2183 TRIPOLI CT, KISSIMMEE, FL, 34747
Active388 days on marketListed Jul 13, 2025MLS #S5130786
About this home
2183 TRIPOLI CT
This spacious fully furnished 9-bedroom, 6-bathroom pool home is located in the sought-after Windsor at Westside Resort. One of the largest floor plans in the community, the home is ideal for large vacationing groups for investors and for your own pleasure. The open-concept floor plan features multiple living areas, a large upstairs loft/game room, and a modern kitchen with granite countertops, stainless steel appliances, and ample seating. The home includes themed bedrooms, generous sleeping capacity, and stylish furnishings throughout. The private screened-in pool and spa, complete with a covered lanai and outdoor dining area—perfect for relaxing or entertaining. Whether hosting guests or enjoying it personally, this outdoor space adds major rental appeal. Windsor at Westside offers resort-style amenities, including Clubhouse with restaurant and bar, with lazy river and water slide, fitness center, arcade, and sports courts, 24/7 manned security gate. With covered outdoor sitting, hot tub/spa, sand volley, basketball court, walking trails, store/ market place, it is Located only minutes from Walt Disney World! New laminate floors throughout the entire house! Come and take a look today!
Facts & features
The home at a glance
9
Bedrooms
6
Bathrooms
4,391
Sqft
0.13 ac
Lot size
2
Garage
2016
Year built
Two
Levels
$150
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.
$5,577 /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
$5,577/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
−8.3%
$/sqft vs WINDSOR AT WESTSIDE
$150 vs $194
Days on market
388 vs 53 typical
Where $150/sqft sits among the 15 homes for sale in WINDSOR AT WESTSIDE
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 at Westside, 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
$2,100/mo median
Live Kissimmee rental listing data — this home’s rate depends on size, condition and furnishing.
The Four Corners short-term market
▼ Softening48%
Occupancy
▼ 37% yr/yr
$325
Avg nightly rate
▲ 13% yr/yr
$38K/yr
Revenue per listing
$151
RevPAR
78 days
Booking lead time
5.7 nights
Avg stay
3
Typical min nights
11,479
Active rentals
▼ 20% supply
Seasonality — monthly occupancy
Peaks at 57% in Jul · bottoms at 36% in Jun
Last 12 months of data, January–December, bars scaled to the seasonal peak. Market-wide averages across all home sizes in Four Corners — the projection above is specific to this home’s size.
Where it sits
Inside Windsor At Waterside
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Windsor at Westside is a short-term-rental community. See the full guide →
Windsor At Waterside — neighborhood snapshot
Population
145
Median age
38
Median income
$101,226
Median home value
$429,800
Avg household
3
Households w/ children
7%
For the school run
Osceola County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Kissimmee market
$365K → $350K
Kissimmee median sold, yr/yr
97.3%
Sale-to-list ratio (12 mo)
3 of 15
WINDSOR AT WESTSIDE have cut their price
Median sold price, Kissimmee, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 65% above the KISSIMMEE 34747 median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 2183 TRIPOLI CT
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$580,000
1606 LIMA AVE COURT · same community
9 bd · 6 ba · 4,391 sqft · $132/sqft · 109 DOM
Sold · Mar ’26$653,000
8801 BENGAL COURT · same community
8 bd · 6 ba · 4,041 sqft · $162/sqft · 61 DOM
Sold · Mar ’26$550,000
8897 RHODES STREET · same community
6 bd · 4.5 ba · 3,142 sqft · $175/sqft · 7 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
Krystina Allen
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 2183 TRIPOLI CT — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2183 TRIPOLI CT — before you fall in love.
See it in person
Schedule a tour
Live availability from Krystina's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2183 TRIPOLI CT FAQs
What would the monthly payment be for 2183 TRIPOLI CT?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $5,577/mo — principal and interest, the actual property-tax bill, the $563/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 2183 TRIPOLI CT?+
The association fee works out to $563 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 2183 TRIPOLI CT?+
The most recent tax bill on record (2024) was $12,617. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Can 2183 TRIPOLI CT be rented short-term?+
Yes — this home sits inside Windsor at Westside, 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 2183 TRIPOLI CT?+
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 Kissimmee?+
At $659,000, this home is listed about 74% above the Kissimmee median of $379,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2183 TRIPOLI CT?+
Westside K-8 School (elementary), Celebration High School (high) — Osceola 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
$659,000 runs 65% above the KISSIMMEE 34747 median — but at 4,391 sqft it's also nearly 2 times the size of the typical Kissimmee listing.
02Zoned for nightly rentals
Windsor at Westside 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 $563/mo. That usually buys real services — verify what's covered before comparing this home against fee-free alternatives.
05Time on market is leverage
388 days on market against a Kissimmee median of 53 — sellers in this position are usually ready to negotiate.
Keep looking
Similar homes nearby
Listing courtesy of AAA GLOBAL VENTURES PA · Ann Yu. MLS #S5130786.
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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