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1421 Chapman Circle , Winter Park, FL 32789

$1,550,000
  • 1421 Chapman Circle , Winter Park, FL 32789 Main Photo

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New to the Market Active
BEDS4 BATHS3 full 1 partial SQUARE FEET3,578 MLS#O6415941
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONWINDSONG ELIZABETHS WALK 43/81

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.

1421 Chapman Circle | MLS# O6415941

This single family home located at 1421 Chapman Circle , Winter Park, FL 32789 is currently listed for sale with an asking price of $1,550,000. This property was built in 2005 and has 4 bedrooms and 3 full and 1 partial baths with 3578 sq. ft. Chapman Circle is located in the WINDSONG ELIZABETHS WALK 43/81 subdivision. Search WINDSONG ELIZABETHS WALK 43/81 real estate on rarivera.realty100.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Garage: 2 car attached
Heating: Central, Electric
Home Style: Mediterranean
Lot Size: 0.14 Acres
Roof Type: Tile
Stories: 2.0
Taxes: $10,592
Year Built: 2005

Amenities

Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
High Ceilings
Open Floorplan
Primary Bedroom Main Floor
Split Bedroom
Stone Counters
Thermostat
Walk-In Closet(s)
French Doors
Private Mailbox
Sidewalk

Feature Descriptions

Additional Rooms: Formal Dining Room Separate, Inside Utility
Appliances: Built-In Oven, Dishwasher, Microwave, Range Hood, Refrigerator
Community Features: Deed Restrictions, Park, Playground, Pool, Sidewalks
Directions: From Glenridge: Turn onto Preserve Point Drive. Turn right onto Elizabeths Walk. Turn right onto Chapman Circle. Home is on right side.
Exterior: Block, Stucco
Fireplace: Gas, Living Room
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Hardwood, Tile
Foundation: Slab
HOA Fee: 805/ Quarterly
HOA Y/N: Yes
Home Warranty Y/N: No
Lot Dimensions: 0.14
Ownership: Fee Simple
Parking: Driveway
Parking Notes: Driveway
Patio/Porch: Rear Porch, Screened
Pets Allowed: Yes
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, No Lockbox, ShowingTime
Special Sale Provisions: None
Special View Info: Water
Utilities: BB/HS Internet Available, Cable Available, Natural Gas Connected
Vegetation: Trees/Landscaped
Water: Public
Water Access: Lake - Chain of Lakes
Water Access Y/N: Yes
Windows: Blinds
Zoning: PURD

Room Sizes

Living Room: 19x22
Kitchen: 16x13
Dining Room: 13x13
Office: 12x10
Primary Bedroom: 15x12
Bedroom 2: 12x14
Bedroom 3: 15x12
Bedroom 4: 12x13

Local Schools

High School: Winter Park High
Middle School: Glenridge Middle
Elementary School: Brookshire Elem

Listed By / Shown By

Listed By

Agency Name: KELLY PRICE & COMPANY LLC
Agency Contact: 407-645-4321

Shown By

Agent Name: Ramon Rivera
Agent Phone: Cell: (401) 230-9074
Agency Title: Realty 100

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Estimated Payment

$ 4,784.38 per month $3,449.63 Principal & Interest $882.67 Property Tax $452.08 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/12/2026. The listing information on this page last changed on 06/12/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 06/12/2026 12:00:23 AM EST) or Miami MLS (last updated Thu 06/11/2026 11:50:24 PM EST) or Stellar MLS (last updated Thu 06/11/2026 11:44:44 PM EST) or Beaches MLS (last updated Thu 06/11/2026 11:51:05 PM EST). Real estate listings held by brokerage firms other than Realty 100 may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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