Winding Hollow Homes for Sale

5 Beds ⋅ 4 Baths ⋅ Winding Hollow Unit 5 SubDv. ⋅ 32708 Zip Code

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!

337 Twelve Oaks Drive, Winter Springs

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Seminole County › Winter Springs › Winding Hollow

Winding Hollow, Winter Springs

Winding Hollow is a 1990s neighborhood in east Winter Springs, in the 32708 zip code. Homes are block and stucco, predominantly single story. Most homes fall between about 2,200 and 3,700 square feet under air, the median lot is roughly a quarter acre, and a two car garage is standard.

Homes here carry an HOA, billed annually, typically around $350. Confirm the figure on a specific parcel before relying on it.

What the homes are

Built Mostly built in the 1990s, with homes from 1994 to 2000.
Construction Block and stucco. Shingle roofs are near universal.
Size Most homes fall between about 2,200 and 3,700 square feet under air.
Bedrooms Four bedrooms is the most common plan, then five.
Garage A two car garage is standard.
Lot The median lot is roughly a quarter acre.
HOA Billed annually, typically around $350. Confirm on a specific parcel before relying on it.

Where Winding Hollow is

Winding Hollow, centered at 28.696699, -81.279874. Drag to explore.

Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Winding Hollow, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving to	Time	Miles
Downtown Orlando	30 min	23.0
Orlando International Airport	33 min	28.9
Winter Park	28 min	12.1
Heathrow and Lake Mary offices	28 min	11.2

Public schools nearby

Winter Springs High School 6 min, 1.8 mi
Layer Elementary School 5 min, 1.8 mi
Keeth Elementary School 7 min, 3.0 mi
Winter Springs Elementary School 8 min, 2.9 mi

Private schools nearby

MAGAL Hebrew School 6 min, 2.5 mi
Reach Beyond Academy 6 min, 2.5 mi

Parks and recreation

Winding Hollow Park 1 min, 0.3 mi
Oak Hollow Park 2 min, 0.5 mi
Central Winds Park 8 min, 2.1 mi
Mount Greenwood Park 7 min, 2.6 mi

Groceries and errands

ALDI 6 min, 2.3 mi
Publix Super Market at Winter Springs Town Center 6 min, 2.0 mi
Winn-Dixie 9 min, 3.4 mi
Key Food Supermarkets 11 min, 4.2 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Winding Hollow by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Seminole County Public Schools before it matters to a decision.

Places and drive times from Google, checked 9 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Winding Hollow actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 13 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated October 2026.

What homes sold for in Winding Hollow

$588,300Median sale price

$232Median per square foot

10 daysMedian days to contract

13Homes sold in 12 months

Sale prices ran from $510,000 to $749,000.

By size

Home size	Sales	Median price	Median $/sq ft	Median days
2,000 to 3,000 sq ft	9	$575,000	$242	10 days
3,000 sq ft and up	4	$670,025	$194	40 days

Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.

Price cuts and time to contract

Median days to go under contract. Shorter is better.

Never reduced 7 sales, closed at 100% of asking6 days

Reduced at least once 6 sales, closed at 97.4% of the reduced price92 days

Sellers who held their number went under contract in a median 6 days. Sellers who had to reduce took 92 days and still closed at 97.4% of their already reduced price, after a typical cut of $29,550.

Seller concessions

62%Of sales included a seller credit

$7,562Typical credit when there was one

8 of 13Sales carrying a credit

A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.

How buyers paid

Conventional 9 sales69%

Cash 2 sales15%

FHA 1 sale8%

VA 1 sale8%

Cash was 15% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Winding Hollow, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Winding Hollow in Winter Springs, Seminole County, covering closed sales from 13 October 2025 through 8 October 2026, refreshed monthly and current as of October 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.