3739 Winding Lake Circle, Orlando, FL 32835
Sources: Stellar MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
As of October 5, 2026, 3739 Winding Lake Circle in Cypress Landing Ph 02, Orlando is listed at $934,000 (3,404 sq ft, about $274 per sq ft). It has been 36 days on market. Listing facts: built in 1997, a private pool, HOA dues of $60/mo. Figures are from the MLS record and county data; deemed reliable but not guaranteed.
- No CDD assessment on record
- Built 1997 · 29 yrs
- 3,404 sq ft of living area
- 3-car garage
- Listed at $934,000 — recent neighborhood median sale price ~$870,000 (nearby sales; deemed reliable, not an appraisal)
- 36 days on market
- HOA $60/mo (per listing)
About this home
BRAND NEW ROOF. NEW ENERGY-EFFICIENT, DOUBLE PANE WINDOWS. And they're being installed before closing, giving the you peace of mind knowing two of the most important and expensive components of a Florida home are already being taken care of.
The new roof includes a transferable GAF registered Silver Pledge 10 year workmanship warranty and 50 year manufacturer warranty including 15 year infinite wind speed protection, while the new double pane windows offer an all inclusive transferable lifetime warranty. Together, these upgrades can help reduce heat transfer into the home, ease the workload on your air conditioning system, and potentially lower electric costs an especially valuable benefit in Central Florida. Now, add a beautifully updated pool home in highly sought-after Cypress Landing, and you have an opportunity that's hard to overlook.
Situated on an oversized lot with peaceful green space behind it, this home offers the privacy of no rear neighbors while providing plenty of space for family, guests, and everyday living. Inside, you'll find four bedrooms, a dedicated office that can easily function as a fifth bedroom, three full bathrooms, and a versatile upstairs bonus room. The bright, open floor plan features soaring ceilings, formal living and dining rooms, and a spacious family room anchored by a cozy wood burning fireplace.
The three-way split floor plan provides excellent separation and privacy. The kitchen features granite countertops, decorative tile backsplash, abundant cabinetry, stainless steel appliances, and generous prep space. The primary suite provides a relaxing retreat with a spa inspired bathroom and soaking tub.
Then step outside, where the Florida lifestyle really comes to life. The expansive screened lanai overlooks a custom pool and spa, creating an ideal setting for entertaining, relaxing, or simply enjoying beautiful Florida evenings. And the location is tough to beat.
Windy Ridge K–8 School is within walking distance, Universal Studios is approximately eight minutes away, Restaurant Row is about 10 minutes away, and Walt Disney World and SeaWorld are roughly 20 minutes from home. Schedule your private showing today!
All 6 photos
Description provided by EXP REALTY LLC 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 $5,112/mo 75%
- Taxes $1,229/mo 18%
- Insurance $435/mo 6%
- HOA $60/mo 1%
$6,836/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.
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.
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 Cypress Landing Orlando market
How this home is priced against recent nearby sales, and where Cypress Landing Orlando has been over 25 years. Momentum Research analysis of realMLS 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.
This home’s history
- 1997BuiltPer public record
- About Aug 2026Listed (per MLS)MLS reports 36 cumulative days on market as of October 5, 2026
- Oct 1, 2026First seen on movewithmomentum.comObserved at $934,000
- NowUnder contractCurrently pending
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
4 closed sales in CYPRESS LANDING PH 02 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 4 sales: $870,000 ($274/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 — 4 comparable closed sales in CYPRESS LANDING PH 02, closed within the last 18 months, same property type, living area within 30% of this home.
Actual list price: $934,000 — compare it against the range above. The Messtimate is a blind sqft estimate; the list price reflects this specific home.
A 27% spread on the same house — and that gap is exactly what an automated guess can't see:
- Condition & updates — a 1997 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 — one flip or distressed sale in the comps drags the whole $/sq ft up or down.
- Carrying costs & concessions — this home carries HOA dues of $60/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:
- 1 active listing competing, 2 under contract
- 11 closed here in the last 12 months
For reference, this home is listed at $934,000 ($274/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: 3,404 sq ft × $241–$307/sq ft (±12% around the median of 4 comparable closed sales in CYPRESS LANDING PH 02, last 18 months; MLS closed-sale records). Estimate for general information only; not an appraisal, valuation, or offer. Updated October 5, 2026.
The Momentum read
🟠 Seller-leaning conditions around this listing. 1.1 months of supply in the surrounding market and 36 days on market for this home, against a 36-day area median.Days on market:this home 36Area median: 36 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. Source: Data provided by realMLS. As of August 23, 2026.
🟡 Asking $274 per square foot, about in line with the community’s $274 median. Cypress Landing Orlando’s 12-month median sold price per square foot is $274. MLS facts: Stellar MLS closed sales. A per-square-foot gap is context, not an appraisal; condition, lot, and view set the final number here.
What’s unique here: 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 EXP REALTY LLC · MLS # O6426943
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More on CYPRESS LANDING PH 02
Go deeper on CYPRESS LANDING PH 02
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 3739 Winding Lake Circle, chosen from what the record shows. This is general guidance, not advice about this specific property.
- Built in 1997 (29 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 $60/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 3,404 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 $14,750/yr) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $8,425 more per year than the current owner’s estimated bill (+133%). 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 in CYPRESS LANDING PH 02, last 18 months, as of August 23, 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 3739 Winding Lake Circle and when was it built?
Per the listing record, 3739 Winding Lake Circle was built in 1997 and has 3,404 sq ft of living area, 4 bedrooms and 3.0 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 3739 Winding Lake Circle in?
3739 Winding Lake Circle is in Cypress Landing Ph 02 in Orlando, Orange County. The comparable-sales section on this page shows recent closed sales nearby from the same MLS data.
Does 3739 Winding Lake Circle have an HOA, and how much are the dues?
The listing reports HOA dues of $60 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 3739 Winding Lake Circle differ from the current owner's?
The estimate on this page (about $14,750 per year) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $8,425 more per year than the current owner’s estimated bill (+133%). 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 3739 Winding Lake Circle 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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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.
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.