Under contract-accepting backup offers. Experience Florida living at its finest in this beautifully renovated 5-bedroom, 3-bath pool home in Winter Springs’ desirable Winding Hollow community. Situated on a tranquil POND FRONT HOMESITE, this spacious home features a REMODELED SALTWATER POOL AND SPA, a flexible three-way split floor plan, and fresh exterior paint (2026) for exceptional curb appeal.
Pool and water views welcome you from the moment you enter the foyer. The versatile front office with closet can easily serve as a fifth bedroom and offers convenient access to the primary bath. Privately located on one side of the home, the owner’s suite features direct pool access, DUAL WALK-IN CLOSETS WITH BUILT IN ORGANIZERS, and an en-suite bathroom with dual vanity, tiled shower, and relaxing whirlpool tub.
Designed for both everyday living and entertaining, the open floor plan seamlessly connects the formal living and dining rooms with the spacious family room and STUNNING REMODELED KITCHEN. The kitchen is the heart of the home, showcasing an OVERSIZED GRANITE ISLAND with counter height seating, 42-inch rich wood cabinetry with crown molding, stainless steel appliances, under-cabinet lighting, tiled backsplash, glass-front accents, abundant pot drawer storage, an impressive BUTLER’S PANTRY with rollout storage, and a beverage refrigerator. The indoor laundry is conveniently located behind the kitchen with included washer and dryer, storage cabinetry and it’s already pre-plumbed for a sink.
Newer wood-look plank style ceramic tile flows throughout the main living areas, with carpet only in two secondary bedrooms. A private guest suite with an adjacent full bath and walk-in shower provides an ideal space for visitors or multigenerational living. This third bathroom has direct pool access.
The backyard is your own private retreat. The remodeled, SCREENED saltwater pool and spa were extensively updated in 2021 with a new quartz finish, tile, spillways, brick paver deck, coping, propane spa heater, and improved drainage. Enjoy peaceful pond views and Florida’s beautiful weather from the expansive 31′ x 12′ COVERED LANAI, accessible from the primary suite, living room, and family room.
Additional highlights include a 2017 roof, 2016 water heater, TESLA CHARGER, new garage door springs, metered irrigation, low-maintenance St. Augustine lawn, and a two-car garage with overhead storage racks.
Surrounded by mature trees, Winding Hollow offers two city maintained parks with playgrounds, while nearby Central Winds Park features sports fields, pickleball and basketball courts, playgrounds, walking trails, picnic pavilions, and a dog park. The 23 mile Cross Seminole Trail is accessible from the entrance of Winding Hollow too. Conveniently located just 20 minutes from Downtown Orlando, this exceptional home combines peaceful suburban living with easy access to shopping, dining, and major commuter routes.
Pool and water views welcome you from the moment you enter the foyer. The versatile front office with closet can easily serve as a fifth bedroom and offers convenient access to the primary bath. Privately located on one side of the home, the owner’s suite features direct pool access, DUAL WALK-IN CLOSETS WITH BUILT IN ORGANIZERS, and an en-suite bathroom with dual vanity, tiled shower, and relaxing whirlpool tub.
Designed for both everyday living and entertaining, the open floor plan seamlessly connects the formal living and dining rooms with the spacious family room and STUNNING REMODELED KITCHEN. The kitchen is the heart of the home, showcasing an OVERSIZED GRANITE ISLAND with counter height seating, 42-inch rich wood cabinetry with crown molding, stainless steel appliances, under-cabinet lighting, tiled backsplash, glass-front accents, abundant pot drawer storage, an impressive BUTLER’S PANTRY with rollout storage, and a beverage refrigerator. The indoor laundry is conveniently located behind the kitchen with included washer and dryer, storage cabinetry and it’s already pre-plumbed for a sink.
Newer wood-look plank style ceramic tile flows throughout the main living areas, with carpet only in two secondary bedrooms. A private guest suite with an adjacent full bath and walk-in shower provides an ideal space for visitors or multigenerational living. This third bathroom has direct pool access.
The backyard is your own private retreat. The remodeled, SCREENED saltwater pool and spa were extensively updated in 2021 with a new quartz finish, tile, spillways, brick paver deck, coping, propane spa heater, and improved drainage. Enjoy peaceful pond views and Florida’s beautiful weather from the expansive 31′ x 12′ COVERED LANAI, accessible from the primary suite, living room, and family room.
Additional highlights include a 2017 roof, 2016 water heater, TESLA CHARGER, new garage door springs, metered irrigation, low-maintenance St. Augustine lawn, and a two-car garage with overhead storage racks.
Surrounded by mature trees, Winding Hollow offers two city maintained parks with playgrounds, while nearby Central Winds Park features sports fields, pickleball and basketball courts, playgrounds, walking trails, picnic pavilions, and a dog park. The 23 mile Cross Seminole Trail is accessible from the entrance of Winding Hollow too. Conveniently located just 20 minutes from Downtown Orlando, this exceptional home combines peaceful suburban living with easy access to shopping, dining, and major commuter routes.
Property Details
Price:
$635,000
MLS #:
O6421314
Status:
Active Under Contract
Beds:
5
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDING HOLLOW
Neighborhood:
32708casselberrrywinterspringstuscawilla
Listed Date:
Jul 1, 2026
Finished Sq Ft:
2,574
Total Sq Ft:
3,397
Lot Size:
9,375 sqft / 0.22 acres (approx)
Year Built:
1999
WaterfrontPoolPrimary Bedroom Main Floor32708 – Casselberrry/winter Springs / Tuscawilla32708casselberrrywinterspringstuscawillaWinding HollowLayer ElementaryIndian Trails MiddleWinter Springs HighWaterBuyer Is Responsible For Verifying Leasing Restrictions With Appropriate Governing Bodies.1-2 Years
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Schools
Elementary School:
Layer Elementary
Middle School:
Indian Trails Middle
High School:
Winter Springs High
Interior
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile, Laminate
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Thermostat, Walk-In Closet(s), Window Treatments
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Levels
One
Exterior
Association Amenities
Fence Restrictions
Attached Garage YN
1
Community Features
Deed Restrictions, Dog Park, Park, Playground, Sidewalks
Construction Materials
Block, Concrete, Stucco
Covered Spaces
2
Direction Faces
West
Exterior Features
Irrigation System, Lighting, Private Mailbox, Sidewalk, Sliding Doors, Sprinkler Metered
Fencing
Wood
Garage Spaces
2
Lot Features
Landscaped, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener
Patio And Porch Features
Covered, Front Porch, Patio, Rear Porch, Screened
Roof
Shingle
Security Features
Security System Owned, Smoke Detector(s)
Spa Features
Heated, In Ground
View
Water
Waterfront Features
Pond
Window Features
Blinds, Window Treatments
Financial
HOA Fee
$575
HOA Fee Frequency
Annually
HOA Name
Premier Assoc. Mgmt. CFL
HOA Phone
407-645-4945
Tax Year
2025
Taxes
$3,961
Map
Community
- Address737 TIMBERWILDE AVENUE WINTER SPRINGS FL
- SubdivisionWINDING HOLLOW
- 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 Jul 28, 2026
143
Single Family Listed
83
Avg DOM
259
Avg $ / SqFt
$600,904
Avg List Price
Property Summary
- Located in the WINDING HOLLOW subdivision, 737 TIMBERWILDE AVENUE WINTER SPRINGS FL is a Single Family for sale in WINTER SPRINGS, FL, 32708. It is listed for $635,000 and features 5 beds, 3 baths, and has approximately 2,574 square feet of living space, and was originally constructed in 1999. The current price per square foot is $247. The average price per square foot for Single Family listings in WINTER SPRINGS is $259. The average listing price for Single Family in WINTER SPRINGS is $600,904. To schedule a showing of MLS#o6421314 at 737 TIMBERWILDE AVENUE in WINTER SPRINGS, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of HOMEVEST 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. 737 TIMBERWILDE AVENUE
WINTER SPRINGS, FL
