Home in 2068 Roberts Point Dr Windermere for sale with MLS# O6397543
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**
2068 Roberts Point Dr, Windermere, FL 34786
- Price:
- $2,250,000.00
- Previous Asking Price:
- $2,350,000.00
- Original List Price:
- $2,350,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $461.44
- Listing Type:
- For Sale
- Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6397543
- Bedrooms:
- 5
- Bathrooms Total:
- 4
- Full Bath:
- 4
- Additional Rooms:
- Den/library/office, Inside Utility, Bonus Room, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Storage Rooms, Interior In-law Suite W/private Entry
- Living Area:
- 4,876 Sqft
- Built-Up Area:
- 8,410 Sqft
- Lot Area:
- 45,184 Sqft
- Lot Size Dimensions and Info:
- 150x307
- Building Area Source:
- Estimated
- Living Area Source:
- Public Records
- Lot Features:
- Oversized Lot, Paved, Level, Sidewalk, Private, Near Golf Course
- Lot Size Acres:
- 1.04
- View from the Property:
- Trees/woods
- Waterfront:
- No
- Private Pool
- Swimming Pool Features:
- Gunite, Heated, Other, In Ground, Salt Water, Screen Enclosure, Outside Bath Access, Child Safety Fence, Lighting, Self Cleaning
- Spa
- Spa Features:
- Heated, In Ground
- Security:
- Smoke Detector(s), Security Gate, Gated Community
- Furnished:
- Unfurnished
- Appliances:
- Dishwasher, Disposal, Microwave, Refrigerator, Cooktop, Other, Built-in Oven, Electric Water Heater, Range Hood, Convection Oven, Wine Refrigerator, Water Filtration System
- Interior:
- Eat-in Kitchen, High Ceilings, Walk-In Closet(s), Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Kitchen/family Room Combo, Open Floorplan, Split Bedroom, Stone Counters, Thermostat, Crown Molding, Tray Ceiling(s), Dry Bar, Chair Rail, Primary Bedroom Main Floor
- Exterior:
- Balcony, Lighting, Outdoor Grill, Courtyard, Private Mailbox, Sidewalk, Rain Gutters, French Doors, Outdoor Kitchen, Fire Pit, Private Entrance
- Patio and Porch:
- Patio, Screened, Covered, Enclosed, Side Porch
- Windows:
- Blinds, Shades, Shutters
- Other Structures:
- Other, Cabana
- Laundry:
- Laundry Room, Electric Dryer Hookup
- Fireplace
- Fireplace:
- Family Room, Electric, Non Wood Burning
- Green Energy Efficient:
- Thermostat
- Air Conditioning System:
- Zoned, Central Air
- Heating System:
- Electric, Zoned, Heat Pump
- Fence:
- Other
- Vegetation and Trees:
- Trees/landscaped, Mature Landscaping, Oak Trees
- Property Entrance Faces:
- East
- Road Responsibility:
- Private Maintained Road
- Other Equipment:
- Generator, Irrigation Equipment, Fuel Tank(s), Private Entrance, Fire Pit
- Water Access
- Water Access Features:
- Lake
- Water Extras
- Water Extra Details:
- Boat Ramp - Private, Skiing Allowed
- Year Built:
- 1999
- Roof:
- Tile
- Builder Name:
- CUSTOM
- Architectural Style:
- Other, Florida, Contemporary, Traditional, Custom, Courtyard
- Levels:
- Two
- Construction Materials:
- Block, Stucco, Stone
- Flooring:
- Carpet, Wood, Ceramic Tile, Brick
- Number of stories:
- 2
- Foundation Details:
- Slab
- Flood Zone Code:
- X
- Property Condition:
- Completed
- Homestead Property
- Tax Annual Amount:
- $12,356.34
- Tax Year:
- 2025
- Association Fee:
- $325.00
- Association Fee Frequency:
- Monthly
- Total Annual Fees:
- $3,900.00
- Total Monthly Fees:
- $325.00
- Garage
- Garage Spaces:
- 4
- Attached Garage
- Parking Features:
- Driveway, Garage Door Opener, Circular Driveway, Guest, Parking Pad, Golf Cart Parking, Boat, Garage Faces Side
- Garage Dimensions:
- 21X44
- Sewer:
- Septic Tank
- Utilities Available:
- Cable Available, Underground Utilities, Phone Available, Electricity Connected, Water Connected, Sprinkler Well, Propane
- Water Source:
- Public
- Association
- Minimum Lease Term:
- 8-12 Months
- Pets Allowed?
- Amenities Provided by the Homeowner's Association (HOA):
- Clubhouse, Recreation facilities, Playground, Security, Recreation Facilities, Tennis Court(s), Gated, Park, Fence Restrictions, Vehicle Restrictions
- Subdivision Name:
- WATERFORD POINTE PH 02 REP
- Community Features:
- Clubhouse, Sidewalks, Street Lights, Park, Tennis Court(s), Playground, Deed Restrictions, Golf Carts Ok, No Truck/rv/motorcycle Parking, Gated Community - Guard
- Association Fee Includes:
- Recreational Facilities, Guard - 24 Hour, Private Road
- Senior Community:
- No
- Association Fee Required:
- Required
- Association Management:
- Don Asher
- Association Phone:
- 407-425-4561
- Listing Terms Considered by Seller:
- Cash, Conventional
- Occupant Type:
- Vacant
- Lease Considered:
- Yes
- Tax Legal Description:
- WATERFORD POINTE PH 2 REPLAT 34/125 LOT56
- Real Estate Folio Number (Parcel Number):
- 01-23-27-9110-00-560
- Zoning:
- R-CE
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Lake Whitney Elem
- High School:
- West Orange High
- Middle Or Junior School:
- Sunridge Middle
- Originally published on:
- April 16, 2026 8:10 pm
- Active on the market since:
- April 16, 2026
- Listing Agreement executed on:
- April 16, 2026
- Price change occurred on:
- June 1, 2026 2:06 pm
- Listing Status Last Changed On:
- April 16, 2026 8:10 pm
- Photos updated on:
- July 15, 2026 8:51 pm
- Last Modified:
- August 3, 2026 5:33 pm
- Association Approval Required
- Courtesy of:
- CENTURY 21 CARIOTI
- Attribution:
- 407-573-2121
- Road Surface Type:
- Paved, Asphalt
- Street Name:
- ROBERTS POINT
- Street Number:
- 2068
- City:
- WINDERMERE
- State:
- Florida
- Zip Code:
- 34786
- County:
- Orange
- Latitude:
- N28° 30' 59.8''
- Longitude:
- W82° 25' 25.2''
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Want to schedule an in-person or virtual tour? Have questions?
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Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates
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