Stillwater Crossing
Homes for Sale in Windermere, FL
All 244 homes for sale in Windermere, FL · median $966,750 · 230 homes for sale in 34786 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 4 closed sales in Stillwater Xing Prcl Sc-13 Ph 1 in Windermere, FL since 2017, the most recent in June 2025. Across Windermere as a whole, 449 homes closed in the last 12 months at a median of $640,000, 39 median days on market, with 120 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $10,670 ($10,000 with the full homestead exemption).
Stillwater Crossing Ph 1 is a small, single-phase pocket of Windermere with only 60 homes, built out over a decade between 2006 and 2016. That construction window, with a median build year of 2014, means most of the housing stock here is post-recession and reasonably consistent in age, which narrows the usual variability you'd see in an older or multi-phase community.
With no MLS-documented community amenities, pricing here is going to be driven almost entirely by the home itself: lot, floor plan, updates, and living area, which runs to a median of roughly 2,964 square feet. That's a larger-format footprint for the area, so buyers should expect the size of the house to carry more of the value conversation than any shared clubhouse or gate.
Nearby homes for sale
No active listings inside Stillwater Xing Prcl Sc-13 Ph 1 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
A compact, single-phase Windermere community of 60 homes built primarily in the 2006-2016 window, with larger living areas and no listed community amenities to factor into value.
Stellar MLS sales records identify 5 homes in Stillwater Crossing that have changed hands since 2017, built between 2014 and 2014 (median 2014), with a median living area of about 2,909 sq ft and a typical 4-bedroom, 3.5-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
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 Stillwater Crossing is best for.
Best for
- Buyers prioritizing larger living space over community amenities
- Buyers comfortable navigating a small resale pool with limited comps
- Buyers looking for a single-phase community with a relatively consistent construction era
Probably not for
- Buyers who want on-site amenities like a pool or clubhouse included
- Buyers who need a wide, deep resale market with frequent listing turnover
- Buyers set on a much newer build than the 2006-2016 window here
The market around Stillwater Crossing
Stillwater Crossing is too small for its own price trend, so here is the market around it.
In ZIP 34786, 336 homes are on the market and 26% are under contract — a steady corner of Windermere.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 34786 (Windermere), 788 homes closed in the last 12 months at a median of $640K ($261/sq ft), down 0.6% year over year, with a median 40 days on market. Right now 131 active and 43 pending listings put supply at about 3.7 months — a balanced market. See the live ZIP 34786 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Stillwater Crossing specifically. Momentum Research analysis of MLS records.
The Stillwater Crossing buying strategy.
If we were buying in Stillwater Crossing 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 Stillwater Crossing.
A Size-First Market
Because Stillwater Crossing Ph 1 doesn't carry MLS-identified community amenities, the appeal here is structural rather than lifestyle-driven. Buyers are shopping square footage, layout, and lot, not a gate or a fitness room. With a median living area near 2,964 square feet, homes in this community tend to skew toward larger floor plans relative to what's typical in many surrounding subdivisions, which matters for anyone comparing this pocket against amenity-heavy neighborhoods nearby.
The homestead share sits at 61.7%, meaning a majority of homes here are owner-occupied as primary residences rather than held as investment or secondary property. That tends to support more consistent upkeep and a steadier resale rhythm, though with only 60 homes total, inventory can be thin and any given listing may carry outsized weight in how the market reads at a given moment.
The location and the amenities are priced into every listing in Stillwater Crossing. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, single-phase community like this, comparables are limited and every closed sale matters more than it would in a larger subdivision. We track this pocket of Windermere closely enough to know which recent sales are true comps and which are outliers driven by condition or updates, so you're not pricing off a listing that doesn't reflect what's actually on the ground.
Stillwater Crossing 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 Stillwater Crossing 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 Stillwater Crossing sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Stillwater Crossing, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Stillwater Crossing home worth?
Get a no-obligation home value based on real comparable sales in Stillwater Crossing, 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 Windermere →
Should you buy in Stillwater Crossing?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2017 (4 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 local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Stillwater Crossing Ph 1 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Stillwater Crossing
Where is Stillwater Crossing?
Stillwater Crossing is a community in Windermere, Orange County, Florida, ZIP 34786.
Are there homes for sale in Stillwater Crossing right now?
No active listings inside Stillwater Crossing at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Stillwater Crossing have an HOA or CDD?
No HOA is on record for Stillwater Crossing 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.
Nearby Communities
Explore more neighborhoods near Stillwater Crossing with Momentum Realty’s local guides.