205 Surprise Dr,WINTER GARDEN, FL 34787
WINTER GARDEN, FL 34787
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.
Details
| MLS # | O6365188 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | For-sale |
| Status | Active |
| Year | 1950 |
| Days On Site | 317 |
| Listing Provided By | RE/MAX PRIME PROPERTIES | Alison Scorsone |
Features
| Bed(s) | 4 |
|---|---|
| Bath(s) | 3 Total |
| SQ Feet | 2,171 |
| Garage | 2 |
| Pool | Yes |
| Story(s) | 1 |
| Zoning | R-1 |
| Acreage | 0.75 |
Taxes
| Property | 3406 |
|---|
Area Information
| State | FL |
|---|---|
| County | Orange |
| City | WINTER GARDEN |
| Zip Code | 34787 |
| Area | 34787 Winter Garden | Oakland |
| Community Name | WINTER GARDEN SHORES REP |
| School District | West Orange High |
| Elementary School | Dillard Street Elem |
| High School | West Orange High |
| Listing VS Median (in WINTER GARDEN SHORES REP) | |
Price: $1,200,000 low | high Med: $699,250 sqft: 2,171 low | high Med: 2,560 $ / sqft: $553 low | high Med: $282 On site: 317 low | high Med: 27.5 | |
Market Activity 34787
Request a showing
Request a showing
Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of October 17, 2026 at 5:59:15 PM PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.
Contact
Learn More About This Property
| State | FL |
|---|---|
| County | Orange |
| City | WINTER GARDEN |
| Zip Code | 34787 |
| Area | 34787 Winter Garden | Oakland |
| Community Name | WINTER GARDEN SHORES REP |
| School District | West Orange High |
| Elementary School | Dillard Street Elem |
| High School | West Orange High |
| Listing VS Median (in WINTER GARDEN SHORES REP) | |
Price: $1,200,000 low | high Med: $699,250 sqft: 2,171 low | high Med: 2,560 $ / sqft: $553 low | high Med: $282 On site: 317 low | high Med: 27.5 | |
Listings courtesy of Stellar MLS as distributed by MLS GRID.Based on information submitted to the MLS GRID as of All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.
