8316 Lookout Pointe Drive, Windermere, FL 34786
Sources: Stellar MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
As of October 5, 2026, 8316 Lookout Pointe Drive in Windermere Trls Ph 3B, Windermere is listed at $1,075,000 (4,332 sq ft, about $248 per sq ft). That is 79% above Windermere Trls Ph 3B's median closed sale of $599,500 over the last 12 months (24 recorded sales). It has been 63 days on market. Listing facts: built in 2016, HOA dues of $8/mo. The parcel maps to FEMA flood zone X, outside the special flood hazard area. Figures are from the MLS record and county data; deemed reliable but not guaranteed.
- No CDD assessment on record
- Built 2016 · 10 yrs
- 4,332 sq ft of living area
- 2-car garage
- Listed at $1,075,000 — recent neighborhood median sale price ~$599,500 (nearby sales; deemed reliable, not an appraisal)
- 63 days on market
- HOA $8/mo (per listing)
About this home
Under contract-accepting backup offers. Fully Furnished- Located in the highly desirable Windermere Trails community, this impressive residence offers 5 bedrooms, 4 full bathrooms, a media room, loft, gym, and game room, providing plenty of space for both everyday living and entertaining. The home features elegant iron stair railings, formal living and dining areas, and an open-concept layout designed for comfort and functionality.
The gourmet kitchen showcases stainless steel appliances, a 36-inch cooktop, 42-inch cabinetry with crown molding, quartz countertops, upgraded backsplash, and a spacious walk-in pantry. The primary suite includes a large walk-in closet and a luxurious bathroom with dual vanities and a private water closet. An upgraded home theater with fiber-optic illuminated ceiling and wall panels creates a unique entertainment experience.
Step outside to enjoy a beautifully landscaped, fully fenced backyard with dual gate access, a tranquil water feature, and an extended covered lanai perfect for relaxing or entertaining. Residents enjoy access to community amenities including walking trails, a resort-style pool, playground, dog park, pavilions, and fitness areas. The property is being offered partially furnished, with many of the furnishings and features shown in the photos included in the sale.
All 74 photos
Description provided by LA ROSA REALTY KISSIMMEE and reproduced from the MLS; not independently verified.
Provided via the Stellar MLS Internet Data Exchange, as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID · Listings courtesy of Stellar MLS as distributed by MLS GRID. · deemed reliable but not guaranteedIDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed by the MLS to be accurate.Every fact, sourced
Listing data, public records, our calculations, and what to verify — each fact shown once. Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.
Listing facts MLS
Public records & third-party data
Calculated estimates
Buyer should verify Buyer verify
Estimated monthly payment
- Principal & interest $5,884/mo 77%
- Taxes $1,425/mo 19%
- Insurance $357/mo 5%
- HOA $8/mo 0%
$7,675/mo at 20% down, 30-yr @ 7.28% · edit any field to update.
Editable estimate — not a loan offer. Estimates only; see data & estimate notes.
Property taxes
✓ Certified county tax rollProperty taxes in Florida are reassessed after a sale, so a buyer’s first full-year bill can be higher than the seller’s. Budget from this estimate, not the current bill, before you make an offer.
Most of this comes from Florida’s Save Our Homes assessment cap resetting when the home sells — the current owner’s protected assessment does not transfer to a new buyer.
Certified 2025 tax roll values for this parcel (Florida DOR). The roll gives values, not the bill; the current owner’s bill above is estimated from the taxable value.
Estimate my property taxes →Adjust for your exemptions, portability, and down payment
Sources: Florida DOR certified tax roll (2025), Stellar MLS; millage: Orange County Property Appraiser 2025 final millage rates; OCPS 2025-26 adopted budget. County public record, not MLS data — matched to this home by parcel ID. Estimates are not a tax bill; the county property appraiser and tax collector set the actual amount.
Flood zone & elevation
Sourced environmental data for the parcel. Confirm with FEMA and your insurer.
From the FEMA National Flood Hazard Layer. In this zone lender-required flood insurance is generally not mandated; confirm for the parcel.
Approximate parcel elevation from USGS; confirm exact elevation with a survey.
Premiums and coverage vary by home (roof age, wind mitigation, claims history); obtain a quote from a licensed insurer.
Natural hazard risk
FEMA National Risk Index for Orange County, FL: overall Relatively High. Ratings compare this county with every county in the United States for expected annual loss from each hazard.
Source: FEMA National Risk Index (county level, hazard risk ratings only). Ratings describe the county, not this parcel; the flood zone shown above is parcel-specific. Verify insurance requirements with your lender and agent.
Internet & broadband
Address-level fiber service is not confirmed for this home. Check the FCC National Broadband Map (broadbandmap.fcc.gov) or the provider for this address.
Cable broadband is common in Florida and Georgia towns but not confirmed for this address; verify with the provider.
5G home internet and satellite service depend on the exact location; check coverage for this address.
Pricing & the windermere trails market
How this home is priced against recent nearby sales, and where windermere trails has been over 25 years. Momentum Research analysis of Stellar MLS records; closed sales, deemed reliable but not guaranteed. Estimates only; see data notes.
This home’s $/sq ft vs. nearby sales
List $/sq ft against recent nearby closed sales; the community median is marked.
Price vs. size in windermere trails
Each dot is a closed sale since 2013 (336 total). This home is the gold marker.
Sale price (y) by living area in sq ft (x). Stellar MLS closed sales.
Median $/sq ft by year
Community sold $/sq ft, 2013–2026. This home lists at $248/sq ft.
Median sale price by year
12-month median closed price, 2013–2026.
Market Heat by year (0–100)
Momentum Market Heat, 2014–2026. Now 45 (normal).
This home’s history
- 2016BuiltPer public record
- Jul 10, 2026First seen on movewithmomentum.comObserved at $1,075,000
- NowActiveCurrently for sale
Build year is from public record. The MLS list date is approximate (today minus the cumulative days on market the MLS reports, which can span relistings). Other milestones reflect movewithmomentum.com’s own observations since we began tracking this listing and are not the MLS listing history; dates and prices are deemed reliable but not guaranteed.
Price & listing history
Building permits
Comparable recent sales
6 closed sales within about 3 miles in the last 18 months — same property type, living area within 30% of this home. Sold prices are MLS closed-sale records, deemed reliable but not guaranteed.
Median of these 6 sales: $599,500 ($243/sq ft). Stronger local evidence. Shown for general reference only — not an appraisal or a statement of this home’s value.
The Messtimate
This is a deliberately dumb estimate — living area times a range of recent neighborhood $/sq ft, and nothing else. It is not an appraisal, not market value, and not a valuation of this home. Even a tight range from comparable sales can’t price a specific home — here’s why.
Stronger local evidence — 6 comparable closed sales within about 3 miles, closed within the last 18 months, same property type, living area within 30% of this home.
Actual list price: $1,075,000 — compare it against the range above. The Messtimate is a blind sqft estimate; the list price reflects this specific home.
A 33% spread on the same house — and that gap is exactly what an automated guess can't see:
- Condition & updates — a renovated kitchen or new roof vs. dated finishes can swing value six figures; sq ft can't see it.
- The lot & views — a premium golf, water, or preserve lot vs. a road-facing one: same sq ft, very different price.
- Outliers skew it — the band above comes from 6 nearby sales; one flip or distressed sale moves the whole $/sq ft.
- Carrying costs & concessions — this home carries HOA dues of $8/mo; with insurance and any seller-paid buydown, that changes what a buyer actually pays, and a sq ft estimate ignores all of it.
And here's what the live market is doing — which the number above ignores entirely:
- This home: 63 days on market vs. a 51-day community median
- 10 active listings competing, 4 under contract
- ≈4.9 months of supply
- 27 closed here in the last 12 months
For reference, this home is listed at $1,075,000 ($248/sq ft). The list price is the seller's asking price and is not derived from this range.
Selling your own home? Try the Messtimate on your address →
Methodology: 4,332 sq ft × $287–$381/sq ft (interquartile band of 6 comparable closed sales within about 3 miles, last 18 months; MLS closed-sale records). Estimate for general information only; not an appraisal, valuation, or offer. Updated October 5, 2026.
Momentum Property Score
55/100 is solid, mid-pack across the objective indicators below. It reflects only those measures — not the home’s quality, condition, or desirability.
A 0-100 score built from objective property and market data: flood risk, insurance, pricing, supply, affordability, and recent sales. Higher means more measures line up in a buyer’s favor. It reflects only the factors below.
Coverage: 7 of 8 indicators had valid data for this home; indicators without data are left out, not scored as zero. Momentum Scores are objective, rules-based indicators computed from listing facts, public records, and recent comparable sales. They do not measure property condition, quality, or investment suitability, and they are not appraisals, valuations, investment advice, or judgments about a neighborhood or who should live there. Verify independently.
The Momentum read
🟡 Balanced conditions around this listing. 4.9 months of supply in the surrounding market and 63 days on market for this home, against a 51-day area median.Days on market:this home 63Area median: 51 daysWhy it matters: above-median time on market, together with the level of supply, is a clear sign of how much leverage sits with buyers.Momentum Research interpretation of the MLS facts in the snapshot above. Based on Stellar MLS data distributed by MLS GRID for the period 2013 through 2026. As of September 20, 2026.
🟡 Asking $248 per square foot, about in line with the community’s $243 median. windermere trails’s 12-month median sold price per square foot is $243. Median sold price per square foot is up 3.4% year over year. Confidence: High · 24 closed sales in 12 monthsMLS facts: Stellar MLS closed sales. A per-square-foot gap is context, not an appraisal; condition, lot, and view set the final number here.
50% of homes in windermere trails are owner-occupied. An estimated 50% are non-owner-occupied, including 11% held in a company or trust and 100% out-of-state owners.Why it matters: a high owner-occupied share typically means fewer rentals nearby and steadier resale demand.Source: Florida Department of Revenue 2025 assessment roll (public records), 412 homes matched. Community-level context.
Recent windermere trails sales closed near 95.6% of original asking.Why it matters: the community’s own record shows how far opening prices typically move, and how often buyers compete without financing.Momentum Research analysis of Stellar MLS records, community-level, 12 months ending September 20, 2026. Aggregates only; deemed reliable but not guaranteed.
What’s unique here: one of only 11 active listings in windermere trails, no CDD assessment.
Jump to: About this home · Every number, sourced · Monthly cost · Flood & risk · History · FAQ
Updated October 5, 2026 · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
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Listed by LA ROSA REALTY KISSIMMEE · MLS # S5152477
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Assigned schools
Schools currently assigned to this address in Orange County, provided as neutral factual data. Assignments can change — confirm current zoning with the school district. This is not a statement about the home's suitability for any person or family.
Assigned schools per the MLS listing — assignments can change; confirm current zoning with the district. Browse school-zone pages →
City, county & community guides
Where this home sits, with links to the matching guides. General reference only.
Buyer research checklist
Items worth confirming for 8316 Lookout Pointe Drive, chosen from what the record shows. This is general guidance, not advice about this specific property.
- Built in 2016: confirm the roof and HVAC install dates and whether any builder or manufacturer warranty transfers.
- HOA dues are listed at $8/mo: request the current budget, reserves, and rules before relying on that figure or on any restriction.
- FEMA flood zone X: flood insurance is not usually required, but get a quote anyway — FEMA reports roughly one in four flood claims come from outside high-risk zones.
- Get a homeowners insurance quote for this specific address in Orange County; a wind-mitigation inspection and, on older homes, a four-point inspection can change the premium.
- Listed living area is 4,332 sq ft: verify it against the property appraiser's record and measure before relying on it.
- Order a survey to confirm lot boundaries and easements.
- Review permit history with the county.
- Property taxes: the estimate on this page (about $17,100/yr) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $2,625 more per year than the current owner’s estimated bill (+18%). Exemptions and portability change the actual bill — confirm with the county property appraiser.
- School zoning shown here comes from district data and changes; confirm the assigned schools directly with the district before relying on them.
Data sources & freshness
| Listing record | Stellar MLS, refreshed hourly (last: October 5, 2026) |
| Comparable sales | Stellar MLS closed sales within about 3 miles, last 18 months, as of September 20, 2026 |
| Flood zone & elevation | FEMA flood maps + USGS elevation (Zone X shown above) |
| Taxes & monthly cost | Certified county tax roll (parcel-matched) × county millage; an estimate, not a bill |
| Insurance figure | Modeled estimate; obtain a real quote before offering |
| Schools | 2025-26 district assignments; verify with the district |
Momentum Research lines are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Estimates are informational, not appraisals or advice. Methodology: how Momentum scores are computed.
Frequently asked questions
How big is 8316 Lookout Pointe Drive and when was it built?
Per the listing record, 8316 Lookout Pointe Drive was built in 2016 and has 4,332 sq ft of living area, 5 bedrooms and 4.0 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 8316 Lookout Pointe Drive in?
8316 Lookout Pointe Drive is in Windermere Trls Ph 3B in Windermere, Orange County. The comparable-sales section on this page shows recent closed sales nearby from the same MLS data.
Does 8316 Lookout Pointe Drive have an HOA, and how much are the dues?
The listing reports HOA dues of $8 per month. Dues, what they cover, and the community's rules should be confirmed from the association's current documents before relying on them.
Why might property taxes on 8316 Lookout Pointe Drive differ from the current owner's?
The estimate on this page (about $17,100 per year) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $2,625 more per year than the current owner’s estimated bill (+18%). Florida reassesses a home after it sells; for a homesteaded seller the Save Our Homes cap on their assessment does not transfer, and a buyer's own exemptions and portability are applied separately, so the two bills usually differ. Any tax figure shown here is an estimate, not the actual bill — confirm with the county property appraiser and tax collector.
Is 8316 Lookout Pointe Drive in a flood zone?
The FEMA flood map places this parcel in Zone X, outside the special flood hazard area, so flood insurance is not usually required by a lender. It is still available and worth quoting; confirm the parcel's status with FEMA and your insurer.
Can I rely on the figures on this page?
No. Estimated taxes, insurance, payments, and any market or comparable-sales summary are opinions and estimates for general information only and should not be relied upon. Verify all information independently before making any decision.
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Opinion & estimate — do not rely on this page. Any figure on this page that is not a verbatim fact from the listing or a public record — including estimated property taxes, insurance, CDD/HOA amounts, mortgage payments, comparable-sales summaries, and market statistics — is an opinion and estimate provided for general informational purposes only. These figures may be inaccurate or out of date, are not appraisals, valuations, or financial, legal, tax, or investment advice, and should not be relied upon. Do not make any purchase, offer, financing, or other decision based on this page. Independently verify everything — price, square footage, lot size, year built, taxes, CDD/HOA, flood status, school assignments, permits, and community rules — with the listing broker, the county, your lender, a licensed inspector, an insurer, and your own advisors before acting.
Estimate methodology. Tax estimates apply county millage to the list price (less the homestead exemption where the parcel is matched to the certified roll) and will differ from the actual assessed bill. Cost and market figures are derived from available data and simple calculations, not a professional appraisal. We make no representation that any estimate reflects fair market value.
Equal Housing Opportunity. Content on this page is compiled from public records, MLS data, and automated sources and may contain errors or be out of date. It is general information only, not a representation about any specific property, community, builder, or association. Verify information independently before relying on it. Momentum Realty supports the Fair Housing Act and does not discriminate on the basis of race, color, religion, sex, handicap, familial status, national origin, sexual orientation, or gender identity. Information about schools, distances, and amenities is provided as neutral factual data to help you research the property and is not a statement about who should or should not live here or the suitability of the home or neighborhood for any person or group. School data may change — confirm current assignments with the school district.
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Automated content. Some summaries, distances, and estimates on this page are generated automatically from public and proprietary data sources and may contain errors or omissions. We strive for accuracy but cannot guarantee the completeness or accuracy of any information. Verify anything important independently.
No warranty; measurements & photos. No guarantee, warranty, or representation of any kind is made regarding the completeness or accuracy of any information, descriptions, or measurements on this page — including square-footage measurements and property condition — all of which should be independently verified through appropriate means, including in-person inspection and public records. Photographs may be virtually staged or digitally enhanced and may not reflect actual property conditions. Momentum Realty and its agents expressly disclaim any liability in connection with the information provided.
MLS / IDX. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Stellar MLS Internet Data Exchange, as distributed by MLS GRID. Real estate listings held by brokerage firms other than Momentum Realty are marked with the listing broker's name and include the name of the listing agent. Data provided is deemed reliable but is not guaranteed by the MLS to be accurate. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Source: Stellar MLS, as distributed by MLS GRID. Listings courtesy of Stellar MLS as distributed by MLS GRID. All rights reserved.
Listing data is deemed reliable but is not guaranteed and is subject to change or withdrawal without notice. Square footage and lot size are approximate. Real estate brokerage services provided by Momentum Realty, licensed in Florida and Georgia. © 2026 Move With Momentum LLC.