4404 SIMMONS ROAD, ORLANDO, FL, 32812
Active43 days on marketListed Jun 11, 2026MLS #O6410609
About this home
4404 SIMMONS ROAD
Welcome to this stunning pool home in the highly sought-after Conway area, one of Central Florida’s most desirable neighborhoods, with NO HOA. Beautifully maintained and situated on one of the largest lots in the community, this exceptional residence offers the perfect blend of comfort, style, and outdoor living. The home features 4 spacious bedrooms, 3 full bathrooms, a 3-car garage, and a cozy wood-burning fireplace. The expansive primary suite overlooks the pool, creating a peaceful retreat. Recent updates include solar panels, new spray foam insulation, and a new AC system. A unique highlight of this property is the attached private apartment with its own separate entrance, offering endless possibilities. This versatile space features a large living room, dining area, one bedroom, a full bathroom, and direct access to the backyard. Whether you're looking for an in-law suite, guest quarters, a private home office, a space for multi-generational living, or potential rental income, this flexible layout provides a rare opportunity to customize the space to fit your needs. The kitchenette area is currently being used as an office but can easily be converted back into a fully functional kitchen. The open-concept kitchen flows seamlessly into the family room, creating the perfect setting for everyday living and entertaining. Step outside to your private backyard oasis, complete with a large pool, a large fenced yard, and breathtaking Florida sunsets. Conveniently located near the Lake Conway Chain of Lakes, Orlando International Airport, Downtown Orlando, International Drive, Walt Disney World, and Universal Studios, this home provides easy access to Central Florida’s premier attractions, dining, shopping, and entertainment. Don't miss this rare opportunity to own a beautiful home that offers space, privacy, flexibility, and an unbeatable location in the heart of Conway.
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
3,424
Sqft
0.34 ac
Lot size
3
Garage
1992
Year built
One
Levels
$225
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 — not generic estimates.
$4,930 /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
$4,930/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
−32.2%
$/sqft vs Orlando actives
$225 vs $237
Days on market
43 vs 34 typical
Where $225/sqft sits among the 400 Orlando 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 Orlando
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Orlando. See the full Orlando guide →
ORLANDO 32812 — neighborhood snapshot
Population
34,454
Median age
37.8
Median income
$74,245
Median home value
$342,800
Avg household
2.45
Households w/ children
4,013
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Orlando market
$400K → $405K
Orlando median sold, yr/yr
97.0%
Sale-to-list ratio (12 mo)
149 of 400
Orlando actives have cut their price
Median sold price, Orlando, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 251% above the ORLANDO 32812 median. See the full Orlando market guide →
Paper trail
This home's history
Reality check
What actually sold near 4404 SIMMONS ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’25$1,700,000
5224 SAINT REGIS PLACE
4 bd · 3.5 ba · 3,472 sqft · $490/sqft · 128 DOM
Sold · Jun ’26$745,000
6506 FRANCONIA DRIVE
5 bd · 4.5 ba · 3,333 sqft · $224/sqft · 7 DOM
Sold · Nov ’25$740,000
3516 BATTERSEA COURT
5 bd · 3 ba · 3,284 sqft · $225/sqft · 61 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
Eric Chery
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 4404 SIMMONS ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 4404 SIMMONS ROAD — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to Eric's phone and CRM.
Straight answers
4404 SIMMONS ROAD FAQs
What would the monthly payment be for 4404 SIMMONS ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,930/mo — principal and interest, the actual property-tax bill 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.
What are the property taxes on 4404 SIMMONS ROAD?+
The most recent tax bill on record (2025) was $3,983. 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 4404 SIMMONS ROAD?+
The listing reports pets: Cats OK, Dogs OK. 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 Orlando?+
At $769,000, this home is listed about 97% above the Orlando median of $390,000. The market section on this page shows how the area is trending.
Which schools are assigned to 4404 SIMMONS ROAD?+
Shenandoah Elementary (elementary), Conway Middle (middle), William R Boone High (high) — Orange 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
$769,000 runs 251% above the ORLANDO 32812 median — but at 3,424 sqft it's also nearly twice the size of the typical Orlando 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 $779,000, now $769,000 — a $10K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of PREMIER PROPERTIES LLC · Amal Mazouzi. MLS #O6410609.
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.
Never miss a listing
New Orlando homes, in your inbox
Like 4404 SIMMONS ROAD but not quite? A daily digest of every new listing in Orlando — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Eric to ping you on any price or status change →