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2832 Bear Island Pointe

WINTER PARK, FL 32792

5 beds
5 baths
3,983 sqft
10,667 sqft lot
$292 per sqft
1999 build
– on site

Welcome to 2832 Bear Island Pointe in Winter Park's premier gated community, Cypress Reserve! This meticulously maintained estate-like home is move-in-ready with 5 bedrooms plus a large office room with its own bathroom and separate exterior entry. Nestled near the serene Bear Gully Lake, this stunning residence offers the perfect blend of elegance, convenience, and resort-style living. The thoughtfully designed floor plan features a spacious first-floor primary suite with a spa-like ensuite, including double vanities, a soaking tub, a walk-in shower, and a generous walk-in closet (11x13 ft). A gourmet kitchen with granite counter tops and stainless steel appliances makes meal preparation effortless, while the formal living and dining rooms provide an ideal setting for entertaining. With five versatile bedrooms, there is plenty of space for guest rooms, home offices, a gym, or a library. High ceilings (11 feet) throughout the home enhance the open and airy feel. The laundry room is equipped with a stackable washer and dryer, built-in cabinets, and a sink for added convenience. The outdoor space is an entertainer’s dream, featuring a large screened-in pavered patio, an indoor pool and spa, and a built-in barbecue area perfect for hosting gatherings. A spiral staircase leads to a private balcony off the primary suite, offering a peaceful retreat with beautiful views. This home is also equipped with solar panels (owner owned), providing an energy-efficient solution that helps reduce utility costs while promoting sustainable living. Perfectly positioned between world-famous beaches and major attractions, this home is just minutes from top-rated schools, including UCF, Rollins College, Trinity Prep, and The Master's Academy. It also offers easy access to Orlando International Airport, premier healthcare facilities, and the scenic Seminole Trail. Experience the best of Winter Park living in this exceptional home. Schedule your private showing today.

Listing courtesy of STELLAR_MLS / COMPASS FLORIDA LLC

Last checked: Checking… • Last updated Apr 28, 2025 •

MLS# O6301897 —

The Building

Year Built:

1999
New Construction:

false
Construction Materials:

Block
Levels:

Two
Stories Total:

2
Roof:

Shingle
Foundation Details:

Slab
Building Area Total:

5183
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Built-in Features
Flooring:

Carpet
Additional Rooms:

Den/Library/Office
Fireplace:

true
Fireplace Features:

Gas

Room Dimensions

Living Area:

3983
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

From SR 417, take Aloma exit and head toward Winter Park, turn right on Bear Gully Road, which turns into Cypress Reserve, take a left on Bear Island Pointe.
Latitude:

28.620209
Longitude:

-81.26995
Coordinates:

-81.26995, 28.620209

The Property

Parcel Number:

36213051000000410
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size Acres:

0.24
Lot Size Area:

10667
Lot Size SqFt:

10667
Lot Size Units:

Square Feet
Total Acres:

0 to less than 1/4
Zoning:

R-1AA
Direction Faces:

North
View:

false
Exterior Features:

Lighting
Water Source:

Public
Road Surface Type:

Paved
Flood Zone Code:

x
Additional Parcels:

false
Homestead:

true
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

41
Tax Block:

x
Tax Legal Description:

LOT 41 CYPRESS RESERVE PB 50 PGS 10 & 11
Tax Book Number:

50-10
Tax Annual Amount:

$4,618.05

Beds

Bedrooms Total:

5

Baths

Total Baths:

5
Total Baths:

5
Full Baths:

5

The Listing

Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/O6301897
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Cable Connected
Sewer:

Public Sewer

Appliances

Appliances:

Dishwasher
Laundry Features:

Laundry Room

Schools

Elementary School:

Eastbrook Elementary
Middle Or Junior School:

Tuskawilla Middle
High School:

Lake Howell High

The Community

Subdivision Name:

CYPRESS RESERVE
Senior Community:

false
Community Features:

Gated Community - No Guard
Waterview:

false
Water Access:

false
Waterfront:

false
Spa:

true
Spa Features:

In Ground
Pool Private:

true
Pool Dimensions:

14x30
Pool Features:

Auto Cleaner
Pets Allowed:

Yes
Pet Restrictions:

Buyer and buyer agent to verify pet restrictions directly with HOA.
Association:

true
Association Fee:

1806
Association Fee Frequency:

Annually
Association Fee Requirement:

Required
Monthly HOA Amount:

150.5
Ownership:

Fee Simple
Association Approval Required:

false

Parking

Garage:

true
Attached Garage:

true
Garage Spaces:

3
Garage Dimensions:

20x21
Carport:

false
Covered Spaces:

3
Open Parking:

true
Parking Features:

Driveway

Monthly cost estimate

Asking price

$1,165,000

Expense	Monthly cost
Mortgage	$6,238
Taxes	$384
Insurance	$320
HOA fees	$151
Utilities	$268 See report
Total	$7,361/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Soundscore™

Provided by HowLoud

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
4/24/25 Apr 24, 2025	Listed / Active	STELLAR_MLS	$1,165,000	55.3% (14.8% / YR)
7/30/21 Jul 30, 2021		STELLAR_MLS	$750,000

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This house located in Cypss Reserve, FL 32792 is currently for sale for $1,165,000. 2832 Bear Island Pointe is a 3,983 square foot house with 5 beds and 5 baths that has been on Estately for 5 days. 2832 Bear Island Pointe is in the Cypss Reserve neighborhood of WINTER PARK and has a WalkScore® of 21, making it car-dependent. This house is in the attendance area of Tuskawilla Middle School, Lake Howell High School, and Eastbrook Elementary School.

Listing Courtesy of: STELLAR_MLS and COMPASS FLORIDA LLC.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing is provided exclusively 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. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.