Cottages at Winding Creek in St. Augustine

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

Established 1988 · Intracoastal West · ZIP 32224

An established, attainable single-family community in St. Augustine, low-maintenance cottage-style homes in the top-rated St. Johns County school district.

Established single-familySt. Augustine, St. Johns CountyAttainable, low-maintenance

Live Market Pulse

59/100
Momentum

Balanced Market (limited data)

Tight supply keeps sellers in control, but dated interiors still trade at a discount, so condition is where buyers win.

Free · No obligation

Unlock Off-Market Cottages at Winding Creek

Listings before the portals, true comps, and the renovation and carrying-cost math, before you tour.

Built fromLive realMLS data14 years of closingsLocal renovation analysisUpdated twice daily

LiveMarket PulserealMLS

$280K

Median Price

1.7mo

Supply

190days

Avg DOM

Balanced

Seller Leverage

$185/sf

Median $/Sqft

n/a

1-Yr Price Change

0now

Distress

Jon's Current Read

"Cottages at Winding Creek is an established single-family community in St. Augustine, St. Johns County, built roughly 2007 to 2010, with attainable, midsize cottage-style homes (Watson Realty; neighborhoods.com, 2026). The read is value in a top-rated school district: homes reported from roughly 1,470 to 1,680 square feet, with recent listings around $300,000 to $320,000. The buy is condition-and-lot on the specific home; confirm the HOA dues, the home's systems, and the FEMA flood zone per parcel. Pricing context is third-party and illustrative; confirm per property."

Jon Brooks, founder, Momentum Realty · Updated June 2026

The 60-Second Overview

Cottages at Winding Creek market snapshot (as of June 25, 2026): the median sale price is about $280K ($185 per sq ft), with homes averaging 190 days on market and 1.7 months of supply, a balanced market (limited data). Based on 7 recent closings in live realMLS data.

Cottages at Winding Creek is an established single-family community in St. Augustine, St. Johns County, ZIP 32086, built roughly 2007 to 2010 (Watson Realty; neighborhoods.com, 2026).

The homes are attainable and midsize, reported from roughly 1,470 to 1,680 square feet, in a low-maintenance cottage style (neighborhoods.com, 2026). Because homes vary in updates and lot, the right comparison is house by house.

Recent listings have run roughly $300,000 to $320,000, an attainable point for the top-rated St. Johns County school district (neighborhoods.com, 2026). Confirm current pricing for any specific home.

St. Augustine offers a strong school district and quick access to historic downtown, I-95, and the beaches. The community carries a homeowners association, so the central diligence items are the HOA dues and what they cover, the home's systems, and the FEMA flood zone per parcel.

A Look Inside Cottages at Winding Creek

The course, the club, the gates.

Real aerial and on-site photos of Cottages at Winding Creek. Swipe to explore the community and its amenities.

Swipe or use the arrows → tap any photo to enlarge

Cottages at Winding Creek

Quick Match

Who Cottages at Winding Creek is best for.

Best for

Buyers who want an attainable, established home in the top-rated St. Johns County schools
First-time and right-size buyers who value a low-maintenance cottage-style home
Buyers who want quick access to historic St. Augustine, I-95, and the beaches
Buyers comfortable pricing an established home by its condition and lot

Probably not for

Buyers who want new construction or a gated amenity community
Buyers who want a large or estate-tier home
Buyers who want a beachfront or oceanfront address
Buyers who want no HOA

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

+127%Median price since 2012appreciation

-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.

Where prices are goingn/a2026 YTD

Median sale price by year. Tap a label to compare Samara Lakes or St. Augustine. The 1-year price change is the median sold price over the most recent year versus the prior year, the same measure most listing sites and local Realtor reports use. It reflects the mix of homes that sold, not the change in any single home's value, which is why median price per square foot is shown alongside it to adjust for home size. In thinly traded neighborhoods, where a sale or two can swing the median, we lead with the mix-resistant price-per-square-foot trend instead.

Price per square footn/a2026 YTD

Median $/sqft by year. 2026 is year to date.

Supply and demand now1 : 1active : pending

For sale1

Pending1

Sold 12mo7

Active and pending listings now vs homes sold in the last 12 months.

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 Creek

Active · 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 Creek

Pending · 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 StSt. Augustine, FL · 0.9 mi

Summer Bay at Grand Oaks Homes for Sale in StSt. Augustine, FL · 1.4 mi

Cordera Townhomes in StSt. Augustine, FL · 1.6 mi

Sawmill Landing Homes for Sale in StSt. Augustine, FL · 1.9 mi

Seasons at Morada Homes for Sale in StSt. Augustine, FL · 1.9 mi

Entrada Homes for Sale in Saint Augustine, FLSaint Augustine, FL · 2.2 mi

Oakbrook Homes for Sale in StSt. Augustine, FL · 2.3 mi

Brookestone Homes for Sale in StSt. Augustine, FL · 2.4 mi

StSt. 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 ↓

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
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

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.

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.

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

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

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

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

$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.

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.

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.

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.

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.

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.

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.

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 Zestimate, 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 at Deutsche Bank 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 the Zestimate. 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 a Zestimate.

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.

$2,601/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.

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 $299,000, and homes go under contract in about 191 days.

1.7

Months supply

$299,000

Median list

$280,000

Median sold

$178

Per sqft

191

Days on mkt

1/1/7

Active/Pend/Sold

Typical home value in the 32086 ZIP is $370,362, 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

Where is Cottages at Winding Creek?

Cottages at Winding Creek is an established single-family community in St. Augustine, St. Johns County, ZIP 32086, near historic downtown, I-95, and the beaches.

When was Cottages at Winding Creek built?

The community was built roughly 2007 to 2010 (Watson Realty; neighborhoods.com, 2026).

What kind of homes are in Cottages at Winding Creek?

Attainable, midsize cottage-style single-family homes reported from roughly 1,470 to 1,680 square feet (neighborhoods.com, 2026). Compare house by house.

What do homes cost in Cottages at Winding Creek?

Recent listings ran roughly $300,000 to $320,000 (neighborhoods.com, 2026, illustrative, not MLS). Confirm current pricing for a specific home.

Is there an HOA?

Yes. The community carries a homeowners association. Confirm the current dues, what they cover, and any reserve or special-assessment items with the association before you write.

Is there a CDD?

Confirm whether any CDD applies for a community of this vintage on the St. Johns County tax bill as a matter of course.

What schools serve Cottages at Winding Creek?

It is in the top-rated St. Johns County School District, with assignments set by address. Confirm the current zoned schools for the specific home with the district before you rely on it.

Is Cottages at Winding Creek near the beach?

St. Augustine Beach and Anastasia Island are about 12 to 18 minutes east, with historic downtown St. Augustine about 10 to 15 minutes away.

What should I check before buying here?

Inspect the roof, HVAC, and any updates on a late-2000s home, read the HOA dues and rules, and pull the FEMA flood zone and an insurance quote for the parcel.

Is the flood risk a concern?

Flood exposure varies by parcel in St. Johns County. The FEMA map is authoritative per address, so pull the determination and an insurance quote for the exact home.

Is Cottages at Winding Creek a good value?

For a buyer who wants an attainable, low-maintenance home in the top St. Johns County school district, it can be. Value depends on the specific home's condition, the HOA picture, and the lot rather than a community average.

Should I use the listing agent to buy here?

No. The listing agent works for the seller. Even on an attainable home, having your own representation, which costs you nothing as the buyer, to read the inspection, the HOA, the flood zone, and comps is the highest-leverage decision you make.

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, HOA and CDD details, 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.

You want an attainable, established home in the top-rated St. Johns County schoolsExcellent fit

You value a low-maintenance cottage-style homeExcellent fit

You want quick access to historic St. Augustine, I-95, and the beachesExcellent fit

You are comfortable pricing an established home by its condition and lotExcellent fit

You want new construction or a gated amenity communityProbably not

You want a large or estate-tier homeProbably not

You want a beachfront or oceanfront addressProbably not

You want no HOAProbably not

Get the inside read on Cottages at Winding Creek

Whether you are buying a renovation project, comparing the lots and views, weighing the carrying costs, or selling your Cottages at Winding Creek home, tell us what you need. Every inquiry comes straight to us. We represent you, not the seller, and what your agent is paid is negotiable and set in a written buyer agreement up front. No obligation, no spam, no high-pressure follow-up.

You are all set.

A Momentum Realty Cottages at Winding Creek specialist will reach out personally, usually the same day.

Thinking about hiring an agent here? How to find the best real estate agent in Cottages at Winding Creek - what to look for, questions to ask, and your local expert.

Photography on this page is sourced from active and recently sold MLS listings in this community and remains the property of the listing brokerage and/or photographer. Source: Data provided by realMLS.

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

The 60-Second Overview

The course, the club, the gates.

Who Cottages at Winding Creek is best for.

Best for

Probably not for

How Cottages at Winding Creek is performing right now

Homes For Sale Right Now in Cottages at Winding Creek

Cottages at Winding Creek on the map.

How far is everything?

Nearby Communities

Schools

Recent Developments in Cottages at Winding Creek

Attainable value in a top school district

Low-maintenance cottage stock

Flood and insurance verification

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

St. Johns County millage

The Cottages at Winding Creek buying strategy.

The full read, only if you want it.

What your money buys in Cottages at Winding Creek.

What ~$280K buys here.

Renovation & Resale Intelligence

The renovation premium.

The unit premium.

How well Cottages at Winding Creek holds value.

5 Mistakes Buyers Make in Cottages at Winding Creek

Calling the listing agent

Misjudging the renovation math

Overpaying for an interior lot

Underbudgeting the carrying costs

Skipping the systems check

Momentum Buy Score.

Why our read on Cottages at Winding Creek is different.

Which Lots & Views Hold Value Best

Cottages at Winding Creek in 15 seconds.

HOA, CDD & Fees

Tools for a Cottages at Winding Creek buy.

Thinking of selling in Cottages at Winding Creek?

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

What is your Cottages at Winding Creek home worth?

Price History: What Homes Here Have Actually Sold For

The real cost & risk here

Cottages at Winding Creek Market Scorecard

Frequently Asked Questions

Should you buy in Cottages at Winding Creek?

Get the inside read on Cottages at Winding Creek

You are all set.

Need to sell fast in Duval County?

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