Waterfront - Primary on Main - Adult 55+
Address
2211 Azalea Place, Winter Park, FL
Price
$ 5,250,000
Property Attributes
- MLS#A11824988
- TypeSingle Family
- Listing Status Active
- CountyOrange
- CityWinter Park
- Area5940 - Other Florida County
- NeighborhoodMAITLAND SHORES
- Zip32789
- Style
- Year Built2008
- Taxes$ 36209
- Price$ 5,250,000
- Bedrooms5
- Full Bathrooms6
- Half Bathrooms1
- Sqr Footage7278
- Lot Size0.69 Acres
Data Source:
Beaches MLS (FL)
Property Description
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 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.
| Price History | |
|---|---|
| 6/9/2026 | Listed $5,250,000 |
General Features
| Sewer | Public Sewer |
|---|---|
| Heating | Central,Electric |
| Cooling | Central Air,Electric |
| Utilities | Cable Available |
| Possession | Close Of Escrow |
| Roof | Barrel |
| Appliances | Dryer,Dishwasher,Disposal,Gas Range,Microwave,Refrigerator,Washer |
| Garage Spaces | 5 |
| Patio/Porch Features | Open,Patio,Porch,Balcony |
| Architectural Style | Mediterranean |
| Pool Features | Concrete,Heated,In Ground,Outside Bath Access |
| Construction Materials | Block,Stucco |
| Pets Allowed | No Pet Restrictions,Yes |
| Year Built | 2008 |
| View | Canal,Pool,Water |
| Stories Count | 2 |
| Levels | Two |
| Property Subtype | Single Family Residence |
| Tax Year | 2024 |
| Waterfront Features | Canal Front,Lake Front,Lake Privileges,Other |
| County | Orange |
| Property Type | Residential |
| Association Amenities | None |
| Attached Garage | true |
| Subdivision Name | MAITLAND SHORES |
| Facing Direction | East |
| Garage Y/N | true |
| Other Structures | Boat House |
| Full Baths | 6 |
| Status | Active |
| Directions | 2211 Azalea Pl, Winter Park, FL 32789 |
| City | Winter Park |
| Senior Community Y/N | true |
| MLS Area | 5940 - Other Florida County |
| Spa Features | Heated,In Ground |
| Tax Annual Amount | 36209 |
| Virtual Tour | https://youtu.be/qzDQN0w1OiY |
| Standard Status | Active |
| Occupancy Type | Vacant |
| Property Sub Type Additional | Single Family Residence |
| PostalCity | Winter Park |
| 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 DE |
Interior Features
| Interior Amenities | Built-in Features,Bathtub,Closet Cabinetry,Dining Area,Separate/Formal Dining Room,Dual Sinks,Entrance Foyer,High Ceilings,Kitchen Island,Main Level Primary,Pantry,Sitting Area in Primary,Split Bedrooms,Soaking Tub,Separate Shower,Vaulted Ceiling(s),Bar,Walk-In Closet(s) |
|---|---|
| Flooring | Carpet,Tile,Wood |
| Furnished Y/N | Unfurnished |
| Total Stories | 2 |
| Air Conditioning Y/N | true |
| Heating Y/N | true |
| Window Features | Plantation Shutters |
| Fireplace Y/N | true |
| Half Baths | 1 |
| Total Bedrooms | 5 |
| Entry Level | 1 |
| Total Baths | 7 |
Exterior Features
| Exterior Amenities | Balcony,Lighting,Outdoor Living Area,Outdoor Shower |
|---|---|
| Fencing | Fenced |
| Parking Features | Attached,Circular Driveway,Driveway,Garage,Garage Door Opener,Paver Block |
| Water Source | Public |
| Lot Size Area | 29893 |
| Spa | true |
| Building Area Total | 9111 |
| Lot Size Acres | 0.69 |
| Frontage Length | 23.00 |
| Frontage Type | Waterfront |
| Waterfront Y/N | true |
| Covered Spaces | 5 |
| Door Features | French Doors |
Amenities
- Foreclosure
- Views
- Short Sale
- New Construction
- Adult 55+
- Lease To Own
- No HOA Fees
- Furnished
- Primary On Main
- Air Conditioning
- Seller Finance
- Green
- Fixer Upper
- Horse
- Golf
- Fireplace
- Deck
- Garage
- Basement
- Pool
Property vs Single Family Average in 32789
Price
Taxes
Year Built
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Data Last Updated: September 21, 2026 4:00 AM UTC
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