Oakland Hills Homes for Sale

4 Beds ⋅ 3 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code

Custom-built by Justice & Wood Builders, this 4-bedroom, 3-bathroom Modern Farmhouse sits on a rare 0.47-acre lot in Oakland Hills, an intimate community of just 17 homesites minutes from Historic Downtown Winter Garden. Towering, moss-draped oaks frame the property and set a peaceful tone from the moment you arrive. Inside, wide-plank wood floors and abundant natural light flow through an open-concept living space crowned by cathedral ceilings and exposed timber beams. The kitchen goes well beyond standard gourmet, with shaker cabinetry, quartz countertops, a massive blue-gray center island, a deep farmhouse sink, professional stainless steel appliances, and a natural gas range built for serious cooking. The bedrooms are generously sized and well separated. The upstairs bedroom is flexible enough to serve as a home office, gym, media room, or guest suite, and it has air-conditioned storage and a large walk-in attic. The bathrooms feature clean lines, modern fixtures, and custom tilework. The laundry room has extensive cabinetry, quartz counters, and a patterned tile backsplash. The three-car garage includes an EV adapter in the third bay. Out back, the fully fenced yard feels like your own resort, with a pool and spa surrounded by a spacious paver patio and a fire pit area for evenings outside. Downtown Winter Garden's Farmers Market, Plant Street Market, boutiques, and restaurants are minutes away by car or golf cart.

15210 E Oakland Avenue, Winter Garden

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Orange County › Winter Garden › Oakland Hills

Oakland Hills, Winter Garden

Oakland Hills is a 2020s neighborhood in west Winter Garden, in the 34787 zip code. Homes are block and stucco. Most homes fall between about 3,600 and 5,200 square feet under air, the median lot is about 0.40 acres, and a three car garage is standard.

Homes here carry an HOA, billed quarterly, typically around $828. Confirm the figure on a specific parcel before relying on it.

What the homes are

Built Essentially all built in the 2020s.
Construction Block and stucco. Shingle roofs on 85% of homes.
Size Most homes fall between about 3,600 and 5,200 square feet under air.
Bedrooms Four bedrooms is the most common plan, then five.
Garage A three car garage is standard.
Lot The median lot is about 0.40 acres.
HOA Billed quarterly, typically around $828. Confirm on a specific parcel before relying on it.

Where Oakland Hills is

Oakland Hills, centered at 28.554407, -81.612378. 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 Oakland Hills, 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	27 min	17.4
Walt Disney World	30 min	21.4
Orlando International Airport	32 min	25.8
Universal Orlando	27 min	16.4

Public schools nearby

Tildenville Elementary School 2 min, 0.5 mi
Oakland Avenue Charter School 5 min, 1.2 mi
SunRidge Elementary School 6 min, 2.0 mi
SLV High School 6 min, 2.3 mi

Private schools nearby

Family Christian School, Oakland 6 min, 2.6 mi

Parks and recreation

West Orange Trail 2 min, 0.4 mi
Butterfly Garden, WO Trail 2 min, 0.6 mi
VanderLey Park 5 min, 2.2 mi
Tildenville Park 4 min, 1.3 mi

Groceries and errands

A&E Grocery Store 4 min, 1.4 mi
ALDI 4 min, 1.8 mi
Publix Super Market at West Point Commons 5 min, 1.7 mi
Key Food Supermarket 5 min, 2.0 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Oakland Hills 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 Oakland Hills actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 2 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 Oakland Hills

$1,755,000Median sale price

$474Median per square foot

8 daysMedian days to contract

2Homes sold in 12 months

Sale prices ran from $1,720,000 to $1,790,000.

Seller concessions

50%Of sales included a seller credit

$5,000Typical credit when there was one

1 of 2Sales 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 2 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 Oakland Hills, 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 Oakland Hills in Winter Garden, 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.