Alice Anne Jackson
CORCORAN PREMIER REALTY
(689) 210-2240
43 Total Sales
1 in Bay Hill
$950,000 Price
5558 Brookline Dr Orlando, FL 32819
Bay Hill NeighborhoodEstimated Value: $2,542,000 - $2,640,873
5
Beds
4.5
Baths
5,822
Sq Ft
$444/Sq Ft
Est. Value
Highlights
- On Golf Course
- Oak Trees
- In Ground Pool
- Dr. Phillips Elementary School Rated A-
- Media Room
- Custom Home
About This Home
As of March 2026Appraisal in Hand! A Golfer’s Dream... Anyone’s Dream! This extraordinary estate sits on one of the most coveted lots in Arnold Palmer’s Bay Hill Golf & Country Club, overlooking holes #4, #5, and the iconic televised #6 with its shimmering water views. Words cannot capture the beauty, serenity, and prestige of this setting. Completely reimagined with luxury and comfort in mind, this 5,822 sq. ft. home offers 5 bedrooms, 4.5 baths, a home theater, game room, executive office, and a chef’s kitchen with dual refrigerators, three dishwashers, and a Miele coffee system. The outdoor retreat (renovated in 2022) features travertine decking, a resort-style pool and spa, summer kitchen, and retractable sun cover, all framing breathtaking sunsets. Upgrades include a new roof (2018), new HVAC (2023), updated electrical, and new paver driveway. Minutes from Bay Hill Club & Lodge, “Restaurant Row,” and top-rated schools, experience the ultimate in Florida luxury living. Schedule your private showing today!
Last Agent to Sell the Property
THE FLORIDA LOUNGE REALTY LLC Brokerage Phone: 786-241-7619 License #3435851 Listed on: 11/06/2025
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Home Details
Home Type
- Single Family
Est. Annual Taxes
- $35,840
Year Built
- Built in 2008
Lot Details
- 18,182 Sq Ft Lot
- On Golf Course
- Key Lot That May Back To Multiple Homes
- East Facing Home
- Fenced
- Mature Landscaping
- Native Plants
- Metered Sprinkler System
- Oak Trees
- Property is zoned R-1AA
HOA Fees
- $88 Monthly HOA Fees
Parking
- 3 Car Attached Garage
- Side Facing Garage
- Garage Door Opener
- Driveway
- Secured Garage or Parking
- Guest Parking
Property Views
- Pond
- Golf Course
- Pool
Home Design
- Custom Home
- Bi-Level Home
- Tudor Architecture
- Mediterranean Architecture
- Slab Foundation
- Slate Roof
- Block Exterior
- Stone Siding
- Stucco
Interior Spaces
- 5,822 Sq Ft Home
- Open Floorplan
- Wet Bar
- Central Vacuum
- Built-In Features
- Bar Fridge
- Cathedral Ceiling
- Non-Wood Burning Fireplace
- Decorative Fireplace
- Gas Fireplace
- Thermal Windows
- Blinds
- French Doors
- Sliding Doors
- Entrance Foyer
- Family Room with Fireplace
- Great Room
- Living Room
- Breakfast Room
- Formal Dining Room
- Media Room
- Den
- Bonus Room
- Game Room
- Inside Utility
Kitchen
- Breakfast Bar
- Walk-In Pantry
- Built-In Oven
- Range with Range Hood
- Microwave
- Dishwasher
- Wine Refrigerator
- Stone Countertops
- Solid Wood Cabinet
- Disposal
Flooring
- Wood
- Carpet
- Travertine
Bedrooms and Bathrooms
- 5 Bedrooms
- Split Bedroom Floorplan
- Studio bedroom
- Walk-In Closet
- Hydromassage or Jetted Bathtub
- Bathtub With Separate Shower Stall
- Garden Bath
Laundry
- Laundry in unit
- Dryer
- Washer
Home Security
- Security System Owned
- Fire and Smoke Detector
Eco-Friendly Details
- Energy-Efficient Thermostat
- Whole House Vacuum System
Pool
- In Ground Pool
- Gunite Pool
- Pool Tile
Outdoor Features
- Balcony
- Covered Patio or Porch
- Outdoor Kitchen
- Exterior Lighting
- Outdoor Grill
- Rain Gutters
Utilities
- Forced Air Zoned Heating and Cooling System
- Humidity Control
- Underground Utilities
- Electric Water Heater
- Cable TV Available
Community Details
- Beacon Management Association
- Bay Hill Sec 10 Subdivision
Listing and Financial Details
- Visit Down Payment Resource Website
- Legal Lot and Block 413 / 4
- Assessor Parcel Number 21-23-28-0550-04-130
Ownership History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Nov 6, 2025
Closed on
Mar 27, 2026
Sold by
Bought by
Seller's Agent
Jen Dantas
THE FLORIDA LOUNGE REALTY LLC
Buyer's Agent
TJ Agosto
EMPIRE NETWORK REALTY
List Price
$2,797,000
Sold Price
$2,562,000
Premium/Discount to List
-$235,000
-8.4%
Views
288
Current Estimated Value
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$21,468
Avg. Annual Appreciation
2.11%
Purchase Details
Closed on
Jan 18, 2017
Sold by
Bought by
Purchase Details
Listed on
Mar 31, 2012
Closed on
Jun 14, 2012
Sold by
Bought by
Seller's Agent
Scott Langevin
ORLANDO GOLF ESTATES
Buyer's Agent
LAURA BAUGH
List Price
$1,100,000
Sold Price
$1,100,000
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
6.20%
Purchase Details
Closed on
Dec 9, 2004
Sold by
Bought by
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Bay Hill, FL
-
Alice Anne Jackson
-
Cameron Hoch
Cameron Hoch
RESOLUTE DEVELOPMENT GROUP, LLC
(844) 723-1934
6 Total Sales
1 in Bay Hill
$1,600,000 Price
-
Tiphany Weeks
Tiphany Weeks
DIAMOND REAL ESTATE GROUP
(321) 204-3632
64 Total Sales
1 in Bay Hill
$685,000 Price
-
Adam Sortman
Adam Sortman
Boardwalk Realty, LLC
(321) 730-2352
85 Total Sales
2 in Bay Hill
$550,000 Price Range
-
Rob Aponte
Rob Aponte
Responds QuicklyREAL BROKER, LLC
(689) 215-8047
183 Total Sales
1 in Bay Hill
$850,000 Price
-
Toni Marie Cafferty
Toni Marie Cafferty
COMPASS FLORIDA LLC
(689) 407-6986
29 Total Sales
3 in Bay Hill
$575K - $889K Price Range
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $2,562,000 | Simplifile | ||
| $1,649,500 | None Available | ||
| $1,150,000 | None Available | ||
| $500,000 | -- |
Source: Public Records
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Previous Owner | $1,062,500 | ||
| Previous Owner | $200,000 | ||
| Previous Owner | $500,000 | ||
| Previous Owner | $350,000 |
Source: Public Records
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 03/27/2026 03/27/26 | Sold | $2,562,000 | -8.4% | $440 / Sq Ft | |
| 02/25/2026 02/25/26 | Pending | -- | -- | -- | |
| 11/06/2025 11/06/25 | For Sale | $2,797,000 | +154.3% | $480 / Sq Ft | |
| 06/16/2014 06/16/14 | Off Market | $1,100,000 | -- | -- | |
| 06/14/2012 06/14/12 | Sold | $1,100,000 | -- | $203 / Sq Ft | View Prior Sale |
Source: Stellar MLS
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $35,840 | $2,163,640 | $550,000 | $1,613,640 |
| 2025 | $35,840 | $2,190,370 | $550,000 | $1,640,370 |
| 2024 | $29,902 | $2,113,780 | $550,000 | $1,563,780 |
| 2023 | $29,902 | $1,997,660 | $550,000 | $1,447,660 |
| 2022 | $26,313 | $1,671,213 | $450,000 | $1,221,213 |
| 2021 | $24,505 | $1,524,938 | $450,000 | $1,074,938 |
| 2020 | $23,853 | $1,533,676 | $450,000 | $1,083,676 |
| 2019 | $25,370 | $1,542,414 | $450,000 | $1,092,414 |
| 2018 | $25,227 | $1,515,004 | $450,000 | $1,065,004 |
| 2017 | $21,354 | $1,291,762 | $295,000 | $996,762 |
| 2016 | $19,507 | $1,132,698 | $295,000 | $837,698 |
| 2015 | $19,970 | $1,130,497 | $280,000 | $850,497 |
| 2014 | $19,888 | $1,105,425 | $260,000 | $845,425 |
Source: Public Records
Agents Affiliated with this Home
-
Jen Dantas
JD
Seller's Agent in 2026
Jen Dantas
THE FLORIDA LOUNGE REALTY LLC
(407) 456-4820
1 in this area
74 Total Sales
-
TJ Agosto
Buyer's Agent in 2026
TJ Agosto
EMPIRE NETWORK REALTY
(407) 955-5539
1 in this area
40 Total Sales
-
Scott Langevin
Seller's Agent in 2012
Scott Langevin
ORLANDO GOLF ESTATES
(407) 592-7296
4 in this area
14 Total Sales
-
LB
Buyer's Agent in 2012
LAURA BAUGH
Map
Source: Stellar MLS
MLS Number: O6358772
APN: 21-2328-0550-04-130
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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. Some IDX listings have been excluded from this website. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed.
Listings courtesy of Stellar MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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