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$1,800,000

4 hours ago

2059 Woodlawn Drive, Orlando, FL

House

4 Bed

5 Bath

3646 sqft

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MLS® O6375744

  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 3646 sqft
Garage Yes
Taxes $13,256
Days Active 0
Lot Size 0.38 acres
Approx. Age 2003
Avg. Price Per Sqft $493
MLS® Number O6375744

Property Address: 2059 Woodlawn Drive, ORLANDO, FL, 32803

Average square foot calculated using Size range provided by listing agent.

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.
MLS® NumberO6375744
Laundry LevelElectric Dryer Hookup, Laundry Room, Washer Hookup
Central VacNo
FireplaceNo
Acreage0.38
Exterior
GarageYes
Approx. Age2003
Basement
DrivewayDriveway, Garage Door Opener, Garage Faces Side
Garage Spaces2
Heat
A/C
Heating Fuel

Extras

Rooms

Den:Second Floor11 × 24 ft
Living Room:First Floor20 × 16 ft
Other:Second Floor17 × 14 ft
Bedroom 2:Second Floor19 × 17 ft
Bedroom 3:Second Floor13 × 13 ft
Bedroom 4:First Floor11 × 16 ft
Other:Second Floor17 × 15 ft
Kitchen:First Floor11 × 15 ft

Similar Listings

Price History

-End Date
Not Sold YetSold Price

For Sale

Feb 4, 2026List Date
$1,800,000List Price

Home Appraisal

This property is estimated to sell between: $1,800,000 and $3,371,000.
Similar properties in this area sold on average for: $2,847,142
Expected to sell in 44 days. Similar properties sold in 44 days. This home has been on eXp Realty for 0 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

  • Commute

Commute

Starting Address
Destination Address
2059 Woodlawn Drive, ORLANDO, FL

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