USAFLWinter ParkCypress Reserve2820 Bear Island Pointe

2820 Bear Island Pointe, Winter Park, FL

House

Pending

Listed price in listed location currency (USD).

$2,095,000

352

MLS® O6395836

Key Facts
Description
Rooms
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 5138 sqft

Garage Yes

Taxes $13,815

Lot Size

Approx. Age 1998

Avg. Price Per Sqft $407

MLS® Number O6395836

Property Address: 2820 Bear Island Pointe, Winter Park, FL, 32792-9426

Average square foot calculated using Size range provided by listing agent.

Description

Under contract-accepting backup offers. Tucked behind the gates of Cypress Reserve, this stunning custom-built lakefront home sits on 110 feet of private waterfront along the serene shores of Bear Gully Lake. Inspired by a featured Southern Living plan and thoughtfully expanded, the home blends timeless architecture with generous, well-appointed living spaces — all framed by panoramic water views, rolling greens, and towering oaks and cypress trees that define the lakefront lifestyle at its finest. Inside, the main level offers a gracious and versatile floor plan with formal living and dining rooms, a family room anchored by an electric fireplace, and a dedicated office or flex space. The spacious kitchen features custom cabinetry, generous prep space, and an adjoining dinette — with plenty of room to add an island — while a large laundry room with extensive cabinetry and a utility sink, plus a half bath, ensure exceptional everyday functionality. The first-floor primary suite is a true sanctuary, offering breathtaking lake views, a spa-inspired en suite with a jetted tub, walk-in shower, a very desirable his and her split bath with abundant counter space and storage, and an oversized walk-in closet complete with built-in shelving and dresser drawers. Upstairs, two oversized bedrooms each enjoy their own private en suite with tub/shower combination, ample closet space, and comfortable proportions. The enormous bonus room above the garage fills with natural light through dormer windows and offers endless possibilities. A walk-in attic provides exceptional storage rarely found in homes of any size. Step out to the covered back porch and take in sweeping panoramic views of Bear Gully Lake — a breathtaking backdrop that shifts beautifully with the light throughout the day - this is Florida lakefront living at its absolute finest. Meander down to your private dock for a morning kayak or a sunset boat ride, then rinse off at the east-facing porch complete with a sink and outdoor shower before heading back inside. The rolling greens, ancient oaks, and towering cypress trees frame the property in natural splendor, and an additional storage room with its own entrance and hurricane shutters ensures everything you need for lake life is right at hand. Set in the gated community of Cypress Reserve with easy access to top private schools including The Geneva School and Trinity Prep, and with convenient proximity to SR-417 for effortless travel to Orlando International Airport and beyond, this is a rare opportunity to own a one-of-a-kind lakefront estate in one of Winter Park's most coveted settings.

MLS® NumberO6395836

Laundry LevelEnsuite

Central VacNo

FireplaceNo

Acreage

Exterior

GarageYes

Approx. Age1998

Basement

Driveway

Garage Spaces

Heat

A/C

Heating Fuel

Extras

Price History

-End Date

-Sold Price

Pending

Apr 4, 2026List Date

$2,095,000List Price

Commute

Commute

Starting Address

Destination Address

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