1559 SKYLINE DRIVE, KISSIMMEE, FL, 34744
Active1 days on marketListed Sep 26, 2026MLS #O6442242
About this home
1559 SKYLINE DRIVE
Welcome to 1559 Skyline Dr, Kissimmee, located in the desirable Harbour Oaks community! This spacious 4-bedroom, 3-bath pool home sits on approximately 0.34 acres and offers an impressive combination of indoor comfort, outdoor living, and valuable upgrades. Major improvements include a roof replaced in 2021, pool resurfaced in 2021, PAID-OFF solar panels, and a pool enclosure re-screened in 2025. The pool also features a hybrid heater with a dedicated solar panel, while a solar-powered attic fan provides an additional energy-conscious feature. Inside, you'll find an updated kitchen and bathrooms, generous living and dining areas, and a versatile floor plan ideal for everyday living and entertaining. Additional features include motorized window treatments and a central vacuum system. Step outside and enjoy Florida living with a screened pool and spa, spacious covered lanai, and fully fenced backyard surrounded by mature landscaping. The generous lot provides plenty of additional outdoor space and even includes a chicken coop. Location adds even more appeal. Harbour Oaks is conveniently situated near the growing NeoCity development, with easy access to shopping, dining, and major Central Florida roadways, and is approximately 30 minutes from Orlando International Airport (MCO). With approximately 0.34 acres, a pool and spa, paid-off solar panels, 2021 roof, updated kitchen and bathrooms, and numerous improvements, this home offers an exceptional combination of space, comfort, and functionality. Schedule your private showing today and discover everything 1559 Skyline Dr has to offer!
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
2,402
Sqft
0.34 ac
Lot size
2
Garage
1989
Year built
One
Levels
$271
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.
$4,305 /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
$4,305/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
+26.7%
$/sqft vs Kissimmee actives
$271 vs $209
Days on market
1 vs 51 typical
Where $271/sqft sits among the 400 Kissimmee actives
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.
Where it sits
Inside Harbour Oaks
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Kissimmee. See the full Kissimmee guide →
Harbour Oaks — neighborhood snapshot
Population
885
Median age
39
Median income
$136,012
Median home value
$419,200
Avg household
3
Households w/ children
128
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)
208 of 400
Kissimmee actives have cut their price
Median sold price, Kissimmee, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 73% above the KISSIMMEE 34744 median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 1559 SKYLINE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’26$540,000
1710 WOODSIDE COURT · same community
4 bd · 2 ba · 2,369 sqft · $228/sqft · 169 DOM
Sold · Jun ’26$620,000
1813 ADMIRAL COURT · same community
4 bd · 3 ba · 2,779 sqft · $223/sqft · 3 DOM
Sold · Mar ’26$515,000
1511 GRANDVIEW BOULEVARD · same community
3 bd · 2.5 ba · 1,981 sqft · $260/sqft · 152 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
Angela Rodriguez
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 1559 SKYLINE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1559 SKYLINE DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Angela's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1559 SKYLINE DRIVE FAQs
What would the monthly payment be for 1559 SKYLINE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,305/mo — principal and interest, the actual property-tax bill, the $17/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 1559 SKYLINE DRIVE?+
The association fee works out to $17 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 1559 SKYLINE DRIVE?+
The most recent tax bill on record (2025) was $4,526. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 1559 SKYLINE DRIVE?+
The listing reports pets: Yes. 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 $650,000, this home is listed about 73% above the Kissimmee median of $375,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1559 SKYLINE DRIVE?+
Neptune Middle School (middle), Osceola High School (high), Partin Settlement Elementary School (elementary) — Osceola County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Positioned at the premium end
$650,000 runs 73% above the KISSIMMEE 34744 median — but at 2,402 sqft it's also 32% larger than the typical Kissimmee listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Fresh on the market
Only 1 day on market in a Kissimmee market that averages 51 — if it fits, move quickly.
Keep looking
Similar homes nearby
Listing courtesy of NORKIS & CO REALTY · Jose Santana Feliciano. MLS #O6442242.
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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