Front elevation5373 Isleworth Country Club Drive, Windermere, FL 34786
Sources: Stellar MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
As of September 20, 2026, 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 came to market within the past week. 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)
- New to market
- HOA $1,224/mo (per listing)
Pricing & the Isleworth Windermere market
How this home is priced against recent nearby sales, and where Isleworth Windermere 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 Windermere
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
- NowActiveCurrently for sale
Build year is from public record. Listing 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.
Estimated monthly payment
- Principal & interest $38,128/mo 77%
- Taxes $6,300/mo 13%
- Insurance $3,805/mo 8%
- HOA $1,224/mo 2%
$49,457/mo at 20% down, 30-yr @ 6.95% · edit any field to update.
Editable estimate — not a loan offer. Estimates only; see data & estimate notes.
Momentum Property Score
36/100 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.
Momentum Scores are objective, rules-based indicators computed from listing facts, public records, and recent nearby sales. 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 1 days on market for this home, against a 18-day area median.Days on market:this home 1Area 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 Windermere’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 Windermere 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 Windermere 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 Windermere, no CDD assessment.
Jump to: About this home · Every number, sourced · Monthly cost · Flood & risk · History · FAQ
Updated September 20, 2026 · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
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.
Description provided by STOCKWORTH REALTY GROUP and reproduced from the MLS; not independently verified.
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
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
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.
Actual list price: $7,200,000 — compare it against the range above. The Messtimate is a blind sqft estimate; the list price reflects this specific home.
A 22% spread on the same house — and that gap is exactly what an automated guess can't see:
- Condition & updates — a 1988 home may have had its roof, kitchen, or HVAC replaced since, or not; sq ft can't see either.
- 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 $1,224/mo; with insurance and any seller-paid buydown, that changes what a buyer actually pays, and a sq ft estimate ignores all of it.
- The pool — a private pool carries cost and value that living area doesn't capture.
And here's what the live market is doing — which the number above ignores entirely:
- This home: 1 days on market vs. a 18-day community median
- 19 active listings competing, 3 under contract
- ≈15.2 months of supply
- 15 closed here in the last 12 months
For reference, this home is listed at $7,200,000 ($1,201/sq ft) — a number set with analysis a Messtimate can't do.
Selling your own home? Try the Messtimate on your address →
Methodology: 5,993 sq ft × $632–$769/sq ft from recent nearby closed sales (public records). Estimate for general information only; not an appraisal, valuation, or offer. Updated September 20, 2026.
Similar homes for sale near ISLEWORTH
Active listings nearby at a comparable size and price. Listings held by brokerages other than Momentum Realty are marked with the listing broker. Deemed reliable but not guaranteed.
Newest listings in ISLEWORTH
- 5524 Worsham Court · $3,500,000 · 4 bd / 6.0 ba · listed September 11, 2026 (courtesy of ATLIS REALTY GROUP LLC)
- 9921 Lake Louise Drive · $6,650,000 · 5 bd / 6.0 ba · listed September 5, 2026 (courtesy of ISLEWORTH REALTY LLC)
Recently off market in ISLEWORTH
- 9921 Lake Louise Drive · 2026-09-10
- 9725 Chestnut Ridge Drive · 2026-09-10
- 9648 Mccormick Place · 2026-09-10
- 9144 Isleworth Gardens Drive · 2026-09-10
- 5524 Worsham Court · 2026-09-10
- 5237 Isleworth Country Club Drive · 2026-09-10
Price & listing history
Building permits
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.
This is a coastal Florida county. Premiums and coverage vary by home; obtain a quote from a licensed insurer.
Internet & broadband
AT&T Fiber covers much of NE Florida; confirm availability at the address.
Xfinity/Spectrum cable broadband is widely available.
T-Mobile / Verizon fixed-wireless as a backup option.
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Listed by STOCKWORTH REALTY GROUP · MLS # O6439156
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Recent sales activity in ISLEWORTH
Recent comparable closed sales near this home, from public records. Summary figures are for general reference only and are not a valuation of this property. See the ISLEWORTH neighborhood guide for more.
Recent nearby closings in the data set.
Canonical 12-month median closed price. Reference only.
Canonical 12-month median $/sq ft. Reference only.
Go deeper on ISLEWORTH
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 →
Comparable recent sales
Recent closed sales nearby, with photos, so you can compare. Sold prices are public record, deemed reliable but not guaranteed.
Community 12-month median: $743/sq ft. Shown for general reference only — this is not an appraisal or a statement of this home's value. Sold prices are public record and deemed reliable but not guaranteed.
Investment snapshot
Objective rental and cash-flow estimates for a buyer weighing this as an investment. Rough figures for general information only — not a guarantee of rent, an appraisal, or investment advice. Verify independently.
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 $75,600/yr) assumes reassessment at the list price; the seller's homestead cap does not transfer, so their current bill is not a guide.
- School zoning shown here comes from district data and changes; confirm the assigned schools directly with the district before relying on them.
Approximate distances
Approximate drive times for general reference only.
Data sources & freshness
| Listing record | Stellar MLS, refreshed twice daily (last: September 20, 2026) |
| Community market stats | Stellar MLS closed sales, as of September 20, 2026 |
| Flood zone & elevation | Not verified for this address — look it up at msc.fema.gov |
| Taxes & monthly cost | Estimated from county rates; not a quote |
| 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 community section on this page shows recent closed sales, days on market, and active inventory for Isleworth 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 $75,600 per year) assumes reassessment at the list price. Florida's Save Our Homes rule caps annual assessment increases for homesteaded owners, and the assessment resets after a sale, so a new owner's bill may differ from the seller's. 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.
See 5373 ISLEWORTH COUNTRY CLUB DRIVE in person
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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 a typical county millage rate to the list price 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.
Found an error? If you are the owner, listing agent, or a party to this property and believe any information is inaccurate, email and we will review and correct or remove it promptly.
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.