533 Country Club Drive, FL533 Country Club Drive, FL533 Country Club Drive, FL
Stellar MLS
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$1,599,000

533 Country Club Drive

Winter Park, FL 32789

Listing updated: September 22, 2026 at 10:09 AM ET

Active
Stellar MLSListing courtesy of Keller Williams Winter Park · Jill Healey · MLS #O6440841 · Active · 407-545-6430
4
Beds
4
Baths
2,942
Sq Ft
0.14
Acres
2019
Built
Water accessPrivate poolFireplace$544/sqft
Single Family Residence

Property type

2019

Year built

6,119 sqft

Lot size

$544

Price / sq ft

$50/mo

HOA dues

0

Days on market

2

Garage spaces

X

Flood zone

About this home

Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Shores community, this 4-bedroom, 3.5-bath pool home offers 2,942 square feet of thoughtfully designed living space, along with exclusive access to the neighborhood’s private boat ramp and dock on Lake Killarney just across the street. Inside, soaring 10-foot ceilings, 8-foot solid doors, wood flooring and designer lighting create a bright, refined atmosphere. The inviting living room is centered around a natural gas fireplace and opens seamlessly to the pool and covered rear lanai, creating an exceptional indoor-outdoor setting for everyday living and entertaining. The gourmet kitchen impresses with 42-inch designer cabinetry, quartz countertops, tile backsplash, farmhouse sink and an oversized quartz island with generous seating. A premium Viking stainless steel appliance package includes a gas range and hood, French-door refrigerator and dishwasher, complemented by a microwave drawer. The highly desirable dual-primary-suite layout provides exceptional comfort and flexibility. The first floor offers a private bedroom with an ensuite bath, providing convenient accommodations for guests or extended stays. Upstairs, the main primary retreat features wood flooring, an oversized custom closet and a spa-inspired ensuite bath with a combined soaking tub and shower wet area. Two additional bedrooms and a spacious loft complete the second level, offering flexible space for relaxing, entertaining or working from home. Step outside to a private oasis featuring a 10-by-25-foot POOL with a sun shelf, travertine coping and a paver deck. The covered rear lanai includes a SUMMER KITCHEN equipped with a Napoleon gas grill, vented hood, granite countertops, beverage cooler and storage—perfectly designed for year-round dining, entertaining and relaxing by the pool. Recent improvements include custom window treatments throughout, upgraded office and closet installations, privacy and heat-resistant window tinting, an infrared/UV HVAC enhancement, epoxy garage floor and under-stair storage. Additional features include zoned air conditioning with Nest thermostats, a Rinnai tankless gas water heater, Low-E windows, recessed LED lighting, a metal front porch roof and pavers extending across the driveway, walkway, porch and lanai. Enjoy the best of the Winter Park lifestyle with outstanding shopping, dining and entertainment nearby. Winter Park Village is just moments away, while the boutiques, sidewalk cafés, celebrated restaurants and cultural attractions of Park Avenue are also within easy reach. Convenient access to Fairbanks Avenue, US 17-92 and I-4 provides an easy connection to Downtown Orlando, Maitland and destinations throughout Central Florida. This exceptional home brings together custom craftsmanship, beautiful finishes, an enviable lakeside setting and one of Winter Park’s most desirable locations. Schedule your private showing today and experience the custom craftsmanship, lakeside lifestyle and exceptional Winter Park location of 533 Country Club Drive.

Estimated monthly payment

Principal & interest$8,085
Property taxes$1,436
Home insurance (est.)$733
HOA dues$50

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history0 days on market

  1. Status: Active
    Sep 22, 2026
  2. Listed$1,599,000
    Sep 22, 2026
  3. Price increased$1,599,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
0
Subdivision
Lake Killarney Shores
County
Orange
Year built
2019
Living area
2,942 sq ft
Price/sq ft
$544
Building area
3,526 sq ft (Owner)
Lot size
6,119 sq ft
Lot category
0 to less than 1/4
Flood zone
X (12095C0255F)
Garage
2 spaces
Pool
Private pool
Annual taxes
$17,237 (2025)
Parcel #
01-22-29-4540-00-230
Zoning
R-2
MLS #
O6440841

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Interior Details

Bedrooms
4
Full bathrooms
3
Half bathrooms
1
Flooring
Brick, Carpet, Ceramic Tile, Hardwood, Tile
Appliances
Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Interior features
Built-in Features, Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, PrimaryBedroom Upstairs, Smart Home, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
Laundry
Inside, Laundry Room, Upper Level
Stories / Levels
Two
Direction faces
West
Fireplace
Yes

Heating & Cooling

Heating
Central
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
Yes
Parking features
Driveway, Garage Door Opener, Ground Level

HOA & Financial

HOA fee
$600 / Annually
Monthly HOA
$50/mo
Total monthly fees
$50/mo
Total annual fees
$600
HOA name
Alice Mahnke
CDD
No
Homestead exemption
Yes
Min lease term
8-12 Months
Listing terms
Cash, Conventional, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
See the attached community declarations and the City of Winter Park and Orange County for any leasing restrictions.

Exterior & Construction

Exterior features
Balcony, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sidewalk
Construction materials
Cement Siding, HardiPlank Type, Stucco
Roof
Metal, Shingle
Foundation
Block
Pool
Private pool
Water access
Yes
Road surface
Asphalt

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
Cable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Sprinkler Meter, Underground Utilities, Water Connected

Community

Pets allowed
Cats OK, Dogs OK

Schools

ElementaryCKillarney ElemGreatSchools ↗
MiddleCCollege Park MiddleGreatSchools ↗
High SchoolAEdgewater HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
Living RoomFirst25x20
Dining RoomFirst13x11
KitchenFirst13x18
Primary BedroomSecond16x16
Primary BathroomSecond10x10
Primary Bedroom 2First14x12
Bedroom 3Second12x12
Bedroom 4Second11x13
Balcony/Porch/LanaiFirst12x15
Bonus RoomSecond19x15
LaundrySecond9x6

Listing Details

Listing date
2026-09-22
On market date
2026-09-22
Original list price
$1,599,000
Occupant type
Vacant
MLS area
32789 - Winter Park
Listing AOR
Orlando Regional
Status changed
2026-09-22
Tax legal description
LAKE KILLARNEY SHORES 95/38 LOT 23

Flood risk

Minimal riskFEMA Zone XPanel 12095C0255F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From the intersection of North Orlando Avenue and Lee Road, travel west on Lee Road, turn left onto Country Club Drive and the destination will be on the left hand side.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of September 22, 2026 at 10:09 AM ET. All data is obtained from various sources and may not have been verified by 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.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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