$4,500,000
5 Bed
9 Bath
5,847
0.72 Acre Lot

421 Lakewood Drive, Winter Park, Florida 32789

  • Residential Property Type
  • 5,847 Square Footage
  • Garage Door Opener Cars Garage
  • 1957 Year Built
Property Description

This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the picturesque shores of Lake Osceola. This exquisite home invites you in with a grand circular driveway and meticulous, landscaped grounds, combined with elevated panoramic views from a spacious 3/4 acre lot, with approx. 140 feet on the street and approx.. 110 feet of prime lake frontage. This property offers a sense of privacy, tranquility and breathtaking views capturing both northern sunrises & sunsets…
Inside, you’ll find extensive renovations, over the years, that have elevated the space enhanced with Wolfe-Rizor Interior Design elements… There is plenty of natural light throughout, with extensive windows, numerous French doors and a thoughtful layout that seamlessly blends indoor and outdoor living spaces. The primary level includes a defined foyer entry, secluded library/home office, kitchen, gathering room, formal living and dining rooms. The chef’s kitchen is thoughtfully designed and enhanced by an expansive island, commercial grade range, lake side breakfast room, and catering area for creating culinary experiences in hosting family and friends. The lavish living room includes room for a grand piano and has its own fireplace open to an expansive 30’ long dining room with direct lake views… along with a screened lanai…
The primary suite is conveniently located on the ground floor, offering a private expansive retreat with a sitting area and serene, picturesque lake views. The luxurious primary bathroom provides a spa-like experience including modern fixtures, his/her separate baths, and a generous walk-in closet/dressing room. The main level also includes a potential 6th bedroom used previously for a caretaker’s quarters tucked away by the garage entry…
The upstairs living areas, include 4 additional bedroom suites (generous sizes) located on the second floor with a couple of bonus/flex rooms and sitting area… When you’re not savoring the indoor elegance, step outside to enjoy the lakefront living with entertaining terrace, tropical pool, sprawling lawn with retaining walls, boathouse and majestic cypress, oak & palm trees to enhance the lakefront lifestyle…
Located on private, quiet street with oversized 3-car garage… Note: roof replaced in 2021. All within walking distance to downtown Winter Park and famed Park Avenue…

Basic Details
Residential
For Sale
O6153641
$4,500,000
Water
5
9
2
5,847
1957
0.72 Acre
Active
7
Single Family Residence
: Shingle
1
Features
: Gunite, In Ground, Lighting
: Central, Electric
: Central Air
: Fenced
: Wood Burning, Gas
: Covered, Front Porch, Rear Porch, Patio, Porch, Enclosed
: Garage Door Opener, Oversized, Circular Driveway, On Street, Ground Level, Workshop in Garage, Bath In Garage, Garage
: Lighting, Rain Gutters, Balcony, Private Mailbox, French Doors, Shade Shutter(s)
: Carpet, Wood
: Walk-In Closet(s), Primary Bedroom Main Floor, Solid Surface Counters, Thermostat, Ceiling Fans(s), Eat-in Kitchen, Split Bedroom, Window Treatments, Solid Wood Cabinets, Crown Molding, Built-in Features
: Laundry Room, Inside
1
: Public Sewer
: Public, Electricity Connected, Cable Connected, Natural Gas Connected, Sewer Connected, Water Connected, Sprinkler Well
: Lake Privileges
: Shutters, Blinds, Window Treatments, Double Pane Windows, Rods, Drapes
: Traditional
Appliances
: Dishwasher, Microwave, Range, Disposal, Electric Water Heater, Dryer, Refrigerator, Washer, Bar Fridge, Range Hood, Tankless Water Heater, Built-In Oven, Freezer
Address Map
US
FL
Orange
Winter Park
OSCEOLA SHORES SEC 03
32789
LAKEWOOD
421
DRIVE
W82° 39' 30.5''
N28° 36' 5.6''
Southwest
Osceola Ave to Trismen Terrace to Detmar Dr to left on Lakewood Dr...
32789 - Winter Park
R-1AAA
Neighborhood
Lakemont Elem
Winter Park High
Maitland Middle
Additional Info
PREMIER SOTHEBY'S INTL. REALTY
Mick Night
$0
$0
Additional Information
: Block, Frame
: Slab, Crawlspace, Block
3
: Two
: Paved, Oversized Lot, City Limits, Irregular Lot
2023-10-31
4750000
2
https://www.propertypanorama.com/instaview/stellar/O6153641
LAKE OSCEOLA
: Public
1
8083
Financial
24480.74
Listing Information
261010033
261014339
Active
2025-06-02T16:32:08Z
Stellar
: None
2025-05-16T19:24:22Z
John Pinel
261071963
261014339
PREMIER SOTHEBY'S INTL. REALTY
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Contact Agent
Contact Us
407-615-0866