Winters Landing

Winters Landing is a community of single family homes in Oakland, Florida, with a range of options priced between $318,000 and $875,000. The smallest Winters Landing home in the community is a three bedroom two bathroom residence that is 3,234 square feet (2,420SF Under Air living space), and the largest of the Winters Landing homes has five beds and four baths and is a 4,533 square foot (3,448SF 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 Winters Landing range from $50 to $550. Please check the individual listing pages for the exact homeowners association fees for a particular Winters Landing home.

The Winters Landing HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Winters Landing - Orlando Executive (ORL), which is eighteen miles away; Orlando International (MCO), which is twenty one miles away; Kissimmee Gateway (ISM), which is twenty two miles away, and Orlando Sanford International (SFB), which is twenty eight miles away from Winters Landing.

Winters Landing real estate activity on the Oakland MLS during the past year (as of October 2025) reflects that just one home changed hands during this time. Offered with an asking price of $875,000 and selling for $840,000, this represents a list/sell ratio of 96%. It took 66 days from the time it was listed until it sold.

In addition, there are numerous other communities in Oakland to choose from, or you may browse all available Oakland Real Estate, including some new construction opportunities. Homes for sale in Winters Landing are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Winters Landing 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.

Winters Landing Homes For Sale

SOLD 05/15/24

$765,000

$798,595

MLS#MFRO6165594

607 E Oakland Ave
Winter Garden, FL 34787

4

4

3

3,406 SqFt

Pool

0.36 Acres

SOLD 05/11/24

$799,900

MLS#MFRO6191791

501 E Oakland Ave
Oakland, FL 34787

4

4

3

4,235 SqFt

Pool

0.34 Acres

SOLD 02/15/24

$599,000

MLS#MFRO6155099

505 E Oakland Ave
Oakland, FL 34787

4

3

3

3,445 SqFt

0.4 Acres

SOLD 04/04/17

$434,900

$439,900

MLS#MFRO5489547

607 E Oakland Ave
Oakland, FL 34787

4

4

3

4,350 SqFt

Pool

0.36 Acres

SOLD 10/05/21

$565,000

MLS#MFRO5963632

4 Winters Landing Dr
Oakland, FL 34787

4

3

3

4,476 SqFt

0.36 Acres

SOLD 08/12/23

$630,000

$650,000

MLS#MFRG5067445

506 E Henschen Ave
Oakland, FL 34787

4

4

2

4,448 SqFt

0.35 Acres

SOLD 02/16/18

$429,000

$439,900

MLS#MFRO5548148

507 E Henschen Ave
Oakland, FL 34787

4

3

3

3,810 SqFt

Pool

0.29 Acres

SOLD 07/15/15

$318,000

MLS#MFRT2755473

506 E Gulley Ave
Oakland, FL 34787

4

3

3

3,695 SqFt

0.29 Acres

SOLD 12/07/15

$374,900

$425,000

MLS#MFRG4814559

505 E Gulley Ave
Oakland, FL 34787

4

4

3

4,257 SqFt

Pool

0.3 Acres

SOLD 12/31/13

$349,000

$369,000

MLS#MFRO5177598

500 Macchi. Ave
Winter Garden, FL 34787

4

4

3

4,298 SqFt

0.3 Acres

SOLD 12/27/16

$339,400

MLS#MFRG4834668

414 Macchi Ave
Oakland, FL 34787

3

3

3

3,234 SqFt

0.3 Acres

SOLD 11/24/14

$425,900

MLS#MFRO5317302

415 Macchi Ave
Oakland, FL 34787

4

4

2

4,533 SqFt

Pool

0.34 Acres

SOLD 07/11/23

$799,900

MLS#MFRO6117313

415 Macchi Ave
Winter Garden, FL 34787

4

4

2

4,533 SqFt

Pool

0.34 Acres

SOLD 06/29/17

$440,000

MLS#MFRO5514197

405 Macchi Ave
Oakland, FL 34787

4

4

3

4,459 SqFt

Pool

0.29 Acres

SOLD 05/16/17

$429,000

$449,500

MLS#MFRO5498601

407 Macchi Ave
Oakland, FL 34787

5

4

3

4,333 SqFt

Pool

0.29 Acres

SOLD 08/11/22

$550,000

MLS#MFRO6041042

401 Macchi Ave
Oakland, FL 34787

3

2

3

2,862 SqFt

0.29 Acres

SOLD 08/29/25

$875,000

$899,000

MLS#MFRO6298650

413 Macchi Ave
Oakland, FL 34787

4

3

3

4,353 SqFt

0.29 Acres

SOLD 12/01/22

$565,000

MLS#MFRO6067391

501 Macchi Ave
Oakland, FL 34787

3

2

2

2,537 SqFt

0.34 Acres

SOLD 11/17/22

$725,000

MLS#MFRO6063389

409 Macchi Ave
Oakland, FL 34787

4

3

3

3,317 SqFt

Pool

0.29 Acres

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We do not have any properties available for sale in Winters Landing.

0 Active Listings in Winters Landing