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$410,000

420 E CYPRESS STREET, WINTER GARDEN, FL 34787

3D Tour
Active100 days on market

Beds

3

Baths

2

Sq Ft

1,616 sq ft

Year Built

1950

Lot Size

0.19 acres

Garage

About This Property

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 Overview

Property TypeResidential
Sub TypeSingle Family Residence
MLS #O6412414
StatusActive
Year Built1950
Stories1
Total Rooms3
ConstructionStucco, Wood Frame
RoofShingle
FoundationSlab
FacesNorth
SubdivisionOVERSTREET CRATE
CountyOrange
OwnershipFee Simple

Interior Features

InteriorKitchen/Family Room Combo, Stone Counters, Vaulted Ceiling(s)
FlooringLuxury Vinyl
AppliancesDishwasher, Microwave, Range, Refrigerator
LaundryOther
CoolingCentral Air
HeatingCentral

Exterior & Lot

ExteriorLighting, Other
FencingFenced, Vinyl
Lot Size0.19 acres (8,440 sq ft)
Road SurfacePaved
0

Utilities

WaterPublic
SewerPublic Sewer
UtilitiesElectricity Available

Parking

GarageNo

HOA & Community

HOANo
Senior CommunityNo

Financial Details

List Price$410,000
Original Price$425,000
Annual Taxes$5,517 (2025)
FinancingCash, Conventional, FHA, VA Loan
ZoningR-2
Parcel #122227649620028

Schools

ElementaryMaxey Elem
MiddleLakeview Middle
HighWest Orange High

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.

Location

420 E CYPRESS STREET, WINTER GARDEN, FL 34787

Listing Information

OfficeKELLER WILLIAMS ELITE PARTNERS III REALTY
ListedJune 1, 2026

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Home Price

$410,000

20% ($82,000)
6.75%

Loan Term

Principal & Interest$2,127
Property Tax (est.)$376
Insurance (est.)$150
Total Monthly$2,653
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Nearby Schools

How to Buy This Home

Multiple financing options available for this $410,000 home in WINTER GARDEN.

🏛️

FHA Loan

$14,350 Down

Government-backed, low down payment. Credit scores as low as 580.

🎖️

VA Loan

$0 Down

Zero down for eligible veterans, active duty, and military families.

🏦

Conventional

$20,500 Down

Traditional financing. As low as 3-5% down with good credit.

Florida Down Payment Assistance Programs

You may qualify for up to $35,000 in assistance to cover your down payment and closing costs.

Florida Hometown Heroes

Up to $35,000

First-time buyers working in FL

FL Assist

Up to $10,000

FHA, VA, or USDA borrowers

FL HLP Second Mortgage

Up to $10,000

First-time buyers, 0% deferred

Can You Afford This Home?

Quick check based on the 28% debt-to-income rule. Not a guarantee — just a starting point.

Listing information is deemed reliable but not guaranteed. All measurements and data should be independently verified. This information is provided by the Stellar MLS. The listing broker's offer of compensation is made only to participants of the MLS where the listing is filed. IDX information is provided exclusively for consumers' personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated: September 14, 2026.

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