Active

Overview

  • Updated On:
  • May 16, 2025
  • 5 Bedrooms
  • 8 Bathrooms
  • 5,847.00 ft2

421 LAKEWOOD DRIVE, WINTER PARK

$ 4,500,000
421 LAKEWOOD DRIVE, ,

Overview

  • Updated On:
  • May 16, 2025
  • 5 Bedrooms
  • 8 Bathrooms
  • 5,847.00 ft2

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…

Address: 421 LAKEWOOD DRIVE
State/County:
Zip: 32789
Country: US
Open In Google Maps
Property Id : 763385
Price: $ 4,500,000
Property Size: 5,847.00 ft2
Property Lot Size: 0.72 ft2
Rooms: 14
Bedrooms: 5
Bathrooms: 8
ArchitecturalStyle: Traditional
BathroomsFull: 7
BathroomsHalf: 2
BathroomsTotalDecimal: 8
BridgeModificationTimestamp: 2025-05-16T19:27:16.542Z
BuildingAreaTotal: 8083
CoListAgentFullName: John Pinel
CoListAgentMlsId: 261071963
CoListOfficeMlsId: 261014339
CoListOfficeName: PREMIER SOTHEBY'S INTL. REALTY
ConstructionMaterials: Block,Wood Frame
ContractStatusChangeDate: 2023-10-31
Cooling: Central Air
CoveredSpaces: 3
CumulativeDaysOnMarket: 287
DaysOnMarket: 287
DirectionFaces: Southwest
Directions: Osceola Ave to Trismen Terrace to Detmar Dr to left on Lakewood Dr...
ElementarySchool: Lakemont Elem
Fencing: Fenced
FireplaceFeatures: Gas,Wood Burning
Flooring: Carpet,Hardwood
FoundationDetails: Block,Crawlspace,Slab
Furnished: Negotiable
GarageSpaces: 3
Heating: Central,Electric
HighSchool: Winter Park High
IDXParticipationYN: 1
InternetAddressDisplayYN: 1
InternetAutomatedValuationDisplayYN: 1
InternetEntireListingDisplayYN: 1
LaundryFeatures: Inside,Laundry Room
LeaseConsideredYN: 1
Levels: Two
ListAOR: Orlando Regional
ListAgentAOR: Orlando Regional
ListAgentEmail: micknight1@gmail.com
ListAgentFullName: Mick Night
ListAgentKey: ed83bdcdf14a5d5065e6ad9f98f93642
ListAgentMlsId: 261010033
ListAgentPreferredPhone: 407-629-4446
ListOfficeKey: 502cac97bd1e45884eb7970447fda253
ListOfficeMlsId: 261014339
ListOfficeName: PREMIER SOTHEBY'S INTL. REALTY
ListOfficePhone: 407-644-3295
ListingContractDate: 2023-10-31
ListingId: O6153641
ListingKeyNumeric: 707171447
LivingAreaSource: Public Records
LivingAreaUnits: Square Feet
LotFeatures: City Lot,Irregular Lot,Oversized Lot
LotSizeArea: 31500
LotSizeSquareFeet: 31500
LotSizeUnits: Square Feet
MLSAreaMajor: 32789 - Winter Park
MaloneId: 2034130205
MiddleOrJuniorSchool: Maitland Middle
MlsStatus: Active
ModificationTimestamp: 2025-05-16T19:26:44.587Z
OnMarketDate: 2023-10-31
OriginalEntryTimestamp: 2023-10-31T21:51:37.300Z
OriginalListPrice: 5495000
OriginatingSystemKey: stellar
OriginatingSystemName: Stellar MLS
Ownership: Fee Simple
ParcelNumber: 052230647601070
ParkingFeatures: Bath In Garage,Circular Driveway,Garage Door Opener,Ground Level,On Street,Oversized,Split Garage,Workshop in Garage
PatioAndPorchFeatures: Covered,Enclosed,Front Porch,Patio,Porch,Rear Porch
PhotosChangeTimestamp: 2024-10-09T18:07:15.342Z
PhotosCount: 41
PoolFeatures: Gunite,In Ground,Lighting
PostalCodePlus4: 3939
PriceChangeTimestamp: 2024-09-09T20:58:18.750Z
PropertyCondition: Completed
RoadFrontageType: Street Paved
RoadSurfaceType: Paved,Asphalt
Roof: Shingle
STELLAR_AdditionalRooms: Attic,Bonus Room,Breakfast Room Separate,Den/Library/Office,Family Room,Florida Room,Formal Dining Room Separate,Formal Living Room Separate,Inside Utility,Storage Rooms
STELLAR_AdditionalWaterInformation: Winter Park Chain of Lakes
STELLAR_BOMDate: 2025-05-16T04:00:00.000Z
STELLAR_BackupsRequestedYN: 1
STELLAR_CalculatedListPriceByCalculatedSqFt: 769.63
STELLAR_ContractStatus: Inspections
STELLAR_CreateAutomaticVirtualTourYN: 1
STELLAR_CurrentPrice: 4500000
STELLAR_DPRURL: https://www.workforce-resource.com/dpr/listing/MFRMLS/O6153641?w=Agent&skip_sso=true
STELLAR_DPRURL2: https://www.workforce-resource.com/dpr/listing/MFRMLS/O6153641?w=Customer
STELLAR_DaystoContract: 376
STELLAR_ExpectedClosingDate: 2025-03-14T04:00:00.000Z
STELLAR_FloodZoneCode: X
STELLAR_GarageDimensions: 38x22
STELLAR_GreenVerificationCount: 0
STELLAR_HomesteadYN: 1
STELLAR_ListOfficeContactPreferred: 407-644-3295
STELLAR_ListOfficeHeadOfficeKeyNumeric: 537903989
STELLAR_ListSource: MATRIX
STELLAR_ListSourceOriginal: MATRIX
STELLAR_MinimumLease: No Minimum
STELLAR_MlsMajorChangeType: Back On Market
STELLAR_OfficeIDXOfficeParticipationYN: 1
STELLAR_OfficeSyndicateTo: Apartments.com,International MLS,Realtor.com,Zillow Rental,SkySlope Offers
STELLAR_PreviousStatus: Pending
STELLAR_PublicRemarksRequired: Under contract-accepting backup offers.
STELLAR_PublicRemarksSpanishReq: Bajo contrato-aceptando ofertas de respaldo.
STELLAR_RATIO_CurrentPrice_By_CalculatedSqFt: 769.63
STELLAR_RealtorInfo: No Sign,Survey Available
STELLAR_ShowingRequirements: Appointment Only
STELLAR_ThirdPartyYN: 1
STELLAR_TotalAcreage: 1/2 to less than 1
STELLAR_TotalAnnualFees: 0
STELLAR_TotalMonthlyFees: 0
STELLAR_WaterAccess: Lake - Chain of Lakes
STELLAR_WaterAccessYN: 1
STELLAR_WaterExtras: Lift - Covered,Skiing Allowed
STELLAR_WaterExtrasYN: 1
STELLAR_WaterView: Lake - Chain of Lakes
STELLAR_WaterViewYN: 1
STELLAR_WaterfrontFeetTotal: 110
STELLAR_ZoningCompatibleYN: 1
SecurityFeatures: Security System,Security System Owned,Smoke Detector(s)
Sewer: Public Sewer
SourceSystemKey: 707171447
SpaFeatures: In Ground
SpecialListingConditions: None
StateOrProvince: FL
StatusChangeTimestamp: 2025-05-16T19:24:22.613Z
StoriesTotal: 2
StreetName: LAKEWOOD
StreetNumber: 421
StreetNumberNumeric: 421
StreetSuffix: DRIVE
TaxAnnualAmount: 24480.74
TaxBlock: A
TaxBookNumber: S-87
TaxLegalDescription: OSCEOLA SHORES SECTION 3 S/87 LOT 7 BLKA
TaxLot: 7
TaxYear: 2023
Utilities: Cable Connected,Electricity Connected,Natural Gas Connected,Public,Sewer Connected,Sprinkler Well,Water Connected
View: Water
WaterBodyName: LAKE OSCEOLA
WaterSource: Public
WaterfrontFeatures: Lake - Chain of Lakes
WindowFeatures: Blinds,Double Pane Windows,Drapes,Rods,Shutters,Window Treatments
YearBuilt: 1957
Zoning: R-1AAA
FeedTypes: IDX
Other Features
Balcony
Bar Fridge
Built-in Features
Built-In Oven
Ceiling Fan(s)
Crown Molding
Dishwasher
Disposal
Dryer
Eating Space In Kitchen
Electric Water Heater
Freezer
French Doors
Garage Attached
Has a View
Has Cooling System
Has Fireplace
Has Garage
Has Heating System
Has Pool
Has Waterfront
Irrigation System
Lighting
Microwave
Open Parking
Primary Bedroom Main Floor
Private Mailbox
Rain Gutters
Range
Range Hood
Refrigerator
Shade Shutter(s)
Solid Surface Counters
Solid Wood Cabinets
Spa
Split Bedroom
Tankless Water Heater
Thermostat
Walk-In Closet(s)
Washer
Window Treatments
Mon 09 Jun
Tue 10 Jun
Wed 11 Jun
Thu 12 Jun
Fri 13 Jun
Sat 14 Jun
Sun 15 Jun
Mon 16 Jun
Tue 17 Jun
Wed 18 Jun
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