16 days on market Single Family Residence
$1,550,000

1421 CHAPMAN CIRCLE, WINTER PARK, FL 32789

Single Family Residence in WINDSONG ELIZABETHS WALK 43/81, WINTER PARK · No CDD · FEMA Zone X
WINDSONG ELIZABETHS WALK 43/81 · WINTER PARK, FL 32789 · Orange
Listing data updated July 8, 2026 · refreshed twice daily
4Bedrooms
3.5Bathrooms
3,578Sq Ft
2005Year Built
$433Per Sq Ft
2-car garageNo CDDFEMA Zone X4 bedrooms
Highlights
  • No CDD assessment on record
  • FEMA Zone X — flood insurance generally not federally required
  • Built 2005 · 21 yrs
  • 3,578 sq ft of living area
  • 2-car garage
  • $433/sq ft — compared with the displayed median of $433 from recent nearby sales
  • 16 days on market
  • HOA ~$50/mo (estimate; confirm)

This listing is shown at $1,550,000, with 4 bedrooms and 3.5 bathrooms, and 3,578 square feet. The page displays an estimated monthly payment, FEMA flood-zone information, estimated ownership costs, a source-tagged Momentum Fact Check, and recent comparable-sale data where available. All estimates should be independently verified.

Momentum Snapshot

The whole picture, at a glance

Property

Bedrooms4
Bathrooms3.5
Living area3,578 sq ft
Year built2005
Property typeSingle Family Residence

Financial

Est. monthly payment$10,125
Est. taxes / yr~$16,275
Est. insurance / yr~$7,617
HOA$50/mo
CDDNone on record
Price / sq ft$433

Risk

Flood zoneZone X · minimal hazard (FEMA)
Ground elevation~20 ft
Wind exposureCoastal — obtain a quote
Insurance (est.)~$7,617/yr

Market

Days on market16
Neighborhood median DOM16
Active listings (area)1
Comparable-sales median$1,550,000

Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.

Visual snapshot

The numbers, at a glance

Flood risk
Zone X
Minimal hazard, outside the SFHA per FEMA
Est. insurance
~$7,617/yr
Estimated homeowners premium; get a real quote.

Estimated monthly payment

$10,125/mo
  • Principal & interest $8,084/mo 80%
  • Taxes $1,356/mo 13%
  • Insurance $635/mo 6%
  • HOA $50/mo 0%

Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.

Momentum Scores

Momentum Property Score

63/100
Strongest on: Flood safety (95), Market liquidity (87)

A rules-based composite of the objective indicators below — each computed from listing facts, public records, and recent nearby sales, not opinion.

How to read it: a higher score means more of these objective measures line up in a buyer’s favor — for example, priced competitively against recent nearby sales, lower carrying costs, or lower flood risk. A lower score means fewer do. It reflects only the indicators below — not the home’s quality, condition, or desirability, and nothing about who should live there.

Price vs area50
This home $433/sq ft vs area median $433/sq ft from recent nearby sales.
Affordability50
List price $1,550,000 vs area median $1,550,000. Not a measure of personal affordability.
Flood safety95
FEMA Zone X, ~20 ft elevation. Verify the parcel with FEMA.
Insurance cost72
From FEMA Zone X and a 2005 build. Obtain a property-specific quote.
Market liquidity87
Area median 16 days on market.
Renovation upside23
From a 2005 build and $433/sq ft vs area $433/sq ft. Not a condition assessment.

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.

Listing facts & disclosures
$1,550,000
List price
As listed in the MLS
4 / 3.5
Bed / bath
Per the listing
3,578
Living area
Sq ft (approx.)
$433
Price / sq ft
List ÷ living area

The home

Year built2005
Per public record.
Property typeSingle Family Residence
Per the listing.

Costs

HOA$50/mo
Disclosure — confirm exact dues and inclusions.
CDD assessmentNone on record
Estimate/disclosure — confirm the parcel's actual CDD with the county.
Est. first-year tax~$16,275/yr
Opinion/estimate at typical county millage — your assessed bill will differ. Do not rely on this.

Site & risk

FEMA flood zoneZone X · minimal hazard (FEMA)
From the FEMA flood map; verify the parcel.
Ground elevation~20 ft
Approximate parcel elevation (USGS).
WindstormLow
Coastal exposure varies; obtain an insurer quote.

Please note. Figures such as estimated taxes, insurance, CDD/HOA amounts, payments, and any market or comparable-sales summary are opinions and estimates for general information only, may be inaccurate, are not appraisals or advice, and should not be relied upon. Verify everything independently before making any decision.

Listing courtesy of KELLY PRICE & COMPANY LLC · Listing agent: Kelly Price · 407-645-4321Provided 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™

The Messtimate: $1,363,218 – $1,735,330

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.

$1,363,218the mess$1,735,330

Actual list price: $1,550,000 — 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 renovated kitchen, new roof, or older interior finishes can swing value six figures. Sq ft can't see it.
  • The lot — a premium waterfront, conservation, or cul-de-sac lot vs. a road-facing one: same sq ft, very different price.
  • Outliers skew it — one flip or one distressed sale in the comps drags the whole $/sq ft up or down.
  • Layout & beds/baths — two homes at 2,000 sq ft with 3/2 vs. 4/3 don't sell for the same number.
  • Views & orientation — golf, water, or preserve views aren't in the square footage.
  • Upgrades & systems — solar, pool, impact windows, new HVAC: real money, invisible to a calculator.
  • Unpermitted or mismeasured sq ft — public records are often wrong, and unpermitted additions don't count.
  • Carrying costs — CDD bonds, HOA dues, and flood-zone insurance change what a buyer will actually pay.
  • Timing & concessions — the market moves monthly, and seller-paid rate buydowns hide the true price.
  • School zoning & micro-location — one street over can mean a different school, and a different price.

And here's what the live market is doing — which the number above ignores entirely:

  • This home: 16 days on market vs. a ~16-day neighborhood median
  • 1 active listing competing in WINDSONG ELIZABETHS WALK 43/81
  • 0% of for-sale inventory is currently under contract (under contract + pending, as a share of all for-sale inventory)

For reference, this home is listed at $1,550,000 ($433/sq ft) — a number set with analysis a Messtimate can't do.

Want a property-specific review from a licensed agent? A Momentum Realty agent will do a real, free comparative market analysis — walking the home, the lot, the condition, and the live market. That's the difference between a Messtimate and a valuation.

Selling your own home? Try the Messtimate on your address →

Methodology: 3,578 sq ft × $381–$485/sq ft from recent nearby closed sales (public records). Estimate for general information only; not an appraisal, valuation, or offer. Updated July 8, 2026.

Property timeline

This home’s history

  • 2005BuiltPer 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.

If you rent it out

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.

Estimated rent$7,104 – $10,333/moa rough gross-rent-yield range on list price (comp-based estimate coming).
Estimated cap rate4.5%Net operating income ÷ list price; excludes financing.
Est. monthly cash flow−$3,226 – −$320At 25% down, 30-yr; after a 10% vacancy/maintenance/management reserve.
Momentum Fact Check

Every number, sourced

We separate what is listing data, what comes from public records, what we calculate or estimate, and what a buyer should verify. Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.

Listing facts MLS

List price$1,550,000
Bed / bath4 / 3.5
Living area3,578 sq ft
Year built2005
Property typeSingle Family Residence
MLS #O6415941
Listing status16 days on market
Days on market16

Public records & third-party data

FEMA flood zoneZone X
Ground elevation~20 ft
CountyOrange
Estimated first-year tax~$16,275/yr
CDD assessmentNone on record
HOA (estimate)$50/mo

Calculated estimates

Price per sq ft$433
Estimated monthly payment$10,125
Estimated insurance~$7,617/yr
Messtimate rangeNot available on this page
Comparable-sales median$1,550,000

Buyer should verify Buyer verify

Exact HOA dues, fees, and restrictionsRoof age and conditionHVAC age and conditionA property-specific insurance quoteSurvey and lot boundariesPermit historyFlood-insurance requirementsSchool zoning (confirm with the district)Property taxes after sale (homestead reset)CDD / community assessmentsSquare footage and room dimensions
No surprises at closing

Estimate a monthly payment

A tool to estimate a monthly payment. All values are editable estimates, not a loan offer or a statement about this property. Property tax, insurance, CDD, and HOA figures are approximations — verify each independently.

Estimated monthly payment
$10,125
Principal & interest$8,084
Property tax$1,356
Insurance$635
CDD assessment$0
HOA$50
PMI$0

Down payment $310,000 · Loan $1,240,000. Estimate only — not a loan offer. We'll connect you with a local lender for an exact quote.

Estimated ownership costs

Estimated costs & disclosures

Estimates and disclosures for general information only. These are opinions/approximations, not guarantees, and should not be relied upon — confirm every figure with the county, your lender, and an insurer.

Property tax reset
~$16,275/yr

The seller likely pays less due to the homestead cap. At a $1,550,000 purchase, expect your first full-year Orange bill near $16,275 before exemptions.

CDD assessment
None

No CDD assessment on record for this community.

Insurance
~$7,617/yr

Estimate for a 2005 build in Orange. Newer construction and wind-mitigation features lower premiums. Flood not mandated (Zone X).

HOA
$50/mo

Covers the master association & common areas. Confirm exact dues and what they include.

Environmental data

Flood zone & elevation

Sourced environmental data for the parcel. Confirm with FEMA and your insurer.

FEMA flood zone
Zone X

From the FEMA National Flood Hazard Layer. In this zone lender-required flood insurance is generally not mandated; confirm for the parcel.

Ground elevation
~20 ft

Approximate parcel elevation from USGS. Run --online for a live reading.

Windstorm / insurance
Obtain a quote

This is a coastal Florida county. Premiums and coverage vary by home; obtain a quote from a licensed insurer.

Market data · public records

Recent sales activity in WINDSONG ELIZABETHS WALK 43/81

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 WINDSONG ELIZABETHS WALK 43/81 neighborhood guide for more.

Comparable sales found
0

Recent nearby closings in the data set.

Median sale price (set)
$1,550,000

Median closed price of the comparable set. Reference only.

Median $/sq ft (set)
$433

Median $/sq ft of the comparable set. Reference only.

This home $/sq ft
$433

List price divided by living area. Provided as data, not a value judgment.

Go deeper on WINDSONG ELIZABETHS WALK 43/81

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

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.

Brookshire ElemAssigned elementary school · Orange County School District
Glenridge MiddleAssigned middle school · Orange County School District
Winter Park HighAssigned high school · Orange County School District
How it stacks up

Comparable recent sales

Recent closed sales nearby, with photos, so you can compare. Sold prices are public record, deemed reliable but not guaranteed.

No closely comparable recent sales were found in this data set.

Keep looking

Similar homes for sale near WINDSONG ELIZABETHS WALK 43/81

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.

Before you decide

Buyer research checklist

A neutral list of items to confirm for any home. This is general guidance, not advice about this specific property.

  • Confirm roof age and condition during inspection.
  • Confirm HVAC age and condition during inspection.
  • Request current HOA documents before relying on dues or restrictions.
  • Obtain an insurance quote for this specific property.
  • Confirm school zoning directly with the district.
  • Order a survey to confirm lot boundaries.
  • Review permit history with the county.
  • Confirm whether flood insurance is required for this parcel.
  • Confirm square footage and room dimensions independently.
  • Ask the county how property taxes may change after a sale.
Listing description

About this home

Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. Spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. The gourmet kitchen is the heart of the home, featuring granite countertops, premium Thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through French doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true Florida fashion. The first-floor primary suite is a private retreat, complete with French door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two HVAC units, both dated 2017. Beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for A-rated schools and ideally situated just minutes from the vibrant energy of Baldwin Park, Audubon Park, the Mills District, Downtown Orlando, and all that Winter Park has to offer, this address places you at the center of everything. Whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 Chapman Circle is a rare find in one of Central Florida's most beloved neighborhoods.

Description provided by KELLY PRICE & COMPANY LLC and reproduced from the MLS; not independently verified.

The full spec sheet

Property details & features

Interior

  • Bedrooms4
  • Bathrooms3.5
  • Living area3,578 sq ft

Exterior & lot

  • TypeSingle Family Residence

Systems

  • Year built2005
  • Age21 yrs

Listing

  • MLS #O6415941
  • StatusActive
  • Days on market16
Nearby & commute

Approximate distances

Approximate drive times for general reference only.

Connectivity

Internet & broadband

Fiber
Check availability

AT&T Fiber covers much of NE Florida. Run --online or confirm at the address.

Cable
Likely

Xfinity/Spectrum cable broadband is widely available.

5G Home
Backup

T-Mobile / Verizon fixed-wireless as a backup option.

Transparency

Price & listing history

Listed for $1,550,000Momentum Realty · on market 16 days
Public records

Building permits

Permit history not yet linkedAdd county permit records via overrides
Answered before you ask

Frequently asked questions

Why might my property taxes differ from the current owner's?

Florida's Save Our Homes rule caps annual assessment increases for homesteaded owners, and the assessment can be re-set after a sale. As a result 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.

Where does the flood-zone information come from?

The flood designation shown (Zone X) comes from the FEMA flood map and is provided for general information. 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.

Ready when you are

See 1421 CHAPMAN CIRCLE in person

Private tours available 7 days a week, in person or by live video walkthrough. Request a tour or send a question and a licensed Momentum Realty agent will follow up.

Momentum Realty · licensed in FL & GA

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.

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.