Homes for sale · Davenport, FloridaWindsor Island
Resort-style vacation homes minutes from Disney
103
Homes for sale
$630,000
Median list price
$210
Avg price / sqft
120
Median days on market
Windsor Island is a gated, resort-style community in Davenport built around short-term rental living, where nearly every home comes with a private pool and the amenity center leans into the vacation energy. It suits investors chasing Disney-area demand and buyers who want a turnkey second home within easy reach of the theme parks, without giving up space — the median home here runs north of 3,200 square feet. If you're weighing it against other local options, it sits in the same orbit as Champions Gate and Solterra Resort, two of the better-known resort communities in the area.
For a buyer today, the market reads as deep and patient: 103 active listings, a median list price of $630,000, and homes sitting a median of 120 days before selling. That's leverage — sellers are closing at about 96% of asking, and the $1M+ tier is thin with just one active listing. Compare the data against nearby Highlands Reserve or broader Davenport homes for sale to understand where Windsor Island's pricing and HOA structure fit the short-term-rental math.
Windsor Island is a community in Davenport, Florida.
Quick facts
$389,800 – $1.0M price range
3,234 sqft median home
$712/mo median HOA
$3,100/mo median rent
63 sold in 12 months
Drive times
Living in Windsor Island
Windsor Island is a gated, resort-style community in Davenport, in Polk County, built around the short-term rental economy that surrounds the Orlando theme parks. The homes here are large — a median of about 3,234 square feet — and designed for vacation living, with nearly every property including a private pool. This isn't a historic small town or a traditional subdivision; it's a purpose-built community where the rhythm of daily life is shaped by guests, cleaning turnovers, and the steady flow of families visiting the parks.
The community suits two main types of buyer: the investor looking for a Disney-area income property, and the owner who wants a spacious vacation home they can also rent when they're not using it. With Walt Disney World roughly 30 minutes away, the location is the whole point. If you're the kind of buyer who wants neighbors you'll know for years and a quiet residential street, this specific community may feel more transient than you'd like.
That said, the gated setting and resort amenities give it a cohesive, managed feel. Of the 103 active listings, 72 sit behind gates, and the shared amenity package is part of what justifies the HOA. For buyers who understand they're entering a vacation-rental market rather than a classic residential one, Windsor Island offers a clear, well-defined product.
Neighborhoods and communities in Windsor Island
Windsor Island itself is one of several resort-style communities clustered in and around Davenport, and it helps to understand the neighbors when you're comparing options. Champions Gate is one of the best-known in the area, anchored by its own resort and golf reputation, and it draws a similar short-term-rental buyer. Solterra Resort is another close comparison, with a resort amenity model that mirrors what Windsor Island offers.
For buyers weighing a slightly different feel, Highlands Reserve and Providence sit nearby and bring their own mix of homes and community character. Providence in particular leans more residential, which can appeal to buyers who want a year-round neighborhood rather than a pure vacation-rental setting.
Ridgewood Lakes Village rounds out the local landscape of notable communities in the area. The practical takeaway is that Davenport offers a spectrum — from heavily rental-driven resort communities like Windsor Island to more traditional neighborhoods — so it's worth touring a few before committing. Each has its own HOA structure, amenity set, and rental rules that materially affect the investment math.
Homes for sale in Windsor Island: prices and housing
The current market shows 103 active listings with a median list price of $630,000, spanning a range from $389,800 to $1,049,000. The average price per square foot is about $210, and the median home size is roughly 3,234 square feet — these are substantial, multi-bedroom homes built to sleep large vacation groups. Over the past 12 months, 62 homes sold at a median price of $572,500, with sellers receiving about 96% of asking on average.
The housing here is heavily weighted toward pool homes: 100 of the 103 active listings include a private pool, and 72 are gated. There are no waterfront or golf-course properties in the current active set, and no 55+ inventory. The $1M+ tier is minimal with a single active listing, and new construction is nearly absent — just one new-build listing — so expect to shop primarily among resale resort homes.
Carrying costs are a real factor. The median HOA is about $712 per month, which covers the resort amenities and gated infrastructure, and median property taxes run around $9,670 per year. For investors, the median rent of $3,100 per month is a useful anchor, though short-term rental income can vary widely with seasonality and occupancy. With a median 120 days on market, buyers generally have time to analyze the numbers and negotiate.
Schools in Windsor Island
The most commonly assigned schools for this area are Loughman Oaks Elementary School, Lake Alfred-Addair Middle School, and Ridge Community High School, all within the Polk County school system. Because Windsor Island is primarily a short-term-rental community, school zoning is less central to most buyers here than it would be in a traditional family neighborhood.
That said, if you're purchasing as a primary residence with children, confirm the current attendance zone directly with Polk County Public Schools before you buy. School boundaries can change from year to year, and the assignment tied to a specific address is the only one that matters for enrollment.
For families who prioritize schools above all, it's worth comparing attendance zones across the nearby communities as well, since Davenport straddles areas served by different schools. Verifying the zone in writing avoids surprises after closing.
Getting around Windsor Island
The location is defined by its proximity to the theme parks. Walt Disney World is about a 30-minute drive, which is the single biggest draw for the vacation-rental demand that fuels this market. Universal Orlando sits around 46 minutes away, and Orlando International Airport (MCO) is also roughly 46 minutes — convenient for owners and guests flying in.
Downtown Orlando is approximately 45 minutes, so while the community is accessible to the wider metro, it's positioned as a parks-first location rather than a city commuter base. The Davenport area connects to the major regional corridors that link the attractions, Interstate 4, and the surrounding towns, making car travel the practical default here.
Day to day, you'll rely on a vehicle for everything — there's no walkable urban core within the community itself. For buyers and renters alike, the trade-off is clear: you give up walkability in exchange for quick highway access to the parks and the airport.
Is Windsor Island a good place to live?
Windsor Island makes the most sense for buyers who understand what it is: a gated, resort-style, short-term-rental community rather than a conventional neighborhood. If your goal is a spacious vacation home with a private pool minutes from Disney — or an income property in a proven rental market — it checks those boxes, with a median home size over 3,200 square feet and nearly universal pool inclusion.
The honest trade-offs are cost and pace. The median HOA of about $712 per month and property taxes near $9,670 per year add up quickly, and the transient nature of a rental community means it won't feel like a settled year-round neighborhood. On the upside, the current market is patient — 120 median days on market and sellers getting about 96% of asking — which gives buyers room to negotiate and analyze the numbers carefully.
For an investor or a second-home buyer, Windsor Island is a straightforward, well-defined product with strong proximity to the parks. For a family seeking a permanent primary residence with deep community roots, a more residential nearby option like Providence may be a better fit. Know your goal, run the carrying-cost math, and the decision becomes clear.
On the market now
Homes for sale in Windsor Island
View all 103 →
$1,049,000
4421 KAIPO ROAD, DAVENPORT
8 bd · 5 ba · 4,025 sqft
$999,000
3739 LANA AVE, DAVENPORT
10 bd · 8 ba · 4,399 sqft
$850,000
4197 LANA AVENUE, DAVENPORT
10 bd · 8 ba · 4,399 sqft
$795,000
2031 LELANI CIRCLE, DAVENPORT
10 bd · 8 ba · 4,399 sqft
$780,000
4458 KAIPO ROAD, DAVENPORT
7 bd · 5.5 ba · 3,282 sqft
$590,000
4039 LANA AVENUE, DAVENPORT
5 bd · 5.5 ba · 2,622 sqft
$525,000
4154 LANA AVENUE, DAVENPORT
5 bd · 4.5 ba · 2,293 sqft
$499,000
3966 LANA AVENUE, DAVENPORT
5 bd · 4 ba · 2,283 sqft
$439,999
971 PARADISE DRIVE, DAVENPORT
5 bd · 4.5 ba · 2,293 sqft
$693,000
1196 ALOHA BOULEVARD, DAVENPORT
7 bd · 5.5 ba · 3,296 sqft
$489,000
3769 PACIFIC LANE, DAVENPORT
5 bd · 4.5 ba · 2,355 sqft
$750,000
3052 MAHALO DRIVE, DAVENPORT
9 bd · 6 ba · 4,399 sqft
Every active listing inside the Windsor Island boundary
Open full map search →Find your fit
Browse Windsor Island
By feature — on the live map
Where the market lives
The numbers that matter
The Windsor Island market
63
Sold, last 12 months
$570,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
116 days
Median time to sell
Windsor Island vs Davenport
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 8.5% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Windsor Island boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Windsor Island is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Windsor Island home
≈ $5,047/mo
$630,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$712/mo
Median HOA
From current listings inside the boundary
$3,100/mo
Median rent
Homes for rent inside the boundary
Beyond the listings
Living in Windsor Island
Hobbies & Interests
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.
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.
Hobbies & Interests
Natural Beauty
This population marvels at the beauty of nature, and they want to capture every breath-taking scene.
Hobbies & Interests
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.
Hobbies & Interests
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.
Hobbies & Interests
Animal Advocates
Passionate about animal welfare, this population wants to know how best to care for their own pets (with toys and training) and help other animals find their fur-ever home.
People who close here
Our Davenport experts
Straight answers
Windsor Island FAQs
Is Windsor Island a good place to live?+
It's built primarily as a resort and short-term-rental community rather than a traditional suburb, so it suits investors and vacation-home owners more than someone looking for a quiet year-round neighborhood. If you want proximity to the parks, a private pool, and a gated setting, it delivers — Walt Disney World is about 30 minutes away. Weigh the lifestyle against nearby options like Providence if you prefer a more residential feel.
Is Windsor Island expensive?+
The median list price is $630,000 with active homes ranging from $389,800 to $1,049,000, so it sits in the mid-to-upper range for the Davenport resort market. The $1M+ segment is very thin, with just one active listing, meaning most inventory lands well below seven figures.
What do homes cost in Windsor Island?+
Expect a median list price around $630,000 and an average of about $210 per square foot, with a typical home measuring roughly 3,234 square feet. Over the last 12 months, 62 homes sold at a median price of $572,500, so closing prices tend to run below asking.
How is the market right now?+
There are 103 active listings and homes are taking a median of 120 days to sell, which points to a patient, buyer-leaning market. Sellers are averaging about 96% of their asking price, so there's room to negotiate on well-priced homes.
What are the HOA fees and property taxes like?+
The median HOA runs about $712 per month, which is substantial but typical for a gated resort community with shared amenities. Median property taxes come in around $9,670 per year, so factor both into your carrying costs — especially if you're running the home as a short-term rental.
What schools serve Windsor Island?+
The most commonly assigned schools are Loughman Oaks Elementary, Lake Alfred-Addair Middle School, and Ridge Community High School. Because this is primarily a vacation-rental community, always confirm the current zone with Polk County Public Schools before buying for a family move.
How is the commute from Windsor Island?+
Walt Disney World is about 30 minutes away, with Universal Orlando and Orlando International Airport (MCO) both around 46 minutes. Downtown Orlando is roughly 45 minutes, so the location favors theme-park access over a daily city commute.
Is there new construction in Windsor Island?+
Inventory here is mostly resale, with just one active new-construction listing at the moment. Most of the 103 active homes are existing resort-style properties, nearly all with private pools.
Keep exploring
More Davenport 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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