Skip to content
Front Exterior

1429 Chapman CircleWinter Park, FL, 32789

4beds
4baths
3,116sqft
Single Family Residence
Built in 2014
$785 Quarterly HOA Fee
$1,280,000
Sold
Price per sqft
$411
Sold on
Feb 24, 2026
MLS #O6257912Updated Feb 24, 2026

About this property

Exceptional Phil Kean-designed contemporary masterpiece in Winter Park's prestigious Windsong community. This sophisticated 4-bedroom, 4-bathroom residence seamlessly blends modern luxury with practical living across two thoughtfully planned levels. The striking exterior features geometric lines, stacked stone accents, and dramatic double entry doors, setting the tone for the remarkable interior. A grand foyer with continuing stone elements welcomes you into an open-concept main level, perfect for both entertaining and daily living. Walls of 8-foot sliding glass doors blur the lines between indoor and outdoor spaces, opening to a covered 12' x 25' lanai. The showstopping gourmet kitchen serves as the heart of the home, featuring a commanding 6' x 6' granite island, KitchenAid stainless steel appliances including a professional 6-burner gas cooktop, generous walk-in pantry, and sleek dark cabinetry contrasting with the subway tile backsplash and white countertops. A sophisticated blue ceiling detail and sunburst light fixture add artistic flair to this culinary haven. The main level includes a private en-suite guest room, while the upper level houses the primary suite, two additional en-suite bedrooms, a versatile loft workspace, and laundry facilities. Recent premium upgrades include a whole-home generator, surge protection system, EV charging outlet, hardwood flooring in upstairs guest rooms, home theater electronics, whole-home audio, and security system with integrated smoke detection. Located in the amenity-rich Windsong community, residents enjoy chain of lakes access, multiple community pools, and playground facilities. Minutes from the vibrant dining scenes of Audubon Park Garden District, Mills 50, and Winter Park's renowned Park Avenue. This masterfully designed residence offers the perfect balance of sophisticated style, modern convenience, and prime location.

Interested in this property?
Gaby, Property Specialist
Speak to GabyProperty Specialist, SerhantGaby can share what this home sold for, and find you comparable properties still on the market.
+1 (407) 490-0475
No pressure. Your details stay private.

Property details

Property type
Single Family Residence
Street address
1429 Chapman Circle
City
Winter Park
State
FL
ZIP code
32789
Year built
2014
New construction
No
Attached property
No
Faces
North
Rooms
8
Living area
3,116 sqft
Total building area
3,774 sqft
Architectural style
Contemporary
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 8:01 AM EDT

Price & sale history

EventPrice
SoldMLS #O6257912$1,280,000
Price reducedMLS #O6257912$1,299,000Change: −23.5%−$400,000
Listed for saleMLS #O6257912$1,699,000
SoldMLS #O5740253$860,000
History may be incomplete.
Explore nearby sales

Location

Recent sales nearby

Front Exterior
Learn more about this propertyGet in touch for more information
We will use your details to respond to this request and may share them with a suitable real estate professional when needed. Marketing is optional.