Neighborhood · Winter Park, Florida
Villas Of Casselberry
Low-maintenance living near the Winter Park line
3
Homes for sale
$360,000
Median list price
$257
Avg price / sqft
44
Median days on market
Villas Of Casselberry sits at the edge of the Winter Park area, an easygoing pocket of manageable homes for buyers who'd rather spend weekends near the lakes than mowing an oversized yard. It's the kind of place that pairs well with the character of nearby Winter Park Pines and the shoreline draw of Lake Killarney, with downtown Orlando only about 21 minutes out and MCO reachable in roughly 33. If you want proximity to the culture and dining of the broader Winter Park scene without the price tag of Hannibal Square, this neighborhood earns a look.
The market here is small and moves at a measured pace. There are just 2 active listings, with a median list price of $385,000 and homes sitting a median of about 45 days before going under contract. Over the last year 11 homes sold at a median of $285,000, and sellers collected 98% of asking on average — a sign that realistically priced homes still close cleanly.
Villas Of Casselberry is a community in Winter Park, Florida.
Quick facts
$349,900 – $405K price range
1,397 sqft median home
$63/mo median HOA
$2,410/mo median rent
10 sold in 12 months
Drive times
On the market now
Homes for sale in Villas Of Casselberry
$349,900
3328 HAMLET LOOP, WINTER PARK
3 bd · 2 ba · 1,397 sqft
$405,000$420,000
3440 ALLSTON LANE, WINTER PARK
3 bd · 2.5 ba · 1,533 sqft
$360,000$365,000
3374 HAMLET LOOP, WINTER PARK
3 bd · 2.5 ba · 1,397 sqft
Every active listing inside the Villas Of Casselberry boundary
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Browse Villas Of Casselberry
Where the market lives
The numbers that matter
The Villas Of Casselberry market
10
Sold, last 12 months
$282,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
21 days
Median time to sell
Villas Of Casselberry vs Winter Park
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 2.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Villas Of Casselberry boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Villas Of Casselberry is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Villas Of Casselberry home
≈ $2,614/mo
$360,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$63/mo
Median HOA
From current listings inside the boundary
$2,410/mo
Median rent
Homes for rent inside the boundary
Population
535
Median age
36
Median income
$80,648
Median home value
$283,200
Beyond the listings
Living in Villas Of Casselberry
Hobbies & Interests
Top 1% in the U.S.Handcrafted
The only thing more beautiful than handmade decor? The hands that made it. This population appreciates the time and care put into one-of-a-kind pieces.
Attitudes
Top 1% in the U.S.Deal Seekers
These people are hunting discounts, contests, and promotions. The population loves a good sale, and they can't wait to share their bargain finds and winnings with friends and family.
Food & Drink
Top 3% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
Hobbies & Interests
Top 3% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Hobbies & Interests
Top 3% in the U.S.Bookish
Always seeking the next book, article, or poem to read, this activity is prevalent in areas where reading is a way of life. Although a solo activity, the expression of the love of books is a bonding, communal experience.
Lifestyles
Top 5% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Straight answers
Villas Of Casselberry FAQs
Is Villas Of Casselberry a good place to live?+
It's a practical, low-key choice for buyers who value location and easy upkeep over sprawl. You get quick access to the Winter Park area's dining and lakes, a roughly 21-minute drive to downtown Orlando, and schools including Eastbrook Elementary and Lake Howell High. The manageable home sizes make it especially workable for first-time buyers and downsizers.
Is it expensive to buy here?+
Compared to the broader Winter Park area, it's relatively accessible. The median list price is $385,000 and the median sold price over the last year was $285,000, well below what waterfront and Kenilworth addresses typically command.
What do homes cost in Villas Of Casselberry?+
Current active listings range from $365,000 to $405,000, with a median list of $385,000 and an average of about $263 per square foot. Homes run around 1,465 square feet at the median, so you're generally looking at compact, single-family-scale layouts rather than large estates.
How is the market right now?+
It's a small, steady market with only 2 active listings and 11 sales in the past 12 months. Homes take a median of about 45 days to go under contract, and sellers are averaging 98% of asking — meaning fairly priced homes still close close to list.
What about HOA fees and property taxes?+
The median HOA is about $64 a month, which is modest for the area, and the median annual property tax runs around $3,345. If you're weighing a rental instead, the median rent here is roughly $1,995 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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