337 Twelve Oaks Drive, FL337 Twelve Oaks Drive, FL337 Twelve Oaks Drive, FL
Stellar MLS
1 / 67

$785,000

337 Twelve Oaks Drive

Winter Springs, FL 32708

Listing updated: September 16, 2026 at 6:48 AM ET

Active
Stellar MLSListing courtesy of Watson Realty Corp · Virginia Bellhorn · MLS #O6440935 · Active · 407-359-2300
5
Beds
4
Baths
3,660
Sq Ft
0.25
Acres
2000
Built
WaterfrontWater accessPrivate pool3-car garage$214/sqft
Single Family Residence

Property type

2000

Year built

10,639 sqft

Lot size

$214

Price / sq ft

$48/mo

HOA dues

1

Day on market

3

Garage spaces

X

Flood zone

About this home

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!

Estimated monthly payment

Principal & interest$3,969
Property taxes$793
Home insurance (est.)$360
HOA dues$48

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history1 days on market

  1. Status: Active
    Sep 15, 2026
  2. Listed$785,000
    Sep 15, 2026
  3. Price increased$785,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
1
Subdivision
Winding Hollow Unit 5
County
Seminole
Year built
2000
Living area
3,660 sq ft
Price/sq ft
$214
Building area
4,612 sq ft (Public Records)
Lot size
10,639 sq ft
Lot category
1/4 to less than 1/2
Flood zone
X (12117C0160F)
Garage
3 spaces
Pool
Private pool
Annual taxes
$9,512 (2025)
Parcel #
01-21-30-5NY-0000-3580
Zoning
R-1A
MLS #
O6440935

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Interior Details

Bedrooms
5
Full bathrooms
3
Half bathrooms
1
Flooring
Carpet, Ceramic Tile
Appliances
Dishwasher, Disposal, Range, Refrigerator, Water Filtration System
Interior features
Ceiling Fans(s), Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
Laundry
Inside, Laundry Room
Stories / Levels
Two
Direction faces
North

Heating & Cooling

Heating
Heat Pump
Cooling
Central Air

Parking

Garage spaces
3
Attached garage
Yes

HOA & Financial

HOA fee
$575 / Annually
Monthly HOA
$48/mo
Total monthly fees
$48/mo
Total annual fees
$575
HOA name
Premier Association Management LLC
CDD
No
Homestead exemption
Yes
Min lease term
1-2 Years
Listing terms
Cash, Conventional, FHA, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
No
Additional lease restrictions
Buyer to verify with HOA rules and regulations.

Exterior & Construction

Exterior features
Rain Gutters, Sidewalk
Construction materials
Block
Roof
Shingle
Foundation
Slab
Pool
Private pool
Waterfront
Yes
Water access
Yes
Road surface
Paved

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
BB/HS Internet Available, Electricity Connected, Sewer Connected

Community

Pets allowed
Yes

Schools

ElementaryALayer ElementaryGreatSchools ↗
MiddleAIndian Trails MiddleGreatSchools ↗
High SchoolWinter Springs HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
KitchenFirst25x14
Living RoomFirst13x21
Family RoomFirst11x13
Dining RoomFirst21x11
Bonus RoomSecond24x20
Primary BedroomFirst14x17
Bedroom 2Second15x13
Bedroom 3Second16x14
Bedroom 4Second16x11
Bedroom 5First13x11

Listing Details

Listing date
2026-09-15
On market date
2026-09-15
Original list price
$785,000
Occupant type
Owner
MLS area
32708 - Casselberrry/Winter Springs / Tuscawilla
Listing AOR
Orlando Regional
Status changed
2026-09-15
Tax legal description
LOT 358 WINDING HOLLOW UNIT 5 PB 54 PGS 65 THRU 68

Flood risk

Minimal riskFEMA Zone XPanel 12117C0160F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

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.

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Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of September 16, 2026 at 6:48 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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