1329 Windsor Drive, Kissimmee, FL 34741
Sources: Stellar MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
As of October 5, 2026, 1329 Windsor Drive in Windsor Pines 1 Condo, Kissimmee is listed at $130,000 (1,290 sq ft, about $101 per sq ft). It has been 99 days on market. Listing facts: built in 1982, HOA dues of $375/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 1982 · 44 yrs
- 1,290 sq ft of living area
- Listed at $130,000 — recent neighborhood median sale price ~$222,500 (nearby sales; deemed reliable, not an appraisal)
- 99 days on market
- HOA $375/mo (per listing)
About this home
Under contract-accepting backup offers. Two stories, two bedrooms, two and a half baths, with the boring expensive stuff already handled. NEW roof overhead, NEW AC, NEW hot water heater, special assessment already paid, NEW living room flooring downstairs, NEW carpet up, and FRESH paint throughout.
The first floor opens into a foyer that gives way to a full dining room on one side and a kitchen with breakfast bar seating on the other, both flanking a living room that stretches to back sliders. A second set of sliders off the front leads to a private patio, so you get cross-breeze and two outdoor spots before you even head upstairs. A half bath sits tucked off the kitchen for guests.
Upstairs holds two true primary suites, each with its own full bathroom and its own private balcony. One faces the front, one faces the back, both have walk-in closets, and the laundry closet lives upstairs where the laundry actually is. Windsor Pines comes with a community pool and a playground, and the location does the rest of the work.
You're a few minutes from The Loop, where the grocery run, the dinner reservation, and the movie all happen in one parking lot. Ten minutes to downtown Kissimmee and the lakefront, straight onto Osceola Parkway or the Turnpike when you need to be elsewhere, and about fifteen minutes from the Disney gates when you don't. Two primaries.
Two porches. Two private balconies. One opportunity.
Description provided by SERHANT 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 $712/mo 57%
- Taxes $102/mo 8%
- Insurance $70/mo 6%
- HOA $375/mo 30%
$1,259/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 tax roll · county-average rateProperty 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: Florida TaxWatch 2025 How Florida Counties Compare (county-average millage); school portion estimated at ~42% of total, capped at 6.50 mills. 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 Osceola County, FL: overall Relatively Moderate. 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 Windsor Pines 1 Condo market
How this home is priced against recent nearby sales, and where Windsor Pines 1 Condo 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.
This home’s history
- 1982BuiltPer public record
- About Jun 2026Listed (per MLS)MLS reports 99 cumulative days on market as of October 5, 2026
- Jul 10, 2026First seen on movewithmomentum.comObserved at $175,000
- Sep 16, 2026Price cut$130,000 (-$45,000, -25.7%)
- 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: $222,500 ($172/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: $130,000 — compare it against the range above. The Messtimate is a blind sqft estimate; the list price reflects this specific home.
A 5% spread on the same house — and that gap is exactly what an automated guess can't see:
- Condition & updates — a 1982 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 $375/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:
- 0 active listings competing, 1 under contract
For reference, this home is listed at $130,000 ($101/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: 1,290 sq ft × $166–$175/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
88/100 is exceptional 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: 4 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
🟡 Asking $101 per square foot, about 41% below the community’s $172 median. Windsor Pines 1 Condo’s 12-month median sold price per square foot is $172. 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 SERHANT · MLS # O6403991
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More on WINDSOR PINES 1 CONDO
Go deeper on WINDSOR PINES 1 CONDO
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 Osceola 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 1329 Windsor Drive, chosen from what the record shows. This is general guidance, not advice about this specific property.
- Built in 1982 (44 years): ask for the roof and HVAC replacement dates — insurers commonly ask for roof age on homes this old, and it changes the premium.
- Condominium: request the association's budget, reserves, the most recent milestone or structural inspection report, and two years of meeting minutes before relying on the dues.
- 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 Osceola County; a wind-mitigation inspection and, on older homes, a four-point inspection can change the premium.
- Listed living area is 1,290 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 $1,225/yr) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $650 more per year than the current owner’s estimated bill (+113%). 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 1329 Windsor Drive and when was it built?
Per the listing record, 1329 Windsor Drive was built in 1982 and has 1,290 sq ft of living area, 2 bedrooms and 2.5 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 1329 Windsor Drive in?
1329 Windsor Drive is in Windsor Pines 1 Condo in Kissimmee, Osceola County. The comparable-sales section on this page shows recent closed sales nearby from the same MLS data.
Does 1329 Windsor Drive have an HOA, and how much are the dues?
The listing reports HOA dues of $375 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 1329 Windsor Drive differ from the current owner's?
The estimate on this page (about $1,225 per year) assumes reassessment at the list price less the homestead exemption. Estimated buyer taxes are about $650 more per year than the current owner’s estimated bill (+113%). 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 1329 Windsor 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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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.