# 205 SURPRISE Drive, Winter Garden, FL 34787 > **TL;DR:** 4bd/3ba single family, $1,200,000 ($553/sqft), built 1950, 2,171 sqft. > Pool, Fireplace, A/C, 2-car garage. Est. $6,418/mo. Listed 334 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,200,000 | | Price/sqft | $553 | | Bedrooms | 4 | | Bathrooms | 2 full, 1 half | | Square Feet | 2,171 | | Year Built | 1950 | | Lot Size | 32,670 sqft (0.75 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 334 | ## Why This Home Stands Out - **Pool** - Porch, Patio ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $6,068 | | Estimated Insurance | $350 | | **Total** | **$6,418** | ## Nearby Schools - **Elementary:** Dillard Street Elem - **Middle:** Lakeview Middle - **High:** West Orange High ## Key Amenities - Pool - Fireplace - A/C - 2-car garage ## Property Highlights - Built in 1950 - 0.75 acre lot - Private pool - Fireplace ## Description ### Agent 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. ## Location - **Address:** 205 SURPRISE Drive, Winter Garden, FL 34787 - **County:** Orange - **Neighborhood:** WINTER GARDEN SHORES REP - **Coordinates:** 28.574354, -81.582838 - **Google Maps:** https://www.google.com/maps?q=28.574354,-81.582838 ## Virtual Tour & Media - **Video Tour:** https://www.propertypanorama.com/instaview/stellar/O6365188 ## Listing Agent - **Name:** Alison Scorsone - **Brokerage:** RE/MAX Prime Properties - **Broker Phone:** (407) 908-1440 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/205-Surprise-Dr_Winter-Garden_FL_34787_M54495-65820?f=listhub&s=MFRMLSFL&m=O6365188&c=propsimple) ## Photos ![205 SURPRISE Drive - Photo 1](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f451427629r.jpg) ![205 SURPRISE Drive - Photo 2](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f893131292r.jpg) ![205 SURPRISE Drive - Photo 3](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f205489662r.jpg) ![205 SURPRISE Drive - Photo 4](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f1101617345r.jpg) ![205 SURPRISE Drive - Photo 5](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f3761403365r.jpg) ![205 SURPRISE Drive - Photo 6](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f233686852r.jpg) ![205 SURPRISE Drive - Photo 7](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f3347755929r.jpg) ![205 SURPRISE Drive - Photo 8](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f2722940537r.jpg) ![205 SURPRISE Drive - Photo 9](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f2062369752r.jpg) ![205 SURPRISE Drive - Photo 10](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f226665420r.jpg) ![205 SURPRISE Drive - Photo 11](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f2990820165r.jpg) ![205 SURPRISE Drive - Photo 12](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f4222786050r.jpg) ![205 SURPRISE Drive - Photo 13](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f684195553r.jpg) ![205 SURPRISE Drive - Photo 14](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f676050885r.jpg) ![205 SURPRISE Drive - Photo 15](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f1167664715r.jpg) ![205 SURPRISE Drive - Photo 16](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f896129548r.jpg) ![205 SURPRISE Drive - Photo 17](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f2711420716r.jpg) ![205 SURPRISE Drive - Photo 18](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f2682398246r.jpg) ![205 SURPRISE Drive - Photo 19](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f3284905038r.jpg) ![205 SURPRISE Drive - Photo 20](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f4046352577r.jpg) ![205 SURPRISE Drive - Photo 21](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f949177569r.jpg) ![205 SURPRISE Drive - Photo 22](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f4057576956r.jpg) ![205 SURPRISE Drive - Photo 23](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f3596035484r.jpg) ![205 SURPRISE Drive - Photo 24](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f1913746725r.jpg) ![205 SURPRISE Drive - Photo 25](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f491557417r.jpg) ![205 SURPRISE Drive - Photo 26](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f111046341r.jpg) ![205 SURPRISE Drive - Photo 27](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f159377727r.jpg) ![205 SURPRISE Drive - Photo 28](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f3598480628r.jpg) ![205 SURPRISE Drive - Photo 29](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f1653518266r.jpg) ![205 SURPRISE Drive - Photo 30](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f1829328292r.jpg) ![205 SURPRISE Drive - Photo 31](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f1859147003r.jpg) ![205 SURPRISE Drive - Photo 32](http://lh.rdcpix.com/645ef17a032790ecfe18e23fc929e0d9l-f3656955815r.jpg) --- **MLS#:** O6365188 | **Updated:** 2026-10-30 **Source:** listhub *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.* [View on PropertySimple](https://www.propertysimple.ai/listing/205-surprise-drive-winter-garden-fl-34787-b2f4594c1dd048d58af9e8a6bd82d325) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/205-surprise-drive-winter-garden-fl-34787-b2f4594c1dd048d58af9e8a6bd82d325#listing", "url": "https://www.propertysimple.ai/listing/205-surprise-drive-winter-garden-fl-34787-b2f4594c1dd048d58af9e8a6bd82d325", "name": "205 SURPRISE Drive, 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. 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