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Overview

4 bd3 ba2,171 sqft2 car garageSingle Family
TypeSingle Family
HOANone listed
Built1950
Lot32,697 sqft
Living area2,171 sqft
Price / sqft$553
Garage2 car

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Built-in FeaturesHigh CeilingsLiving Room/Dining Room ComboPrimary Bedroom Main FloorSolid Wood CabinetsThermostatWindow TreatmentsFire Pit

205 Surprise Dr is a 1950-built home in Winter Garden Shores Rep, Winter Garden. Inside you'll find 4 bedrooms, 3 bathrooms, and 2,171 square feet of living space. Listed at $1,200,000 (about $553/sqft), 245 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

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.

The essentials

Built
1950
Price / sqft
$553
On market
313 days
Annual tax
$3,406
Flood zone
X · Low risk
Lot
32,697 sqft
Type
Single Family Residence

At a glance

Single family
Built 1950
Private pool
Heated
2 car garage
0.75 acres
Lot size
2,171 sqft
Living area

Payment

Est. monthly payment
$7,142/mo
Down payment (20%)
$240,000
Property taxes
$284/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1950
Lot
32,697 sqft
Cooling
Central Air
Heating
Central, Electric
Parking
-
Pool
Heated, In Ground, Pool Sweep, Salt Water
Days on Market
313
Built-in Features
High Ceilings
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Solid Wood Cabinets
Thermostat
Window Treatments
Fire Pit
Garden
Private Mailbox
Storage
Cooktop
Dishwasher
Dryer
Microwave
Refrigerator
Washer
Elementary
Dillard Street Elem
Middle
Lakeview Middle
High
West Orange High

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on file Flood Zone X
Annual Tax (2024)
$3,406
Parcel #
14-22-27-9392-01-330

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Winter Garden Shores Rep
County
Orange
MLS Area
34787 - Winter Garden/Oakland
Lot Size
32,697 sqft
Corner LotCity LimitsLandscapedOversized LotPaved

Price history

Date
Event
Price
2/25/2026
Price change
Source: Stellar MLS #O6365188
$1,200,000-7.7%
$553/sqft
12/1/2025
Listed for sale
Source: Stellar MLS #O6365188
$1,300,000
$599/sqft

Neighborhood

205 Surprise Dr
Winter Garden, FL, 34787 · 34787 - Winter Garden/Oakland

Market insights

Offer Insights

Choose an offer strength

List price: $1,200,000
$1.19M – $1.20M
99.5% – 100% of listTops out right at the list price
80% of listList price
222 of the last 443 home closings in 34787 landed at this number or higher (50%). The median one sat 22 days before it went under contract, and this one is on day 313 after a $100,000 cut.

Sample: 443 closed home sales in 34787 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$7,142/mo
Principal & interest$6,258
Property taxes$284
Insurance$600
Down payment20% · $240,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$1,200,000

$553 per sq ft

Beds and baths

4 beds, 3 baths

Size

2,171 sq ft

Time on market

313 days

Year built

1950

Monthly payment

About $7,142/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $3,406 annual tax bill, insurance.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byRE/MAX PRIME PROPERTIESListing agent: Alison ScorsoneListing data from Stellar MLS, MLS# O6365188.

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