Winter Oaks Homes for Sale

4 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code

Welcome to Winter Oaks, one of Winter Garden’s most desirable communities, just minutes from the charm, dining, shopping, and entertainment of historic Downtown Winter Garden. Tucked away at the end of a quiet cul-de-sac and situated on one of the community’s largest lots, this beautifully maintained 4-bedroom, 3-bath home offers an exceptional combination of space, character, and location. Step inside to an impressive 20-foot foyer that creates a dramatic first impression and opens to spacious living areas designed for both everyday comfort and entertaining. Thoughtful architectural details are found throughout the home, including 9'4" ceilings, hardwood flooring, Craftsman-style trim, tall baseboards, crown molding, wainscoting, oak stairs, custom built-ins, and detailed window trim. The inviting kitchen features 42-inch cabinetry, Quartz countertops, stainless steel appliances, generous prep and storage space, and a charming built-in banquette for casual dining. Sliding glass doors extend the living space to a screened patio overlooking the expansive backyard. A full laundry room with utility sink is conveniently located nearby. The first floor also features an elegant formal dining room accented with beautiful wainscoting, along with a bedroom that can easily serve as a private home office or guest suite and an adjacent full bathroom. Upstairs, the spacious Owner’s Suite provides a peaceful retreat with tray ceilings, crown molding, and a private balcony. The en-suite Fully Remodeled bathroom offers dual vanities, a beautiful super shower, and an impressive oversized walk-in closet. Two additional bedrooms and an upgraded full bathroom complete the second floor. Outside, enjoy the privacy and possibilities of the oversized fenced yard, offering plenty of room for outdoor entertaining, recreation, or creating your own backyard retreat. The home has been lovingly maintained and thoughtfully improved over the years, including a new roof in 2020, A/C Air Handler in 2023, energy efficient replacement windows throughout most of the home. With its generous homesite, cul-de-sac location, distinctive architectural details, and convenient access to Downtown Winter Garden by foot or bike, this home offers a wonderful opportunity to enjoy one of Central Florida’s most sought-after communities.

707 Chase Oaks Court, Winter Garden

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Orange County › Winter Garden › Winter Oaks

Winter Oaks, Winter Garden

Winter Oaks is a 2000s neighborhood in west Winter Garden, in the 34787 zip code. Homes are block and stucco. Most homes fall between about 1,700 and 3,100 square feet under air, the median lot is roughly a fifth of an acre, and a two car garage is standard.

Homes here carry an HOA, billed annually, typically around $400. Confirm the figure on a specific parcel before relying on it.

What the homes are

Built Essentially all built in the 2000s.
Construction Block and stucco. Shingle roofs are near universal.
Style Traditional, Contemporary, Bungalow. Predominantly two story.
Size Most homes fall between about 1,700 and 3,100 square feet under air.
Bedrooms Three bedrooms is the most common plan, then four.
Garage A two car garage is standard.
Lot The median lot is roughly a fifth of an acre.
HOA Billed annually, typically around $400. Confirm on a specific parcel before relying on it.

Where Winter Oaks is

Winter Oaks, centered at 28.559688, -81.598516. 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 Winter Oaks, 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	28 min	17.0
Walt Disney World	30 min	21.0
Orlando International Airport	33 min	25.4
Universal Orlando	27 min	16.0

Public schools nearby

Tildenville Elementary School 4 min, 1.0 mi
SLV High School 5 min, 1.4 mi
Dillard Street Elementary School 6 min, 1.7 mi
Maxey Elementary School 6 min, 1.5 mi

Private schools nearby

Foundation Academy, Plant Street Campus 7 min, 1.3 mi

Parks and recreation

Veterans Memorial Park 3 min, 0.7 mi
Butterfly Garden, WO Trail 4 min, 1.1 mi
West Orange Trail 5 min, 1.6 mi
Maple Street Park 5 min, 1.4 mi

Groceries and errands

ALDI 4 min, 1.0 mi
The Ancient Olive Gourmet of Winter Garden 6 min, 1.5 mi
Key Food Supermarket 5 min, 1.1 mi
Tea Bar 5 min, 1.4 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Winter 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 Winter 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 Winter Oaks

$640,000Median sale price

$271Median per square foot

21 daysMedian days to contract

5Homes sold in 12 months

Sale prices ran from $578,000 to $715,000.

By size

Home size	Sales	Median price	Median $/sq ft	Median days
2,000 to 3,000 sq ft	3	$625,000	$283	3 days

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 2 sales, closed at 103.7% of asking2 days

Reduced at least once 3 sales, closed at 97.6% of the reduced price42 days

Sellers who held their number went under contract in a median 2 days. Sellers who had to reduce took 42 days and still closed at 97.6% of their already reduced price, after a typical cut of $26,000.

Seller concessions

40%Of sales included a seller credit

$5,750Typical 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

Conventional 3 sales60%

Cash 2 sales40%

Cash was 40% 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 Winter 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 Winter Oaks in Winter Garden, Orange County, covering closed sales from 8 November 2025 through 3 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.