CENTURY 21 Edge
$2,495,0004 bd3.5 ba3,667 sqft$680 /sqft≈$15,513 /mo all-in ↓

8398 HAPPY TRAIL, KISSIMMEE, FL, 34747

Active184 days on marketListed Apr 9, 2026MLS #O6396464

Single Family ResidenceHAPPY TRAILS UNITS 1 & 2 UNREC

About this home

8398 HAPPY TRAIL

Custom-Built 2024 Private 5-Acre Estate. High & Dry in Gated Happy Trails. Welcome to a rare opportunity to own this exceptional estate situated on 5 pristine high-and-dry acres, one of the highest elevations within the community. Positioned on a desirable corner lot with dual gated entrances, the property offers enhanced accessibility, privacy, and flexibility for a variety of uses. Ideally located just minutes from Celebration, Reunion, and Walt Disney World, this exceptional property offers the perfect balance of luxury, privacy, and convenience with no HOA. A long, elegant private driveway leads to this impressive residence featuring 4 bedrooms, 3.5 bathrooms, an oversized 3-car garage with EV charging outlet, and a thoughtfully designed open-concept modern floor plan with expansive living spaces throughout. Step inside to experience soaring 14-foot ceilings throughout the entire home, enhanced by tray ceilings in the dining room, living room, and primary suite, along with a striking 16-foot cathedral ceiling in the designer kitchen, creating a bright and dramatic architectural presence. The gourmet kitchen is a true centerpiece, showcasing an oversized island with Italian granite, extensive custom cabinetry, a hidden oversized walk-in pantry, and a seamless connection to the main living and dining areas, ideal for both everyday living and entertaining. The elegant dining room features a stunning double glass-door wine display, while a beautifully designed wet bar with wine cooler adds both style and functionality. The spacious living area is anchored by a modern built-in electric fireplace with custom finishes. The breakfast area is framed by oversized picture windows, offering beautiful views of mature oak trees and the natural landscape, creating a serene, park-like setting. The luxurious primary suite offers a spa-inspired bathroom featuring a freestanding soaking tub positioned beneath a large picture window, a walk-in glass shower, and refined finishes that create a true retreat experience. All additional bedrooms are generously sized and designed for comfort and privacy. Outdoor living is equally impressive, featuring a covered lanai with a fully equipped outdoor kitchen, extensive paved areas, and expansive open acreage surrounded by beautiful mature trees. Zoned for horses, the property offers ample room for a barn, workshop, RV storage, or future additions. Additional features include double-glazed energy-efficient windows, premium modern motorized blinds throughout the entire home, large sliding glass doors, a private water well eliminating monthly water costs, and a seven-zone irrigation system.

Facts & features

The home at a glance

4

Bedrooms

3.5

Bathrooms

3,667

Sqft

5.01 ac

Lot size

3

Garage

2024

Year built

One

Levels

$680

Per sqft

FireplaceTrees/Woods viewNegotiablePets allowed

Inside

FlooringLuxury Vinyl · Porcelain Tile
AppliancesBuilt-In Oven · Dishwasher · Disposal · Dryer · Electric Water Heater · Exhaust Fan · Ice Maker · Microwave · Range · Range Hood · Refrigerator · Washer · Wine Refrigerator
InteriorCathedral Ceiling(s) · Ceiling Fan(s) · Eating Space In Kitchen · High Ceilings · Kitchen/Family Room Combo · Open Floorplan · Primary Bedroom Main Floor · Smart Home · Solid Wood Cabinets · Stone Counters · Tray Ceiling(s) · Walk-In Closet(s) · Wet Bar · Window Treatments
LaundryElectric Dryer Hookup · Laundry Room · Washer Hookup
CoolingCentral Air · Zoned
HeatingCentral · Exhaust Fan · Heat Pump · Zoned
FurnishedNegotiable

Outside & construction

RoofConcrete · Tile
ConstructionBlock · Stucco
FoundationSlab
ViewTrees/Woods
FacesNorth
ParkingDriveway · Electric Vehicle Charging Station(s) · Garage Door Opener · Garage Faces Side · Golf Cart Parking · Ground Level · Guest · Oversized
ExteriorAwning(s) · Garden · Irrigation System · Lighting · Outdoor Grill · Outdoor Kitchen · Private Entrance · Rain Gutters · Sliding Doors

Community & fees

HOA fee$50/mo
Taxes (2025)$10,852/yr
PetsYes
CommunityHorses Allowed

Utilities & systems

UtilitiesCable Connected · Electricity Connected · Public · Water Connected
WaterPrivate · Well

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.

$15,513 /mo · 10% down Conventional, 30-yr fixed at 6%

Principal & interest$13,463
PMI (est., until 20% equity)$936
Property tax — 2025 actual bill$904
HOA fee — from the listing$50
Insurance (FL estimate)$160

The assumptions

Loan typeConventionalDown payment10% · $249,500Loan30-yr fixed at 6%Mortgage insuranceIncludedTaxesActual bill on recordInsuranceFlorida estimate

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

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Run your own numbers

Loan type

FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.

Down payment10% · $249,500
Interest rate6.00%
Loan term

Estimated payment

$15,513/mo

Principal & interest$13,463
PMI (est., until 20% equity)$936
Property taxes (actual bill)$904
HOA / condo fee$50
Est. insurance$160

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.

List $2.5M
$1.1MedgeAI estimate $1,312,564 · range $1.2M–$1.4M$2.6M

vs edgeAI estimate

+90.1%

$/sqft vs Kissimmee actives

$680 vs $204

Days on market

184 vs 89 typical

Where $680/sqft sits among the 400 Kissimmee actives

309
75
8
1
2
5 · this home
$151–239$239–328$328–416$416–504$504–592$592+

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 Happy Trails

Drive times from this address

Walt Disney World≈ 18 min
Universal Orlando≈ 28 min
Downtown Orlando≈ 34 min
Orlando Int’l Airport (MCO)≈ 39 min
Downtown Tampa≈ 67 min

Estimated driving times, typical traffic. Data © OpenStreetMap contributors.

Get to know Kissimmee. See the full Kissimmee guide →

Happy Trails — neighborhood snapshot

Population

563

Median age

41

Median income

$90,203

Median home value

$447,202

Avg household

2

Households w/ children

29%

For the school run

Osceola County School District

ElementaryWestside K-8 School★★★★★
HighCelebration High School★★★★★

School assignments and ratings via edgeAI — always verify with the district.

The numbers that matter

The Kissimmee market

Seller’s marketLeans buyer — 7.1 months of inventoryBuyer’s market

$365K → $350K

Kissimmee median sold, yr/yr

97.3%

Sale-to-list ratio (12 mo)

212 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 538% above the KISSIMMEE 34747 median. See the full Kissimmee market guide →

Paper trail

This home's history

Apr 9, 2026Listed at $2,495,000 · 184 days on market since
2024Built · HAPPY TRAILS UNITS 1 & 2 UNREC

Reality check

What actually sold near 8398 HAPPY TRAIL

Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.

200 N GOODMAN ROADSold · Sep ’26

$1,700,000

200 N GOODMAN ROAD · same community

5 bd · 4.5 ba · 4,179 sqft · $407/sqft · 96 DOM

8310 HAPPY TRAILSSold · Jan ’26

$760,000

8310 HAPPY TRAILS · same community

3 bd · 2 ba · 2,660 sqft · $286/sqft · 143 DOM

305 HARGROVE LANESold · Mar ’26

$700,000

305 HARGROVE LANE · same community

3 bd · 2 ba · 2,072 sqft · $338/sqft · 89 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.

Zack Zonker

Your agent

Zack Zonker

President Tampa Division · CENTURY 21 Edge

Tours, negotiation, and every question about 8398 HAPPY TRAIL — start here.

Andrew Acosta

Your lender

Andrew Acosta

Acosta Home Loans with PRMG · NMLS #1468866

Pre-approval, rates, and the real monthly number for 8398 HAPPY TRAIL — before you fall in love.

See it in person

Schedule a tour

Live availability from Zack's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.

Straight answers

8398 HAPPY TRAIL FAQs

What would the monthly payment be for 8398 HAPPY TRAIL?+

With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $15,513/mo — principal and interest, the actual property-tax bill, the $50/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 8398 HAPPY TRAIL?+

The association fee works out to $50 per month. Ask us for the full association documents — they spell out exactly what the fee covers.

What are the property taxes on 8398 HAPPY TRAIL?+

The most recent tax bill on record (2025) was $10,852. 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 8398 HAPPY TRAIL?+

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 $2,495,000, this home is listed about 565% above the Kissimmee median of $375,000. The market section on this page shows how the area is trending.

Which schools are assigned to 8398 HAPPY TRAIL?+

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

Three things that matter here

01Positioned at the premium end

$2,495,000 runs 538% above the KISSIMMEE 34747 median — but at 3,667 sqft it's also nearly twice the size of the typical Kissimmee listing.

02Trees/Woods views

The trees/woods view is part of what you're buying — views hold value independently of the structure.

03Time on market is leverage

184 days on market against a Kissimmee median of 89 — sellers in this position are usually ready to negotiate.

Listing courtesy of FUTURE HOME REALTY INC · Robert McDugald. MLS #O6396464.

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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