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. 9×12) 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 35×47 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!
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. 9×12) 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 35×47 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!
Property Details
Price:
$2,350,000
MLS #:
O6397543
Status:
Active
Beds:
5
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WATERFORD POINTE PH 02 REP
Neighborhood:
34786windermere
Listed Date:
Apr 16, 2026
Finished Sq Ft:
4,876
Total Sq Ft:
8,410
Lot Size:
45,184 sqft / 1.04 acres (approx)
Year Built:
1999
See this Listing
Schools
Elementary School:
Lake Whitney Elem
Middle School:
SunRidge Middle
High School:
West Orange High
Interior
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
Bathrooms
4 Full Bathrooms
Cooling
Central Air, Zoned
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
Levels
Two
Exterior
Architectural Style
Courtyard, Custom, Florida, Other, Traditional
Association Amenities
Clubhouse, Fence Restrictions, Gated, Park, Playground, Recreation Facilities, Security, Tennis Court(s), Vehicle Restrictions
Attached Garage YN
1
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)
Construction Materials
Block, Stone, Stucco
Covered Spaces
4
Direction Faces
East
Exterior Features
Balcony, Courtyard, Fire Pit, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Rain Gutters, Sidewalk
Fencing
Other
Garage Spaces
4
Green Energy Efficient
Thermostat
Lot Features
Level, Near Golf Course, Oversized Lot, Sidewalk
Open Parking YN
1
Other Structures
Cabana, Other
Parking Features
Boat, Circular Driveway, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Guest, Parking Pad
Patio And Porch Features
Covered, Enclosed, Patio, Screened, Side Porch
Roof
Tile
Security Features
Gated Community, Security Gate, Smoke Detector(s)
Spa Features
Heated, In Ground
View
Trees/Woods
Waterfront Features
Lake, Waterfront
Window Features
Blinds, Shades, Shutters
Financial
HOA Fee
$325
HOA Fee Frequency
Monthly
HOA Includes
24-Hour Guard, Private Road, Recreational Facilities
HOA Name
Don Asher
HOA Phone
407-425-4561
Tax Year
2025
Taxes
$12,356
Map
Community
- Address2068 ROBERTS POINT DRIVE WINDERMERE FL
- SubdivisionWATERFORD POINTE PH 02 REP
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE AND UNREC
- ALADAR ON LAKE BUTLER
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BELLA VITA ESTATES
- BELLARIA
- BELMERE VILLAGE
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G3 48 70
- BELMERE VILLAGE G4 50 58
- BUTLER BAY
- BUTLER RIDGE
- CARRINGTON
- CASA DEL LAGO REP
- CASABELLA
- CASABELLA PH 2
- CHAINE DU LAC
- DAVIS SHORES
- DOWN ACRES ESTATES
- DOWN POINT SUB
- DOWN POINT SUBDIVISION
- DOWNS COVE CAMP SITES
- EDEN ISLE
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTATES AT LAKE CLARICE
- ESTATES AT WINDERMERE
- FARMS
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- ISLEWORTH
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 01
- KEENES POINTE UNIT 03 46/104
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 2
- KEENES POINTE UNIT 7
- KEENES POINTE UT 04 SEC 31 48 82
- KELSO ON LAKE BUTLER
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #35 36
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CRESENT RESERVE
- LAKE CYPRESS COVE PH 02
- LAKE DOWN COVE
- LAKE DOWN ESTATES
- LAKE DOWN SHORES REP
- LAKE HANCOCK SHORES
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 02
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 04
- LAKE SAWYER SOUTH PH 05
- LAKE SAWYER SOUTH PH 3
- LAKE SAWYER SOUTH PHASE 4
- LAKES
- LAKES OF WINDERMERE LAKE REAMS TOWNHOMES
- LAKES OF WINDERMERE PH 02A
- LAKES OF WINDERMERE PH 2A
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE PH 3
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE AT LAKES OF WINDERMERE
- LAKESIDE AT LAKES OF WINDERMRE CONDOMINIUM
- LAKESIDE VILLAGE TWNHMS
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE CONDO
- LAKESIDE/LKS/WINDERMERE PH 10
- LAKESIDE/LKS/WINDERMERE PH 3
- LAKESIDE/LKS/WINDERMERE PH 4
- LANDINGS AT LAKE SAWYER
- LEGADO
- MARINA BAY ESTATES
- METCALF PARK REP
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE
- OASIS COVE II/LAKESIDE VILLAGE PH
- OXFORD MOOR 47/30
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- PROVIDENCE PH 2
- RESERVE AT BELMERE 48 23
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PH 03 51 01
- RESERVE AT LAKE BUTLER
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND 45/120
- RESERVE AT LAKE BUTLER SOUND UNIT 02
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- RESERVE/BELMERE PH 04
- ROBERTS LANDING
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SILVER WOODS
- SILVER WOODS PH 01
- SILVER WOODS PH 02
- SILVER WOODS PH 03
- SILVER WOODS PH 03A
- SILVER WOODS PH 04
- SILVER WOODS PH 3
- SOUTHBRIDGE VILLAGE
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT HORIZON WEST
- SUMMERPORT PH 02
- SUMMERPORT PH 04 C E F & G
- SUMMERPORT TRAIL
- SUMMERPORT TRL
- SUNSET BAY
- TENNYSON PK/SUMMERPORT
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TILDENS GROVE PH 1
- TUSCANY RIDGE 50 141
- VINEYARDS OF HORIZONS WEST
- VINEYARDS/HORIZONS WEST PH 1B
- VINEYARDS/HORIZONS WEST PH 2B
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSIDE
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WEST LAKE BUTLER ESTATES
- WEST POINT COMMONS
- WESTOVER CLUB PH 02 47/71
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES / BELMERE PH 02
- WHITNEY ISLES AT BELMERE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WILLOWS AT LAKE RHEA PH 01
- WINDERMERE
- WINDERMERE CLUB/BUTLER BAY
- WINDERMERE DOWNS
- WINDERMERE DOWNS 1ST ADD
- WINDERMERE DOWNS PH 03
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE LNDGS FD-1
- WINDERMERE LNDGS PH 02
- WINDERMERE RESERVE
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PH 3B
- WINDERMERE TRAILS PHASE 1B
- WINDERMERE TRAILS PHASE 1C 80/15 LOT 113
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH IA
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Apr 24, 2026
289
Single Family Listed
96
Avg DOM
460
Avg $ / SqFt
$2,239,515
Avg List Price
Property Summary
- Located in the WATERFORD POINTE PH 02 REP subdivision, 2068 ROBERTS POINT DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $2,350,000 and features 5 beds, 4 baths, and has approximately 4,876 square feet of living space, and was originally constructed in 1999. The current price per square foot is $482. The average price per square foot for Single Family listings in WINDERMERE is $460. The average listing price for Single Family in WINDERMERE is $2,239,515. To schedule a showing of MLS#o6397543 at 2068 ROBERTS POINT DRIVE in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of CENTURY 21 CARIOTI. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 2068 ROBERTS POINT DRIVE
WINDERMERE, FL
