Hamiltons Reserve

Hamiltons Reserve is a community of single family homes in Kissimmee, Florida, with a range of options priced between $114,500 and $549,950. The smallest Hamiltons Reserve home in the community is a three bedroom two bathroom residence that is 1,300 square feet (1,233SF Under Air living space), and the largest of the Hamiltons Reserve homes has six beds and three baths and is a 3,750 square foot (3,045SF Under Air) residence.

Property management fees in Osceola County vary depending on the community and the subdivision within the community and sometimes vary between homes in the subdivision. The current HOA fees for homes in Hamiltons Reserve range from $26 to $430. This fee includes common area maintenance, grounds maintenance, building 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 Hamiltons Reserve home.

Hamiltons Reserve amenities include a swimming pool. Sports facilities include tennis courts.

The Hamiltons Reserve Master HOA does allow pets, however the various subdivision may impose their own pet restrictions, so check the individual listings for specifics.

There are three subdivisions within the Hamiltons Reserve community, they are: Baypointe 1, Baypointe 2, and Wilshire Oaks.

There are four commercial airports that serve Hamiltons Reserve - Kissimmee Gateway (ISM), which is three miles away; Orlando International (MCO), which is thirteen miles away; Orlando Executive (ORL), which is eighteen miles away, and Orlando Sanford International (SFB), which is 35 miles away from Hamiltons Reserve.

Hamiltons Reserve real estate activity on the Kissimmee MLS during the past year (as of November 2025) reflects eight homes changing hands, with an average asking price of $430,281 and an average selling price of $409,250. This represents a healthy list-to-sell price ratio of 95% and $180 per square foot. During this period, Hamiltons Reserve homes for sale have taken an average of 58 days to sell.

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

Hamiltons Reserve Homes For Sale

SOLD 09/12/16

$235,000

$245,000

Wilshire Oaks

2302 Rochelle Ave
Kissimmee, FL 34746

5

3

2

3,610 SqFt

0.63 Acres

SOLD 03/26/24

$458,000

$495,000

Wilshire Oaks

2338 Chadwick Cir
Kissimmee, FL 34746

5

4

2

3,014 SqFt

Pool

0.34 Acres

SOLD 01/23/23

$499,990

Wilshire Oaks

2307 Rochelle Ave
Kissimmee, FL 34746

5

4

2

3,750 SqFt

Pool

0.29 Acres

SOLD 02/20/25

$449,900

Wilshire Oaks

2341 Chadwick Cir
Kissimmee, FL 34746

4

3

2

2,628 SqFt

Pool

0.24 Acres

SOLD 03/14/17

$310,000

Wilshire Oaks

2348 Chadwick Cir
Kissimmee, FL 34746

6

3

2

3,159 SqFt

Pool

0.35 Acres

SOLD 09/30/14

$219,000

$225,000

Wilshire Oaks

2330 Chadwick Cir
Kissimmee, FL 34746

4

3

2

3,036 SqFt

Pool

0.29 Acres

SOLD 03/31/25

$470,000

Baypointe 1

2410 Berkshire Ct
Kissimmee, FL 34746

3

3

2

2,706 SqFt

Pool

0.14 Acres

SOLD 01/30/23

$399,950

Baypointe 1

4901 Dunmore Ln
Kissimmee, FL 34746

4

3

2

2,401 SqFt

Pool

0.22 Acres

SOLD 05/01/25

$479,999

$5,199,000

Wilshire Oaks

2350 Chadwick Cir
Kissimmee, FL 34746

5

4

2

3,041 SqFt

Pool

0.43 Acres

SOLD 03/10/16

$259,000

$269,000

Wilshire Oaks

2350 Chadwick Cir
Kissimmee, FL 34746

5

4

2

3,493 SqFt

Pool

0.43 Acres

SOLD 10/27/23

$364,900

$369,900

Baypointe 1

2418 Berkshire Ct
Kissimmee, FL 34746

3

2

2

2,002 SqFt

0.13 Acres

SOLD 06/27/22

$389,000

Baypointe 1

2415 Berkshire Ct
Kissimmee, FL 34746

3

2

2

2,002 SqFt

Pool

0.16 Acres

SOLD 08/22/24

$395,000

$410,000

Baypointe 1

4904 Dunmore Ln
Kissimmee, FL 34746

4

2

2

2,259 SqFt

0.14 Acres

SOLD 09/02/25

$549,950

Wilshire Oaks

2356 Chadwick Cir
Kissimmee, FL 34746

5

3

2

3,049 SqFt

Pool

Water Front

0.45 Acres

SOLD 10/22/21

$344,900

Baypointe 1

4906 Dunmore Ln
Kissimmee, FL 34746

4

3

2

2,219 SqFt

Pool

0.16 Acres

SOLD 01/09/17

$175,000

Baypointe 1

2419 Berkshire Ct
Kissimmee, FL 34746

3

2

2

2,002 SqFt

Pool

0.18 Acres

SOLD 07/30/24

$348,000

$375,000

Baypointe 1

2419 Berkshire Ct
Kissimmee, FL 34746

3

2

1

2,002 SqFt

Pool

0.18 Acres

SOLD 01/09/23

$425,000

Baypointe 1

4805 Huxley Ct
Kissimmee, FL 34746

4

4

2

2,706 SqFt

Pool

0.18 Acres

SOLD 04/26/13

$145,000

Baypointe 1

4804 Huxley Ct
Kissimmee, FL 34746

4

3

2

2,568 SqFt

Pool

0.2 Acres

SOLD 01/15/22

$339,900

$369,900

Baypointe 1

4947 Dunmore Ln
Kissimmee, FL 34746

4

3

2

2,075 SqFt

Pool

0.13 Acres

SOLD 09/13/24

$420,000

Baypointe 1

4935 Dunmore Ln
Kissimmee, FL 34746

4

3

2

2,075 SqFt

Pool

0.13 Acres

SOLD 03/31/25

$383,000

$385,000

Baypointe 1

4929 Dunmore Ln
Kissimmee, FL 34746

3

2

2

1,542 SqFt

Pool

0.13 Acres

SOLD 05/02/22

$492,000

Baypointe 1

4909 Tennyson Ct
Kissimmee, FL 34746

4

3

2

2,568 SqFt

Pool

0.19 Acres

SOLD 08/30/24

$385,000

Baypointe 2

2518 Davenport Cir
Kissimmee, FL 34746

3

2

1

1,668 SqFt

Pool

0.15 Acres

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