Location: Druid Hills Estates 1St Add, Maitland
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1055 DRUID DR, MAITLAND, FL 32751
$549,000Listed 07/13/2026 2:25PM MLS ID: O6424543
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1684 Built: 1959 Tax: $2,557 (2025)Community: Druid Hills Estates 1St AddSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,557
Elementary School: Lake Orienta Elementary
High School: Lyman High
Tax Year: 2025
Middle School: Milwee Middle
Remarks: Welcome home to this charming 3-bedroom, 2-bath pool home nestled in the highly sought-after Druid Hills Estates, one of Maitland’s most desirable neighborhoods. Set on an oversized wide lot along a picturesque street lined with majestic oak trees, this beautifully maintained home offers timeless character, thoughtful updates, and exceptional indoor-outdoor living. Inside, you’ll be welcomed by original hardwood floors that flow throughout the home, creating warmth and charm from the moment you step inside. The beautifully updated kitchen, renovated in 2019, is both stylish and functional, featuring propane service to the stove, newer appliances replaced in 2023, and an open flow into the living and dining area—perfect for everyday living and entertaining alike. Just beyond the main living space, the expansive Florida room is filled with natural light and features French doors that open to your private backyard oasis. Whether you’re hosting weekend gatherings or enjoying a quiet evening at home, the outdoor space is sure to impress with a sparkling pool, outdoor shower, fully fenced backyard, dedicated boat parking, and plenty of room for gardening, pets, or play. All three bedrooms are conveniently located together down the hall, creating a comfortable and private retreat. The bathrooms were tastefully remodeled in 2023, and additional updates provide peace of mind, including a new HVAC system (2023), a roof that’s just three years old, and a propane water heater. The septic drain field was replaced in 2019, and the septic system was professionally flushed just one year ago. Storage is abundant with an inside laundry room, built-in garage shelving, and a spacious attic for all your storage needs. Ideally located in a quiet pocket of Maitland with no HOA, you’ll enjoy easy access to the shopping, dining, parks, and entertainment of both Winter Park and Altamonte Springs while coming home to the peaceful charm of this established neighborhood. With the new Trader Joe’s planned just five minutes away, this location continues to become even more desirable. Blending classic character with modern updates and an incredible outdoor lifestyle, this move-in-ready Maitland pool home is one you won't want to miss!
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Justin Harvey (407-493-3086)
1065 GREGORY DR, MAITLAND, FL 32751
$519,00046 Days on yellowkey MLS ID: O6411336
0 Days Off yellowkey (back on 7/10/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1929 Built: 1958 Tax: $5,684 (2025)Community: Druid Hills Estates 1St AddSingle Family
Taxes:$5,684
Remarks: VIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home features 3 bed/2 bath in the main house with a 4th room addition on the other side of the garage. The 4th room has it's own separate entrance and it's own rear door access to the pool! Use it as a home office, creative studio, home gym, or income-producing suite — with no HOA to answer to. The cozy fireplace, hardwood floors, and split bedroom floor plan makes it feel like home. The oversized rectangular pool and deck were recently resurfaced and a screen enclosure was added to make maintenance a breeze. There’s still plenty of backyard space to enjoy on the huge 0.28 acre lot equipped with a white vinyl fence and storage shed. Minutes from excellent Maitland private schools and the Winter Park private school corridor, you’ll love the area! It’s close to Trader Joe’s, Winter Park Shopping & Dining, Audubon Center for Birds of Prey, Maitland Art Center, Lake Lily Park, and Enzian Theater. The RDV Sportsplex Athletic Club — with 400+ monthly classes — is an incredible convenience as well! Highway I-4 is close by and the SunRail Maitland Station is only 1 mile away, making downtown Orlando just 24 min commute on the Sunrail. Downtown Maitland is walkable with acclaimed restaurants anchored by a weekly Farmers' Market and the annual Jazz & Blues Festival. Roof is 2020, and water heater is brand new 2026. To see more of the house, WATCH THE VIDEO/VIRTUAL TOUR!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Cece Wong (407-809-1440)
1010 GREGORY DR, MAITLAND, FL 32751
$520,00047 Days on yellowkey MLS ID: O6411422
0 Days Off yellowkey (back on 6/1/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2227 Built: 1969 Tax: $4,288 (2025)Community: Druid Hills Estates 1St AddSpa: NoSingle Family
Taxes:$4,288
Remarks: Nestled in the heart of highly desirable Maitland, this spacious 4-bedroom, 2-bath pool home offers the perfect blend of location, functionality, and outdoor living on an oversized .28-acre lot with more than 12,000 square feet of property. Surrounded by mature trees and established neighborhoods, this prime location places you just minutes from Downtown Maitland, Historic Winter Park, Downtown Orlando, world-class shopping, dining, entertainment, and Central Florida’s renowned attractions. Maitland is loved for its charming restaurants, weekend farmer’s market, beautiful lakes, and scenic tree-lined streets, all while bordering some of the most prestigious real estate in Central Florida.The backyard is truly the showstopper of this property, featuring a sparkling open pool, beautiful vinyl fencing, and an expansive yard that is far larger than many homes in the area. Recent landscaping enhancements include a hardscaped entertaining space and decorative stone half wall, creating the perfect setting for relaxing, hosting guests, or enjoying Florida outdoor living under the shade of the beautiful oak tree.Inside, the home features a desirable split-bedroom floor plan with formal living and dining rooms, plus a spacious family room offering plenty of flexibility for everyday living and entertaining. The galley-style kitchen is equipped with granite countertops and overlooks the living areas for easy functionality. Attractive laminate wood flooring and tile flow throughout the home, while all bedrooms have been updated with new ceiling fans. Additional improvements include electrical upgrades, new exterior doors, a new roof installed in 2020, and added attic insulation for enhanced energy efficiency. Built with sturdy concrete block construction, this home offers lasting durability and peace of mind. The indoor laundry room includes the washer and dryer for added convenience. This is a rare opportunity to own a pool home with a large backyard in one of Central Florida’s most established and desirable locations.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kelly Hildebrand (407-310-5035)
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