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 & UNREC
- ADAMS GROVE
- BEG 635 FT E & 430 FT N OF SW COR OF SW1/4 OF NE1/
- BRANCH TREE
- BRITTANY GARDENS
- BUCHER HGTS
- CALHOUNS SUB
- CARRINGTON PARK A CONDO
- CHERRYWOOD GARDENS
- COFFINS SUB
- COOL-MORE SUB
- COOPERS SUB
- DIXIE TERRACE
- DOMMERICH
- DOMMERICH ESTATES 1ST ADD
- DOMMERICH ESTATES 2ND ADD
- DOMMERICH HILLS
- DOMMERICH HILLS 2ND ADD
- DOMMERICH HILLS 3RD ADD
- DOMMERICH HILLS FIFTH ADD
- DOMMERICH HILLS SECOND ADD
- DOMMERICH WOODS
- DOMMERICH WOODS UNIT 1
- DOMMERICH/COVE COLONY
- DRUID HILLS
- DRUID HILLS PARK
- EATON ESTATES
- EATONVILLE
- ENCLAVE/MAITLAND A-F
- ENGLISH ESTATES UNIT 1
- ENGLISH ESTATES UNIT 2
- ENGLISH ESTATES UNIT 3
- ENGLISH ESTS UNIT 1
- ENGLISH WOODS
- FIRST ADD TO CALHOUNS SUB
- FOREST BROOK
- FOREST BROOK 3RD SEC
- FOREST BROOK 5TH SEC
- GREENWOOD GARDENS SEC 01
- GREENWOOD GARDENS SEC 02 REP 01
- HAMLET AT MAITLAND
- HIGHLAND PARK ESTATES FIRST ADD
- HOLDEN BROS SUB
- HOLLIEANNA SHORES
- HOLLIEANNA SHORES 1ST ADD
- INDIAN HILLS UNIT 1 REP
- INDIAN HILLS UNIT 9
- KINGS ROW
- LAKE COLONY PH 01 REP
- LAKE EULALIA HEIGHTS
- LAKE FAITH VILLAS CONDO
- LAKE MAITLAND MANOR
- LAKE MAITLAND OWL PRESERVE
- LAKE MAITLAND TERRACE APTS
- LAKE SYBELIA COVE
- LAKEWOOD SHORES 1ST ADD
- MADDON COVE 47/24
- MAITLAND EXCHANGE
- MAITLAND GROVE
- MAITLAND HARBOUR APTS
- MAITLAND ISLE
- MAITLAND VILLAGE
- MAITLAND WOODS
- MOORINGS ON LAKE MAITLAND CONDO
- MOORINGS ON LAKE MAITLAND CONDO BLDG 05
- NORTHGATE
- NORTHWOOD HEIGHTS
- OAKLAND SHORES
- OAKLAND SHORES 1ST ADD
- OAKLAND SHORES 3RD ADD REP
- OAKLEIGH 3RD ADD
- OAKWOOD
- ORANGEDALE PARK
- PACKWOODS PLAN/MAITLAND
- PARK LAKE GROVE CONDO PH B
- PARK LAKE SHORES
- PARK LAKE TOWNHOUSES
- PARK LAKE TWNHS
- PARK LAKE TWNHS PH 02
- PARK LAKE VILLAS CONDO
- PARK LAKE VILLAS CONDO CB 2/52
- PARK LAKE WOODS CONDO
- PRESERVE AT MAITLAND
- REPLAT BLK B POORS ADD
- RIDGEWOOD VILLAS CONDO
- ROOSEVELT PLACE
- SCHOOLVIEW ADD
- SHOPPES/MAITLAND
- SIERRA CONDOMINIUMS
- STONEWOOD
- SUN BAY CLUB CONDO
- THOMPSON SUB
- ULTRA VISTA CONDO
- VERSAILLES
- VISCONTI EAST
- VISCONTI EST
- VISCONTI WEST
- VISCONTI WEST BLDG 3
- VISCONTI WEST BLDG 5
- VISCONTI WEST CONDO
- WELLINGTON
- WEST COVE
- WINFIELD
- WOODBRIDGE
Market Summary
Current real estate data for Single Family in MAITLAND as of Aug 29, 2026
89
Single Family Listed
94
Avg DOM
334
Avg $ / SqFt
$986,686
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 $334. The average listing price for Single Family in MAITLAND is $986,686. To schedule a showing of MLS#o6432604 at 1866 BOBTAIL DRIVE in MAITLAND, FL, contact your CENTURY 21 Carioti agent at 2392986550.
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