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$425,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,616 Sq. Ft.
  • Updated 8 hours ago

Next open house:

Open House: 5:00 PM - 7:00 PM

Friday 6/5 5:00 PM - 7:00 PM

420 E Cypress Street,Winter Garden, FL 34787

420 E Cypress StreetWinter GardenFL34787

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Join us at 420 E Cypress Street on:

  • Open House: 1:00 PM - 3:00 PM

    Saturday 6/6 1:00 PM - 3:00 PM

    420 E Cypress Street,Winter Garden, FL 34787
    420 E Cypress StreetWinter GardenFL34787
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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.

Full Property Details for 420 E Cypress St

General

  • Price: $425,000
  • Taxes: $5,517 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6412414
  • Updated: 6/1/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 3
  • Interior Features: Kitchen and Family Room Combination, Stone Counters, Vaulted Ceiling(s)
  • Appliances: Dishwasher, Microwave, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Luxury Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Other

Exterior

  • Exterior Features: Lighting, Other

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: OVERSTREET CRATE
  • Driving Directions: FL-408 W. Exit 267B.Merge onto FL-50 W/W Colonial Dr. Turn right onto 9th St. Turn left onto E Cypress St. Destination will be on the left.
  • Direction Faces: North

School Information

  • Elementary School: Maxey Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Available

Structural Information

  • Exterior Const.: Stucco, Wood Frame
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,616
  • Sq. Ft. Source: Public Records
  • Year Built: 1950

Lot Features

  • Lot Size (Acres): 0.19
  • Lot Size (Sq. Ft.): 8,440
  • Lot Size: 8440
  • Street/Road Desc.: Paved
  • Fencing (Description): Fenced, Vinyl

Financial Considerations

  • Tax Amount: $5,517.38
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: OVERSTREET CRATE COMPANYS F/9 THE E 60 FT OF W 199 FT OF S1/2 OF N1/2 OF S1/2 BLK S IN SEC 23-22-27 SE1/4
  • Flood Zone Info: X
  • APN: 122227649620028
  • Property ID: 122227649620028
  • Block/Lot/Section: 20

Listed by Keller Williams Elite Partners Iii Realty

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Listing agent

— 420 E Cypress St —

  • Keller Williams Elite Partners Iii Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 420 E Cypress St

School District:Orange County School District
NameGradesDistance
William S Maxey Elementary School
1100 East Maple Street, Winter Garden, FL 34787
PK-50.8 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-81.7 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-121.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 420 E Cypress St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/01/2026
Listed
$425,000
112.5%
MLS
1/29/2021
Sold
$200,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 420 E Cypress St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,517
—
$314,980
-1%
2025
$5,517
13%
$318,130
9%
2024
$4,881
28%
$292,192
23%
2023
$3,818
112%
$236,826
72%
2021
$1,802
-47%
$137,481
-32%
2022
$3,394
88%
$201,981
49%
2021
$1,802
3%
$135,583
2%
2019
$1,745
-25%
$132,535
4%
2018
$2,330
76%
$127,948
85%
2017
$1,324
11%
$69,154
18%
2016
$1,192
—
$58,517
2%
2015
$1,192
96%
$57,100
24%
2014
$607
2%
$46,095
1%
2013
$593
—
$45,414
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 420 E Cypress St

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Keller Williams Elite Partners Iii Realty

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420 E Cypress Street, Winter Garden, FL 34787 (MLS# O6412414) is a Single Family property with 4 bedrooms and 2 full bathrooms. 420 E Cypress Street is currently listed for $425,000 and was received on June 01, 2026. Want to learn more about 420 E Cypress Street? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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