Winding Trails
Homes for Sale in Wellington, FL
All 439 homes for sale in Wellington, FL · median $850,000 · 354 homes for sale in 33414 · Palm Beach County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 1 closed sale in winding trails in Wellington, FL, the most recent in November 2021. Across Wellington as a whole, 298 homes closed in the last 12 months at a median of $718,750, 55 median days on market, with 114 homes for sale today. At that median and Palm Beach County's FY2025-26 rate of 18.72 mills, annual property tax runs about $13,450 ($12,680 with the full homestead exemption).
Winding Trails is a small, uniform pocket in Wellington: just 12 homes, all built in 2019, with a median of roughly 4,100 square feet. When product is this consistent in age and scale, price is driven far less by vintage and far more by condition, finish level, and lot position. Two homes here can carry very different numbers for reasons that have nothing to do with the year on the deed.
With so few homes, this is a thin market — a single listing can define the comps for months, and one sale can reset expectations in either direction. The very low homestead share (about 8%) tells you a large portion of these are not primary residences, which tends to mean more discretionary, less urgent sellers. Buyers should expect uneven pacing; sellers should expect that pricing to a specific, defensible comp matters more here than in a larger community where volume smooths out the noise.
Nearby homes for sale
No active listings inside winding trails right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Winding Trails is a newer, low-density enclave in Wellington built out in a single 2019 wave, defined by large floor plans rather than shared amenities. The scale of the homes and the scarcity of inventory are the story here.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Winding Trails is best for.
Best for
- Buyers wanting substantial square footage in newer construction and comfortable with a limited-inventory search
- Owners who value uniform, recent build quality over a shared-amenity lifestyle
- Second-home or non-primary buyers who don't need urgency or volume in the local market
Probably not for
- Buyers on a tighter budget who need a smaller, lower-cost floor plan
- Anyone prioritizing clubhouse, pool, or other shared community facilities
- Buyers who want a high-turnover market with many recent comps to negotiate against
The market around Winding Trails
Winding Trails is too small for its own price trend, so here is the market around it.
In ZIP 33414, 464 homes are on the market and 19% are under contract — a steady corner of Wellington.
Across Palm Beach County, 10,140 homes are active and 3,201 pending (24% under contract).
In ZIP 33414 (Wellington), 895 homes closed in the last 12 months at a median of $670K ($309/sq ft), up 1.6% year over year, with a median 50 days on market. Right now 142 active and 34 pending listings put supply at about 5.2 months — a balanced market. See the live ZIP 33414 housing market and the Palm Beach County market.
ZIP and county figures describe the wider market, not Winding Trails specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in winding trails, Wellington
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc. Deemed reliable but not guaranteed.
Recent Developments in Winding Trails
Development, infrastructure, retail, and school activity affecting Winding Trails, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated August 2026.
- July 2026Market
Palm Beach County Total Home Sales Jump for 10th Consecutive Month
Palm Beach County total home sales rose 22.3% year-over-year in June 2026 to 2,456 transactions, with total dollar volume up 53.90% to $2.7 billion. The single-family median sale price increased to $700,000 and the condominium median rose to $325,000.
What it may mean for the marketRising sales volume and median prices signal strengthening demand and higher valuations across the Palm Beach County housing market. The site is about 10 miles north of Winding Trails.
Source: MIAMI REALTORS - July 2026Development
The Berkeley Palm Beach Breaks Ground at 550 South Australian Avenue in West Palm Beach
The Berkeley Palm Beach broke ground on a 25-story tower with 193 condominium residences at 550 South Australian Avenue overlooking Clear Lake, developed by Al Adelson with Arquitectonica as designer. Sales have exceeded $120 million and completion is anticipated in 2029.
What it may mean for the marketA new 25-story condominium tower adds high-end for-sale housing supply to the downtown West Palm Beach market and continues vertical development along the Clear Lake waterfront. The project is about 9 miles north of Winding Trails, elsewhere in Palm Beach County.
Source: Florida YIMBY - June 2026Development
Developers Plan Two 31-Story Towers for 2085 N Flagler Dr, West Palm Beach
Terra and BH Group filed plans for 281 residential condominiums across two 31-story towers on a 1.55-acre site at 2085 N Flagler Drive in West Palm Beach. The nearly 440,000-square-foot project includes about 4,385 square feet of retail and 362 parking spaces.
What it may mean for the marketTwo proposed 31-story towers would add for-sale condominium supply and ground-floor retail along the North Flagler Drive waterfront in West Palm Beach. The project is about 11 miles north of Winding Trails, elsewhere in Palm Beach County.
Source: Florida YIMBY - June 2026Development
Alton Delray in Delray Beach Breaks Ground with $92 Million Construction Loan
Kolter Multifamily broke ground on Alton Delray, a 386-unit multifamily community across six-story buildings on a 12.31-acre former industrial site at 2101 S. Congress Avenue, backed by a $92 million construction loan from Madison Realty Capital. The plan includes 154 workforce housing units under Florida's Live Local Act and 232 market-rate units, with delivery expected in late 2027.
What it may mean for the marketA 386-unit rental community converts a former industrial parcel into new multifamily supply on the Congress Avenue corridor and adds workforce and market-rate housing to the Delray Beach market. The project is about 9 miles south of Winding Trails, elsewhere in Palm Beach County.
Source: Florida YIMBY - June 2026Development
300-Unit 'The Pierce' Slated for Summer Groundbreaking at 115 N. Federal Highway, Boynton Beach
Affiliated Development's The Pierce, a mixed-use project with 300 apartments and 17,015 square feet of retail at 115 N. Federal Highway in downtown Boynton Beach, is slated to start construction in summer 2026. The unit mix includes 150 market-rate apartments and 150 workforce housing units for households earning 80 to 120% of area median income, with 587 parking spaces.
What it may mean for the marketA 300-unit mixed-use project adds rental housing and retail to downtown Boynton Beach and advances redevelopment along the North Federal Highway corridor. The project is about 4 miles southeast of Winding Trails, elsewhere in Palm Beach County.
Source: Florida YIMBY - May 2026Development
25-Story Mixed-Use Tower to Feature Workforce Housing at 120 S Dixie Hwy, West Palm Beach
Developer Jeff Greene proposed a 25-story tower with 399 apartments at 120 S Dixie Highway in downtown West Palm Beach, with about 160 units set aside for households earning at or below 120% of area median income. The plan includes 7,550 square feet of retail and 236 parking spaces and was reviewed by the city's Plans and Plats Review Committee on May 14.
What it may mean for the marketA proposed 25-story mixed-use tower would add rental housing, including income-restricted units, plus retail space to the downtown West Palm Beach market on the South Dixie Highway corridor. The project is about 10 miles north of Winding Trails, elsewhere in Palm Beach County.
Source: Florida YIMBY
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 Winding Trails buying strategy.
If we were buying in Winding Trails today, this is the order of operations we would run for our clients.
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.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
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 Winding Trails.
A small-batch community of large homes
Everything in Winding Trails came out of the same 2019 build cycle, so you are shopping a single generation of construction at a substantial size — a median near 4,139 square feet. That consistency is an advantage: fewer surprises on systems, roofs, and layouts, and a clearer basis for comparison between homes. The differentiators will be interior updates, how a given lot sits, and how the current owner has maintained the property.
No community amenities surface in the current MLS listings, so do not underwrite this as an amenity-driven lifestyle purchase. The pitch is the home itself and Wellington as a location, not a clubhouse or pool package. If shared facilities are a priority, confirm what — if anything — the HOA actually provides before you get attached.
The location and the amenities are priced into every listing in Winding Trails. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a 12-home community, comps are scarce and each one carries outsized weight. We do the parcel-level work — walking condition, lot, and finish differences that a raw price-per-foot number hides — so buyers do not overpay off a thin data set and sellers price to a comp they can actually defend. In a market this small, that discipline is the whole game.
Winding Trails in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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.
Tools for a Winding Trails buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Winding Trails sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winding Trails, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winding Trails home worth?
Get a no-obligation home value based on real comparable sales in Winding Trails, 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 all homes for sale in Wellington →
Should you buy in Winding Trails?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Beaches MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2021 (1 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 Beaches MLS 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 Beaches MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how winding trails fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Winding Trails
Where is Winding Trails?
Winding Trails is a community in Wellington, Palm Beach County, Florida, ZIP 33414.
Are there homes for sale in Winding Trails right now?
No active listings inside Winding Trails at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Winding Trails have an HOA or CDD?
No HOA is on record for Winding Trails in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
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