1421 Chapman Circle, Winter Park, FL 32789
Local realty services provided by:CENTURY 21 Link Realty, Inc.
1421 Chapman Circle,Winter Park, FL 32789
$1,550,000
- 4 Beds
- 4 Baths
- 3,578 sq. ft.
- Single family
- Active
Upcoming open houses
- Sat, Jun 2001:00 pm - 03:00 pm
Listed by: kelly price
Office: kelly price & company llc.
MLS#:O6415941
Source:MFRMLS
Price summary
- Price:$1,550,000
- Price per sq. ft.:$342.24
- Monthly HOA dues:$268.33
About this home
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....
Contact an agent
Home facts
- Year built:2005
- Listing ID #:O6415941
- Added:5 day(s) ago
- Updated:June 18, 2026 at 11:46 AM
Rooms and interior
- Bedrooms:4
- Total bathrooms:4
- Full bathrooms:3
- Half bathrooms:1
- Flooring:Hardwood, Tile
- Dining Description:Eat In Kitchen, Formal Dining Room
- Kitchen Description:Built-In Oven, Dishwasher, Eat-in Kitchen, Microwave, Range Hood, Refrigerator, Stone Counters
- Bedroom Description:High Ceilings, Primary Bedroom Main Floor, Split Bedroom, Walk-In Closet(s)
- Living area:3,578 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central, Electric
- Central air:Yes
Structure and exterior
- Roof:Tile
- Year built:2005
- Building area:3,578 sq. ft.
- Lot area:0.14 Acres
- Architectural Style:Mediterranean
- Construction Materials:Block, Stucco
- Exterior Features:Private Mailbox, Rear Porch, Screened, Sidewalk
- Foundation Description:Slab
- Levels:2 Story
Schools
- High school:Winter Park High
- Middle school:Glenridge Middle
- Elementary school:Brookshire Elem
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$1,550,000
- Price per sq. ft.:$342.24
- Tax amount:$10,592 (2025)
Features and amenities
- Appliances:Built-in Oven, Dishwasher, Microwave, Range Hood, Refrigerator
- Laundry features:Inside, Laundry Room
- Amenities:BB/HS Internet Available, Cable Available, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Natural Gas Connected, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
- Pool features:Public Pool
Parking
- Parking description:Attached Garage, Driveway
- Garage:Yes
- Garage spaces:2
New listings near 1421 Chapman Circle
- Open Sat, 12 to 2pmNew
$400,000Active4 beds 2 baths1,677 sq. ft.7514 Laurel Springs Drive, WINTER PARK, FL 32792
MLS# O6372653Listed by: KELLER WILLIAMS WINTER PARK - New
$1,795,000Active4 beds 4 baths2,819 sq. ft.2501 Lafayette Avenue, WINTER PARK, FL 32789
MLS# O6416565Listed by: CHARLES RUTENBERG REALTY ORLANDO - New
$1,849,900Active3 beds 4 baths3,112 sq. ft.101 S New York Avenue #311, WINTER PARK, FL 32789
MLS# O6416927Listed by: KELLY PRICE & COMPANY LLC - New
$2,350,000Active3 beds 3 baths2,143 sq. ft.140 E Morse Boulevard #J, WINTER PARK, FL 32789
MLS# O6414891Listed by: PREMIER SOTHEBY'S INTL. REALTY - New
$399,000Active3 beds 2 baths1,285 sq. ft.1605 Puritan Avenue, WINTER PARK, FL 32792
MLS# O6417098Listed by: CENTURY 21 CARIOTI - New
$195,000Active2 beds 2 baths1,058 sq. ft.4756 Tangerine Avenue #4756, WINTER PARK, FL 32792
MLS# R4911483Listed by: HOME BUYER HELPER REAL ESTATE LLC - New
$849,000Active3 beds 3 baths1,904 sq. ft.437 N Capen Avenue, WINTER PARK, FL 32789
MLS# O6414283Listed by: COMPASS FLORIDA LLC
$449,900Active3 beds 2 baths1,666 sq. ft.1840 Aster Drive, WINTER PARK, FL 32792
MLS# O6412364Listed by: KONA REALTY SERVICES LLC- New
$5,500,000Active4 beds 5 baths4,775 sq. ft.313 Sylvan Drive, WINTER PARK, FL 32789
MLS# O6407606Listed by: PREMIER SOTHEBY'S INTL. REALTY - New
$515,000Active4 beds 2 baths2,250 sq. ft.2008 Houndslake Drive, WINTER PARK, FL 32792
MLS# O6414369Listed by: MARK SPAIN REAL ESTATE