Get new listings emailed daily! JOIN SIGN IN
Lisa Varano
REALTOR®
(941) 730-9060
Facebook Icon LinkedIn Icon Pinterest Icon Twitter Icon 
$2,095,000

2820 Bear Island Pointe Winter Park, FL 32792 Residential - Single Family Active

  • 2820 Bear Island Pointe, Winter Park, FL 32792 Main Photo

75 Total Photos [Click to View All]

Description

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.

Property Highlights

Property Type: Residential - Single Family
Cooling: Central Air
Garage: 2 car attached
Heating: Central, Electric
Lot Size: 0.80 Acres
Roof Type: Shingle
Stories: 2.0
Taxes: $13,815
Year Built: 1998

General Information

Bedrooms: 3
Bathrooms: 4 Full 1 Half
Sqft: 5,138
County: Seminole
High School: Lake Howell High
Subdivision: CYPRESS RESERVE
Listed By:
Kelly Price KELLY PRICE & COMPANY LLC 407-645-4321

Amenities

Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
Split Bedroom
Walk-In Closet(s)
Private Mailbox

Room Information

Living Room: 25x18
Dining Room: 16x15
Kitchen: 15x10
Dinette: 15x10
Primary Bedroom: 15x31
Primary Bathroom: 18x8
Family Room: 21x18
Bedroom 2: 15x19
Bedroom 3: 22x20
Bonus Room: 27x28
Office: 16x14

Property Features

Additional Rooms: Den/Library/Office, Formal Dining Room Separate, Great Room, Inside Utility, Storage Rooms
Appliances: Dryer, Washer
Association Amenities: Gated
Body of Water: BEAR GULLY LAKE
Community Features: Deed Restrictions, Gated Community - No Guard
Days on Site: 4
Directions: Howell Branch Rd to Bear Gully Rd. Turn left on Cypress Reserve Place. Then left on Bear Island Pointe. Home is on left hand side.
Exterior: Frame
Fireplace: Family Room, Living Room
Fireplace Y/N: Yes
Flood Zone Code: X
Flooring: Tile, Wood
Foundation: Slab
Frontage Lake: 102
Garage Dimensions: 24x23
HOA Fee: 1900/ Annually
HOA Y/N: Yes
Home Warranty Y/N: No
Lot Dimensions: 0.8
Ownership: Fee Simple
Patio/Porch: Rear Porch
Pets Allowed: Yes
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, No Lockbox, ShowingTime
Special Sale Provisions: None
Special View Info: Water
Utilities: BB/HS Internet Available, Cable Available
Vegetation: Trees/Landscaped
Water: Public
Water Access: Lake
Water Access Y/N: Yes
Waterfront Features: Lake Front, Seawall - Concrete, Skiing Allowed
Water View: Lake
Windows: Blinds
Zoning: R-1AA
$2,095,000
3beds
4.5baths
5,138sqft
2cars
New to the Market Active
BEDS3 BATHS4 full 1 partial SQUARE FEET5,138 MLS#O6395836
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONCYPRESS RESERVE

Get in Touch

Contact an agent to learn more about

2820 Bear Island Pointe, Winter Park, FL 32792.

Contact Form

Preferred Communication Method:

Estimate Your Payment

Estimated Payment

$ 8,828.38 per month $7,066.08 Principal & Interest $1,151.25 Property Tax $611.04 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)
Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 04/08/2026. The listing information on this page last changed on 04/08/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 04/08/2026 12:01:38 AM EST) or Stellar MLS (last updated Tue 04/07/2026 11:44:07 PM EST). Real estate listings held by brokerage firms other than Wagner Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. 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.



Privacy Policy / DMCA Notice / ADA Accessibility

Login to My Homefinder

Pixel