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**
For sale
Price cut: $100K (6/1)
$2,250,000
2068 Roberts Point Dr, Windermere, FL 34786
5beds
4,876sqft
Single Family Residence
Built in 1999
1.04 Acres Lot
$2,107,800 Zestimate®
$461/sqft
$325/mo HOA
What's special
Detached guest casitaOversized islandDramatic courtyard poolTennis courtsNewly painted exterior courtyardWaterfront clubhouseCovered summer kitchen
- 77 days |
- 800 |
- 49 |
Zillow last checked:
Listing updated:
Listed by:
David Dorman 407-948-8295,
CENTURY 21 CARIOTI 407-573-2121
Source: Stellar MLS,MLS#: O6397543
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 4
Rooms
- Room types: Bonus Room, Den/Library/Office, Family Room, Dining Room, Living Room, Utility Room, Storage Rooms
Primary bedroom
- Features: Ceiling Fan(s), En Suite Bathroom, Other, Walk-In Closet(s)
- Level: First
- Area: 624 Square Feet
- Dimensions: 24x26
Bedroom 2
- Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
- Level: First
- Area: 240 Square Feet
- Dimensions: 12x20
Primary bathroom
- Features: Bath With Whirlpool, Dual Sinks, Garden Bath, Makeup/Vanity Space, Other, Split Vanities, Stone Counters, Tub with Separate Shower Stall, Water Closet/Priv Toilet, Window/Skylight in Bath, Linen Closet
- Level: First
- Area: 294 Square Feet
- Dimensions: 14x21
Bathroom 2
- Features: Jack & Jill Bathroom, Shower No Tub, Single Vanity, Linen Closet
- Level: First
- Area: 40 Square Feet
- Dimensions: 5x8
Balcony porch lanai
- Features: Ceiling Fan(s)
- Level: First
- Area: 1645 Square Feet
- Dimensions: 35x47
Balcony porch lanai
- Level: First
- Area: 1000 Square Feet
- Dimensions: 25x40
Bonus room
- Features: Other, Storage Closet
- Level: Second
- Area: 448 Square Feet
- Dimensions: 16x28
Dinette
- Features: Other
- Level: First
- Area: 90 Square Feet
- Dimensions: 9x10
Dining room
- Features: Other
- Level: First
- Area: 187.5 Square Feet
- Dimensions: 12.5x15
Family room
- Features: Built-In Shelving, Ceiling Fan(s), Other, Storage Closet
- Level: First
- Area: 266.5 Square Feet
- Dimensions: 13x20.5
Foyer
- Features: Other
- Level: First
- Area: 71.25 Square Feet
- Dimensions: 7.5x9.5
Gym
- Features: Ceiling Fan(s), Other
- Level: Second
- Area: 183.75 Square Feet
- Dimensions: 7.5x24.5
Kitchen
- Features: Breakfast Bar, Kitchen Island, Other, Pantry, Stone Counters, Built-in Closet
- Level: First
- Area: 336 Square Feet
- Dimensions: 16x21
Living room
- Features: Built-In Shelving, Other
- Level: First
- Area: 387.75 Square Feet
- Dimensions: 14.1x27.5
Office
- Features: Built-In Shelving, Ceiling Fan(s), Other, Built-in Closet
- Level: Second
- Area: 168 Square Feet
- Dimensions: 12x14
Heating
- Electric, Heat Pump, Zoned
Cooling
- Central Air, Zoned
Appliances
- Included: Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator, Water Filtration System, Whole House R.O. System, Wine Refrigerator
- Laundry: Electric Dryer Hookup, Laundry Room
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), In-Law Floorplan
- Flooring: Brick/Stone, Carpet, Ceramic Tile, Hardwood
- Doors: French Doors, Outdoor Grill, Outdoor Kitchen
- Windows: Blinds
- Has fireplace: Yes
- Fireplace features: Electric, Family Room, Non Wood Burning
Interior area
- Total structure area: 8,410
- Total interior livable area: 4,876 sqft
Video & virtual tour
Property
Parking
- Total spaces: 4
- Parking features: Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Parking Pad
- Attached garage spaces: 4
- Has uncovered spaces: Yes
- Details: Garage Dimensions: 21X44
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered, Enclosed, Patio, Screened, Side Porch
- Exterior features: Balcony, Courtyard, Fire Pit, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Rain Gutters, Sidewalk
- Has private pool: Yes
- Pool features: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access, Salt Water, Screen Enclosure, Self Cleaning
- Has spa: Yes
- Spa features: Heated, In Ground
- Fencing: Other
- Has view: Yes
- View description: Trees/Woods
- Waterfront features: Lake, Waterfront, Lake Privileges, Boat Ramp - Private, Skiing Allowed
- Body of water: LAKE ROBERTS
Lot
- Size: 1.04 Acres
- Dimensions: 150 x 307
- Features: Level, Near Golf Course, Oversized Lot, Sidewalk
- Residential vegetation: Mature Landscaping, Oak Trees, Trees/Landscaped
Details
- Additional structures: Cabana, Other
- Parcel number: 012327911000560
- Zoning: R-CE
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Courtyard,Custom,Florida,Other,Traditional
- Property subtype: Single Family Residence
Materials
- Block, Stone, Stucco
- Foundation: Slab
- Roof: Tile
Condition
- Completed
- New construction: No
- Year built: 1999
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Available, Electricity Connected, Phone Available, Propane, Sprinkler Well, Street Lights, Underground Utilities, Water Connected
Green energy
- Energy efficient items: Thermostat
- Water conservation: Low-Flow Fixtures, Whole House Water Purification
Community & HOA
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)
- Security: Gated Community, Security Gate, Smoke Detector(s)
- Pet fee: $0 monthly
- Subdivision: WATERFORD POINTE PH 02 REP
HOA
- Has HOA: Yes
- Amenities included: Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(s), Vehicle Restrictions
- Services included: 24-Hour Guard, Private Road, Recreational Facilities
- HOA fee: $325 monthly
- HOA name: Don Asher
- HOA phone: 407-425-4561
Location
- Region: Windermere
Financial & listing details
- Price per square foot: $461/sqft
- Tax assessed value: $1,134,065
- Annual tax amount: $12,356
- Date on market: 4/16/2026
- Cumulative days on market: 78 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved, Asphalt
Estimated market value
$2,107,800
$2.00M - $2.21M
$6,975/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/1/2026 | Price change | $2,250,000-4.3%$461/sqft |
Source:  Stellar MLS #O6397543 Report a problem | ||
| 4/16/2026 | Listed for sale | $2,350,000+39.1%$482/sqft |
Source: Stellar MLS #O6397543 Report a problem | ||
| 8/8/2022 | Listing removed | -- |
Source: Stellar MLS #O6038267 Report a problem | ||
| 8/5/2022 | Price change | $1,690,000-6.1%$347/sqft |
Source: Stellar MLS #O6038267 Report a problem | ||
| 7/7/2022 | Listed for sale | $1,800,000+140%$369/sqft |
Source: Stellar MLS #O6038267 Report a problem | ||
| 8/24/2017 | Sold | $750,000-6.2%$154/sqft |
Source: Public Record Report a problem | ||
| 8/14/2017 | Pending sale | $799,500$164/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 8/11/2017 | Listed for sale | $799,500$164/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 7/31/2017 | Pending sale | $799,500$164/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 7/20/2017 | Price change | $799,500-5.8%$164/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 6/20/2017 | Price change | $849,000+1.2%$174/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 6/8/2017 | Pending sale | $838,800$172/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 6/6/2017 | Listed for sale | $838,800$172/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 6/2/2017 | Pending sale | $838,800$172/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 4/28/2017 | Price change | $838,800-5.6%$172/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 3/18/2017 | Price change | $888,888-6.2%$182/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 3/7/2017 | Price change | $948,000-4%$194/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 2/9/2017 | Listed for sale | $988,000+962.4%$203/sqft |
Source: BHHS FLORIDA REALTY #O5489731 Report a problem | ||
| 9/3/1998 | Sold | $93,000$19/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $11,922 +7.2% | $755,567 +3% |
| 2023 | $11,117 +3% | $733,560 +3% |
| 2022 | $10,797 +1.3% | $712,194 +3% |
| 2021 | $10,662 +0.7% | $691,450 +1.4% |
| 2020 | $10,591 +0.9% | $681,903 +2.3% |
| 2019 | $10,501 +0.7% | $666,572 +1.9% |
| 2018 | $10,428 | $654,143 -17.8% |
| 2017 | $10,428 -1.7% | $795,818 +2.3% |
| 2016 | $10,612 +0.2% | $777,736 -0.7% |
| 2015 | $10,588 -2.7% | $783,244 +13.8% |
| 2014 | $10,882 +2.1% | $688,410 +5.2% |
| 2013 | $10,656 +1.1% | $654,173 -1.4% |
| 2012 | $10,543 +2.7% | $663,513 -10.5% |
| 2011 | $10,264 +4.9% | $741,396 -6% |
| 2010 | $9,786 | $789,007 -7.3% |
| 2009 | -- | $851,097 -17.2% |
| 2008 | $8,994 +1.3% | $1,027,525 -5.9% |
| 2007 | $8,877 -6.1% | $1,091,573 +29.5% |
| 2006 | $9,454 +0% | $843,133 +35% |
| 2005 | $9,453 +4.4% | $624,507 -14.3% |
| 2004 | $9,057 +0.1% | $728,345 -1% |
| 2003 | $9,047 +2.5% | $735,515 +45.9% |
| 2002 | $8,823 -1.2% | $504,221 +4.5% |
| 2001 | $8,933 +0.7% | $482,528 +1.5% |
| 2000 | $8,872 | $475,235 |
Find assessor info on the county website
Monthly payment
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Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 34786
Nearby schools
GreatSchools rating
- 10/10Lake Whitney Elementary SchoolGrades: PK-5Distance: 1.4 mi
- 8/10SunRidge Middle SchoolGrades: 6-8Distance: 2.2 mi
- 7/10West Orange High SchoolGrades: 9-12Distance: 2 mi
Schools provided by the listing agent
- Elementary: Lake Whitney Elem
- Middle: SunRidge Middle
- High: West Orange High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Orange County
- Windermere
- 34786
- 2068 Roberts Point Dr
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