
533 COUNTRY CLUB DRIVE, WINTER PARK, FL, 32789
Active20 days on marketListed Sep 22, 2026MLS #O6440841
About this home
533 COUNTRY CLUB DRIVE
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.
Facts & features
The home at a glance
4
Bedrooms
3.5
Bathrooms
2,942
Sqft
0.14 ac
Lot size
2
Garage
2019
Year built
Two
Levels
$544
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$10,874 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$10,874/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
+6.1%
$/sqft vs Winter Park actives
$544 vs $343
Days on market
20 vs 58 typical
Where $544/sqft sits among the 339 Winter Park actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Lake Killarney
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Park. See the full Winter Park guide →
Lake Killarney — neighborhood snapshot
Population
2,209
Median age
61
Median income
$68,693
Median home value
$396,822
Avg household
2
Households w/ children
107
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Park market
$470K → $530K
Winter Park median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
162 of 339
Winter Park actives have cut their price
Median sold price, Winter Park, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 103% above the WINTER PARK 32789 median. See the full Winter Park market guide →
Paper trail
This home's history
Reality check
What actually sold near 533 COUNTRY CLUB DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$1,535,000
507 COUNTRY CLUB DRIVE · same community
4 bd · 3.5 ba · 2,985 sqft · $514/sqft · 27 DOM
Sold · Sep ’26$1,420,000
607 ELLEN DRIVE · same community
4 bd · 4 ba · 2,812 sqft · $505/sqft · 294 DOM
Sold · Jan ’26$2,600,000
560 COUNTRY CLUB DRIVE · same community
6 bd · 6 ba · 3,946 sqft · $659/sqft · 4 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.

Your agent
Tommy Trainer
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 533 COUNTRY CLUB DRIVE — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 533 COUNTRY CLUB DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Tommy's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
533 COUNTRY CLUB DRIVE FAQs
What would the monthly payment be for 533 COUNTRY CLUB DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $10,874/mo — principal and interest, the actual property-tax bill, the $50/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 533 COUNTRY CLUB DRIVE?+
The association fee works out to $50 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 533 COUNTRY CLUB DRIVE?+
The most recent tax bill on record (2025) was $17,237. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 533 COUNTRY CLUB DRIVE?+
The listing reports pets: Cats OK, Dogs OK. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Park?+
At $1,599,000, this home is listed about 167% above the Winter Park median of $599,000. The market section on this page shows how the area is trending.
Which schools are assigned to 533 COUNTRY CLUB DRIVE?+
Killarney Elementary (elementary), Edgewater High (high), College Park Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS WINTER PARK · Jill Healey. MLS #O6440841.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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