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$1,155,500
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Property 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.
Full Property Details
Full Property Details for 1421 Chapman Cir
General
- Sold For: $1,155,500
- HOA FEE: $268/month
- HOA FEE FREQ.: Quarterly
- Taxes: $10,592 (2025)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6415941
- Added to Site: 154 day(s) ago
Rental Information
- Min. Lease: 1-2 Years
Interior
- Number of Rooms: 8
- Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Gas, Living Room
- Appliances: Built-In Oven, Dishwasher, Microwave, Range Hood, Refrigerator
- Furnishings: Unfurnished
- Flooring: Engineered Hardwood, Tile
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Inside, Laundry Room
Exterior
- Exterior Features: French Doors, Private Mailbox, Sidewalk
- Deck/Patio: Rear Porch, Screened
- Porch/Patio/Deck: Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Driveway
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: WINDSONG ELIZABETHS WALK 43/81
- Driving Directions: From Glenridge: Turn onto Preserve Point Drive. Turn right onto Elizabeths Walk. Turn right onto Chapman Circle. Home is on right side.
- 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: Fishing, Lake, Deed Restrictions, Park, Playground, Pool, Sidewalks
- Association: Yes
- Assoc. Name: Leland Management
- Assoc. Fees Include: Manager, Recreational Facilities
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Natural Gas Connected
Structural Information
- Architectural Info: Mediterranean
- Architectural Style: Mediterranean
- Exterior Const.: Block, Stucco
- Roof: Tile
- Windows: Blinds
- Stories/Levels: Two
- Square Feet: 3,578
- Sq. Ft. Source: Public Records
- Living Area: 3,578 Sq. Ft.
- Year Built: 2005
Lot Features
- Lot Size (Acres): 0.14
- Lot Size (Sq. Ft.): 6,294
- Lot Size: 6294
- Street/Road Desc.: Paved
Water Features
- Water Access: Yes
- Water Access Desc: Lake - Chain of Lakes
- Water Front Desc.: Lake
Financial Considerations
- Association Fee: $805
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $10,592
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WINDSONG - ELIZABETHS WALK 43/81 LOT 17
- Flood Zone Info: X
- APN: 172230937100170
- Property ID: 172230937100170
Listed by Kelly Price & Company Llc
Sold by Baldwin Park Realty Llc
Get Pre-Approved Today
Schools
Schools serving 1421 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 |
Winter Park High School 2100 Summerfield Road, Winter Park, FL 32792 | 9-12 | 0.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1421 Chapman Cir
Date
Details
Price
Change
Source
10/22/2026
Sold
$1,155,500
-16.12%
MLS
9/08/2026
Price Reduced
$1,377,500
-5%
MLS
7/11/2026
Price Reduced
$1,450,000
-6.45%
MLS
6/12/2026
Listed
$1,550,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
1421 Chapman Circle, Winter Park, FL 32789 (MLS# O6415941) is a Single Family property that was sold at $1,155,500 on October 22, 2026. Want to learn more about 1421 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.
