Winter Oaks

Winter Oaks is a community of single family homes in Winter Garden, Florida, with a range of options priced between $210,000 and $739,000. The smallest Winter Oaks home in the community is a two bedroom two bathroom residence that is 1,898 square feet (1,297SF Under Air living space), and the largest of the Winter Oaks homes has five beds and three baths and is a 3,874 square foot (3,102SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Winter Oaks range from $116 to $1,200. This fee includes grounds maintenance, the community pool, real estate taxes for common areas, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Winter Oaks home.

Winter Oaks amenities include a clubhouse, and swimming pool. There is also a community park, as well as a playground.

The Winter Oaks HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Winter Oaks - Orlando Executive (ORL), which is sixteen miles away; Orlando International (MCO), which is twenty miles away; Kissimmee Gateway (ISM), which is twenty one miles away, and Orlando Sanford International (SFB), which is twenty seven miles away from Winter Oaks.

Winter Oaks real estate activity on the Winter Garden MLS during the past year (as of March 2026) reflects four homes changing hands, with an average asking price of $641,000 and an average selling price of $632,219. This represents a healthy list-to-sell price ratio of 99% and $195 per square foot. During this period, Winter Oaks homes for sale have taken an average of just 24 days to sell.

In addition, there are numerous other communities in Winter Garden to choose from, or you may browse all available Winter Garden Real Estate, including some new construction opportunities. Homes for sale in Winter Oaks are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Winter Oaks hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

Winter Oaks Homes For Sale

SOLD 10/12/23

$529,900

MLS#MFRO6133645

728 Climbing Oaks Ct
Winter Garden, FL 34787

4

3

2

2,604 SqFt

0.14 Acres

SOLD 07/05/22

$499,000

MLS#MFRO6027341

722 Climbing Oaks Ct
Winter Garden, FL 34787

3

3

2

2,178 SqFt

0.14 Acres

SOLD 09/19/24

$500,000

$515,000

MLS#MFRO6227653

710 Climbing Oaks Ct
Winter Garden, FL 34787

3

3

2

2,402 SqFt

0.27 Acres

SOLD 09/30/14

$219,000

MLS#MFRO5315948

710 Climbing Oaks Ct
Winter Garden, FL 34787

3

3

2

2,402 SqFt

0.27 Acres

SOLD 01/12/26

$739,000

$749,000

MLS#MFRO6358505

627 Autumn Oaks Loop
Winter Garden, FL 34787

5

3

2

3,778 SqFt

0.17 Acres

SOLD 12/20/24

$544,900

MLS#MFRO6257937

930 Butter Oaks Ct
Winter Garden, FL 34787

4

3

2

2,739 SqFt

0.3 Acres

SOLD 05/02/22

$479,000

MLS#MFRO6013919

215 Autumn Oaks Loop
Winter Garden, FL 34787

4

3

2

2,868 SqFt

0.14 Acres

SOLD 05/31/22

$522,000

MLS#MFRO6019963

918 Butter Oaks Ct
Winter Garden, FL 34787

4

3

2

2,764 SqFt

0.16 Acres

SOLD 08/19/16

$362,000

$375,000

MLS#MFRO5447204

644 Autumn Oaks Loop
Winter Garden, FL 34787

5

3

2

3,874 SqFt

Pool

0.15 Acres

SOLD 06/24/16

$249,900

MLS#MFRO5438792

668 Autumn Oaks Loop
Winter Garden, FL 34787

3

2

2

2,153 SqFt

0.14 Acres

SOLD 12/02/22

$495,000

$560,000

MLS#MFRO6055707

208 Autumn Oaks Loop
Winter Garden, FL 34787

4

3

2

3,046 SqFt

0.13 Acres

SOLD 09/06/24

$498,002

$519,000

MLS#MFROM679529

662 Autumn Oaks Loop
Winter Garden, FL 34787

3

3

2

2,074 SqFt

0.14 Acres

SOLD 10/17/23

$555,000

$659,000

MLS#MFRO6134190

711 Climbing Oaks Ct
Winter Garden, FL 34787

4

3

2

3,608 SqFt

0.3 Acres

SOLD 09/25/23

$520,000

MLS#MFRO6134741

729 Climbing Oaks Ct
Winter Garden, FL 34787

4

2

2

2,613 SqFt

0.15 Acres

SOLD 06/21/22

$545,000

MLS#MFRO6026626

925 Butter Oaks Ct
Winter Garden, FL 34787

3

3

2

2,031 SqFt

0.14 Acres

SOLD 12/01/17

$330,000

MLS#MFRO5537838

913 Butter Oaks Ct
Winter Garden, FL 34787

3

3

2

2,682 SqFt

0.15 Acres

SOLD 12/02/22

$499,900

$560,000

MLS#MFRO6058464

880 Summer Oaks Rd
Winter Garden, FL 34787

4

3

2

2,952 SqFt

0.19 Acres

SOLD 03/24/25

$575,000

MLS#MFRS5119641

880 Summer Oaks Rd
Winter Garden, FL 34787

4

3

2

2,952 SqFt

0.19 Acres

SOLD 05/23/18

$324,999

MLS#MFRO5567454

868 Summer Oaks Rd
Winter Garden, FL 34787

4

3

2

2,996 SqFt

0.14 Acres

SOLD 01/19/22

$449,000

MLS#MFRO5987978

826 Summer Oaks Rd
Winter Garden, FL 34787

3

3

2

2,810 SqFt

0.14 Acres

SOLD 11/15/22

$499,000

MLS#MFRO6065832

874 Summer Oaks Rd
Winter Garden, FL 34787

3

2

2

2,202 SqFt

0.14 Acres

SOLD 11/07/23

$585,000

MLS#MFRG5074387

708 Canopy Oaks Ct
Winter Garden, FL 34787

4

3

2

2,844 SqFt

0.26 Acres

SOLD 03/20/15

$265,000

MLS#MFRO5343481

708 Canopy Oaks Ct
Winter Garden, FL 34787

3

3

2

2,844 SqFt

0.26 Acres

SOLD 10/30/24

$420,000

$445,000

MLS#MFRO6212141

908 Chapel Oaks Ct
Winter Garden, FL 34787

2

2

2

1,898 SqFt

0.14 Acres

---

We do not have any properties available for sale in Winter Oaks.

0 Active Listings in Winter Oaks