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MLS ID #O6329964
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  1. Home
  2. /Winter Park, FL
  3. /Windward Square
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Windward Square

Community constructed 1975-1980

BUILDINGS (OVER 5 UNITS)
Gallery0
BUILDINGS (2-5 UNITS)
Gallery7
SINGLE UNITS
Gallery159

About Windward Square

Windward Square is a residential community comprising a total of 173 units. The units feature a variety of bedroom types including 1-bedroom, 2-bedroom, and 3-bedroom layouts. The size of the units ranges from 988 to 1,016 square feet. The community consists of 159 single-unit buildings, enhancing the neighborhood's residential feel. Windward Square offers a comprehensive range of amenities, including a pool, fitness center, clubhouse, and various recreation facilities such as tennis courts and playgrounds. Additionally, residents can enjoy park areas, dog parks, and scenic trails for outdoor activities. With a pet-friendly policy that allows both cats and dogs, Windward Square provides a welcoming environment for pet owners. These thoughtful features contribute to a desirable living experience, blending comfort with active community living.

About Windward Square

Windward Square is a residential community comprising a total of 173 units. The units feature a variety of bedroom types including 1-bedroom, 2-bedroom, and 3-bedroom layouts. The size of the units ranges from 988 to 1,016 square feet. The community consists of 159 single-unit buildings, enhancing the neighborhood's residential feel. Windward Square offers a comprehensive range of amenities, including a pool, fitness center, clubhouse, and various recreation facilities such as tennis courts and playgrounds. Additionally, residents can enjoy park areas, dog parks, and scenic trails for outdoor activities. With a pet-friendly policy that allows both cats and dogs, Windward Square provides a welcoming environment for pet owners. These thoughtful features contribute to a desirable living experience, blending comfort with active community living.
Community ImageView Listing
MLS ID #O6329964
Community ImagesMLS ID #O6329964
Community ImagesMLS ID #O6325914
Community ImagesMLS ID #O6315951

Windward Square Market Stats Last 12 months

AVG. LISTED PRICE$273,722($244 /sqft.)

AVG. SALE PRICE$273,773($254 /sqft.)
YEAR OVER YEAR LIST PRICE0.00%

YEAR OVER YEAR SALE PRICE0.00%
TOTAL LISTINGS15 Listed

TOTAL SOLD19 Sold
AVERAGE DAYS ON MARKET80 days
AVERAGE HOA FEES PER SQFT$13 /monthly

Market StatsLast 12 months

AVG. LISTED PRICE
$273,722($244 /sqft.)

AVG. SALE PRICE
$273,773($254 /sqft.)
YEAR OVER YEAR LIST PRICE0.00%

YEAR OVER YEAR SALE PRICE0.00%
TOTAL LISTINGS15 Listed

TOTAL SOLD19 Sold
AVERAGE DAYS ON MARKET80 days
AVERAGE HOA FEES PER SQFT$13 /monthly

Windward Square Amenities

Fitness Center
Fitness Center
Pool
Pool
Security
Security
Fire Alarm
Fire Alarm
Security System
Security System
Tennis Court(s)
Tennis Court(s)
Spa/Hot Tub
Spa/Hot Tub
Clubhouse
Clubhouse
Storage
Storage
Balcony
Balcony
Smoke Detector(s)
Smoke Detector(s)
Fitness Center
Fitness Center
Pool
Pool
Security
Security
Fire Alarm
Fire Alarm
Security System
Security System

Amenities

Fitness Center
Fitness Center
Pool
Pool
Security
Security
Fire Alarm
Fire Alarm
Security System
Security System
Tennis Court(s)
Tennis Court(s)
Spa/Hot Tub
Spa/Hot Tub
Clubhouse
Clubhouse
Storage
Storage
Balcony
Balcony
Smoke Detector(s)
Smoke Detector(s)

Windward Square Policies

Pets allowed
Pets not allowed
BBQ allowed
BBQ not allowed
Sublet allowed
Sublet not allowed
Short term rental not allowed
Short term rental not allowed

The Neighborhood:

Frequently Asked Questions About Windward Square

How many buildings are there in Windward Square?

Windward Square has a total of 166 buildings: 7 buildings with 2 to 5 units and 159 buildings with single unit properties.

How much does property typically cost in Windward Square?

In Windward Square, the average sales price is $273,773 and the average listed price is $273,722.

What amenities can I expect in buildings in Windward Square?

Buildings in Windward Square include amenities like Club House, Trail(s), Pool, Dog Park, Fitness Center, Park, Playground, and Tennis Court(s).

What is the average HOA fee in buildings in Windward Square?

The average HOA fee in Windward Square is $13.

What is the parking situation like in Windward Square buildings?

Parking features in Windward Square include Rv/Boat Parking and Parking Pad.
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  1. Home
  2. /Winter Park, FL
  3. /Windward Square
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