2211 AZALEA PLACE Winter Park, FL $ 5,495,000
2211 AZALEA PLACE
$ 5,495,000
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2211 AZALEA PLACE

Winter Park, FL, 32789
$ 5,495,000
Bedrooms5 Baths6.1 Sq 7,278

Monthly Estimate*

$ 34,282

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View a Virtual Tour

Single Family Home for sale in Winter Park, FL

for $5,495,000 with 5 bedrooms and 6 full baths, 1 half bath. This 7,278 square foot home was built in 2008 on a lot size of 0.69.

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.

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Single Family Active

Price

$ 5,495,000

Bedrooms

5

Full Bath

6

Half Bath

1

Property Type

Single Family

Taxes

$ 36,208

Style

Single Family Residence

Lot Size

0.69

Year Built

2008

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6319674

Features
General
Sewer Public Sewer
Heating Central Electric Propane
Cooling Central Air
Utilities Cable Connected Electricity Connected Propane Public Sewer Connected Underground Utilities Water Connected
Roof Tile
Appliances Built-In Oven Convection Oven Cooktop Dishwasher Disposal Microwave Range Hood Refrigerator Washer
Zoning R-1AA
Garage Spaces 5
Patio/Porch Features Covered Patio Rear Porch
Pool Features Child Safety Fence Gunite Heated Outside Bath Access Salt Water Tile
Security Features Security Fencing/Lighting/Alarms Security Gate Security System Smoke Detector(s)
Construction Materials Concrete Stucco
Pets Allowed Yes
Year Built 2008
View Garden Water
Levels Two
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Waterfront Features Canal Front Lake - Chain of Lakes
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name MAITLAND SHORES
Facing Direction East
Garage Y/N true
Other Structures Boat House Outdoor Kitchen
Total Rooms 12
Full Baths 6
Status Active
Directions 2211 Azalea Pl Winter Park FL 32789
High School Winter Park High
City WINTER PARK
Body of Water LAKE MAITLAND
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 29893
Carport Y/N false
Listing Terms Cash Conventional VA Loan
Spa Features Heated In Ground
Elementary School Dommerich Elem
Land Lease Y/N false
Tax Annual Amount 36208.57
Home Warranty Y/N false
Middle/Junior High School Maitland Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://youtu.be/qzDQN0w1OiY https://youtu.be/qzDQN0w1OiY
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 1
Legal Description MAITLAND SHORES R/150 LOT 1 & E 30 FT OFLOT 2 BLK D & BEG NE COR OF SW1/4 OF NW1/4 OF SEC 32-21-30 TH RUN W 557.48 FT S30 FT TO POB N 45 DEG W 165.7 FT N 56 DEG W 96.7 FT S 26 DEG W 30.34 FT S 56 DEG E 92.9 FT S 45 DEG E 136.3 FT E 42.3 FT TO POB
Water View Canal
Water Access Type Canal - Freshwater Lake Lake - Chain of Lakes
Minimum Lease 1-2 Years
Water Access Y/N true
Additional Rooms Attic Den/Library/Office Family Room Great Room Inside Utility Media Room
Water View Y/N true
Flood Zone Code X
DockY/N true
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Interior
Interior Amenities Cathedral Ceiling(s) Ceiling Fan(s) Crown Molding Dry Bar Eating Space 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
Flooring Carpet Tile Hardwood
Furnished Y/N Unfurnished
Fireplace Features Gas Living Room Other Room Master Bedroom
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Window Features Shutters
Fireplace Y/N true
Half Baths 1
Laundry Features Inside Laundry Closet Laundry Room
Total Bedrooms 5
Total Baths 7
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Exterior
Exterior Amenities Balcony Courtyard French Doors Garden Irrigation System Lighting Outdoor Grill Outdoor Kitchen Outdoor Shower Private Mailbox
Fencing Fenced
Parking Features Circular Driveway Driveway Garage Door Opener Garage Faces Side Ground Level
Water Source Public
Lot Size Area 29893
Foundation Details Slab
Spa true
Building Area Total 9166
Lot Size Acres 0.69
Road Surface Type Asphalt Paved
Private Pool true
Waterfront Y/N true
Covered Spaces 5
Road Responsibility Public Maintained Road
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* Excluded Features
List By
Fortune International Realty

Broker

team@walas.group

Email

Affordability Calculator

$37,299
Per Month
92%
8%
0%
Monthly Principal & Interest
$34,282
Monthly Property Taxes
$3,017
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
12/19/2025$5,495,000 Listed Price

Map


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2211 AZALEA PLACE, Winter Park, FL, 32789 is a Single Family Home for sale at $5,495,000 with 7,278 sqft and a lot size of 0.69. 2211 AZALEA PLACE has 5 bedrooms, 6.1 baths, and was built in 2008. The property's zip code is 32789 which is in Winter Park, FL