Neighborhood · Kissimmee, Florida
Crestwynd Bay
Gated Living Minutes From Disney
8
Homes for sale
$263,750
Median list price
$195
Avg price / sqft
65
Median days on market
Crestwynd Bay is a compact, mostly gated community in Kissimmee, sitting close enough to the theme parks to make a spontaneous evening at the parks realistic — Walt Disney World is about 17 minutes away, with Universal Orlando and Orlando International Airport both around 33 minutes out. It's the kind of pocket that draws buyers who want a manageable-sized home and the security of a controlled entrance without paying resort-community premiums. If you're comparing it against the bigger vacation-rental names nearby like Storey Lake or Solara, Crestwynd Bay reads as more everyday-neighborhood than short-term-rental machine.
For a buyer today, the math is approachable: the median list price sits at $263,750 across just 8 active listings, so inventory is thin but priced within reach. Homes are moving at a median of 65 days on market, and over the last year sellers collected about 94% of asking — meaning there's real room to negotiate here. Look at it alongside the wider Kissimmee homes for sale market and against value-focused spots like Lake Marion Village to see where your dollar goes furthest.
Crestwynd Bay is a community in Kissimmee, Florida.
Quick facts
$245,000 – $299K price range
1,362 sqft median home
$333/mo median HOA
$1,800/mo median rent
7 sold in 12 months
Drive times
On the market now
Homes for sale in Crestwynd Bay
$245,000
7646 LONG ISLAND DRIVE, KISSIMMEE
3 bd · 3 ba · 1,187 sqft
$280,000
2691 ANDROS LANE, KISSIMMEE
3 bd · 2.5 ba · 1,595 sqft
$255,000
7631 LONG ISLAND DR, KISSIMMEE
3 bd · 3 ba · 1,187 sqft
$299,000$315,000
7601 ACKLINS ROAD, KISSIMMEE
3 bd · 2.5 ba · 1,595 sqft
$290,000$293,000
2682 MAYAGUANA STREET, KISSIMMEE
3 bd · 2.5 ba · 1,595 sqft
$272,500
2680 MAYAGUANA STREET, KISSIMMEE
3 bd · 3 ba · 1,362 sqft
$246,500$247,000
2626 ANDROS LANE, KISSIMMEE
3 bd · 3 ba · 1,362 sqft
$249,990
2662 Mayaguana Street, Kissimmee FL 34747, KISSIMMEE
3 bd · 3 ba · 1,187 sqft
Every active listing inside the Crestwynd Bay boundary
Open full map search →Find your fit
Browse Crestwynd Bay
By feature — on the live map
The numbers that matter
The Crestwynd Bay market
7
Sold, last 12 months
$249,900
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
68 days
Median time to sell
Crestwynd Bay vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 5.5% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Crestwynd Bay boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Crestwynd Bay is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Crestwynd Bay home
≈ $2,205/mo
$263,750 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$333/mo
Median HOA
From current listings inside the boundary
$1,800/mo
Median rent
Homes for rent inside the boundary
Population
493
Median age
31
Median income
$92,154
Median home value
$297,100
Beyond the listings
Living in Crestwynd Bay
Hobbies & Interests
Top 2% in the U.S.Wanderlust
Always thinking about their next destination, this population loves exploring new places abroad or right in their own backyard. They hold onto past trips by sharing their favorite memories and pictures year round.
Entertainment
Top 5% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Lifestyles
Top 6% 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.
Entertainment
Top 13% in the U.S.Live Experiences
When it comes to entertainment, this population is looking for the ultimate experience. Whether it's a charity fundraiser or a concert, elements such as lights, sounds, and merchandise are critical for a good time.
Entertainment
Top 15% in the U.S.Lighthearted Fun
This population is all about keeping the mood light and good, clean fun. Common activities include spending time outdoors, catching up with friends, and dancing.
Food & Drink
Top 18% 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.
Straight answers
Crestwynd Bay FAQs
Is Crestwynd Bay a good place to live?+
It suits buyers who want a small, mostly gated community close to the parks — five of the eight current listings are behind a gate, and Walt Disney World is about 17 minutes away. Assigned schools include the Osceola County School for the Arts and Westside K-8 School, and downtown Orlando is roughly 37 minutes out for work commutes.
Is Crestwynd Bay expensive?+
Not by Central Florida standards — the median list price is $263,750, with active homes ranging from $245,000 to $299,000. Compared with pricier resort-style communities nearby, it lands in an accessible bracket, and the broader Kissimmee homes for sale market gives you plenty of context for the value.
What do homes cost in Crestwynd Bay?+
Expect a median around $263,750 to list and about $254,950 for recent sales, at roughly $195 per square foot on a median home of 1,362 square feet. Only 6 homes sold in the past 12 months, so it's a low-volume market where each listing matters.
How is the market in Crestwynd Bay?+
Inventory is tight at just 8 active listings, and homes take a median of 65 days to sell. With sellers averaging 94% of asking price, there's meaningful negotiating room — a slower pace that generally favors patient buyers over sellers.
What about HOA and property taxes?+
Plan on a median HOA of about $333 per month, which is typical for a gated community with shared upkeep. Property taxes run around $3,266 per year, and if you're weighing rental potential the median rent in the area is roughly $1,800 per month.
Keep exploring
More Kissimmee 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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