$2,250,000
2068 Roberts Point Drive
Windermere, FL 34786
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
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**
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history46 days on market
- Status: ActiveApr 16, 2026
- Listed$2,350,000Apr 16, 2026
- Price reduced$2,250,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 46
- Subdivision
- Waterford Pointe Ph 02 Rep
- County
- Orange
- Year built
- 1999
- Living area
- 4,876 sq ft
- Price/sq ft
- $461
- Building area
- 8,410 sq ft (Estimated)
- Lot size
- 45,184 sq ft
- Lot category
- 1 to less than 2
- Flood zone
- X (12095C0215H)
- Garage
- 4 spaces
- Pool
- Private pool
- Annual taxes
- $12,356 (2025)
- Parcel #
- 01-23-27-9110-00-560
- Zoning
- R-CE
- MLS #
- O6397543
Interior Details
- Bedrooms
- 5
- Full bathrooms
- 4
- Flooring
- Brick, Carpet, Ceramic Tile, Wood
- 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
- 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)
- Laundry
- Electric Dryer Hookup, Laundry Room
- Stories / Levels
- Two
- Direction faces
- East
- Fireplace
- Yes
- In-law suite
- Yes
Heating & Cooling
- Heating
- Electric, Heat Pump, Zoned
- Cooling
- Central Air, Zoned
Parking
- Garage spaces
- 4
- Attached garage
- Yes
- Parking features
- Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Parking Pad
HOA & Financial
- HOA fee
- $325 / Monthly
- Monthly HOA
- $325/mo
- Total monthly fees
- $325/mo
- Total annual fees
- $3,900
- HOA name
- Don Asher
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- The Buyer is to verify with the HOA and the Town of Windermere.
- Approval process
- The Buyer is to verify with the HOA and the Town of Windermere.
Exterior & Construction
- Exterior features
- Balcony, Courtyard, Fire Pit, French Doors, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Rain Gutters, Sidewalk
- Construction materials
- Block, Stone, Stucco
- Roof
- Tile
- Foundation
- Slab
- Pool
- Private pool
- Water access
- Yes
- Road surface
- Asphalt, Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- Cable Available, Electricity Connected, Phone Available, Propane, Sprinkler Well, Underground Utilities, Water Connected
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Foyer | First | 7.5x9.5 |
| Living Room | First | 14.1x27.5 |
| Dining Room | First | 12.5x15 |
| Kitchen | First | 16x21 |
| Dinette | First | 9x10 |
| Family Room | First | 13x20.5 |
| Primary Bedroom | First | 24x26 |
| Primary Bathroom | First | 14x21 |
| Bedroom 2 | First | 12x20 |
| Bathroom 2 | First | 5x8 |
| Office | Second | 12x14 |
| Bonus Room | Second | 16x28 |
| Gym | Second | 7.5x24.5 |
| Balcony/Porch/Lanai | First | 25x40 |
| Balcony/Porch/Lanai | First | 35x47 |
Listing Details
- Listing date
- 2026-04-16
- On market date
- 2026-04-16
- Original list price
- $2,350,000
- Occupant type
- Vacant
- MLS area
- 34786 - Windermere
- Listing AOR
- Orlando Regional
- Status changed
- 2026-04-16
- Tax legal description
- WATERFORD POINTE PH 2 REPLAT 34/125 LOT56
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
More homes like this
$1,725,000
720 Lake Brim Dr
Winter Garden, FL 34787
4 bd · 4 ba · 3,781 sqft
Oakland Park
MLS# O6387519
$1,600,000
10370 Trout Rd
Orlando, FL 32836
4 bd · 3 ba · 3,145 sqft
Cypress Isle
MLS# O6404645
$1,499,999
241 N Dillard St
Winter Garden, FL 34787
4 bd · 3 ba · 3,507 sqft
J L Dillard Sub 3
MLS# O6353975
$1,880,000
7654 Blue Quail Ln
Orlando, FL 32835
6 bd · 5 ba · 4,969 sqft
Havencrest Ph 2
MLS# O6389765
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of June 1, 2026 at 10:07 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA