2068 ROBERTS POINT DRIVE, Windermere, FL, 34786 | $2,250,000

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**

Features

  • Amenities: Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(s), Vehicle Restrictions
  • Rooms: 15
  • Bedrooms: 5
  • Baths: 4 full
  • Lot Size: 150 x 307
  • Laundry: Electric Dryer Hookup, Laundry Room
  • Style: Courtyard, Custom, Florida, Other, Traditional
  • Year Built: 1999
  • Garage: 4-car Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Parking Pad
  • Heating: Electric, Heat Pump, Zoned
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 4,876
  • Acreage: 1.04
  • Lot Size: 150 x 307
  • Est. Taxes: $12,356
  • HOA Fee: $325 Monthly
  • Lot Desc: Level, Near Golf Course, Oversized Lot, Sidewalk
  • View: Trees/Woods
  • Elem. School: Lake Whitney Elem
  • Middle School: SunRidge Middle
  • High School: West Orange High
  • Pool: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access, Salt Water, Screen Enclosure, Self Cleaning
  • Pet Policy: Yes
  • 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
  • MLS#: O6397543
  • Days on Market: 46 days
  • Website: https://www.raveis.com
    /eprop/O6397543/2068robertspointdrive_windermere_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. (last updated 6/29/2026 2:32:38 PM)

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NMLS Mortgage Loan Originator ID 1020051

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2068 ROBERTS POINT DRIVE, Windermere, FL, 34786

$2,250,000

Joseph Sciuto

Luxury Properties Specialist

William Raveis Real Estate

Phone: 508.457.8622

Joseph.Sciuto@raveis.com

Frank Merola

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 508.740.5922

Frank.Merola@raveis.com

NMLS Mortgage Loan Originator ID 1020051

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $1,800,000 $1,800,000 $1,800,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.750% 6.000% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.251% 6.086% 6.183%
Monthly Tax Payment $1,030 $1,030 $1,030
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $10,504 $10,792 $15,189
Total Monthly Payment $11,659 $11,947 $16,344

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.