About This Home

This 4-bedroom, 3-bathroom single family at 205 SURPRISE Drive in Winter Garden, FL is listed for $1,200,000 ($553 per sqft). Built in 1950, the home offers 2,171 sqft of living space on a 0.75 acres lot.

Key Features

  • Built in 1950
  • 0.75 acre lot
  • Private pool
  • Fireplace

Property Details

1 story
2 full, 1 half
2-car garage
1950

Amenities

PoolFireplaceA/C
Listing Description

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.

Monthly Cost Estimate

$6,418/mo

20% down · 6.5% · 30 years

Principal$868
Interest$5,200
Insurance$350

Estimates only. Actual payments may vary.

Location

205 SURPRISE Drive

Winter Garden, FL 34787

WINTER GARDEN SHORES REP

Features & Amenities

Interior Features

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

Exterior Features

Fire PitGardenPrivate MailboxStorage

Property Details

Flooring

Tile - CeramicWood

Construction

Block

Pool Features

Pool

Outdoor Features

PorchPatio

Heating

Electric (Heating)Central

Cooling

Central Air

Appliances

CooktopDishwasherDryerMicrowaveRefrigeratorWasher

Questions & Answers

This 4-bedroom, 3-bathroom single family at 205 SURPRISE Drive is listed at $1,200,000 ($553/sqft). The estimated monthly payment is $6,418 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1950, 0.75 acre lot, Private pool, Fireplace. Interior Features: Built-in Features, High Ceilings, Living Room/Dining Room Combo. Exterior Features: Fire Pit, Garden, Private Mailbox.

This property is listed by Alison Scorsone.

AS

Alison Scorsone

Agent at RE/MAX Prime Properties

Listed by RE/MAX Prime Properties · Broker phone: (407) 908-1440 · View on Broker Site · Broker website

MLS# O6365188· Source: Stellar MLS· 333 days on PropertySimple

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

205 SURPRISE Drive, Winter Garden, FL 34787

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