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.
Property Details
Property Features Property Features
MLS ID: MFRO6319674 Year Built: 2008
Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Microwave, Range Hood, Refrigerator, Washer Construction Materials: Concrete, Stucco
Cooling: Central Air Country: US
County Or Parish: Orange Direction Faces: East
Exterior Features: Balcony, Courtyard, French Doors, Garden, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Private Mailbox Fencing: Fenced
Fireplace Features: Gas, Living Room, Other, Primary Bedroom Flooring: Carpet, Tile, Wood
Foundation Details: Slab Furnished: Unfurnished
Heating: Central, Electric, Propane Laundry Features: Inside, Laundry Closet, Laundry Room
Levels: Two Listing Agreement: Exclusive Right To Sell
Listing Terms: Cash, Conventional, VA Loan Occupant Type: Vacant
Other Equipment: Irrigation Equipment Other Structures: Boat House, Outdoor Kitchen
Parking Features: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Ground Level Patio And Porch Features: Covered, Patio, Rear Porch
Pets Allowed: Yes Pool Features: Child Safety Fence, Gunite, Heated, Outside Bath Access, Salt Water, Tile
Property Sub Type: Single Family Residence Property Type: Residential
Road Responsibility: Public Maintained Road Road Surface Type: Asphalt, Paved
Roof: Tile Security Features: Security Fencing/Lighting/Alarms, Security Gate, Security System, Smoke Detector(s)
Sewer: Public Sewer Showing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTime
Spa Features: Heated, In Ground Special Listing Conditions: None
Standard Status: Active State Or Province: FL
Utilities: Cable Connected, Electricity Connected, Propane, Public, Sewer Connected, Underground Utilities, Water Connected View: Garden, Water
Water Source: Public Waterfront Features: Canal Front, Lake Privileges
Window Features: Shutters
Rooms Rooms
Primary Bedroom: 27x15 ft Bedroom 2: 23x19 ft
Bedroom 3: 15x14 ft Bedroom 4: 18x14 ft
Bedroom 5: 18x16 ft Living Room: 18x13 ft
Kitchen: 14x13 ft Den: 14x12 ft
Family Room: 21x16 ft Office: 12x21 ft
Media Room: 27x19 ft Game Room: 24x20 ft
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