This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/83
$2,250,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/83
Property Description
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**
Full Property Details
Full Property Details for 2068 Roberts Point Dr
General
- Price: $2,250,000
- HOA FEE: $325/month
- Taxes: $12,356 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6397543
- Updated: 7/30/2026
- Added to Site: 106 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 15
- Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Chair Rail, Crown Molding, Dry Bar, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Electric, Family Room, Non Wood Burning
- 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
- Furnishings: Unfurnished
- Flooring: Brick/Stone, Carpet, Ceramic Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 4
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Electric Dryer Hookup, Laundry Room
Additional Information
- Shared Amenities: Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(s), Vehicle Restrictions
- Pool: Yes
- Private Pool: Yes
- Pool Description: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access, Salt Water, Screen Enclosure, Self Cleaning
- Spa: Yes
- Spa Description: Heated, In Ground
- Security/Safety: Gated Community, Security Gate, Smoke Detector(s)
Exterior
- Exterior Features: Balcony, Courtyard, Fire Pit, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Rain Gutters, Sidewalk
- Deck/Patio: Covered, Enclosed, Patio, Screened, Side Porch
- Porch/Patio/Deck: Covered, Enclosed, Patio, Screened, Side Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 4
- Covered Spaces: 4
- Parking Features: Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Parking Pad
Location
- Area: 34786 - Windermere
- County: Orange
- Development Name: 34786 - Windermere
- Subdivision: WATERFORD POINTE PH 02 REP
- Driving Directions: From Main Street Windermere, Turn Left onto Windermere Road, the turn Left onto McKinnon Road. Follow down and turn Right onto Water Point Blvd. Turn Left onto Roberts Point Dr and follow down to the house on the Left.
- Direction Faces: East
School Information
- Elementary School: Lake Whitney Elem
- Middle School: SunRidge Middle
- High School: West Orange High
Community
- Community Name: 34786 - Windermere
- Community Features: Community Boat Ramp, Dock, Fishing, Lake, Water Access, Waterfront, Clubhouse, Deed Restrictions, Gated Community - Guard, Golf Carts OK, No Truck/RV/Motorcycle Parking, Park, Playground, Sidewalks, Tennis Court(s)
- Optional Amenities: Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(s), Ve
- Association: Yes
- Assoc. Name: Don Asher
- Assoc. Fees Include: 24-Hour Guard, Private Road, Recreational Facilities
- Pet Restrictions: The Buyer is to verify with the HOA and the Town of Windermere.
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Electric, Heat Pump, Zoned
Utilities
- Sewer: Septic Tank
- Water District: LAKE ROBERTS
- Water: Public
- Utility Description: Cable TV Available, Electricity Connected, Phone Available, Propane, Sprinkler Well, Street Lights, Underground Utilities, Water Connected
Structural Information
- Architectural Info: Courtyard, Custom, Florida, Other, Traditional
- Architectural Style: Courtyard, Custom, Florida, Other, Traditional
- Builder: CUSTOM
- Exterior Const.: Block, Stone, Stucco
- Roof: Tile
- Windows: Blinds, Shades, Shutters
- Stories/Levels: Two
- Square Feet: 4,876
- Sq. Ft. Source: Public Records
- Year Built: 1999
Additional Structures
- Other Structures: Cabana, Other
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 1.04
- Lot Size (Sq. Ft.): 45,184
- Lot Size: 1.0373
- Lot Dimensions: 150 x 307
- Frontage: Street Paved, Private Road
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Other
Water Features
- Water Access: Yes
- Water Access Desc: Lake
- Water Extras: Yes
- Water Front Name: LAKE ROBERTS
- Water Front Desc.: Lake, Waterfront
Green Features
- Energy Efficient: Thermostat
- Water Conservation: Low-Flow Fixtures, Whole House Water Purification
Financial Considerations
- Association Fee: $325
- Assoc Fee Freq.: Monthly
- Assoc Fee Desc.: Required
- Tax Amount: $12,356.34
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WATERFORD POINTE PH 2 REPLAT 34/125 LOT56
- Flood Zone Info: X
- APN: 12327911000560
- Property ID: 12327911000560
Listed by Century 21 Carioti
Get Pre-Approved Today
Schools
Schools serving 2068 Roberts Point Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Lake Whitney Elementary School 1351 Windermere Road, Winter Garden, FL 34787 | K-5 | 1.3 mi |
SunRidge Middle School 14955 Sunridge Boulevard, Winter Garden, FL 34787 | 6-8 | 2.2 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 1.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 2068 Roberts Point Dr
Date
Details
Price
Change
Source
6/01/2026
Price Reduced
$2,250,000
-4.26%
MLS
4/16/2026
Listed
$2,350,000
213.33%
MLS
8/25/2017
Sold
$750,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 2068 Roberts Point Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$12,356
4%
$798,470
6%
2024
$11,922
7%
$755,567
3%
2023
$11,117
4%
$733,560
6%
2021
$10,662
-1%
$691,450
-3%
2022
$10,797
1%
$712,194
4%
2021
$10,662
2%
$681,903
2%
2019
$10,501
1%
$666,572
2%
2018
$10,428
-2%
$654,143
-1%
2017
$10,612
—
$658,773
2%
2016
$10,588
-2%
$645,223
1%
2015
$10,771
-1%
$640,738
1%
2014
$10,882
2%
$635,653
2%
2013
$10,656
—
$626,259
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 2068 Roberts Point Dr
2068 Roberts Point Drive, Windermere, FL 34786 (MLS# O6397543) is a Single Family property with 5 bedrooms and 4 full bathrooms. 2068 Roberts Point Drive is currently listed for $2,250,000 and was received on April 16, 2026. Want to learn more about 2068 Roberts Point Drive? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

