2068 ROBERTS POINT DRIVE, Windermere, FL, 34786 | $2,350,000

One or more photo(s) has been virtually staged. 1+ Acre Estate in Guard-Gated Windermere with Private Courtyard Pool, Detached Casita & Whole-Home Generator. Rare opportunity in Waterford Pointe offering space, privacy, and Lake Roberts access.

Situated in one of Windermere’s premier guard-gated communities, this 5-bedroom, 4-bath estate features a private pool, a new Generac Guardian 24kW whole-house generator, and over an acre of land, providing exceptional privacy, scale, and architectural style. Waterford Pointe is noted for estate-sized homes, mature landscaping, and a peaceful, low-density atmosphere, offering space and tranquility rarely found in newer developments.

The courtyard design centers around the pool, blending indoor and outdoor living with an estate feel.

Inside, the residence (4, 441 sq. ft. ) features soaring ceilings, a dramatic two-story living room with an elevated conversation area and dual crystal chandeliers, large polished marble tile flooring, a two-story family room, and detailed crown molding throughout. The layout balances formal and casual spaces, offering flexibility for both everyday living and entertaining.

The kitchen is thoughtfully updated for gathering, featuring quartz countertops, an oversized island, and newer black stainless steel KitchenAid and Bosch appliances. Appointments include a double oven with convection, a 48” refrigerator, wine refrigeration, and a glass cooktop, all opening to a two-story family room with an electronic fireplace, custom built-ins, and a hidden space for your AV electronics.

The first-floor primary suite includes plantation shutters, direct courtyard and pool access, and wood-look tile. The bath offers dual vanities, a jetted tub, a walk-in shower, and a custom closet (approx. 9x12) with built-ins. Three HVAC systems—including one for the primary suite—ensure comfort and efficiency.

The first floor also has a second suite, ideal for guests or family. A detached casita (435 sq. ft. ) with a private entrance and full bath is ideal as an in-law suite, guest retreat, or office, offering privacy and versatility.

Upstairs, the home offers expansive living spaces, including a large game room with a balcony overlooking the courtyard, a dedicated office featuring custom wood built-ins, and a separate fitness room with its own private balcony and a spiral staircase leading directly to the primary suite. Additional bedrooms are thoughtfully situated, with two connected by a Jack-and-Jill bathroom. Several bathrooms now showcase modern finishes and seamless glass enclosures.

Outdoor living includes a 35x47 screened pool and patio with an automatic saltwater system, a heated spa, and a waterfall. The resurfaced pool and covered outdoor kitchen with grill, side burner, and prep sink, plus an additional brick patio, offer multiple entertaining areas.

Waterford Pointe residents enjoy a lifestyle community with:
* Private boat ramp with access to Lake Roberts,
* Waterfront clubhouse with lake views,
* Tennis courts and playgrounds, and
* Tree-lined streets and estate-sized homesites.
Additional features include:
* 4-car garage,
* Two buried propane tanks,
* Rain gutters and partial fencing,
* Newer courtyard exterior paint,
* Located within a highly regarded school district.
Experience this home’s blend of space, privacy, and established luxury—plus lake access and community amenities—in one of Windermere’s most desirable gated communities. Schedule your tour today!

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: 1 day
  • 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 5/12/2026 1:53:23 AM)
Listing courtesy of CENTURY 21 CARIOTI   Phone: 407-573-2121

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2068 ROBERTS POINT DRIVE, Windermere, FL, 34786

$2,350,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $1,880,000 $1,880,000 $1,880,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.875% 6.125% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.300% 6.235% 6.164%
Monthly Tax Payment $1,030 $1,030 $1,030
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $11,121 $11,423 $15,865
Total Monthly Payment $12,276 $12,578 $17,020

* 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.