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$370,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,382 Sq. Ft.
  • Updated 3 hours ago
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Cute home alert! Finally - an updated, move-in ready home in an amazing Maitland location priced under $400K! Imagine hosting friends and family in the spacious separate dining room, gathering around the oversized kitchen island while dinner cooks, and spending evenings relaxing on the screened patio and playing safely in the fully fenced backyard. Tucked inside the quiet Winfield community with a low HOA, this beautifully maintained 3-bedroom, 2-bath home with split floor plan is an excellent balance of modern style and everyday functionality. Step inside to discover a bright, open-concept layout featuring vaulted ceilings, recessed lighting, and consistent hard-surface flooring throughout. The spacious living area flows seamlessly into the fully updated gourmet kitchen, complete with beautiful countertops, 42" solid wood soft-close cabinetry, and high-end stainless steel appliances - creating a welcoming space in the heart of your home. This split floor plan offers both privacy and flexibility, with an expansive primary suite featuring a walk-in closet with custom built-ins and a beautifully updated bathroom with dual vanities, a relaxing garden tub, and separate shower. On the opposite side of the home, two additional bedrooms are ideal for a nursery, guest room, playroom, or home office. The living space flows to a covered and screened patio, creating a perfect space for year-round indoor-outdoor living. Whether you're enjoying slow mornings with coffee, hosting weekend get-togethers, or relaxing after work, the fully fenced backyard offers both comfort and privacy. Fresh landscaping, mature shade trees, and the perfect mix of filtered sunlight and greenery give the outdoor space a calm, inviting feel, while the tiled flooring adds a clean, polished touch that's both stylish and low maintenance. ROOF: 2018

Full Property Details for 2040 Bobtail Dr

General

  • Price: $370,000
  • HOA FEE: $18/month
  • HOA FEE FREQ.: Semi-Annually
  • Taxes: $3,096 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6408698
  • Updated: Today (5/19/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 10
  • Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen and Family Room Combination, Open Floorplan, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
  • Appliances: Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Freezer, Ice Maker, Microwave, Refrigerator, Touchless Faucet, Washer, Water Filtration System
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Exterior

  • Exterior Features: Lighting, Rain Gutters, Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Enclosed, Front Porch, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Enclosed, Front Porch, Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway

Location

  • Area: 32751 - Maitland / Eatonville
  • County: Orange
  • Development Name: 32751 - Maitland / Eatonville
  • Subdivision: WINFIELD UT 1
  • Driving Directions: From I-4 take West Maitland Blvd (414) West, Left on Maitland Summit Blvd, Left on Bobtail Drive. House on Left.
  • Direction Faces: North

School Information

  • Elementary School: Lake Sybelia Elem
  • Middle School: Lockhart Middle
  • High School: Edgewater High

Community

  • Community Name: 32751 - Maitland / Eatonville
  • Association: Yes
  • Assoc. Name: Winfield Homeowners Association

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Street Lights, Underground Utilities, Water Connected

Structural Information

  • Architectural Info: Florida
  • Architectural Style: Florida
  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,382
  • Sq. Ft. Source: Public Records
  • Year Built: 1998

Lot Features

  • Lot Size (Acres): 0.12
  • Lot Size (Sq. Ft.): 5,167
  • Lot Size: 5167
  • Frontage: Private Road
  • Street/Road Desc.: Paved
  • Fencing (Description): Masonry, Wood

Financial Considerations

  • Association Fee: $105
  • Assoc Fee Freq.: Semi-Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $3,096.55
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINFIELD UNIT 1 34/77 LOT 31
  • Flood Zone Info: X
  • APN: 272129946900310
  • Property ID: 272129946900310
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 2040 Bobtail Dr —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 2040 Bobtail Dr

School District:Orange County School District
NameGradesDistance
Lake Sybelia Elementary School
600 Sandspur Road, Maitland, FL 32751
K-52 mi
Lockhart Middle School
3411 Doctor Love Rd, Orlando, FL 32810
6-81.2 mi
Edgewater High School
3100 Edgewater Drive, Orlando, FL 32804
9-123.4 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 2040 Bobtail Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/19/2026
Listed
$370,000
45.1%
MLS
6/27/2019
Sold
$255,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2040 Bobtail Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,097
3%
$236,679
6%
2024
$3,002
5%
$223,962
3%
2023
$2,870
9%
$217,439
6%
2021
$2,644
-1%
$204,957
-3%
2022
$2,684
2%
$211,106
2%
2021
$2,644
90%
$206,264
67%
2019
$1,389
1%
$123,846
2%
2018
$1,374
2%
$121,537
2%
2017
$1,350
1%
$119,037
2%
2016
$1,331
-2%
$116,589
1%
2015
$1,356
-1%
$115,779
1%
2014
$1,364
4%
$114,860
1%
2013
$1,313
—
$113,163
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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2040 Bobtail Drive, Maitland, FL 32751 (MLS# O6408698) is a Single Family property with 3 bedrooms and 2 full bathrooms. 2040 Bobtail Drive is currently listed for $370,000 and was received on May 19, 2026. This property is listed by Michael Wathen from our Winter Springs / Oviedo Office.Want to learn more about 2040 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.

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