2211 Azalea Pl

Winter Park, FL 32789

$5,495,000
Price
5
Beds
7,278 Sq. Ft.
$755 / Sq. Ft.
7,278
Sq. Ft.
$755
per Sq. Ft.
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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...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.
  1. Listed by Maggie Walas • Brokerage DRE #213971 • FORTUNE INTERNATIONAL REALTY • team@walas.group

Property Details for 2211 Azalea Place

Subdivision Name
MAITLAND SHORES
Township
21
Garage Spaces
5
View
Garden, Water
Waterfront
Yes
Water View
Canal
Furnished
Unfurnished
LISTING UPDATED: 12/07/2025 02:12 PM

Property Details for 2211 Azalea Place

StatusActive
MLS #O6319674
Days on Market230
Taxes$36,209 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2008
Lot Size0.69 AC / 29,893 SF
CountyOrange County

Location

Listing Courtesy of FORTUNE INTERNATIONAL REALTY, Maggie Walas
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Building Information for 2211 Azalea Place

Stories2Year Built2008Building Size-Lot Size0.69 AC / 29,893 SF

Payment Calculator

$29,799 per month

30 year fixed, 6.15% Interest

Principal and Interest

$26,782

Property Taxes

$3,017

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 2211 Azalea Place

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 9166.0
  • Building Area Units: Square Feet
  • Direction Faces: East
  • Directions: 2211 Azalea Pl, Winter Park, FL 32789
  • Elementary School: Dommerich Elem
  • Middle Or Junior School: Maitland Middle
  • High School: Winter Park High
  • Mls Major Change Type: Price Decrease
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 2211
  • Street Name: AZALEA
  • Street Suffix: PLACE
  • State: FL
  • City: WINTER PARK
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Ground Level
Taxes and HOA Information
  • Association Approval Required: No
  • Association: No
  • CDD: No
  • Pet Restrictions: None
  • Tax Block: D
  • Tax Book Number: R-150
  • Tax 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
  • Tax Lot: 1
  • Tax Year: 2024
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Property
Lot Information
  • Additional Parcels: No
  • Parcel Number: 322130547604010
  • Total Acreage: 1/2 to less than 1
  • Water Access: Canal - Freshwater, Lake, Lake - Chain of Lakes
  • Water Access: Yes
  • Water Body Name: LAKE MAITLAND
  • Water Extras: Boathouse, Lift - Covered, Skiing Allowed
  • Water Extras: Yes
  • Water: Boathouse, Lift - Covered, Skiing Allowed
  • Zoning: R-1AA
  • Living Area: 7278
Property and Assessments
  • Year Built Numeric: 2008
  • Flood Zone Code: X
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095cO255F
  • Home Warranty: No
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 30
  • Public Survey Section: 32
  • Dock YN: Yes
  • Dock Description: Dock - Composite, Dock - Covered, Dock w/Electric, Dock w/Water Supply, Lift
  • Dock Lift Capacity: 7000
  • Dock Year Built: 2008
  • Dock Dimensions: 15x13
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Connected, Electricity Connected, Propane, Public, Sewer Connected, Underground Utilities, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Concrete, Stucco
  • Exterior Features: Balcony, Courtyard, French Doors, Garden, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Private Mailbox
  • Fencing: Fenced
  • Foundation Details: Slab
  • Levels: Two
  • Other Structures: Boat House, Outdoor Kitchen
  • Patio And Porch Features: Covered, Patio, Rear Porch
  • Pool Dimensions: 30x20
  • Pool Features: Child Safety Fence, Gunite, Heated, Outside Bath Access, Salt Water, Tile
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Tile
  • Security Features: Security Fencing/Lighting/Alarms, Security Gate, Security System, Smoke Detector(s)
  • Spa Features: Heated, In Ground
  • Spa: Yes
  • Waterfront Features: Canal Front, Lake - Chain of Lakes
  • Waterfront Feet Total: 0
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 6
  • Additional Rooms: Attic, Den/Library/Office, Family Room, Great Room, Inside Utility, Media Room
  • Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Microwave, Range Hood, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace Features: Gas, Living Room, Other Room, Master Bedroom
  • Fireplace: Yes
  • Flooring: Carpet, Tile, Hardwood
  • Heating: Central, Electric, Propane
  • Interior Features: 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
  • Laundry Features: Inside, Laundry Closet, Laundry Room
  • Living Area Source: Appraiser
  • Living Area Units: Square Feet
  • Room Count: 12.0
  • Water View: Yes
  • Window Features: Shutters
  • Bathrooms Half: 1
Rental
Rental Information
  • Pets Allowed: Yes

Property History for 2211 Azalea Place

DateEvent & SourcePriceAppreciation
Sep 8, 2025

Price Change

MiamiRE #A11824988

$5,495,000—
Sep 8, 2025

Price Change

MFRMLS #O6319674

$5,495,000—
Aug 15, 2025

Price Change

MiamiRE #A11824988

$5,950,000—
Aug 14, 2025

Price Change

MFRMLS #O6319674

$5,950,000—
Jun 26, 2025

Listed (Active)

MiamiRE #A11824988

$6,180,000—
Jun 23, 2025

Listed (Active)

MFRMLS #O6319674

$6,180,000—
Jul 31, 2012

Expired

MFRMLS #O5042007

$2,590,000—
Apr 27, 2011

Listed (Active)

MFRMLS #O5042007

$2,995,000—
Mar 2, 2011

Withdrawn

MFRMLS #O4863536

$2,995,000—
Aug 5, 2008

Listed (Active)

MFRMLS #O4863536

$3,295,000—
Jul 15, 2008

Withdrawn

MFRMLS #O4744193

$3,349,000—
Jan 22, 2007

Listed (Active)

MFRMLS #O4744193

$3,750,000—
Jul 15, 2005

Sold (Public Record)

Public Record #161809125

$579,000—
Jul 11, 2005

Sold

MFRMLS #O4542741

$579,000—
Apr 8, 2004

Pending

MFRMLS #O4542741

—
Mar 16, 2004

Listed (Active)

MFRMLS #O4542741

$629,000—
DateEvent & SourcePrice
09/08/2025

Price Change

MiamiRE #A11824988

$5,495,000
09/08/2025

Price Change

MFRMLS #O6319674

$5,495,000
08/15/2025

Price Change

MiamiRE #A11824988

$5,950,000
08/14/2025

Price Change

MFRMLS #O6319674

$5,950,000
06/26/2025

Listed (Active)

MiamiRE #A11824988

$6,180,000
06/23/2025

Listed (Active)

MFRMLS #O6319674

$6,180,000
07/31/2012

Expired

MFRMLS #O5042007

$2,590,000
04/27/2011

Listed (Active)

MFRMLS #O5042007

$2,995,000
03/02/2011

Withdrawn

MFRMLS #O4863536

$2,995,000
08/05/2008

Listed (Active)

MFRMLS #O4863536

$3,295,000
07/15/2008

Withdrawn

MFRMLS #O4744193

$3,349,000
01/22/2007

Listed (Active)

MFRMLS #O4744193

$3,750,000
07/15/2005

Sold (Public Record)

Public Record #161809125

$579,000
07/11/2005

Sold

MFRMLS #O4542741

$579,000
04/08/2004

Pending

MFRMLS #O4542741

—
03/16/2004

Listed (Active)

MFRMLS #O4542741

$629,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 2211 Azalea Place

Taxable ValueLand-Additions-Total-
Tax Record2024$36,209 ($3,017 / month)
Home Facts
Beds5Total Finished SqFt6,399 SqFtAbove Grade Finished SqFt6,399 SqFtStories2Lot Size29,059 SqFtStyleSingle Family ResidenceYear Built2008ZoningR-1AACountyORANGEAPN32-21-30-5476-04-010Fireplace TypeHas Fireplace

Schools near 2211 Azalea Place

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Dommerich Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Maitland Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Dommerich Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Maitland Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 2211 Azalea Place, Winter Park, FL 32789

2211 Azalea Place is a single family home for sale in Winter Park, FL 32789. This property was listed for sale on June 23, 2025 by FORTUNE INTERNATIONAL REALTY, it's currently listed at $5,495,000. It has been on the market for a total of 230 days and was last sold on July 15, 2005. This listing's school district is Orange County Public Schools. Nearby schools include Dommerich Elementary School, Cornerstone Academy Charter and Maitland Middle School. 2211 Azalea Place is a 5-bed, 7-bath, 7,278 sqft single family home built in 2008.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of FORTUNE INTERNATIONAL REALTY, Maggie Walas

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 12/07/2025 02:12 PM