1421 CHAPMAN CIRCLE, WINTER PARK, FL, 32789
Active39 days on marketListed Jun 12, 2026MLS #O6415941
About this home
1421 CHAPMAN CIRCLE
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.
Facts & features
The home at a glance
4
Bedrooms
3.5
Bathrooms
3,578
Sqft
0.14 ac
Lot size
2
Garage
2005
Year built
Two
Levels
$405
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$9,679 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$9,679/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+6.8%
$/sqft vs Winter Park actives
$405 vs $348
Days on market
39 vs 34 typical
Where $405/sqft sits among the 318 Winter Park actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Windsong
Get to know Winter Park. See the full Winter Park guide →
Windsong — neighborhood snapshot
Population
714
Median age
57
Median income
$139,554
Median home value
$868,200
Avg household
2
Households w/ children
55%
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$473K → $500K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
141 of 318
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 71% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 1421 CHAPMAN CIRCLE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Apr ’26$1,850,000
1713 ELIZABETHS WALK · same community
4 bd · 4 ba · 3,670 sqft · $504/sqft · 0 DOM
Sold · Jun ’26$2,050,000
1636 ELIZABETHS WALK · same community
4 bd · 4.5 ba · 3,412 sqft · $601/sqft · 29 DOM
Sold · Mar ’26$1,475,000
1408 CHAPMAN CIRCLE · same community
4 bd · 4 ba · 3,237 sqft · $456/sqft · 81 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 1421 CHAPMAN CIRCLE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1421 CHAPMAN CIRCLE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
1421 CHAPMAN CIRCLE FAQs
What would the monthly payment be for 1421 CHAPMAN CIRCLE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $9,679/mo — principal and interest, the actual property-tax bill, the $268/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 1421 CHAPMAN CIRCLE?+
The association fee works out to $268 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 1421 CHAPMAN CIRCLE?+
The most recent tax bill on record (2025) was $10,592. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 1421 CHAPMAN CIRCLE?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Park?+
At $1,450,000, this home is listed about 131% above the Winter Park median of $627,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1421 CHAPMAN CIRCLE?+
Glenridge Middle (middle), Winter Park High (high), Brookshire Elementary (elementary) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$1,450,000 runs 71% above the WINTER PARK 32789 median — but at 3,578 sqft it's also nearly twice the size of the typical Winter Park listing.
02Strong assigned schools
Glenridge Middle, Winter Park High, Brookshire Elementary — Winter Park High rates 4 of 5. Always verify assignments with the district.
03The price has already moved
Listed at $1,550,000, now $1,450,000 — a $100K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of KELLY PRICE & COMPANY LLC · Kelly Price. MLS #O6415941.
IDX 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 accurate by Stellar MLS.
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