$519,000.00
1065 GREGORY DR, MAITLAND, FL - 32751
3 beds
2.0 baths
1,929 sqft
$519,000.00
1065 GREGORY DR, MAITLAND, FL - 32751
Jessica Giraldo
$519,000.00
3 beds
2.0 baths
1,929 sqft
1065 GREGORY DR, MAITLAND, FL - 32751
For Sale
Photo 1
  • Built in 1958
  • 2 garage spaces
  • $269.05/sqft
  • Lot size: 12,371 sqft
  • 13 days on market

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!

  • Directions: From the intersection of Maitland Ave and Maitland Blvd, head north on Maitland Ave. Turn left onto Oranole Rd, then turn left onto Gregory Dr. The property will be on your left.
  • County: Seminole
  • Geo subdivision: DRUID HILLS ESTATES 1ST ADD

Nearby Schools

Lake Orienta Elementary

Milwee Middle

Lyman High

Features

Financial

Let's get in touch!

Jessica Giraldo

Jessica Giraldo

Realtor®

See also

For Sale
2715 PRINCE JOHN ROAD, WINTER PARK, FL - 32792
$519,900.00
3 bds
2.0 ba
1,565 sqft
2715 PRINCE JOHN ROAD, WINTER PARK, FL - 32792
For Sale
504 TIVOLI COURT, ALTAMONTE SPRINGS, FL - 32701
$525,000.00
4 bds
2.5 ba
2,184 sqft
504 TIVOLI COURT, ALTAMONTE SPRINGS, FL - 32701
For Sale
2974 CHANTILLY AVENUE, WINTER PARK, FL - 32789
$550,000.00
3 bds
2.0 ba
1,433 sqft
2974 CHANTILLY AVENUE, WINTER PARK, FL - 32789
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6411336
Listing updated: June 9, 2026 at 9:18PM
Listing provided by: Cece Wong, EXP REALTY LLC
Last checked 9 hours ago
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