HeaderIcon
  1. Agent Logo
Search Nearby
Add to favoritesAdd to favorites (hover)
Save
Community Image
Gallery22
MLS ID #O6329523
Search Nearby
  1. Home/
  2. Winter Park, FL/
  3. Windward Square
Add to favoritesAdd to favorites (hover)
Save

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 #O6329523
Community ImagesMLS ID #O6329523
Community ImagesMLS ID #O6329523
Community ImagesMLS ID #O6329964

Windward Square Market Stats Last 12 months

AVG. LISTED PRICE$283,509($239 /sqft.)
AVG. SALE PRICE$275,860($243 /sqft.)
YEAR OVER YEAR LIST PRICE0.00%
YEAR OVER YEAR SALE PRICE0.00%
TOTAL LISTINGS3 Listed
TOTAL SOLD3 Sold
AVERAGE DAYS ON MARKET83 days
AVERAGE HOA FEES PER SQFT$14 /monthly

Market StatsLast 12 months

AVG. LISTED PRICE
$283,509($239 /sqft.)
AVG. SALE PRICE
$275,860($243 /sqft.)
YEAR OVER YEAR LIST PRICE0.00%
YEAR OVER YEAR SALE PRICE0.00%
TOTAL LISTINGS3 Listed
TOTAL SOLD3 Sold
AVERAGE DAYS ON MARKET83 days
AVERAGE HOA FEES PER SQFT$14 /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, including 7 buildings with 2 to 5 units and 159 single unit properties.

How much does property typically cost in Windward Square?

In Windward Square, the average sales price is $275,860, and the average listed price is $283,509.

What amenities can I expect in buildings in Windward Square?

Buildings in Windward Square include amenities like Tennis Court(s), Pool, Sidewalks, Shuffleboard Court, Playground, Dog Park, Club House, Spa/Hot Tub, Trail(s), Recreation Facilities, Community Mailbox, Irrigation, Park, Fitness Center, and Wheelchair Access.

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

The average HOA fee in Windward Square is $14.

What is the parking situation like in Windward Square buildings?

Parking data for Windward Square includes features such as Rv/Boat Parking and Parking Pad.
Get the HelloCondo Newsletter
Real-estate tips, insights, and market reports in your inbox.
Newsletter
  1. Home/
  2. Winter Park, FL/
  3. Windward Square
Condo Markets
Apopka
Astor
Belleair Beach
Clearwater Beach
Crystal Beach
Eustis
Holiday
Indian Rocks Beach
Intercession City
Lady Lake
Lithia
New Port Richey
Nobleton
Port Richey
Saint Cloud
Saint Petersburg
Sorrento
Tampa
Wimauma
Winter Garden
Buildings
1000 Lake Of The Woods Blvd
11 Escondido Cir
125 S Interlachen Ave
1674 Lakemont Ave Ave
1910 Summer Club Dr
1939 Summer Club Dr
2404 Gallery View Dr
300 Lakepointe Dr
3026 Antique Oaks Cir
305 Lakepointe Dr
345 Forestway Cir
364 Northpointe Ct
375 Lakepointe Dr
385 Woodside Dr
400 Lake Placid Ct
420 Forestway Cir
504 Orange Dr
538 Orange Dr
725 Northlake Blvd
953 Courtyard Ln
Neighborhoods
Audubon ParkChampionsGateChristmas
Colonial Town CenterCypress WoodsDover Shores EastFells LandingHeathrowLake Davis / GreenwoodLockhartLorna DooneMalibu GrovesMercy DriveMilleniaOak RidgePine HillsPreserve at Lake MonroeSavannah ParkSeaboard IndustrialSeminole Heights
ZIP Codes
327073271432765
3276632779328033281732818328263283032831328323283632839347293473434736347443476934788
Community
Acorn Village CondominiumsAdair CondominiumsAloma
Aloma ParkAltamonte HeightsAltamonte VillageAntigua BayArborview ParkAshford Park TownhomesAtha Urban Flats CondominiumsAtherton Park CondominiumsAzalea Lane CondominiumsBarclay Reserve TownhomesBaytree SectionBaytree VillageBiltmore TownhomesBona VistaBradford CoveBraewick at TuscawillaBranch Tree
Popular Searches
Condos in Winter Park
Condos with Pool in Winter Park
Condos with Pets allowed in Winter Park
Condos Near Water in Winter Park
Condos with EV Parking in Winter Park
Condos with Water View in Winter Park
Condos around $200,000 in Winter Park
Condos around $300,000 in Winter Park
Condos around $400,000 in Winter Park
Condos around $500,000 in Winter Park
Condos around $600,000 in Winter Park
Condos around $700,000 in Winter Park
Condos around $800,000 in Winter Park
Condos around $900,000 in Winter Park
Condos around $1,000,000 in Winter Park
Condos over $1,050,000 in Winter Park
HelloCondo Logo
LocationIcon
HelloCondo Is The #1 Condo Search Platform And Real Estate Recommendation Engine. Search, Find And Buy The Perfect Condo And Get Matched With The Best Agents. Finding A Condo Has Never Been So Easy.

HelloCondo is a division of HelloCasa, LLC

FacebookIconInstagramIconXIconRedditIcon
HelloCondo
Find A RealtorTerms of UsePrivacy PolicyCalifornia Privacy NoticeAccessibility PolicyCCPA Notice on CollectionDMCANYS Standard Operating ProcedureNYS Fair Housing Notice
Contact
LocationIcon
300 Galleria Pkwy SE, Suite 1500,
Atlanta, GA 30339
PhoneICon
(855) 625-0319
EmailIConhello@hellocondo.com
Contact Us
For Sale
Condos for saleTownhomes for sale
AgentIcon
LocationIcon

Julie's Realty, LLC

Yuliya "Julie" Sidorevskaya

1700 79th Street CSWY STE#160,

North Bay VIllage, FL, 33141

PhoneICon
305-340-1857
EmailIConJulie@JuliesRealty.net
© HelloCondo 2025. All Rights Reserved.