Welcome to this beautifully updated 4-bedroom, 3-bathroom pool home in Winding Hollow, offering over 2,500 square feet of living space, a split-bedroom floor plan, and a 3-car garage! A double-door entry welcomes you inside, where fresh paint throughout and new flooring create an inviting setting. Two separate living spaces—a formal living room and a spacious family room—provide flexibility for entertaining and everyday living, while a formal dining room and a casual breakfast area provides space for every occasion.
The updated kitchen features new cabinetry, granite countertops, stainless steel appliances, an island, breakfast bar seating, an updated backsplash, and a dedicated coffee and wine bar. Whether preparing a meal or hosting a gathering, there is plenty of room to cook, serve, and connect.
Privately situated on the opposite side of the home from the guest bedrooms, the spacious primary suite features its own sitting area with French doors—an ideal space for a nursery, home office, or quiet retreat—along with access to the lanai. The primary bathroom includes dual vanities with updated countertops, a soaking tub, a separate shower, and a private water closet. Spacious secondary bedrooms share an updated Jack-and-Jill bathroom with a tiled tub/shower combination, while the fourth bedroom enjoys convenient access to the updated third full bathroom, complete with a shower and direct pool access.
Step outside to an expansive covered lanai beneath the home’s shingled roof, providing generous sheltered space for outdoor dining and relaxing. The screened-in pool features a waterfall sprayer, while mature landscaping and a partially fenced backyard provide an inviting backdrop with green space beyond the pool enclosure.
Additional highlights include an interior laundry room, extra attic storage, south-facing front exposure, and a roof and Trane A/C system installed in 2018. Conveniently located near shopping, dining, schools, Winter Springs Town Center, and area recreation, this home combines thoughtful updates, spacious gathering areas, and inviting outdoor living. Schedule your private showing today!
Buyer and buyer’s agent to independently verify all property information, including measurements, square footage, room dimensions, schools, permits, and any other details deemed important to the buyer.
The updated kitchen features new cabinetry, granite countertops, stainless steel appliances, an island, breakfast bar seating, an updated backsplash, and a dedicated coffee and wine bar. Whether preparing a meal or hosting a gathering, there is plenty of room to cook, serve, and connect.
Privately situated on the opposite side of the home from the guest bedrooms, the spacious primary suite features its own sitting area with French doors—an ideal space for a nursery, home office, or quiet retreat—along with access to the lanai. The primary bathroom includes dual vanities with updated countertops, a soaking tub, a separate shower, and a private water closet. Spacious secondary bedrooms share an updated Jack-and-Jill bathroom with a tiled tub/shower combination, while the fourth bedroom enjoys convenient access to the updated third full bathroom, complete with a shower and direct pool access.
Step outside to an expansive covered lanai beneath the home’s shingled roof, providing generous sheltered space for outdoor dining and relaxing. The screened-in pool features a waterfall sprayer, while mature landscaping and a partially fenced backyard provide an inviting backdrop with green space beyond the pool enclosure.
Additional highlights include an interior laundry room, extra attic storage, south-facing front exposure, and a roof and Trane A/C system installed in 2018. Conveniently located near shopping, dining, schools, Winter Springs Town Center, and area recreation, this home combines thoughtful updates, spacious gathering areas, and inviting outdoor living. Schedule your private showing today!
Buyer and buyer’s agent to independently verify all property information, including measurements, square footage, room dimensions, schools, permits, and any other details deemed important to the buyer.
Property Details
Price:
$650,000
MLS #:
O6449643
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDING HOLLOW UNIT 4
Neighborhood:
32708casselberrrywinterspringstuscawilla
Listed Date:
Oct 17, 2026
Finished Sq Ft:
2,533
Total Sq Ft:
3,466
Lot Size:
9,585 sqft / 0.22 acres (approx)
Year Built:
1998
See this Listing
Schools
Elementary School:
Layer Elementary
Middle School:
Indian Trails Middle
High School:
Winter Springs High
Interior
Appliances
Dishwasher, Microwave, Range, Refrigerator, Washer
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Tile, Hardwood
Heating
Central
Interior Features
Ceiling Fan(s), Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Attached Garage YN
1
Construction Materials
Block, Concrete, Stucco
Covered Spaces
3
Direction Faces
West
Exterior Features
Sidewalk
Fencing
Fenced, Masonry
Garage Spaces
3
Lot Features
Landscaped, Level, Private
Open Parking YN
1
Parking Features
Driveway
Patio And Porch Features
Covered, Patio, Screened
Roof
Shingle
Security Features
Smoke Detector(s)
Financial
HOA Fee
$42
HOA Fee Frequency
Monthly
HOA Name
Lori Collier- Greystone Management
HOA Phone
407-645-4945
Tax Year
2025
Taxes
$5,230
Map
Community
- Address1105 SHADOWBROOK TRAIL WINTER SPRINGS FL
- SubdivisionWINDING HOLLOW UNIT 4
- CityWINTER SPRINGS
- CountySeminole
- Zip Code32708
Subdivisions in WINTER SPRINGS
- ARROWHEAD AT TUSCAWILLA UNIT 1
- ARROWHEAD AT TUSCAWILLA UNIT 2
- AVERY PARK
- BAHAMA RANCHES
- BARCLAY RESERVE TWNHMS
- BARRINGTON ESTATES
- BARRINGTON ESTS
- BAY TREE SEC 09
- BAY TREE SEC 10
- BAYTREE VILLAGE
- BEAR CREEK ESTATES
- BENTLEY GREEN UNIT 1
- CARRINGTON WOODS UNIT 2
- CASA PARK VILLAS PH 1
- CASA PARK VILLAS PH 2
- CASSELBERRY COMMERCE VILLAGE A CONDO
- CHESTNUT ESTATES PH 1
- CHESTNUT RIDGE
- COUNTRY CLUB VILLAGE UNIT 1
- COUNTRY CLUB VILLAGE UNIT 3
- CREEKS RUN
- CYPRESS CLUB
- CYPRESS VILLAGE 3RD REP TR C PH 1
- D R MITCHELLS SURVEY OF THE LEVY GRANT
- DEER RUN UNIT 19A
- DEER RUN UNIT 19B
- DEERSONG
- DEERSONG 2
- EAGLES POINT PH 6
- EAGLES WATCH PH 1
- ENTZMINGER FARMS ADD 2
- FAIRWAY OAKS UNIT 1
- FLAMINGO SPGS
- FOX GLEN AT CHELSEA PARC TUSCAWILLA PH 2
- FOXMOOR UNIT 2
- FOXMOOR UNIT 3
- GEORGETOWNE UNIT 1
- GEORGETOWNE UNIT 3
- GLEN EAGLE UNIT 1
- GLEN EAGLE UNIT 4
- GOLFSIDE VILLAS
- GREENBRIAR SUB PH 1
- GREENBRIAR SUB PH 2
- GREENS AT TUSCAWILLA
- GREENSPOINTE
- HACIENDA VILLAGE
- HARBOR WINDS
- HERITAGE COMMONS
- HERITAGE PARK TOWNHOMES
- HERITAGE PARK TWNHMS
- HICKORY GROVE
- HIGHLAND VILLAGE 1
- HIGHLAND VILLAGE 2
- HIGHLANDS SEC 1
- HIGHLANDS SEC 4
- HOLLOWBROOK PH 2
- HOWELL CREEK RESERVE PH 2
- INDIAN RIDGE
- INDIAN RIDGE PH 2
- JESUPS LANDING
- JESUPS RESERVE TWNHMS REP
- JESUPS RESERVES REPLAT
- MOUNT GREENWOOD UNIT 2 OF
- MOUNT GREENWOOD UNIT 4
- MOUNT GREENWOOD UNIT 5 OF
- NORTH ORLANDO
- NORTH ORLANDO 1ST ADD
- NORTH ORLANDO 2ND ADD
- NORTH ORLANDO 2ND ADD RESUBD OF BLK 5 & TR A
- NORTH ORLANDO RANCHES SEC 02
- NORTH ORLANDO RANCHES SEC 02A
- NORTH ORLANDO RANCHES SEC 06
- NORTH ORLANDO RANCHES SEC 09
- NORTH ORLANDO RANCHES SEC 10
- NORTH ORLANDO TERRACE UNIT 1 SEC 5
- NORTH ORLANDO TERRACE UNIT 1 SEC 6
- NORTH ORLANDO TERRACE UNIT 2 SEC 8
- NORTH ORLANDO TERRACE UNIT 2 SEC 9
- NORTH ORLANDO TOWNSITE 4TH ADD REP
- OAK FOREST UNIT 2A
- OAK FOREST UNIT 3
- OAK FOREST UNIT 4
- OAK FOREST UNIT 6
- OAK FOREST UNIT 8
- PARKSTONE
- PARKSTONE UNIT 2
- PARKSTONE UNIT 3
- PARKSTONE UNIT 4
- SEASONS THE
- SEMINOLE CROSSING TWNHMS
- SEVEN OAKS
- SEVEN OAKS TWO
- SEVILLE CHASE
- SHEOAH A CONDO SEC 2
- SHEOAH SEC 1
- STONE GABLE
- SUNRISE UNIT 2-B
- SUNRISE UNIT 2C
- SUNRISE UNIT 2D
- SUNRISE UNIT TWO C
- SUNRISE VILLAGE UNIT 1
- TALIS CROSSING
- THE OAKS SUB
- TUSCA OAKS
- TUSCANY PLACE PH 1
- TUSCAWILLA
- TUSCAWILLA UNIT 06
- TUSCAWILLA UNIT 07
- TUSCAWILLA UNIT 09-B
- TUSCAWILLA UNIT 14A
- TUSCAWILLA UNIT 14B
- TUSKABAY PH 1
- TUSKAWILLA CROSSINGS 34’S
- TUSKAWILLA CROSSINGS PH 1
- TUSKAWILLA CROSSINGS PH 2
- TUSKAWILLA OFFICE PARK
- TUSKAWILLA POINT
- TUSKAWILLA TRAIL SUBD
- WATTS FARMS
- WEDGEWOOD TENNIS VILLAS
- WILDWOOD
- WILLIAMSON HEIGHTS
- WILLOW RUN
- WINDING HOLLOW UNIT 2
- WINTER SPGS
- WINTER SPGS TOWN CENTER A REP
- WINTER SPGS UNIT 3
- WINTER SPGS UNIT 4
- WINTER SPGS VILLAGE PH 2
- WINTER SPRINGS UNIT 4
Market Summary
Current real estate data for Single Family in WINTER SPRINGS as of Oct 22, 2026
125
Single Family Listed
84
Avg DOM
260
Avg $ / SqFt
$542,845
Avg List Price
Property Summary
- Located in the WINDING HOLLOW UNIT 4 subdivision, 1105 SHADOWBROOK TRAIL WINTER SPRINGS FL is a Single Family for sale in WINTER SPRINGS, FL, 32708. It is listed for $650,000 and features 4 beds, 3 baths, and has approximately 2,533 square feet of living space, and was originally constructed in 1998. The current price per square foot is $257. The average price per square foot for Single Family listings in WINTER SPRINGS is $260. The average listing price for Single Family in WINTER SPRINGS is $542,845. To schedule a showing of MLS#o6449643 at 1105 SHADOWBROOK TRAIL in WINTER SPRINGS, FL, contact your CENTURY 21 Carioti agent at 2392986550.
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Courtesy of CALL IT CLOSED INTL REALTY. 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. 1105 SHADOWBROOK TRAIL
WINTER SPRINGS, FL
