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421 Lakewood Drive

Winter Park, FL 32789

5 beds
9 baths
5,847 sqft
~3/4 acre lot
$769 per sqft
1957 build
– on site

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 courtesy of STELLAR_MLS / PREMIER SOTHEBY'S INTL. REALTY

Last checked: Checking… • Last updated Mar 22, 2025 •

MLS# O6153641 —

The Building

Year Built:

1957
New Construction:

false
Architectural Style:

Traditional
Construction Materials:

Block
Levels:

Two
Stories Total:

2
Roof:

Shingle
Foundation Details:

Block
Window Features:

Blinds
Patio And Porch Features:

Covered
Security Features:

Security System
Building Area Total:

8083
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Built-in Features
Furnished:

Negotiable
Flooring:

Carpet
Additional Rooms:

Attic
Fireplace:

true
Fireplace Features:

Gas

Room Dimensions

Living Area:

5847
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

Osceola Ave to Trismen Terrace to Detmar Dr to left on Lakewood Dr...
Latitude:

28.601888
Longitude:

-81.341421
Coordinates:

-81.341421, 28.601888

The Property

Parcel Number:

052230647601070
Property Type:

Residential
Property Subtype:

Single Family Residence
Property Condition:

Completed
Lot Features:

City Lot
Lot Size Acres:

0.72
Lot Size Area:

31500
Lot Size SqFt:

31500
Lot Size Units:

Square Feet
Total Acres:

1/2 to less than 1
Zoning:

R-1AAA
Direction Faces:

Southwest
View:

Water
View:

true
Exterior Features:

Balcony
Fencing:

Fenced
Vegetation:

Mature Landscaping
Water Source:

Public
Road Responsibility:

Public Maintained Road
Road Surface Type:

Paved
Road Frontage Type:

Street Paved
Flood Zone Code:

X
Additional Parcels:

false
Homestead:

true
Lease Restrictions:

false
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2023
Tax Lot:

7
Tax Block:

A
Tax Legal Description:

OSCEOLA SHORES SECTION 3 S/87 LOT 7 BLKA
Tax Book Number:

S-87
Tax Annual Amount:

24480.74

Beds

Bedrooms Total:

5

Baths

Total Baths:

8
Total Baths:

9
Full Baths:

7
Half Baths:

2

The Listing

Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/O6153641
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Cable Connected
Sewer:

Public Sewer

Appliances

Appliances:

Bar Fridge
Laundry Features:

Inside

Schools

Elementary School:

Lakemont Elem
Middle Or Junior School:

Maitland Middle
High School:

Winter Park High

The Community

Subdivision Name:

OSCEOLA SHORES SEC 03
Senior Community:

false
Waterview:

Lake - Chain of Lakes
Waterview:

true
Water Access:

Lake - Chain of Lakes
Water Access:

true
Water Extras:

Lift - Covered
Water Body Name:

LAKE OSCEOLA
Waterfront:

true
Waterfront Features:

Lake - Chain of Lakes
Spa:

true
Spa Features:

In Ground
Pool Private:

true
Pool Features:

Gunite
Association:

false
Ownership:

Fee Simple
Additional Water Information:

Winter Park Chain of Lakes
Waterfront Feet Total:

110

Parking

Garage:

true
Attached Garage:

true
Garage Spaces:

3
Garage Dimensions:

38x22
Carport:

false
Covered Spaces:

3
Open Parking:

true
Parking Features:

Bath In Garage

Monthly cost estimate

Asking price

$4,500,000

Expense	Monthly cost
Mortgage	$24,096
Taxes	$2,040
Insurance	$1,237
Utilities	$394 See report
Total	$27,767/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Transit Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
11/11/24 Nov 11, 2024	Pending	STELLAR_MLS	$4,500,000
9/9/24 Sep 9, 2024	Price Changed	STELLAR_MLS	$4,500,000	-5.3%
5/31/24 May 31, 2024	Price Changed	STELLAR_MLS	$4,750,000	-4.9%

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This house located in Osceola Shores, Winter Park, FL 32789 is currently pending sale for $4,500,000. 421 Lakewood Drive is a 5,847 square foot house with 5 beds and 9 baths that has been on Estately for 535 days. 421 Lakewood Drive is in the Osceola Shores neighborhood of Winter Park and has a WalkScore® of 13, making it car-dependent. This house is in the attendance area of Cornerstone Charter Academy High School, Cornerstone Charter Academy K-8, Maitland Middle School, Winter Park High School, and Lakemont Elementary School.

Listing Courtesy of: STELLAR_MLS and PREMIER SOTHEBY'S INTL. REALTY.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing 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. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.