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Green Oaks Homes for Sale

1600 Legion Drive, Winter Park
$3,495,000
5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code
Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

1761 Legion Drive, Winter Park
$3,265,000
5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep 02 SubDv. ⋅ 32789 Zip Code
Nearly half an acre in the heart of Winter Park. Set on a 0.42-acre oversized corner lot in Green Oaks, this custom 5-bedroom, 5.5-bath residence offers what nearby new construction rarely can: room to breathe. Where most new luxury homes in 32789 sit on a quarter- to a third-acre, this property pairs 4,949 square feet of living space with a rare three-car garage, a newly added semi-circular driveway, and a backyard with genuine space for play, gardening, or entertaining on a grand scale. Completed in 2017 and meticulously maintained by its original owner, the home was thoughtfully reimagined by renowned designer Ted Maines with high-end finishes throughout. The floor plan balances formal entertaining with relaxed everyday living. The foyer opens to a gracious formal living room, with a dedicated dining room to the right and a private office to the left, an ideal setting for hosting guests or working from home. Toward the rear of the home, the large gourmet kitchen with custom cabinetry and Sub-Zero and Wolf appliances flows into a sunny eat-in dining area and a family room anchored by a fireplace, with expansive sliding glass doors connecting to the outdoor living spaces. The private first-floor primary suite opens directly to the lanai and pool and includes a spa-inspired bath with steam shower and custom his-and-her walk-in closets. A second ground-floor bedroom offers flexibility for guests or multigenerational living. Upstairs, a spacious loft with custom dry bar leads to a media room and three additional en-suite bedrooms. Enhancements include a whole-house generator supported by a 250-gallon buried propane tank and new pool solar equipment. Year-round comfort comes from three A/C systems serving four climate zones, including a zone dedicated to the primary suite. Outdoors, a heated saltwater pool and spa, stone decking, outdoor shower, and ambient lighting make the most of the expansive grounds. A homesite of this size, this close to the shops, dining, parks, and charm of downtown Winter Park, is increasingly hard to find.

1761 Legion Drive, Winter Park

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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 most often 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 Most often built in the 1960s (47% of homes), with homes from 1957 to 2026.
  • Construction Block and stucco. Shingle roofs on 87% of homes.
  • 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 November 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

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 7 November 2025 through 2 November 2026, refreshed monthly and current as of November 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.

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