Neighborhood · Winter Park, Florida
Windward Square
An affordable foothold in Winter Park's orbit
3
Homes for sale
$275,000
Median list price
$177
Avg price / sqft
30
Median days on market
Windward Square sits in Winter Park's practical middle — a quiet Orange County pocket of modest, well-kept homes where a smaller footprint buys you real proximity to everything Central Florida offers. Downtown Orlando is about 24 minutes out, MCO airport roughly 32, and you're within easy reach of neighboring communities like Lake Killarney, Winter Park Pines, and the walkable energy of Hannibal Square. It's the kind of place that appeals to buyers who want the address without the Park Avenue price tag.
For a buyer today, this is one of the more attainable entries into Winter Park homes for sale. With just 3 active listings and a median list price of $290,000, inventory is tight and homes move — the median time on market is 12 days, and sellers are pulling in about 98% of asking. If you're serious about landing here, come pre-approved and ready to act.
Windward Square is a community in Winter Park, Florida.
Quick facts
$270,000 – $300K price range
1,544 sqft median home
$95/mo median HOA
$2,075/mo median rent
13 sold in 12 months
Drive times
On the market now
Homes for sale in Windward Square
$299,990
2275 ISLAND RUN, WINTER PARK
3 bd · 2 ba · 1,467 sqft
$275,000$295,000
2302 BARBADOS DRIVE, WINTER PARK
2 bd · 2 ba · 1,544 sqft
$270,000$290,000
2487 HARBOUR WAY, WINTER PARK
3 bd · 3 ba · 1,803 sqft
Every active listing inside the Windward Square boundary
Open full map search →Find your fit
Browse Windward Square
By feature — on the live map
The numbers that matter
The Windward Square market
13
Sold, last 12 months
$272,250
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
13 days
Median time to sell
Windward Square vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 19.6% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windward Square boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windward Square is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windward Square home
≈ $2,148/mo
$275,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$95/mo
Median HOA
From current listings inside the boundary
$2,075/mo
Median rent
Homes for rent inside the boundary
Population
567
Median age
31
Median income
$61,250
Median home value
$219,300
Beyond the listings
Living in Windward Square
Appearance oriented
Top 1% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Emotional
Top 2% in the U.S.Gratitude
From generous tipping to standing ovations, this population has a way with giving someone a pat on the back.
Active
Top 3% in the U.S.Fitness Obsession
Passionate about strength training, this population relies heavily on the encouragement of the exercise community. While these people seek the latest fitness techniques, they're also interested in supplements and equipment.
Appearance oriented
Top 4% in the U.S.All About Hair
Passionate about all things hair, this population is talking about hair tutorials or the hottest celebrity blowout.
Lifestyles
Top 4% in the U.S.Daily Grind
Whether throwing punches at the boxing club or punching the clock at work, this population likes to talk about their hard work.
Active
Top 4% in the U.S.Functional Fitness
Looking good and reaching fitness goals is all about discipline: Eat right. Work hard. No excuses. This population is more likely to view working out as a means to an end.
People who close here
Our Winter Park experts
Straight answers
Windward Square FAQs
Is Windward Square a good place to live?+
It's a quiet, practical neighborhood that trades square footage for location, putting you close to Kenilworth and the rest of Winter Park while keeping prices down. Assigned schools include Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High. If you value proximity and value over a big footprint, it's a smart fit.
Is Windward Square expensive?+
By Winter Park standards, no — the median list price is $290,000 and active listings run from $255,000 to $299,999. That makes it one of the more attainable pockets in the area, especially for first-time buyers or downsizers.
What do homes cost in Windward Square?+
Active listings currently sit between $255,000 and $299,999 with a median of $290,000, and average pricing works out to about $212 per square foot on homes around 1,324 square feet. Over the last 12 months, 14 homes sold at a median of $271,125.
How is the market in Windward Square?+
It's competitive and fast-moving — only 3 homes are active right now, the median time on market is 12 days, and sellers are getting about 98% of asking. Low inventory means you'll want financing lined up before you tour.
What about HOA fees and property taxes?+
The median HOA runs about $98 a month, and median property tax is roughly $3,553 a year. For renters or investors weighing the numbers, median rent in the area sits around $2,050 a month.
Keep exploring
More Winter Park neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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