1421 CHAPMAN CIRCLE Winter Park, FL $ 1,550,000
1421 CHAPMAN CIRCLE
$ 1,550,000
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Open House 6/14 2pm - 4pm
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1421 CHAPMAN CIRCLE

Winter Park, FL, 32789
$ 1,550,000
Bedrooms4 Baths3.1 Sq 3,578

Monthly Estimate*

$ 9,544

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Single Family Home for sale in Winter Park, FL

for $1,550,000 with 4 bedrooms and 3 full baths, 1 half bath. This 3,578 square foot home was built in 2005 on a lot size of 0.14.

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.

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Open House

6/14/2026 2:00 PM - 4:00 PM
1421 CHAPMAN CIRCLE Winter Park, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 1,550,000

Bedrooms

4

Full Bath

3

Half Bath

1

Property Type

Single Family

Taxes

$ 10,592

Style

Mediterranean

Lot Size

0.14

Year Built

2005

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6415941

Features
General
Sewer Public Sewer
Heating Central Electric
Cooling Central Air
Utilities BB/HS Internet Available Cable Available Natural Gas Connected
Roof Tile
Appliances Built-In Oven Dishwasher Microwave Range Hood Refrigerator
Zoning PURD
HOA Fee 805
Garage Spaces 2
Association Fee Includes Manager Recreational Facilities
Patio/Porch Features Rear Porch Screened
Architectural Style Mediterranean
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 2005
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Waterfront Features Lake
Community Features Fishing Lake Deed Restrictions Park Playground Pool Sidewalks
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name WINDSONG ELIZABETHS WALK 43/81
Facing Direction North
Garage Y/N true
Total Rooms 8
Full Baths 3
Status Active
Directions From Glenridge: Turn onto Preserve Point Drive. Turn right onto Elizabeths Walk. Turn right onto Chapman Circle. Home is on right side.
High School Winter Park High
City WINTER PARK
Association Name Leland Management
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 6294
Carport Y/N false
Elementary School Brookshire Elem
Land Lease Y/N false
Tax Annual Amount 10592
Middle/Junior High School Glenridge Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.youtube.com/watch?v=61JNeSgLD0E
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 17
Legal Description WINDSONG - ELIZABETHS WALK 43/81 LOT 17
Water Access Type Lake - Chain of Lakes
Minimum Lease 1-2 Years
Water Access Y/N true
Monthly HOA Amount 268.33
Additional Rooms Formal Dining Room Separate Inside Utility
Water View Y/N false
Flood Zone Code X
DockY/N false
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Interior
Interior Amenities Ceiling Fan(s) Crown Molding Eating Space In Kitchen High Ceilings Open Floorplan Primary Bedroom Main Floor Split Bedroom Stone Counters Thermostat Walk-In Closet(s)
Flooring Engineered Hardwood Tile
Furnished Y/N Unfurnished
Fireplace Features Gas Living Room
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds
Fireplace Y/N true
Half Baths 1
Laundry Features Inside Laundry Room
Total Bedrooms 4
Total Baths 4
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Exterior
Exterior Amenities French Doors Private Mailbox Sidewalk
Vegetation Trees/Landscaped
Parking Features Driveway
Water Source Public
Lot Size Area 6294
Foundation Details Slab
Building Area Total 4529
Lot Size Acres 0.14
Road Surface Type Paved
Private Pool false
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
Kelly Price & Company Llc

Broker

kelly@kellypriceandcompany.com

Email

Affordability Calculator

$10,426
Per Month
92%
8%
0%
Monthly Principal & Interest
$9,544
Monthly Property Taxes
$883
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
6/12/2026$1,550,000 Listed Price

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1421 CHAPMAN CIRCLE, Winter Park, FL, 32789 is a Single Family Home for sale at $1,550,000 with 3,578 sqft and a lot size of 0.14. 1421 CHAPMAN CIRCLE has 4 bedrooms, 3.1 baths, and was built in 2005. The property's zip code is 32789 which is in Winter Park, FL