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
Market Summary
Current real estate data for Single Family in WINTER SPRINGS as of Oct 19, 2026
120
Single Family Listed
84
Avg DOM
259
Avg $ / SqFt
$547,785
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 $547,785. To schedule a showing of MLS#o6440935 at 337 TWELVE OAKS DRIVE in WINTER SPRINGS, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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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 InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. 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
