321 SYLVAN BOULEVARD
Winter Park, FL 32789
$1,300,000
Set on a rare double lot in one of Winter Park's most coveted locations, this charming 1940 Craftsman-style residence presents an extraordinary opportunity to enjoy one of Central Florida's most celebrated lifestyles while envisioning the future. Just moments from the Winter Park Chain of Lakes, the boutiques and acclaimed dining of Park Avenue, and the timeless beauty of Rollins College, the property offers a setting that few locations can rival.
The existing residence features approximately three bedrooms, two-and-a-half bathrooms, and generously proportioned living spaces filled with warmth and character. Lovingly maintained over the years, the home provides a comfortable foundation for renovation, restoration, or reimagination. Outdoors, a screened pool creates a private retreat for year-round enjoyment, while a detached two-car garage and separate studio shed offer exceptional flexibility for hobbies, creative pursuits, a home office, fitness space, or guest accommodations.
What truly distinguishes this offering is the double lot itself. Opportunities of this scale within the heart of Winter Park are increasingly rare, providing the space and flexibility to construct a custom estate tailored to your vision while preserving ample room for outdoor living, gardens, and recreation.
Life here extends far beyond the property lines. Enjoy morning walks beneath majestic oak canopies, afternoons on the Chain of Lakes, outdoor concerts, art festivals, sidewalk cafés, and some of Florida's most picturesque streetscapes. Whether renovating the existing residence or creating the home of your dreams, this exceptional property represents a rare chance to secure a ...
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Listing Courtesy of: PREMIER SOTHEBYS INT'L REALTY
407-333-1900
Buyer Represented by: ONE LUXURY INTERNATIONAL LLC
| Listing Id: | O6417674 |
|---|---|
| List Price: | $1,395,000 |
| Close Price: | $1,300,000 |
| Close Date: | 2026-07-24 |
| Property Type: | Residential |
| Property Sub Type: | Single Family Residence |
| Status: | Closed |
| Bedrooms Total: | 3 |
| Bathrooms Full: | 2 |
| Bathrooms Half: | 1 |
| Living Area: | 2,821 |
| Tax Annual Amount: | $6,544 |
| Lot Size Square Feet: | 16,519 |
| Lot Size Acres: | 0.38 |
| Waterfront?: | No |
| City: | Winter Park |
| County Or Parish: | Orange |
| Subdivision Name: | Sylvan Lake Shores |
| Postal Code: | 32789 |
| Year Built: | 1940 |
| Appliances: | Range, Refrigerator |
| Bathrooms Total Integer: | 3 |
| Building Area Source: | Public Records |
| Building Area Total: | 3697 |
| Building Area Units: | Square Feet |
| Direction Faces: | East |
| Foundation Details: | Concrete Perimeter |
| Construction Materials: | Frame |
| Cooling: | Central Air |
| Fireplace Features: | Other |
| Directions: | From Park Ave, E on Aloma Ave, R on Sylvan Blvd. |
| Elementary School: | Brookshire Elem |
| Exterior Features: | Private Mailbox |
| Flooring: | Carpet, Wood |
| Furnished: | Unfurnished |
| Garage Spaces: | 2 |
| Garage?: | Yes |
| Heating: | Central, Zoned |
| High School: | Winter Park High |
| Interior Features: | Ceiling Fans(s) |
| Laundry Features: | Laundry Room |
| Levels: | One |
| Ownership: | Fee Simple |
| Living Area Source: | Public Records |
| Living Area Units: | Square Feet |
| Lot Size Acres: | 0.38 |
| Postal Code Plus4: | 4047 |
| Middle Or Junior School: | Glenridge Middle |
| MLS Area Major: | 32789 - Winter Park |
| MLS Area Major: | 32789 - Winter Park |
| Original List Price: | $1,395,000 |
| Parcel Number: | 05-22-30-8506-02-091 |
| Patio And Porch Features: | Front Porch, Rear Porch |
| Pool Features: | Gunite, In Ground, Screen Enclosure |
| Stories Total: | 1 |
| Township: | 22 |
| Road Surface Type: | Brick |
| Roof: | Shingle |
| Listing Terms: | Cash, Conventional |
| Tax Year: | 2025 |
| Sewer: | Public Sewer |
| Special Listing Conditions: | None |
| State Or Province: | FL |
| Utilities: | BB/HS Internet Available, Cable Available, Electricity Connected, Phone Available, Public, Sewer Connected, Water Connected |
| Water Source: | Public |
| Public Survey Range: | 30 |
| Public Survey Section: | 05 |
| Zoning: | R-1A |
| Alternate Key Folio Num: | 302205850602091 |
| Available For Lease Yn: | Yes |
| Backups Requested Yn: | No |
| Building Area Total Srch Sq M: | 343.46 |
| Calculated List Price By Calcula: | 494.51 |
| Cddyn: | No |
| Dprurl: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6417674?w=Agent&skip_sso=true |
| Dprurl 2: | https://www.workforce-resource.com/dpr/listing/MFRMLS/O6417674?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: | 262.08 |
| Lot Size Square Meters: | 1535 |
| Minimum Lease: | No Minimum |
| Room Count: | 7 |
| Sdeo yn: | No |
| Total Acreage: | 1/4 to less than 1/2 |
| Unit Number Yn: | No |
| Water Access Yn: | No |
| Water Extras Yn: | No |
| Water View: | No |
| Road Responsibility: | Public Maintained Road |
| Association 2 Yn: | 0 |
| Attribution Contact: | 407-333-1900 |
| Originating System Name : | Stellar MLS |
| In Law Suite Yn: | No |
| Green Energy Generation Yn: | No |
| Listing Contract Date: | 2026-06-17 |
| Fireplace?: | Yes |
| Pool Private?: | Yes |
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Property Last Updated: October 21, 2026 01:26 AM - ET
