Under contract-accepting backup offers. 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.
Property Details
Price:
$349,999
MLS #:
O6432604
Status:
Active Under Contract
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINFIELD
Neighborhood:
32751maitlandeatonville
Listed Date:
Aug 14, 2026
Finished Sq Ft:
1,322
Total Sq Ft:
1,791
Lot Size:
5,259 sqft / 0.12 acres (approx)
Year Built:
1996
See this Listing
Schools
Interior
Appliances
Dishwasher, Dryer, Microwave, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Ceramic Tile
Heating
Central
Interior Features
Ceiling Fan(s), Open Floorplan, Thermostat
Laundry Features
Common Area
Levels
One
Exterior
Attached Garage YN
1
Community Features
Sidewalks
Construction Materials
Block
Covered Spaces
2
Direction Faces
West
Exterior Features
Sidewalk
Garage Spaces
2
Roof
Shingle
Financial
HOA Fee
$105
HOA Fee Frequency
Semi-Annually
HOA Name
Cathy Wesson
HOA Phone
4076472622
Tax Year
2025
Taxes
$4,480
Map
Community
- Address1866 BOBTAIL DRIVE MAITLAND FL
- SubdivisionWINFIELD
- CityMAITLAND
- CountyOrange
- Zip Code32751
Subdivisions in MAITLAND
- ACREAGE
- BRITTANY GARDENS
- CARRINGTON PARK A CONDO
- CHERRYWOOD GARDENS
- CLARK HOMES ACRES
- COFFINS
- COOPERS SUB
- DIXIE TERRACE
- DOMMERICH ESTATES 1ST ADD
- DOMMERICH ESTATES 1ST ADD MAITLAND
- DOMMERICH ESTATES 2ND ADD
- DOMMERICH HILLS
- DOMMERICH HILLS 2 ND ADD
- DOMMERICH HILLS 6TH ADD
- DOMMERICH HILLS SECOND ADD
- DOMMERICH WOODS
- DOMMERICH/MAITLAND HIGHLANDS
- DRUID HILLS ESTATES 1ST ADD
- DRUID HILLS ESTS
- DRUID HILLS PARK
- DRUID ISLE
- EATON ESTATES
- EATONVILLE LAWRENCE
- ENCLAVE AT MAITLAND A-F
- ENCLAVE/MAITLAND A-F
- ENGLISH ESTATES UNIT 2
- ENGLISH ESTATES UNIT 3
- ENGLISH WOODS
- FLORIDAHAVEN
- FORD & WARREN SUB
- FOREST BROOK
- FOREST BROOK 2ND SEC
- FOREST BROOK 3RD SEC
- FOREST BROOK 5TH SEC
- FOREST BROOK SEC 2-A
- HAMLET AT MAITLAND
- HIDDEN ESTATES UNIT 3
- HIGHLAND PARK ESTATES FIRST ADD
- HIGHLAND PARK ESTS
- HOLLIEANNA SHORES
- HOLLIEANNA SHORES 1ST ADD
- INDIAN HILLS UNIT 9
- KINGS ROW
- LAKE COLONY PH 02
- LAKE FAITH VILLAS CONDO
- LAKE MAITLAND MANOR
- LAKE MAITLAND PARK
- LAKE MAITLAND TERRACE APTS
- LAKE SYBELIA COVE
- LAKE SYBELIA COVE PH 01
- LAKE SYBELIA SHORES
- LAKE SYBELIA SHORES FIRST ADD
- LAKEWOOD SHORES
- MAITLAND CLUB REP
- MAITLAND COVE
- MAITLAND GROVE
- MAITLAND HIGHLANDS
- MAITLAND PARK SOUTH
- MAITLAND WOODS THIRD ADD
- MINNEHAHA SHORES
- MOORINGS ON LAKE MAITLAND CONDO
- MOORINGS ON LAKE MAITLAND CONDO BLDG 05
- NORTHGATE
- NORTHWOOD HEIGHTS
- OAKLAND SHORES
- OAKLAND SHORES 3RD ADD REP
- OAKLEIGH THIRD ADD
- OAKWOOD
- OSBORNE MANOR
- PARK LAKE GROVE CONDO
- PARK LAKE GROVE CONDO PH C
- PARK LAKE TWNHS
- PARK LAKE VILLAS CONDO
- REPLAT BLK B POORS ADD
- ROOSEVELT PLACE
- SERENDIPITY PARK
- SHERIDAN PLACE
- STONEWOOD FIRST ADD
- SUN BAY CLUB CONDO
- SUN BAY CLUB CONDO UT 1
- SUNSET RIDGE
- SYBELIA PLACE
- ULTRA VISTA CONDO
- VILLAS LAKE DESTINY
- VISCONTI EAST
- VISCONTI EAST BLDG 27
- VISCONTI WEST
- VISCONTI WEST CONDO
- WELLINGTON
- WEST COVE
- WEST COVE CONDO
- WINFIELD
- WOODBRIDGE
Market Summary
Current real estate data for Single Family in MAITLAND as of Sep 19, 2026
84
Single Family Listed
93
Avg DOM
319
Avg $ / SqFt
$857,925
Avg List Price
Property Summary
- Located in the WINFIELD subdivision, 1866 BOBTAIL DRIVE MAITLAND FL is a Single Family for sale in MAITLAND, FL, 32751. It is listed for $349,999 and features 3 beds, 2 baths, and has approximately 1,322 square feet of living space, and was originally constructed in 1996. The current price per square foot is $265. The average price per square foot for Single Family listings in MAITLAND is $319. The average listing price for Single Family in MAITLAND is $857,925. To schedule a showing of MLS#o6432604 at 1866 BOBTAIL DRIVE in MAITLAND, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of 407 PROPERTIES. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 1866 BOBTAIL DRIVE
MAITLAND, FL