2059 Woodlawn Drive, Orlando, FL 32803
Pending $1,800,000
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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.
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)
Taxes: $13,256.00
Tax Year: 2024
Awning(s)
Balcony
Courtyard
French Doors
Garden
Private Mailbox
Rain Gutters
Shade Shutter(s)
Built-In Oven
Convection Oven
Cooktop
Dishwasher
Disposal
Electric Water Heater
Exhaust Fan
Microwave
Refrigerator
Water
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Junior High: Audubon Park K-8
High School: Winter Park High
MLS Area: 32803 - Orlando/Colonial Town
Price per Square Feet: $493.69
Water: Public, See Remarks
Lot Desc.: Corner Lot, Sidewalk
Construction: Block, Stucco
Date Listed: 2026-02-04 13:50:40
Pool: Yes
Pool Type: Gunite, Heated, In Ground, Salt Water
Private Spa: Yes
Furnished: Unfurnished
Windows: Double Pane Windows, Insulated Windows, Window Treatments
Parking: Driveway, Garage Door Opener, Garage Faces Side
Garage Spaces: 2
Flooring: Brick, Carpet, Ceramic Tile, Wood
Roof: Tile
Heating: Central, Electric, Heat Pump
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Septic Tank
Listing Courtesy Of: Baldwin Park Realty Llc
Bobby@BaldwinparkRE.com
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.
Property Details
Price: $1,800,000
Sq Ft: 3,646
($494 per
sqft)
Bedrooms: 4
Bathrooms: 4
Partial Baths: 1
City: Orlando
County: Orange
Type: Single Family Reside
Development: Beeman Park
Acres: 0.38
Virtual Tour/Floorplan: View
Year Built: 2003
Listing Number: O6375744
Status Code: Pending
Taxes: $13,256.00
Tax Year: 2024
Garage:
2
Furnishings: Unfurnished
Pets Allowed: Yes
Interior Features:
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)
Financial Information:
Taxes: $13,256.00
Tax Year: 2024
Exterior Features:
Awning(s)
Balcony
Courtyard
French Doors
Garden
Private Mailbox
Rain Gutters
Shade Shutter(s)
Equipment:
Built-In Oven
Convection Oven
Cooktop
Dishwasher
Disposal
Electric Water Heater
Exhaust Fan
Microwave
Refrigerator
View:
Water
School Information:
Elementary School: Audubon Park K8
Middle School: Audubon Park K-8
Junior High: Audubon Park K-8
High School: Winter Park High
Additional Information:
MLS Area: 32803 - Orlando/Colonial Town
Price per Square Feet: $493.69
Water: Public, See Remarks
Lot Desc.: Corner Lot, Sidewalk
Construction: Block, Stucco
Date Listed: 2026-02-04 13:50:40
Pool: Yes
Pool Type: Gunite, Heated, In Ground, Salt Water
Private Spa: Yes
Furnished: Unfurnished
Windows: Double Pane Windows, Insulated Windows, Window Treatments
Parking: Driveway, Garage Door Opener, Garage Faces Side
Garage Spaces: 2
Flooring: Brick, Carpet, Ceramic Tile, Wood
Roof: Tile
Heating: Central, Electric, Heat Pump
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Septic Tank
Map of 2059 Woodlawn Drive, Orlando, FL 32803
Listing Courtesy Of: Baldwin Park Realty Llc
Bobby@BaldwinparkRE.com