1495 SKYLINE DRIVE, KISSIMMEE, FL, 34744
Active141 days on marketListed Mar 6, 2026MLS #S5145209
About this home
1495 SKYLINE DRIVE
Virtually Staged. SELLER ASSISTING WITH BUYER FINANCING, 2/1 BUYDOWN ON THE INTEREST RATE! Welcome to this wonderful 3-bedroom, 2-bathroom completely renovated home offering nearly 2100 sq. ft. of living space in the highly desirable Harbour Oaks community in Kissimmee, Florida. This spacious residence is designed for both comfort and style, featuring an open-concept layout, modern finishes, and thoughtful upgrades throughout. This renovation includes NEW Roof-Soffits-Gutters, Interior and Exterior Paint, both Bathrooms and Kitchen rehabs with Quartz Stone counters, SS Appliances, Breakfast Bar, Wet Bar, Luxury Vinyl Flooring, Blinds and Ceiling Fans throughout, Pool Refinished, Painted Decks front and back, Wood Burning Fireplace, Oversized 2-Car Garage, Pool Gazebo and Vinyl Fenced backyard. Enjoy your own private outdoor oasis with a sparkling pool and huge back yard—perfect for year-round Florida living and entertaining. Located just minutes from Historic Downtown Kissimmee, you'll have convenient access to shopping, dining, and entertainment. You're also perfectly positioned with a quick commute the Florida Turnpike, Lake Nona Medical City, major theme parks, schools, shopping and dining and the stunning Space Coast beaches. With its generous floor plan, multiple living areas, and every exceptional upgrade, this remarkable home has it all. Don’t miss your chance—schedule your showing today!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
2,094
Sqft
0.37 ac
Lot size
2
Garage
1973
Year built
One
Levels
$224
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.
$3,600 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
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
Estimated payment
$3,600/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. 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
−12.7%
$/sqft vs Kissimmee actives
$224 vs $209
Days on market
141 vs 45 typical
Where $224/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
$369K → $358K
Kissimmee median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
163 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 21% above the KISSIMMEE 34744 median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 1495 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 · Mar ’26$515,000
1511 GRANDVIEW BOULEVARD · same community
3 bd · 2.5 ba · 1,981 sqft · $260/sqft · 152 DOM
Sold · Aug ’25$469,000
1544 REGAL COURT · same community
3 bd · 2 ba · 1,844 sqft · $254/sqft · 5 DOM
Sold · Apr ’26$395,000
1575 SKYLINE DRIVE · same community
3 bd · 2 ba · 1,716 sqft · $230/sqft · 91 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
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 1495 SKYLINE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1495 SKYLINE DRIVE — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
1495 SKYLINE DRIVE FAQs
What would the monthly payment be for 1495 SKYLINE DRIVE?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,600/mo — principal and interest, the actual property-tax bill, the $16/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 1495 SKYLINE DRIVE?+
The association fee works out to $16 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 1495 SKYLINE DRIVE?+
The most recent tax bill on record (2025) was $5,404. 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 1495 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 $469,900, this home is listed about 24% above the Kissimmee median of $379,850. The market section on this page shows how the area is trending.
Which schools are assigned to 1495 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
Four things that matter here
01Positioned at the premium end
$469,900 runs 21% above the KISSIMMEE 34744 median — but at 2,094 sqft it's also 15% 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.
03Time on market is leverage
141 days on market against a Kissimmee median of 45 — sellers in this position are usually ready to negotiate.
04The price has already moved
Listed at $534,900, now $469,900 — a $65K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of MACERA REALTY GROUP INC · Peter MacEra. MLS #S5145209.
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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