1421 Chapman CircleWinter Park, FL 32789Price: $1,550,000

  • Price: $1,550,000
  • Est. Mortgage of $/month
  • 1 Day on Market
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$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
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Open House
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  • 4Bedrooms
  • 0.14Acreage
  • 4Bathrooms
  • 2005Year Built
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.

Open Houses

June 13th
Starts: 1:00pm
Ends: 3:00pm
June 14th
Starts: 2:00pm
Ends: 4:00pm
Listing Courtesy of KELLY PRICE & COMPANY LLC

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More Info

Location Information

  • Road Frontage DescriptionPaved

School Information

  • Elementary SchoolBrookshire Elem
  • High SchoolWinter Park High
  • Junior HighGlenridge Middle

Parking

  • Parking Features Driveway

Rooms

  • Bedrooms4
  • Full Bath3
  • Half Baths1
  • MFR Additional Rooms Formal Dining Room Separate, Inside Utility

Building

  • Bathroom4
  • Construction Materials Block, Stucco
  • FireplaceGas, Living Room
  • Fireplace YN Yes
  • Foundation Details Slab
  • GarageYes
  • Garage Spaces2
  • Levels Two
  • Patio And Porch Features Rear Porch, Screened
  • Property StyleMediterranean
  • RoofTile
  • Rooms8
  • Window Features Blinds
  • Year Built2005

Water Body

  • MFR Water Access YN Yes
  • Water AccessLake - Chain of Lakes
  • Water ViewNo

Other

  • Building Area Source Public Records
  • Date Listed06/12/2026
  • MFR Additional Lease Restrictions Buyer to verify all lease restrictions with HOA and local municipality
  • MFR Exist Lse Tenant YN No
  • MFR Flood Zone Code X
  • MFR Flood Zone Date 2009-09-25
  • MFR Minimum Lease 1-2 Years
  • Status Change Timestamp2026-06-12T15:30:53
  • Vegetation Trees/Landscaped

Basic Information

  • List Price$1,550,000
  • ListingContractDate2026-06-12
  • MLS NumberO6415941
  • Mls Status Active
  • OriginalListPrice1550000
  • PostalCodePlus45953
  • PublicSurveyRange30
  • StatusACT

Basic Information

  • Property SubTypeSingle Family Residence
  • Property TypeResidential
  • Virtual TourView Tour

Property

  • ZoningPURD

Interior

  • Flooring Hardwood, Tile
  • Furnished Unfurnished

Utilities

  • Cooling Central Air
  • Heating Central, Electric
  • Laundry Features Inside, Laundry Room
  • Sewer Public Sewer
  • Utilities BB/HS Internet Available, Cable Available, Natural Gas Connected
  • Water Source Public

Amenities

  • Appliances IncludedBuilt-In Oven, Dishwasher, Microwave, Range Hood, Refrigerator
  • Association Fee Includes Management, Recreational Facilities
  • Association YN Yes
  • Community Features Deed Restrictions, Park, Playground, Pool, Sidewalks
  • Other AmenitiesFireplace, Pool, Dock
  • PetsYes

Tax Information

  • Association Fee $805
  • Association Fee Frequency Quarterly
  • Fees$3,220
  • MFR Association Fee Requirement Required
  • Monthly HOA Amount $268
  • Tax Year 2025
  • Taxes$10,592
  • Total Monthly Fees $268

Location

  • Address1421 Chapman Circle
  • AreaWinter Park
  • CountyOrange
  • Exterior Features French Doors, Private Mailbox, Sidewalk
  • StateFL
  • SubdivisionWindsong Elizabeths Walk 43/81
  • TownWinter Park
  • Township 22
  • Zip32789

Property Information

  • Acreage0.14
  • Attached Garage YN Yes
  • Building Area Total 4,529
  • BuildingAreaUnitsSquare Feet
  • LivingAreaUnitsSquare Feet
  • Lot Size Square Feet 6,294
  • MFR Living Area Meters 332
  • MFR Lot Size Square Meters 585
  • MFR Total Acreage 0 to less than 1/4
  • Square Feet3,578
Fusilier Realty Group
Fusilier Realty Group
Office: 407-281-8455
10016 Wellness Way
Orlando, FL 32832

Listings courtesy of StellarMLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of June 13, 2026 7:34 AM UTC. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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