2068 Roberts Point Drive, Windermere, FL 34786
$2,150,000 - For Sale
Property Details
Price: $2,150,000
Sq Ft: 4,876
($441 per sqft)
Bedrooms: 5
Bathrooms: 4
City:Windermere
County:Orange
Type:Single Family
Development:Waterford Pointe Ph 02 Rep
Subdivision:Waterford Pointe Ph 02 Rep
Acres:1.0400
Virtual Tour/Floorplan:View
Year Built:1999
Listing Number:O6397543
Status Code:Active Under Contract
Taxes:$12,356.34
Tax Year: 2025
Garage: 4
/ Y
Furnishings: Unfurnished
Pets Allowed: Yes
Total Recurring Fees: $325
Total Recurring Fee Frequency: 0.00
Calculate Your Payment
Equipment:
Built-In Oven
Convection Oven
Cooktop
Dishwasher
Disposal
Electric Water Heater
Microwave
Other
Range Hood
Refrigerator
Water Filtration System
Wine Refrigerator
Interior Features:
Built-in Features
Cathedral Ceiling(s)
Ceiling Fans(s)
Chair Rail
Crown Molding
Dry Bar
Eat-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)
Exterior Features:
Balcony
Courtyard
Fire Pit
Lighting
Outdoor Grill
Outdoor Kitchen
Private Entrance
Private Mailbox
Rain Gutters
Sidewalk
View:
Trees/Woods
Amenities:
Clubhouse
Fence Restrictions
Gated
Park
Playground
Recreation Facilities
Security
Tennis Court(s)
Vehicle Restrictions
Financial Information:
Taxes: $12,356.34
Tax Year: 2025
Association Fee: $325.00
Association Fee Frequency: Monthly
Room Dimensions:
Laundry: Electric Dryer Hookup, Laundry Room
School Information:
Elementary School: Lake Whitney Elem
Middle School: Sunridge Middle
Junior High: Sunridge Middle
High School: West Orange High
Save Property
View Virtual Tour
Under contract-accepting backup offers. 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**
Building Description: Contemporary, Courtyard, Custom, Florida, Other, Traditional
MLS Area: 34786 - Windermere
Total Square Footage: 8,410
Price per Square Feet: $440.94
Total Floors: 2
Water: Public
Construction: Block, Stone, Stucco
Date Listed: 2026-04-16 00:00:00
Pool: Y
Pool Description: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access, Salt Water, Screen Enclosure, Self Cleaning
Private Spa: Y
Furnished: Unfurnished
Windows: Blinds, Shades, Shutters
Parking: Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Parking Pad
Garage Description: Y
Garage Spaces: 4
Attached Garage: Y
Flooring: Brick, Carpet, Ceramic Tile, Wood
Roof: Tile
Heating: Electric, Heat Pump, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Gated Community, Security Gate, Smoke Detector(S)
Laundry: Electric Dryer Hookup, Laundry Room
Pets: Yes
Sewer: Septic Tank
Lot Desc.: Level, Near Golf Course, Oversized Lot, Sidewalk, Paved, Private
Parcel ID: 01-23-27-9110-0
Amenities: Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(S), Vehicle Restrictions
Listing Courtesy Of: Century 21 Carioti
david@daviddorman.com
Under contract-accepting backup offers. 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**
Share Property
Additional Information:
Building Description: Contemporary, Courtyard, Custom, Florida, Other, Traditional
MLS Area: 34786 - Windermere
Total Square Footage: 8,410
Price per Square Feet: $440.94
Total Floors: 2
Water: Public
Construction: Block, Stone, Stucco
Date Listed: 2026-04-16 00:00:00
Pool: Y
Pool Description: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access, Salt Water, Screen Enclosure, Self Cleaning
Private Spa: Y
Furnished: Unfurnished
Windows: Blinds, Shades, Shutters
Parking: Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Parking Pad
Garage Description: Y
Garage Spaces: 4
Attached Garage: Y
Flooring: Brick, Carpet, Ceramic Tile, Wood
Roof: Tile
Heating: Electric, Heat Pump, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Gated Community, Security Gate, Smoke Detector(S)
Laundry: Electric Dryer Hookup, Laundry Room
Pets: Yes
Sewer: Septic Tank
Lot Desc.: Level, Near Golf Course, Oversized Lot, Sidewalk, Paved, Private
Parcel ID: 01-23-27-9110-0
Amenities: Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(S), Vehicle Restrictions
Map of 2068 Roberts Point Drive, Windermere, FL 34786
Listing Courtesy Of: Century 21 Carioti
david@daviddorman.com
WORK WITH US
Get assistance in determining current property value, crafting a competitive offer, writing and negotiating a contract, and much more. Get in touch today!
Location
1201 6th Ave W. Suite 300
Bradenton, FL, 34205
Contact
THE WISZ TEAM 248-514-2579
IDX information is provided exclusively for consumers’ personal, noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. The data relating to real estate for sale on this Website comes in part from the Broker Reciprocity Program (BR Program) of My Florida Regional MLS DBA Stellar MLS. The source of this real property information is the copyrighted and proprietary database compilation of the My Florida Regional MLS DBA Stellar MLS and © 2026. Information last refreshed: 2026-10-27 11:04:04
Our Web site Accessibility
We are committed to providing an accessible web site. If you have difficulty accessing content, have difficulty viewing a file on the web site, or notice any accessibility problems, please contact us to specify the nature of the accessibility issue and any assistive technology you use. We will strive to provide the content you need in the format you require.
We welcome your suggestions and comments about improving ongoing efforts to increase the accessibility of this web site.