Set within one of Winter Garden’s most sought-after communities, this thoughtfully designed two-story home offers a lifestyle defined by ease, connection, and everyday enjoyment. This 4-bedroom, 3.5-bath home with over 3,000 square feet features an open floor plan with a gourmet kitchen and a large island, perfect for both everyday living and entertaining. The main level includes a dedicated den/office, while the second floor offers a spacious loft, along with a fourth bedroom and full bath—ideal for guests or multi-generational living. Tree-lined sidewalks, friendly neighbors, nearby parks, and resort-style amenities create a setting that feels both relaxed and vibrant, while top-rated schools, convenient access to shopping and dining, and close proximity to Walt Disney World Resort. Positioned on arguably one of the BEST lots in the community, this home sits at the end of a quiet cul-de-sac with breathtaking, unobstructed pond and tree-lined views that create a peaceful and private backdrop. Inside, the home showcases extensive upgrades and thoughtful design throughout, including a kitchen with 42-inch cabinetry and additional custom upper cabinets, GE Profile appliances, and a seamless flow into the main living space highlighted by two expansive tri-sliders opening to the outdoor oasis. Custom floor-to-ceiling drapery adds elegance, while upgrades such as 8-foot doors throughout, level 4 wood-look tile flooring, upgraded carpet with 8-pound padding, 5 1/4-inch baseboards, and 7 1/4-inch shiplap accents in the hallway, kitchen, tech nook, and primary bedroom elevate the interior. Additional features include custom plantation shutters on the first floor, upgraded glass doors in the front den/office, Cat 6 wiring throughout with pre-wiring for PoE security cameras, and a new alarm system with wireless sensors on all doors and windows. The home has been meticulously maintained with quarterly HVAC servicing, gutters installed since purchase, and a freshly painted exterior completed in 2025 using upgraded Sherwin Williams 25-year paint. Step outside to a private outdoor retreat featuring fresh landscaping, a fully fenced side yard, a privacy-enhancing podocarpus hedge, and custom paver walkways with additional space for storage. The backyard feels like a private Central Florida escape, where an 18,000-gallon resort-style saltwater pool serves as the true centerpiece, complete with a lounging platform overlooking the serene pond and tree-lined backdrop. The pool is thoughtfully designed with sealed pavers, a striking midnight blue interior finish, a fountain with dual deck jets, two multicolor LED lights, and a Pentair smart system for remote control, all professionally serviced weekly. The screened enclosure allows for year-round enjoyment, while the community dog park directly across the street adds everyday convenience for pet lovers. From the upstairs loft and bedrooms, enjoy views of Disney fireworks, adding a magical touch to everyday living. This move-in ready home is prepared for its next chapter, with community amenities that include a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and a dog park. More than just beautifully upgraded, this home offers a rare opportunity to own a meticulously maintained, design-forward property in a premier location, delivering both luxury and lifestyle in one exceptional package—a place to settle in, build memories, and truly feel at home in Winter Garden.
Property Details
Price:
$925,000
MLS #:
O6399653
Status:
Pending
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDING BAY PH 1B
Neighborhood:
34787wintergardenoakland
Listed Date:
Apr 17, 2026
Finished Sq Ft:
3,127
Total Sq Ft:
4,208
Lot Size:
6,912 sqft / 0.16 acres (approx)
Year Built:
2020
See this Listing
Schools
Elementary School:
Water Spring Elementary
Middle School:
Water Spring Middle
High School:
Horizon High School
Interior
Appliances
Built-In Oven, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, Refrigerator
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile
Heating
Central
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Walk-In Closet(s), Window Treatments
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Levels
Two
Exterior
Architectural Style
Florida
Association Amenities
Pool
Attached Garage YN
1
Community Features
Association Recreation – Owned, Community Mailbox, Deed Restrictions, Dog Park, Park, Playground, Pool
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
North
Exterior Features
Irrigation System, Outdoor Grill, Rain Gutters, Sidewalk, Sliding Doors, Sprinkler Metered
Fencing
Fenced
Garage Spaces
2
Lot Features
Cul-De-Sac, Sidewalk, Street Dead-End
Patio And Porch Features
Front Porch, Rear Porch, Screened
Roof
Shingle
Security Features
Security System, Security System Owned, Smoke Detector(s)
View
Water
Waterfront Features
Pond
Financial
HOA Fee
$102
HOA Fee Frequency
Monthly
HOA Includes
Community Pool, Pool Maintenance, Recreational Facilities
HOA Name
Mariluz Onna – FS Residential
HOA Phone
407-653-8134
Tax Year
2025
Taxes
$8,308
Map
Community
- Address15306 GILLIGAN COURT WINTER GARDEN FL
- SubdivisionWINDING BAY PH 1B
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
- .
- 30 NORTH PARK
- ACREAGE
- ACREAGE & UNREC
- ADDITION TO MARY JEAN SUB
- ALEXANDER RIDGE
- ANNIE L BERRY SUB
- ARROWHEAD LAKES
- AVALON ESTATES
- AVALON HILLS SUB
- AVALON RDG
- AVALON RESERVE VILLAGE 1
- AVALON RIDGE
- AVALON WOODS
- BAY ISLE 48 17
- BAY ST PARK
- BELLE MEADE PH 02 H
- BELLE MEADE PH 2
- BELLE MEADE-PH I B D & G
- BLACK LAKE
- BLACK LAKE PARK PH 01
- BLACK LAKE PARK PH 02 F-1
- BLACK LAKE PRESERVE
- BLACK LK PK PH 1
- BRADFORD CREEK-PH II
- BRADFORD CRK PH I
- BRADFORD CRK PH II
- BRANDY CREEK
- BRAY J W F ADD 01
- BRONSONS LNDGS F & M
- BURCHSHIRE
- BURCHSHIRE Q/138 LOT 8 BLK B
- CAMBRIDGE CROSSING PH 02 43/147
- CANOPY OAKS PH 1
- CANOPY OAKS PHASE 1
- CARRIAGE POINTE A-I & L
- CITRUS COVE UNIT 01
- COOPER & SEWELL ADD
- COUNTRY LAKES
- COURTLEA OAKS
- COURTLEA OAKS PH 01A
- COVINGTON CHASE
- COVINGTON CHASE PH 2A
- COVINGTON PARK A B D E F G & J
- CROWN POINT SPGS
- CYPRESS RESERVE PH 2
- DANIEL CROSSING
- DANIELS LANDING
- DANIELS LNDG A-J
- DEER ISLAND
- DEER ISLAND PH 02
- DEERFIELD PLACE A-G
- DEL WEBB OASIS
- DEL WEBB OASIS PH 3
- EAST GARDEN MANOR ADD 03 REP
- ELLMAN PARK
- EMERALD ACRES
- ENCLAVE AT HAMLIN
- ENCORE AT OVATION
- ENCORE AT OVATION – PHASE 4B 111/103 LOT 410
- ENCORE AT OVATION-PH 3
- ENCORE/OVATION PH 1
- ENCORE/OVATION PH 2
- ENCORE/OVATION PH 3
- ENCORE/OVATION PH 4B
- ENCORE/OVATION-PH 3
- ENCORE/OVATION-PH 4B
- ESTATES AT LAKEVIEW
- ESTATES AT LAKEVIEW PRESERVE
- ESTS/LAKEVIEW PRESERVE
- FOXCREST
- FRIES SURVEY OF WINTER GARDEN
- FRIES WINTER GARDEN
- FULLERS XING PH 03 A-G
- G T SMITH SUB
- G T SMITH SUB 3
- G T SMITH SUB 4
- GLENVIEW ESTATES
- GLENVIEW ESTATES 2ND ADD
- GREYSTONE PH 01
- GROVE PK/STONE CREST A-E
- GROVE RES & SPA HOTEL CONDO 3
- GROVE RES & SPA HOTEL CONDO IV
- GROVE RESIDENCE & SPA HOTEL
- GROVE RESIDENCE & SPA HOTEL CONDO
- GROVE RESIDENCE & SPA HOTEL CONDO 2
- GROVE RESIDENCE & SPA HOTEL CONDO 3
- GROVE RESIDENCE & SPA HOTEL CONDO I
- GROVE RESIDENCE & SPA HOTEL CONDO II
- GROVE RESIDENCE & SPA HOTEL CONDO IL
- GROVE RESIDENCE Y SPA HOTEL CONDO II
- GROVE RESORT
- GROVE RESORT & SPA
- GROVE RESORT & SPA HOTEL CONDO IV
- GROVE RESORT AND SPA
- GROVE RESORT AND SPA HOTEL
- GROVE RESORT AND SPA HOTEL CONDO 1
- GROVE RESORT AND SPA HOTEL CONDOMINIUM
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 1
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 2
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 3
- GROVE RESORT AND SPA HOTEL CONDOMINIUM U
- GROVE RESORT HOTEL AND SPA HOTEL CONDO 1
- GROVEHURST
- HAMILTON GARDENS
- HAMILTON GARDENS PH 2A & 2B
- HAMLIN POINTE
- HAMLIN RDG
- HAMLIN RESERVE
- HAMLIN RIDGE
- HARVEST AT OVATION
- HARVEST/OVATION
- HARVET AT OVATION
- HAWKSMOOR – PHASE 2
- HAWKSMOOR PH 1
- HAWKSMOOR PH 3
- HAWKSMOOR PH 4
- HAWKSMOOR-PH 1
- HAWKSMOOR-PH 3
- HERITAGE/PLANT STREET
- HICKORY HAMMOCK PH 1B
- HICKORY HAMMOCK PH 1D
- HICKORY HAMMOCK PH 2A
- HICKORY HAMMOCK PH 2B
- HIGHLAND RDG
- HIGHLAND RDG PH 2
- HIGHLAND RIDGE
- HIGHLAND RIDGE 110/69 LOT 19
- HIGHLANDS/SUMMERLAKE GROVE PH 2
- HIGHLANDS/SUMMERLAKE GRVS PH 1
- HIGHLANDS/SUMMERLAKE GRVS PH 2
- HIGHLANDS/SUMMERLAKE GRVS PH 3
- HILLCREST
- HORIZON ISLE
- ILVERLEAF OAKS AT HAMLIN
- INDEPENDENCE COMMUNITY
- ISLAND POINTE SUB
- ISLES/LK HANCOCK PH 3
- ISLES/LK HANCOCK PH III
- J L DILLARD SUB 3
- J S LOVELESS ADD
- JOE LOUIS PARK
- JOHNS LAKE POINTE
- JOHNS LAKE POINTE A & S
- K HOVNANIAN WINDING BAY PRESERVE
- LAKE APOPKA SOUND
- LAKE APOPKA SOUND PH 1
- LAKE AVALON GROVES
- LAKE AVALON GROVES 2ND REP
- LAKE AVALON GROVES REP
- LAKE AVALON GROVES REP 02
- LAKE AVALON GRVS 2ND REP
- LAKE AVALON HEIGHTS
- LAKE FOREST SEC 10A
- LAKE HANCOCK PRESERVE
- LAKE STAR AT OVATION
- LAKE VIEW ADD
- LAKESHORE PRESERVE PH 1
- LAKESHORE PRESERVE PH 2
- LAKESHORE PRESERVE PH 5
- LAKESHORE PRESERVE PH I
- LAKESIDE AT HAMLIN
- LAKEVIEW POINTE/HORIZON WEST
- LAKEVIEW POINTE/HORIZON WEST 1
- LAKEVIEW POINTE/HORIZON WEST P
- LAKEVIEW PRESERVE
- LAKEVIEW PRESERVE PH 2
- LAKEVIEW PRESERVE PHASE 2
- LAKEVIEW RESERVE 46/149
- LATHAM PARK
- LATHAM PARK NORTH
- LATHAM PARK SOUTH
- LATHAN PARK NORTH
- LOVELESS & SEWELL ADD
- LOVELESS J S ADD 01
- MANNS FIRST ADD
- MARY JEAN SUB
- MCALLISTER LNDG
- MCALLISTER LNDG PH 2
- MERCHANTS SUB
- MEZZANO
- MOUNTAIN PARK ORLANGE GROVES
- NORTHLAKE AT OVATION
- NORTHLAKE AT OVATION PHASE 1 109/122 LOT 37
- NORTHLAKE AT OVATION PHASE 2 & 3
- NORTHLAKE/OVATION PH 1
- OAKLAND PARK
- OAKLAND PARKB
- OAKLAND PARKB-1B A
- OAKLAND PK UN 7 SOUTH 112/136 LOT 175
- OAKLAND TRLS PH 1
- OAKS/BRANDY LAKE
- OAKS/BRANDY LAKE O
- ORANGE COVE
- ORCHARD A1-A26 B1 B2 C D1-D4
- ORCHARD HILLS
- ORCHARD HILLS PH 1
- ORCHARD HILLS PH 2
- ORCHARD HILLS PH 3
- ORCHARD HILLS PH 4
- ORCHARD HILLS PH I
- ORCHARD HILLS PHASE 3
- ORCHARD PK/STILLWATER XING PH
- OSPREY RANCH
- OSPREY RANCH PH 1
- OSPREY RANCH-PH 1
- OVERLOOK 2 AT HAMLIN PHASE 2 AND 5
- OVERLOOK 2/HAMLIN PH 1 & 6
- OVERLOOK 2/HAMLIN PH 2 & 5
- OVERLOOK 2/HAMLIN PH 3 & 4
- OVERLOOK AT HAMLIN
- OVERSTREET CRATE
- OXFORD CHASE
- PALISADES
- PALISADES CONDO
- PANTHER VIEW
- PARK PLACE
- PARK PLACE/WINTER GARDEN
- PARK SUB
- PARKVIEW AT HAMLIN
- PARKVIEW/HAMLIN
- PLEASANT PARK
- QUESINBERRY SUB
- RAVENNA
- RAVENNA PH 1
- REGENCY OAKS F
- REGENCY OAKS PH 02 A-C
- RESERVE/CARRIAGE POINT PH 1
- RESERVE/CARRIAGE POINTE PH 1
- ROLLING HILLS AVALON ANNEX
- ROPER RESERVE
- SANCTUARY/HAMLIN
- SANCTUARY/TWIN WATERS
- SAVANNAH RIDGE SUB
- SERENADE AT OVATION
- SERENADE AT OVATION PHASE I
- SERENADE/OVATION PH 1
- SHOREFRONT COVE
- SHOWALTER PARK
- SIGNATURE LAKES
- SIGNATURE LAKES PARCEL 1A
- SIGNATURE LAKES PARCEL 1D
- SIGNATURE LAKES PH 02 A B H I J
- SIGNATURE LAKES PH 2
- SIGNATURE LAKES PH 2A
- SIGNATURE LAKES PH 3B-1
- SIGNATURE LAKES PH 3B-4, 3B-5
- SIGNATURE LAKES PH 3B-4, 3B-53B-
- SIGNATURE LAKES PH 3B-5 & 3B-7
- SIGNATURE LAKES PH 3B-6
- SIGNATURE LAKES PRCL 01C
- SIGNATURE LAKES, INDEPENDENCE
- SIGNATURE LKS-PCL 01A
- SIGNATURE LKS-PCL 01B
- SIGNATURE LKS-PCL 01D PH 01
- SIGNATURE LKS-PCL 01D PH 02
- SILVER SPRINGS BUNGALOWS
- SILVERLEAF OAK
- SILVERLEAF OAKS
- SILVERLEAF OAKS AT HAMLIN PHASE 3A
- SILVERLEAF OAKS/HAMLIN PH 3A
- SILVERLEAF RESERVE
- SILVERLEAF RESERVE AT HAMLIN
- SILVERLEAF RESERVE AT HAMLIN PHASE 2A
- SILVERLEAF RESERVE BUNGALOWS
- SILVERLEAF RESERVE/HAMLIN
- SILVERLEAF RESERVE/HAMLIN PH 2
- SIPLIN HEIGHTS
- SOUTHERN PINES
- SOUTHERN PINES CONDO
- STONE CREEK 44/131
- STONE CRK
- STONE CRK A-1 & A-2
- STONEYBROOK WEST
- STONEYBROOK WEST 44/134
- STONEYBROOK WEST 47/78
- STONEYBROOK WEST D
- STONEYBROOK WEST I
- STONEYBROOK WEST UN 08 I
- STONEYBROOK WEST UNIT 4 REP
- STONEYBROOK WEST UNIT 8
- STONEYBROOK WEST UT 04 48 48
- STOREY GROVE
- STOREY GROVE 50
- STOREY GROVE PH 1
- STOREY GROVE PH 1A-2
- STOREY GROVE PH 1B-1A
- STOREY GROVE PH 1B-2
- STOREY GROVE PH 1B-3
- STOREY GROVE PH 1B-4
- STOREY GROVE PH 2
- STOREY GROVE PH 4
- STOREY GROVE PH 5
- STOREY GROVE PHASE 5
- STOREY GRV PH 2
- STORY ROAD BUS PARK
- SUBURBAN SHORES
- SUMMERLAKE
- SUMMERLAKE GRVS
- SUMMERLAKE GRVS PH 2
- SUMMERLAKE PD PH 01A
- SUMMERLAKE PD PH 1A
- SUMMERLAKE PD PH 1B
- SUMMERLAKE PD PH 1B A REP
- SUMMERLAKE PD PH 1B/REPLAT
- SUMMERLAKE PD PH 2A & 2B
- SUMMERLAKE PD PH 2C 2D 2E
- SUMMERLAKE PD PH 2C-2E
- SUMMERLAKE PD PH 3A
- SUMMERLAKE PD PH 3B
- SUMMERLAKE PD PH 3C
- SUMMERLAKE PD PH 4B
- SUMMERLAKE RESERVE
- SUNSET LAKES
- THE GROVE RESORT
- THE GROVE RESORT AND SPA CONDOMINIUM
- TILDEN PLACE/WINTER GARDEN
- TOWNHOMES WINTER GARDEN
- TRADITIONS SUB
- TRIBUTE AT OVATION
- TROYNELLE BY LAKE APOPKA
- TUCKER OAKS
- TUSCANY
- TUSCANY PH 02
- TWINWATERS
- VALENCIA SHORES
- VERDE PARK PH 1
- VILLAGE GROVE PH 01
- VILLAGE GROVE PH 02
- VILLAS/TUCKER OAKS
- WALKERS GROVE TOWNHOMES
- WALKERS GROVE TWNHMS
- WATERLEIGH
- WATERLEIGH PH 1A
- WATERLEIGH PH 1B
- WATERLEIGH PH 1C
- WATERLEIGH PH 2A
- WATERLEIGH PH 2B
- WATERLEIGH PH 2C-1
- WATERLEIGH PH 2C-2 & 2C-3
- WATERLEIGH PH 2D
- WATERLEIGH PH 2E
- WATERLEIGH PH 3A
- WATERLEIGH PH 3B & 3C
- WATERLEIGH PH 3B 3C & 3D
- WATERLEIGH PH 4A
- WATERLEIGH PH 4B & 4C
- WATERLEIGH PHASE 3A
- WATERLEIGH PHASE 4A
- WATERLEIGH PHASE 5
- WATERMARK
- WATERMARK PH 1A
- WATERMARK PH 1B
- WATERMARK PH 2A
- WATERMARK PH 2B
- WATERMARK PH 2C
- WATERMARK PH 3
- WATERMARK PH 4
- WATERMARK PHASE 4 97/87 LOT 704
- WATERSIDE – THE STRAND
- WATERSIDE ON JOHNS LAKE
- WATERSIDE/JOHNS LAKE PH 2A
- WATERSIDE/JOHNS LAKE PH 2B
- WATERSIDE/JOHNS LAKE PH 2C
- WATERSIDE/JOHNS LK-PH 2A
- WATERSIDE/JOHNS LK-PH 2B
- WEST LAKE HANCOCK ESTATES
- WESTCHESTER PLACE
- WESTFIELD LAKES
- WESTHAVEN
- WESTHAVEN AT OVATION
- WESTHAVEN/OVATION
- WESTLAKE MANOR 1ST ADD
- WESTSIDE TOWNHOMES
- WESTSIDE TOWNHOMES PH 04
- WESTSIDE TWNHMS
- WESTSIDE TWNHMS PH 02
- WESTSIDE TWNHMS-PH 05 A B & C
- WINCEY GROVES
- WINCEY GROVES PHASE 2
- WINCEY GRVS PH 2
- WINDING BAY
- WINDING BAY PH 1B
- WINDING BAY PH 2
- WINDING BAY PH 3
- WINDING BAY PRESERVE
- WINDTREE GARDENS CONDO PH 01
- WINDTREE GARDENS CONDO PH 02
- WINDTREE GARDENS CONDO PH 03
- WINDTREE GARDENS CONDO PH 04
- WINDTREE GARDENS CONDO PH 05
- WINDTREE GARDENS PH 6
- WINTER GARDEN SHORES
- WINTER GARDEN SHORES REP
- WINTER GARDEN TRLS 01-3
- WINTER GROVE
- WINTER OAKS
- WINTERMERE POINTE
- WOODBRIDGE ON GREEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Apr 29, 2026
789
Single Family Listed
108
Avg DOM
280
Avg $ / SqFt
$744,443
Avg List Price
Property Summary
- Located in the WINDING BAY PH 1B subdivision, 15306 GILLIGAN COURT WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $925,000 and features 4 beds, 4 baths, and has approximately 3,127 square feet of living space, and was originally constructed in 2020. The current price per square foot is $296. The average price per square foot for Single Family listings in WINTER GARDEN is $280. The average listing price for Single Family in WINTER GARDEN is $744,443. To schedule a showing of MLS#o6399653 at 15306 GILLIGAN COURT in WINTER GARDEN, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
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Courtesy of REAL ESTATE HOUSE FL INC. 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 Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty 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. 15306 GILLIGAN COURT
WINTER GARDEN, FL

