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421 Lakewood Drive

Winter Park, FL 32789
  • $4,500,000
  • STATUS: Active
  • ON SITE: 599 Days
  • MLS #: O6153641
UPDATED: 25 min ago
$4,500,000
  • 5
    BEDS
  • 0.72
    ACRES
  • 7
    BATHS
  • 2
    1/2 BATHS
  • 5,847
    SQFT
  • $770
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1957
County:
Area:

School Information

Elementary School:
Middle School:
High School:

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

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© 2025 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. 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 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. Data last updated 2025-06-22T16:49:28.163.
www.endlesssummerrealty.com/homes/144880056
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421 Lakewood Drive Winter Park, FL 32789

  • Price: $4,500,000
  • Status: Active
  • On Site: 599 Days
  • Updated: 25 min ago
  • MLS #: O6153641
5
Beds
7
Baths
2
½ Baths
0.72
Acres
5,847
SQFT
$770
$/SQFT
1957
Built
Neighborhood:
Osceola Shores Sec 03
County:
Orange
Area:
Winter Park
Elementary School:
Lakemont Elem
Middle School:
Maitland Middle
High School:
Winter Park High
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
Exterior Features

Additional Water Information Winter Park Chain of Lakes Architectural Style Traditional Attached Garage Yn Yes Carport Yn No Construction Materials BlockWood Frame Covered Spaces 3 Direction Faces Southwest Exterior Features BalconyFrench DoorsIrrigation SystemLightingPrivate MailboxRain GuttersShade Shutter(s) Fencing Fenced Foundation Details BlockCrawlspaceSlab Garage Dimensions 38x22 Lot Features City LotIrregular LotOversized Lot Open Parking YN Yes Parking Features Bath In GarageCircular DrivewayGarage Door OpenerGround LevelOn StreetOversizedSplit GarageWorkshop in Garage Patio And Porch Features CoveredEnclosedFront PorchPatioPorchRear Porch Pool Features GuniteIn GroundLighting Pool Private Yn Yes Road Frontage Type Street Paved Road Surface Type PavedAsphalt Roof Shingle Spa Features In Ground Spa YN Yes View Water Water Access Lake - Chain of Lakes Water Access Yn Yes Water Body Name LAKE OSCEOLA Water Extras Lift - CoveredSkiing Allowed Water Extras Yn Yes Water View Lake - Chain of Lakes Water View Yn Yes Waterfront Features Lake - Chain of Lakes Waterfront Feet Total 110 Waterfront Yn Yes

Interior Features

Additional Rooms AtticBonus RoomBreakfast Room SeparateDen/Library/OfficeFamily RoomFlorida RoomFormal Dining Room SeparateFormal Living Room SeparateInside UtilityStorage Rooms Appliances Bar FridgeBuilt-In OvenDishwasherDisposalDryerElectric Water HeaterFreezerMicrowaveRangeRange HoodRefrigeratorTankless Water HeaterWasher Building Area Total 8083 Cooling Central Air Cooling YN Yes Fireplace Features GasWood Burning Fireplace Yn Yes Flooring CarpetHardwood Furnished Negotiable Heating CentralElectric Heating YN Yes Interior Features Built-in FeaturesCeiling Fan(s)Crown MoldingEating Space In KitchenPrimary Bedroom Main FloorSolid Surface CountersSolid Wood CabinetsSplit BedroomThermostatWalk-In Closet(s)Window Treatments Laundry Features InsideLaundry Room Levels Two Sewer Public Sewer Stories Total 2 Water Source Public Window Features BlindsDouble Pane WindowsDrapesRodsShuttersWindow Treatments

Property Features

Association Yn No Cdd Yn No Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Minimum Lease No Minimum New Construction Yn No Ownership Fee Simple Property Condition Completed Property Sub Type Single Family Residence Realtor Info No SignSurvey Available Security Features Security SystemSecurity System OwnedSmoke Detector(s) Senior Community Yn No Special Listing Conditions None Tax Annual Amount 24480.74 Total Annual Fees 0 Total Monthly Fees 0 Utilities Cable ConnectedElectricity ConnectedNatural Gas ConnectedPublicSewer ConnectedSprinkler WellWater Connected Zoning R-1AAA


Listing information © 2025 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of PREMIER SOTHEBY'S INTL. REALTY: 407-644-3295.



© 2025 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. 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 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. Data last updated 2025-06-22T16:49:28.163.
 
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