Homes for sale · Kissimmee, FloridaCrestwynd Bay
Gated Kissimmee living minutes from Disney
8
Homes for sale
$264,000
Median list price
$250
Avg price / sqft
87
Median days on market
Crestwynd Bay is a compact, mostly gated community in Kissimmee that puts you about 17 minutes from Walt Disney World and roughly a half hour from Universal Orlando and Orlando International Airport. It's the kind of neighborhood that works for a primary home, a second home, or an income property — close to the theme-park economy without being swallowed by it, and surrounded by well-known Osceola communities like Solivita, Bellalago, and Poinciana Village. Homes here lean toward the practical side, with a median footprint around 1,362 square feet and a handful of pool and gated options.
For a buyer today, the market is small and worth watching closely. There are 8 active listings with a median list price of $264,000, and homes are taking a median of 87 days to sell — so you have room to be deliberate rather than rushed. Over the last year 6 homes closed at a median of $247,450, with sellers collecting about 94% of asking, which tells you there's real negotiating room. If you're comparing options across Kissimmee homes for sale, Crestwynd Bay's gated setting and location make it a steady, livable choice.
Crestwynd Bay is a community in Kissimmee, Florida.
Quick facts
$234,000 – $800K price range
1,362 sqft median home
$333/mo median HOA
$2,025/mo median rent
5 sold in 12 months
Drive times
On the market now
Homes for sale in Crestwynd Bay
$300,000
2693 ANDROS LANE, KISSIMMEE
3 bd · 3 ba · 1,187 sqft
$800,000
4899 CANAL DR LAKE, LAKE WORTH
3 bd · 3 ba · 1,187 sqft
$234,000$247,000
2685 ANDROS LANE, KISSIMMEE
3 bd · 3 ba · 1,187 sqft
$259,000$265,000
2691 ANDROS LANE, KISSIMMEE
3 bd · 2.5 ba · 1,595 sqft
$269,000$298,999
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
$252,000$272,500
2680 MAYAGUANA STREET, KISSIMMEE
3 bd · 3 ba · 1,362 sqft
$245,900$246,000
2626 ANDROS LANE, KISSIMMEE
3 bd · 3 ba · 1,362 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
5
Sold, last 12 months
$245,000
Median sold price
93%
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
▼ 18.9% 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
$264,000 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
$2,025/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
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Nicholas Giaccone
Director of Agent Success
Straight answers
Crestwynd Bay FAQs
Is Crestwynd Bay a good place to live?+
It's a solid fit for buyers who want a gated Kissimmee address close to work, travel, and the theme parks — Disney is about 17 minutes out and the airport around 33. Assigned schools include Osceola County School for the Arts, Celebration High School, and Westside K-8 School. The community is small and mostly gated, which keeps things quiet and secure.
Is Crestwynd Bay expensive?+
Not by Central Florida standards. The median list price is $264,000 and the average cost runs about $250 per square foot, with the current active range spanning $234,000 to $800,000. That makes it more attainable than many nearby options like Bellalago.
What do homes cost in Crestwynd Bay?+
Right now there are 8 active listings with a median list price of $264,000, and the median home size is about 1,362 square feet. Over the past 12 months, 6 homes sold at a median price of $247,450, so recent closings have landed a bit below current asking prices.
How is the market in Crestwynd Bay?+
It's a slower, buyer-friendly market with just 8 active listings and a median of 87 days on market. Sellers are averaging 94% of their asking price, which means there's genuine room to negotiate. If this inventory feels tight, it's worth widening your search across Kissimmee homes for sale.
What about HOA fees and property taxes?+
The median HOA runs about $333 per month, which is typical for a gated community with shared amenities and access control. Median property taxes come in around $3,250 per year. If you're considering renting, the median rent in the area is about $2,025 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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