Date
Details
Price
Change
Source
8/14/2026
Listed
$349,999
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$349,999 Just Listed
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Property Description
Beautiful Winfield Community home in Maitland Florida will not last long. This 3 bedroom/2 bath home has so much to offer. The property recently has had a new roof put on this year in 2026, new AC unit this year in 2026, and freshly painted in 2026. The kitchen features an eat in bar top as well as a large island for plenty of use-able countertop space. The back yard is fully fenced in for privacy. The home comes with a stove, refrigerator, microwave, washer, and dryer. The garage is oversized for 2 cars with extra space for storage. The flooring is ceramic in the main living areas for easy cleaning when needed. Low HOA dues for an upscale community. Dont miss out on this home.
Full Property Details
Full Property Details for 1866 Bobtail Dr
General
- Price: $349,999
- HOA FEE: $18/month
- HOA FEE FREQ.: Semi-Annually
- Taxes: $4,480 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6432604
- Updated: 8/14/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 1-2 Years
Interior
- Number of Rooms: 3
- Interior Features: Ceiling Fan(s), Open Floorplan, Thermostat
- Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Common Area
Exterior
- Exterior Features: Sidewalk
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 32751 - Maitland / Eatonville
- County: Orange
- Development Name: 32751 - Maitland / Eatonville
- Subdivision: WINFIELD
- Driving Directions: From SR 434 turn right onto Falkner Road. Turn left on Bobtail Drive and home will be on the left.
- Direction Faces: West
Community
- Community Name: 32751 - Maitland / Eatonville
- Community Features: Sidewalks
- Association: Yes
- Assoc. Name: Cathy Wesson
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Public
Structural Information
- Exterior Const.: Block
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 1,322
- Sq. Ft. Source: Public Records
- Year Built: 1996
Lot Features
- Lot Size (Acres): 0.12
- Lot Size (Sq. Ft.): 5,259
- Lot Size: 5259
- Street/Road Desc.: Asphalt
Financial Considerations
- Association Fee: $105
- Assoc Fee Freq.: Semi-Annually
- Assoc Fee Desc.: Required
- Tax Amount: $4,480
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WINFIELD UNIT 1 34/77 LOT 12
- Flood Zone Info: X
- APN: 272129946900120
- Property ID: 272129946900120
Listed by 407 Properties
We Value Your Privacy
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Listing agent
— 1866 Bobtail Dr —
407 Properties
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 1866 Bobtail Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Lake Sybelia Elementary School 600 Sandspur Road, Maitland, FL 32751 | K-5 | 1.9 mi |
Lockhart Middle School 3411 Doctor Love Rd, Orlando, FL 32810 | 6-8 | 1.3 mi |
Edgewater High School 3100 Edgewater Drive, Orlando, FL 32804 | 9-12 | 3.5 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 1866 Bobtail Dr
Tax History
Tax History for 1866 Bobtail Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,480
—
$274,520
-1%
2025
$4,480
7%
$278,460
4%
2024
$4,171
6%
$267,603
-1%
2023
$3,939
33%
$271,278
46%
2021
$2,971
-12%
$185,997
-19%
2022
$3,374
14%
$230,979
23%
2021
$2,971
5%
$187,184
7%
2019
$2,843
8%
$174,717
9%
2018
$2,638
10%
$160,870
13%
2017
$2,398
1%
$142,296
2%
2016
$2,369
2%
$138,942
8%
2015
$2,332
9%
$128,499
10%
2014
$2,132
15%
$116,817
10%
2013
$1,857
—
$106,197
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 1866 Bobtail Dr
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Sold by Exp Realty Llc
Sold by Exp Realty Llc
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Sold by Thomas Liles
Sold by Thomas Liles
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Sold by Fannie Hillman & Associates
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- 4Beds
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Listed by Lpt Realty, Llc
Sold by Lpt Realty, Llc
Sold by Lpt Realty, Llc
1866 Bobtail Drive, Maitland, FL 32751 (MLS# O6432604) is a Single Family property with 3 bedrooms and 2 full bathrooms. 1866 Bobtail Drive is currently listed for $349,999 and was received on August 14, 2026. Want to learn more about 1866 Bobtail 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.