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2211 Azalea Place

Winter Park, FL 32789
  • $5,495,000
  • STATUS: Active
  • ON SITE: 263 Days
  • ID#: O6319674
UPDATED: 68 min ago
$5,495,000
  • 5
    BEDS
  • 0.69
    ACRES
  • 6
    BATHS
  • 1
    1/2 BATHS
  • 7,278
    SQFT
  • $755
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
2008
County:
Area:

School Information

Elementary School:
Middle School:
High School:

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 neighborhoodsjust 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 bedroomsall featuring en-suite bathroomsand 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 bathroomperfect 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 dockall 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 homeit'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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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-03-14T17:45:11.057.
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2211 Azalea Place Winter Park, FL 32789

  • Price: $5,495,000
  • Status: Active
  • On Site: 263 Days
  • Updated: 68 min ago
  • ID#: O6319674
5
Beds
6
Baths
1
½ Baths
0.69
Acres
7,278
SQFT
$755
$/SQFT
2008
Built
Neighborhood:
Maitland Shores
County:
Orange
Area:
Winter Park
Elementary School:
Dommerich Elem
Middle School:
Maitland Middle
High School:
Winter Park High
Property 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 neighborhoodsjust 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 bedroomsall featuring en-suite bathroomsand 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 bathroomperfect 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 dockall 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 homeit'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.
Exterior Features

Attached Garage Yn Yes Carport Yn No Construction Materials ConcreteStucco Covered Spaces 5 Direction Faces East Exterior Features BalconyCourtyardFrench DoorsGardenIrrigation SystemLightingOutdoor GrillOutdoor KitchenOutdoor ShowerPrivate Mailbox Fencing Fenced Foundation Details Slab Open Parking YN Yes Other Structures Boat HouseOutdoor Kitchen Parking Features Circular DrivewayDrivewayGarage Door OpenerGarage Faces SideGround Level Patio And Porch Features CoveredPatioRear Porch Pool Features Child Safety FenceGuniteHeatedOutside Bath AccessSalt WaterTile Pool Private Yn Yes Road Surface Type AsphaltPaved Roof Tile Spa Features HeatedIn Ground Spa YN Yes View GardenWater Water Access Canal - FreshwaterLakeLake - Chain of Lakes Water Access Yn Yes Water Body Name LAKE MAITLAND Water Extras BoathouseLift - CoveredSkiing Allowed Water Extras Yn Yes Water View Canal Water View Yn Yes Waterfront Features Canal FrontLake - Chain of Lakes Waterfront Feet Total 0 Waterfront Yn Yes

Interior Features

Additional Rooms AtticDen/Library/OfficeFamily RoomGreat RoomInside UtilityMedia Room Appliances Built-In OvenConvection OvenCooktopDishwasherDisposalMicrowaveRange HoodRefrigeratorWasher Building Area Total 9166 Cooling Central Air Cooling YN Yes Fireplace Features GasLiving RoomOther RoomMaster Bedroom Fireplace Yn Yes Flooring CarpetTileHardwood Furnished Unfurnished Heating CentralElectricPropane Heating YN Yes Interior Features Cathedral Ceiling(s)Ceiling Fan(s)Crown MoldingDry BarEating Space In KitchenHigh CeilingsKitchen/Family Room ComboOpen FloorplanPrimary Bedroom Main FloorSmart HomeSolid Surface CountersSolid Wood CabinetsSplit BedroomStone CountersThermostatTray Ceiling(s)Vaulted Ceiling(s)Walk-In Closet(s)Window Treatments Laundry Features InsideLaundry ClosetLaundry Room Levels Two Rooms Primary Bedroom (Walk-In Closet(s)) Bedroom 3 (Walk-In Closet(s)) Bedroom 2 (Walk-In Closet(s)) Bedroom 4 (Walk-In Closet(s)) Bedroom 5 (Granite CountersWalk-In Closet(s)) Living Room Den Kitchen Office Family Room Media Room Game Room Sewer Public Sewer Stories Total 2 Water Source Public Window Features Shutters

Property Features

Association Approval Required Yn No Association Yn No Cdd Yn No Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Listing Terms CashConventionalVA Loan Minimum Lease 1-2 Years New Construction Yn No Ownership Fee Simple Pets Allowed Yes Property Sub Type Single Family Residence Realtor Info Brochure AvailableDocs AvailableSignSurvey Available Security Features Security Fencing/Lighting/AlarmsSecurity GateSecurity SystemSmoke Detector(s) Senior Community Yn No Special Listing Conditions None Tax Annual Amount 36208.57 Total Annual Fees 0 Total Monthly Fees 0 Utilities Cable ConnectedElectricity ConnectedPropanePublicSewer ConnectedUnderground UtilitiesWater Connected Zoning R-1AA


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of FORTUNE INTERNATIONAL REALTY: 305-400-6393.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-03-14T17:45:11.057.
 
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