321 SYLVAN BOULEVARD, Winter Park, FL 32789

• 3 beds |
• 3 baths |
• 2,821 sqft

Property Description

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 legacy homesite in one of the most desirable addresses in Central Florida.

Listing Status:

Coming Soon

Data Last Updated:

June 24, 2026 at 5:24AM

Listing Office:

PREMIER SOTHEBYS INT'L REALTY : 407-333-1900

Listing Agent:

Mel Bernstein : 407-810-4726

MLS ID:

O6417674

Interior

• General: Ceiling Fans(s)
• Appliances: RangeRefrigerator
• Laundry: Laundry Room
• Flooring: CarpetWood
• A/C: Central Air
• Heating: CentralZoned
• Fireplace: Fireplace

Exterior

• General: Private Mailbox
• Other Structures: Front PorchRear Porch
• Pool: GuniteIn GroundScreen Enclosure

Construction

• Roofing: Shingle
• General: FrameOneConcrete Perimeter

Location

• Road/Access: Brick
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-1ASYLVAN LAKE SHORES N/48 THE S 1/2 OF LOT9 & LOT 10 & N 35 FT OF LOT 11 BLK B05-22-30-8506-02-091

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedPhone AvailablePublicSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple