Features & Amenities

Interior

  • Other Interior Features

    Crown Molding, Eat-in Kitchen, High Ceilings, Open Floorplan, Stone Counters, Walk-In Closet(s)

  • Total Bedrooms

    4

  • Bathrooms

    3

  • 1/2 Bathrooms

    1

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Central, Electric

  • Pet friendly

    Yes

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Block, Stucco

  • Parking

    Driveway, Attached

  • Patio and Porch Features

    Rear Porch, Screened

  • Pool

    No

  • Waterfront YN

    NO

Area & Lot

  • Lot Size(acres)

    0.14

  • Lot Size(square feet)

    6294.0

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Mediterranean

Price

  • Sales Price

    $1,550,000

  • Tax Amount

    $10,592

  • Sq. Footage

    3, 578

  • Price/SqFt

    $433

HOA

  • Association

    Yes

  • Association Fee

    $805

  • Association Fee Frequency

    Quarterly

  • Association Fee Includes

    N/A

  • Total Monthly Fees

    $268.33

School District

  • Elementary School

    Brookshire Elem

  • Middle School

    Glenridge Middle

  • High School

    Winter Park High

Property Features

  • New Construction

    NO

  • Foundation Details

    Slab

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    17

  • Water Source

    Public

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Location

County

Orange

Elementary School

Brookshire Elem

Middle School

Glenridge Middle

High School

Winter Park High

Listing Courtesy of Kelly Price , KELLY PRICE & COMPANY LLC

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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.

1421 CHAPMAN CIRCLE

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