Neighborhood · Kissimmee, Florida
Crestwynd Bay
Gated living minutes from Disney's front gate
8
Homes for sale
$252,495
Median list price
$200
Avg price / sqft
54
Median days on market
Crestwynd Bay is a compact, gated neighborhood in Kissimmee that trades sprawl for proximity — Walt Disney World is about 17 minutes away, and Orlando International Airport and Universal Orlando both sit around 33 minutes out. Most of the active homes here are inside gated sections, giving the community a quieter, more contained feel than the resort-heavy developments that surround it. If you like the idea of theme-park weekends without living in the middle of the crowds, this stretch of Kissimmee homes for sale is worth a close look.
The market here is small and moves fast: just 7 active listings, a median list price of $255,000, and a median of only 9 days on market. Sellers have been getting about 97% of asking, so well-priced homes don't linger. Buyers weighing Crestwynd Bay against larger nearby communities like Storey Lake or Solara will find fewer options but a tighter, more residential setting.
Crestwynd Bay is a community in Kissimmee, Florida.
Quick facts
$245,000 – $315K price range
1,275 sqft median home
$333/mo median HOA
$1,750/mo median rent
3 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
$272,500
2680 MAYAGUANA STREET, KISSIMMEE
3 bd · 3 ba · 1,362 sqft
$315,000
7601 ACKLINS ROAD, KISSIMMEE
3 bd · 2.5 ba · 1,595 sqft
$255,000
7631 LONG ISLAND DR, KISSIMMEE
3 bd · 3 ba · 1,187 sqft
$290,000$293,000
2682 MAYAGUANA STREET, KISSIMMEE
3 bd · 2.5 ba · 1,595 sqft
$247,000
2626 ANDROS LANE, KISSIMMEE
3 bd · 3 ba · 1,362 sqft
$249,990
2662 MAYAGUANA STREET, KISSIMMEE
3 bd · 3 ba · 1,187 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
Where the market lives
The numbers that matter
The Crestwynd Bay market
3
Sold, last 12 months
$275,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
179 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
▼ 5.8% 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
≈ $2,145/mo
$252,495 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
$1,750/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.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Straight answers
Crestwynd Bay FAQs
Is Crestwynd Bay a good place to live?+
It's a good fit if you want a small, mostly gated neighborhood with quick access to the parks — Disney is about 17 minutes away and Orlando International Airport is roughly 33. Assigned schools include Osceola County School for the Arts and Westside K-8 School. The scale is intimate, so it feels more residential than the larger resort communities nearby.
Is Crestwynd Bay expensive?+
Not by Central Florida standards — the median list price is $255,000 and homes average about $203 per square foot. That's an accessible entry point compared to bigger vacation-home developments like Windsor at Westside. The median home size is around 1,187 square feet, so you're generally looking at right-sized rather than sprawling floor plans.
What do homes cost in Crestwynd Bay?+
Active listings currently range from $245,000 to $315,000, with a median of $255,000. Over the last 12 months, the 3 homes that sold closed at a median of $275,000. Sellers averaged about 97% of their asking price, which tells you buyers aren't finding much room to negotiate.
How is the market in Crestwynd Bay?+
It's tight and quick — only 7 active listings and a median of 9 days on market means well-priced homes go under contract fast. With just 3 sales in the past year, inventory turnover is low, so buyers should be prepared to move when the right listing appears. Compared to larger communities like Lake Marion Village, you're working with a much smaller pool of options.
What about HOA fees and property taxes?+
The median HOA runs about $333 per month, which reflects the gated, managed nature of much of the neighborhood. Median property tax comes in around $3,046 per year. If you're considering renting, the median rent here is about $1,750 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.
Never miss a listing
New Crestwynd Bay homes, in your inbox
A daily digest of new Kissimmee listings — straight from the MLS. Unsubscribe anytime.