1421 CHAPMAN CIRCLE
Winter Park, FL 32789
$1,155,500
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 ...
+ Read More
Listing Courtesy of: KELLY PRICE & COMPANY LLC
407-645-4321
Buyer Represented by: BALDWIN PARK REALTY LLC
| Listing Id: | O6415941 |
|---|---|
| List Price: | $1,377,500 |
| Close Price: | $1,155,500 |
| Close Date: | 2026-10-22 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Closed |
| Bedrooms Total: | 4 |
| Bathrooms Full: | 3 |
| Bathrooms Half: | 1 |
| Living Area: | 3,578 |
| Tax Annual Amount: | $10,592 |
| Lot Size Square Feet: | 6,294 |
| Lot Size Acres: | 0.14 |
| Architectural Style: | Mediterranean |
| Waterfront?: | No |
| City: | Winter Park |
| County Or Parish: | Orange |
| Subdivision Name: | Windsong Elizabeths Walk 43/81 |
| Postal Code: | 32789 |
| Year Built: | 2005 |
| Appliances: | Built-In Oven, Dishwasher, Microwave, Range Hood, Refrigerator |
| Association Fee: | $805 |
| Association Fee Frequency: | Quarterly |
| Association Fee Includes: | Management, Recreational Facilities |
| Attached Garage?: | Yes |
| Bathrooms Total Integer: | 4 |
| Building Area Source: | Public Records |
| Building Area Total: | 4529 |
| Building Area Units: | Square Feet |
| Direction Faces: | North |
| Foundation Details: | Slab |
| Construction Materials: | Block, Stucco |
| Cooling: | Central Air |
| Fireplace Features: | Gas, Living Room |
| Directions: | From Glenridge: Turn onto Preserve Point Drive. Turn right onto Elizabeths Walk. Turn right onto Chapman Circle. Home is on right side. |
| Elementary School: | Brookshire Elem |
| Exterior Features: | Private Mailbox, Sidewalk |
| Flooring: | Hardwood, Tile |
| Furnished: | Unfurnished |
| Garage Spaces: | 2 |
| Garage?: | Yes |
| Community Features: | Deed Restrictions, Park, Playground, Pool, Sidewalks |
| Heating: | Central, Electric |
| High School: | Winter Park High |
| Interior Features: | 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) |
| Laundry Features: | Inside, Laundry Room |
| Levels: | Two |
| Ownership: | Fee Simple |
| Living Area Source: | Public Records |
| Living Area Units: | Square Feet |
| Lot Size Acres: | 0.14 |
| Postal Code Plus4: | 5953 |
| Middle Or Junior School: | Glenridge Middle |
| MLS Area Major: | 32789 - Winter Park |
| MLS Area Major: | 32789 - Winter Park |
| Original List Price: | $1,550,000 |
| Parcel Number: | 17-22-30-9371-00-170 |
| Parking Features: | Driveway |
| Patio And Porch Features: | Rear Porch, Screened |
| Pets Allowed: | Yes |
| Township: | 22 |
| Road Surface Type: | Paved |
| Roof: | Tile |
| Tax Year: | 2025 |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Association?: | Yes |
| Utilities: | BB/HS Internet Available, Cable Available, Natural Gas Connected |
| Water Source: | Public |
| Public Survey Range: | 30 |
| Public Survey Section: | 17 |
| Zoning: | PURD |
| Vegetation: | Trees/Landscaped |
| Window Features: | Blinds |
| Additional Lease Restrictions: | Buyer to verify all lease restrictions with HOA and local municipality |
| Additional Rooms: | Formal Dining Room Separate, Inside Utility |
| Alternate Key Folio Num: | 17-22-30-9371-00-170 |
| Approval Process: | Buyer to verify an approval processes with HOA |
| Association Approval Required Yn: | No |
| Association Email: | gashworth@lelandmanagment.com |
| Association Fee Requirement: | Required |
| Available For Lease Yn: | Yes |
| Backups Requested Yn: | Yes |
| Building Area Total Srch Sq M: | 420.76 |
| Calculated List Price By Calcula: | 384.99 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6415941?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6415941?w=Customer |
| Dpryn: | No |
| Exist Lse Tenant Yn: | No |
| Flood Zone Code: | X |
| Flood Zone Date: | 2009-09-25 |
| Flood Zone Panel: | 12095C0255F |
| Green Verification Count: | 0 |
| Homestead Yn: | Yes |
| Lease Restrictions Yn: | No |
| Listing Exclusion Yn: | No |
| Living Area Meters: | 332.41 |
| Lot Size Square Meters: | 585 |
| Minimum Lease: | 1-2 Years |
| Monthly Hoa Amount: | $268 |
| Other Exemptions Yn: | Yes |
| Room Count: | 8 |
| Sdeo yn: | No |
| Total Acreage: | 0 to less than 1/4 |
| Total Annual Fees: | $3,220 |
| Total Monthly Fees: | $268 |
| Unit Number Yn: | No |
| Water Access: | Lake - Chain of Lakes |
| Water Access Yn: | Yes |
| Water Extras Yn: | No |
| Water View: | No |
| Yrs Of Owner Prior To Leasing Re: | 0 |
| Association Name: | Leland Management |
| Association Phone: | (407) 781-1836 |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-645-4321 |
| Originating System Name : | Stellar MLS |
| Community Association Water Features: | Fishing, Lake |
| Dock Yn: | No |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-06-12 |
| Fireplace?: | Yes |
Mortgage Calculator
Copyright 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. Information deemed reliable but is not guaranteed. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of My Florida Regional MLS DBA Stellar MLS. Real estate listings held by brokerage firms other than the owner of this page include the name of the listing broker. Information provided is for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This site will be monitored for 'scraping' and any use of search facilities of data on the site other than by a consumer looking to purchase real estate is prohibited. Listing broker has attempted to offer accurate data, but buyers are advised to confirm all items. Information last updated on October 24, 2026 04:17 AM - ET
Based on information submitted to the MLS GRID as of October 24, 2026 04:17 AM - ET. 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. Properties displayed may be listed or sold by various participants in the MLS. Some listings have been excluded from this website.
IDX information is provided exclusively for consumers’ personal noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time.
Property Last Updated: October 24, 2026 04:17 AM - ET
