1421 Chapman Cir, Winter Park, FL 32789 | For Sale

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For Sale $1,450,000 ($405.25 per Sq Ft)

$1,450,000 ($405.25 per Sq Ft)
  • (0)
  • 4 Bedrooms
  • 4 Bathrooms
  • 3,578 Sq Ft
  • 6,294 Sq Ft

Description

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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Amenities

Garage
Pool
Garden
Security System
Internet
Telephone
Heating
Fireplace
Balcony & Patio
TV / Cable
Laundry
Hardwood Floors
Spa
Air Conditioning
Solar Power
Floor Plan
Great Views
Natural Light
Quiet
Water View
Elevator
Guest Unit(s)
Furnished
220 Volt

Upcoming Open House

Sunday August 16th, 2026
from 11:00 am - 1:00 pm

View Event

Income

Rental Units


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Property Details

List Price $1,450,000
Property Type Single Family Homes
Usable Sqft 3,578
Number of Stories 0 stories
Parking Spots 2 spots
Year Built 2005
Last Sold Unknown
Sold Price Unknown
HOA Fees: $805
Association Name: Leland Management
Association Amenities: Unknown
APN # 172230937100170
MLS # O6415941
Property ID 317123682
Lot Sqft 6,294
Zoning PURD
Days on Market 63
Original List Price $1,550,000
Applicances Built-In Oven, Dishwasher, Microwave, Range Hood, Refrigerator%
Date Updated August 14, 2026
Date Created June 12, 2026
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Listing Provided By

Kelly Price an agent of .


© 2026 STELLAR MLS. All rights reserved. Some listings on this website are from STELLAR as of August 14, 2026 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.



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