Neighborhood · Winter Park, Florida
Windward Square
A quiet Winter Park pocket with real value
Windward Square sits in the eastern reach of Winter Park homes for sale, a small residential neighborhood where the pace is calm and the commute stays manageable. You're about 24 minutes from downtown Orlando and 32 from MCO, with the shops and lakes that define the area — from Lake Killarney to the walkable streets of Hannibal Square — an easy drive away. It's the kind of place buyers land when they want the Winter Park address without the Park Avenue price tag.
The market here is tight and moves on scarcity: there are no active listings right now, so opportunities come as they come rather than off a big shelf. Over the last 12 months, 14 homes sold at a median of $271,125, with sellers pulling in 98% of asking on average. If you're deciding between this and pricier pockets like Winter Park Pines or Kenilworth, Windward Square is where the numbers still work for a first move or a rental play.
Windward Square is a community in Winter Park, Florida.
Quick facts
$2,048/mo median rent
14 sold in 12 months
Drive times
On the market now
Homes for sale in Windward Square
Nothing active right now.
Set an alert below and we’ll email you the moment something lists here.
Every active listing inside the Windward Square boundary
Open full map search →The numbers that matter
The Windward Square market
14
Sold, last 12 months
$271,125
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
11 days
Median time to sell
Windward Square vs Winter Park
Median sold price — 3-yr, 3-mo rolling
▼ 5.4% 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.
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.
On the calendar
Near Windward Square
Jul
12
Sun
View of Oyster Bay
Explore the View of Oyster Bay, an artistic zenith of proficiency, emphasizing vibrant wisteria vines against serene bay backdrops. Discover stunning harmony as structure…
Jul
12
Sun
Orlando Farmers Market
10:00am
The Eola Sunday Market is celebrated as one of the finest in Central Florida. Attendees can enjoy an array of fresh fruits and vegetables, homemade bread, local cuisine,…
Jul
12
Sun
Vibe, Sip, and Make Jewelry
Wanda Taylor, a seasoned craftswoman, invites the community to a workshop where she'll share her expertise in creating a wide range of handcrafted items. Attendees will h…
Jul
12
Sun
I Remember When...Reflections From The RMA Staff
This exhibition, curated by the staff of the Rollins Museum of Art, showcases a diverse range of media and themes, all centered around the concept of memory and storytell…
Jul
12
Sun
Being Outdoors
Celebrating the nation's 250th anniversary, the exhibition Being Outdoors delves into the deep-rooted connections between outdoor recreational activities and American ide…
Jul
12
Sun
The Captivating Unknown
The event, The Captivating Unknown, is an art exhibition that explores humanity's fascination with the cosmos through various artistic mediums. The works on display aim t…
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 residential neighborhood with an easy 24-minute drive to downtown Orlando and about 32 minutes to MCO. You're close to Winter Park staples and lakes like Lake Killarney, and homes are zoned for Eastbrook Elementary, Tuskawilla Middle, and Lake Howell High School. It suits buyers who want proximity without the noise of the busier districts.
Is Windward Square expensive?+
Compared to much of Winter Park, no — the median sold price over the last 12 months was $271,125. That makes it one of the more approachable entry points in the area, especially against neighboring communities like Kenilworth. For a first purchase or an investment, the pricing is refreshingly grounded.
What do homes cost in Windward Square?+
Fourteen homes sold here in the past year at a median price of $271,125, and sellers received about 98% of their asking price on average. There are no active listings at the moment, so inventory is scarce and you'll want to move quickly when something comes up.
How is the market in Windward Square?+
It's a small, tight market — zero active listings right now with 14 sales over the last 12 months. The 98% list-to-sold ratio tells you homes are priced sensibly and don't sit long, so buyers should be ready to act when a listing appears in this or nearby pockets like Winter Park Pines.
What about HOA fees and property taxes?+
Specific HOA and property tax figures aren't available for the neighborhood right now, so confirm those details on any individual home you're considering. For context, median rent in the area runs $2,048 a month, which helps frame the carrying costs on an entry-priced purchase here.
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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