Winding Stream
Condos for Sale in Estero, FL
All 253 homes for sale in Estero, FL · median $325,000 · 203 condos for sale in Estero · 53 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 November 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. Homes listed or recently sold were built 2001–2002; 3 of 3 report an HOA (median $763/mo); none of the 3 geocoded homes sit in a FEMA special flood hazard zone (median elevation 16 ft). 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).
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.
Figures in this note are as of July 29, 2026. The live market numbers elsewhere on this page update nightly and are newer.
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 November 11, 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), 1,382 homes closed in the last 12 months at a median of $476K ($285/sq ft), up 0.2% year over year, with a median 67 days on market. Right now 462 active and 136 pending listings put supply at about 4.0 months — a balanced 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.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Lee County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Lee 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.
19% 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 (2026-11-10).
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 230 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.
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 · 42 daysTop listingActive · 230 daysActive and pending Winding Stream listings as of 2026-11-10, 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.
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 contributors.
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.
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.
See all homes for sale in Estero →
| 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.
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.
Just listed in Winding Stream
The newest homes for sale in Winding Stream right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 9331 Spring Run Blvd 3005 $364,900 · 2 bd · 2 ba · 1,333 sq ft · listed Sep 30, 2026 Courtesy of Royal Shell Real Estate, Inc.
- 9321 Spring Run Blvd 2907 $309,900 · 2 bd · 2 ba · 1,209 sq ft · listed Mar 13, 2026 Courtesy of Downing Frye Realty Inc.
Checked against the MLS nightly. All new listings in this market.
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 · $364,900 · 2 bd / 2 ba · listed Sep 16, 2026 · listed by Royal Shell Real Estate, Inc.
- 9321 Spring Run Blvd 2907 · $309,900 · 2 bd / 2 ba · listed Aug 12, 2026 · listed by Downing Frye Realty Inc.
- 9241 Spring Run Blvd 2206 · $344,000 · 2 bd / 2 ba · pending · listed Aug 12, 2026 · listed by Local Real Estate LLC
More Estero home searches
- All homes for sale in Estero, FL
- Homes for sale in Lee County, FL
- Estero home values: what is my house worth?
- ZIP 34135 housing scorecard
- 7 coming-soon communities in Lee County
Estero guides & data
- Market data
- Best neighborhoods (ranked by data)
- Flood zones
- Home insurance cost
- New construction
- ZIP codes
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
- Cheapest places to live in Florida
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What it really costs to own in Winding Stream
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| Property tax | Current owners' bills run a median of $5,350/yr across 6 listings here (MLS tax records, 2026-11-11). |
|---|---|
| HOA dues | Median $9,159/year (about $763/month) across 3 MLS listings (most billed annually; 2026-11-11). Dues cover what the documents say they cover; ask for the budget and reserve study. |
| Home and flood insurance | The average Citizens Property Insurance premium in Lee County is $2,197/yr (6,508 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 2002 across 6 listings. An original roof here would be about 24 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Winding Stream
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Winding Stream Condos for Sale
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Winding Stream Condos for Sale will answer, and the answer is published on this page for the next buyer.
Recent Developments in Winding Stream
Development, infrastructure, retail, and school activity affecting Winding Stream, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Builder Activity
Kolter Urban's 24-story Island at West Bay Club tops out in Estero
The 86-residence tower reached its highest point at an Oct. 30 ceremony, roughly the construction midpoint, with completion expected in mid-2027. Residences start at $2.7 million, and the building has a rooftop pool plus access to the community's golf, tennis and beach club. Estero's mayor said it may be the village's last high-rise because suitable land is scarce.
What it may mean for the marketAdds 86 high-end condominium homes to Estero's inventory in 2027 while signaling limited future high-rise capacity in the village. The site is about 1 mile west of Winding Stream.
Source: Gulfshore Business - October 2026Parks & Amenities
Sale of 11.4-mile rail corridor for Bonita Estero Rail Trail nears closing
Estero, Bonita Springs and Collier County are set to buy the Seminole Gulf Railway corridor for $60 million, with closing expected by Jan. 14, 2027. Soil testing found elevated arsenic and hydrocarbons that consultants say can be managed with engineering controls. The corridor is planned as the multiuse Bonita Estero Rail Trail.
What it may mean for the marketA continuous trail through Estero and Bonita Springs would add a walking and biking route connecting residential areas to shopping and regional trails. The site is about 2 miles north of Winding Stream.
Source: Gulfshore Business - October 2026Retail & Dining
Whataburger opens in Estero with 158 seats
Whataburger opened its second Southwest Florida restaurant at 22927 Lyden Drive in Estero, across U.S. 41 from Coconut Point. The restaurant seats 158 and employs about 80 people. It is open daily from 6 a.m. to 11 p.m.
What it may mean for the marketAdds a late-hours dining option and roughly 80 jobs near the Coconut Point retail area. The site is about 2 miles north of Winding Stream.
Source: Gulfshore Business - September 2026Development
Ritz-Carlton Residences, Estero Bay tops off second tower
The second of two 22-story towers at 5000 Coconut Road reached full height on Sept. 18, 2026, completing the 224-residence project by London Bay and Coastal Construction. Tower One is more than 90% purchased and Tower Two about 45%. Move-ins and completion are scheduled for August 2027.
What it may mean for the marketAdds high-end waterfront condominium inventory in the Estero and Bonita Springs area, with completion expected in August 2027. The site is about 2 miles southeast of Winding Stream.
Source: Gulfshore Business - August 2026Development
Audubon and Cameratta settle lawsuit over 10,000-home Kingston community
Audubon and Cameratta Companies settled a federal suit over the Kingston permit; Cameratta will buy about 98 acres off Carter Road and give up a 100-foot easement for a road through Corkscrew Swamp Sanctuary. Kingston covers about 6,700 acres in eastern Lee County, with first model homes expected within about two months.
What it may mean for the marketRemoves a legal obstacle to a master-planned community of about 10,000 homes east of Estero, and rules out a road link into Collier County through the sanctuary. The site is about 12 miles east of Winding Stream.
Source: Gulfshore Business - June 2026Retail & Dining
High 5 Entertainment underway at Village Hub SportsPark in Estero
Vertical construction is underway on a High 5 Entertainment venue at the Village Hub SportsPark on the north side of Williams Road in Estero. The facility will include the 21-court Estero Pickleball Club, a 16-lane bowling alley, two miniature golf courses, an arcade, a full-service kitchen and bar, and retail space. The CEO said construction should finish within six to eight months, targeting soft openings in February 2027.
What it may mean for the marketA new entertainment and dining venue adds recreational and commercial space to the Estero activity hub. The project is about 2 miles north of Winding Stream, elsewhere in Lee County.
Source: Gulfshore Business
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.
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: November 10, 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.
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More on Winding Stream Condos for Sale in Estero
- Home values · What homes in Winding Stream Condos for Sale in Estero actually sell for