Windermere Crossing

Windermere Crossing is a gated community of single family homes in Winter Garden, Florida, with a range of options priced between $319,900 and $1,049,000. The smallest Windermere Crossing home in the community is a three bedroom three bathroom residence that is 3,062 square feet (2,508SF Under Air living space), and the largest of the Windermere Crossing homes has six beds and four baths and is a 4,844 square foot (3,909SF 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 Windermere Crossing range from $100 to $760. This fee includes grounds maintenance, maintaining the community roads, security, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Windermere Crossing home.

The Windermere Crossing HOA rules do allow homeowners to have pets although there are certain breed restrictions. Dogs and cats are allowed.

There are four commercial airports that serve Windermere Crossing - Orlando Executive (ORL), which is fourteen miles away; Orlando International (MCO), which is seventeen miles away; Kissimmee Gateway (ISM), which is eighteen miles away, and Orlando Sanford International (SFB), which is twenty six miles away from Windermere Crossing.

Windermere Crossing real estate activity on the Winter Garden MLS during the past year (as of February 2026) reflects three homes changing hands, with an average asking price of $772,967 and an average selling price of $745,000. This represents a healthy list-to-sell price ratio of 96% and $168 per square foot. During this period, Windermere Crossing homes for sale have taken an average of 150 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 Windermere Crossing are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Windermere Crossing 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.

Windermere Crossing Homes For Sale

SOLD 02/02/26

$819,900

$884,900

MLS#MFRO6345657

1061 Spring Mill Dr
Winter Garden, FL 34787

5

3

2

4,404 SqFt

Pool

0.34 Acres

SOLD 04/05/23

$720,000

MLS#MFRG5066036

12227 Rebeccas Run Dr
Winter Garden, FL 34787

3

3

3

3,707 SqFt

Pool

0.29 Acres

SOLD 08/22/23

$899,900

MLS#MFRO6124521

12155 Rebeccas Run Dr
Winter Garden, FL 34787

4

3

3

4,451 SqFt

Pool

Water Front

0.66 Acres

SOLD 04/18/14

$400,000

MLS#MFRO5206631

12065 Rebeccas Run Dr
Winter Garden, FL 34787

5

4

3

4,398 SqFt

Pool

0.33 Acres

SOLD 08/29/22

$625,000

MLS#MFRO6039601

12188 Windermere Crossing Cir
Winter Garden, FL 34787

4

3

2

3,107 SqFt

Pool

0.33 Acres

SOLD 04/10/18

$434,900

MLS#MFRO5561036

12170 Windermere Crossing Cir
Winter Garden, FL 34787

4

3

2

3,653 SqFt

Pool

0.34 Acres

SOLD 05/17/24

$1,049,000

$1,100,000

MLS#MFRU8233274

12146 Windermere Crossing Cir
Winter Garden, FL 34787

5

3

3

4,458 SqFt

Pool

Water Front

0.82 Acres

SOLD 08/27/25

$700,000

$760,000

MLS#MFRO6307794

12411 Scarlett Sage Ct
Winter Garden, FL 34787

4

3

3

4,469 SqFt

Pool

0.26 Acres

SOLD 09/27/21

$750,000

MLS#MFRJ935541

12134 Windermere Crossing Cir
Winter Garden, FL 34787

5

3

3

3,324 SqFt

Pool

Water Front

0.79 Acres

SOLD 08/01/17

$409,000

MLS#MFRO5515568

1156 English Garden Ln
Winter Garden, FL 34787

4

3

2

3,083 SqFt

Pool

0.25 Acres

SOLD 11/18/24

$879,900

MLS#MFRO6243280

1132 English Garden Ln
Winter Garden, FL 34787

5

4

3

4,844 SqFt

Pool

0.35 Acres

SOLD 08/17/23

$725,000

$785,000

MLS#MFRO6113509

12441 Scarlett Sage Ct
Winter Garden, FL 34787

6

4

3

4,033 SqFt

Pool

0.25 Acres

SOLD 08/15/24

$599,900

$675,000

MLS#MFRO6149580

12447 Scarlett Sage Ct
Winter Garden, FL 34787

5

3

3

3,737 SqFt

0.25 Acres

SOLD 05/30/23

$649,900

$660,000

MLS#MFRO6100965

1149 English Garden Ln
Winter Garden, FL 34787

4

3

2

3,469 SqFt

0.31 Acres

SOLD 06/13/17

$375,000

$410,000

MLS#MFRO5490391

12453 Scarlett Sage Ct
Winter Garden, FL 34787

4

3

2

3,107 SqFt

Pool

0.25 Acres

SOLD 05/21/18

$395,000

$415,000

MLS#MFRO5545053

12513 Scarlett Sage Ct
Winter Garden, FL 34787

5

3

3

4,451 SqFt

0.25 Acres

SOLD 11/07/14

$349,000

$399,900

MLS#MFRO5309072

12513 Scarlett Sage Ct
Winter Garden, FL 34787

5

3

3

3,570 SqFt

25 Acres

SOLD 12/12/14

$425,000

MLS#MFRO5326692

1107 English Garden Ln
Winter Garden, FL 34787

5

4

3

3,817 SqFt

Pool

0.3 Acres

SOLD 08/05/22

$750,000

MLS#MFRO6043359

12020 Windermere Crossing Cir
Winter Garden, FL 34787

4

3

3

4,588 SqFt

Pool

0.3 Acres

SOLD 10/07/25

$799,000

$880,000

MLS#MFRA4649856

1125 English Garden Ln
Winter Garden, FL 34787

5

4

2

4,417 SqFt

Pool

0.35 Acres

SOLD 07/25/13

$319,900

MLS#MFRO5166973

12019 Windermere Crossing Cir
Winter Garden, FL 34787

4

3

2

3,062 SqFt

Pool

0.24 Acres

SOLD 05/15/24

$795,000

MLS#MFRO6176518

12061 Windermere Crossing Cir
Winter Garden, FL 34787

4

3

2

3,563 SqFt

Pool

0.35 Acres

SOLD 11/09/21

$525,000

MLS#MFRO5977271

12086 Windermere Crossing Cir
Winter Garden, FL 34787

4

3

3

3,279 SqFt

Pool

0.29 Acres

SOLD 01/21/15

$424,900

$480,000

MLS#MFRO5201410

12080 Windermere Crossing Cir
Winter Garden, FL 34787

5

5

3

4,762 SqFt

Pool

0.29 Acres

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We do not have any properties available for sale in Windermere Crossing.

0 Active Listings in Windermere Crossing