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$785,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,660 Sq. Ft.
  • Updated 1 day ago
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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!

Full Property Details for 337 Twelve Oaks Drive

General

  • Price: $785,000
  • HOA FEE: $48/month
  • HOA FEE FREQ.: Annually
  • Taxes: $9,512 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6440935
  • Updated: 9/15/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 10
  • Interior Features: Ceiling Fan(s), Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Disposal, Range, Refrigerator, Water Filtration System
  • Furnishings: Unfurnished
  • Flooring: Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Shared Amenities: Playground
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground, Screen Enclosure

Exterior

  • Exterior Features: Irrigation System, Rain Gutters, Sidewalk
  • Deck/Patio: Covered, Enclosed, Patio, Porch, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Enclosed, Patio, Porch, Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3

Location

  • Area: 32708 - Casselberrry/Winter Springs / Tuscawilla
  • County: Seminole
  • Development Name: 32708 - Casselberrry/Winter Springs / Tuscawilla
  • Subdivision: WINDING HOLLOW UNIT 5
  • Driving Directions: From Tuscawilla Road, Left on 434, Left into Winding Hollow Community at light, Take the 2nd Left on Twelve Oaks Drive, follow the Road around the curve and the home will be on the right-hand side.
  • Direction Faces: North

School Information

  • Elementary School: Layer Elementary
  • Middle School: Indian Trails Middle
  • High School: Winter Springs High

Community

  • Community Name: 32708 - Casselberrry/Winter Springs / Tuscawilla
  • Optional Amenities: Playground
  • Association: Yes
  • Assoc. Name: Premier Association Management LLC

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Heat Pump

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Electricity Connected, Sewer Connected, Street Lights

Structural Information

  • Architectural Info: Traditional
  • Architectural Style: Traditional
  • Builder: D.R. Horton
  • Exterior Const.: Block
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,660
  • Sq. Ft. Source: Public Records
  • Year Built: 2000

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.25
  • Lot Size (Sq. Ft.): 10,639
  • Lot Size: 10639
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Pond
  • Water Front Desc.: Pond

Financial Considerations

  • Association Fee: $575
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $9,512.27
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 358 WINDING HOLLOW UNIT 5 PB 54 PGS 65 THRU 68
  • Flood Zone Info: X
  • APN: 0121305NY00003580
  • Property ID: 0121305NY00003580

Listed by Watson Realty Corp

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Listing agent

— 337 Twelve Oaks Drive —

  • Watson Realty Corp

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 337 Twelve Oaks Drive

School District:Seminole County School District
NameGradesDistance
Layer Elementary School
4201 Florida 419, Winter Springs, FL 32708
K-51.1 mi
Winter Springs High School
130 Tuskawilla Road, Winter Springs, FL 32708
9-120.9 mi
Indian Trails Middle School, Winter Springs, FL
415 Tuskawilla Road, Winter Springs, FL 32708
6-81.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 337 Twelve Oaks Drive Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/15/2026
Listed
$785,000
10.58%
MLS
11/08/2023
Sold
$709,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 337 Twelve Oaks Drive

Year
Property Taxes
Change
Tax Assessment
Change
2025
$9,512
-7%
$629,983
-3%
2024
$10,241
89%
$651,556
68%
2023
$5,407
4%
$387,819
6%
2021
$5,224
-1%
$365,556
-3%
2022
$5,265
1%
$376,523
4%
2021
$5,224
3%
$360,509
4%
2018
$5,095
1%
$345,833
2%
2017
$5,064
-1%
$338,720
-4%
2019
$5,126
-3%
$352,404
4%
2016
$5,279
-1%
$340,039
1%
2015
$5,345
—
$337,675
—
2014
$5,350
-4%
$336,892
11%
2013
$5,599
—
$303,754
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Watson Realty Corp

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337 Twelve Oaks Drive, Winter Springs, FL 32708 (MLS# O6440935) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 337 Twelve Oaks Drive is currently listed for $785,000 and was received on September 15, 2026. Want to learn more about 337 Twelve Oaks Drive? Do you have questions about finding other Single Family real estate for sale in Winter Springs? You can browse all Winter Springs real estate or contact a Coldwell Banker agent to request more information.

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