205 SURPRISE DRIVE, WINTER GARDEN, FL, 34787
Active255 days on marketListed Dec 4, 2025MLS #O6365188
About this home
205 SURPRISE DRIVE
PRICE ADJUSTED to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. This property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.
Facts & features
The home at a glance
4
Bedrooms
2.5
Bathrooms
2,171
Sqft
0.75 ac
Lot size
2
Garage
1950
Year built
One
Levels
$553
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.
$7,369 /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
$7,369/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.
$/sqft vs Winter Garden actives
$553 vs $260
Days on market
255 vs 39 typical
Where $553/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 Winter Garden
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
WINTER GARDEN 34787 — neighborhood snapshot
Population
93,064
Median age
37.4
Median income
$114,988
Median home value
$475,000
Avg household
3.02
Households w/ children
13,499
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 → $630K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
198 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 127% 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 205 SURPRISE DRIVE
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Feb ’26$825,000
515 N BOYD STREET · same community
5 bd · 4 ba · 3,152 sqft · $262/sqft · 525 DOM
Sold · Mar ’26$743,148
417 S MAIN STREET
3 bd · 2.5 ba · 2,172 sqft · $342/sqft · 59 DOM
Sold · Apr ’26$640,000
337 SUNSET OAKS RD
4 bd · 3 ba · 2,186 sqft · $293/sqft · 3 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
Anthony Richardson
REALTOR® · CENTURY 21 Edge
Tours, negotiation, and every question about 205 SURPRISE DRIVE — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 205 SURPRISE DRIVE — before you fall in love.
See it in person
Schedule a tour
Live availability from Anthony's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
205 SURPRISE DRIVE FAQs
What would the monthly payment be for 205 SURPRISE DRIVE?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $7,369/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 205 SURPRISE DRIVE?+
The most recent tax bill on record (2024) was $3,406. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Garden?+
At $1,200,000, this home is listed about 105% above the Winter Garden median of $584,000. The market section on this page shows how the area is trending.
Which schools are assigned to 205 SURPRISE DRIVE?+
Sunridge Elementary (elementary), Sunridge Middle (middle), West Orange High (high) — 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
$1,200,000 runs 127% above the WINTER GARDEN 34787 median.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Time on market is leverage
255 days on market against a Winter Garden median of 39 — sellers in this position are usually ready to negotiate.
04Strong assigned schools
Sunridge Elementary, Sunridge Middle, West Orange High — Sunridge Middle rates 4 of 5. Always verify assignments with the district.
05The price has already moved
Listed at $1,300,000, now $1,200,000 — a $100K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of RE/MAX PRIME PROPERTIES · Alison Scorsone. MLS #O6365188.
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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