FL
Orange
ORLANDO
32803
2059 WOODLAWN DRIVE
2059 WOODLAWN DRIVE, ORLANDO, FL 32803
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Listing Type
Single Family
Listing Status
Pending
67
$1,800,000

Home Details for 2059 WOODLAWN DRIVE

Price
$1,800,000
Type
Residential
Bedrooms
4
Bathrooms
5.0
Square feet
3646
Year built
2003
Lot size acres
0.38
County
Orange
Total rooms
8
Garage
2
Days on site
23
MLS Listing#
O6375744
Property Description

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
  • House Interior
    • Coffered Ceiling(s)
    • Crown Molding
    • Eat-in Kitchen
    • Open Floorplan
    • Walk-In Closet(s)
  • Utilities
    • Cable Available
    • Cable Connected
    • Electricity Connected
    • Water Connected
  • Parking
    • Driveway
    • Garage Door Opener
    • Garage Faces Side
    • Attached
  • Heating Information
    • Central
    • Electric
    • Heat Pump
  • Cooling Information
    • Central Air
    • Zoned
  • Water Features
    • Public
    • See Remarks
  • Fire Place
    • Living Room
    • Wood Burning
  • Garage
    • 1
School Information
School Information for 2059 WOODLAWN DRIVE, ORLANDO, FL 32803
Elementary School
Audubon Park K8
Middle School
Audubon Park K-8
High School
Winter Park High
Listing Courtesy: BALDWIN PARK REALTY LLC - 407-986-9800
Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the 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. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright ©2026 MLS GRID. All Rights Reserved.
Last Updated: 2026-02-10 19:40:21
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EXIT KING REALTY
1800 S. Tamiami Trail, Venice, FL 34293
Chet Hockett
License #: 3552572
Sales Representative
Office
941 497 6060
Agent
941 599 1042
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