ParkingBath In Garage, Circular Driveway, Garage Door Opener, Ground Level, On Street, Oversized, Split Garage, Workshop in Garage
Attached Garage3 spaces
Year Built1957
HeatingCentral, Electric
CoolingCentral Air
WaterfrontLake Front
FireplaceGas, Wood Burning
ViewWater
Private PoolYes
MLS #O6153641
Lot Size0.72 Acres
StatusSale Pending (Pending)
About 421 Lakewood Dr
Under contract-accepting backup offers. 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…
Property Details
Property Features
Property Information:
Architectural Style: Traditional
Year Built: 1957
Stories: 2
Living Area: 5,847 SqFt
Listing Office:
Office Name: PREMIER SOTHEBY'S INTL. REALTY
Office Phone: (407) 644-3295
Listing Agent: Mick Night
Interior Features
Interior Information:
Appliances: Bar Fridge, Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Freezer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer
This property is $4.0M more than the Median Sold Price and $480/SqFt more than other homes in Winter Park, FL.
Based on homes sold in the last 12 months
MLS Details
MLS Information:
MLS Name: MFRMLS
MLS Number: #O6153641
Listing Office:
Office Name: PREMIER SOTHEBY'S INTL. REALTY
Office Phone: (407) 644-3295
Listing Agent: Mick Night
Listings courtesy of Stellar MLS as distributed by MLS GRID.
All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Copyright 2025 My Florida Regional Multiple Listing Service DBA Stellar MLS. The real estate listing data marked with this icon comes from the IDX program of the Stellar MLS system. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided exclusively for consumers’ personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Properties displayed may be listed or sold by various participants in the MLS. Data displayed may be a portion of, and not a complete set of all listings published in the MLS. Last updated on: 1/14/2025, 10:49:51 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Property Sales & Tax
Listing History
DATE
EVENT
PRICE
Jun 05, 1997
Jun 05, 1997Home Sold
$1,105,000
Tax History
YEAR
PROP. TAX
ASSESSMENT
2020
$23,031
$1,475,038
2018
$22,782
$1,414,990
2017
$22,607
$1,385,886
History based on county public records data.
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Schools
Schools Nearby
The school rating is a score out of 10, where 10 is the highest and 1 is the lowest. Assigned schools have a bold outline.
We're sorry, we currently don't have assigned school data for this listing.
Nearby Schools
6
/10
Lakemont Elementary School
901 N Lakemont Ave
Distance between this listing and this school0.84 miles
Public District Grades KG-5
5
/10
Brookshire Elementary School
2500 Cady Way
Distance between this listing and this school1.53 miles
Public District Grades PK-5
6
/10
Aloma Elementary School
2949 Scarlet Rd
Distance between this listing and this school2.03 miles
Public District Grades KG-5
Nearby Schools
5
/10
Glenridge Middle School
2900 Upper Park Rd
Distance between this listing and this school1.70 miles
Public District Grades 6-8
4
/10
Maitland Middle School
701 N Thistle Ln
Distance between this listing and this school2.27 miles
Public District Grades 6-8
8
/10
Audubon Park School
1500 Falcon Dr
Distance between this listing and this school2.43 miles
Public District Grades PK-8
Nearby Schools
6
/10
Winter Park High School
2100 Summerfield Rd
Distance between this listing and this school1.69 miles
Public Magnet Grades 9-12
1
/10
Aloma High Charter
495 N Semoran Blvd
Distance between this listing and this school2.19 miles
Public Charter Grades 9-12
4
/10
Edgewater High School
3100 Edgewater Dr
Distance between this listing and this school3.29 miles
The neighbors living near this home have an average income of $175,980. Residents of Winter Park, FL typically earn $200k+ each year. The most common type of family is married, no kids. Typical level of education for residents in this area is post secondary degree.
All data provided by Home Junction and Claritas
Frequently Asked Questions About 421 Lakewood Dr
What is the listing price of this property?
The listing price of 421 Lakewood Dr property is $4,500,000.
What type of property is this?
The property 421 Lakewood Dr is a house located in Winter Park, Florida, 32789.
Is this property for sale now?
Sale Pending: 421 Lakewood Dr is Sale Pending (Pending), which means that the seller has accepted an offer but the sale is not finalized.
What is the annual property tax for this property?
According to the records, the last property tax for 2020 is $23,031 (source: MLS/based on county public records data).
When was this property sold last time and for how much?
The last sale was on June 5, 1997 for $1,105,000. (source: MLS/tax record).
How many bedrooms and bathrooms does this property have?
The property at 421 Lakewood Dr has 5 bedrooms and 7 full and 2 half bathrooms.
What is the square footage of this property?
The property 421 Lakewood Dr is 5,847 SqFt (source: MLS/tax record).
Which year was this property built?
The year of construction for 421 Lakewood Dr is 1957.
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This home is located at 421 Lakewood Dr in Winter Park, FL and zip code 32789. This 5,847 square foot home, which was built in 1957, sits on a 0.72 acre lot. Features: 5 bedrooms, 9 bathrooms. It has been listed on Rocket Homes since October 31, 2023 and is currently priced at $4,500,000.
While more than 9 listings in Winter Park, FL in December 2024 were sold above asking price, there were more than 19 listings sold at asking price, and more than 75 were sold below. In December 2024 in Winter Park, FL there were 1.3% less homes for sale than in November 2024. The median list price of listings available in December 2024 was $475,908, while the average time on the real estate market was 66 days.
From Rocket Homes Real Estate and based on county public records data.
Listings courtesy of Stellar MLS as distributed by MLS GRID.
Copyright 2025 My Florida Regional Multiple Listing Service DBA Stellar MLS. The real estate listing data marked with this icon comes from the IDX program of the Stellar MLS system. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided exclusively for consumers’ personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Properties displayed may be listed or sold by various participants in the MLS.
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