Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden’s most exciting and rapidly growing areas. Whether you’re looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience.
Inside, you’ll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you’ll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.
Inside, you’ll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you’ll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.
Property Details
Price:
$410,000
MLS #:
O6412414
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OVERSTREET CRATE
Neighborhood:
34787wintergardenoakland
Listed Date:
Jun 1, 2026
Finished Sq Ft:
1,616
Total Sq Ft:
1,616
Lot Size:
8,440 sqft / 0.19 acres (approx)
Year Built:
1950
See this Listing
Schools
Elementary School:
Maxey Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Dishwasher, Microwave, Range, Refrigerator
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Luxury Vinyl
Heating
Central
Interior Features
Kitchen/Family Room Combo, Stone Counters, Vaulted Ceiling(s)
Laundry Features
Other
Levels
One
Exterior
Construction Materials
Stucco, Wood Frame
Direction Faces
North
Exterior Features
Lighting, Other
Fencing
Fenced, Vinyl
Roof
Shingle
Financial
Tax Year
2025
Taxes
$5,517
Map
Community
- Address420 E CYPRESS STREET WINTER GARDEN FL
- SubdivisionOVERSTREET CRATE
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Aug 30, 2026
826
Single Family Listed
113
Avg DOM
279
Avg $ / SqFt
$757,830
Avg List Price
Property Summary
- Located in the OVERSTREET CRATE subdivision, 420 E CYPRESS STREET WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $410,000 and features 3 beds, 2 baths, and has approximately 1,616 square feet of living space, and was originally constructed in 1950. The current price per square foot is $254. The average price per square foot for Single Family listings in WINTER GARDEN is $279. The average listing price for Single Family in WINTER GARDEN is $757,830. To schedule a showing of MLS#o6412414 at 420 E CYPRESS STREET in WINTER GARDEN, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 420 E CYPRESS STREET
WINTER GARDEN, FL