5373 Isleworth Country Club Drive, Windermere, FL 34786
Sources: Stellar MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
5373 Isleworth Country Club Drive in Isleworth, Windermere is listed at $7,200,000 (5,993 sq ft, about $1,201 per sq ft). That is 87% above Isleworth's median closed sale of $3,850,000 over the last 12 months (14 recorded sales). Per square foot it is above the community's recent $743/sq ft by about 62%. It has been listed Sep 9, 2026, longer than the community's typical 18 days to contract. Listing facts: built in 1988, a private pool, HOA dues of $1,224/mo. Figures are from the MLS record and county data; deemed reliable but not guaranteed.
- No CDD assessment on record
- Built 1988 · 38 yrs
- 5,993 sq ft of living area
- 3-car garage
- Listed at $7,200,000 — recent neighborhood median sale price ~$3,850,000 (nearby sales; deemed reliable, not an appraisal)
- listed Sep 9, 2026
- HOA $1,224/mo (per listing)
About this home
Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction.
A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel.
Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast.
Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style.
Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator.
The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional golf and social membership opportunities.
All 62 photos
Description provided by STOCKWORTH REALTY GROUP 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.The Messtimate
Our automated estimate of the likely sale-price range for this home — modeled from recent closed sales nearby adjusted to today's market, a local size-and-age model, and the county tax roll. It is an estimate, not an appraisal, not market value, and not an offer. A licensed agent's CMA sees the condition, the lot, and the live market that a model can't.
Strong local evidence — built from 14 comparable closed sales in ISLEWORTH (same property type, closed within the last 18 months, each adjusted to today's market).
Track record: across 2,796 recent closed sales we scored, the closed price landed inside the Messtimate range 56% of the time; median miss 9.2% (closed sales statewide, FL + GA feeds that permit an automated estimate). Re-scored weekly; last 2026-11-03.
Actual list price: $7,200,000 ($1,201/sq ft) — the seller's asking price is not an input to this range; compare the two.
A 22% spread on the same house — here is what a model can't see:
- Condition & updates — a 1988 home may have had its roof, kitchen, or HVAC replaced since, or not; the model can't see either.
- The lot & views — a premium golf, water, or preserve lot vs. a road-facing one.
- The pool — a private pool carries cost and value the model only sees through the comps.
- Carrying costs & concessions — this home carries HOA dues of $1,224/mo; insurance, CDD/HOA and seller-paid buydowns change what a buyer actually pays.
And what the live market is doing right now:
- This home: listed Sep 9, 2026 on market vs. a 18-day community median
- 20 active listings competing, 3 under contract
- ≈15.2 months of supply
- 12 closed here in the last 12 months
Selling your own home? Try the Messtimate on your address →
Methodology: 20th–80th percentile band combining time-adjusted $/sq ft of comparable closed sales (14) + tax-roll just value × local sale-to-roll ratio (1 sales, double weight); MLS closed-sale records and the FL DOR 2025 certified tax roll. Automated valuation model output for general information only — not an appraisal, not market value, not an offer, and not reviewed by a licensed appraiser. Updated November 3, 2026.
Comparable recent sales
6 closed sales in ISLEWORTH 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: $3,850,000 ($743/sq ft). Stronger local evidence. Shown for general reference only — not an appraisal or a statement of this home’s value.
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 $39,254/mo 72%
- Taxes $9,935/mo 18%
- Insurance $3,805/mo 7%
- HOA $1,224/mo 2%
$54,219/mo at 20% down, 30-yr @ 7.24% · 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.
The current owner’s taxable value is below today’s asking price; after a sale the assessment is set from market value, so the estimated bill is higher. Exemptions and portability can reduce it.
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.
What it really costs to own 5373 Isleworth Country Club Drive
The parts of the monthly number a mortgage calculator leaves out, from this listing's MLS record, the county tax roll, Citizens and FEMA. Property facts only.
| Property tax | The current owner's bill is about $43,850/yr (certified county roll, taxable value × millage). Buy at the asking price of $7,200,000 and the first-year bill resets to about $119,225/yr (the parcel is matched to the certified roll; asking price less the $50,000 homestead exemption × 16.67 mills); Save Our Homes caps later increases at 3%/yr. |
|---|---|
| HOA dues | $1,224/month per the listing record. Dues cover what the association documents say they cover; ask for the budget and reserve study before you close. |
| Home and flood insurance | The average Citizens Property Insurance premium in Orange County is $1,409/yr (4,204 policies, Citizens detail by county, April 2026); private-market quotes differ by roof age, wind mitigation and distance to the coast. The page's modeled range for this home is $32,000–$66,000/yr; neither is a quote. |
| Roof and age | Built in 1988. An original roof would be about 38 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 ask for the roof permit date. |
Estimated carrying cost at the asking price, before the mortgage: about $11,277/month (tax $9,935, HOA $1,224, insurance $117). An estimate from the sources above, not a quote; the monthly-cost calculator on this page adds the loan.
Flood zone & elevation
Sourced environmental data for the parcel. Confirm with FEMA and your insurer.
Not yet verified for this address. Look up the parcel at msc.fema.gov before relying on any flood assumption.
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.
County hazard risk ratings (FEMA National Risk Index, county level)
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 — how to check availability for this address
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 Isleworth market
How this home is priced against recent nearby sales, and where Isleworth 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 Isleworth
Each dot is a closed sale since 2004 (211 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, 2012–2026. This home lists at $1201/sq ft.
Median sale price by year
12-month median closed price, 2012–2026.
Market Heat by year (0–100)
Momentum Market Heat, 2013–2026. Now 55 (normal).
This home’s history
- 1988BuiltPer public record
- About Sep 2026Listed (per MLS)Approximate list date from the MLS cumulative days-on-market count (listed about Sep 9, 2026)
- Oct 2, 2026First seen on movewithmomentum.comObserved at $7,200,000
- 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
Momentum Property Score
34/100 is limited 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: 5 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
🟢 Buyer-leaning conditions around this listing. 15.2 months of supply in the surrounding market and 55 days on market for this home, against a 18-day area median.Days on market:this home 55Area median: 18 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 2004 through 2026. As of September 20, 2026.
🟡 Asking $1201 per square foot, about 62% above the community’s $743 median. Isleworth’s 12-month median sold price per square foot is $743. Median sold price per square foot is down 17.5% year over year. Confidence: Medium · 14 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.
52% of homes in Isleworth are owner-occupied. An estimated 48% are non-owner-occupied, including 27% 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), 151 homes matched. Community-level context.
Recent Isleworth sales closed near 92.3% 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 19 active listings in Isleworth, no CDD assessment.
Jump to: About this home · Every number, sourced · Monthly cost · Flood & risk · History · FAQ
Checked against the MLS November 4, 2026 · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
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Listed by STOCKWORTH REALTY GROUP · MLS # O6439156
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More on ISLEWORTH
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See schools, amenities, builders, HOA/CDD detail, and every active & sold home in the community — the single biggest advantage of buying here over a portal.
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 5373 Isleworth Country Club Drive, chosen from what the record shows. This is general guidance, not advice about this specific property.
- Built in 1988 (38 years): ask for the roof and HVAC replacement dates — insurers commonly ask for roof age on homes this old, and it changes the premium.
- HOA dues are listed at $1,224/mo: request the current budget, reserves, and rules before relying on that figure or on any restriction.
- Look up the parcel on FEMA's Flood Map Service Center and confirm with your insurer whether flood insurance is required.
- 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.
- Private pool: confirm the barrier or alarm meets the state residential pool safety code and ask for pump, heater, and resurfacing records.
- Listed living area is 5,993 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 $119,225/yr) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $75,375 more per year than the current owner’s estimated bill (+172%). 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, checked against the MLS hourly (last: November 4, 2026) |
| Comparable sales | Stellar MLS closed sales in ISLEWORTH, last 18 months, as of September 20, 2026 |
| Flood zone & elevation | Not verified for this address — look it up at msc.fema.gov |
| 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 5373 Isleworth Country Club Drive and when was it built?
Per the listing record, 5373 Isleworth Country Club Drive was built in 1988 and has 5,993 sq ft of living area, 5 bedrooms and 5.5 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 5373 Isleworth Country Club Drive in?
5373 Isleworth Country Club Drive is in Isleworth in Windermere, Orange County. The comparable-sales section on this page shows recent closed sales nearby from the same MLS data.
Does 5373 Isleworth Country Club Drive have an HOA, and how much are the dues?
The listing reports HOA dues of $1,224 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 5373 Isleworth Country Club Drive differ from the current owner's?
The estimate on this page (about $119,225 per year) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $75,375 more per year than the current owner’s estimated bill (+172%). 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 5373 Isleworth Country Club Drive in a flood zone?
A flood designation has not been verified for this address. Look up the parcel on FEMA's Flood Map Service Center (msc.fema.gov) and confirm with 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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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.
Found an error? If you are the owner, listing agent, or a party to this property and believe any information is inaccurate, email jon@movewithmomentum.com and we will review and correct or remove it promptly.
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. Florida real estate brokerage services provided by EAB RE Investments LLC dba Momentum Realty. Georgia real estate brokerage services provided by Momentum Realty LLC. Site designed by Move With Momentum LLC, © 2026.
Estimates, methodology & disclaimers
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.
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.