2321 THE OAKS BOULEVARD, KISSIMMEE, FL, 34746
Active39 days on marketListed Sep 1, 2026MLS #S5156742
About this home
2321 THE OAKS BOULEVARD
Welcome to this spacious 5-bedroom, 3.5-bath pool home in The Oaks, offering 3,592 square feet of living space and peaceful golf course views. The thoughtfully designed floor plan features a first-floor primary suite, formal dining room, spacious family room, laundry room, half bath, and a well-appointed kitchen with new stainless steel appliances. A new HVAC system. Upstairs, you’ll find all-new carpet, a large loft with plenty of room for a game room, home gym, media space, or additional family room, plus a second primary suite with a private bath, three additional bedrooms, and a full guest bathroom. The backyard is where this home really stands out. Step outside to your private screened-in pool overlooking the golf course, surrounded by lush landscaping and wide-open green views—a beautiful setting for relaxing, entertaining, or enjoying Florida living year-round. Located in The Oaks, a scenic golf community surrounded by mature landscaping and expansive green spaces, the home also offers convenient access to shopping, dining, and entertainment at The Loop, Lake Tohopekaliga, and everything the Kissimmee area has to offer.
Facts & features
The home at a glance
5
Bedrooms
3.5
Bathrooms
3,592
Sqft
0.17 ac
Lot size
2
Garage
2002
Year built
Two
Levels
$155
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.
$4,420 /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
$4,420/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
+4.2%
$/sqft vs Kissimmee actives
$155 vs $204
Days on market
39 vs 89 typical
Where $155/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 The Oaks - Golf Community
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Kissimmee. See the full Kissimmee guide →
The Oaks - Golf Community — neighborhood snapshot
Population
1,216
Median age
47
Median income
$69,121
Median home value
$331,700
Avg household
3
Households w/ children
109
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)
213 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 66% above the KISSIMMEE 34746 median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 2321 THE OAKS BOULEVARD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’25$451,000
2260 THE OAKS BOULEVARD · same community
5 bd · 4 ba · 3,546 sqft · $127/sqft · 179 DOM
Sold · Aug ’26$545,000
2460 THE OAKS BOULEVARD · same community
5 bd · 3 ba · 3,416 sqft · $160/sqft · 327 DOM
Sold · Jun ’26$471,000
2622 ROUGHSIDE CIRCLE · same community
4 bd · 3 ba · 2,671 sqft · $176/sqft · 157 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
Donna Layton
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 2321 THE OAKS BOULEVARD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 2321 THE OAKS BOULEVARD — before you fall in love.
See it in person
Schedule a tour
Live availability from Donna's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
2321 THE OAKS BOULEVARD FAQs
What would the monthly payment be for 2321 THE OAKS BOULEVARD?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $4,420/mo — principal and interest, the actual property-tax bill, the $24/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 2321 THE OAKS BOULEVARD?+
The association fee works out to $24 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 2321 THE OAKS BOULEVARD?+
The most recent tax bill on record (2025) was $8,677. 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 2321 THE OAKS BOULEVARD?+
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 $555,000, this home is listed about 48% above the Kissimmee median of $375,000. The market section on this page shows how the area is trending.
Which schools are assigned to 2321 THE OAKS BOULEVARD?+
Pleasant Hill Elementary School (elementary), Horizon Middle School (middle), Liberty 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
$555,000 runs 66% above the KISSIMMEE 34746 median — but at 3,592 sqft it's also nearly twice the size of 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.
03The price has already moved
Listed at $561,900, now $555,000 — a $7K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of PROFESSIONAL REAL ESTATE TEAM · Diana Perez. MLS #S5156742.
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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