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$2,250,000 - 2068 Roberts Point Drive, WINDERMERE

5
Bedrooms
4
Baths
4,876
SQ. Feet
1.04
Acres

One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita, Lake Access & an Exceptional Seller Incentive: Up to $36,000 Toward a Rate Buy-Down or Buyer Closing Costs. 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**

Essential Information

  • 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

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
  • 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

  • Days on Market:
    106
  • Zoning:
    R-CE

Listing Details

  • Listing Office:
    Century 21 Carioti

Listing information courtesy of Century 21 Carioti.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on August 2nd, 2026 at 3:37am EDT.