420 E CYPRESS STREET, WINTER GARDEN, FL 34787

$410,0003 Beds2 Baths1,616 Sq. Ft.$254 / sq. ft.

WINTER GARDEN, FL 34787 · MLS# O6412414 · Active · OVERSTREET CRATE

Status
Active
Type
Single Family Residence
Year Built
1950
Days on Market
68
Lot Size
8,440 sqft
MLS #
O6412414
County
Orange

Description of 420 E CYPRESS STREET, WINTER GARDEN, FL 34787

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.

Property Details for 420 E CYPRESS STREET, WINTER GARDEN, FL 34787

Bathrooms Full
2
Bathrooms Half
0
Interior Features
Kitchen/Family Room Combo, Stone Counters, Vaulted Ceiling(s)
Appliances
Dishwasher, Microwave, Range, Refrigerator
Flooring
Luxury Vinyl
Heating
Central
Cooling
Central Air
Furnished
Unfurnished
Pool Private
No
Direction Faces
North

Building Information for 420 E CYPRESS STREET, WINTER GARDEN, FL 34787

Building Area Total
1616
Building Area Units
Square Feet
Stories Total
1
Association
No

Property Information for 420 E CYPRESS STREET, WINTER GARDEN, FL 34787

Lot Size Square Feet
8,440
Waterfront
No
View
No
Construction Materials
Stucco, Wood Frame
Roof
Shingle
Exterior Features
Lighting, Other
Sewer
Public Sewer
Water Source
Public
New Construction
No

Public Records for 420 E CYPRESS STREET, WINTER GARDEN, FL 34787

Parcel Number
122227649620028
Tax Annual Amount
$5,517
Tax Year
2025
Tax 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
Zoning
R-2
County Or Parish
Orange

Schools Near 420 E CYPRESS STREET, WINTER GARDEN, FL 34787

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

School assignments are provided by the listing and should be independently verified.

Payment Calculator

Estimated Payment
$2,738/mo
Principal & Interest
$2,073
Property Taxes
$460
Home Insurance
$205

Estimate only — actual rates, taxes and insurance vary. Not a loan offer or financial advice. Financing through Matthew Gromadzki, NMLS #2560919 · Innovative Mortgage Services, Inc., NMLS #250769.

Location

420 E CYPRESS STREET, WINTER GARDEN, FL 34787 · See all Winter Garden homes for sale

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More information about 420 E CYPRESS STREET, WINTER GARDEN, FL 34787

420 E CYPRESS STREET is a single family home for sale in WINTER GARDEN, FL 34787. This property was listed for sale on June 1, 2026 by KELLER WILLIAMS ELITE PARTNERS III REALTY, it's currently listed at $410,000. This listing's school district is Orange Public Schools. Nearby schools include Maxey Elem, Lakeview Middle and West Orange High. 420 E CYPRESS STREET is a 3-bed, 2-bath, 1,616 sqft single family home built in 1950.