

Momentum listings (YTD)
97.98%
Sold-to-list ratio across the Jacksonville metro for our agents, sellers keeping more of their price.
Market average (YTD)
96.73%
The broader metro average sold-to-list ratio over the same period.
Momentum days on market
64 days
Median days on market for our listings, faster sales mean less carrying cost and stronger leverage.
Market days on market
72 days
The broader metro median over the same period.

Sold-to-list and days-on-market figures reflect Momentum Realty listings versus the Jacksonville metro average, year to date. Your home's result depends on pricing, condition, lot, view, and preparation.

In Cottages at Winding Creek, condition and view decide your number

Because buyers here are weighing your home against renovated comps and cross-shopping Samara Lakes, a home priced to the community average instead of its true condition and view either leaves money on the table or sits. A renovated kitchen, newer roof and HVAC, and a golf or lake view all deserve to show up in your price, and a buyer pool reading renovation math needs to be shown why your home is worth it. We build that case with real comps and a pricing strategy for the current market.

What is your Cottages at Winding Creek home worth?

Get a no-obligation home value based on real comparable sales in Cottages at Winding Creek matched to your condition, lot, and view, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.

See homes for sale in Cottages at Winding Creek on the map →

Real comps, not an automated estimate.
>>>>>>> origin/main

Windows contain 0 to 11 sales each (7 in the current window); every figure carries its sample size, and thin markets swing on single closings. Source: Data provided by realMLS. Deemed reliable but not guaranteed.

Median sale price · trailing 12 mo
$200K$300K20122014201620182020202220242026
Down 11.1% year over year.
Every sale since 2009 · price vs size
$0$100K$200K$300K1k2k2k
81 closed sales; green = recent. Size sets the floor, condition and lot set the rest.
Sold $ per sq ft · trailing 12 mo
$100$150$20020122014201620182020202220242026
Up from $89 in 2012 to a $202 peak in 2024; $185 now.
Median days on market · closed sales
05010015020122014201620182020202220242026
14 days at the 2022 low; 104 now.
Sale price vs original ask · median
92%95%98%20122014201620182020202220242026
94.6% now.
Homes sold per 12-mo window
051020122014201620182020202220242026
0 to 11 a year; 7 in the current window.
Sellers who gave up · failed listings per year
05101520102018202220242025
Canceled, expired, or withdrawn. 16 quit in 2010; 0 so far in 2025. The clearest stress gauge a community has.
Market Heat · 0 coldest, 100 hottest in the record
20406080seller-leaningbuyer-leaning20182020202220242026
82 at the 2022 peak, 15 in the troughs, 15 now. Same score as the hero card, full history.

The real cost & risk here

Before the list price, the Florida math the portals skip. These are St. Johns County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.

$2,612/mo
St. Johns County typical true cost to own
$115/mo
St. Johns County typical home insurance
Check CDD
Confirm before you offer

Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · St. Johns County scorecard.

County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.

How much local inventory is already under contract

20% of homes for sale in ZIP 32086 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-07-18).

Cottages at Winding Creek Market Scorecard

Strong seller's market

Cottages at Winding Creek is currently a strong seller's market. About 1.7 months of supply, a median asking price of $289,900, and homes go under contract in about 199 days.

1.7
Months supply
$289,900
Median list
$280,000
Median sold
$173
Per sqft
199
Days on mkt
1/1/7
Active/Pend/Sold

Typical home value in the 32086 ZIP is $372,045, right around the Florida norm (Zillow Home Value Index).

Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.

Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.

Homes For Sale Right Now in Cottages At Winding Creek

Live MLS inventory for Cottages At Winding Creek. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.

215 BAYBERRY Circle #605 home for sale in Cottages At Winding CreekActive · 209 daysTop listing
$289,900
3 bd · 2 ba · 1,680 sqft · built 2007
215 BAYBERRY Circle #605, St. Augustine, 32086
Listed by FLORIDA HOMES REALTY & MTG LLC

Active and pending Cottages At Winding Creek listings as of 2026-07-14, priced high to low. Source: Data provided by realMLS. Tap any home to ask about it.

Interactive Map

Cottages At Winding Creek on the map.

Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.

Listing locations from realMLS. Map data © OpenStreetMap, tiles © CARTO.

Community & Amenities

Life at Cottages At Winding Creek

  • Pool · reported on 8 of 9 listings
  • Gated · reported on 7 of 9 listings
  • Security Gate · reported on 7 of 9 listings
  • Maintenance Grounds · reported on 4 of 9 listings
  • Clubhouse · reported on 3 of 9 listings
  • Trash · reported on 2 of 9 listings
  • Playground · reported on 1 of 9 listings
  • Tennis Court(s) · reported on 1 of 9 listings
  • Entry Phone/Intercom · reported on 1 of 9 listings
  • Security Fence · reported on 1 of 9 listings

Community amenities as reported across realMLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.

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Cottages at Winding Creek Market Scorecard

Strong seller's market

Cottages at Winding Creek is currently a strong seller's market. About 1.7 months of supply, a median asking price of $289,900, and homes go under contract in about 199 days.

1.7
Months supply
$289,900
Median list
$280,000
Median sold
$173
Per sqft
199
Days on mkt
1/1/7
Active/Pend/Sold

Typical home value in the 32086 ZIP is $372,045, right around the Florida norm (Zillow Home Value Index).

Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.

Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.

Frequently Asked Questions

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The Strategy

The Cottages At Winding Creek buying strategy.

If we were buying in Cottages At Winding Creek today, this is the order of operations we would run for our clients.

1

Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Cottages At Winding Creek.

The Quick Decision
Best Buy
Buyers who want a gated, amenity-served home and are comfortable with a thin, low-inventory resale market.
Biggest Risk
With only one active listing and seven recent closings, pricing signals here are volatile and easy to misread.
Sweet Spot
Buyers targeting the $280,000 median price point who are willing to wait out a 104-day typical selling timeline.
Avoid If
You need a fast, guaranteed-inventory purchase — with one listing active, timing is largely out of your control.
The Deep Dive

A Small, Amenity-Dense Pocket

The amenity package here is dense for the price point: a gated entry with a security gate, entry phone/intercom, and security fence, plus a clubhouse, pool, tennis court(s), and playground, with grounds maintenance and trash handled through the HOA. That combination points to a community built for low-maintenance ownership rather than large individual yards — buyers are paying for shared infrastructure and access control, not square footage on a private lot. As always with HOA-reported amenities, current access and condition should be verified directly with the HOA before writing an offer.

On the numbers, this is a market where the sample size matters more than usual. Seven closings and one active listing is not enough data to draw firm conclusions about direction, and the 11.1% year-over-year decline in median price should be read in that light — it is a real number, but it is also a number that a single high- or low-priced closing can move substantially. The 104-day median time on market, set against a seller-leaning supply picture of 1.5 months, suggests homes here sell on patience and correct pricing rather than on scarcity alone.

“

The location and the amenities are priced into every listing in Cottages At Winding Creek. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty
Momentum Intelligence

Momentum Buy Score.

Our proprietary 0 to 10 read across the factors that decide how a home in Cottages At Winding Creek buys, holds, and resells. Momentum Research; not an appraisal.

6.0C+ · Buy Score
Recent Direction3.2/10
Liquidity & Demand8.5/10
Pricing Power6.4/10

Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (6.0). Basis: Recent Direction -11.1% year-over-year; Liquidity & Demand 1.5 months of supply; Pricing Power 94.6% sale-to-list. Refreshed with each data update.

Why Momentum

Why work with Momentum here

A community this thin on transaction volume punishes generic pricing advice — with only seven closings and one listing active, a comp-pull that does not account for condition and unit-level differences will mislead a seller or a buyer. Momentum treats a market like this as a case-by-case pricing exercise, weighing the $280,000 median and $184.79 per square foot against the specific unit rather than the community-wide average, and building offers or list prices around the real 104-day selling pattern instead of what a low months-of-supply figure implies on its own.

The 15-Second Verdict

Cottages At Winding Creek in 15 seconds.

Best forBuyers who want a gated, amenity-served home and are comfortable with a thin, low-inventory resale market.
Biggest advantageA dense amenity package — pool, clubhouse, tennis, playground, and gated security — bundled into HOA-maintained grounds.
Biggest riskWith only one active listing and seven recent closings, pricing signals here are volatile and easy to misread.
Sweet spotBuyers targeting the $280,000 median price point who are willing to wait out a 104-day typical selling timeline.
Avoid ifYou need a fast, guaranteed-inventory purchase — with one listing active, timing is largely out of your control.

HOA, CDD & Fees

In short
  • Mandatory HOA — confirm current dues
  • Any club/amenity membership is billed separately

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.

Run Your Numbers

Tools for a Cottages At Winding Creek buy.

Free calculators to pressure-test the real cost before you tour.

Mortgage paymentPrincipal, interest, taxes, and insurance on a specific price.Property taxSt. Johns County millage and the homestead picture.Rent vs buyThe breakeven on owning in Cottages At Winding Creek.Save Our HomesProject your homestead tax cap over time.
The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Cottages At Winding Creek sales matched to your home.

Selling in Cottages At Winding Creek

Price it to the comps and condition, not an automated estimate.

If you are thinking about selling in Cottages At Winding Creek, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.

What is your Cottages At Winding Creek home worth?

Get a no-obligation home value based on real comparable sales in Cottages At Winding Creek, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.

See homes for sale in Cottages At Winding Creek on the map →

Real comps, not an automated estimate.

Frequently Asked Questions

What is the median home price in Cottages At Winding Creek?
The median sale price in Cottages At Winding Creek was $280K over the 12 months ending July 14, 2026 (7 closed sales, realMLS).
How long do homes in Cottages At Winding Creek take to sell?
Homes that closed in the 12 months ending July 14, 2026 took a median 104 days on market (7 sales, realMLS).
Is Cottages At Winding Creek a buyer's or seller's market right now?
As of July 14, 2026, Cottages At Winding Creek is roughly balanced: 1.5 months of supply at the current sales pace (realMLS live counts).
Do cash buyers compete in Cottages At Winding Creek?
Cash buyers took 40% of Cottages At Winding Creek sales in the 12 months ending July 2025 (2 of 5 closings, realMLS).
Who is the best real estate agent for Cottages At Winding Creek?
The best agent for Cottages At Winding Creek is one who actively works St. Augustine and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Cottages At Winding Creek.
How do I find a top St. Augustine real estate agent who knows Cottages At Winding Creek?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Cottages At Winding Creek and the wider St. Augustine area.
Can Momentum Realty connect me with an agent for Cottages At Winding Creek?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Cottages At Winding Creek purchase or sale - no call center and no pressure.
The Verdict

Should you buy in Cottages At Winding Creek?

An honest fit check. We will tell you when it is not your community.

Buyers who want low-maintenance ownership and are comfortable with grounds, pool, and clubhouse access handled through an HOA.Excellent fit
Buyers targeting a purchase near the $280,000 median who can move decisively once a rare listing appears.Excellent fit
Buyers prioritizing gated access and on-site recreation (pool, tennis, playground) over a large private lot.Excellent fit
Buyers who need to choose from multiple active listings right now — there is only one on the market.Probably not
Buyers unwilling to accept HOA dues and rules in exchange for maintained common areas and security features.Probably not
Sellers expecting a quick, no-negotiation close — the 104-day median time on market argues against that assumption.Probably not

Nearby Communities

Explore more neighborhoods near Cottages At Winding Creek with Momentum Realty’s local guides.

Browse all Florida neighborhood guides →

Data sources & freshness

Live listingsrealMLS, refreshed twice daily (last: July 14, 2026)
Community market statsrealMLS closed sales, 12-month windows ending July 14, 2026
Under-contract sharesrealMLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2009 (81 transactions analyzed)

Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.

Momentum Research figures are our own analysis of realMLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.

Own a home here?

You just read the data. Now see what your home is worth.

The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the realMLS member average and 8 days faster, and we’ll price yours against live your area comps.

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