2068 Roberts Point Dr

Windermere, FL 34786

$2,350,000
Price
5
Beds
4,876 Sq. Ft.
$482 / Sq. Ft.
4,876
Sq. Ft.
$482
per Sq. Ft.
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Description

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...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
  1. Listed by David Dorman • Brokerage DRE #2036282 • CENTURY 21 CARIOTI
    P: (407)-948-8295 C: (407)-948-8295 David@DavidDorman.com

Property Details for 2068 Roberts Point Drive

Architectural Style
Courtyard, Custom, Florida, Other, Traditional
Subdivision Name
WATERFORD POINTE PH 02 REP
Township
23
Garage Spaces
4
View
Trees/Woods
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 05/18/2026 12:58 PM

Property Details for 2068 Roberts Point Drive

StatusActive
MLS #O6397543
Days on Market38
Taxes$12,356 / year
HOA Fees$325 / month
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1999
Lot Size1.04 AC / 45,184 SF
CountyOrange County
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Location

Listing Courtesy of CENTURY 21 CARIOTI, David Dorman
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Building Information for 2068 Roberts Point Drive

Stories2Year Built1999Building Size-Lot Size1.04 AC / 45,184 SF

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$13,065 per month

30 year fixed, 6.36% Interest

Principal and Interest

$11,710

Property Taxes

$1,030

HOA Dues

$325

The Payment Calculator is for illustrative purposes only.

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Property Information for 2068 Roberts Point Drive

Summary
Location and General Information
  • Building Area Source: Estimated
  • Building Area Total: 8410.0
  • Building Area Units: Square Feet
  • 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)
  • Direction Faces: East
  • 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.
  • Elementary School: Lake Whitney Elem
  • Middle Or Junior School: SunRidge Middle
  • High School: West Orange High
  • Other Equipment: Fuel Tank(s), Generator, Irrigation Equipment
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved, Private Road
  • Senior Community: No
  • Unit Number: No
  • Street Number: 2068
  • Street Name: ROBERTS POINT
  • Street Suffix: DRIVE
  • State: FL
  • City: WINDERMERE
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage Dimensions: 21X44
  • Garage: Yes
  • Parking Features: Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Parking Pad
Taxes and HOA Information
  • Association Approval Required: Yes
  • Association Fee Includes: 24-Hour Guard, Private Road, Recreational Facilities
  • Association Fee Requirement: Required
  • Association Name: Don Asher
  • Association Phone: 407-425-4561
  • Association: Yes
  • CDD: No
  • Pet Restrictions: The Buyer is to verify with the HOA and the Town of Windermere.
  • Tax Block: 00
  • Tax Book Number: 34-125
  • Tax Legal Description: WATERFORD POINTE PH 2 REPLAT 34/125 LOT56
  • Tax Lot: 56
  • Tax Year: 2025
Property
Lot Information
  • Additional Parcels: No
  • Additional Water Information: Private boat ramp for the community.
  • Lot Features: Level, Near Golf Course, Oversized Lot, Sidewalk
  • Lot Size Dimensions: 150 x 307
  • Parcel Number: 012327911000560
  • Total Acreage: 1 to less than 2
  • Water Access: Lake
  • Water Access: Yes
  • Water Body Name: LAKE ROBERTS
  • Water Extras: Boat Ramp - Private, Skiing Allowed
  • Water Extras: Yes
  • Water: Boat Ramp - Private, Skiing Allowed
  • Zoning: R-CE
  • Living Area: 4876
  • Lot Dimensions: 150 x 307
  • ILS Total SQFT: 495.0
  • ILS Under Air SQFT: 495.0
Property and Assessments
  • Year Built Numeric: 1999
  • Association Amenities: Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(s), Vehicle Restrictions
  • Flood Zone Code: X
  • Flood Zone Date: 09-24-2021
  • Flood Zone Panel: 12095C0215H
  • Homestead: Yes
  • New Construction: No
  • Property Condition: Completed
  • Public Survey Range: 27
  • Public Survey Section: 01
  • Dock YN: No
Utilities
  • Green Energy Efficient: Thermostat
  • Green Water Conservation: Low-Flow Fixtures, Whole House Water Purification
  • Sewer: Septic Tank
  • Utilities: Cable Available, Electricity Connected, Phone Available, Propane, Sprinkler Well, Street Lights, Underground Utilities, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Builder Name: CUSTOM
  • Construction Materials: Block, Stone, Stucco
  • Exterior Features: Balcony, Courtyard, Fire Pit, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Rain Gutters, Sidewalk
  • Fencing: Other
  • Foundation Details: Slab
  • Levels: Two
  • Other Structures: Cabana, Other
  • Patio And Porch Features: Covered, Enclosed, Patio, Screened, Side Porch
  • Pool Dimensions: 15x30
  • Pool Features: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access, Salt Water, Screen Enclosure, Self Cleaning
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Tile
  • Security Features: Gated Community, Security Gate, Smoke Detector(s)
  • Spa Features: Heated, In Ground
  • Spa: Yes
  • Vegetation: Mature Landscaping, Oak Trees, Trees/Landscaped
  • Waterfront Features: Lake, Waterfront
  • Waterfront Feet Total: 0
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 4
  • 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
  • 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
  • Cooling: Central Air, Zoned
  • Fireplace Features: Electric, Family Room, Non Wood Burning
  • Fireplace: Yes
  • Flooring: Brick/Stone, Carpet, Ceramic Tile, Hardwood
  • Heating: Electric, Heat Pump, Zoned
  • Interior Features: 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)
  • Laundry Features: Electric Dryer Hookup, Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 15.0
  • Water View: No
  • Window Features: Blinds, Shades, Shutters
  • Bathrooms Half: 0
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 2068 Roberts Point Drive

DateEvent & SourcePriceAppreciation
Apr 16, 2026

Listed (Active)

MFRMLS #O6397543

$2,350,000—
Feb 1, 2023

Withdrawn

MFRMLS #O6038267

$1,690,000—
Jul 7, 2022

Listed (Active)

MFRMLS #O6038267

$1,800,000—
DateEvent & SourcePrice
04/16/2026

Listed (Active)

MFRMLS #O6397543

$2,350,000
02/01/2023

Withdrawn

MFRMLS #O6038267

$1,690,000
07/07/2022

Listed (Active)

MFRMLS #O6038267

$1,800,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 2068 Roberts Point Drive

Taxable ValueLand-Additions-Total-
Tax Record2024$11,922 ($993 / month)
Home Facts
Beds5Total Finished SqFt4,876 SqFtAbove Grade Finished SqFt4,876 SqFtStories2Lot Size45,184 SqFtStyleSingle Family ResidenceYear Built1999ZoningR-CECountyORANGEAPN01-23-27-9110-00-560

Schools near 2068 Roberts Point Drive

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Lake Whitney Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
SunRidge Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Lake Whitney Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

SunRidge Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 2068 Roberts Point Drive, Windermere, FL 34786

2068 Roberts Point Drive is a single family home for sale in Windermere, FL 34786. This property was listed for sale on April 16, 2026 by CENTURY 21 CARIOTI, it's currently listed at $2,350,000. It has been on the market for a total of 38 days and was last sold on August 25, 2017. This listing's school district is Orange County Public Schools. Nearby schools include Lake Whitney Elementary School, Cornerstone Academy Charter and SunRidge Middle School. 2068 Roberts Point Drive is a 5-bed, 4-bath, 4,876 sqft single family home built in 1999.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of CENTURY 21 CARIOTI, David Dorman

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 05/18/2026 12:58 PM