2211 Azalea Place, Winter Park, FL 32789

$5,250,000

Luxurious waterfront estate in one of Winter Park’s most prestigious neighborhoods, offering 7,278 SF of elegant living with direct canal access to Lake Maitland. This 5-bedroom, 6.5-bath home features all en-suite bedrooms, including two on the main floor, a gourmet kitchen with Viking appliances, three fireplaces, a theater room, a… Read More game room, an office, dual laundry rooms, and dual staircases. Enjoy a heated saltwater pool and spa, summer kitchen, and pool bath. Boathouse, dock with lift, and jet ski dock included. Recent upgrades: all new AC units, pool equipment, landscaping, fencing, and gates. Fully fenced with a security system and a rare 5-car garage, this property offers privacy, space, and luxury at every turn. Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all set on almost 3/4 acre of beautifully landscaped canal-front lot with direct access to the coveted Lake Maitland and Winter Park Chain of Lakes. Spanning an impressive 7,278 square feet, this two-story masterpiece rises 40 feet and is designed for both grand-scale entertaining and luxurious everyday living. Upon entry, you're greeted by soaring ceilings and elegant architectural details that set the tone for the home’s sophisticated style. With five expansive bedrooms—all featuring en-suite bathrooms—and six full baths plus a powder room, the home offers both comfort and privacy for family and guests. Two bedroom suites are located on the main level, ideal for multigenerational living or hosting overnight visitors, while the upper level includes three additional bedroom suites, a fully equipped theater room, a study room and a spacious game or playroom. The heart of the home is the gourmet kitchen, where solid wood cabinetry, rich granite countertops, and Viking appliances come together to create a true culinary haven. The adjacent family room features one of the home’s three fireplaces and invites cozy gatherings or relaxed evenings overlooking the lush outdoor living space. The formal living and dining areas are equally impressive, offering elegant backdrops for holiday celebrations or intimate dinner parties. Step outside to discover a true private oasis. The resort-style backyard boasts a saltwater heated pool and spa with all-new equipment, a summer kitchen, and a dedicated pool bathroom—perfect for effortless indoor-outdoor living. The entire property is fenced with newly installed gates, ensuring both privacy and security. From the manicured landscaping to the serene waterfront setting, every detail has been thoughtfully curated to elevate the experience of lakeside living. For boating enthusiasts, the property includes a private boathouse, a dock with an automatic lift, and a 2 jetski dock—all providing seamless access to Lake Maitland and the entire Winter Park Chain of Lakes. Whether you're setting off for an early morning paddle, an afternoon on the water, or simply enjoying the sunset from your dock, this home offers an unrivaled connection to the natural beauty. Additional features include a 5-car garage, 2 laundry rooms, dual staircases, all-new AC units, a comprehensive security system, and three wood-burning fireplaces that add charm and warmth throughout the home. Every inch of this residence has been impeccably maintained and thoughtfully updated, offering peace of mind and modern convenience without sacrificing its classic elegance. 2211 Azalea Place is more than just a home—it’s a lifestyle. This is a rare opportunity to own a one-of-a-kind estate in one of Winter Park’s most sought-after locations, where quiet sophistication meets waterfront luxury. Read Less

Courtesy of Fortune Christie's International Real Estate 305-400-6393

Listing Snapshot

Days Online

349

Last Updated

Jun 11, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

7,278

Lot Size

0.69 Acres

Year Built

2008

MLS Number

A11824988

Additional Details

Exterior Features

"Lighting", "Balcony", "Outdoor Shower"

Appliances & Equipment

"Dishwasher", "Disposal", "Dryer", "Gas Range", "Microwave", "Refrigerator", "Washer"

Building

Built in 2008, Architectural style: "Mediterranean", Living area: 7278, Construction materials: "Block", "Stucco", Toal building area: 9111

Cooling

"Central Air", "Electric"

Doors

"French Doors"

Fence

"Fenced"

Floors

"Carpet", "Tile", "Wood"

Garage

5 spaces

Water Features

Waterfront features: "Other", "Lake Access", "Canal Front", "Lake"

Heating

"Central", "Electric"

Interior Features

"Bar", "Bedroom Layout - Split", "Built-in Features", "Closet Cabinetry", "Entrance Foyer", "High Ceilings", "Kitchen Island", "Pantry", "Vaulted Ceiling(s)", "Walk-In Closet(s)"

Lot

0.69 acres

Parking

"Attached", "Attached Garage", "Circular Driveway", "Driveway", "Garage", "Garage Door Opener", "Paver Block"

Pets Policy

Pets allowed: "No Restrictions", "Yes"

Pool

"Concrete", "Heated", "In Ground", "Pool Bath"

Property

Patio and porch features: "Porch - Open", "Porch", "Patio", View: "Canal", "Pool", "Water", Zoning: R-1AA

Roof

"Barrel"

Sewer

"Public Sewer"

Taxes

Annual amount: $36,209

Utilities

"Cable Available"

Windows

"Plantation Shutters"

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