18344 OLIVER TWIST WAY, WINTER GARDEN, FL, 34787
Pending234 days on marketListed Dec 22, 2025MLS #S5140531
About this home
18344 OLIVER TWIST WAY
Short Sale. Beautiful home located in one of Winter Garden’s most prestigious communities, Waterleigh. This property offers conservation views, no rear neighbors, and a fully fenced backyard, providing privacy and tranquility. Features include brick exterior, no carpet throughout, a whole-house water filtration system, and innovative stairway lighting that activates as you walk, guiding each step with modern design and added safety. The gourmet kitchen is ideal for everyday living and entertaining. The layout offers 4 bedrooms and 3 full bathrooms, two spacious living areas, one on the main level and a large upstairs family room, plus a versatile loft. Waterleigh offers spectacular resort-style amenities, including three large pools, fitness center, multiple event and clubhouse spaces, as well as schools and shopping within the community. An exceptional opportunity in a highly desirable residential area.
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
2,924
Sqft
0.17 ac
Lot size
2
Garage
2023
Year built
Two
Levels
$226
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.
$4,411 /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
$4,411/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
−7.4%
Days on market
234 vs 40 typical
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 Hickory Hut
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
Hickory Hut — neighborhood snapshot
Population
5,306
Median age
38
Median income
$152,813
Median home value
$545,824
Avg household
3
Households w/ children
664
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Garden market
$585K → $626K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 25% above the WINTER GARDEN 34787 median. See the full Winter Garden market guide →
Paper trail
This home's history
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
Tyler Stoddard
REALTOR · CENTURY 21 Edge
Tours, negotiation, and every question about 18344 OLIVER TWIST WAY — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 18344 OLIVER TWIST WAY — before you fall in love.
See it in person
Schedule a tour
Live availability from Tyler's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
18344 OLIVER TWIST WAY FAQs
What would the monthly payment be for 18344 OLIVER TWIST WAY?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,411/mo — principal and interest, the actual property-tax bill, the $300/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 18344 OLIVER TWIST WAY?+
The association fee works out to $300 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 18344 OLIVER TWIST WAY?+
The most recent tax bill on record (2024) was $1,706. 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 18344 OLIVER TWIST WAY?+
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 Winter Garden?+
At $660,000, this home is listed about 13% above the Winter Garden median of $584,500. The market section on this page shows how the area is trending.
Which schools are assigned to 18344 OLIVER TWIST WAY?+
Water Spring Elementary (elementary), Horizon High School (high), Water Spring Middle School (middle) — Orange 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
$660,000 runs 25% above the WINTER GARDEN 34787 median — but at 2,924 sqft it's also 36% larger than the typical Winter Garden listing.
02Time on market is leverage
234 days on market against a Winter Garden median of 40 — sellers in this position are usually ready to negotiate.
03Strong assigned schools
Water Spring Elementary, Horizon High School, Water Spring Middle School — Horizon High School rates 4 of 5. Always verify assignments with the district.
04The price has already moved
Listed at $789,990, now $660,000 — a $130K cut. The full history is in the market section below.
Listing courtesy of LA ROSA REALTY LLC · Jacqueline Cepeda. MLS #S5140531.
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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