Neighborhood · Winter Park, Florida
Conwill Estates
Refined Winter Park living close to it all
2
Homes for sale
$1,485,000
Median list price
$501
Avg price / sqft
6
Median days on market
Conwill Estates sits in the heart of Winter Park, one of Orange County's most established addresses, where mature tree canopy and well-kept lots set a quiet, residential tone. It's a small enclave with an easy connection to the wider community — nearby names like Lake Killarney, Winter Park Pines, and Hannibal Square give you a sense of the caliber of the area, and the assigned schools run to Winter Park High, Maitland Middle, and Lakemont Elementary.
For buyers, this is a tight, competitive market. There are just 2 active listings right now with a median list price of $1,445,000, homes are moving in about 3.5 days, and sellers over the past year have averaged 102% of asking. If you're serious about landing here — or exploring adjacent options like Kenilworth or the broader mix of Winter Park homes for sale — you'll want financing lined up and a plan to act fast.
Conwill Estates is a community in Winter Park, Florida.
Quick facts
$775,000 – $2.2M price range
2,795 sqft median home
7 sold in 12 months
Drive times
On the market now
Homes for sale in Conwill Estates
$775,000
1562 ARBOR PARK DRIVE, WINTER PARK
4 bd · 2.5 ba · 1,899 sqft
$2,195,000
1750 WALNUT AVENUE, WINTER PARK
4 bd · 4.5 ba · 3,691 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
7
Sold, last 12 months
$1,800,000
Median sold price
101%
Sale-to-list ratio
What sellers actually get vs asking
6 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
▼ 12.8% 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
≈ $9,160/mo
$1,485,000 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 small, established Winter Park neighborhood with mature streets and access to sought-after schools including Winter Park High and Lakemont Elementary. You're close to community anchors like Lake Killarney while staying within an easy commute to greater Orlando.
Is Conwill Estates expensive?+
Yes, it's a high-end pocket of Winter Park. The median list price is $1,445,000, with active homes ranging from $695,000 to $2,195,000, so budget accordingly and expect quality to match.
What do homes cost in Conwill Estates?+
Current listings carry a median price of $1,445,000, and homes over the past year sold at a median of $1,500,500. At roughly $555 per square foot on a median home size of 2,521 square feet, pricing reflects the neighborhood's Winter Park pedigree.
How is the market in Conwill Estates?+
It's fast and competitive, with just 2 active listings and a median of only 3.5 days on market. Sellers averaged 102% of asking over the last 12 months across 6 sales, so come prepared to move quickly — the pace here rivals nearby Winter Park Pines.
What about HOA fees and property taxes?+
There's no reported HOA data for the neighborhood, so fees aren't a factor buyers should count on here. Property taxes run a median of about $11,933 per year, in line with the area's 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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