1944 THE OAKS BOULEVARD, KISSIMMEE, FL, 34746
Active39 days on marketListed Jun 29, 2026MLS #S5152726
About this home
1944 THE OAKS BOULEVARD
It’s summer time and this home is shining like it! See this beautiful 4 bedroom and 2 bath home nestled right in The Oaks golf community. The home boasts well over 2000 sq ft of living area, not including the huge back porch either! The owners went through great efforts to keep their home maintained and have made several renovations over some time. The kitchen is a big plus for our local chefs in the family and nobody will ever have to feel cramped. Theres an eat in breakfast nook or a full formal dining room. There’s more than enough space for everybody to feel comfortable. All common spaces are either ceramic tile or luxury vinyl plank. The bedrooms have carpets. The back yard is another highlight with pond views right from the patio and master bedroom window. Take in the tranquility of the sounds and views of nature while having a cup of coffee and reading a book. And if you get a little restless you can sign up for a game of golf right there in the community. Or maybe go across the street to the various famous restaurants, retail and shopping centers that abound if you choose. It’s all for you to enjoy! Come and set up an appointment to see this gem before it’s too late!
Facts & features
The home at a glance
4
Bedrooms
2
Bathrooms
2,288
Sqft
0.36 ac
Lot size
2
Garage
2003
Year built
One
Levels
$178
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.
$3,321 /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
$3,321/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
+3.5%
$/sqft vs Kissimmee actives
$178 vs $209
Days on market
39 vs 52 typical
Where $178/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)
169 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 17% above the KISSIMMEE 34746 median. See the full Kissimmee market guide →
Paper trail
This home's history
Reality check
What actually sold near 1944 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 · Apr ’26$405,000
1965 FAIRWAY LOOP · same community
4 bd · 3 ba · 2,581 sqft · $157/sqft · 6 DOM
Sold · Dec ’25$309,000
2109 EAGLEVIEW COURT · same community
3 bd · 2 ba · 1,958 sqft · $158/sqft · 7 DOM
Sold · Dec ’25$340,000
2141 THE OAKS BOULEVARD · same community
3 bd · 2 ba · 1,839 sqft · $185/sqft · 83 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 1944 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 1944 THE OAKS BOULEVARD — 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
1944 THE OAKS BOULEVARD FAQs
What would the monthly payment be for 1944 THE OAKS BOULEVARD?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,321/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 1944 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 1944 THE OAKS BOULEVARD?+
The most recent tax bill on record (2025) was $6,667. 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 1944 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 $407,900, this home is listed about 8% above the Kissimmee median of $379,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1944 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
$407,900 runs 17% above the KISSIMMEE 34746 median — but at 2,288 sqft it's also 26% larger than the typical Kissimmee listing.
02Waterfront living
This home sits directly on the water — the single scarcest feature in Florida inventory and the strongest long-term value anchor.
03The price has already moved
Listed at $439,900, now $407,900 — a $32K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of PRESTIGE REALTY GROUP LLC · Glenn Stewart. MLS #S5152726.
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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