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2059 WOODLAWN DRIVE
ORLANDO FL 32803 US

$1,800,000

Active Listing ID O6375744
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4 bed
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5.00 Bath (4 Full , 1 Half)
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Lot: 0.38 Acres
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Single Family Residence

$1,800,000

Active Listing ID O6375744
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2059 WOODLAWN DRIVE Custom-built estate on a rare 1/3-acre lot overlooking Lake Sue and Beeman Park, thoughtfully designed for multi-generational spaces and split plan living. This Southern European–inspired home features multiple private living quarters connected by covered loggias, offering independence, privacy, and flexibility rarely found in a single-family residence. Wraparound double loggias surround a central courtyard with a wood-burning outdoor fireplace and lake views, creating seamless indoor-outdoor living. The lagoon-style pool and spa with wall fountain and programmable LED lighting are set within expansive, professionally landscaped grounds—perfect for relaxing or entertaining. The main living areas feature 10-foot ceilings on both levels, 8-foot solid and French doors, and a striking curved staircase. The open kitchen flows into the dining and family rooms, ideal for shared gatherings while maintaining private retreats throughout the home. Finishes include custom millwork, crown molding, plantation shutters, solid interior doors, high-end custom cabinetry, and granite countertops in the kitchen, baths, and laundry room. The four-bedroom, four-and-a-half-bath layout plus office is uniquely configured for separate, private bedroom spaces. A ground-floor bedroom connects to the main residence via a covered balcony, ideal for guests, extended family, or live-in support. The second-floor office is also accessed by a loggia and includes a private exterior stairway, offering potential for a home office, studio, or independent suite. The upstairs primary suite provides additional separation and privacy within a three-way split plan. Additional features include a two-car side-entry garage, covered parking for three vehicles, open parking for two more, gated driveways, and custom gates and railings throughout. Located in one of Orlando’s most desirable and quiet neighborhoods, with convenient access to Winter Park, Baldwin Park, Mills Park, and top-rated Winter Park schools, this one-of-a-kind property offers unmatched versatility for today’s multi-generational lifestyle.

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Property Features

  • Facts
  • Lot Size: 0.38 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • 1/2 Bathrooms: 1
  • Cooling System: Central Air, Zoned
  • Exterior Finish: Corner Lot, Awning(s), Balcony, Courtyard, French Doors, Garden, Private Mailbox, Rain Gutters, Shade Shutter(s), Pool
  • Floor Covering: Brick, Carpet, Tile, Tile - Ceramic, Wood
  • Roof Type: Tile
  • Heating Fuels: Central, Electric (Heating), Fireplace(s), Heat Pump (Heating)
  • Additional Features
  • Fireplace
  • Pool

School Information

  • School
  • Audubon Park K8(Elementary)
  • Audubon Park K-8(MiddleSchool)
  • Winter Park High(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 1800000
  • unparsedaddress: 2059 WOODLAWN DRIVE
  • postalcity: ORLANDO
  • stateorprovince: FL
  • country: US
  • postalcode: 32803
  • bathroomsfull: 4
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.38
  • lotsizeunits: Acres
  • lotsizearea: 0.38
  • livingarea: 3646
  • livingareaunits: Square Feet
  • latitude: 28.572254
  • longitude: -81.349995
  • listagentfullname: Bobby Livera
  • listagentemail: Bobby@BaldwinparkRE.com
  • listagentkey: 3yd-MFRMLSFL-261217211
  • listagentmlsid: 261217211
  • listagentpreferredphone: 3212312308
  • listagentofficephone: 4079869800
  • listofficekey: 3yd-MFRMLSFL-261016016
  • listagentstatelicense: 3294874
  • listofficemlsid: 261016016
  • disclaimer: Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: MFRMLSFL
  • yearbuilt: 2003
  • listingcontractdate: 2026-02-03
  • listagenturl: https://www.baldwinparkre.com
  • countyorparish: Orange
  • parcelnumber: 18-22-30-0568-00-400
  • elementaryschool: Audubon Park K8
  • highschool: Winter Park High
  • appliances: Cooktop, Dishwasher, Garbage Disposer, Microwave, Oven - Convection, Refrigerator, Washer
  • cooling: Central Air, Zoned
  • constructionmaterials: Block, Stucco
  • flooring: Brick, Carpet, Tile, Tile - Ceramic, Wood
  • heating: Central, Electric (Heating), Fireplace(s), Heat Pump (Heating)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Carport, Driveway, Garage, Garage - Attached
  • roof: Tile
  • waterfrontyn: False
  • interiorfeatures: Coffered Ceiling(s), Crown Molding, Eat-in Kitchen, Kitchen/Family Room Combo, Open Floorplan, Primarybedroom Upstairs, Solid Wood Cabinets, Split Bedroom, Walk-in Closet(s)
  • exteriorfeatures: Corner Lot, Awning(s), Balcony, Courtyard, French Doors, Garden, Private Mailbox, Rain Gutters, Shade Shutter(s), Pool
  • architecturalstyle: Mediterranean
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bathroom 5, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Den, Kitchen, Living Room
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.35, 28.572254
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Baldwin Park Realty, LLC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"Bobby@BaldwinparkRE.com", "ListBrokerageCity":"Orlando", "ListBrokerageCountry":"US", "ListBrokerageEmail":"brian@baldwinparkre.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"Baldwin Park Realty, LLC", "ListBrokeragePhone":"(407) 986-9800", "ListBrokeragePostalCode":"32814", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":"Ste A", "ListBrokerageUnparsedAddress":"1400 Lake Baldwin Ln", "ListBrokerageWebsiteUrl":"https://www.baldwinparkre.com", "ListOfficeAddress1":"1400 Lake Baldwin Ln #A", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":null, "ListOfficeCity":"Orlando", "ListOfficeCountry":"US", "ListOfficeEmail":"brian@baldwinparkre.com", "ListOfficePostalCode":"32814", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Mediterranean, Single Family Residence - ORLANDO, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/2059-Woodlawn-Dr_Orlando_FL_32803_M67030-99006?f=listhub&s=MFRMLSFL&m=O6375744&c=rexren", "MLSModificationTimestamp":"2026-02-05T17:25:09Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Single Family Residence", "RawPropertyType":"Residential", "RoomCount":8, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":13256, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 2/6/2026 12:05:28 AM GMT
Source Updated Date: 2/6/2026 12:43:37 PM GMT

Courtesy of: Bobby Livera, BALDWIN PARK REALTY LLC, Bobby@BaldwinparkRE.com

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.