WELCOME HOME to 337 Twelve Oaks Drive!
This stunning Wisteria II Model offers 5 bedrooms, 3.5 bathrooms, and 3,660 square feet of beautifully maintained living space, perfectly positioned on an oversized .25-acre premium waterfront lot in the sought-after Winding Hollow community of Winter Springs.
From the moment you arrive, you’ll appreciate the lush landscaping, exceptional curb appeal, and pride of ownership throughout this immaculate home. Inside, an abundance of thoughtful upgrades and elegant finishes create the perfect blend of comfort, style, and functionality.
The renovated gourmet kitchen is truly the heart of the home, featuring floor-to-ceiling custom cabinetry, quartz countertops, a large center island, stainless steel appliance package, stylish tile backsplash, and a water filtration system. The spacious kitchen opens beautifully to the expansive family room, creating an ideal space for everyday living and entertaining.
Additional upgrades include all-new windows and doors, beautiful wood-plank ceramic tile flooring, plantation shutters, and newer attic insulation, providing both style and improved energy efficiency.
The first floor features a spacious primary suite, a versatile den/office, formal living room, formal dining room, and a huge family room with serene views of the private pool, expansive patio, and tranquil pond. The primary suite provides a peaceful retreat with plenty of space and privacy.
Upstairs, you’ll find three additional generously sized bedrooms, each offering large closets, along with two full bathrooms and an impressive 17′ x 24′ game room—perfect for a media room, playroom, home gym, or additional entertaining space.
The three-car garage provides abundant storage and parking, and features a custom garage floor coating for a polished, durable finish.
Step outside and experience your own private oasis. The sparkling pool, spacious patio, lush landscaping, and peaceful waterfront setting create the perfect backdrop for relaxing mornings, afternoon swims, and memorable gatherings with family and friends.
Located in desirable Winding Hollow, this home offers an exceptional Winter Springs lifestyle with walking trails, community park areas, close proximity to top-rated Seminole County schools, shopping, Winter Springs Town Center, restaurants, Central Winds Park, the Seminole Trail, and more.
With its premium waterfront setting, private pool, spacious floor plan, three-car garage, extensive upgrades, and beautifully appointed living spaces, 337 Twelve Oaks Drive is more than just a home—it’s a lifestyle!
This stunning Wisteria II Model offers 5 bedrooms, 3.5 bathrooms, and 3,660 square feet of beautifully maintained living space, perfectly positioned on an oversized .25-acre premium waterfront lot in the sought-after Winding Hollow community of Winter Springs.
From the moment you arrive, you’ll appreciate the lush landscaping, exceptional curb appeal, and pride of ownership throughout this immaculate home. Inside, an abundance of thoughtful upgrades and elegant finishes create the perfect blend of comfort, style, and functionality.
The renovated gourmet kitchen is truly the heart of the home, featuring floor-to-ceiling custom cabinetry, quartz countertops, a large center island, stainless steel appliance package, stylish tile backsplash, and a water filtration system. The spacious kitchen opens beautifully to the expansive family room, creating an ideal space for everyday living and entertaining.
Additional upgrades include all-new windows and doors, beautiful wood-plank ceramic tile flooring, plantation shutters, and newer attic insulation, providing both style and improved energy efficiency.
The first floor features a spacious primary suite, a versatile den/office, formal living room, formal dining room, and a huge family room with serene views of the private pool, expansive patio, and tranquil pond. The primary suite provides a peaceful retreat with plenty of space and privacy.
Upstairs, you’ll find three additional generously sized bedrooms, each offering large closets, along with two full bathrooms and an impressive 17′ x 24′ game room—perfect for a media room, playroom, home gym, or additional entertaining space.
The three-car garage provides abundant storage and parking, and features a custom garage floor coating for a polished, durable finish.
Step outside and experience your own private oasis. The sparkling pool, spacious patio, lush landscaping, and peaceful waterfront setting create the perfect backdrop for relaxing mornings, afternoon swims, and memorable gatherings with family and friends.
Located in desirable Winding Hollow, this home offers an exceptional Winter Springs lifestyle with walking trails, community park areas, close proximity to top-rated Seminole County schools, shopping, Winter Springs Town Center, restaurants, Central Winds Park, the Seminole Trail, and more.
With its premium waterfront setting, private pool, spacious floor plan, three-car garage, extensive upgrades, and beautifully appointed living spaces, 337 Twelve Oaks Drive is more than just a home—it’s a lifestyle!
Property Details
Price:
$785,000
MLS #:
O6440935
Status:
Active
Beds:
5
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDING HOLLOW UNIT 5
Neighborhood:
32708casselberrrywinterspringstuscawilla
Listed Date:
Sep 15, 2026
Finished Sq Ft:
3,660
Total Sq Ft:
4,612
Lot Size:
10,639 sqft / 0.25 acres (approx)
Year Built:
2000
See this Listing
Schools
Elementary School:
Layer Elementary
Middle School:
Indian Trails Middle
High School:
Winter Springs High
Interior
Appliances
Dishwasher, Disposal, Range, Refrigerator, Water Filtration System
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Ceramic Tile
Heating
Heat Pump
Interior Features
Ceiling Fan(s), Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Traditional
Association Amenities
Playground
Attached Garage YN
1
Construction Materials
Block
Covered Spaces
3
Direction Faces
North
Exterior Features
Irrigation System, Rain Gutters, Sidewalk
Garage Spaces
3
Lot Features
Landscaped, Oversized Lot
Patio And Porch Features
Covered, Enclosed, Patio, Porch, Rear Porch, Screened
Roof
Shingle
View
Water
Waterfront Features
Pond
Financial
HOA Fee
$575
HOA Fee Frequency
Annually
HOA Name
Premier Association Management LLC
HOA Phone
407-333-7787
Tax Year
2025
Taxes
$9,512
Map
Community
- Address337 TWELVE OAKS DRIVE WINTER SPRINGS FL
- SubdivisionWINDING HOLLOW UNIT 5
- 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 Sep 16, 2026
112
Single Family Listed
96
Avg DOM
259
Avg $ / SqFt
$579,786
Avg List Price
Property Summary
- Located in the WINDING HOLLOW UNIT 5 subdivision, 337 TWELVE OAKS DRIVE WINTER SPRINGS FL is a Single Family for sale in WINTER SPRINGS, FL, 32708. It is listed for $785,000 and features 5 beds, 4 baths, and has approximately 3,660 square feet of living space, and was originally constructed in 2000. The current price per square foot is $214. 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 $579,786. To schedule a showing of MLS#o6440935 at 337 TWELVE OAKS DRIVE in WINTER SPRINGS, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of WATSON REALTY CORP. 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. 337 TWELVE OAKS DRIVE
WINTER SPRINGS, FL
