421 Lakewood Drive
Winter Park, FL 32789

  • 5 beds
  • 9 baths
  • 5,847 sqft
  • ~3/4 acre lot
  • $854 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…

My Florida Regional MLS DBA Stellar MLS logo Listing courtesy of STELLAR_MLS / PREMIER SOTHEBY'S INTL. REALTY

Last checked: Checking… • Last updated Apr 19, 2024 •

MLS# O6153641 —

Monthly cost estimate

421 Lakewood Drive

Asking price

$4,995,000

Expense Monthly cost
Mortgage

$26,746

Taxes $2,040
Insurance $1,373
Utilities $394 See report
Total $30,553/mo.*
*This is an estimate

Explore the Area

Map View Options

My Commute

Never miss new listings

Be the first to know about new listings between $3,000,000–the sky in this neighborhood

* indicates a required field

We’ll never spam you or sell your details. You can unsubscribe whenever you’d like.

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

Worst Moderate Best

Sale history

Date Event Source Price % Change
3/10/24
Relisted STELLAR_MLS $4,995,000 -4.9%
2/25/24
Pending STELLAR_MLS $5,250,000
1/15/24
Price Changed STELLAR_MLS $5,250,000 -4.5%

Finding records…

No additional history available

If new records are added for this property, we’ll share them here.

Want to see this home?


When do you want to see it?

Or Call Us 1-800-241-3327

Want a closer look?

Go see 421 Lakewood Drive

421 Lakewood Drive

Or Call Toll Free 1-800-241-3327

We guarantee that we’ll never spam you.

* indicates a required field

Yes, I would like more information from Estately. Please use and/or share my information with Estately and their designated agent to contact me about my real estate needs.
By submitting this request, I agree Estately and their designated agent may contact me by phone or text message about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to the Terms of Use and Privacy Policy.

More homes

Newest listings in Winter Park, FL

Similar sold homes

This house located in Osceola Shores, Winter Park, FL 32789 is currently for sale for $4,995,000. 421 Lakewood Drive is a 5,847 square foot house with 5 beds and 9 baths that has been on Estately for 188 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 Lakemont Elementary School, Winter Park High School Freshman Campus, Winter Park High School, Maitland Middle School, Cornerstone Charter Academy K 8, and Cornerstone Charter Academy High School.

My Florida Regional MLS DBA Stellar MLS logo Listing Courtesy of: STELLAR_MLS and PREMIER SOTHEBY'S INTL. REALTY.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2024.

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.

The offer of compensation listed above is made to, and can only be accepted by, participants of the multiple listing service in which this listing is filed.

Copyright © 2024 Estately, Inc. Data displayed here has not been verified by Estately.