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SoldSingle Family ResidenceSold

421 Lakewood Drive

Winter Park, FL 32789

$4,087,500

  • 5Beds
  • 9Baths7 full, 2 half
  • 5,847Sq Ft
  • $699Per Sq Ft
  • 0.72Acres
  • 1957Built
Subdivision
Osceola Shores Sec 03
County
Orange
MLS®
O6153641

Overview

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…

Listing Snapshot

Price
$4,087,500
Days On Site
N/A
Bedrooms
5
Inside Area (SqFt)
5,847 sqft
Total Baths
9
Full Baths
7
Partial Baths
2
Lot Size
0.72 Acres
Year Built
1957
MLS® Number
O6153641
Status
Sold
Property Tax
$24,480.74 (2023)
HOA/Condo/Coop Fees
N/A
Sq Ft Source
Public Records

Property Details

General Features

17 items
Acres
0.72
Attached Garage
Yes
Direction Faces
Southwest
Foundation
Block, Slab
Garage
Yes
Garage Spaces
3
Levels
Two
Number Of Stories
2
Parking
Circular Driveway, Garage Door Opener, On Street, Oversized, Garage, Workshop in Garage, Attached
Property Sub Type
Single Family Residence
Security
Security System, Security System Owned, Smoke Detector(s)
Sewer
Public Sewer
SqFt Total
8,083
Style
Traditional
Utilities
Cable Available, Natural Gas Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Water Source
Public
Zoning
R-1AAA

Interior Features

26 items
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Freezer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer
Basement
Crawl Space
Cooling
Central Air
Fireplace
Yes
Fireplace Features
Gas, Wood Burning
Flooring
Carpet, Wood
Furnished
Negotiable
Heating
Central, Electric
Interior
Built-in Features, Crown Molding, Eat-in Kitchen, Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Spa
Yes
Window Features
Window Coverings, Blinds, Double Pane Windows, Drapes, Shutters, Window Treatments

Rooms

RoomDimensionsLevelFeatures
Bedroom 114x11Second
Bedroom 218x18Second
Bedroom 315x13Second
Bedroom 415x13Second
Bedroom 511x10First
Den16x12First
Dinette14x14First
Dining Room31x11First
Game Room31x14Second
Kitchen25x13First
Living Room30x20First
Loft16x14Second
Master Bedroom26x20First
Media Room23x14First

Exterior Features

15 items
Construction Details
Block, Frame
Exterior
Balcony, Lighting, Rain Gutters
Fencing
Fenced
Lot Features
Irregular Lot, Paved, Waterfront
Patio And Porch
Covered, Enclosed, Front Porch, Patio, Porch, Rear Porch
Pool Features
Gunite, In Ground, Private
Private Pool
Yes
Roof
Shingle
Spa
Yes
Spa Features
In Ground
View
Lake, Water
Waterfront
Yes
Waterfront Features
Lake Privileges
Waterview
Lake, Water
Windows/Doors
Window Coverings, Blinds, Double Pane Windows, Drapes, Shutters, Window Treatments

Community Features

3 items
MLS Area
32789 - Winter Park
Township
22
Roads
Asphalt

Location

421 Lakewood Drive, Winter Park, FL 32789 · 32789 - Winter Park

Neighborhood & Commute

ZIP Code 32789

Median household income
$110,150
Income per person
$78,898
Households
12,171
Average household size
2.08
Median age
44.5

Source: Walk Score.

Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.

Schools

Elementary School
Lakemont Elem
Middle School
Maitland Middle
High School
Winter Park High

Price & Status History

  1. Listing updated with changes from the MLS®
  2. Status changed to Closed
  3. Price changed to $4,500,000

Friends & Family

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Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY (407) 629-4446

Stellar MLS

Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.

Last checked: 2026-11-07 01:14 PM EST

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