18339 OLIVER TWIST WAY, WINTER GARDEN, FL, 34787
Active563 days on marketListed Apr 3, 2025MLS #O6280496
About this home
18339 OLIVER TWIST WAY
Short Sale. *Motivated Seller* This 2023 built home has only had One-owner, highly upgraded luxury 4-bedroom, 3-bathroom home with 2-car garage, fenced-in oversized yard, and overhead storage in the highly desirable Waterleigh community—just minutes from Walt Disney World in the Top-Rated School zone. No lawn mower needed - the HOA maintains all lawn care in this beautiful community! This home is constructed Block on Block - top and bottom unlike many other builders who build wood frame on the second floor. Don't wait for a newly constructed home and pay more for a similar home... this one is ready now. This well-appointed home features a downstairs guest suite, upgraded wood-look tile (no carpet on the first floor), and a gourmet kitchen with 42” cabinets, quartz countertops, custom backsplash, large island, under-cabinet lighting, and premium LG stainless steel appliances, including a French door refrigerator with craft ice and Instaview. Additional features include an EV charging station, smart switches, custom lighting and fans throughout, and a covered lanai overlooking a spacious backyard. Upstairs offers a generous loft, two secondary bedrooms with walk-in closets, a full bathroom with dual sinks, a laundry room with LG washer and dryer on pedestals, and a luxurious primary suite with a tray ceiling, a spa-style bath, a frameless glass shower, a soaking tub, and an oversized walk-in closet. Oversized yard has plenty of space to build your own pool or you could enjoy the Waterleigh resort-style amenities with 3 pools, clubhouses, fitness centers, tennis courts, dog parks, playgrounds, putt-putt golf, fishing pier, walking trails, rock climbing, pickleball ball and a full calendar of social events. Just a couple of streets away, the 4th pool is under construction and will be completed shortly. Zoned for top-rated schools and offering convenient access to 429, 417, and 408. Many homeowners enjoy golf cart living in this community, where you can enjoy an abundance of amenities, social events, drop your little ones off at school, or do your grocery shopping; there's a daycare, elementary, and middle school, and a Publix located inside the community. This is a rare opportunity to own a move-in-ready, upgraded home in one of Winter Garden’s most popular neighborhoods!
Facts & features
The home at a glance
4
Bedrooms
3
Bathrooms
2,931
Sqft
0.15 ac
Lot size
2
Garage
2023
Year built
Two
Levels
$222
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.
$4,976 /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
$4,976/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
+0.4%
$/sqft vs Winter Garden actives
$222 vs $259
Days on market
563 vs 61 typical
Where $222/sqft sits among the 400 Winter Garden 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 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 → $611K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
214 of 400
Winter Garden actives have cut their price
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 30% above the WINTER GARDEN 34787 median. See the full Winter Garden market guide →
Paper trail
This home's history
Reality check
What actually sold near 18339 OLIVER TWIST WAY
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Jun ’26$700,000
18386 OLIVER TWIST WAY · same community
4 bd · 3 ba · 2,924 sqft · $239/sqft · 54 DOM
Sold · Jul ’26$809,000
18422 OLIVER TWIST WAY · same community
5 bd · 4.5 ba · 3,231 sqft · $250/sqft · 18 DOM
Sold · Sep ’26$762,000
18321 OLIVER TWIST WAY · same community
4 bd · 3.5 ba · 3,327 sqft · $229/sqft · 2 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
Kathy Miller
real estate agent · CENTURY 21 Edge
Tours, negotiation, and every question about 18339 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 18339 OLIVER TWIST WAY — before you fall in love.
See it in person
Schedule a tour
Live availability from Kathy's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
18339 OLIVER TWIST WAY FAQs
What would the monthly payment be for 18339 OLIVER TWIST WAY?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $4,976/mo — principal and interest, the actual property-tax bill, the $250/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 18339 OLIVER TWIST WAY?+
The association fee works out to $250 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 18339 OLIVER TWIST WAY?+
The most recent tax bill on record (2024) was $9,777. 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 18339 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 $650,000, this home is listed about 10% above the Winter Garden median of $592,495. The market section on this page shows how the area is trending.
Which schools are assigned to 18339 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
Five things that matter here
01Positioned at the premium end
$650,000 runs 30% above the WINTER GARDEN 34787 median — but at 2,931 sqft it's also 38% larger than the typical Winter Garden listing.
02Move-in furnished
The furniture conveys — a genuine head start for a second home or rental, and one less five-figure line item after closing.
03Time on market is leverage
563 days on market against a Winter Garden median of 61 — sellers in this position are usually ready to negotiate.
04Strong 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.
05The price has already moved
Listed at $790,000, now $650,000 — a $140K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of HAMLIN REALTY · Edward Guerrette LLC. MLS #O6280496.
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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