1108 Fairway Drive Winter Park, Florida
A mid-century home, reimagined for how people actually live now.
Built in 1978 and recently renovated, 1108 Fairway sits in Golfside Section 3, one of those quiet Winter Park pockets that doesn't make the headlines but keeps the long-term value. The renovation is restrained where it needs to be and ambitious where it counts.
The kitchen is the obvious centerpiece. Taj Mahal quartzite, custom white oak cabinetry, champagne bronze fixtures. The kind of choices that read as intentional rather than trendy. Luxury vinyl plank runs throughout, the tile work in the wet areas is cohesive, and the bonus room reads as a real office, not a closet with a desk shoved in.
What this home could cost you every month.
Zillow's monthly estimate leaves out homeowner's insurance entirely. In Florida, that's not a rounding error. Move the sliders below to get a rough idea for your situation. Real numbers will depend on your lender, your credit, and your actual insurance quote.
⚠ A heads up on property taxes
The monthly tax figure above reflects the current owner's 2024 bill of $6,713 a year. In Florida, taxes can reassess once the home changes hands, and there are a few variables that affect where your actual number lands: purchase price, homestead exemption status, Save Our Homes cap transfers, and county millage rates. I'll make sure you're aware of any potential estimated increases before you write an offer, so there aren't any surprises.
A neighborhood has a rhythm. Here's what yours would be.
Every home has a neighborhood, but a neighborhood has a rhythm. The coffee, the trails, the Saturday morning places. These are the spots within roughly 5 minutes of 1108 Fairway. If you lived here, this is your life.
Winter Park Pines Golf
Public course, clubhouse for casual dining, regulars out most mornings. The neighborhood was built around this.
Foxtail Coffee
Your default. Local Florida chain, good cold brew, decent breakfast. You'll become a regular.
Bagel King
Winter Park institution. Go early, order the egg-and-cheese, don't overthink it.
Publix at Aloma Walk
The Florida staple. You will know the layout by week two of living here.
Trader Joe's
Slightly outside the 5-min, but worth the drive. Makes weeknight cooking easier.
The Porch
Neighborhood casual American. The kind of place you end up at on a random Tuesday.
4Rivers Smokehouse
The original location of the Florida BBQ chain. Ribs, brisket, bread pudding, the whole deal.
Cady Way Trail
Paved rail-trail running all the way to Baldwin Park. Bikes, strollers, dogs. The artery of this side of town.
Ward Park
Tennis courts, open fields, dog-friendly. Quiet neighborhood park, not a destination.
Park Avenue
Saturday farmer's market, the Morse Museum, Prato, Bosphorous, bookstores. The reason Winter Park has the reputation it has.
The homes I've walked, and what stood out.
this week
1108 Fairway Drive Featured
The kitchen is doing real work. Taj Mahal quartzite and white oak cabinets, restrained in a way most flip kitchens aren't. The screened pool is the bigger version of what everyone in Central Florida is trying to get.
A buyer who wants the Winter Park address with a little more space and more recent upgrades than what the same price gets you in 32789. You're trading zip-code prestige for actual square footage and a renovated home.
The location earns its premium in three ways at once: the Winter Park Pines golf course out front, Cady Way Trail at the back, and a straight shot to Baldwin Park's restaurants, shops, and Lake Baldwin. Most listings in this price range give you one of those amenities. This gives you all three.
Want to see 1108 Fairway in person?
Shoot me a DM on Instagram, or reach out through my website and I'll set up a private showing. No pressure, no scripts.