$1,550,000
1421 Chapman Circle Winter Park, FL 32789
For Sale MLS# O6415941
4 beds 4 baths 3,578 sq ft Single Family
Details for 1421 Chapman Circle
MLS# O6415941
Description for 1421 Chapman Circle, Winter Park, FL, 32789
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.
Listing Information
Property Type: Residential, Single Family Residence
Status: Active
Bedrooms: 4
Bathrooms: 4
Lot Size: 0.14 Acres
Square Feet: 3,578 sq ft
Year Built: 2005
Garage: Yes
Stories: 2 Story
Construction: Block,Stucco
Subdivision: Windsong Elizabeths Walk 43/81
Foundation: Slab
County: Orange
School Information
Elementary: Brookshire Elem
Middle: Glenridge Middle
High: Winter Park High
Room Information
Main Floor
Primary Bedroom: 12x15
Office: 10x12
Dining Room: 13x13
Kitchen: 13x16
Living Room: 22x19
Upper Floor
Bedroom 4: 13x12
Bedroom 3: 12x15
Bedroom 2: 14x12
Bathrooms
Full Baths: 3
1/2 Baths: 1
Additonal Room Information
Laundry: Laundry Room, Inside
Interior Features
Appliances: Range Hood, Built-In Oven, Dishwasher, Microwave, Refrigerator
Flooring: Engineered Hardwood,Tile
Doors/Windows: Blinds
Fireplaces: Gas, Living Room
Additional Interior Features: Ceiling Fan(s), Eat-In Kitchen, Walk-In Closet(s), Split Bedrooms, High Ceilings, Separate/Formal Dining Room, Main Level Primary, Crown Molding, Stone Counters, Open Floorplan
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Available,Natural Gas Connected,High Speed Internet Available
Cooling: Central Air, Ceiling Fan(s)
Heating: Electric, Central
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 2
Parking Description: driveway
Roof: Tile
Pool: Community
Additional Exterior/Lot Features: French Patio Doors, Screened, Rear Porch, Landscaped
Community Features
Community Features: Pool, Playground, Sidewalks, Lake, Park, Fishing
HOA Dues Include: Association Management, Recreation Facilities
Homeowners Association: Yes
HOA Dues: $805 / Quarterly
Driving Directions
From Glenridge: Turn onto Preserve Point Drive. Turn right onto Elizabeths Walk. Turn right onto Chapman Circle. Home is on right side.
Financial Considerations
Tax/Property ID: 17-22-30-9371-00-170
Tax Amount: 10592
Tax Year: 2025
A broker reciprocity listing courtesy: KELLY PRICE & COMPANY LLC
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Interest rate and annual percentage rate (APR) are based on current market conditions, are for informational purposes only, are subject to change without notice and may be subject to pricing add-ons related to property type, loan amount, loan-to-value, credit score and other variables. Estimated closing costs used in the APR calculation are assumed to be paid by the borrower at closing. If the closing costs are financed, the loan, APR and payment amounts will be higher. If the down payment is less than 20%, mortgage insurance may be required and could increase the monthly payment and APR. Contact us for details. Additional loan programs may be available. Accuracy is not guaranteed, and all products may not be available in all borrower's geographical areas and are based on their individual situation. This is not a credit decision or a commitment to lend.
Sales History & Tax Summary for 1421 Chapman Circle
Sales History
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Tax Summary
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Schools
Schools nearby 1421 Chapman Circle
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The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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