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$525,000
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Property Description
One or more photo(s) has been virtually staged. Welcome to this stunning 5-bedroom, 2.5-bathroom mid-century gem! Boasting 2,289 sq ft of living space, this home offers a unique blend of modern updates and timeless charm. The open floor plan features a cozy living room with a fireplace that separates the bonus room, providing a versatile space for a formal dining area, playroom, study, or breakfast nook. The kitchen, with a direct open door to the bonus room, is perfect for entertaining and family gatherings with ample open space connected to a dining area in front of the double sliding door to the covered patio and pool, as well as the living room. The home's layout is designed for comfort and privacy, with four bedrooms and 2 full bathrooms conveniently located on the right side and a fifth bedroom with a half bath on the left, ideal for guests or a live-in relative. Enjoy the beauty of porcelain tile throughout, complemented by new travertine tile in the foyer. Recent updates include freshly painted interiors and exteriors, a new refrigerator, microwave, and 2 new bathroom sinks. Outdoor living is a delight with a large screened-in pool, replastered, and freshly painted pool deck in October 2023, perfect for relaxing and entertaining. The expansive patio and covered porch offer protected spaces for dining and lounging, rain or shine. Enhanced by new landscaping, exterior lighting, and motion/security lights, the home's exterior is as inviting as the interior. Practical features include a spacious shed for additional storage (15.9'x9.3'), a fully fenced yard, and a 2-car garage with a built-in closet and laundry area. An efficient AC unit installed in 2018 ensures year-round comfort, and the septic tank was serviced in May 2024 for peace of mind. The roof is fairly new from 2016. Located just 15 minutes from Winter Park and Downtown Orlando, easy access to 414, the expressway, and I-4, and a little over an hour to the beach, this beautiful home offers both convenience and tranquility. Don't miss out on the opportunity to own this meticulously maintained and updated property.
Full Property Details
Full Property Details for 1030 Gregory Dr
General
- Sold For: $525,000
- Taxes: $4,982 (2023)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6208703
- Added to Site: 584 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 13
- Interior Features: Crown Molding, Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Thermostat
- Fireplace: Yes
- Fireplace(s): Family Room, Living Room, Masonry, Wood Burning
- Appliances: Cooktop, Dishwasher, Disposal, Electric Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator
- Furnishings: Unfurnished
- Flooring: Porcelain Tile
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Electric Dryer Hookup, In Garage, Washer Hookup
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, In Ground, Lighting, Screen Enclosure
- Security/Safety: Security Lights
Exterior
- Exterior Features: Irrigation System, Lighting, Outdoor Shower, Private Mailbox, Rain Gutters, Sliding Doors, Sprinkler Metered, Storage
- Deck/Patio: Covered, Enclosed, Patio, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Enclosed, Patio, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Curb Parking, Driveway, Garage Door Opener, Ground Level, Off Street, On Street
Location
- Area: 32751 - Maitland / Eatonville
- County: Seminole
- Development Name: 32751 - Maitland / Eatonville
- Subdivision: DRUID HILLS ESTATES 1ST ADDITION
- Driving Directions: From downtown Orlando: take I-4 East, exit 90 A-B for FL-414E/Maitland Blvd. Take the exit toward Sandspur Rd. Continue onto Hope Rd. Turn right onto Sandspur Rd.Turn right onto Wymore Rd. Turn right onto Oranole Rd. Turn right onto Kathy Lane. Turn left onto Gregory Dr. House is on the right.
- Direction Faces: West
School Information
- Elementary School: Lake Orienta Elementary
- Middle School: Milwee Middle
- High School: Lyman High
Community
- Community Name: 32751 - Maitland / Eatonville
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Septic Tank
- Water: Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Available, Sprinkler Meter, Water Available
Structural Information
- Architectural Info: Mid-Century Modern
- Architectural Style: Mid-Century Modern
- Exterior Const.: Concrete
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 2,289
- Sq. Ft. Source: Builder
- Living Area: 2,289 Sq. Ft.
- Year Built: 1963
Additional Structures
- Other Structures: Shed(s), Storage
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 0.28
- Lot Size (Sq. Ft.): 12,196
- Lot Size: 12196
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt
- Fencing (Description): Wood
Financial Considerations
- Tax Amount: $4,982
- Tax Year: 2023
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 4 BLK B DRUID HILLS ESTATES 1ST ADD PB 11 PG 42
- Flood Zone Info: X
- APN: 2421295070B000040
- Property ID: 2421295070B000040
- Block/Lot/Section: B/NA
Listed by Florida Homes Realty & Mtg
Sold by Keller Williams Winter Park
Get Pre-Approved Today
Schools
Schools serving 1030 Gregory Dr
School District:Seminole County School District
| Name | Grades | Distance |
|---|---|---|
Lake Orienta Elementary School 612 Newport Avenue, Altamonte Springs, FL 32701 | K-5 | 0.6 mi |
Lyman High School 865 South Ronald Reagan Boulevard, Longwood, FL 32750 | 9-12 | 3.6 mi |
Milwee Middle School 1341 S Ronald Reagan Blvd, Longwood, FL 32750 | 6-8 | 3.2 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1030 Gregory Dr
Date
Details
Price
Change
Source
7/24/2025
Sold
$525,000
-5.23%
MLS
6/06/2025
Price Reduced
$554,000
-1.07%
MLS
5/11/2025
Price Reduced
$560,000
-1.75%
MLS
4/28/2025
Price Reduced
$570,000
-1.72%
MLS
4/14/2025
Price Reduced
$580,000
-0.85%
MLS
3/27/2025
Price Reduced
$585,000
-2.3%
MLS
3/23/2025
Price Reduced
$598,800
-0.17%
MLS
2/26/2025
Price Reduced
$599,800
-4.03%
MLS
9/02/2024
Price Reduced
$625,000
-3.1%
MLS
8/15/2024
Price Reduced
$645,000
-4.48%
MLS
7/17/2024
Price Reduced
$675,225
-2.85%
MLS
7/10/2024
Price Reduced
$695,000
-3.34%
MLS
7/05/2024
Price Reduced
$719,000
-3.74%
MLS
6/14/2024
Price Reduced
$746,930
-11.81%
MLS
6/11/2024
Listed
$846,930
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
1030 Gregory Drive, Maitland, FL 32751 (MLS# O6208703) is a Single Family property that was sold at $525,000 on July 24, 2025. Want to learn more about 1030 Gregory Drive? Do you have questions about finding other Single Family real estate for sale in Maitland? You can browse all Maitland real estate or contact a Coldwell Banker agent to request more information.

