1065 Gregory Dr Maitland, FL 32751
Estimated payment $3,272/month
Highlights
- Very Popular Property
- Screened Pool
- Wood Flooring
- Lyman High School Rated A-
- Ranch Style House
- Bonus Room
About This Home
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 Agent
EXP REALTY LLC Brokerage Phone: 888-883-8509 License #3364135 Listed on: 05/28/2026
Open House Schedule
-
Sunday, June 28, 202611:00 am to 1:00 pm6/28/2026 11:00:00 AM +00:006/28/2026 1:00:00 PM +00:00Hosted by agent Tazneem Chinquee.Add to Calendar
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $5,684
Year Built
- Built in 1958
Lot Details
- 12,371 Sq Ft Lot
- East Facing Home
- Vinyl Fence
- Mature Landscaping
- Irrigation Equipment
- Property is zoned R-1AA
Parking
- 2 Car Attached Garage
- Driveway
Home Design
- Ranch Style House
- Florida Architecture
- Shingle Roof
- Block Exterior
- Stucco
Interior Spaces
- 1,929 Sq Ft Home
- Ceiling Fan
- Wood Burning Fireplace
- Blinds
- French Doors
- Family Room Off Kitchen
- Living Room with Fireplace
- Dining Room
- Bonus Room
- Crawl Space
- Security System Owned
Kitchen
- Range
- Microwave
- Dishwasher
Flooring
- Wood
- Concrete
- Tile
Bedrooms and Bathrooms
- 3 Bedrooms
- Split Bedroom Floorplan
- 2 Full Bathrooms
- Single Vanity
- Bathtub with Shower
- Shower Only
Laundry
- Laundry Room
- Laundry in Garage
- Dryer
- Washer
Pool
- Screened Pool
- In Ground Pool
- Fence Around Pool
Outdoor Features
- Enclosed Patio or Porch
- Shed
Schools
- Lake Orienta Elementary School
- Milwee Middle School
- Lyman High School
Utilities
- Central Heating and Cooling System
- Thermostat
- 1 Septic Tank
Community Details
- No Home Owners Association
- Druid Hills Estates 1St Add Subdivision
Listing and Financial Details
- Visit Down Payment Resource Website
- Legal Lot and Block 12 / A
- Assessor Parcel Number 24-21-29-507-0A00-0120
Map
Home Values in the Area
Average Home Value in this Area
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $6,068 | $416,920 | $95,000 | $321,920 |
| 2024 | $5,765 | $410,724 | $95,000 | $315,724 |
| 2023 | $5,390 | $379,470 | $90,000 | $289,470 |
| 2021 | $3,162 | $248,722 | $0 | $0 |
| 2020 | $3,135 | $245,288 | $0 | $0 |
| 2019 | $3,104 | $239,773 | $0 | $0 |
| 2018 | $1,480 | $124,198 | $0 | $0 |
| 2017 | $1,465 | $121,643 | $0 | $0 |
| 2016 | $2,505 | $152,104 | $0 | $0 |
| 2015 | $1,422 | $129,898 | $0 | $0 |
| 2014 | $1,422 | $128,867 | $0 | $0 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 06/22/2026 06/22/26 | For Sale | $519,000 | 0.0% | $269 / Sq Ft | |
| 06/11/2026 06/11/26 | Pending | -- | -- | -- | |
| 05/28/2026 05/28/26 | For Sale | $519,000 | +16.6% | $269 / Sq Ft | |
| 11/10/2021 11/10/21 | Sold | $445,000 | +4.7% | $231 / Sq Ft | View Prior Sale |
| 09/27/2021 09/27/21 | Pending | -- | -- | -- | |
| 09/24/2021 09/24/21 | For Sale | $425,000 | +49.1% | $220 / Sq Ft | |
| 03/16/2018 03/16/18 | Sold | $285,000 | 0.0% | $148 / Sq Ft | View Prior Sale |
| 02/09/2018 02/09/18 | Pending | -- | -- | -- | |
| 02/08/2018 02/08/18 | For Sale | $285,000 | -- | $148 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $445,000 | Attorney | |
| Interfamily Deed Transfer | -- | Attorney | |
| Warranty Deed | $285,000 | Innovative Title Svcs Llc | |
| Warranty Deed | $262,500 | None Available | |
| Warranty Deed | $139,800 | -- | |
| Warranty Deed | $95,000 | -- | |
| Warranty Deed | $100,000 | -- | |
| Warranty Deed | $100 | -- | |
| Warranty Deed | $100 | -- |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $375,000 | New Conventional | |
| Previous Owner | $255,075 | New Conventional | |
| Previous Owner | $236,250 | New Conventional | |
| Previous Owner | $35,000 | Credit Line Revolving | |
| Previous Owner | $125,800 | New Conventional | |
| Previous Owner | $83,000 | New Conventional |
Source: Stellar MLS
MLS Number: O6411336
APN: 24-21-29-507-0A00-0120
- 1010 Gregory Dr
- 370 Sultana Ln
- 448 Stonewood Ln
- 9001 Lake Charity Dr
- 407 Hermitage Dr
- 457 Forestwood Ln
- 309 Monticello Dr
- 415 Hermitage Dr
- 1501 Druid Isle Rd
- 987 Brightwater Cir
- 423 Oak Hill Dr
- 504 Tivoli Ct
- 601 Oranole Rd
- 1911 Belford Ct
- 404 Barclay Ave
- 377 W Lake Faith Dr Unit 104
- 310 Cherokee Ct Unit F
- 310 Cherokee Ct Unit D
- 725 Northlake Blvd Unit 38
- 894 Jonathan Way Unit 3B
- 601 Trelago Way
- 361 W Lake Faith Dr Unit 112
- 510 Oak Ln
- 725 Northlake Blvd Unit 67
- 946 Lake Destiny Rd Unit E
- 948 Lake Destiny Rd Unit E
- 948 Lake Destiny Rd
- 948 Lake Destiny Rd Unit H
- 948 Lake Destiny Rd Unit C
- 944 N Lake Destiny Rd Unit F
- 944 Lake Destiny Rd Unit E
- 230 Countrywalk Place
- 219 Debora Ct
- 940 Lake Destiny Rd Unit H
- 900 Lake Destiny Rd Unit B
- 902 Lake Destiny Rd Unit C
- 895 Wymore Rd
- 922 Lake Destiny Rd Unit F
- 922 Lake Destiny Rd Unit C
- 922 N Lake Destiny Rd
Ask me questions while you tour the home.