
1776 BOBTAIL DRIVE, MAITLAND, FL 32751
WINFIELD · Orange County
Key Facts
Description
Welcome to 1776 Bobtail Drive — the kind of home that doesn’t just check boxes… it creates emotion, urgency, and that unmistakable “we need this one” reaction the moment your buyers walk through the door. From the very first glance, the curb appeal sets the stage with a warm, polished presence that immediately stands out from the competition. Inside, you’re welcomed by a light-filled, open-concept layout that feels expansive yet comfortable — the perfect balance of elegance and livability. Every space has been thoughtfully designed to flow effortlessly, creating an atmosphere that feels both elevated and inviting. The heart of the home is a beautifully positioned kitchen that seamlessly connects to the main living areas, making it ideal for entertaining, gathering, and everyday life. Whether hosting friends or enjoying a quiet night in, this home delivers the versatility today’s buyers demand. Generously sized living spaces and bedrooms provide comfort, privacy, and flexibility, while the overall layout offers a sense of ease and functionality that appeals to a broad range of buyers — from families to professionals to those simply looking to upgrade their lifestyle. Step outside and experience your own private Florida escape — a backyard setting that invites relaxation, weekend gatherings, and year-round enjoyment. It’s the kind of outdoor space that sells the lifestyle just as much as the home itself. Perfectly positioned in a highly desirable Maitland location, this property offers unbeatable convenience to top-rated dining, shopping, entertainment, and major highways — putting everything Central Florida has to offer right at your fingertips. This is not just another listing — it’s a high-impact, high-demand opportunity that shows beautifully, lives effortlessly, and is primed to sell quickly. Homes with this combination of appeal, location, and lifestyle don’t sit… they move. Bring your buyers with confidence — this is the one they’ve been waiting for.
Property Information
Property Type
Residential
Sub-Type
Single Family Residence
Style
Contemporary
Year Built
1998
Stories
2
Living Area
2,954 sq ft
Lot Size
0.12 acres
Garage Spaces
2
Ownership
Fee Simple
Zoning
RSF-3
Days on Market
48
MLS® Listing#
G5110747
Property Features
Interior
Exterior
Appliances
Cooling
Heating
Flooring
Parking
Laundry
Patio
Fencing
Lot Features
Construction
Foundation
Roof
Windows
Security
Community
Utilities
Sewer
Water Source
Rooms
- Bedroom 210x12Second
- Bedroom 310x13.8Second
- Bedroom 412.8x10.2First
- Dining Room14.11x6.8First
- Family Room16x18First
- Kitchen11.9x15.1First
- Living Room14.11x16.8First
- Master Bathroom9x12.6Second
- Master Bedroom21.8x15.5Second
Schools
- Elementary:
- Lake Sybelia Elem
- Middle:
- Lockhart Middle
- High:
- Edgewater High
Financial Details
HOA
$102 / Semi-Annually
Specialty Mgmt/Cathy Wasson
Annual Taxes
$2,578
Tax year 2025
Parcel Number
27-21-29-9356-01-140
Directions
Driving Directions: Take I-4 to the Maitland Blvd (SR-414) exit. Head west on Maitland Blvd. Turn left onto Maitland Summit Blvd (Wendy’s on the corner). Continue straight to the end of the road into the Winfield community. Turn right onto Bobtail Drive. Follow Bobtail — 1776 Bobtail Drive will be on your left.
Affordability Calculator
$104,000
Estimated monthly payment
$2,768/mo
Principal $415,999 · Est. interest $580,356 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in MAITLAND, FL
- $508,696
- Median Listing Price
- 77
- Median Days on Market
- 1,842
- Median Sq Ft
- $273
- Median Price / Sq Ft
- 99
- Active Listings
- This home’s price is 2% above the area median.
- Its price per sq ft is 36% below the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in MAITLAND, FL.
Location
Map is currently unavailable for this location.
Points of Interest in MAITLAND, FL
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Commute Calculator
Nearby Homes
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Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 110 N LAKEWOOD CIRCLE, MAITLAND, FL | $375,000 | 3 | 2 | 1,341 |
| 1994 KENASTON ROAD 1994, MAITLAND, FL | $399,000 | 3 | 4 | 2,103 |
| 2340 DERBYSHIRE ROAD, MAITLAND, FL | $399,000 | 3 | 2 | 1,798 |
| 2150 TORTOISE SHELL DRIVE, MAITLAND, FL | $399,900 | 4 | 2 | 1,512 |
| 1010 WINDERLEY PLACE 149, MAITLAND, FL | $429,900 | 3 | 2 | 1,651 |
| 2180 TORTOISE SHELL DRIVE, MAITLAND, FL | $435,000 | 3 | 2 | 1,622 |
Moving Cost Estimate
Listing Courtesy: THE FLORIDA PROPERTY SHOP SALE - 352-346-7857
Last Updated: 2026-04-06








