Winding Stream
Condos for Sale in Estero, FL
All 215 homes for sale in Estero, FL · median $325,000 · 167 condos for sale in Estero · 49 homes for sale in 34135 · Lee County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Photo via Florida Gulf Coast MLS
As of September 2026, Winding Stream in Estero, FL has 3 homes for sale. Over the 12 months ending 2026-09-20, 11 recorded sales closed at a median of $325,000, $263 per square foot, a median 94 days on market, sellers accepting 92% of original asking (-11% versus the prior year). Homes listed or recently sold were built 2001–2002; 3 of 3 report an HOA (median $763/mo). At the median price and Lee County's FY2025-26 rate of 15.97 mills, annual property tax runs about $5,190 ($4,520 with the full homestead exemption).
| Location | Estero, Lee County, FL · ZIP 34135 |
|---|---|
| Sale prices, last 12 months | $325,000 median across 11 closed sales · $263 per sq ft · -11.0% vs the prior 12 months |
| Days on market (closed sales) | 94 median |
| For sale right now | 3 active, 0 pending · median asking $344,000 |
Data as of September 20, 2026. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winding Stream key facts,” movewithmomentum.com/neighborhoods/winding-stream, data as of September 20, 2026.
Last 30 days in Winding Stream: 1 new listing (median asking $389,000), 1 under contract right now. As of September 29, 2026, Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate.
Winding Stream is trading at a median of $325,000 with price per square foot near $263, and the story right now is time, not price. A median of 94 days on market is long for this price point, and it tells you that sellers who price to the comparable range still have to wait out a slower decision cycle rather than a bidding war.
Pricing here has moved down roughly 11% year over year, and with only 11 closings in the window, the data set is thin enough that a single distressed sale or a single high-end update can swing the median in either direction. A market heat score in the mid-20s puts this squarely in buyer-leverage territory: contingencies, inspection requests, and negotiated closing costs are realistic asks, not longshots.
Winding Stream right now
🔴 Off the recent peak. The trailing-12-month median ($325K) is down 11.0% from the prior 12 months ($365K). With about a dozen 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 Florida Gulf Coast MLS closed sales, 12-month windows ending September 20. Confidence: Medium (11 and 7 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 30, 2026 · Live data: Florida Gulf Coast MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Winding Stream market snapshot (as of September 20, 2026): the median sale price is about $325K ($263 per sq ft over the trailing 12 months of closed sales), and a median 94 days on market for closed sales. The trailing-12-month median is down 11% from the prior 12 months, computed from record-level Florida Gulf Coast MLS closed sales (11 closings in the current window).
In ZIP 34135 (Estero), 1,388 homes closed in the last 12 months at a median of $476K ($285/sq ft), up 0.3% year over year, with a median 67 days on market. Right now 463 active and 136 pending listings — a buyer's market. See the live ZIP 34135 housing market and the Lee County market.
Winding Stream sits in Estero within Lee County, and current MLS activity shows a small, slow-moving resale pool rather than an amenity-driven community with a defined lifestyle package.
The setting & the homes.
Aerial and on-site photos of Winding Stream. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Winding Stream
Winding Stream
Winding StreamPhotos from Florida Gulf Coast MLS listings in Winding Stream; content deemed reliable but not guaranteed.
Who Winding Stream is best for.
Best for
- A buyer with flexible timing who can wait through a longer-than-average closing process
- A value-focused buyer targeting the mid-$300s price point in Lee County
- A buyer willing to independently verify HOA and amenity terms rather than relying on a marketed lifestyle package
Probably not for
- A buyer who needs a confirmed amenity package (pool, clubhouse, recreation) before writing an offer
- A seller expecting a fast sale in line with a hotter Estero submarket
- A buyer relying on year-over-year price trends to project near-term appreciation
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Florida Gulf Coast MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($325K) IS the median in the snapshot above, and the move from 2025 ($365K) IS the -11.0% one-year change.
Windows contain 1 to 15 sales each (11 in the current window); every figure carries its sample size, and thin markets swing on single closings. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
23% of homes for sale in ZIP 34135 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 (2026-09-30).
Winding Stream Market Scorecard
Winding Stream is currently a balanced market., a median asking price of $344,000, and homes go under contract in about 191 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Florida Gulf Coast MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Winding Stream, Estero
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. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Winding Stream
Live MLS inventory for Winding Stream. 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.
Active and pending Winding Stream listings as of 2026-09-30, priced high to low. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Tap any home to ask about it.
Every Home for Sale in Winding Stream Right Now (3)
All 3 active and pending Winding Stream listings with a detail page, newest first, refreshed twice a day from the MLS.
- 9331 Spring Run Blvd 3005 · $389,000 · 2 bd / 2 ba · listed Sep 16, 2026 · listed by Royal Shell Real Estate, Inc.
- 9241 Spring Run Blvd 2206 · $344,000 · 2 bd / 2 ba · listed Jul 1, 2026 · listed by Local Real Estate LLC
- 9321 Spring Run Blvd 2907 · $309,900 · 2 bd / 2 ba · pending · listed Jul 1, 2026 · listed by Downing Frye Realty Inc.
Winding Stream on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Florida Gulf Coast MLS. Map data © OpenStreetMap, tiles © CARTO.
The Winding Stream buying strategy.
If we were buying in Winding Stream 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 Stream.
A market defined by patience
The combination of a 94-day median days-on-market and a market heat score of 25 describes a community where listings sit. That is not automatically a red flag, it is a signal that pricing discipline matters more here than in a faster-moving pocket of Lee County. Homes that are priced to the recent median tend to find buyers; homes priced ahead of it tend to accumulate days without much movement, which then get factored into the next round of comparables.
With only 11 closings in the tracked window and a year-over-year price move of -11%, buyers should treat the median as a directional marker rather than a fixed benchmark. Current MLS listings do not surface a defined amenity package for Winding Stream, so anyone evaluating the community should confirm directly what, if anything, comes with an HOA or shared facilities rather than assuming a standard package.
The location and the amenities are priced into every listing in Winding Stream. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, slow-moving market like Winding Stream, the value of a broker is in reading a thin data set correctly, 11 closings does not give you much room for guesswork on pricing. Momentum pulls the current comparables, confirms what amenities or HOA terms actually apply to a specific listing rather than relying on general assumptions, and builds an offer or listing strategy around the 94-day reality instead of hoping for a faster sale.
Winding Stream in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $763/month (about $9,156/yr) · median of 53 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $763 per month ($9,156 a year) — the median AssociationFee across 53 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
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 Stream 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 Stream sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winding Stream, 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 Stream home worth?
Get a no-obligation home value based on real comparable sales in Winding Stream, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Winding Stream?
How long do homes in Winding Stream take to sell?
Who is the best real estate agent for Winding Stream?
How do I find a top Estero real estate agent who knows Winding Stream?
Can Momentum Realty connect me with an agent for Winding Stream?
Where is Winding Stream, and what county is it in?
Should you buy in Winding Stream?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Florida Gulf Coast MLS, refreshed twice daily (last: September 30, 2026) |
| Community market stats | Florida Gulf Coast MLS closed sales, 12-month windows ending September 20, 2026 |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2013 (108 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 Florida Gulf Coast 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 Florida Gulf Coast MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Winding Stream fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Winding StreamCondos for Sale in Estero
- Home values · What homes in Winding StreamCondos for Sale in Estero actually sell for
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