Overlook Estates

Overlook Estates is a gated community of single family homes, and townhomes in Winter Haven, Florida, with a range of options priced between $104,900 and $524,900. The smallest Overlook Estates home in the community is a three bedroom one bathroom residence that is 1,556 square feet (1,260SF Under Air living space), and the largest of the Overlook Estates homes has five beds and four baths and is a 4,216 square foot (3,306SF Under Air) residence.

Property management fees in Polk County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Overlook Estates range from $66 to $550 and $550 for a townhome. This fee includes grounds maintenance, and maintaining the community roads. Please check the individual listing pages for the exact homeowners association fees for a particular Overlook Estates home.

The Overlook Estates HOA rules do allow homeowners to have pets. There is a limitation on pet size. Dogs and cats are allowed.

There are four commercial airports that serve Overlook Estates - Lakeland Linder International (LAL), which is twenty miles away; Kissimmee Gateway (ISM), which is twenty five miles away; Orlando International (MCO), which is 37 miles away, and Orlando Executive (ORL), which is 43 miles away from Overlook Estates.

Overlook Estates real estate activity on the Winter Haven MLS during the past year (as of September 2025) reflects three homes changing hands, with an average asking price of $418,933 and an average selling price of $417,333. This represents a healthy list-to-sell price ratio of 100% and $138 per square foot. During this period, Overlook Estates homes for sale have taken an average of 34 days to sell.

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

Overlook Estates Homes For Sale

SOLD 09/10/22

$383,310

MLS#MFRT3378740

1311 Donatello Ln
Winter Haven, FL 33884

4

2

2

1,850 SqFt

0.19 Acres

New Construction

SOLD 08/31/22

$410,950

MLS#MFRT3378786

1030 Michelangelo Ln
Winter Haven, FL 33884

4

2

2

1,850 SqFt

0.23 Acres

New Construction

SOLD 08/12/22

$387,690

MLS#MFRT3378594

1021 Michelangelo Ln
Winter Haven, FL 33884

4

2

2

1,850 SqFt

0.29 Acres

New Construction

SOLD 07/12/23

$398,550

$460,130

MLS#MFRT3378728

1213 Michelangelo Ln
Winter Haven, FL 33884

4

2

2

2,894 SqFt

0.19 Acres

New Construction

SOLD 01/20/23

$364,290

$442,090

MLS#MFRT3378618

1026 Michelangelo Ln
Winter Haven, FL 33884

5

3

2

2,386 SqFt

0.23 Acres

New Construction

SOLD 10/07/22

$425,790

MLS#MFRT3378636

1315 Donatello Ln
Winter Haven, FL 33884

5

3

2

2,386 SqFt

0.19 Acres

New Construction

SOLD 08/22/22

$425,000

MLS#MFRP4921957

250 Santa Rosa Dr
Winter Haven, FL 33884

3

4

2

3,646 SqFt

Pool

0.44 Acres

SOLD 02/01/23

$475,000

$500,000

MLS#MFRP4922793

261 Santa Rosa Dr
Winter Haven, FL 33884

5

3

2

3,000 SqFt

Pool

0.35 Acres

SOLD 10/27/22

$449,000

MLS#MFRP4922788

223 Santa Rosa Dr
Winter Haven, FL 33884

4

2

2

2,314 SqFt

Pool

0.32 Acres

SOLD 10/21/22

$350,000

$385,000

MLS#MFRL4932942

278 Santa Rosa Dr
Winter Haven, FL 33884

3

3

2

2,746 SqFt

Pool

0.32 Acres

SOLD 01/13/23

$385,000

MLS#MFRP4923615

249 Santa Rosa Dr
Winter Haven, FL 33884

3

2

2

2,600 SqFt

Pool

0.28 Acres

SOLD 10/04/21

$310,000

$315,000

MLS#MFRL4924466

230 Santa Rosa Dr
Winter Haven, FL 33884

3

2

2

2,185 SqFt

0.3 Acres

SOLD 08/14/23

$386,900

MLS#MFRP4926251

232 Santa Rosa Dr
Winter Haven, FL 33884

4

3

2

3,270 SqFt

0.3 Acres

SOLD 08/31/23

$420,000

MLS#MFRL4938646

716 Santa Maria Dr
Winter Haven, FL 33884

3

2

2

2,938 SqFt

Pool

Water Front

0.33 Acres

SOLD 03/13/24

$394,000

$415,000

MLS#MFRO6140428

739 Santa Maria Dr
Winter Haven, FL 33884

3

2

2

2,405 SqFt

Pool

0.24 Acres

SOLD 11/17/23

$524,900

$575,000

MLS#MFRL4937657

261 Santa Rosa Dr
Winter Haven, FL 33884

5

3

2

3,693 SqFt

Pool

0.35 Acres

SOLD 11/17/23

$489,000

$499,900

MLS#MFRP4927766

718 Santa Maria Dr
Winter Haven, FL 33884

4

2

2

3,384 SqFt

Pool

0.49 Acres

SOLD 02/07/24

$375,000

$400,000

MLS#MFRGC517627

351 Overlook Dr Se
Winter Haven, FL 33884

3

2

2

2.13 Acres

SOLD 04/18/24

$450,000

$469,000

MLS#MFRL4941822

240 Santa Rosa Dr
Winter Haven, FL 33884

4

3

2

4,216 SqFt

Pool

0.28 Acres

SOLD 08/16/24

$445,000

MLS#MFRT3522014

234 Santa Rosa Dr
Winter Haven, FL 33884

4

3

2

2,892 SqFt

Pool

0.49 Acres

SOLD 08/30/24

$364,900

$386,000

MLS#MFRP4930318

125 Waldemar Ct Se
Winter Haven, FL 33884

4

2

2

3,025 SqFt

0.37 Acres

SOLD 04/28/15

$199,999

$215,000

MLS#MFRP4701949

205 Santa Rosa Dr
Winter Haven, FL 33884

3

2

2

2,841 SqFt

Pool

0.38 Acres

SOLD 07/10/15

$214,900

$224,900

MLS#MFRP4704192

238 Santa Rosa Dr
Winter Haven, FL 33884

4

3

2

3,669 SqFt

0.35 Acres

SOLD 09/04/15

$199,900

MLS#MFRP4705642

244 Santa Rosa Dr
Winter Haven, FL 33884

4

2

2

3,320 SqFt

0.32 Acres

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We do not have any properties available for sale in Overlook Estates.

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