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$1,550,000
Active
1421 CHAPMAN CIRCLE
WINTER PARK, FL 32789 — WINDSONG ELIZABETHS WALK 43/81
4 Beds
4 Baths
3,578 sqft
0.14 acres
Built 2005
2-Car Garage
About This Property
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.
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.
Property Details
Basics
- Property Type
- Residential
- Property Subtype
- Single Family Residence
- MLS Number
- O6415941
- Year Built
- 2005
- Levels
- Two
- Architectural Style
- Mediterranean
- Additional Rooms
- Formal Dining Room Separate,Inside Utility
- Direction Faces
- North
- Occupant Type
- Owner
Size & Structure
- Living Area
- 3,578 sqft
- Total Area
- 4,529 sqft
- Lot Size
- 0.14 acres
- Lot Sq Ft
- 6,294 sqft
- Bedrooms
- 4
- Full Baths
- 3
- Half Baths
- 1
- Garage Spaces
- 2
Interior
- Flooring
- Hardwood, Tile
- Appliances
- Built-In Oven, Dishwasher, Microwave, Range Hood, Refrigerator
- Interior Features
- Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
- Laundry
- Inside, Laundry Room
- Windows
- Blinds
- Fireplace
- Yes — Gas, Living Room
- Furnished
- Unfurnished
- A/C
- Central Air
- Heating
- Central, Electric
Exterior & Lot
- Exterior Features
- French Doors, Private Mailbox, Sidewalk
- Construction
- Block, Stucco
- Roof
- Tile
- Foundation
- Slab
- Patio/Porch
- Rear Porch, Screened
Water & Pool
Community & HOA
- HOA
- Yes
- HOA Fee
- $805/Quarterly
- Community Features
- Deed Restrictions, Park, Playground, Pool, Sidewalks
- Pets Allowed
- Yes
- Homestead
- Yes
Utilities & Systems
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- BB/HS Internet Available, Cable Available, Natural Gas Connected
- Cooling
- Central Air
- Heating
- Central, Electric
- Flood Zone
- X
- Parking
- Driveway
Financial
- List Price
- $1,550,000
- Annual Taxes
- $10,592
- Tax Year
- 2025
- Special Conditions
- None
Schools
- Elementary
- Brookshire Elem
- Middle School
- Glenridge Middle
- High School
- Winter Park High