5558 Brookline Dr

Off Market

5558 Brookline Dr

Bay Hill FL 32819

7699 sq. ft.

18182 sq. ft.

Single-Family

Last sold for $2,562,000

Jen Dantas, last sold this property on 27 March 2026 after 1487 days on market.

Overview

Appraisal 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!

Features

5 bedrooms

5 bathrooms

3 carspaces

3 garage spaces

7699 sq. ft. floor area

18182 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Bay Hill over the last 12 months, the estimated median property value of 5558 Brookline Dr is $1.09m.

Median value

$1.09m

Estimated value range

$590k - $5.05m

Median days on market

Estimated value trend

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Bay Hill. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 5558 Brookline Dr

2026

Sold

$2,562,000

27 Mar 2026 by Jen Dantas, of THE FLORIDA LOUNGE REALTY LLC

2017

Sold

$1,649,500

18 Jan 2017 by Deanna Armel, of ARMEL REAL ESTATE INC

2017

Sold

$1,649,500

18 Jan 2017 by Deanna Armel

Happy sellers in Bay Hill

84%

84% of sellers in Bay Hill reported that their sale price either exceeded or met their price expectations.

Bay Hill stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 12 reviews in Bay Hill over the last 12 months.

Local market activity for 5 bedroom single-family properties in Bay Hill

In the last 12 months, 37 five-bedroom single-family properties similar to 5558 Brookline Dr, have been sold.

This represents a 25% decrease in five-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Bay Hill for a market analysis.

Tami Ihya

at TOWNE CENTER REALTY

(73 reviews)

Get a market analysis

Gabriela Buche

at VISTA CAY REALTY COMPANY

(12 reviews)

Get a market analysis

George Stringer

at Coldwell Banker Residential Re

(8 reviews)

Get a market analysis

Erica Diaz

at Erica Diaz Team

(633 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Bay Hill

Tami Ihya

Sellers who recommend Tami Ihya have praised them for being local expert, patient, responsive, clear communication, dedicated, reliable, and supportive