Some homes feel special the moment you arrive. Beneath mature oak trees draped in Spanish moss, 1060 Gregory Drive offers the kind of character, warmth, and sense of place that is increasingly difficult to find.
Built in 1962 and located in an established Maitland neighborhood, this charming 3-bedroom, 2-bath home blends original architectural character with thoughtful updates, giving you a home that feels timeless while providing the comfort and improvements today’s buyers appreciate.
A Home with Character You Can Feel
Imagine coming home beneath a canopy of mature oaks, stepping through the front door, and being greeted by warm hardwood floors and architectural details that tell a story.
One of the home’s most memorable features is the dramatic brick feature wall separating the living and family rooms, complete with a fireplace facing each space. It’s an unexpected detail that gives both rooms their own personality while creating inviting spaces for relaxing, gathering, and entertaining.
This isn’t a home designed to look like every other house. Its character is part of what makes it special.
A Kitchen Ready for Everyday Life
The updated kitchen combines classic style with modern functionality.
Shaker-style cabinetry, granite countertops, and stainless steel appliances create a practical and welcoming space for everything from quick weekday breakfasts to dinners with friends.
Throughout the home, plantation shutters and ceiling fans add comfort while complementing the home’s timeless aesthetic.
Your Private Retreat
The primary bedroom offers a comfortable escape with dual closets and an ensuite bathroom.
The guest bathroom has also been refreshed with a new vanity, adding another layer of modern convenience for family and guests.
With three bedrooms and two full bathrooms, the floor plan offers flexibility for a growing household, visiting guests, or a dedicated home office.
Take the Living Outside
Step through to the expansive backyard deck and imagine warm Florida evenings spent beneath the trees.
There’s plenty of space for outdoor dining, entertaining friends, enjoying your morning coffee, or simply slowing down at the end of the day.
Surrounded by mature landscaping, the backyard provides a peaceful setting that feels private while remaining close to everything Maitland and Winter Park have to offer.
Major Updates for Added Peace of Mind
While the home celebrates its original character, important systems have been thoughtfully updated over the years.
Recent improvements include:
✨ Electrical update — 2026
✨ All-new ductwork — 2026
✨ Repiped — 2009
✨ New fence — 2023
✨ Water heater — 2022
✨ HVAC — 2020
✨ Roof — 2020
These improvements allow you to enjoy the character of an established home while benefiting from significant modern updates.
A Location That Keeps You Connected
Living at 1060 Gregory Drive means enjoying the established charm of Maitland while staying conveniently connected to Central Florida.
With quick access to Winter Park, Maitland, and Interstate 4, you’re close to shopping, dining, entertainment, employment centers, and everything else the area has to offer.
Come Experience It for Yourself
The best way to appreciate this home is to walk through it, experience the character of the architecture, and spend a moment beneath those beautiful mature oaks.
Join us for an open house or schedule your private showing of 1060 Gregory Drive today.
🏡 Open House Weekend
Friday, October 2 | 5:00 PM–7:00 PM
Saturday, October 3 | 1:00 PM–4:00 PM
Sunday, October 4 | 1:00 PM–4:00 PM
Come see why this tree-lined Maitland home could be the place you’ve been looking for.
Park Life Orlando
Jill Healey, MBA, Realtor®
407-797-1420
jillhealey@kw.com
Click here for more photos and info!
📍 1060 Gregory Drive, Maitland, FL 32751
💰 $529,000
🛏️ 3 Bedrooms | 🛁 2 Baths | 📐 1,734 Sq. Ft.
#MaitlandFL #MaitlandRealEstate #WinterParkRealEstate #CentralFloridaRealEstate #JustListed
