2068 Roberts Point Drive, WINDERMERE, FL

$2,250,000

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5

Beds

4

Baths

4,876

Square feet

1.04

Acres

About 2068 Roberts Point Drive

Virtually Staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita and Lake Access. A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the property combines architectural presence, exceptional privacy, and resort-inspired living in a peaceful enclave known for estate-sized homes, mature landscaping, and private access to Lake Roberts. Designed around a dramatic courtyard pool, the home creates a true indoor-outdoor lifestyle experience, ideal for both grand entertaining and everyday living. The detached guest casita is a standout feature, offering exceptional flexibility for guests, private office use, wellness retreat, creative studio, or evolving lifestyle needs. Inside, soaring ceilings, polished marble tile flooring, detailed crown molding, and dramatic two-story living spaces create a sense of scale and elegance throughout. The thoughtfully updated chef’s kitchen is designed for gathering, featuring quartz countertops, an oversized island, premium KitchenAid and Bosch appliances, double ovens, wine refrigeration, and seamless connection to the expansive family room with custom built-ins and fireplace. The private first-floor primary suite serves as a true retreat, offering direct courtyard and pool access, a spacious custom walk-in closet, and a beautifully appointed bath with dual vanities, jetted soaking tub, and walk-in shower. A second first-floor suite provides ideal accommodations for guests or family. Upstairs, expansive, flexible living spaces include a large game room overlooking the courtyard, a dedicated office with custom built-ins, a private fitness room with balcony access, and additional secondary bedrooms thoughtfully arranged for privacy and functionality. Outdoor living is equally compelling, with a screened resort-style saltwater pool and heated spa with waterfall, covered summer kitchen, multiple entertaining spaces, and the privacy that only a homesite of this scale can provide. Waterford Pointe residents enjoy an exceptional lifestyle with private access to Lake Roberts, a waterfront clubhouse, tennis courts, playground, and beautifully tree-lined streets—all within one of Windermere’s most desirable gated communities. Additional highlights include a 4-car garage, a new whole-house generator, three HVAC systems, a newly painted exterior courtyard, and highly regarded local schools. For buyers seeking privacy, architectural character, flexible living, and established Windermere luxury—without the premium of direct lakefront pricing—this is a compelling opportunity. **Private tours available by appointment**

Features of 2068 Roberts Point Drive

MLS® # O6397543
Price $2,250,000
Bedrooms 5
Bathrooms 4.00
Full Baths 4
Square Footage 4,876
Acres 1.04
Year Built 1999
Type Residential
Sub-Type Single Family Residence
Style Courtyard, Custom, Florida, Other, Traditional
Status Active

Community Information

Address 2068 Roberts Point Drive
Area Windermere
Subdivision WATERFORD POINTE PH 02 REP
City WINDERMERE
County Orange
State FL
Zip Code 34786-5807
Housing for Seniors No

Amenities

Amenities Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(s), Vehicle Restrictions
Parking Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Parking Pad
# of Garages 4
View Trees/Woods
Is Waterfront No
Waterfront Lake, Waterfront
Has Pool Yes

Interior

Interior Features Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Chair Rail, Crown Molding, Dry Bar, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s)
Appliances Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator, Water Filtration System, Whole House R.O. System, Wine Refrigerator
Heating Electric, Heat Pump, Zoned
Cooling Central Air, Zoned
Fireplace Yes
Fireplaces Electric, Family Room, Non Wood Burning
# of Stories 2

Exterior

Exterior Features Balcony, Courtyard, Fire Pit, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Rain Gutters, Sidewalk
Lot Description Level, Near Golf Course, Oversized Lot, Sidewalk
Roof Tile
Foundation Slab

School Information

Elementary Lake Whitney Elem
Middle SunRidge Middle
High West Orange High

Additional Information

Date Listed April 16th, 2026
Days on Market 92
Zoning R-CE
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

AgentDavid Dorman
OfficeCENTURY 21 CARIOTI

Listing Map

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