WOODLANDS WINDERMERE
Homes for Sale in ORLANDO, FL
True comps, carrying-cost math, and listings before the portals.

This is a small, established pocket of Orlando - 108 homes total, all built within a tight 1979-1987 window - and it trades infrequently. With only 1 closing in the most recent window and just 3 active listings against a 36-month supply figure, the math here is about scarcity of transactions more than scarcity of homes. A market like this moves on individual sellers' timing, not on volume.
The 87% homestead share tells the real story: most owners here are not moving. That keeps inventory thin and gives whichever few homes do list some leverage on timing, even though the broader market_band reads buyer-leaning. For a buyer, that means patience and readiness - when something in this size range comes up, there is not a deep bench of competing inventory to choose from instead.
WOODLANDS WINDERMERE right now
🟢 Buyer-leaning market. 18.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of August 2, 2026. Confidence: Low (3 active and pending listings, 1 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Woodlands Windermere Orlando is a compact, older-vintage Orange County community of larger-format homes - the median living area runs north of 2,600 square feet - built almost entirely within a single decade in the early-to-mid 1980s.
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.
The setting & the homes.
Aerial and on-site photos of WOODLANDS WINDERMERE. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Who WOODLANDS WINDERMERE is best for.
Best for
- Buyers specifically looking for larger square footage in an early-1980s-built home
- Buyers comfortable moving deliberately in a market with very few active listings
- Sellers with long tenure whose homes reflect the community's established condition profile
Probably not for
- Buyers who need several comparable listings to shop and compare before deciding
- Anyone expecting community amenities as part of the purchase - none are currently identified
- Buyers on a tight closing timeline who cannot wait for the right listing to surface
The market around WOODLANDS WINDERMERE
WOODLANDS WINDERMERE is a small community — 17 recorded sales on file, most recently in 2026 — too few for its own price trend. Here is the market around it.
In ZIP 32835, 308 homes are on the market and 17% are under contract — a slower corner of ORLANDO.
Across Orange County, 5,873 homes are active and 2,054 pending (26% under contract).
Homes here are single family residence.
ZIP and county figures describe the wider market, not WOODLANDS WINDERMERE specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in WOODLANDS WINDERMERE, ORLANDO
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. Based on Stellar MLS data distributed by MLS GRID for the period August 2026 through August 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in WOODLANDS WINDERMERE
Live MLS inventory for WOODLANDS WINDERMERE. 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 WOODLANDS WINDERMERE listings as of 2026-08-19, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2025. Tap any home to ask about it.
WOODLANDS WINDERMERE on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Windy Ridge Elem · Elementary
- Chain of Lakes Middle · Middle
- Olympia High · High
Zoned schools reflect the assignments reported on recent WOODLANDS WINDERMERE listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any WOODLANDS WINDERMERE address.
The WOODLANDS WINDERMERE buying strategy.
If we were buying in WOODLANDS WINDERMERE 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 WOODLANDS WINDERMERE.
A community that rarely turns over
With just 108 homes and a homestead share of 87%, this is not a community built for quick resale cycles. Most owners appear to be staying put, which is consistent with the low closing count in the current window. When a home does hit the market, it is competing against very little else - active listings sit at just 3 - but the 36-month supply figure signals that absorption is slow relative to that already-thin pool, not that demand is overwhelming it.
Home sizes cluster large, with a median living area over 2,672 square feet, and the building stock is uniform in age - nearly all homes date to the 1979-1987 span, with a median year built of 1983. That consistency in vintage means condition, updates, and maintenance history will do more to differentiate one listing from another than floor plan or lot position. No community amenities are identified in current MLS data, so buyers should treat this as a standalone housing stock rather than an amenity-driven purchase.
The location and the amenities are priced into every listing in WOODLANDS WINDERMERE. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A market this thin rewards someone who is watching it closely rather than checking in occasionally. With only a handful of active listings and a single closing in the recent window, timing and access to off-market or pre-list conversations matter more than in higher-volume communities. Momentum tracks activity here closely enough to flag movement - on either side of the transaction - before it becomes obvious.
WOODLANDS WINDERMERE in 15 seconds.
HOA, CDD & Fees
- Mandatory HOA - confirm current dues
- 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 WOODLANDS WINDERMERE 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 WOODLANDS WINDERMERE sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in WOODLANDS WINDERMERE, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your WOODLANDS WINDERMERE home worth?
Get a no-obligation home value based on real comparable sales in WOODLANDS WINDERMERE, 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 WOODLANDS WINDERMERE on the map →
WOODLANDS WINDERMERE Market Scorecard
WOODLANDS WINDERMERE is currently a strong buyer's market. About 36.0 months of supply, a median asking price of $840,000, and homes go under contract in about 87 days.
Go deeper: 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
Is WOODLANDS WINDERMERE a buyer's or seller's market right now?
How many homes are in WOODLANDS WINDERMERE?
What share of WOODLANDS WINDERMERE is owner-occupied?
When were the homes in WOODLANDS WINDERMERE built?
Do cash buyers compete in WOODLANDS WINDERMERE?
Who is the best real estate agent for WOODLANDS WINDERMERE?
How do I find a top ORLANDO real estate agent who knows WOODLANDS WINDERMERE?
Can Momentum Realty connect me with an agent for WOODLANDS WINDERMERE?
Should you buy in WOODLANDS WINDERMERE?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near WOODLANDS WINDERMERE with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (8 streets, ZIP 32835)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2014 (24 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 Stellar 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 Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.
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See how WOODLANDS WINDERMERE fits the bigger picture — live prices, inventory, and Momentum Scores:






