5558 Brookline Drive · Bay Hill · Orlando, FL
Champions come to Bay Hill a few days a year. Those who live here are familiar with this scene every day.
I'm Jen Dantas (Realtor in Orlando and the surrounding area), and this article is the "uncut" version of what we showed on the landing page—with more context, technical details, and a large selection of photos and videos.
Ad details as of Dec/2025; please confirm measurements, prices, and availability at the time of your visit.
(Official property page:) bayhill.jendantas.com)
“At 5558 Brookline Drive, you’re not just in Orlando. You’re sitting in the front row of golf’s most exclusive spectacle — and that row is in your living room.”
Strategic Highlights ⭐
- US$ 2,797,000List price (Dec/2025)
- 5,822 sq ftHeated area (approximately 541 m²)
- 5 bedrooms · 4.5 bathroomsPrivacy for family and guests
- 0.42 acresWell-used lot (approximately 1,689 m²)
- Open view + lakeA field as a backyard and water in the background.
- Roof 2020 · HVAC 2023Updates that reduce post-key surprises
The batch that few manage to replicate ⛳
I'm saying this quite frankly for those seeking high standards: the finish can be updated. Land and location, no. And this is exactly where the game changes. 5558 Brookline Drive is in a spot that offers open views of the countryside and, at the same time, the presence of the lake in the background, which completely changes the feeling of depth and silence.
🎯 “Front row” at Bay Hill
Direct view of holes 4, 5 and the legendary 6. This isn't just an aesthetic detail — it's positioning.
🌅 Lake in the background
The reflection of the sunset on the water creates a resort-like atmosphere, even when the house is full.
🧭 Sense of command
You see the field, the water, and the outdoors as a "stage" that you control: light, shadow, flow, and rhythm.
Preview in photos (view & aerial views)
The inner strength: to live, to decide, and to receive 🏛️
Inside, I like to describe this house as a "comfortable fortress." It wasn't designed to look big just in photos—it functions when life happens: family, guests, remote work, meetings, relaxation, and yes, real entertainment.
🎬 Home theater
A space that delivers a cinematic immersion without relying on a "makeshift multipurpose room".
🎮 Game / media room
Separate environments for each mood: chatting, playing games, watching videos, and disconnecting from the world.
💼 Executive office
Privacy for decisions and calls, without you having to "disappear" from home to work well.
🛏️ 5 suites / privacy
I love it when a high-end home respects routine: rest, guests, and circulation without conflict.
Interiors — selection (social + details)
Home cinema 🎬
The kitchen as a "war room" ☕
There's a reason why I keep stressing this: in a house of this caliber, the kitchen isn't just a room. It's the heart of the operation. And here, it was designed to accommodate discerning guests without causing any backstage chaos. I see many "beautiful" houses that collapse at the first dinner party—this isn't one of them.
🧊 2 refrigerators
Real-life event flow: drinks, desserts, storage, and routine without improvisation.
🍽️ 3 dishwashers
When the house is full, the luxury is ending the day without having to "pay the bill" with work.
☕ Café Miele
For those who take coffee seriously — and understand that details are also part of positioning.
The private resort in your backyard 🌅
In 2022, the outdoor area was transformed into being a private club.And I like this point: while many people in Orlando go "hunting" for a beautiful sunset, here you just take a few steps, turn on the lights, and the countryside and the lake do the rest. This isn't just leisure. It's the house working in your favor.
🏖️ Travertine
Elegant, timeless, and consistent with the Bay Hill standard.
💦 Pool + spa
Resort design, with framing carefully considered to complement the background scenery.
🔥 Summer kitchen
Integrated gourmet area for entertaining without "traffic" inside the house.
⛱️ Retractable cover
Sun and shadow under your control — it's that simple.
Pool & backyard
View from the balcony (2nd floor)
The invisible luxury: structure and maintenance 🛠️
This is the kind of part I make a point of showing during the visit, because it's where the experienced buyer distinguishes between a "beautiful house" and a "house ready for the next few years." Here you have a package of upgrades that reduces risk and increases control—especially for those who travel a lot or are buying as a second home.
✅ Key updates
New roof (2020) · Upgraded HVAC (2023) · Upgraded electrical system · Paver driveway.
🧠 What does this mean in practice?
Less "expensive surprises" after the key is installed and more predictable maintenance.
Acronyms & terms (for quick reading)
HOA: condominium association fee.
sq ft: square feet (a unit of area in the US).
HVAC: Heating, ventilation and air conditioning.
Paver: Interlocking paving stones (very commonly used in driveways).
Zone X: Common classification in flood maps; confirm on the current map and in due diligence.
Strategic property details sheet 📋
Reference period: December 2025. Values and measurements should be confirmed at the time of the visit and in the official documentation.
| Item | Information |
|---|---|
| Address | 5558 Brookline Drive, Orlando, FL 32819 |
| List price | US$ 2,797,000 |
| Heated area | 5,822 sq ft (about 541 m²) |
| Total area | 7,699 sq ft (about 715 m²) |
| Bedrooms / bathrooms | 5 bedrooms · 4.5 bathrooms |
| Year of construction | 2008 |
| Batch | 0.42 acres (about 1,689 m²) |
| Pool | Private resort-style pool + spa |
| Garage | Up to 4 cars (rear and side access) |
| HOA (approx.) | approximately US$ 1.125/year |
| Annual taxes (estimated) | approximately US$ 35,840 (2025 estimates) |
| Updates | Roof (2020) · HVAC (2023) · Updated electrical system · Paver driveway |
| Emphasis | Direct view of holes 4, 5 and the iconic 6 + lake in the background. |
Main sources for the conference: official property page, Orange County Property Appraiser and FEMA Flood Map Service Center.
Videos: tour + interview 🎥
Full tour
I recommend watching it carefully to understand the true flow of the house.
Interview (Open House)
Behind the scenes of why this plot of land and this view are so rare.
Extended gallery 🖼️
Here's a comprehensive selection organized by "chapters," so you can navigate as if you were walking through the house. (All images open in larger size when clicked.)
Facade & arrival
Master suite (selection)
Office & workspaces
Seu próximo palco
Whoever opens the right door (in the right Bay Hill) 👋
Jen Dantas
Corretora de imóveis brasileira licenciada na Flórida, formada em Direito no Brasil e com experiência em gestão de fortunas no setor bancário internacional. Minha missão é simples: fazer você comprar seu imóvel em Orlando com segurança jurídica, estratégia financeira e zero sustos na hora de assinar.
I work in Orlando, focusing on high-end properties and serving local and international clients (including Brazilians). In a market where "opening doors" is easy, I take you to the part that really matters: lot analysis, technical risk assessment, negotiation, and strategy.
Jen Dantas & The Florida Lounge
You can visit Bay Hill… or you can take control of your life from here.
If this view is the perfect setting for your next chapter, let's arrange a private tour.
Frequently Asked Questions ❓
What makes this view "rare" in Bay Hill?
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