#O6274006, Matt Tomaszewski, Listing office: CORCORAN PREMIER REALTY
5558 Brookline Dr Orlando, FL 32819
Property details
About 5558 Brookline Dr
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.
Highlights
Virtual tour
Summary
- Partial Bathrooms: 1
- Full Bathrooms: 4
- Appliances: Oven, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer
- Flooring Type: Ceramic Tile, Wood
- Interior: Built-in Features, Ceiling Fans(s), Central Vaccum, Crown Molding, Walk-In Closet(s)
- Fireplace: Decorative, Family Room, Gas, Non Wood Burning
- Total Bedroom Count: 5
- Garage Space: 4 spaces
- Attached Garage: Yes
- Private Pool: Yes
- Parking: Covered, Driveway, Garage Door Opener
- View: Golf Course
- Exterior: Balcony, Outdoor Grill, Sliding Doors
- Heating: Central
- Cooling: Central Air
- List Price: $2,985,500
- Price/SqFt: $512
- HOA Amount: $700 Annually
- Annual Tax Amount: $29,902
- Tax Year: 2023
- 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.
- Year Built: 2008
- Stories: 2
- Living Area: 5,822 SqFt
- Lot Size: 0.42 Acres
- MLS Number: O6280345
- MLS Name: MFRMLS
- Office Name: SELECTA REALTY LLC
- Office Phone: (407) 777-7131
- Listing Agent: Marcella Reginato
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Price information
Property sales
Date | Event | Price |
---|---|---|
Jan 20, 2017 | Home Sold | $1,649,500 |
Jun 20, 2012 | Home Sold | $1,150,000 |
Dec 29, 2004 | Home Sold | $500,000 |
Tax history
Year | Assessment | Property Tax |
---|---|---|
2023 | $1,997,660 | $29,902 |
2022 | $1,671,213 | $26,312 |
2021 | $1,524,938 | $26,312 |
2020 | $1,533,676 | $24,505 |
2018 | $1,515,004 | $25,226 |
2017 | $1,291,762 | $21,354 |
History based on county public records data.
Nearby schools
8
Palm Lake Elementary School
Public District KG-5
1.3 mi
•8000 Pin Oak Dr
9
Dr. Phillips Elementary School
Public District KG-5
1.3 mi
•6909 Dr Phillips Blvd
9
Bay Meadows Elementary School
Public District KG-5
2.5 mi
•9150 S Apopka Vineland Rd
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $118,840. The majority of Orlando, FL residents have income between $100k-200k annually. The majority of families are married, no kids. Residents of this area typically have post secondary degree education.
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Frequently asked questions
About 5558 Brookline Dr
The listing price of 5558 Brookline Dr property is $2,985,500.
The property 5558 Brookline Dr is a house located in Orlando, Florida, 32819.
Active Listing: 5558 Brookline Dr is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 5558 Brookline Dr are: Palm Lake Elementary School (GreatSchools Rating 8/10), Dr. Phillips Elementary School (GreatSchools Rating 9/10), Bay Meadows Elementary School (GreatSchools Rating 9/10), Southwest Middle School (GreatSchools Rating 7/10), Chain of Lakes Middle School (GreatSchools Rating 3/10), Windy Ridge School (GreatSchools Rating 8/10), Dr. Phillips High School (GreatSchools Rating 5/10), Olympia High School (GreatSchools Rating 6/10), Universal Education Center (GreatSchools Rating 4/10).
According to the records, the last property tax for 2023 is $29,902 (source: MLS/based on county public records data).
The last sale was on January 20, 2017 for $1,649,500 (source: MLS/tax record).
The property at 5558 Brookline Dr has 5 bedrooms and 4 full and 1 half bathrooms.
The property 5558 Brookline Dr is 5,822 SqFt (source: MLS/tax record).
The year of construction for 5558 Brookline Dr is 2008.
This home is located at 5558 Brookline Dr in Orlando, FL and zip code 32819 in the Bay Hill neighborhood. This 5,822 square foot home, which was built in 2008, sits on a 0.42 acre lot. Features: 5 bedrooms, 5 bathrooms. It has been listed on Rocket Homes since March 3, 2025 and is currently priced at $2,985,500.
While more than 103 listings in Orlando, FL in June 2025 were sold above asking price, there were more than 214 listings sold at asking price, and more than 548 were sold below. The number of listings in Orlando, FL increased by 2.3% between May and June 2025. In June 2025, listings were on the market for 58 days. During the same period, the median list price in this real estate market was $395,402.