Winding Woods Homes for Sale in Ormond Beach, FL

Established 1988 · Intracoastal West · ZIP 32224

An established single-family neighborhood of well-kept block homes in west Ormond Beach, with an HOA dating to the early 1980s and quick I-95 access.

Single-familyEstablished HOAWest Ormond Beach

Live Market Pulse

49/100
Momentum

Buyer-Leaning 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 Winding Woods

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

Built fromLive DBAAR data14 years of closingsLocal renovation analysisUpdated twice daily

LiveMarket PulseDBAAR

$338K

Median Price

6mo

Supply

174days

Avg DOM

Soft

Seller Leverage

$199/sf

Median $/Sqft

+10%

1-Yr Price Change

0now

Distress

Jon's Current Read

"Winding Woods is a mature single-family neighborhood in west Ormond Beach, organized by a homeowners association that has been in place since 1980, and the read is settled, mid-market value. Homes are solid concrete-block construction with flexible layouts, on a quiet, tree-lined street pattern near the Granada Boulevard and Interstate 95 corridor. The trade is that it is a finished, established neighborhood, so the purchase is about the specific home's condition and updates rather than new construction or resort amenities."

Jon Brooks, founder, Momentum Realty · Updated June 2026

The 60-Second Overview

Winding Woods market snapshot (as of June 25, 2026): the median sale price is about $338K ($199 per sq ft), with homes averaging 174 days on market and 6.0 months of supply, a buyer-leaning market (limited data). Values are up 10% over the past year, based on 4 recent closings in live Daytona-area MLS data.

Winding Woods is a single-family neighborhood in west Ormond Beach, Volusia County, near the Granada Boulevard (State Road 40) and Interstate 95 corridor. It is an established, settled community rather than a new or gated development.

The Winding Woods Homeowners Association has been in place since 1980, which dates the neighborhood's core to the early 1980s. Homes are well-maintained concrete-block construction, with common layouts of three bedrooms and two baths plus a flexible office or den that can serve as a fourth bedroom.

The location pairs a quiet residential feel with convenience: Granada Boulevard shopping and Interstate 95 are a short drive, downtown Ormond and the Halifax River are nearby to the east, and Ormond's beaches are a manageable drive away.

Because Winding Woods is a finished neighborhood of early-1980s homes, the purchase is about the individual home: the roof and systems ages, any updates, and the lot, compared against the closest similar sale rather than a neighborhood-wide average.

Quick Match

Who Winding Woods is best for.

Best for

Buyers who want a solid, established single-family block home in west Ormond Beach
Buyers who value a managed neighborhood with an HOA and a quiet street
Those who want flexible layouts and quick Granada and I-95 access

Probably not for

Buyers who want new construction or a gated, amenity-rich master community
Anyone seeking a low-maintenance condo or waterfront
Buyers who want no HOA at all

Market Pulse

How Winding Woods is performing right now

49/100
momentum

Buyer-Leaning Market (limited data)

Seller's marketBalancedBuyer's market

6Months of supplytight

174Median days on marketdays

1 : 2Under contract vs for salestrong demand

4Sold in last 12 monthsliquidity

+127%Median price since 2012appreciation

+7%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 DBAAR, as of June 25, 2026. Refreshed twice daily. Months of supply, days on market, and the contract-to-listing ratio are computed from current Winding Woods listings and the trailing twelve months of closed sales.

Where prices are going$290K2026 YTD

Median sale price by year. Tap a label to compare Twin River Estates or Ormond Beach. 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 foot$1562026 YTD

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

Supply and demand now2 : 1active : pending

For sale2

Pending1

Sold 12mo4

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 Winding Woods buys, holds, and resells. See the five factors.

Homes For Sale Right Now in Winding Woods

Live MLS inventory for Winding Woods. 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.

9 Alicen Court home for sale in Winding Woods

Active · 282 daysTop listing

$279,900

3 bd · 2 ba · 1,506 sqft · built 1983

9 Alicen Court, Ormond Beach, 32174

Reno opportunityBest value

Listed by Realty Pros Assured

1 Alicen Court home for sale in Winding Woods

Active · 66 days

$269,900

1 bd · 2 ba · 1,130 sqft · built 1981

1 Alicen Court, Ormond Beach, 32174

Listed by EXIT Beach Realty

28 Marjorie Trail home for sale in Winding Woods

Pending · 60 days

$379,900

3 bd · 2 ba · 1,907 sqft · built 1996

28 Marjorie Trail, Ormond Beach, 32174

Reno opportunityBest value

Listed by Realty Pros Assured

Interactive Map

Winding Woods 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 DBAAR; 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 Winding Woods. They are approximate and vary with traffic and your exact start point.

Granada Boulevard (SR-40)~5 to 10 min · Ormond's main retail corridor

Interstate 95~5 to 10 min · west via Granada Blvd

Ormond Beach (the Atlantic)~15 to 20 min · east toward the beach

Downtown Ormond / Halifax River~10 to 15 min · dining and the river

Tomoka State Park~10 to 15 min · river and nature trails

Daytona Beach~20 min · south via I-95 or Nova Rd

Daytona Beach International Airport~20 to 25 min · via I-95

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 Winding Woods Homes for Sale in Ormond Beach, FL with Momentum Realty’s local guides.

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Whispering Oaks Homes for Sale in Ormond Beach, FLOrmond Beach, FL · 0.3 mi

Broadwater Homes for Sale in Ormond Beach, FLOrmond Beach, FL · 0.4 mi

Heritage Forest Homes for Sale in Ormond Beach, FLOrmond Beach, FL · 0.4 mi

Trails North Forty Homes for Sale in Ormond Beach, FLOrmond Beach, FL · 0.4 mi

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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

Winding Woods (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

Volusia 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

Winding Woods is served by Volusia 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 Winding Woods address.

The takeaway

What is actually relevant to Winding Woods buyers, sourced and dated. We do not publish rumor.

Recent Developments in Winding Woods

Development Intelligence

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

Net OutlookBullishWinding Woods is an established, built-out neighborhood, so activity is resale rather than new development. Central and west Ormond Beach have held value well, supporting steady demand for the neighborhood's solid block homes.

Established HOA-managed neighborhood

BullishA long-standing homeowners association and solid block-home construction support a tidy, stable neighborhood and steady demand. impact

SignificanceRadius: Neighborhood-wide

Established HOA-managed neighborhood

Early-1980s housing stock

NeutralHomes date to the early 1980s, so roof and systems condition and any updates drive value more than a community-wide average. impact

SignificanceRadius: Neighborhood-wide

Early-1980s housing stock

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 Winding Woods, 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 ↓

1980
Development
Winding Woods Homeowners Association established
The Winding Woods Homeowners Association was incorporated in 1980, dating the neighborhood's core to the early 1980s; homes are well-maintained concrete-block construction with three-bedroom, two-bath layouts plus a flexible office or den (state corporate records and brokerage listing sources). Why it matters: The HOA structure and block construction support stability; price the specific home on its roof, systems, and updates, and confirm the current HOA dues. 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 Winding Woods buying strategy.

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

Judge the specific home's condition. Pull the roof, HVAC, electrical, and plumbing ages on an early-1980s block home; condition is the value here.

Confirm the HOA dues and rules. Get the current figure, what it covers, and any restrictions from the Winding Woods association before you write.

Check the FEMA flood zone and drainage. West Ormond has low areas nearby; pull the flood zone for the address and a bindable insurance quote.

Verify the zoned schools by address. Ormond Beach is served by Volusia County Schools; confirm the current zoned schools with the district locator.

Comp within the neighborhood. Price off the closest similar Winding Woods sale, accounting for updates and lot.

The Quick Decision

Best Buy

An updated three-bedroom block home with a newer roof and HVAC, on a dry lot, near the neighborhood's typical range.

Biggest Risk

Deferred maintenance on an early-1980s home (roof, systems) eroding value; price it in.

Best Lot

Higher, dry, tree-lined lots are the safe value; verify drainage on lower lots.

Smart Timing

Central and west Ormond have risen recently (median around $386,000 area-wide; Redfin, 2026); Winding Woods is a solid mid-market option within that.

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

Winding Woods is an established single-family neighborhood in west Ormond Beach, Volusia County (ZIP 32174), near the Granada Boulevard and Interstate 95 corridor, with a homeowners association in place since 1980. Homes are well-maintained concrete-block construction, commonly three-bedroom, two-bath layouts plus a flexible office or den, on quiet, tree-lined streets. There is no resort-style amenity campus; the appeal is solid construction, a managed and settled setting, flexible layouts, and convenient access to shopping, I-95, downtown Ormond, and the beach.

Winding Woods Homes For Sale

What your money buys in Winding Woods.

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 Winding Woods today. The right home is the one matched to your budget and the renovation math, so seeing fitting listings early is the edge.

Entry: original-condition homes

$330K to $335K

Three-bedroom block homes in original condition, candidates for updates, at the lower end of the neighborhood. The value play for buyers willing to renovate; verify roof and systems first.

Lowest entry

Mid: updated three-bedroom homes

$335K to $386K

Move-in three-bedroom, two-bath homes with the flexible den, the core of the neighborhood. Condition and lot separate these more than floor plan does.

Most inventory

High: largest or fully updated homes

$386K to $386K

The most updated homes, or those using the flex room as a fourth bedroom on the best lots, set the neighborhood's ceiling. Condition and lot drive the premium.

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 ~$338K buys here.

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

$330K to $335K

Entry: original-condition homes

Three-bedroom block homes in original condition, candidates for updates, at the lower end of the neighborhood. The value play for buyers willing to renovate; verify roof and systems first.

$335K to $386K

Mid: updated three-bedroom homes

Move-in three-bedroom, two-bath homes with the flexible den, the core of the neighborhood. Condition and lot separate these more than floor plan does.

$386K to $386K

High: largest or fully updated homes

The most updated homes, or those using the flex room as a fourth bedroom on the best lots, set the neighborhood's ceiling. Condition and lot drive the premium.

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 Winding Woods, 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 Winding Woods is too thin right now to compute a reliable renovation premium. We read condition home by home against real comps before you offer.

Lot Value

The lot premium.

On a preferred homesite (water, preserve, corner, or a larger lot), the homesite is the part of your money the market gives back at resale. The house can be renovated; the lot cannot, so premium lots hold their value better than interior ones. How much more they command varies by frontage, view, and condition, which is why we read it home by home 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 Winding Woods 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 Winding Woods

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.

“

Winding Woods sells a solid, established block home on a quiet west Ormond street with a managed HOA and quick I-95 access. The setting and construction are the value; the deal is a sound individual home, not an amenity premium.

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.

7.3B · Buy Score

Resale Strength7.4/10

Renovation Risk6.2/10

Location Efficiency8.0/10

Long-Term Defensibility7.0/10

Carrying Cost Advantage7.6/10

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 Winding Woods is different.

Most pages on this community are an automated estimate wrapped in stock copy. This one is built from the live DBAAR 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 DBAAR 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 · Lot 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

Lake / waterPreserveInterior

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

15-Second Take

Higher, dry, tree-lined lots are the safe value here.
Verify drainage and flood zone on any lower lot.
Condition matters more than lot in this neighborhood; compare like for like.

In Winding Woods, value is driven mostly by the home's condition and updates, since this is an interior, established block-home neighborhood. Higher, dry, tree-lined lots are the safe choice, and lower lots warrant a careful FEMA flood-zone and drainage check plus a bindable insurance quote. Because the homes share a similar early-1980s era and construction, the honest approach is to compare a home against the closest similar sale, accounting for updates and lot, and to underwrite the roof and systems as part of the price.

The 15-Second Verdict

Winding Woods in 15 seconds.

Best forBuyers who want a solid, established single-family block home in a managed west Ormond neighborhood.

Strong onSolid block construction, a long-standing HOA, flexible layouts, and quick Granada and I-95 access.

WatchEarly-1980s home condition (roof and systems) and flood or drainage on lower lots.

Not forBuyers who want new construction, a gated amenity community, a low-maintenance condo, or no HOA.

The edgeA stable, HOA-managed neighborhood of solid block homes in a strong Ormond submarket near I-95.

HOA, CDD & Fees

15-Second Take

A long-standing HOA manages the neighborhood; confirm the current dues and rules.
There is no amenity campus, so carrying cost stays moderate.
Block construction is a plus; the roof and systems age is the variable.

Winding Woods is managed by the Winding Woods Homeowners Association (in place since 1980). Confirm the current dues, what they cover, the reserve picture, and any rules with the association before you buy.

The dues typically fund common-area upkeep and community standards; confirm the current breakdown with the association. Homes are individually maintained on their own lots.

There is no golf or resort club; this is a residential single-family neighborhood with a homeowners association rather than an amenity campus. Recreation comes from nearby Ormond parks, the rivers, and the beach.

Run Your Numbers

Tools for a Winding Woods buy.

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

Mortgage paymentPrincipal, interest, taxes, and insurance on a specific price.Property taxVolusia County millage and the homestead picture.Rent vs buyThe breakeven on owning in Winding Woods.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 Winding Woods

Thinking of selling in Winding Woods?

Your buyer wants a solid, well-located Ormond home with a managed HOA. Sell what is specific: the updates, the roof and systems, the block construction, and the flexible layout.

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 Winding Woods, condition and view decide your number

Because buyers here are weighing your home against renovated comps and cross-shopping Twin River Estates, 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 Winding Woods home worth?

Get a no-obligation home value based on real comparable sales in Winding Woods 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 Winding Woods 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 Volusia County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.

$1,789/mo

Volusia County typical true cost to own

$151/mo

Volusia 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 · Volusia 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.

Winding Woods Market Scorecard

Buyer-Leaning Market (limited data)

Winding Woods is currently a buyer-leaning market (limited data). About 4.8 months of supply, a median asking price of $274,900, and homes go under contract in about 179.0 days.

4.8

Months supply

$274,900

Median list

$340,000

Median sold

$194

Per sqft

179.0

Days on mkt

2/0/5

Active/Pend/Sold

Typical home value in the 32174 ZIP is $371,102, about 10.1% above the Florida norm (Zillow Home Value Index).

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

Frequently Asked Questions

Where is Winding Woods?

It is an established single-family neighborhood in west Ormond Beach, Volusia County, near the Granada Boulevard (SR-40) and Interstate 95 corridor, with downtown Ormond and the Halifax River nearby to the east.

When was Winding Woods built?

Its homeowners association was established in 1980, dating the neighborhood's core to the early 1980s. Homes are well-maintained concrete-block construction.

What kinds of homes are in Winding Woods?

Single-family block homes, commonly three-bedroom, two-bath layouts plus a flexible office or den that can serve as a fourth bedroom.

Does Winding Woods have an HOA?

Yes. The Winding Woods Homeowners Association has been in place since 1980. Confirm the current dues, what they cover, and any rules with the association.

How much do homes cost in Winding Woods?

It is a solid mid-market Ormond neighborhood; pricing varies with the home's condition, updates, and lot. The broader Ormond Beach median was around $386,000 in 2026 (Redfin). Confirm current pricing for the specific home.

What schools serve Winding Woods?

The neighborhood is served by Volusia County Schools, with assignments set by home address. Verify the current zoned schools with the district's locator.

Is Winding Woods gated?

No. It is a managed but ungated residential single-family neighborhood with a homeowners association rather than a gate or amenity campus.

What is the construction like?

Homes are concrete-block construction, which many Florida buyers prefer for durability and insurance. Still verify the roof age and systems on any early-1980s home.

What is the location like?

Quiet but convenient: Granada Boulevard shopping and Interstate 95 are a short drive west, downtown Ormond and the river are minutes away, and the beach is a manageable drive east.

What should I verify before buying?

Confirm the home's roof and systems ages, the current HOA dues and rules, the FEMA flood zone and drainage, and a bindable insurance quote.

How does it compare to Twin River Estates nearby?

Twin River Estates trends toward larger homes on bigger lots; Winding Woods is a solid, more mid-market block-home neighborhood. Compare the home size, lot, and all-in cost that fit your needs.

Is Winding Woods a good value?

For buyers who want a solid, established block home in a managed west Ormond neighborhood, yes. The key is buying the right individual home, so verify condition, the HOA, and flood status before deciding.

Who is the best real estate agent for Winding Woods?

The best agent for Winding Woods is one who actively works Ormond Beach 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 Winding Woods.

How do I find a top Ormond Beach real estate agent who knows Winding Woods?

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 Winding Woods and the wider Ormond Beach area.

Can Momentum Realty connect me with an agent for Winding Woods?

Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Winding Woods purchase or sale - no call center and no pressure.

The Verdict

Should you buy in Winding Woods?

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

You want a solid, established single-family block home in west Ormond BeachExcellent fit

You value a managed neighborhood with an HOA and a quiet streetExcellent fit

You want flexible layouts and quick Granada and I-95 accessExcellent fit

You want new construction or a gated, amenity-rich master communityProbably not

You want a low-maintenance condo or waterfrontProbably not

You want no HOA at allProbably not

Get the inside read on Winding Woods

Whether you are buying a renovation project, comparing the lots and views, weighing the carrying costs, or selling your Winding Woods 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 Winding Woods specialist will reach out personally, usually the same day.

Thinking about hiring an agent here? How to find the best real estate agent in Winding Woods - 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. © 2026 Daytona Beach Area Association of REALTORS®, Inc. Information deemed reliable but not guaranteed.

Winding Woods Homes for Sale in Ormond Beach, FL

The 60-Second Overview

Who Winding Woods is best for.

Best for

Probably not for

How Winding Woods is performing right now

Homes For Sale Right Now in Winding Woods

Winding Woods on the map.

How far is everything?

Nearby Communities

Schools

Recent Developments in Winding Woods

Established HOA-managed neighborhood

Early-1980s housing stock

Winding Woods Homeowners Association established

The Winding Woods buying strategy.

The full read, only if you want it.

What your money buys in Winding Woods.

What ~$338K buys here.

Renovation & Resale Intelligence

The renovation premium.

The lot premium.

How well Winding Woods holds value.

5 Mistakes Buyers Make in Winding Woods

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 Winding Woods is different.

Which Lots & Views Hold Value Best

Winding Woods in 15 seconds.

HOA, CDD & Fees

Tools for a Winding Woods buy.

Thinking of selling in Winding Woods?

In Winding Woods, condition and view decide your number

What is your Winding Woods home worth?

Price History: What Homes Here Have Actually Sold For

The real cost & risk here

Winding Woods Market Scorecard

Frequently Asked Questions

Should you buy in Winding Woods?

Get the inside read on Winding Woods

You are all set.

Need to sell fast in Duval County?

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

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