421 Lakewood Drive, WINTER PARK, FL

$4,500,000

Previous Next

5

Beds

9

Baths

5,847

Square feet

0.72

Acres

About 421 Lakewood Drive

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…

Features of 421 Lakewood Drive

MLS® # O6153641
Price $4,500,000
Sold Price $4,087,500
Sold Date August 20th, 2025
Bedrooms 5
Bathrooms 9.00
Full Baths 7
Half Baths 2
Square Footage 5,847
Acres 0.72
Year Built 1957
Type Residential
Sub-Type Single Family Residence
Style Traditional
Status Sold
Show More Information

Listing Details

OfficePREMIER SOTHEBY'S INTL. REALTY

Listing Map

Neighborhood Information for 421 Lakewood Drive

Stable Population, Moderate Residential Turnover

Weather

Highs


January 71.80℉
July 92.20℉

Lows


January 72.60℉
July 72.60℉
rain icon

Precipitation


48.35

Statistics

Number of Listings

Population Age

Home Listings Prices

Nearby Schools

Great Schools School Name Distance  
Great School

Methodist School For Early Education

Private - Preschool to Kindergarten
1 Miles
Great School

St. Margaret Mary Catholic School

Catholic - Preschool to 8Th Grade - Closest Elementry School
1 Miles
Great School

Lakemont Elementary School

Public - Kindergarten to 5Th Grade
1 Miles
Great School

Winter Park Tech

Public - to
1 Miles
Great School

Brookshire Elementary School

Public - Preschool to 5Th Grade
2 Miles
Great School

Winter Park High School

Public - 9Th Grade to 12Th Grade - Closest High School
2 Miles
Great School

La Amistad

Public - Kindergarten to 12Th Grade
2 Miles

School data provided by GreatSchools

Request a Showing

Provide a valid email address.
When would you like to view this property?