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2211 Azalea Pl, Winter Park, FL 32789

$6,180,000

Elegant two-story home showcasing meticulous landscaping, iron gate, and distinctive Mediterranean-style architecture at 2211 Azalea Pl, Winter Park, FL 32789
  • Bedrooms

    5

  • Baths

    7

  • Sq. Feet

    7278

  • Year Built

    2008

  • Days On Market

    2

  • $/SqFt

    $849

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Home Description

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.

  • Elementary School: Dommerich Elem
  • Middle School: Maitland Middle
  • High School: Winter Park High
  • Private Pool: True
  • Pool Features: Child Safety Fence,Gunite,Heated,Outside Bath Access,Salt Water,Tile
  • Spa Features: Heated,In Ground
  • Water View: Canal
  • Water Name: LAKE MAITLAND
  • Water Frontage: Canal Front,Lake Privileges
  • Water Feet: 0
  • Water Extras: Boathouse,Lift - Covered,Skiing Allowed
  • Water Access: Canal - Freshwater,Lake,Lake - Chain of Lakes
  • Interior Features: Cathedral Ceiling(s),Ceiling Fans(s),Crown Molding,Dry Bar,Eat-in Kitchen,High Ceilings,Kitchen/Family Room Combo,Open Floorplan,Primary Bedroom Main Floor,Smart Home,Solid Surface Counters,Solid Wood Cabinets,Split Bedroom,Stone Counters,Thermostat,Tray Ceiling(s),Vaulted Ceiling(s),Walk-In Closet(s),Window Treatments
  • Appliances: Built-In Oven,Convection Oven,Cooktop,Dishwasher,Disposal,Microwave,Range Hood,Refrigerator,Washer
  • Fireplace Desc: Gas,Living Room,Other,Primary Bedroom
  • Floor Covering: Carpet,Tile,Wood
  • Additional Rooms: Attic,Den/Library/Office,Family Room,Great Room,Inside Utility,Media Room
  • Exterior Features: Balcony,Courtyard,French Doors,Garden,Lighting,Outdoor Grill,Outdoor Kitchen,Outdoor Shower,Private Mailbox
  • Exterior Contruction: Concrete,Stucco
  • Foundation: Slab
  • Front Exposure: East
  • Roof: Tile
  • Building Sqft: 9166

Available now at $6,180,000

Approximate Room Sizes / Descriptions

Living Room18x13FirstWood
Kitchen14x13FirstTile
Den14x12SecondCarpet
Family Room21x16FirstTile
Office12x21SecondWood
Media Room27x19SecondCarpet
Game Room24x20SecondCarpet
Primary Bedroom27x15FirstWood
Bedroom 223x19FirstWood
Bedroom 315x14SecondCarpet
Bedroom 418x14SecondCarpet
Bedroom 518x16SecondCarpet
  • Attached Garage: True
  • Garage: True
  • Garage Spaces: 5
  • Garage Feature: Circular Driveway,Driveway,Garage Door Opener,Garage Faces Side,Ground Level
  • Carport: False
  • Carport Spaces: 0
  • Air Conditioning: Central Air
  • Heating: Central,Electric,Propane
  • Utilities: Cable Connected,Electricity Connected,Propane,Public,Sewer Connected,Underground Utilities,Water Connected
  • Lot Sqft: 29893.00
  • Lot Acres: 0.6900
  • Total Acre: 1/2 to less than 1
  • Lot Num: 1
  • Senior Community: False
  • Style: Single Family Residence
  • Building Num Floors: 2
  • Pets Allowed: Yes
  • : 305-400-6393

Neighborhood

The average asking price of a 5 bedroom Winter Park home in this zip code is $2,879,361 (53.4% less than this home).

This home is priced at $849/sqft, which is 23.2% less than similar homes in the 32789 zip code.

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Financial

  • Approx Payment:$30,064*
  • Taxes:$36,209

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at (407) 967-1435 and speak with one of our real estate consultants.

Listing Courtesy of FORTUNE INTERNATIONAL REALTY. For information or to schedule a viewing of this property (MLS# O6319674), call: 407-967-1435

2211 Azalea Pl, Winter Park FL is a single family home of 7278 sqft and is currently priced at $6,180,000 . This single family home has 5 bedrooms. A comparable home for sale at 1820 Englewood Rd in Winter Park is listed at $3,300,000. In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos, New Homes and Foreclosures in Winter Park, FL. Tuscania, Windsong Preserve Point and Kronenberger are nearby neighborhoods. MLS O6319674 has been posted on this site since 6/23/2025 (today).

2025 6/24/2025.

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