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Overview

5 bd6 ba5,152 sqft3 car garageSingle Family
TypeSingle Family
HOANone listed
Built2008
Lot14,374 sqft
Living area5,152 sqft
Price / sqft$1,087
Garage3 car

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About this home

Built-in FeaturesCathedral Ceiling(s)Ceiling Fans(s)Crown MoldingDry BarEat-in KitchenHigh CeilingsKitchen/Family Room Combo

2228 Azalea Pl is a 2008-built home in Maitland Shores First Add, Winter Park. Inside you'll find 5 bedrooms, 6 bathrooms, and 5,152 square feet of living space. Listed at $5,600,000 (about $1,087/sqft), 88 days on market. Flood zone x - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

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

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The essentials

Built
2008
Price / sqft
$1,087
On market
120 days
Annual tax
$26,904
Flood zone
X · Low risk
Lot
14,374 sqft
Type
Single Family Residence

At a glance

Single family
Built 2008
Private pool
In Ground
3 car garage
Circular Driveway
0.33 acres
Lot size
5,152 sqft
Living area

Payment

Est. monthly payment
$34,248/mo
Down payment (20%)
$1,120,000
Property taxes
$2,242/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
2008
Lot
14,374 sqft
Cooling
Central Air, Zoned
Heating
Central, Electric, Heat Pump, Zoned
Parking
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side
Pool
In Ground
Days on Market
120
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
Awning(s)
Balcony
Lighting
Private Yard
Bar Fridge
Dishwasher
Disposal
Dryer
Ice Maker
Microwave
Range
Range Hood
Refrigerator
Tankless Water Heater
Wine Refrigerator
Elementary
Dommerich Elem
Middle
Maitland Middle
High
Winter Park High

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on file Flood Zone x
Annual Tax (2025)
$26,904
Parcel #
32-21-30-5478-05-040

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Maitland Shores First Add
County
Orange
MLS Area
32789 - Winter Park
Lot Size
14,374 sqft
Corner Lot

Price history

Date
Event
Price
6/12/2026
Listed for sale
Source: Stellar MLS #O6416342
$5,600,000
$1,087/sqft

Neighborhood

2228 Azalea Pl
Winter Park, FL, 32789 · 32789 - Winter Park

Market insights

Offer Insights

Choose an offer strength

List price: $5,600,000
$5.44M – $5.60M
97.2% – 100% of listTops out right at the list price
80% of listList price
96 of the last 190 home closings in 32789 landed at this number or higher (51%). The median one sat 21 days before it went under contract, and this one is on day 120.

Sample: 190 closed home sales in 32789 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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Calculator

Est. monthly payment
$34,248/mo
Principal & interest$29,206
Property taxes$2,242
Insurance$2,800
Down payment20% · $1,120,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$5,600,000

$1,087 per sq ft

Beds and baths

5 beds, 6 baths

Size

5,152 sq ft

Time on market

120 days

Year built

2008

Monthly payment

About $34,248/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $26,904 annual tax bill, insurance.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

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Brokered byCOMPASS FLORIDA LLCListing agent: Quentin Green, IIListing data from Stellar MLS, MLS# O6416342.

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