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2068 ROBERTS POINT DRIVE, WINDERMERE, FL - photo 1

$2,150,000

2068 ROBERTS POINT DRIVE

WINDERMERE, FL 34786

Estimated payment $11,772/month

includes HOA $325/mo · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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5Beds
4Baths
4,876Sq Ft
$441Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

HOA $325/mo
Private Pool
Fireplace
Garage
Built in 1999
45,184 sqft Lot

About This Home

Under contract-accepting backup offers. 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**

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:5
  • •Bathrooms:4
  • •Full bathrooms:4
  • •Half bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:4,876 sqft
  • •Total interior livable area:4,876 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:45,184 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1999

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Price history

DateEventPrice
2026-04-16T00:00:00.000ZListed for sale$2,150,000$441/sqft

Listing Agent

David Dorman

CENTURY 21 CARIOTI

Brokerage Phone: 407-573-2121

Source: Stellar MLS · MLS #O6397543

Data Powered by Home Junction, Inc.

Nearby

Schools

LAKE WHITNEY ELEMENTARY

Elementary · 1.3 mi

WEST ORANGE HIGH

High · 1.7 mi

ESTEEM ACADEMY

High · 1.8 mi

Dining

Dunkin'

0.2 mi

Jeremiah's Italian Ice At Westside Shoppes

0.3 mi

Champions Grille at Windermere Country Club

0.8 mi

Parks

George Bailey Park

1.4 mi

Warrior Park

1.8 mi

West Orange Park

1.9 mi

Beaches

Conrad Beach

8.1 mi

West Beach

8.1 mi

East Beach

8.2 mi

Nearby amenity locations include data © OpenStreetMap contributors.