2068 ROBERTS POINT DRIVE Windermere, FL $ 2,250,000
2068 ROBERTS POINT DRIVE
$ 2,250,000
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2068 ROBERTS POINT DRIVE

Windermere, FL, 34786
$ 2,250,000
Bedrooms5 Baths4.0 Sq 4,876

Monthly Estimate*

$ 13,854

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View a Virtual Tour

Single Family Home for sale in Windermere, FL

for $2,250,000 with 5 bedrooms and 4 full baths. This 4,876 square foot home was built in 1999 on a lot size of 1.04.

One or more photo(s) has been 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**

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Single Family Active

Price

$ 2,250,000

Bedrooms

5

Full Bath

4

Property Type

Single Family

Taxes

$ 12,356

Style

Courtyard Custom Florida Other Traditional

Lot Size

1.04

Year Built

1999

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6397543

Features
General
Sewer Septic Tank
Heating Electric Heat Pump Zoned
Cooling Central Air Zoned
Utilities Cable Available Electricity Connected Phone Available Propane Sprinkler Well Street Lights Underground Utilities Water Connected
Roof Tile
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
Zoning R-CE
HOA Fee 325
Garage Spaces 4
Association Fee Includes 24-Hour Guard Private Road Recreational Facilities
Patio/Porch Features Covered Enclosed Patio Screened Side Porch
Architectural Style Courtyard Custom Florida Other Traditional
Pool Features Child Safety Fence Gunite Heated In Ground Lighting Other Outside Bath Access Salt Water Screen Enclosure Self Cleaning
Security Features Gated Community Security Gate Smoke Detector(s)
Construction Materials Block Stone Stucco
Pets Allowed Yes
Year Built 1999
View Trees/Woods
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Waterfront Features Lake Waterfront
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)
Assoc Fee Paid Per Monthly
County Orange
New Construction false
Property Type Residential
Association Amenities Clubhouse Fence Restrictions Gated Park Playground Recreation Facilities Security Tennis Court(s) Vehicle Restrictions
Attached Garage true
Energy Efficient Thermostat
Subdivision Name WATERFORD POINTE PH 02 REP
Facing Direction East
Garage Y/N true
Green Water Conservation Low-Flow Fixtures Whole House Water Purification
Other Structures Cabana Other
Total Rooms 15
Full Baths 4
Status Active
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.
High School West Orange High
City WINDERMERE
Body of Water LAKE ROBERTS
Association Name Don Asher
Senior Community Y/N false
MLS Area 34786 - Windermere
Lot Size Units Acres
Lot Size Square Feet 45184
Carport Y/N false
Listing Terms Cash Conventional
Spa Features Heated In Ground
Elementary School Lake Whitney Elem
Land Lease Y/N false
Tax Annual Amount 12356.34
Middle/Junior High School SunRidge Middle
Property Condition Completed
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://storybookviewer.com/119157-141763 https://view.paradym.com/idx/2068-Roberts-Point-Dr-Windermere-FL-347876/4964797
Building Area Units Square Feet
Living Area Units Square Feet
Builder Name CUSTOM
Standard Status Active
Occupancy Type Vacant
Tax Lot 56
Legal Description WATERFORD POINTE PH 2 REPLAT 34/125 LOT56
Water Access Type Lake
Minimum Lease 8-12 Months
Water Access Y/N true
Monthly HOA Amount 325
Additional Rooms Bonus Room Den/Library/Office Family Room Formal Dining Room Separate Formal Living Room Separate Inside Utility Interior In-Law Suite w/Private Entry Storage Rooms
ILS Total SQFT 495
ILS Under Air SQFT 495
Water View Y/N false
Flood Zone Code X
DockY/N false
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Interior
Interior Amenities 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)
Flooring Brick/Stone Carpet Ceramic Tile Hardwood
Furnished Y/N Unfurnished
Fireplace Features Electric Family Room Non Wood Burning
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds Shades Shutters
Fireplace Y/N true
Half Baths 0
Laundry Features Electric Dryer Hookup Laundry Room
Total Bedrooms 5
Total Baths 4
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Exterior
Exterior Amenities Balcony Courtyard Fire Pit French Doors Irrigation System Lighting Outdoor Grill Outdoor Kitchen Private Entrance Private Mailbox Rain Gutters Sidewalk
Vegetation Mature Landscaping Oak Trees Trees/Landscaped
Fencing Other
Parking Features Boat Circular Driveway Driveway Garage Door Opener Garage Faces Side Golf Cart Parking Guest Parking Pad
Lot Features Level Near Golf Course Oversized Lot Sidewalk
Water Source Public
Lot Size Area 1.0373
Foundation Details Slab
Spa true
Building Area Total 8410
Lot Dimensions 150 x 307
Lot Size Acres 1.04
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 4
Road Frontage Type Street Paved Private Road
Road Responsibility Private Maintained Road
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* Excluded Features
List By
Century 21 Carioti

Broker

David@DavidDorman.com

Email

Affordability Calculator

$14,883
Per Month
93%
7%
0%
Monthly Principal & Interest
$13,854
Monthly Property Taxes
$1,030
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
6/1/2026$2,250,000 -4.26% Price Down
4/16/2026$2,350,000 Listed Price

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2068 ROBERTS POINT DRIVE, Windermere, FL, 34786 is a Single Family Home for sale at $2,250,000 with 4,876 sqft and a lot size of 1.04. 2068 ROBERTS POINT DRIVE has 5 bedrooms, 4.0 baths, and was built in 1999. The property's zip code is 34786 which is in Windermere, FL