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$4,087,500
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Property Description
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...
Full Property Details
Full Property Details for 421 Lakewood Dr
General
- Sold For: $4,087,500
- Taxes: $24,480 (2023)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6153641
- Added to Site: 810 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 14
- Interior Features: Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Thermostat, Walk-In Closet(s), Window Treatments
- Fireplace: Yes
- Fireplace(s): Gas, Wood Burning
- Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Freezer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer
- Furnishings: Negotiable
- Flooring: Carpet, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 9
- Full Bathrooms: 7
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground, Lighting
- Spa: Yes
- Spa Description: In Ground
- Security/Safety: Security System, Security System Owned, Smoke Detector(s)
Exterior
- Exterior Features: Balcony, French Doors, Irrigation System, Lighting, Private Mailbox, Rain Gutters, Shade Shutter(s)
- Deck/Patio: Covered, Enclosed, Front Porch, Patio, Porch, Rear Porch
- Porch/Patio/Deck: Covered, Enclosed, Front Porch, Patio, Porch, Rear Porc
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Bath In Garage, Circular Driveway, Garage Door Opener, Ground Level, On Street, Oversized, Split Garage, Workshop in Garage
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: OSCEOLA SHORES SEC 03
- Driving Directions: Osceola Ave to Trismen Terrace to Detmar Dr to left on Lakewood Dr...
- Direction Faces: Southwest
School Information
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
Community
- Community Name: 32789 - Winter Park
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Public Sewer
- Water District: LAKE OSCEOLA
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Sprinkler Well, Water Connected
Structural Information
- Architectural Info: Traditional
- Architectural Style: Traditional
- Exterior Const.: Block, Wood Frame
- Roof: Shingle
- Windows: Blinds, Double Pane Windows, Drapes, Rods, Shutters, Window Treatments
- Stories/Levels: Two
- Square Feet: 5,847
- Sq. Ft. Source: Public Records
- Living Area: 5,847 Sq. Ft.
- Year Built: 1957
Lot Features
- Property View: Water
- Lot Size (Acres): 0.72
- Lot Size (Sq. Ft.): 31,500
- Lot Size: 31500
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Fenced
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake - Chain of Lakes
- Water Extras: Yes
- Water Front Name: LAKE OSCEOLA
- Water Front Desc.: Lake - Chain of Lakes
Financial Considerations
- Tax Amount: $24,480.74
- Tax Year: 2023
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: OSCEOLA SHORES SECTION 3 S/87 LOT 7 BLKA
- Flood Zone Info: X
- APN: 52230647601070
- Property ID: 52230647601070
- Block/Lot/Section: A
Listed by Premier Sotheby's Intl. Realty
Sold by Stockworth Realty Group
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Schools
Schools serving 421 Lakewood Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Lakemont Elementary School 901 North Lakemont Avenue, Winter Park, FL 32792 | K-5 | 0.8 mi |
Maitland Middle School 701 North Thistle Lane, Maitland, FL 32751 | 6-8 | 2.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 421 Lakewood Dr
Date
Details
Price
Change
Source
8/20/2025
Sold
$4,087,500
-9.17%
MLS
9/09/2024
Price Reduced
$4,500,000
-5.26%
MLS
5/31/2024
Price Reduced
$4,750,000
-4.9%
MLS
3/10/2024
Price Reduced
$4,995,000
-4.86%
MLS
1/15/2024
Price Reduced
$5,250,000
-4.46%
MLS
10/31/2023
Listed
$5,495,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
421 Lakewood Drive, Winter Park, FL 32789 (MLS# O6153641) is a Single Family property that was sold at $4,087,500 on August 20, 2025. Want to learn more about 421 Lakewood Drive? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

