Homes In Orlando For Sale Search
$3,265,000
5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep 02 SubDv. ⋅ 32789 Zip Code
One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, and an unbeatable location. Completed in 2017 and first sold in 2018, this 5-bedroom, 5.5-bath home has been meticulously maintained by its original owner and enhanced with high-end designer finishes. Much of the interior was thoughtfully reimagined by renowned designer Ted Maines, resulting in a sophisticated yet timeless aesthetic throughout. Perfectly positioned on a prime oversized corner lot, this remarkable residence blends transitional architecture with modern elegance. Expansive sliding glass doors fill the open-concept living spaces with natural light while creating a seamless connection between the indoors and outdoors. The main living area flows effortlessly from the formal living room and spacious dining area into the gourmet kitchen, complete with custom cabinetry, Carrara marble surfaces, and premium Sub-Zero and Wolf appliances. A refined yet inviting family room with a fireplace provides the perfect setting for everyday living and entertaining. The private first-floor primary suite offers direct access to the lanai and heated saltwater pool and is complemented by a spa-inspired bath with a steam shower and custom his-and-her walk-in closets. A secondary ground-floor bedroom provides exceptional flexibility for guests, multigenerational living, or a private home office. Upstairs, a spacious loft with a custom dry bar leads to a versatile media room. Three additional en-suite bedrooms complete the second level. Recent enhancements include a whole-house generator supported by a 250-gallon buried propane tank, new pool solar equipment, a newly added semi-circular driveway that enhances both curb appeal and functionality, two newer A/C units, and a new 2026 A/C system featuring re-engineered, high-efficiency ductwork designed to provide optimal climate control throughout the home. The outdoor living space is equally impressive, featuring a heated saltwater pool and spa with a cascading waterfall, elegant stone decking, an outdoor shower, ambient lighting, and a covered summer kitchen—perfect for year-round entertaining. A rare three-car garage completes this exceptional property. All of this is just moments from the shops, dining, parks, and unmistakable charm of downtown Winter Park

1761 Legion Drive, Winter Park
Start Your Search

Orange County › Winter Park › Green Oaks

Green Oaks, Winter Park

Green Oaks is a neighborhood in north Winter Park, in the 32789 zip code, built mostly in the 1960s. Homes are block and stucco. Most homes fall between about 2,300 and 5,300 square feet under air, the median lot is roughly a third of an acre, and a two car garage is standard.

Most of Green Oaks carries no mandatory HOA.

What the homes are

  • Built Mostly built in the 1960s, with homes from 1957 to 2026.
  • Construction Block and stucco. Shingle roofs are near universal.
  • Style Traditional. Predominantly two story.
  • Size Most homes fall between about 2,300 and 5,300 square feet under air.
  • Bedrooms Five bedrooms is the most common plan, then four.
  • Garage A two car garage is standard.
  • Lot The median lot is roughly a third of an acre.
  • HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.

Where Green Oaks is

Green Oaks, centered at 28.615458, -81.358466. 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 Green Oaks, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving toTimeMiles
Downtown Orlando19 min7.5
Walt Disney World33 min27.5
Orlando International Airport35 min28.9
Universal Orlando25 min15.5

Public schools nearby

  • Lake Sybelia Elementary School 8 min, 2.1 mi
  • Hungerford Elementary School 7 min, 1.9 mi
  • Dommerich Elementary School 10 min, 3.2 mi
  • Lakemont Elementary School 8 min, 2.5 mi

Private schools nearby

  • Celandine Life-Preparatory Academy 4 min, 0.8 mi
  • Orlando Gifted Academy 4 min, 1.0 mi
  • Maitland Montessori School 6 min, 1.7 mi
  • St. Margaret Mary Catholic School 7 min, 1.5 mi

Parks and recreation

  • Villa View Park 3 min, 0.7 mi
  • Fort Maitland Park 3 min, 0.8 mi
  • Oaks Park 4 min, 0.8 mi
  • Lake Lily Park 5 min, 1.2 mi

Groceries and errands

  • Whole Foods Market 5 min, 1.2 mi
  • Publix Super Market at Maitland Place 6 min, 1.6 mi
  • Publix Super Market at Winter Park Village 6 min, 1.4 mi
  • The Ancient Olive Gourmet of Winter Park 9 min, 1.6 mi

Nearest is not the same as zoned. The schools above are the closest ones to Green Oaks 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 Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Green Oaks actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 5 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 September 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Green Oaks

$4,550,000Median sale price
$866Median per square foot
4 daysMedian days to contract
5Homes sold in 12 months

Sale prices ran from $1,424,000 to $6,111,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

By size

Home sizeSalesMedian priceMedian $/sq ftMedian days
3,000 sq ft and up4$4,977,500$1,0424 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.

Seller concessions

40%Of sales included a seller credit
$3,000Typical credit when there was one
2 of 5Sales 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

Cash 5 sales100%

Cash was 100% 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 Green Oaks, 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 Green Oaks in Winter Park, Orange County, covering closed sales from 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 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.