4450 KAIPO ROAD, DAVENPORT, FL, 33897
Active249 days on marketListed Dec 6, 2025MLS #O6365374
About this home
4450 KAIPO ROAD
This is the one investors wait for — a proven, high-occupancy vacation home in Windsor Island Resort with professionally themed rooms, a sun-drenched south-facing pool, and a price that makes the decision easy. The 6-bedroom, 4.5-bath Hideaway floor plan at 4450 Kaipo Road has earned its reputation as a guest favorite, and now it's available at a price that opens the door wide for the next owner. Inside, 3,117 sq. ft. of bright, open living space does exactly what a great vacation home should — it pulls people together. A sleek contemporary kitchen with large island seating, a spacious gathering room, and a dedicated dining area flow seamlessly together on the main floor, while the first-floor owner's suite offers a private retreat away from the energy of the main living areas. The upstairs is built for unforgettable group stays. A Mickey Mouse room, a Frozen-inspired suite, and a Harry Potter-styled bedroom — all professionally themed — are the kind of spaces guests search for specifically, book for, and rave about afterward. The expansive loft adds a second living and entertainment hub complete with pool table and oversized sectional, giving every guest their own corner of the house to claim. Outside, the south-facing heated pool and spa deliver all-day Florida sunshine onto a lanai built for long, lazy afternoons and evenings that drift well past sunset. This is the kind of outdoor setup guests actively seek. And then there's Windsor Island Resort itself — the Hawaiian-inspired community that continues to set the bar for vacation living near Disney. Tropical waterpark-style pool, lazy river, splash zone, water slides, outdoor dining, fitness facilities, sports courts, firepit lounge, and a signature clubhouse that delivers island energy from the moment you arrive. Walt Disney World is just minutes away. Aloha! Proven occupancy. Iconic themed rooms. South-facing pool. Windsor Island Resort. And a price that reflects a genuine opportunity — not a compromise. Be sure to check out the lifestyle video included with this listing. All information, including room dimensions, is deemed reliable but not guaranteed. Buyers and buyers agents are encouraged to verify all details independently.
Facts & features
The home at a glance
6
Bedrooms
4.5
Bathrooms
3,117
Sqft
0.11 ac
Lot size
2
Garage
2023
Year built
Two
Levels
$191
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record and the real association fee — not generic estimates.
$5,087 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$5,087/mo
Includes estimated PMI — it drops off once you reach 20% equity. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−6.9%
$/sqft vs WINDSOR ISLAND RESIDENCE PH 3
$191 vs $216
Days on market
249 vs 56 typical
Where $191/sqft sits among the 19 homes for sale in WINDSOR ISLAND RESIDENCE PH 3
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
The investor lens
Two ways this home pays
This home sits inside Windsor Island, a community zoned to allow true short-term rentals — so it can earn as a nightly rental or a traditional lease. Here’s how the two paths compare.
Short-term rental
Zoned & eligible
Projected nightly rate, occupancy and annual revenue for this exact home.
Long-term rental
$2,298/mo median
Live Davenport rental listing data — this home’s rate depends on size, condition and furnishing.
Where it sits
Inside Windsor Island
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Windsor Island is a short-term-rental community. See the full guide →
DAVENPORT 33897 — neighborhood snapshot
Population
29,206
Median age
38.9
Median income
$73,457
Median home value
$279,100
Avg household
2.85
Households w/ children
3,278
For the school run
Polk County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Davenport market
$350K → $370K
Davenport median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
9 of 19
WINDSOR ISLAND RESIDENCE PH 3 have cut their price
Median sold price, Davenport, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 76% above the DAVENPORT 33897 median. See the full Davenport market guide →
Paper trail
This home's history
Reality check
What actually sold near 4450 KAIPO ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jul ’26$630,000
4057 LANA AVENUE · same community
7 bd · 5.5 ba · 3,281 sqft · $192/sqft · 100 DOM
Sold · Aug ’26$670,000
3919 LANA AVENUE · same community
7 bd · 5.5 ba · 3,294 sqft · $203/sqft · 23 DOM
Sold · Aug ’25$449,000
4190 LANA AVENUE · same community
5 bd · 4.5 ba · 2,283 sqft · $197/sqft · 213 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
Julian Rivera
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 4450 KAIPO ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 4450 KAIPO ROAD — before you fall in love.
See it in person
Schedule a tour
Live availability from Julian's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
4450 KAIPO ROAD FAQs
What would the monthly payment be for 4450 KAIPO ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,087/mo — principal and interest, the actual property-tax bill, the $702/mo association fee and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
How much are the HOA fees at 4450 KAIPO ROAD?+
The association fee works out to $702 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 4450 KAIPO ROAD?+
The most recent tax bill on record (2024) was $9,421. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Can 4450 KAIPO ROAD be rented short-term?+
Yes — this home sits inside Windsor Island, a community zoned to allow short-term rentals. Nightly-rental income could change the math on this purchase entirely; request a free rental income analysis and our team will prepare projections for this exact home.
Are pets allowed at 4450 KAIPO ROAD?+
The listing reports pets: Breed Restrictions. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Davenport?+
At $596,000, this home is listed about 53% above the Davenport median of $389,970. The market section on this page shows how the area is trending.
Which schools are assigned to 4450 KAIPO ROAD?+
Loughman Oaks Elementary School (elementary), Ridge Community High School (high), Lake Alfred Polytech Academy (middle) — Polk County School District. Always verify school assignments with the district before relying on them.
The brief
Five things that matter here
01Positioned at the premium end
$596,000 runs 76% above the DAVENPORT 33897 median — but at 3,117 sqft it's also 59% larger than the typical Davenport listing.
02Zoned for nightly rentals
Windsor Island is one of the communities zoned to allow true short-term rentals — nightly income could change the math on this purchase entirely. Ask for the free rental analysis below.
03Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
04Know the monthly fee
The association fee is $702/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
05Time on market is leverage
249 days on market against a Davenport median of 56 — sellers in this position are usually ready to negotiate.
Keep looking
Similar homes nearby
Listing courtesy of FATHOM REALTY FL LLC · Susan Benante, Llc. MLS #O6365374.
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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