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1421 Chapman Circle

Winter Park, FL 32789
  • $1,450,000
  • STATUS: Active
  • ON SITE: 63 Days
  • MLS #: O6415941
Open House
UPDATED: 192 min ago
$1,450,000
  • 4
    BEDS
  • 0.14
    ACRES
  • 3
    BATHS
  • 1
    1/2 BATHS
  • 3,578
    SQFT
  • $405
    $/SQFT
Type:
Single-Family Home
Built:
2005
County:
Area:

School Information

Elementary School:
Middle School:
High School:

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.

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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-08-14T23:44:06.507.
www.onestopre.net/homes/177649736
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1421 Chapman Circle Winter Park, FL 32789

  • Price: $1,450,000
  • Status: Active
  • On Site: 63 Days
  • Updated: 192 min ago
  • MLS #: O6415941
4
Beds
3
Baths
1
½ Baths
0.14
Acres
3,578
SQFT
$405
$/SQFT
2005
Built
Neighborhood:
Windsong Elizabeths Walk 43/81
County:
Orange
Area:
Winter Park
Elementary School:
Brookshire Elem
Middle School:
Glenridge Middle
High School:
Winter Park High
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.
Exterior Features

Architectural Style Mediterranean Attached Garage Yn Yes Carport Yn No Construction Materials BlockStucco Covered Spaces 2 Direction Faces North Exterior Features French DoorsPrivate MailboxSidewalk Foundation Details Slab Open Parking YN Yes Parking Features Driveway Patio And Porch Features Rear PorchScreened Pool Private Yn No Road Surface Type Paved Roof Tile Water Access Lake - Chain of Lakes Water Access Yn Yes Water Extras Yn No Water View Yn No Waterfront Features Lake Waterfront Yn No

Interior Features

Additional Rooms Formal Dining Room SeparateInside Utility Appliances Built-In OvenDishwasherMicrowaveRange HoodRefrigerator Building Area Total 4529 Cooling Central Air Cooling YN Yes Fireplace Features GasLiving Room Fireplace Yn Yes Flooring Engineered HardwoodTile Furnished Unfurnished Heating CentralElectric Heating YN Yes Interior Features Ceiling Fan(s)Crown MoldingEating Space In KitchenHigh CeilingsOpen FloorplanPrimary Bedroom Main FloorSplit BedroomStone CountersThermostatWalk-In Closet(s) Laundry Features InsideLaundry Room Levels Two Sewer Public Sewer Water Source Public Window Features Blinds

Property Features

Additional Lease Restrictions Buyer to verify all lease restrictions with HOA and local municipality Additional Parcels YN No Approval Process Buyer to verify an approval processes with HOA Association Approval Required Yn No Association Fee 805 Association Fee Frequency Quarterly Association Fee Includes ManagerRecreational Facilities Association Fee Monthly Amount 268.33 Association Fee Requirement Required Association Yn Yes Cdd Yn No Community Features FishingLakeDeed RestrictionsParkPlaygroundPoolSidewalks Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Minimum Lease 1-2 Years New Construction Yn No Occupant Type Owner Ownership Fee Simple Pets Allowed Yes Property Sub Type Single Family Residence Senior Community Yn No Special Listing Conditions None Tax Annual Amount 10592 Total Annual Fees 3220 Total Monthly Fees 268.33 Utilities BB/HS Internet AvailableCable AvailableNatural Gas Connected Yrs Of Owner Prior To Leasing Re No Zoning PURD


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of KELLY PRICE & COMPANY LLC: 407-645-4321.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-08-14T23:44:06.507.
 
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