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modified
5+ Days Ago

Location

Antilles Dr, Winter Park, FL 32792, USA

Floor plans

2 bed2 bed1 bath900 sqft

Available rentals nearby

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Perla Gem Lake

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Baldwin Park • 4460 Lower Park Rd

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$2,513–$3,077

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Marvera Casselberry

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3851 Grandpine Way

2 Beds

$1,901–$2,107

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Mizell at Winter Park

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600 N Semoran Blvd

2 Beds

$1,470

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Sovereignty at Winter Park

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7745 Brandywood Cir

2 Beds

$1,465–$1,745

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Sun Bay Apartments

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Goldenrod • 7001 Aloma Avenue

2 Beds

$1,500–$1,525

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Colonial Pointe

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2300 Econ Cir

2 Beds

$1,628–$1,758

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The Park at Rialto

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2174 Sharp Ct

2 Beds

$1,399–$1,559

featured image of 100 Boucle Jeanne Cir

Perla Gem Lake

Our team has verified this company

100 Boucle Jeanne Cir

2 Beds

$2,742–$3,513

featured image of 4460 Lower Park Rd

Azul Baldwin Park

Our team has verified this company

Baldwin Park • 4460 Lower Park Rd

2 Beds

$2,513–$3,077

featured image of 3851 Grandpine Way

Marvera Casselberry

Our team has verified this company

3851 Grandpine Way

2 Beds

$1,901–$2,107

featured image of 600 N Semoran Blvd

Mizell at Winter Park

Our team has verified this company

600 N Semoran Blvd

2 Beds

$1,470

featured image of 7745 Brandywood Cir

Sovereignty at Winter Park

Our team has verified this company

7745 Brandywood Cir

2 Beds

$1,465–$1,745

featured image of 7001 Aloma Avenue

Sun Bay Apartments

Our team has verified this company

Goldenrod • 7001 Aloma Avenue

2 Beds

$1,500–$1,525

featured image of 2300 Econ Cir

Colonial Pointe

Our team has verified this company

2300 Econ Cir

2 Beds

$1,628–$1,758

featured image of 2174 Sharp Ct

The Park at Rialto

Our team has verified this company

2174 Sharp Ct

2 Beds

$1,399–$1,559

Rent trends in Winter Park

Median rents as of Apr 4 2026.
Winter Park
A table of studio rental data trends in Winter Park
MonthMedian Rent
June 2024$1,050
July 2024$1,050
August 2024$1,050
September 2024$1,050
October 2024$1,050
November 2024$1,126
March 2025$1,519
April 2025$1,519
May 2025$1,200
June 2025$1,200
July 2025$1,290
August 2025$1,378
September 2025$1,299
October 2025$1,241
November 2025$1,235
December 2025$1,229
January 2026$1,224
February 2026$1,224
March 2026$1,224
April 2026$1,224

Schools near Windward Square

Eastbrook Elementary School

5525 tangerine ave

winter park, FL, 32792

PK, K-5Public
B+

Audubon Park School

1500 falcon dr

orlando, FL, 32803

PK, K-8Public
A-

Longwood Elementary School

840 orange ave

longwood, FL, 32750

PK, K-5Public
A-

Orange County Virtual School

1600 silver star rd

orlando, FL, 32804

K-12Public

90-K8-N-7

445 w amelia st

orlando, FL, 32801

PK, K-8Public
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Internet available near Windward Square

Neighborhood

NEIGHBORHOOD VIBE
Peaceful and quiet
Noise-canceling headphones not required in this mostly noise free area.

Getting around Winter Park near Antilles Dr

Walking

4/10
Some shops and stores are within a few minutes.

Driving

8/10
This area is close to freeways and has adequate parking options.

Cycling

4/10
More spots are within biking distance and some roads are cyclist-friendly.

Transit

1/10
FYI, there are little to no public transit options within walking distance.

Points of interest for Antilles Dr, Winter Park

Groceries

1/10
Closest supermarket further than a 30-minute walk

Shopping

4/10
Some shops within walking distance

Cafes

4/10
Some cafés within a few minutes’ walk

Restaurants

4/10
Some restaurants within a few minutes’ walk

Primary schools

7/10
At least one elementary school within a 15-minute walk

High schools

7/10
At least one high school within a 15-minute walk

Parks

4/10
Limited amount of park space nearby

Nightlife

2/10
Few or no bars within walking distance

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