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Single family home for sale at 2228 Azalea Pl, Winter Park, FL 32789 | MLS# O6416342 | Listing updated on 2026-09-23
Photo 1 of Single family home for sale at 2228 Azalea Pl, Winter Park, FL 32789 | MLS# O6416342 | Listing updated on 2026-09-23
Photo 2 of Single family home for sale at 2228 Azalea Pl, Winter Park, FL 32789 | MLS# O6416342 | Listing updated on 2026-09-23
Photo 3 of Single family home for sale at 2228 Azalea Pl, Winter Park, FL 32789 | MLS# O6416342 | Listing updated on 2026-09-23
Photo 4 of Single family home for sale at 2228 Azalea Pl, Winter Park, FL 32789 | MLS# O6416342 | Listing updated on 2026-09-23
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$5,600,000

Monthly Est:$27,873

  • Beds Icon5 Beds
  • Beds Icon
    6 Baths
  • Beds Icon5,152sqft

2228 Azalea Pl, Winter Park, FL 32789

$27,873/moEst:

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  • Single Family Residence

  • Built in 2008

  • $-- HOA

  • 14,374 sqft lot

  • $1,087/sq.ft

Description

This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. One or more rooms virtually staged

  • Houzeo last checked: 22 minutes ago
  • Listing updated: September 23, 2026 at 6:06 pm
  • Listing Provided by: Quentin Green, II (773) 418-5359 | COMPASS FLORIDA LLC (407) 203-9441
  • Source: Stellar MLS-FL | MLS#: O6416342 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    2

  • County

    Orange County

  • City

    Winter Park

  • Neighborhood

    --

  • Year Built

    2008

  • HOA Fees

    -

  • Finished Area

    5,152 sqft

  • Lot Size

    14,374 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6416342

  • MLS Status

    Active

  • Days on Market

    106

  • Cumulative Days on Market

    88

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Location

HOA Management

MAITLAND SHORES PROTECTIVE ASSOCIATION

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 6

  • Living Room

    Level: First

    Area: 460.00 Square Feet

    Dimensions: 23x20

  • Media Room

    Level: Second

    Area: 280.00 Square Feet

    Dimensions: 20x14

  • Bedroom 4

    Level: Second

    Area: 195.00 Square Feet

    Dimensions: 13x15

  • Bedroom 3

    Level: Second

    Area: 208.00 Square Feet

    Dimensions: 13x16

  • Bedroom 2

    Level: Second

    Area: 247.00 Square Feet

    Dimensions: 19x13

  • Bedroom 1

    Level: Second

    Area: 266.00 Square Feet

    Dimensions: 19x14

  • Primary Bathroom

    Level: First

    Area: 240.00 Square Feet

    Dimensions: 15x16

  • Primary Bedroom

    Level: First

    Area: 342.00 Square Feet

    Dimensions: 18x19

  • Laundry

    Level: First

    Area: 42.00 Square Feet

    Dimensions: 6x7

  • Balcony/Porch/Lanai

    Level: First

    Area: 390.00 Square Feet

    Dimensions: 30x13

  • Dining Room

    Level: First

    Area: 208.00 Square Feet

    Dimensions: 13x16

  • Den

    Level: First

    Area: 195.00 Square Feet

    Dimensions: 15x13

  • Kitchen

    Level: First

    Area: 240.00 Square Feet

    Dimensions: 15x16

  • Dinette

    Level: First

    Area: 176.00 Square Feet

    Dimensions: 16x11

  • Family Room

    Level: First

    Area: 380.00 Square Feet

    Dimensions: 20x19

Interior

  • Appliances

    Bar Fridge, Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Wine Refrigerator

  • Exterior Features

    Awning(s), Balcony, Lighting, Private Yard

  • Flooring

    Carpet, Marble, Tile, Wood

  • Heating

    Central, Electric, Heat Pump, Zoned

  • Interior Features

    Built In Features, Cathedral Ceiling(s), Ceiling Fans(s), Crown Molding, Dry Bar, Eat In Kitchen, High Ceilings, Kitchen/family Room Combo, Primary Bedroom Main Floor, Walk In Closet(s), Wet Bar

  • Sewer

    Aerobic Septic

  • Cooling

    Central Air, Zoned

Construction

  • Year Built

    Year Built: 2008

  • Home type

    Single Family Residence

  • Construction Materials

    Block, Stucco

  • Property Condition

    Completed

  • Architectural Style

    French Provincial

  • Roof

    Metal, Slate

  • Foundation Details

    Slab

Utilities & Energy

  • Laundry Features

    Inside

  • Utilities

    Electricity Connected, Propane, Sprinkler Meter, Underground Utilities, Water Connected

  • Fireplace Features

    Family Room, Gas, Other

  • Water Source

    Public

  • Security Features

    Security System

  • Pool Features

    In Ground

  • Parking Features

    Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side

Other Features

  • Subdivision Name

    Maitland Shores First Add

  • Lot Features

    Corner Lot

  • Vegetation

    Bamboo, Mature Landscaping, Oak Trees, Trees/landscaped

  • Patio And Porch Features

    Covered, Deck, Patio, Rear Porch

Price History

DateEventPrice

06/27/2026

Source: mls_logoStellar MLS-FL #MFRO6416342

Listed for Sale

$5,600,000 +12.00%

$1,087/sqft

05/07/2025

Source: mls_logoStellar MLS-FL #MFRO6250411

Listing Removed

$5,000,000 -7.41%

$970/sqft

10/18/2024

Source: mls_logoStellar MLS-FL #MFRO6250411

Listed for Sale

$5,400,000

$1,048/sqft

07/17/2024

Source: mls_logoStellar MLS-FL #MFRO6120809

Listing Removed

$5,400,000 +217.83%

$1,048/sqft

06/27/2014

Source: mls_logoStellar MLS-FL #MFRO5232703

Price Increased

$1,699,000 +25.85%

$330/sqft

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Nearby Homes

Based on information from Stellar MLS® through Oct 12, 2026, 10:30AM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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