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5558 Brookline Drive

ORLANDO, FL 32819

5 beds
5 baths
5,822 sqft
~1/2 acre lot
$546 per sqft
2008 build
– on site

Luxury Bay Hill Estate on Arnold Palmer’s Championship Golf Course A rare opportunity to own a meticulously upgraded luxury estate in the heart of Bay Hill, just steps from the world-renowned Bay Hill Club & Lodge. This exquisite 5-bedroom, 4.5-bathroom residence features a dedicated home office, a private cinema with premium acoustic design, and a game room with breathtaking golf course views. Positioned on a prime golf course lot, the home offers panoramic vistas of multiple fairways and greens. Every detail has been thoughtfully curated and impeccably maintained, with high-end home automation that blends elegance and convenience across the living and entertainment spaces. Grand Entrance – A striking custom glass front door opens to soaring ceilings, elegant beige travertine flooring, and full-height glass doors framing spectacular views. Primary Suite Retreat – A peaceful sanctuary with a spa-style bathroom featuring soft-toned cabinetry, Calacatta marble countertops, custom-framed mirrors, a soaking tub, a walk-in rain shower with golf course views, and dual walk-in closets. Chef’s Kitchen & Family Room Remodel (2017) – Designed for style and functionality, this kitchen features refined beige cabinetry with soft-close drawers, a dramatic Nero Marquina island, two full-size refrigerators, and three dishwashers (one traditional and two drawer-style). Additional highlights include a gourmet warming drawer, a Terminator professional gas range with four burners, a griddle, and a grill, as well as a built-in Miele Italian coffee system. Café Advantium appliances and an electric fireplace add charm and warmth to the family space. Entertainment & Smart Features • Game Room – Equipped with a premium built-in sound system for an immersive experience. • Private Home Theater – With Sony technology for a true cinematic atmosphere. • Advanced Home Automation – Over $40,000 invested in a system offering seamless control of lighting, climate, and security. Resort-Style Outdoor Living In 2022, a complete exterior renovation was completed with an investment of approximately $300,000. • Expansive Lanai – Travertine flooring, retractable electric sun cover, and unobstructed golf views. • Open Chlorine Pool & Spa – Designed for luxury and relaxation, with dual water bowls, a central fountain, and sun shelf. • Summer Kitchen – Featuring granite countertops and a stainless steel grill, perfect for entertaining. Recent Upgrades & Capital Improvements • Three A/C Units – Replaced in intervals: one recently, one two years ago, another three years ago. • New Garage Door – Installed three years ago for added security and convenience. • Updated Electrical System – Fully rewired and modernized two years ago. • Boral Slate Tile Roof (2020) – Durable and visually striking. • 6-Ton Multi-Speed Carrier HVAC (2023) – High-efficiency performance. • New Paver Driveway & Walkways (2023) – Enhancing curb appeal and function. • Central Vacuum System – Pre-installed (currently deactivated). • Modern LED Hallway Lighting – Energy-efficient with clean, contemporary appeal. Prime Location & Exclusive Lifestyle. Located in Orlando, this residence offers unmatched proximity to the Bay Hill Club & Lodge, world-class golf, fine dining, upscale shopping, and top-rated schools. Experience refined Florida living at its finest.

Listing courtesy of STELLAR_MLS / SELECTA REALTY LLC

Last checked: Checking… • Last updated Apr 15, 2025 •

MLS# O6280345 —

The Building

Year Built:

2008
New Construction:

false
Construction Materials:

Block
Building Elevator:

false
Levels:

Two
Stories Total:

2
Roof:

Slate
Foundation Details:

Slab
Window Features:

Blinds
Security Features:

Closed Circuit Camera(s)
Floor Number:

2
Building Area Total:

7699
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Built-in Features
Flooring:

Ceramic Tile
Fireplace:

true
Fireplace Features:

Decorative

Room Dimensions

Living Area:

5822
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

From I-4 East or West, take Exit 74A for Sand Lake Rd (FL-482). Head west on Sand Lake Rd for about 2.5 miles. Turn left onto Dr. Phillips Blvd and continue for 1 mile. Turn right onto Wallace Rd and drive for 0.5 miles. Turn left onto S Apopka Vineland Rd and go 0.2 miles. Turn right onto Bay Hill Blvd and continue for 0.8 miles. Turn left onto Brookline Dr. 5558 Brookline Dr will be on your right.
Latitude:

28.469926
Longitude:

-81.50751
Coordinates:

-81.50751, 28.469926

The Property

Parcel Number:

212328055004130
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size Acres:

0.42
Lot Size Area:

18182
Lot Size SqFt:

18182
Lot Size Units:

Square Feet
Total Acres:

1/4 to less than 1/2
Zoning:

R-1AA
Direction Faces:

East
View:

Golf Course
View:

true
Exterior Features:

Balcony
Fencing:

Fenced
Vegetation:

Trees/Landscaped
Water Source:

Public
Road Surface Type:

Asphalt
Flood Zone Code:

X
Additional Parcels:

false
Homestead:

false
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

413
Tax Block:

4
Tax Legal Description:

BAY HILL SECTION 10 7/97 LOT 413
Tax Book Number:

7-97
Tax Annual Amount:

33624

Beds

Bedrooms Total:

5

Baths

Total Baths:

4.5
Total Baths:

5
Full Baths:

4
Half Baths:

1

The Listing

Virtual Tour URL Unbranded:

https://www.propertypanorama.com/instaview/stellar/O6280345
Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Cable Available
Sewer:

Public Sewer

Appliances

Appliances:

Built-In Oven
Laundry Features:

Laundry Closet

Schools

Elementary School:

Dr. Phillips Elem
Middle Or Junior School:

Southwest Middle
High School:

Dr. Phillips High

The Community

Subdivision Name:

BAY HILL SEC 10
Senior Community:

false
Community Features:

Golf
Waterview:

Pond
Waterview:

true
Water Access:

false
Water Body Name:

LAKE TIBET BUTLER
Waterfront:

false
Spa:

false
Pool Private:

true
Pool Features:

In Ground
Pets Allowed:

Yes
Association:

true
Association Fee:

700
Association Fee Frequency:

Annually
Association Fee Requirement:

Required
Monthly HOA Amount:

58.33
Ownership:

Fee Simple
Association Approval Required:

true

Parking

Garage:

true
Attached Garage:

true
Garage Spaces:

4
Carport:

false
Covered Spaces:

4
Open Parking:

true
Parking Features:

Covered

Extra Units

Other Structures:

Outdoor Kitchen

Monthly cost estimate

Asking price

$3,179,393

Expense	Monthly cost
Mortgage	$17,024
Taxes	$2,802
Insurance	$874
HOA fees	$58
Utilities	$303 See report
Total	$21,061/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
4/15/25 Apr 15, 2025	Price Changed	STELLAR_MLS	$3,179,393	-3.7%
3/3/25 Mar 3, 2025	Listed / Active	STELLAR_MLS	$3,300,000
8/14/11 Aug 14, 2011	Sold	STELLAR_MLS

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This house located in Sand Lake Hills, Doctor Phillips, FL 32819 is currently for sale for $3,179,393. 5558 Brookline Drive is a 5,822 square foot house with 5 beds and 5 baths that has been on Estately for 49 days. 5558 Brookline Drive is in the Sand Lake Hills neighborhood of Doctor Phillips and has a WalkScore® of 17, making it car-dependent. This house is in the attendance area of Cornerstone Charter Academy K-8, Dr. Phillips High School, Dr. Phillips Elementary School, Southwest Middle School, and Cornerstone Charter Academy High School.

Listing Courtesy of: STELLAR_MLS and SELECTA REALTY 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.