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$1,280,000
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Property Description
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.
Full Property Details
Full Property Details for 1429 Chapman Cir
General
- Sold For: $1,280,000
- HOA FEE: $262/month
- HOA FEE FREQ.: Quarterly
- Taxes: $11,704 (2025)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6257912
- Added to Site: 474 day(s) ago
Rental Information
- Min. Lease: 7 Months
Interior
- Number of Rooms: 8
- Interior Features: Built-in Features, Ceiling Fan(s), High Ceilings, Kitchen and Family Room Combination, Open Floorplan, PrimaryBedroom Upstairs, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
- Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Microwave, Range Hood, Refrigerator
- Flooring: Carpet, Porcelain Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 4
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room, Upper Level
Additional Information
- Shared Amenities: Park, Playground, Pool
Exterior
- Exterior Features: Irrigation System, Rain Gutters, Sidewalk, Sliding Doors, Sprinkler Metered
- Deck/Patio: Covered
- Porch/Patio/Deck: Covered
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway, Garage Door Opener
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: WINDSONG ELIZABETHS WALK
- Driving Directions: Glenridge Way to Preserve Point Dr. to right on Elizabeth's Walk to right on Chapman Cir.
- Direction Faces: North
School Information
- Elementary School: Brookshire Elem
- Middle School: Glenridge Middle
- High School: Winter Park High
Community
- Community Name: 32789 - Winter Park
- Community Features: Dock, Fishing, Water Access, Deed Restrictions, Playground, Pool, Sidewalks
- Optional Amenities: Park, Playground, Pool
- Association: Yes
- Assoc. Name: Greg Ashworth
- Assoc. Fees Include: Community Pool, Pool Maintenance
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water District: LAKE MIZELL
- Water: Public
- Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Street Lights, Underground Utilities
Structural Information
- Architectural Info: Contemporary
- Architectural Style: Contemporary
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Windows: Shutters
- Stories/Levels: Two
- Square Feet: 3,116
- Sq. Ft. Source: Appraiser
- Living Area: 3,116 Sq. Ft.
- Year Built: 2014
Lot Features
- Lot Size (Acres): 0.14
- Lot Size (Sq. Ft.): 6,294
- Lot Size: 6294
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Fenced
Water Features
- Water Access: Yes
- Water Access Desc: Lake, Lake - Chain of Lakes
- Water Front Name: LAKE MIZELL
Financial Considerations
- Association Fee: $785
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $11,704
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WINDSONG - ELIZABETHS WALK 43/81 LOT 19
- Flood Zone Info: X
- APN: 172230937100190
- Property ID: 172230937100190
Listed by Corcoran Premier Realty
Sold by Premier Sotheby's Intl. Realty
Get Pre-Approved Today
Schools
Schools serving 1429 Chapman Cir
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Brookshire Elementary School 2500 Cady Way, Winter Park, FL 32792 | PK-5 | 1.3 mi |
Glenridge Middle School 2900 Upper Park Road, Orlando, FL 32814 | 6-8 | 0.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1429 Chapman Cir
Date
Details
Price
Change
Source
2/24/2026
Sold
$1,280,000
-1.46%
MLS
1/02/2026
Price Reduced
$1,299,000
-3.77%
MLS
11/20/2025
Price Reduced
$1,349,950
-1.82%
MLS
10/21/2025
Price Reduced
$1,374,950
-1.72%
MLS
9/03/2025
Price Reduced
$1,399,000
-3.45%
MLS
8/20/2025
Price Reduced
$1,449,000
-3.34%
MLS
7/21/2025
Price Reduced
$1,499,000
-1.7%
MLS
7/16/2025
Price Reduced
$1,525,000
-4.69%
MLS
4/15/2025
Price Reduced
$1,599,999
-2.97%
MLS
2/25/2025
Price Reduced
$1,649,000
-1.55%
MLS
1/16/2025
Price Reduced
$1,674,999
-1.41%
MLS
11/15/2024
Listed
$1,699,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
1429 Chapman Circle, Winter Park, FL 32789 (MLS# O6257912) is a Single Family property that was sold at $1,280,000 on February 24, 2026. Want to learn more about 1429 Chapman Circle? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

