For sale · Active

2068 Roberts Point Drive

Windermere, FL 34786 · Waterford Pointe Ph 02 Rep

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5 beds4 baths4,876 sqftbuilt 1999

About this home

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**

The essentials

Status
Active
Property type
Single Family Residence
Year built
1999
Days on market
105
Subdivision
Waterford Pointe Ph 02 Rep
County
Orange
MLS #
O6397543

Interior

Living area
4,876 sqft
Bedrooms
5
Bathrooms
4
Flooring
Brick/Stone, Carpet, Ceramic Tile, Hardwood
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)
Cooling
Central Air, Zoned
Heating
Electric, Heat Pump, Zoned

Exterior & lot

Lot size
1.037 Acres
Pool
Child Safety Fence, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access, Salt Water, Screen Enclosure, Self Cleaning
Waterfront
LAKE ROBERTS
View
Trees/Woods
Garage spaces
4
Construction
Block, Stone, Stucco
Roof
Tile
Exterior features
Balcony, Courtyard, Fire Pit, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Rain Gutters, Sidewalk

Community & costs

HOA fee
$325 Monthly
Association
Don Asher
Amenities
Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(s), Vehicle Restrictions
Annual taxes
$12,356
Ownership
Fee Simple

Listing courtesy of CENTURY 21 CARIOTI · Stellar MLS. This information is believed to be accurate, but without warranty.