Single Family Residence at 205 SURPRISE DR, WINTER GARDEN
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32 photos

$1,200,000

205 SURPRISE DR
WINTER GARDEN, FL 34787
Listed by RE/MAX PRIME PROPERTIES
Bedrooms
4
Bathrooms
2.5
Living area
2,171 sqft
Year built
1950

About this home

Welcome to Winter Garden, which has been ranked by Money Magazine "Best Places To Live In America" and is a finalist for Hallmark Channel's 2026 "Merriest Christmas Towns" Contest. This exceptional property in the heart of the 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. Priced to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. 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. A large shed, rated as a detached garage, 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. The 3/4 acre property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. SELLER WILL CONSIDER SUB-DIVIDINGTHE LOTS. 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.

Highlights

Private poolFireplace

Property details

MLS #
MFRO6365188
Property type
Single Family Residence
Subdivision
WINTER GARDEN SHORES REP
Status
Active
Days on market
245
On market date
December 4, 2025
Stories
N/A
Total bathrooms
2.5
Garage spaces
2
Parking spaces
N/A
Lot size
0.75 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
DILLARD STREET ELEMENTARY
0.26 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
528
Student:teacher ratio
16.0:1
District
ORANGE
Middle
LAKEVIEW MIDDLE
1.4 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
828
Student:teacher ratio
18.8:1
District
ORANGE
High
ORANGE TECHNICAL COLLEGE WESTSIDE CAMPUS
1.23 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
0
Student:teacher ratio
0.0:1
District
ORANGE

Walkability

Blended score for WINTER GARDEN's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

34
Car-dependent
out of 100
EPA National Walkability Index
7.2 / 20 -- Below average walkable
Google Places amenity density
30 / 100
Restaurants & cafes0
Grocery stores0
Parks3
Schools3
Transit stops0
Pharmacies0

Market position

How this listing compares to current activity in WINTER GARDEN, from live MLS data.

On the market 245 days -- 170 more days than WINTER GARDEN's current average of 75 days.
For reference, the median list price across 1,032 active listings in WINTER GARDEN right now is $489,070.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$7,377/mo
$240,000 down
$960,000 loan
Principal & interest$6,227
Property tax (est.)$1,000
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 19 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.