Neighborhood · Winter Park, Florida
Conwill Estates
A quiet luxury pocket in Winter Park's core
2
Homes for sale
$1,750,000
Median list price
$564
Avg price / sqft
54
Median days on market
Conwill Estates is a small, established enclave in Winter Park, the tree-lined Orange County city known for its brick streets and lakeside character. Homes here sit on generous lots close to nearby communities like Lake Killarney, the walkable Hannibal Square dining district, and the residential streets of Orwin Manor. It's the kind of neighborhood where you're minutes from downtown Winter Park yet tucked onto streets that stay calm.
For a buyer today, this is a luxury market with limited inventory — just 3 active listings, with a median list price of $1,900,000 and prices running from $775,000 up to $2,725,000. Two of those active homes are new construction and two have pools, so there's a mix of turnkey and updated options. Homes move quickly here, with a median of 15 days on market, so being ready to act matters.
Conwill Estates is a community in Winter Park, Florida.
Quick facts
$775,000 – $2.7M price range
2,842 sqft median home
6 sold in 12 months
Drive times
On the market now
Homes for sale in Conwill Estates
$2,725,000
1773 WALNUT AVENUE, WINTER PARK
5 bd · 4.5 ba · 3,784 sqft
$775,000
1562 ARBOR PARK DRIVE, WINTER PARK
4 bd · 2.5 ba · 1,899 sqft
Every active listing inside the Conwill Estates boundary
Open full map search →Find your fit
Browse Conwill Estates
By feature — on the live map
Where the market lives
The numbers that matter
The Conwill Estates market
6
Sold, last 12 months
$1,912,500
Median sold price
95%
Sale-to-list ratio
What sellers actually get vs asking
23 days
Median time to sell
Conwill Estates vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 175.7% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Conwill Estates boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Conwill Estates is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Conwill Estates home
≈ $10,268/mo
$1,750,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
211
Median age
49
Median income
$193,750
Median home value
$808,200
Beyond the listings
Living in Conwill Estates
Pieces of History
You can find these people researching an upcoming exhibit at the natural history museum or learning about a famous monument. This population enjoys learning about the past.
Appearance oriented
Top 22% in the U.S.Fitness Fashion
Workout clothes aren't just for working out anymore. This population enjoys wearing name-brand athletic apparel for fashion and functional purposes.
Hobbies & Interests
Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Active
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.
Food & Drink
Trendy Eats
Meals are a social experience, and these foodies take it to the next level. This population can't wait to snap a pic of their plate and share it before chowing down.
Food & Drink
Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
People who close here
Our Winter Park experts
Straight answers
Conwill Estates FAQs
Is Conwill Estates a good place to live?+
It's a compact, established neighborhood in the heart of Winter Park, close to the shops and restaurants of Hannibal Square and assigned to Winter Park High, Maitland Middle, and Lakemont Elementary. The streets stay quiet while keeping you minutes from downtown, which appeals to buyers who want luxury without leaving the city core.
Is Conwill Estates expensive?+
Yes — this is a high-end pocket, with a median list price of $1,900,000 and a range from $775,000 to $2,725,000. At an average of $591 per square foot, it sits firmly in Winter Park's luxury tier.
What do homes cost in Conwill Estates?+
Current listings run from $775,000 to $2,725,000, with a median list price of $1,900,000 and a median home size around 2,950 square feet. Over the past year, 8 homes sold at a median price of $1,837,500, so recent sales line up closely with what's being asked today.
How is the market in Conwill Estates?+
It's tight and fast-moving, with only 3 active listings and a median of just 15 days on market. Sellers averaged 99% of their asking price over the last 12 months, so well-priced homes here don't sit long — compared to the broader Winter Park market, inventory is especially limited.
What about HOA fees and property taxes?+
There's no reported HOA data for the neighborhood, which is common for established Winter Park streets. Property taxes run a median of about $9,725 per year, in line with the area's higher home values.
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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